Welcome back to the Launch Key 🚀 

If you listen to the tech bro podcasts (full disclosure: I do), the pattern emerging is clear: we're in the infrastructure phase of the AI revolution. The Nvidia hype last year. OpenAI and Anthropic racing to be trillion dollar companies while hemorrhaging money. And now data center fights around the country.

It reminds me of previous tech cycles. And the winners in those earlier cycles were companies that simply applied new tech in a way that ultimately reduced costs or increased sales.

It’s a story as old as the gold rush.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Take this week’s poll or comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • Blue Collar AI

• Old School Wisdom

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

History often rhymes.

In the 1850’s the California Gold Rush lured thousands to leave their farms, shops, towns and go west, young man for the prospecting ideal of striking gold. Samuel Brannan was arguably the first minted millionaire from that gold rush and he earned it not by striking gold - but by selling picks and shovels to the dreamers. Brannan squandered his gold rush lead while Levi Strauss built an empire from the same start.

We’ve watched recent gold rushes with websites ("we don't need one"), then e-commerce, then mobile, then crypto and now AI. Lather. Rinse. Repeat. The pattern is always the same: early movers look like weirdos, then they look like geniuses, then everyone else scrambles.

One of the more interesting early moving examples right now, is people in the trades leveraging AI. At first I thought it was a few outliers, but there is mounting evidence of a fantastic trend. Mike Rowe has been right about the trades all along.

Smart people in the trades are applying AI to their daily jobs in ways that will create incredible moats around their businesses. They don’t care if the tools aren’t fully developed. It doesn’t bother them that we need more data centers. They are simply taking charge of their future and improving how they work.

Blue Collar AI

My X.com feed has started to surface really interesting examples:

• A roofing company is using AI agents to pull satellite imagery, cross-reference hail damage, and feed warm leads to their sales team.

• An electrician is using AI to create a panel schedule calculator that reads blueprints and generates load calculations with NEC code compliance.

• A fence contractor is creating a property line overlay tool using GIS data to auto-generate material quotes and permit docs.

• A pest control operator is building a route optimization and chemical usage tracking app with state reporting compliance.

The best part is that none of these guys knew how to code.

They ran businesses that were too small for big software like SAP, Salesforce or ServiceNow. And the tools they did buy couldn’t solve their real problems. So they took it upon themselves to solve them by explaining it to AI. And walking step-by-step through their domain expertise until they had solutions.

These businesses will shed whatever extra software tools they used in the past. A plumber using Claude Code isn't "learning to code." He's building a quoting tool that works the way his business actually works. Because the one he's paying $1,200 a month for doesn't.

Todd Saunders has collected over 200 examples and shares their stories on his feed. But the one that I saw first was Cory LaChance, a mechanical engineer in industrial piping construction in Houston. He normally works with chemical plants and refineries, but now he talks to Claude and works with Terminal.

Twitter tweet

LaChance didn’t just solve it for himself, he turned his solution into a new business revenue stream. TakeOffTrak allows customers to automate their own piping takeoffs.

TakeOffTrak

AI-powered pipe fabrication takeoff platform

Nathan Spearing runs Transform NC, a remodeling company in North Carolina. He created his own AI agent to handle email, qualify leads, create estimates, track projects, and manage his calendar — all while he’s on a job site.

He didn't build it because he’s a tech guy. He built it because he was drowning in texts, losing leads, and spending evenings on paperwork instead of with his young family.

Today he teaches other contractors to do the same thing. Not with some generic SaaS — but by creating their own agent that learns their businesses, clients and their way of doing things.

BlueCollarOS — AI That Knows Your Trade

An AI agent that works with your existing tools and gets smarter every day. Built by a contractor, running in real businesses.

Here's the thing – you don't need to be in the trades to see the pattern.

Every one of these guys did the same thing you can do — they took deep domain expertise, explained the problem to AI, and walked it through step by step until they built a solution.

I wrote a longer article for non-technical entrepreneurs that highlights 7 tools you can use to do exactly this.

The pick-and-shovel play of this gold rush isn't selling AI how-to courses. It's being the person who knows what to build with them. You've spent decades learning how things actually work.

That knowledge just became the most valuable input in the room.

Now go launch something 🚀 

You've Spent 30 Years Building Expertise. It's Time to Turn It Into Income That Works for You.

The complete framework for professionals 50+ who want to build multiple revenue streams without quitting their job or betting everything on a startup.

Old School Wisdom

Crossing the Chasm has sold over a million copies and is widely considered one of the most influential business books of the past thirty years, particularly in technology and venture capital circles.

The early adopters mentioned in this Launch Key issue have given their businesses a tremendous advantage by jumping that chasm now.

Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream

Crossing the Chasm, first published in 1991 and revised in 1999 and 2014, is Geoffrey Moore's landmark guide to marketing disruptive innovations.

Become An AI Expert In Just 5 Minutes

If you’re a decision maker at your company, you need to be on the bleeding edge of, well, everything. But before you go signing up for seminars, conferences, lunch ‘n learns, and all that jazz, just know there’s a far better (and simpler) way: Subscribing to The Deep View.

This daily newsletter condenses everything you need to know about the latest and greatest AI developments into a 5-minute read. Squeeze it into your morning coffee break and before you know it, you’ll be an expert too.

Subscribe right here. It’s totally free, wildly informative, and trusted by 600,000+ readers at Google, Meta, Microsoft, and beyond.

Free Knowledge

Even if they don’t use AI, the blue collar guys are making money literally using picks and shovels while they build all the data center infrastructure that AI will require.

The Invisible, Profitable, Unsexy Businesses Behind The Trillion-Dollar AI Boom

The Invisible, Profitable, Unsexy Businesses Behind The Trillion-Dollar AI Boom

Recommendations

🤖 AI Report : 400,000+ business leaders (and teams at IBM, AWS & Zapier) start their day with The AI Report. 5 minutes. Plain English. No hype.

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀 

This week we touch on a topic that keeps uncovering more valuable data each week – our grey-headed interpersonal skills are very valuable in the AI economy.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Take this week’s poll or comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • What Elon taught us

  • Company Lifeblood

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

I had absolutely no master plan as a senior in college.

An English major who thought he wanted to write for Sports Illustrated. I interviewed with a few publishing houses in New York over Spring Break. Dismal outcome. I learned that my first job would probably be writing obituaries for a small town newspaper.

My father helped me pivot with some excellent advice. He understood that my first job was probably not going to be a career, but simply my first business experience.

His exact quote was about understanding the difference between line and staff positions. Every company has both. Just how did a company make money? Make sure you’re on the side that generates revenue. Sales is the job that matters most.

So I interviewed for sales positions. And landed one. And gave up on the writing career until this late-career side hustle.

What Elon taught us

Line vs. staff has a much sharper lens today — after Elon fired 80% of Twitter employees when he purchased that company. Staff bloat had rendered the platform into a typical 8000-employee Silicon Valley big tech company.

They’ve hired a few hundred people back, but today X.com is working well with approximately 2000 employees.

Twitter Layoffs: How Many Employees Were Fired and Where They Went Next

Explore Elon Musk’s Twitter layoffs: how many employees were fired, what happened to the workforce before and after, and where ex-employees went next.

Jack Dorsey, another tech titan who has been right and early multiple times – recently cut 40+% of the staff at Block (formerly Square) a company with a $39b market cap.

Jack Dorsey Is Ready to Explain the Block Layoffs

In an exclusive interview with WIRED, Block’s cofounder and CEO says he axed 40 percent of his workforce so that he can rebuild the company “as an intelligence.”

This time it’s because recent advances in AI tools are forcing Block to remake itself as a slimmer, more nimble entity. Block has removed layers of middle management and is delivering better products faster.

These stories are the canary in the coal mine for the Fortune 500. It’s not just big tech who will benefit from efficiency gains - its Financial Services, Healthcare, Engineering, Retail, Ecommerce, Consulting and more. Shareholders will demand it.

All the ‘Learn-to-code’ people have been wrong for a long time. Coding has become a commodity. High-leverage engineers with AI can do 10x-100x what they could two years ago.

Company Lifeblood

You know what these firms are not cutting?

Sales.

There's a reason for that.

Sales is the original line function. It's how a company touches money. It requires judgment, trust, relationship, and the ability to read a room — none of which a model can own on your behalf. The same goes for anyone who can originate ideas, see patterns before the data confirms them, or walk into a conversation and understand what someone actually needs versus what they say they need.

My father didn't know anything about AI. He knew that companies have a center of gravity — and that gravity is always revenue. Everything else is infrastructure for the people doing the revenue work. That distinction is older than org charts. It just got a lot more visible when Elon fired 6,000 people and the site didn't go down.

You'd better get good at selling

You'd better get good at selling

www.contrarianthinking.co/newsletter-articles/youd-better-get-good-at-selling

You spent decades building the kind of judgment that can't be measured — and according to a February 2026 MIT Sloan working paper, that's precisely what the agentic economy is about to make scarce and premium. The paper puts it plainly: when AI makes execution abundant, the binding constraint becomes verification. The ability to audit, steer, and underwrite decisions. That's not a junior skill. That's forty years of being in the room.

The question isn't whether AI will take your job. The question is whether you're positioned on the line — where judgment, relationships, and ideas create value — or on the staff side, where execution is being handed to machines faster than anyone predicted.

I am grateful that my father gave me that view 40+ years ago. The economy just made it more urgent.

If you've been waiting for the right moment to bet on your experience rather than your title — this is it.

Now go launch something 🚀 

You've Spent 30 Years Building Expertise. It's Time to Turn It Into Income That Works for You.

The complete framework for professionals 50+ who want to build multiple revenue streams without quitting their job or betting everything on a startup.

Modern Tools

Are you questioning how AI can really benefit you? Are you unimpressed with ChatGPT? Here’s a great first step to reduce friction in whatever you type.

Just talk into any app on your phone.

I started using Wispr a few months ago to streamline adding personal notes. Grocery store items, newsletter topics, To Do’s – the kind of stuff I typically typed into an iphone reminder.

Today, I’m dictating detailed ideas directly into my Notion inbox, framing up complete Launch Key issues.

Easy win making AI work for me.

Wispr Flow | Effortless Voice Dictation

Flow makes writing quick and clear with seamless voice dictation. It is the fastest, smartest way to type with your voice.

wisprflow.ai

Your Retirement Savings Need to Outlast You

Most retirement plans underestimate two things: how long your savings need to last, and how quietly inflation erodes them along the way.

The 15-Minute Retirement Plan helps you close both gaps with practical guidance on longevity risk, purchasing power, and building a financial plan that doesn't run out before you do.

If you have $1,000,000 or more saved, download your free guide to start.

Download Your Free Guide.

Free Knowledge

Need to refresh your sales skills for today’s buyer? HubSpot Academy has free online tools: Inbound Sales, Sales Enablement, and Frictionless Sales certifications with video lessons and quizzes.

Sales Training | Hubspot

Free sales training courses, lessons, and tools to grow your pipeline and your career.

www.hubspot.com/sales/sales-training

Recommendations

🤖 AI Report : 400,000+ business leaders (and teams at IBM, AWS & Zapier) start their day with The AI Report. 5 minutes. Plain English. No hype.

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

The startup world has a mythology problem.

It goes something like this: the best entrepreneurs are young, hungry, and working out of a garage. They drop out of college, raise venture capital from Sand Hill Road, and build billion-dollar companies before they turn 30. Everything else is a footnote.

That mythology is also, factually, wrong.

A joint study by MIT and the U.S. Census Bureau analyzed 2.7 million startup founders and found that the average age of the most successful ones — the companies that hit the top 0.1% in growth — was 45. Not 25. Not 30. Forty-five.

A 50-year-old entrepreneur is twice as likely to build a massively successful company as a 30-year-old. A 60-year-old is three times as likely.

The data doesn't care about the mythology. And neither should you.

What a Late-Career Entrepreneur Actually Is

The term sounds like a consolation prize. "Late-career" — as if you missed the main event and are showing up for the afterparty.

That's not what it means. Not even close.

A late-career entrepreneur is someone who has spent 20, 25, or 30 years building expertise, networks, and pattern recognition inside organizations — and is now pointed at a problem worth solving on their own terms. They're not starting a business because they ran out of other options. They're starting because they finally have everything they need to do it right.

The difference between a 28-year-old founder and a 52-year-old founder isn't ambition. It's ammunition.

The 28-year-old has energy, tech fluency, and the willingness to live on ramen and optimism for two years. Genuinely useful. But they're also working with theory, not evidence. They haven't seen a market cycle. They haven't managed a team through a crisis. They haven't watched a company fail because the founders ignored their customers and fell in love with their product instead.

The 52-year-old has all of that. The hard lessons are already paid for. The pattern recognition is already built. The network is already there.

You're not late to entrepreneurship. You're loaded for it.

The Three Myths Worth Demolishing

The Actual Advantages of Starting Later

Let's be specific. Here's what you have that a younger founder doesn't.

• Pattern recognition. You've watched enough business cycles, product launches, leadership failures, and market shifts to know what actually matters versus what just seems urgent. This is worth more than any MBA program, and you can't buy it — you have to earn it over years.

• Domain expertise. You know an industry from the inside. You know where the money actually flows, who the real decision-makers are, what the customers are genuinely frustrated by, and what solutions have already been tried and failed. That knowledge is the foundation of every good business

• A real network. Not LinkedIn connections — actual relationships built over decades of working alongside people, delivering on commitments, and showing up when it counted. Your network is your distribution channel, your first customers, your advisors, and your referral engine. Young founders spend years trying to build what you already have.

• Access to capital. Most late-career entrepreneurs have savings, home equity, and a financial cushion that allows them to make calculated bets without betting the house. This changes the psychology of risk entirely. You can afford to experiment.

• Credibility on arrival. When you walk into a room and say you've spent 25 years solving a particular problem, people believe you. You don't have to earn credibility from scratch — you're walking in with a track record. In professional services, consulting, and B2B businesses, that credibility is the product.

• Time perspective. Here's the one nobody talks about. A 28-year-old founder who builds something over five years has built something between ages 28 and 33. A 52-year-old who builds something over five years has built something between ages 52 and 57 — and potentially runs it for another 20-25 productive years. The timeline for a late-career venture is not shorter. It's different.

What the Research Actually Shows

The MIT/Census study is the most comprehensive look at founder age and success ever conducted. But it's not the only data point.

The Kauffman Foundation — which tracks entrepreneurship more carefully than anyone — consistently finds that people over 50 launch more businesses per capita than any other age group. The 55-64 demographic has seen the fastest growth in new business formation over the past two decades.

Five years after founding, 70% of businesses started by entrepreneurs over 50 are still operating. The comparable number for businesses started by founders under 30 is 28%.

Survival rate. Not just launch rate. Survival.

The difference is experience. When you've seen a business fail, you know what the early warning signs look like. When you've managed a team through a crisis, you know how to make decisions with incomplete information. When you've negotiated a contract, you know what the other side is actually trying to protect.

Experience doesn't guarantee success. But it changes the odds dramatically.

The Late-Career Entrepreneurs Who Proved It

You already know some of these names. But it's worth saying them out loud, because the mythology has a way of making us forget.

You've Spent 30 Years Building Expertise. It's Time to Turn It Into Income That Works for You.

The complete framework for professionals 50+ who want to build multiple revenue streams without quitting their job or betting everything on a startup.

launchkey.gumroad.com/

The Digital Moment That Changes Everything

Here's what's different right now that wasn't true when Ray Kroc was selling milkshake machines.

The cost of starting a business has collapsed.

A newsletter that reaches 18,000 people costs less than $150 a month to run. A digital product — a PDF guide, a template, a short course — can be built in a weekend and sold globally with no inventory, no shipping, and no retail. AI tools that cost $20 a month can do research, write first drafts, analyze data, and answer customer questions at a scale that previously required a team.

The execution gap that used to favor younger, faster, better-resourced founders has narrowed dramatically. What remains — domain expertise, pattern recognition, credibility, network — is exactly what late-career entrepreneurs have in abundance.

This is the best moment in history to be a late-career entrepreneur. Not despite the technology. Because of it.

One Question Worth Sitting With

Here's what separates the late-career entrepreneurs who actually build something from the ones who spend years thinking about it:

They stopped waiting for permission.

They didn’t ask permission from the market — though the market will always have an opinion. Permission from themselves. The internal voice that says you need more preparation, more research, more certainty before you start. The one that reminds you of everything that could go wrong.

That voice is experience speaking. It's not wrong. But it's also not the whole story.

At 60, I realized I wasn’t done yet and started a newsletter - something I’d never done before.

The other thing experience teaches you — if you let it — is that most of the things you worried about never happened, and most of the problems you actually faced were ones you couldn't have anticipated anyway. Which means the best preparation isn't more research. It's starting.

You've spent decades getting ready for this, whether you planned it that way or not.

The most direct route off the corporate merry-go-round is you.

Now go launch something 🚀 

Every Tuesday morning, Launch Key delivers one practical idea for executives building their next chapter — digital products, AI tools, career portfolios, and the mindset to make it real. 18,000+ subscribers. Free forever.

Subscribe to Launch Key →

Also worth reading: 12 Encore Career Ideas for Executives →

Rob Norris is a serial entrepreneur, tech leader, and publisher of Launch Key. He has founded companies, led technology organizations, and spent 35+ years watching who actually wins in business. Spoiler: it's rarely who the magazines predicted.

Welcome back to the Launch Key 🚀 

2 months ago, Steven Shorkey wrote a guest post about embracing the mastery of your hard-earned knowledge. And he was spot on.

But the last 60 days have felt like decades of technology evolution. Every day I wake up to exponential updates. Driving to dental appointments last week, I caught up with an important podcast that confirmed this insane flywheel.

And the takeaway is that while mastery is now more attainable than ever, those who already have it are in the drivers seat.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Take this week’s poll or comment below and let me know if we’re on the right track.

• If you're thinking about your next chapter, start with 12 Encore Career Ideas for Executives →

Table of Contents

• Pull to Eject

  • Late-career professionals have a structural advant …

• Modern Tools

• Old School Wisdom

• Recommendations

• Visual Crapshoot

Pull to Eject

How many times have you repeated a podcast?

Last week, I needed 3 different sessions listening to Christian Catalini discuss the new paper Some Simple Economics of AGI.

Catalini is a researcher, entrepreneur (co-created Diem) and the founder of the MIT Cryptoeconomics Lab. He is a technology optimist who’s known for his research on cryptocurrencies and blockchain, and has a well-informed view of AI. And this new paper is worth your time.

Catalini and his co-authors wrote: "Today's defining challenge is not the race to deploy the most autonomous systems; it is the race to secure the foundations of their oversight. Only by scaling our bandwidth for verification alongside our capacity for execution can we ensure that the intelligence we have summoned preserves the humanity that initiated it."

Abstract

For three hundred thousand years, human cognition was the primary engine of progress on Earth. Today, as AI decouples cognition from biology, its capacity to recombine knowledge—and exhaustively map every combination within the known landscape—is driving the marginal cost of measurable execution toward zero.

The conversation is chock full of clear-eyed future thinking.

One of his more interesting answers was the education of pre-teen kids. Mastery is now within everyone’s grasp - and much sooner.

The traditional path to mastery (K-12 → college → apprenticeship → time → expertise) was never about learning — it was about access to resources, mentors, and credentialing gatekeepers. AI removes most of those gates.

Parents and kids today might identify areas of genuine interest (languages, STEM, writing, art, music, etc) then using AI tools to learn, create, and direct their own projects. They become the director of their education, not the executor. They won’t need the traditional K-12 conveyor belt and will be years ahead of their peers with actual experience and deep subject knowledge.

Sidebar: its important to watch how the tech leaders let their own children use the technology they’re funding or building. I’ve commented before on what Andreessen, Palihapitiya and Musk have done. They didn’t just give their kids ipads for instance. Silicon Valley leaders who denied their kids early social media usage were just proven correct (Meta, Google lose US case over social media harm to kids).

Back to the topic, the Catalini paper’s central economic logic: when intelligence becomes cheap, value migrates to its scarcest complement — trustworthy verification.

Catalini is on the circuit pitching their work, and I caught the message (multiple times) on the A16Z Pod AI just gave you Super Powers - Now What?

AI Just Gave You Superpowers — Now What?

A new paper, “Some Simple Economics of AGI,” is making the rounds—Web3 with a16z we sat down with author Christian Catalini (MIT Crypto Economics Lab) and Eddy Lazzarin (CTO of a16z crypto), in conversation with Robert Hackett, to unpack what AGI could mean for work and markets.

Late-career professionals have a structural advantage

Experience, judgment, and accountability — your non-measurable capacities built over decades — are precisely what the agentic economy makes scarce and premium.

The race to deploy AI agents is exciting but their ultimate success will come from the intelligence of the underlying model - or your uncommon knowledge.

In his bestseller, Mastery, Robert Greene details the unvarnished Ben Franklin story: self-taught dropout rising to prominence as one of the greatest Americans using social intelligence as an indispensable component of his mastery.

It took Franklin decades to evolve from printer’s apprentice to statesman, scientist, and diplomat. He was enabled not just by intellectual ability but by an extraordinary capacity to read people and navigate social environments - the exact things you’ve been doing as you’ve gained mastery throughout your work career.

As AI makes cognitive execution abundant, the new scarce resource are experienced professionals already on the other side of the traditional path.

Professionals just like you.

Late-career folks have the taste, judgment, and domain knowledge. What we lacked was the execution capacity to act on it without a team.

That gap is now closed.

Mastery + AI agency = the most powerful combination in the second-act economy.

Giddyup.

Now go launch something 🚀 

You've Spent 30 Years Building Expertise. It's Time to Turn It Into Income That Works for You.

The complete framework for professionals 50+ who want to build multiple revenue streams without quitting their job or betting everything on a startup.

launchkey.gumroad.com/

Modern Tools

If you’re still just dabbling with the free versions of ChatGPT, Grok, Claude or Gemini, let me make a suggestion: Upgrade to a paid version. Get the latest model and see incredible results.

I upgraded to Claude Pro in late 2025 and the responses only get better with each chat. It’s helped me create a far better Notion knowledgebase of my own ideas, books, business experience and topics. It’s allowed me to create and test a few of my own agents. And I am developing a Claude-based research assistant now.

The AI for Problem Solvers | Claude by Anthropic

Claude is Anthropic's AI, built for problem solvers. Tackle complex challenges, analyze data, write code, and think through your hardest work.

claude.com/product/overview

Old School Wisdom

Mastery is not a gift — it is an inevitable outcome. Robert Greene organized the book into six interlinked chapters that map a three-phase arc — Apprenticeship, Creative-Active, and Mastery. Study the behaviors of Albert Einstein, Charles Darwin, Benjamin Franklin, Leonardo da Vinci and the nine contemporary Masters interviewed for this New York Times #1 Bestseller.

Mastery eBook : Robert Greene Kindle Store

Mastery - Kindle edition by Greene, Robert. Download it once and read it on your Kindle device, PC, phones or tablets. Use features like bookmarks, note taking and highlighting while reading Mastery.

Your Boss Will Think You’re an Ecom Genius

If you’re optimizing for growth, you need ecomm tactics that actually work. Not mushy strategies.

Go-to-Millions is the ecommerce growth newsletter from Ari Murray, packed with tactical insights, smart creative, and marketing that drives revenue.

Every issue is built for operators: clear, punchy, and grounded in what’s working, from product strategy to paid media to conversion lifts.

Subscribe for free and get your next growth unlock delivered weekly.

Sign up now

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

A Plain-English Guide to AI Tools for the Non-Technical Entrepreneur

Let's start with the fear.

Because it's real and nobody's saying it out loud.

You've watched AI go from a buzzword to something genuinely disruptive in about eighteen months. You've seen the headlines about jobs being automated, industries being upended, and a new generation of 25-year-olds who seem to move at a speed that wasn't possible five years ago. And somewhere in the back of your mind, a quiet voice has been asking: am I already behind?

Here's the honest answer: not yet. But the window is closing.

The executives and late-career professionals who figure out how to use AI as a force multiplier in the next twelve months will have an almost unfair advantage over those who don't.

Not because they'll become AI engineers — they won't. But because AI removes the friction that previously made it expensive and time-consuming to operate as a one-person business.

The competitive moat used to be execution capacity. The 28-year-old with three co-founders, two developers, and unlimited energy could outrun the 55-year-old with better ideas and deeper experience. AI narrows that gap dramatically. In some cases, it eliminates it entirely.

This is not an article about the future of work. It's a practical guide to the tools that are available right now, what they actually do, and how a non-technical professional can start using them this week.

No coding required. No computer science degree. Just a willingness to experiment.

The One Reframe That Changes Everything

Stop thinking of AI as a technology you need to understand.

Start thinking of it as the most capable, most available, cheapest employee you've ever had access to — one that never sleeps, never complains, and can turn a rough idea into a finished first draft in about forty-five seconds.

You don't need to understand how your car's engine works to drive it. You don't need to understand how electricity is generated to use the lights. AI is the same. What matters is knowing what tasks to hand off, and what to keep for yourself.

The tasks worth handing off: first drafts of anything, research, summarization, formatting, scheduling, repurposing content, answering routine questions, generating options and variations.

The tasks worth keeping: judgment calls, relationship management, strategic decisions, anything that requires your specific credibility and lived experience to carry weight.

Your experience is the input. AI is just the accelerant.

The 7 Tools Worth Your Time Right Now

These are not hypothetical or experimental. They are tools that one-person businesses — including this newsletter — use weekly. Each one is accessible without technical skills, and each solves a specific problem that previously required either significant time or hiring someone. I highlight Modern Tools in most weekly Launch Key issues.

1. Claude (claude.ai) — Your Thinking Partner

What it does: Claude is a conversational AI built by Anthropic that excels at long-form writing, analysis, strategy, and nuanced reasoning. You talk to it like a smart colleague and it helps you think through problems, draft documents, stress-test ideas, and produce content.

How late-career professionals use it:

• Draft newsletter issues, LinkedIn posts, and articles from a rough outline

• Summarize long documents, reports, or research papers in two minutes

• Prepare for difficult conversations — give it the context and ask it to play devil's advocate

• Brainstorm product ideas, pricing strategies, and positioning angles

The edge you have: Claude responds to context and nuance. The richer the professional background you bring to a conversation, the better the output. A 30-year career's worth of industry knowledge produces dramatically better results than a prompt from someone starting from scratch.

Cost: Free tier available. Paid plan at $20/month unlocks significantly more capability.

2. ChatGPT (chatgpt.com) — The Versatile Workhorse

What it does: OpenAI's ChatGPT is the most widely known AI tool, and for good reason — it handles an enormous range of tasks across writing, coding, data analysis, image generation, and research.

How late-career professionals use it:

• Build custom GPTs trained on your own content, processes, and voice — essentially a digital assistant that knows your work

• Analyze spreadsheets and business data without needing Excel expertise

• Generate images for presentations, social posts, and websites

• Research competitors, industries, and market trends quickly

The edge you have: Custom GPTs are particularly powerful for experienced professionals. You can train one on your methodology, your past work, your communication style — and it will produce outputs that sound like you and reflect your expertise.

Cost: Free tier available. ChatGPT Plus at $20/month for advanced features.

3. Perplexity (perplexity.ai) — Research Without the Rabbit Hole

What it does: Perplexity is an AI-powered search engine that answers questions with cited sources rather than a list of links to click through. Ask a question, get a synthesized answer with references you can verify.

How late-career professionals use it:

• Market research in minutes instead of hours

• Competitive intelligence — "What are the main criticisms of fractional CFO services?"

• Staying current on industry trends without drowning in news feeds

• Fact-checking claims before you publish or present them

Why this matters: One of the genuine competitive advantages of experience is knowing what questions to ask. Perplexity rewards that instinct — it's built for people who already have a framework and need to fill in the data.

Cost: Free tier is genuinely useful. Pro at $20/month for more depth and sources.

4. Beehiiv AI — Newsletter Creation Inside Your Platform

What it does: If you're running a newsletter on Beehiiv — or considering it — the platform has built AI tools directly into the writing and growth workflow. This includes writing assistance, subject line generation, and automated content recommendations.

How late-career professionals use it:

• Generate subject line variations and pick the strongest one before sending

• Polish and tighten newsletter copy without leaving the platform

• Get content recommendations based on what's performing well with your audience

Why this matters: The bottleneck for most newsletter publishers isn't ideas — it's the time between idea and published issue. Reducing that friction is how you show up more consistently, which is the single most important factor in audience growth.

Cost: Included in Beehiiv paid plans starting at $39/month.

You've Spent 30 Years Building Expertise. It's Time to Turn It Into Income That Works for You.

The complete framework for professionals 50+ who want to build multiple revenue streams without quitting their job or betting everything on a startup.

launchkey.gumroad.com/l/ffjvdt?layout=profile

5. Canva AI — Design Without a Designer

What it does: Canva has been adding AI features at a rapid pace. The result is a design platform that now lets non-designers produce professional-quality graphics, presentations, social posts, and documents using AI to do most of the heavy lifting.

How late-career professionals use it:

• Create featured images for articles and newsletter issues in minutes

• Build lead magnets, PDF guides, and digital product covers without hiring a designer

• Generate on-brand social graphics from a text description

• Produce presentation decks that look like a design agency made them

Why this matters: The visual quality of your digital presence signals credibility to new visitors before they read a single word. Canva AI makes professional-quality design accessible to anyone who can describe what they want.

Cost: Free tier is useful. Canva Pro at $15/month unlocks the full AI feature set.

6. Otter.ai — Turn Conversations Into Content

What it does: Otter records, transcribes, and summarizes conversations — meetings, interviews, podcast recordings, voice memos. What would have taken hours of manual transcription happens automatically in minutes.

How late-career professionals use it:

• Record a 20-minute voice memo of your best thinking on a topic, get it transcribed, and turn it into a newsletter issue or article draft

• Capture client meeting notes automatically and get a summary without touching a keyboard

• Interview a guest for your podcast and have a full transcript within minutes of finishing

The edge you have: Your best thinking often comes out in conversation, not at a keyboard. Otter captures that thinking without requiring you to write it down. For people who have decades of knowledge that is better spoken than typed, this is a significant unlock.

Cost: Free tier covers basic use. Pro at $17/month for advanced features.

7. Zapier — The Glue That Connects Everything

What it does: Zapier connects your different tools and automates the handoffs between them, without any coding. When X happens in one tool, Y automatically happens in another.

How late-career professionals use it:

• New newsletter subscriber → automatically added to a welcome email sequence

• New Gumroad purchase → automatically sends a thank-you and delivery email

• New blog post published → automatically posts a notification to LinkedIn and X

• Form submission from a potential consulting client → automatically creates a task in your project management tool

Why this matters: Automation is how one-person businesses compete with teams. Every repetitive task you automate is time you reclaim for the work only you can do. Zapier makes that automation accessible without a developer.

Cost: Free tier handles basic automations. Paid plans from $20/month for more complex workflows.

The One Workflow That Changes Everything

Here's the specific system that can save you 4–6 hours per week and improve the quality of everything you publish — using tools you can set up in an afternoon.

The Content Multiplication Workflow:

1. Write or record once. Draft your weekly newsletter issue in Claude, or record your thinking into Otter as a voice memo.

2. Extract the core idea. Ask Claude: "Here's my newsletter issue. Give me the single most provocative insight in one sentence."

3. Generate LinkedIn posts. Ask Claude: "Turn this newsletter into three different LinkedIn posts — one that leads with a personal story, one that leads with the data, one that leads with a contrarian take."

4. Generate Twitter/X posts. Ask Claude: "Turn the best insight from this newsletter into a 5-tweet thread for a late-career entrepreneur audience."

5. Generate a subject line. Ask Beehiiv AI or Claude for five subject line options. Pick the one that creates the most curiosity.

6. Create the visual. Open Canva AI, describe what you want, download the featured image in 3 minutes.

7. Zapier handles the rest. Publishing triggers automatic distribution to your connected channels.

One piece of core thinking becomes a newsletter, three LinkedIn posts, a Twitter thread, a visual, and automated distribution — in roughly ninety minutes instead of a full day.

That's what AI leverage looks like in practice. Not magic. Just systematized.

What AI Cannot Replace — And Shouldn't Try

This is the part that matters most, and the part that most AI articles skip.

Your judgment about what's true — earned from watching industries, companies, and people over decades — is not something any AI can replicate. Your network, built on real relationships and genuine trust, doesn't transfer to a model. Your credibility, accumulated through a career of making calls and living with the outcomes, cannot be generated by a prompt.

AI is extraordinarily good at production. It is not good at wisdom.

The late-career professional's genuine competitive advantage has always been the judgment that comes from having been in the room when the decisions were made. AI doesn't threaten that. If anything, it amplifies it — because now the execution bottleneck is largely removed, and what remains is the one thing experience actually produces: knowing what's worth doing in the first place.

The 28-year-old with AI tools can move fast. The 55-year-old with AI tools and thirty years of pattern recognition can move fast and be right more often.

That's not a small distinction.

Where to Start Tomorrow Morning

Not next month. Not when you've done more research. Tomorrow morning, with coffee.

Step 1: Go to claude.ai and create a free account. Open a conversation and type: "I'm a [your background] building [what you're building]. Help me draft a LinkedIn post about [one thing you know deeply]." Read what it produces. Edit it into your voice. Post it.

Step 2: The following morning, take the same content and ask: "Now turn that into a 300-word email to my audience." Notice how fast that happened.

Step 3: After one week of this, you'll have a clear picture of where AI saves you the most time. That's when you add the next tool.

One tool at a time. One workflow at a time. Compounding over months.

The executives who will look back on 2026 as a turning point in their professional trajectory are the ones who started this week — not the ones who waited until they understood it completely.

You don't need to understand it completely. You need to start.

Now go launch something 🚀 

Looking for broader encore career options beyond AI? Start with 12 Encore Career Ideas for Executives →

Every Tuesday morning, Launch Key delivers one practical idea for executives building their next chapter — including the AI applications that actually work for one-person businesses. 18,000+ subscribers. Free forever.

Subscribe to Launch Key →

Welcome back to the Launch Key 🚀

It’s Pollination season in the land of the pines, which means great outdoor weather - with sneezing. But it also means the 1st quarter is baked.

I’ve spent the past few months on technology, but this week we go back to Launch Key origins: experienced professionals just know stuff.

And it can be the stuff you turn into a product.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Take this week’s poll or comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • The Corporate Merry-Go-Round Was Your R&D

  • The Repeating Problem Audit

  • The Validation Shortcut

  • One More Thing

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

You've been solving the same problem for decades.

Different companies. Different titles. Same headache — the quarterly reporting process that takes three weeks and shouldn't. The onboarding system that keeps breaking. The vendor negotiation playbook every new manager has to learn from scratch because nobody ever wrote it down

You solved it. Improvised a workaround. Built the spreadsheet. Trained the new hire. Moved on.

Here's what most people never realize: that solution is a product.

The Corporate Merry-Go-Round Was Your R&D

Every executive who's built something great in the creator economy will tell you some version of the same story. They didn't find a clever market gap on a whiteboard. They got tired of solving the same problem for free — and decided to start charging for it.

This is the cleanest path to a viable product that exists: build a solution for the person you used to be.

The founder of Jotform built his company for one simple reason: he was a developer wasting hours every week building forms from scratch. He hated it. He fixed it. Millions of users and a nine-figure business later, that frustration became one of the most-used SaaS tools on the planet. The insight wasn't genius. It was boredom.

Every Business Needs to Solve a Pain Point — Does Yours?

Solving pain points isn't just a path to business success; it's the foundation. Here's how to get started.

You've got the same raw material.

Probably more of it. And your experience Is the advantage.

There's a persistent myth that great founders are 23, college dropouts operating on four hours of sleep and pure audacity. The data tells a different story.

Harvard Business Review analyzed 2.7 million company founders and found that the average age of the most successful startup founders — top 0.1% by growth — was 45.

And the single strongest predictor of success? Years of experience.

Not youth, not connections to VC money – industry experience.

The problems you've watched recur across three companies, two industries, and a dozen leadership changes? You're not the only one who has them. You're just the first one who might actually know how to fix them — and who has the pattern recognition to know the fix will actually work.

The Repeating Problem Audit

Here's how to identify your best opportunity. Grab a notebook and answer these questions honestly:

• What problem did I solve that nobody asked me to? The thing you quietly fixed because you couldn't stand watching it break.

• What process did I rebuild every time I joined a new team? The onboarding doc. The tracking sheet. The communication framework.

• What did I train colleagues on repeatedly — the thing that felt like common sense to me but was foreign to everyone else?

• What did I spend money on personally, or beg a budget committee to fund, because no existing tool did it right?

The sweet spot is where two or more of these questions point to the same answer. That intersection is your product idea. That idea is far more important than what tools you use to build it.

The Validation Shortcut

Here's the part that never gets talked about enough: you have a built-in unfair advantage when it comes to validating your idea.

Spend a few minutes on AI x.com and the vibe-coding first-time founders don’t know if their target customers actually want what they’re building. You don't have that problem.

You were that customer. For years. You felt the friction, the workaround fatigue, the quiet frustration of tolerating a broken system because fixing it wasn't your job.

Now it can be your entire job.

This doesn't mean you skip validation — it means you start it faster. You already speak the language of your future buyer. You can make ten phone calls this week to former colleagues who are still living with the problem you solved — and get more useful feedback in an afternoon than most founders collect in months.

One More Thing

A lot of people reading this have already solved the problem.

They built the internal tool, the training program, the playbook — for their employer. And somewhere along the way they thought: "This should exist as a real product."

That thought is not a daydream. That's market intelligence.

If you built it, you know it works. If your organization adopted it, you've already seen it get traction. The question isn't whether you have an idea — it's whether you're willing to own it.

Real talk: there's no version of this path that's zero risk.

But there's also no version where your decades of pattern recognition count against you. The corporate merry-go-round taught you everything. The problems it gave you? Those are your first product.

Bet on yourself.

Now go launch something 🚀 

You've Spent 30 Years Building Expertise. It's Time to Turn It Into Income That Works for You.

The complete framework for professionals 50+ who want to build multiple revenue streams without quitting their job or betting everything on a startup.

Modern Tools

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That’s why you need mogul. They’re the platform that lets you invest in the same SFRs as institutions for a fraction of the cost. Their founders use the same process they did at Goldman Sachs to identify high-performing properties. 

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Free Knowledge

Here’s a completely different take on your career portfolio. Because, don’t we all have a touch of ADHD? 😉 

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

🤖 AI Report : Target Audience: You don’t need to be technical. Just informed. From Fortune 500 to first-time startups — 400,000 read The AI Report to lead with confidence.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

You are not starting over.

That's the first thing to understand before we get into the list. The word "encore" implies a second performance — something that comes after the main event, smaller and optional. A curtain call. A polite bow before you leave the stage.

Forget that framing entirely.

What most executives call an encore career is actually the most leveraged period of their professional life. You have something most entrepreneurs would pay anything to possess: decades of hard-won pattern recognition, a network built over a career, deep domain expertise in a field, and — if you planned reasonably well — the financial breathing room to be selective about what you build next.

MIT and the U.S. Census Bureau analyzed 2.7 million startup founders and found that a 50-year-old is twice as likely to build a massively successful company as a 30-year-old. A 60-year-old is three times as likely. The average age of the most successful founders wasn't 25. It was 45.

The data doesn't lie. The media just ignores it.

So if you're a senior executive — recently exited, approaching the door, or just quietly wondering if there's a better version of what comes next — this is your list. Twelve real options, each built on what you actually have.

Not what you've lost.

What you've loaded.

Before the List: The One Question That Changes Everything

Before you pick an encore career direction, answer this: What do people ask you for help with that you barely think twice about?

That thing — the thing that feels obvious to you and mysterious to others — is the foundation of everything that follows. Consultants call it your "zone of genius." We call it your uncommon knowledge. And it's the thread that runs through every option on this list.

The executives who thrive in their next chapter aren't the ones who reinvent themselves from scratch. They're the ones who take thirty years of hard-won expertise and point it somewhere new.

• The tools change.

• The leverage changes.

• The knowledge compounds with interest.

With that in mind — here are twelve directions worth considering.

The 12 Encore Career Ideas

1. Fractional Executive

The short version: You do the job you've been doing for decades — just for multiple companies at once, on your terms, at a premium rate.

The fractional executive market has exploded in the last five years. Startups and mid-market companies desperately need CFO-level judgment, CMO-level strategy, or COO-level operations — but can't afford (or don't need) a full-time hire. That's you, a few days a month, at rates that often exceed what you made as an employee.

Who it's for: Executives with a clear functional title and 15+ years in their lane. Finance, marketing, operations, HR, legal, technology.

What it takes: A one-page positioning statement, two to three reference clients, and a professional LinkedIn profile that signals expertise rather than availability.

Realistic income: $5,000–$15,000 per month per engagement. Two fractional clients and you've replaced most corporate salaries.

The honest catch: It's still trading time for money. There's a ceiling. But it's an excellent first chapter of an encore — it generates cash flow and keeps your skills sharp while you build something with more leverage.

2. Independent Consultant

The short version: You solve a specific problem for a specific type of company, packaged as a defined engagement rather than open-ended employment.

The difference between consulting and fractional is specificity.

A consultant sells an outcome. You come in, fix the pricing model, and leave. You audit the sales process and deliver a playbook. You lead a strategic planning retreat and produce a 90-day roadmap.

Who it's for: Executives who have solved the same class of problem multiple times and can deliver a defined result.

What it takes: A clear "I help [type of company] achieve [outcome] through [your methodology]" statement. A handful of case studies. A network willing to make introductions.

Realistic income: Project-based, typically $10,000–$50,000+ per engagement depending on scope. Referrals drive the pipeline once you get moving.

3. Digital Course Creator

The short version: You take what you know — your methodology, your framework, your process — and package it once as a course that sells while you sleep.

This is the most leveraged item on the list, and the one executives most consistently underestimate. The instinct is to think, "Who would pay to learn from me?" The answer, reliably, is: more people than you think, and they'll pay more than you'd guess.

The creator economy has matured past influencers and lifestyle coaches. There is a growing, hungry market for substantive expertise from people who have actually done the thing — and that market will pay $200 to $2,000 for a well-structured course from someone with real credentials.

Who it's for: Anyone who has a repeatable process they've used throughout their career. If you can explain it in steps, you can build a course.

What it takes: A defined topic, a recording setup (a decent webcam and a quiet room is enough), a platform (Teachable, Kajabi, or Gumroad all work), and the willingness to ship before it's perfect.

Realistic income: Highly variable — anywhere from $500 to tens of thousands per month depending on audience size and price point. The magic is in the recurring sales of something you built once.

4. Newsletter Publisher

The short version: You write about your expertise once a week, build an audience of people who share your professional context, and monetize through sponsorships, digital products, or premium subscriptions.

We're slightly biased on this one. But only slightly — because the numbers are real.

A focused, expert newsletter serving a professional niche can attract sponsors who pay $2,000–$5,000 per issue to reach your readers. It can sell digital products at $27–$297 a piece to an audience who already trusts you. And unlike social media, you own your email list. The algorithm can't take it from you.

The executives who build newsletters worth following have one thing in common: they have a genuine point of view developed over decades of being in the room where decisions got made. That's not something a 28-year-old can fake.

Who it's for: Anyone who enjoys writing, has a clear area of expertise, and is willing to show up consistently for their audience.

What it takes: A platform (Beehiiv is my choice), a niche, a consistent publishing schedule, and patience. Newsletters compound. The first six months are slow. Then they're not.

Realistic income: $2,000–$10,000+ per month at meaningful scale. The ceiling depends on how focused your niche is and how aggressively you monetize.

5. Podcast Host

The short version: You create a show around your expertise, interview interesting guests, and build an audience of professionals who share your context.

Podcasting isn't as crowded as it sounds in the niches that actually matter. There are approximately fourteen thousand shows about personal finance for 25-year-olds. There are almost none for the senior executive audience — and that audience listens to podcasts at extremely high rates during commutes, travel, and workouts.

A focused podcast positions you as the central figure in a professional conversation. It opens doors to speaking, advisory roles, partnerships, and product sales that no résumé ever could. A couple of Launch Key subscriber podcast examples were written about in Should you Start a Podcast?

Who it's for: People who prefer talking to writing, who enjoy the interview format, and who have a network of interesting guests to draw from. That last part is where executives have an enormous head start.

What it takes: Basic recording equipment ($200 gets you started), a hosting platform (Buzzsprout or Spotify for Podcasters), and the commitment to produce consistently.

Realistic income: Podcasting is a long game for direct monetization — but an excellent amplifier of everything else you're building.

6. Author and Speaker

The short version: You write the book that distills thirty years of experience into a framework others can use — and then you get paid to deliver that framework from stages.

The speaking circuit for executives with a credible published book is real and well-compensated. Keynote fees range from $5,000 to $50,000+ per engagement for speakers with a defined area of expertise and a professional platform.

The book doesn't have to be a bestseller. It has to be good enough to establish you as the authority on your topic. That's a very different standard.

I’ve highlighted Launch Key subscribers who have done just this in Have you Thought of Writing a book?

Who it's for: Executives with a genuine methodology or framework — and the discipline to write it down.

What it takes: A book (which is two to four months of focused writing and a good editor), a speaker reel, and a positioning page. Industry associations, corporate events, and conferences are the starting point for bookings.

Realistic income: $25,000–$150,000 per year from speaking, with a well-positioned book and active outreach. Ceiling is unlimited for truly in-demand speakers.

You've Spent 30 Years Building Expertise. It's Time to Turn It Into Income That Works for You.

The complete framework for professionals 50+ who want to build multiple revenue streams without quitting their job or betting everything on a startup.

https://launchkey.gumroad.com/l/ffjvdt?layout=profile

7. Executive Coach or Mentor

The short version: You work one-on-one or in small groups with executives who are earlier in their career — helping them avoid the mistakes you already made.

Coaching is the most direct translation of career experience into income. You don't teach theory. You share what actually happened when you were in their position — and what you'd do differently.

The market for executive coaching has grown substantially. Organizations budget for it. Senior professionals seek it out personally. And the credentialing barrier, while real, is lower than it once was — experience and methodology matter more than a certification for most clients.

Who it's for: People who genuinely enjoy developing others and have a track record of leadership that gives credibility.

What it takes: A coaching methodology, some client testimonials, and ideally an International Coaching Federation credential if you want to work with corporate clients. One-on-one or small group, either works.

Realistic income: $300–$1,000 per hour for individual executive coaching. Group programs at $5,000–$15,000 per participant for a structured cohort.

8. Digital Products Creator

The short version: You package your frameworks, templates, checklists, and processes into downloadable products that solve specific, real problems for specific, real people.

This is the most underrated item on the list — and potentially the most passive.

A 20-page PDF playbook that solves a problem you've solved a hundred times in your career. A Notion template for a process you've run at every company you've ever joined. A toolkit that gives someone the output of six months of your experience in thirty minutes of reading. These sell at $27 to $197, over and over, to people who find them through Google or your newsletter or your LinkedIn.

The math is quiet but it compounds. A $47 toolkit that sells three times a week is $600 a month. Ten products and a small audience and you have meaningful passive income.

Who it's for: Everyone on this list. Digital products are not a standalone encore career — they're a revenue layer that sits on top of everything else.

What it takes: An identification of the problems your audience consistently needs solved, the patience to build something useful, and a Gumroad or Teachable storefront.

Realistic income: $500–$10,000 per month depending on product mix, audience size, and volume of offerings.

9. Buy an Existing Business

The short version: Instead of building something from scratch, you acquire a small business at a fair price — and apply your operational and leadership experience to make it significantly better.

Codie Sanchez made this fashionable. But the underlying math has been true for decades: there are tens of millions of small businesses owned by Baby Boomers with no succession plan, and the majority of them will need a buyer in the next ten years. You have the capital, the operational experience, and the network that most of these sellers are looking for in a successor.

Who it's for: Executives with operational backgrounds who enjoy the complexity of running a business, not just advising on it.

What it takes: Access to capital (SBA loans, seller financing, and self-funding are all viable routes), deal flow (business brokers, Acquire.com, local networks), and a clear thesis about what type of business you want to own.

Realistic income: Entirely dependent on the business — but a well-chosen acquisition in the $500K–$2M range can produce $100K–$300K in owner salary plus equity appreciation.

10. Fractional Advisor or Board Member

The short version: You join the boards or advisory teams of startups and growth-stage companies in your industry — providing strategic guidance in exchange for equity, cash, or both.

Your industry knowledge, your network, your pattern recognition for what works and what doesn't — these are exactly what a young company's founders need and almost never have. Advisory board seats are typically compensated in equity (0.1%–0.5% is common for early-stage startups), while formal board seats at established companies carry meaningful cash compensation.

Who it's for: Executives with clear domain expertise in a fundable category — technology, healthcare, finance, consumer brands, logistics — and a network that includes founders and investors.

What it takes: A clear positioning ("I help early-stage healthcare technology companies avoid the regulatory pitfalls that kill most startups in year two"), and active cultivation of your founder and investor network.

Realistic income: Variable. A single successful exit on a startup advisory stake can generate more than a decade of traditional income.

11. Co-Found With a Younger Partner

The short version: You find a hungry, technically capable co-founder in their 20s or 30s — and combine your experience, credibility, and network with their energy, technical fluency, and startup instincts.

This is the model that produces the most successful late-career ventures, but the least discussed. The pairing of deep domain expertise with technical execution capability is nearly impossible to beat. You provide the strategy, the client relationships, and the pattern recognition. They provide the build speed, the social media literacy, and the willingness to sleep less.

The key is honest role clarity upfront. You're not the CEO of the startup you built at 28. You're the experienced domain lead who makes the product credible and the sales possible.

Who it's for: Executives with clear industry knowledge who are honest about not wanting to learn to code or manage a growth team — but who have a real problem worth solving.

What it takes: The right partner, found through a specific search (not randomly), and a clean co-founder agreement from day one.

12. Build a Career Portfolio

The short version: You don't pick one thing. You build a diversified set of two to four complementary income streams that together give you the flexibility, income, and meaning that no single encore career ever could.

This is the option that doesn't make a clean headline — but produces the most satisfaction in practice.

A career portfolio for a senior executive might look like: one fractional client ($12,000/month), a newsletter with one sponsor and two digital products ($3,000/month), and an advisory board seat at a startup (equity, vested over four years). That's a $180,000+ annual income from three sources, none of which requires a commute, a performance review, or someone else's approval to take a vacation.

The portfolio model is more resilient than any single encore path. If one client exits, the others cover the gap. If a product stops selling, the consulting cash flow continues. It's diversification applied to professional life — and it's the smartest move most executives never consider.

Who it's for: Executives who value flexibility over structure, and who are willing to manage a slightly more complex professional life in exchange for significantly more autonomy.

How to Decide

Here's the framework. Answer these three questions and the list narrows itself.

1. How much do you need income to start immediately? If cash flow is a near-term priority, fractional executive or consulting work first. Build products and newsletter in parallel. The portfolio model is the destination, not the starting point.

2. Do you want to trade time for money, or build leverage? Consulting and coaching trade your time for income — and they're excellent. But courses, newsletters, digital products, and equity stakes build leverage. They generate income whether you're working or not. The best late-career strategies combine both.

3. What do people already ask you for? This is the most reliable signal. The encore career that works is almost never the one that sounds impressive at dinner parties. It's the one built on the thing people already seek you out for. Start there.

One More Thing

The executives who struggle in their encore are almost universally the ones who wait for perfect clarity before starting. They want a plan, a guarantee, a validation from someone they respect that this is the right move.

Here's what actually happens: you learn by shipping. The first consulting engagement teaches you what to charge and what to avoid. The first newsletter issue shows you what your readers actually care about. The first digital product tells you whether your packaging matches your audience's problem.

You're not starting from zero. You have decades of evidence about what you're good at and what the market values.

Now go launch something 🚀 

Once you've chosen your direction, read AI Tools for the Non-Technical Entrepreneur →

Every Tuesday morning, Launch Key delivers one practical idea for executives building their next chapter — digital products, AI tools, career portfolios, and the mindset to make it real. 18,000+ subscribers. Free forever.

Subscribe to Launch Key →

Welcome back to the Launch Key ☘️ 

You may not be interested but the speed of change is incredible right now (see today’s Visual Crapshoot real life story).

Over the past 2 months I’m sure I have bored some Launch Key subscribers with my talk of autonomous AI agents. I watched friends eyes glaze over as I droned on at an event that was supposed to be fun.

But I’ve also gotten a fair amount of inquiry from some of you. Have I actually used OpenClaw? Have I deployed other agents? What am I doing personally? And the truth was … not much.

So I set out to change that by building my own small local sandbox - the kind that any of you can do starting today.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Take this week’s poll or comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • Put up or shut up

• Modern Tools

• Old School Wisdom

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

I’ve had one of my email addresses for decades.

And I wasn’t about to let some AI agent clean up 17,000 unread messages from a half-baked solution I cobbled together. I understand the mess of my digital desktop, and am not sure this old dog wants to learn a different file storage system. Plus, I’m not wrangling enough meetings or projects that a Chief of Staff arranging my daily calendar makes sense.

Still, the twitter feeds on my timeline were intoxicating.

People like Alex Finn preaching how one-man companies running multiple autonomous agents are delivering bespoke products, content creation and social media growth overnight. Or Greg Isenberg giving away free startup ideas and playbooks.

You’ve all read as my AI opinion has changed over the past year.

From Mary Meeker’s summer predictions to The Power of One to How to Win When Everyone has AI. I now embrace this as an advantage - especially for late-career folks.

But many of these ideas just involved building way more tech unknowns than I wanted to deal with. I wanted to experiment with non-critical information.

Put up or shut up

I needed to eat my own dog food. Where to start?

I trusted Claude more than OpenClaw and decided to build a small local test that I could manage from a headless Mac Mini in our bonus room. It’s an older machine (Intel i5, 64GB RAM), clean OS install, created an Admin and now multiple users (agents), none connected to my email or calendars or personal data. (I do have another agent spun up that will create, edit and leverage my Notion instance - more on that later.)

I decided on my first use case: create a morning briefing waiting in my inbox from the disparate sources I review most days. Nothing crazy, just a content aggregation play. Markets, weather, crypto, local and national news, opinions, technology, fishing, trends, gear, gadgets and interesting commentary.

Like I said - disparate. But I imagine most of you are the same.

I told Claude I wasn’t a programmer, and it designed and then walked me through building the following open source stack on the Mac Mini : Python, SQLite, Ollama, Claude API, Resend (email delivery), RSSHub (Twitter feeds), launchd (scheduling). It literally took a few hours of copy/paste into Terminal and I had a working model. The whole thing costs $20 a month because I pay for Claude Pro (highly recommend).

I quickly realized that all my various sources would not make 1 brief but instead a big mess. So I organized my thinking into 3 topic buckets:

1. News and Insight

2. Technology and Trends

3. Fishing and Hunting

Naturally, I chose the fishing content to build out my first agent.

I wired up NOAA tide data from my nearest intracoastal station. I use the API from OpenWeather to create daily forecasts. Every morning at 5:45am, the briefing agent creates a localized daily chart like the one seen below complete with best fishing windows.

What hyper-local sources would make the Sportsman really useful? It would be ideal to have locations if local fishing guides shared that info (spoiler alert: they don’t 😉 ).

Another shocker: the outdoor sportsmen and women are not huge twitter posters. Salt Strong creates very good YouTube content, North Carolina Wildlife and the South Carolina Dept of Natural Resources folks post less frequently. There’s a local magazine that puts out monthly fishing reports. I added 8 other content feeds. Once the framework was built it has been easy to add or remove feeds as I find them.

After getting the same story links for a few days, I decided to make a weekly (Saturday morning) full briefing and simply deliver daily tides and fishing overview (example below).

Daily Sportsman example

Finally, I created and iterated a very detailed ‘voice’ for our local guide who knows 3 counties of public game lands (I put actual links in the prompt), as well as all the inland waterways (Myrtle Beach to Wilmington) like the back of his hand. Taught by his father and grandfather, the old boy has forgotten more fishing spots than we’ll ever know. Part of the prompt was that our guide share knowledge in each briefing. The Saturday Sportsman is especially good. My friends thought I was writing all of this commentary.

I have not written one word.

Is this a great use of AI agents? Absolutely not. Do my local fishing buddies find it useful? 100%. And they send me resources and ideas which will make it even better over time. It’s an easy win that I hope puts more fish in the boat.

I’ve also finished creating my daily news and opinion Dispatch. It includes a 3-day local weather forecast, markets update, North Carolina and national news, independent journalists and Twitter feeds. It’s not perfect but its a pretty good start to the morning and points me to which stories deserve more of my time. Plus, the Futurist technology briefing is days away from making it’s debut.

So yes – I have built a personal AI-powered morning briefing system that collects data from RSS feeds, APIs, and Twitter, synthesizes it through Claude, and delivers 3 (soon to be 4) formatted email briefings on a schedule.

Guess what? I bet that you have much better ideas.

Now go launch something 🚀 

Career Portfolio Playbook

If this playbook helps you add even ONE consulting client at $5,000/month, that's $60,000/year. The real question isn't "Is $37 worth it?" It's "What's the cost of staying where you are?"

Modern Tools

A comprehensive guide for addressing the tax talent crisis

A labor shortage in tax is driving the need for a new skill set: one that blends technical tax knowledge with digital fluency.

Automation, AI and data-driven insights now define the role of tax professionals.

This new era of tax is not simply about adopting new tools, it’s about reshaping the skill set and mindset required to thrive in this field. Check out this guide for actionable insights into how to cultivate these skills with your team. See how advanced technologies can help bridge the tax tech gap to increase efficiency, ensure compliance, and drive better decision-making.

Download the guide

Old School Wisdom

Face the facts: before you start building an agent, you should be planning like a Business Analyst. This Emrah Yayici booklet includes tips and best practices to help you start your project on solid footing.

Business Analyst’s Mentor Book

Business Analyst's Mentor Book: With Best Practice Business Analysis Techniques and Software Requirements Management Tips

Free Knowledge

Corey Ganim posted this very good Masterclass on AI Agents for Beginners.

Most people couldn't explain what makes an agent different from ChatGPT if you asked them.

Here's the short version: A chatbot waits for you to ask a question. An agent goes and does the work.

That distinction changes everything about how you use AI in your business.

Here's a full breakdown of AI agents, what they are, when to use them, and how to get started.

Twitter tweet

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀

Last week we introduced The Minimum Viable Exit plan. And why your 18-month exit plan just became 6 months.

This week: An exact timeline. This is a longer-than-normal Launch Key. It includes what to do in each phase. How to leverage AI to move faster. And the psychological preparation nobody talks about.

If you missed Part 1, catch up here.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Take this week’s Poll or comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • Months 6-5 Before Exit: Foundation Sprint

  • Months 5-4 Before Exit: Validation Phase

  • Months 4-3 Before Exit: Pre-Launch Acceleration

  • Months 3-1 Before Exit: Launch Prep

  • Month Zero: The Exit

  • Your AI Leverage Strategy

  • The Minimum Viable Mindset (Speed Edition)

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

The goal of the Minimum Viable Exit isn't perfection.

It's strategic velocity.

You're not building a unicorn. You're building a sustainable business faster than AI makes your corporate job obsolete. Here’s the outline:

Months 6-5 Before Exit: Foundation Sprint

Audit finances in one week. Weekend with bank statements and spreadsheet. What do you need to live? What's on autopilot? Where can you cut?

Build runway aggressively. Cut expenses TODAY. Side project TONIGHT. Sell stuff this weekend.

Test your idea immediately. Nights, weekends, early morning experimentation. Write, edit, hone, create, frame, craft. Find 10-15 hours a week or you're not desperate enough. AI is coming whether you're ready or not.

Leverage AI to test faster. Claude or ChatGPT for landing pages, proposals, content, market research. Weeks become hours.

Months 5-4 Before Exit: Validation Phase

Land your first paying client. While employed. Non-negotiable. Small project, reduced rate—doesn't matter. Prove someone will pay you outside of W2. Use corporate credibility while it's live.

Lock down healthcare. Research,** quotes, decision NOW. Factor real cost into runway.

Build business infrastructure. LLC/S-Corp. Separate bank account. Track expenses. Do this parallel with day job.

Hard conversation time. "Here's the plan, timeline, financial impact, why we can't wait." Get buy-in or adjust.

Months 4-3 Before Exit: Pre-Launch Acceleration

Hit 4-6 month runway. Not there? Extend 2-3 months or tighten survival budget.

Line up first 90 days of work. Quit with revenue in motion. Consulting. Freelance. Cash flow DAY ONE.

AI-powered operations setup. Website (AI builds it this weekend). Email automation. Invoicing. Bookkeeping. CRM. No excuses for amateur infrastructure.

Strategic notice. 2-4 weeks depending on seniority. Leave on excellent terms. Network becomes client pipeline.

Months 3-1 Before Exit: Launch Prep

• Transfer knowledge ruthlessly. Document with AI help. Train replacement. Leave role perfect. Reputation matters.

• Activate network with intention. Share expertise publicly. Create value-demonstrating content. Easy referrals and hires.

• Build AI leverage. Agents, tools, systems. One-person company operating like ten people.

• Plan first 60 days in detail. Who, what, how, success metrics. Don't wing this.

Month Zero: The Exit

Week 1: Strategic rest. Decompress. Light planning. Deep thinking. No execution.

Week 2: Systems live. Workspace operational. Routines set.

Week 3-4: Execute hard. 60-day plan deployed. Client outreach. Content creation. Work delivery.

Week 5+: Iterate fast. Markets shift. AI evolves. Adjust real-time with runway buffer.

The Psychological Shift Nobody Talks About

Money is the easy part.

The hard part? Figuring out who you are when your business card disappears.

NAMI research shows 34% of younger employees and 28% of those 30-49 have considered quitting due to mental health. But leaving doesn't fix everything. It creates new challenges.

The Identity Trap

For 20+ years, "what do you do" had an answer. A title. A company that meant something. That's disappearing.

Month one feels like vacation. Month two feels like freedom. Month three? You'll wake up wondering who you are and if you made a massive mistake. Normal. Plan for it.

Redefine success now. Not "make as much as corporate." That's just a new hamster wheel.

Maybe it's: Working 25 hours with time for your kids. Making 60% of salary but owning your schedule. Building something that matters. Sleeping past 6am guilt-free.

Write it down. Refer back when you start measuring by old metrics.

Support System

Corporate friends might not get it. Find people 2-3 years ahead who've made the transition successfully.

Get a coach, not a therapist. Therapy processes trauma. Coaching navigates transitions. You need someone who can call bullshit when you're thinking about going back for "stability."

Keep one foot in both worlds. Corporate connections stay alive. Isolation kills entrepreneurship.

Your AI Leverage Strategy

This is what makes 2026 different from every previous corporate exit.

Use AI to compress timelines:

• Landing pages in hours, not weeks

• Market research in minutes, not days

• Content creation at scale

• Client proposals customized in seconds

• Financial modeling without spreadsheet hell

Build your AI team:

• Research agent for market intelligence

• Content agent for social media and marketing

• Administrative agent for scheduling and email

• Analysis agent for data and decisions

The tools exist today:

• Claude for strategic thinking and writing

• ChatGPT for research and ideation

• Midjourney for visual content

• Various no-code tools for building without developers

Every week I highlight Modern Tools and in the recent Free To Start issue had a diagram of a potential solopreneur tech stack. Test and experiment to find what works for the way you work.

You're not competing against AI. You're leveraging it to do the work of a team while running solo.

The Minimum Viable Mindset (Speed Edition)

The minimum viable exit in 2026 isn't about having everything figured out.

It's about having enough figured out that you can move fast without being reckless.

• Enough savings you won't panic and take the first bad opportunity.

• Enough clarity you know what you're building toward.

• Enough revenue momentum that day one isn't starting from zero.

• Enough AI leverage you can compete as a one-person company.

• Enough support you won't feel alone when doubt creeps in.

The Real Risk Calculation

Staying: Your job gets automated in the next 12-36 months. You scramble for another role in a shrinking market. You're competing against younger workers and AI agents. Your network has moved on. You're starting from desperation.

Leaving: You exit on your terms. Relationships intact. Credibility high. Enough runway to build something sustainable. You leverage AI instead of competing against it. You use experience as an advantage.

Which actually sounds riskier?

Now go launch something 🚀 

—

** Cobra correction from part 1: A 36‑month COBRA may be possible at the employers discretion. Continuation is especially common when the employee is:

• Within a few years of Medicare

• A long‑tenured staff member

• Part of a leadership or senior role

• Being laid off due to restructuring or budget cuts

Shoutout to Launch Key subscriber Alice A. for forwarding this information.

Career Portfolio Playbook

If this playbook helps you add even ONE consulting client at $5,000/month, that's $60,000/year. The real question isn't "Is $37 worth it?" It's "What's the cost of staying where you are?"

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Works on Mac, Windows, iPhone, and now Android - free and unlimited on Android during launch.

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Modern Tools

Claude Code - Build functional prototypes and tools without being a developer. What used to require hiring a dev team now takes an afternoon.

Claude Code by Anthropic | AI Coding Agent, Terminal, IDE

Anthropic's agentic coding tool for developers. Claude Code understands your codebase, edits files, runs commands, and helps you ship faster.

Free Knowledge

Whether you’re driven by a lifelong dream or recent events, transitioning to entrepreneurship successfully requires careful planning and consideration.

Navigating the Corporate to Entrepreneurship Transition

Embarking on the journey from corporate to entrepreneurship is both thrilling and challenging for small business owners.

CrowdHealth

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀

I bet you’re tired of me banging the same “AI is speeding up like I’ve never seen before” message, so this week I start a 2 part series on your escape plan.

You've spent 20+ years climbing the corporate ladder. Built expertise. Earned your stripes. But if you’re thinking about a ‘someday’ exit, AI has shortened your takeoff ramp. 2026 will be pivotal.

As a result, we need a different playbook.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Take this week’s Poll or comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • The New Math: 4-6 Months, Not 18

  • Building Your War Chest (Fast)

  • Your Homework

• Modern Tools

• Recommendations

• Visual Crapshoot

Pull to Eject

Half of all business exits are unexpected — whether its bots, mergers, downsizing, death, disability, burnout or divorce. Most people aren't planning for change.

And reactive answers create expensive mistakes.

But 2026 just feels different. If you’ve been dreaming about your next thing, you might not have the luxury of waiting.

Microsoft expects 1.3 billion AI agents by 2028. Entry-level positions are disappearing. Middle management is being compressed. Analyst jobs? Gone. Tech may shed another 300k high paying jobs this year.

Your advantages: Decades of relationships AI can't replicate. Pattern recognition from thousands of situations. Credibility that opens doors. Financial reserves for strategic risks. Experience knowing what actually works.

The expiration date: The longer you wait, the more your network forgets your name. Your expertise gets commoditized by AI. Your cushion gets eaten by lifestyle creep.

Your corporate off-ramp is open. But not forever.

The New Math: 4-6 Months, Not 18

In 2023, I'd have said build an 18-month runway. That was stable-world advice.

We're not in that world. You don't have 18 months while AI eats your industry.

Essential Financial Planning for Entrepreneurs: Tips for Success

Master essential financial planning strategies tailored for entrepreneurs and pave your way to success. Read the article to enhance your financial acumen.

82% of small businesses fail due to poor cash flow.

So, a compressed timeline to launch looks more like:

Months 1-2: Deploy immediately. Land 2-3 clients before your business card stops opening doors.

Months 3-4: Rapid iteration. Test, pivot, build systems that do more with less.

Months 5-6: Stabilization. You've found what works. Repeatable revenue. Using AI to 10x output.

Six months is tight. But it's what you've got.

Building Your War Chest (Fast)

J.P. Morgan says build an emergency fund before you leap. Here's the tactical version:

Track for 30 days. Use an app. Get brutal. Real numbers, fast.

Slash immediately. Car wash subscription? Gone. Forgotten streaming services? Cancelled. Gym you actually use? Keep it.

Build 4-6 months survival expenses. Lights on, food, healthcare. That's your number. Times six. That's your runway.

Generate revenue before you quit. Non-negotiable. 1-2 clients lined up. Actual commitments. Actual revenue.

Old advice: Save 18 months then leap.

New advice: Save what you can in 3-6 months while building revenue, then leap with both safety net AND momentum.

I Went Viral for Quitting My Job Because It Was Impacting My Mental Health. Here Are the 4 Things I Did to Prepare for Full-Time Entrepreneurship.

Want to 'fire' your boss? You'll need to be prepared.

Healthcare will be harder to figure out.

Most people don't consider healthcare costs until after they quit. COBRA costs 2-3x your employee rate. For families: $2,000-3,000/month.

COBRA - Full price, exact coverage. 18 months max.

Healthcare Marketplace - Cheaper than COBRA. Income drops = potential subsidies.

Spouse's Plan - Best option if available. Time exit to open enrollment.

Healthcare Cost Sharing - CrowdHealth and Medi-Share: 50-70% cheaper. Community shares costs. No networks, no pre-approvals. Trade-off: not insurance, pre-existing condition waits, faith requirements for some.

Concierge + Catastrophic - Direct primary care ($100-200/month) + high-deductible plan.

Pick before you resign. Factor real cost into your runway.

Your Homework

Next week we’ll detail a 6 month timeline. But here’s your homework for this week:

1. Calculate survival expenses this weekend

2. Open an "Exit Fund" account today

3. Identify one potential client

4. Get real healthcare quotes

The window is open. Just not forever.

Now go launch something 🚀 

Next Week: Part 2 - The exact 6-month timeline. Week-by-week action steps. How to use AI to compress what used to take months into weeks. The psychological preparation nobody talks about.

Make sure you're ready for takeoff.

~ Rob

Career Portfolio Playbook

If this playbook helps you add even ONE consulting client at $5,000/month, that's $60,000/year. The real question isn't "Is $37 worth it?" It's "What's the cost of staying where you are?"

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Modern Tools

One of the biggest sticking points for would-be entrepreneurs is health care. Small businesses have traditionally not had great benefits.

Enter CrowdHealth. Only pay for the health care you need.

After years of paying premiums for health care that I never used - plus a very high deductible - I left for CrowdHealth. Your mileage may vary, but it’s worth your research.

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Become An AI Expert In Just 5 Minutes

If you’re a decision maker at your company, you need to be on the bleeding edge of, well, everything. But before you go signing up for seminars, conferences, lunch ‘n learns, and all that jazz, just know there’s a far better (and simpler) way: Subscribing to The Deep View.

This daily newsletter condenses everything you need to know about the latest and greatest AI developments into a 5-minute read. Squeeze it into your morning coffee break and before you know it, you’ll be an expert too.

Subscribe right here. It’s totally free, wildly informative, and trusted by 600,000+ readers at Google, Meta, Microsoft, and beyond.

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀

Last week included a little travel, good friends, lots of laughs, old haunts, new-to-me technology and plenty of road trip windshield time. And it was all a good reminder of how important it is to recharge.

I needed Sunday drive time just to calm down after the US hockey team’s overtime gold medal. Every angle of Jack Hughes golden goal will be hard to forget! 🇺🇸 

I came back with enough To Do items for the next 3 months. All to improve Launch Key. And that includes more insight from you. See today’s poll at the end of this issue and help direct future content.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

I have always enjoyed windshield time.

I was due for a road trip because I’ve gotten a little stale with Launch Key. The AI agent stuff has been fantastic - and taken a lot of my time to sort. But I’ve fallen into a procrastination routine that lets me write just enough on the weekend to deliver Tuesday’s issue. So I cued up podcasts, made phone calls and let ideas percolate while driving 450 miles generating food for thought.

Sure, I started 2026 busy. But it was simple work, updating all the backoffice stuff to the latest Beehiiv version. So far, those things don’t really show up for subscribers. It’s maintenance tasks that I’ve tricked myself into believing was ‘work.’

I needed to add my own domain, change dns records and email, update my archive to the new version, add Stripe payments, review google keywords, re-rewrite welcome pages and reconstruct a referral program. Many things I haven’t touched in 2 years. It’s like buying new tires for your car. I briefly felt the difference, and then back to the same old routine.

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But recently I’ve had some great reminders about what recharges me. Spoiler alert: it’s not the technology.

First was a longtime friend being in town unexpectedly. His story of corporate layoff is one of the reasons I targeted Launch Key at the over-50 crowd. He’s already had an interesting career portfolio but now he’s free to do something more akin to his passion. Grey-headed solopreneurs armed with modern technology should be a powerful force.

Next was a windshield update call with one of the best coders I know. He is blown away by how good AI coding is and admitted he finished his last project 7 months earlier than expected. But he’s also worried about landing his next remote gig because even mediocre developers look talented with these tools in their hands.

Finally, there was an in-person Launch Key subscriber gathering in Charlotte. People who have supported me for a long time. Good times and bad. Clients, employees, bosses, friends, confidants. Everyone had more important things they could have done. One even showed up on his birthday.

And what did they get in return? Some interesting cross-pollination, a fantastic burrito recommendation and a little Launch Key swag in the form of a trucker hat. What can I say? I’m a cheap date.

Between all the talk about AI - and there was plenty in all my discussions - the human connection is the thing that makes any of these tech choices blossom. Late-career entrepreneurs have a tremendous network advantage and mine continues to propel me.

So, I’m back.

And I’ve got more than a dozen topics I’ve tagged for future issues. I’ve got some clear direction for Launch Key digital products. I’m fiddling with the tech underpinnings. I’ve got a new-to-me Mac Mini reformatting right now for my own AI agent experiments. Oh yeah – I’ve also got some trucker hats if you’re kind enough to forward 10 referrals to the newsletter. 😉 

Most importantly, I have a heart full of thanks for the people in my life who continue to recharge my late-career side hustle.

Now go launch something 🚀 

When Is the Right Time to Retire?

Determining when to retire is one of life’s biggest decisions, and the right time depends on your personal vision for the future. Have you considered what your retirement will look like, how long your money needs to last and what your expenses will be? Answering these questions is the first step toward building a successful retirement plan.

Our guide, When to Retire: A Quick and Easy Planning Guide, walks you through these critical steps. Learn ways to define your goals and align your investment strategy to meet them. If you have $1,000,000 or more saved, download your free guide to start planning for the retirement you’ve worked for.

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Modern Tools

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Free Knowledge

Don’t let the noise drown out the truly important things in life.

Recommendations

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀

If you’ve been reading this newsletter, you understand one of my foundational technology tenants: You don’t need to be first, but being early pays dividends.

There are fantastic AI developments every week now, but we are still pretty early in the evolution. That means there is still plenty of time to experiment, test, throw away and start over.

Your uncommon knowledge can still be the thing that stands out once everyone has AI. But not if you don’t start experimenting soon.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• If you're thinking about your next chapter, start with 12 Encore Career Ideas for Executives →

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • The Time is Now

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

Slowly – then all at once – the AI genie is out of the bottle.

Last week Matt Shumer’s article, Something Big is Happening, (100+ million views) did such a better job explaining what I’ve been struggling with. And it turns out Shumer’s warning against AI was co-written with AI.

The AI world is accelerating:

• 3 years ago, AI was still drawing human hands with 6 fingers

• By 2024, it could explain graduate-level science

• Late last year the best engineers in the world admitted they had handed over most of their coding work to AI

• In the past 6 weeks, 143,000+ users have starred the Github files for OpenClaw - creating personal agents allowing them to 100x their output

• 3 days ago OpenClaw founder Peter Steinberger was hired by OpenAI

• Anthropic and OpenAi both lost key AI safety staff because “the world is in peril”

• Apple Mini’s are on back order

The significance of the Steinberger play should not be overlooked. ChatGPT just grabbed the hottest open source tool and gave it way more resources than they could have imagined.

And that will make it easier for normal people to use.

My X feed has become polluted with AI slop of people trying to sell me their view of how to use today’s tools. They’re already outdated.

My favorite podcasters are trying to make sense of it. And thankfully the big brains are more levelheaded.

Marc Andreessen believes we’re 3 years into a 30 year stretch. In the following podcast he speaks about why AI may finally break a 50-year productivity slump — and what's at stake if America doesn't win the race. He also discusses where value will accrue in the AI stack.

Marc Andreessen: Who Runs the World’s AI?

Podcast Episode · The a16z Show · 02/10/2026 · 26m

The Time is Now

If you haven’t already, you definitely need to start using AI.

And not just as a glorified Google.

The fact that written words are how we communicate with AI (via prompts) means more experienced professionals have a natural advantage. We have decades of well-written communication experience. Leverage it.

Test AI on real world tasks straight from your desk. Give it a messy spreadsheet. Or a complex legal contract. Or ask it to create a logical work flow. Or make sense of a database. Or build a financial model.

Analyst tasks are perfect for AI. Spoiler alert: entry level jobs are already fewer and farther between.

The first answers won’t be perfect. Rephrase the question, iterate and get better results over time. The tools may change, but the people with some experience will get more opportunities.

In just the past month, the opportunity to build a consulting practice has exploded. You don’t even need to be an expert to help people and companies skate to where the puck is going. Mark Cuban thinks AI job creation is the biggest since the internet. People who know how to set up agents and have business savvy will be in high demand. But that window will close as more people become experts.

Really look at your job honestly.

Where are the places that only you can solve problems? Not tasks, but uncommon knowledge you bring to work. Complex relationships, trusted client work, in-person closings etc. Those won’t be replaced by AI.

Add to your moat now, because soon everyone will have AI.

Now go launch something 🚀 

Modern Tools

Ok, so you’re not quite ready for a room of Mac Mini’s? How about an online agent ready to do some work right now? Review your website or twitter feed. Compare to your competitors. Make expert recommendations.

I wouldn’t give it any personal logins but you can absolutely send this rascal on errands to save your time.

Do Anything - Meet Your AI Agent

Meet your AI agent that actually gets work done. Email, browse, call, code, and connect to 3000+ apps.

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Free Knowledge

Sam and Shaan geek out on a few new tools.

This AI agent completes your To-Do list (plus 4 AI tools that’ll…

Get the cheat sheet: 5 AI tools to make your first million https://clickhubspot.com/ybo Episode 795: Sam Parr and Shaan Puri

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

🖥️ Startup Marketer Newsletter - Your cheat sheet for marketing news, insights & tips tailored for the startup space.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

Beehiiv: The newsletter platform built for growth.

Starting a newsletter? Access the best tools available in email, helping your newsletter scale and monetize like never before. Get 20% off your first 3 months of a paid plan, after your complementary 30-day free trial.

Visual Crapshoot

Welcome back to the Launch Key 🚀

Technology is kind of like weather in the south. From a foot of snow to playing golf 5 days later. Change is constant.

The meteoric rise of personal AI agents has been a recent blizzard. The very early days have included huge shifts in thinking. But come fraught with challenges like privacy and security.

It will settle somewhere in the middle but it gives me a chance to write up a longer view article that I’m breaking down over the next few Launch Key issues.

And it starts with the low cost of entry.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

Way back in 2023, a Launch Key foundational concept was that freemium tools like Canva, Notion, Calendly, Gumroad, Wix - allowed a one-person business to do the work of a small agency. Fees applied once you had scale, but hundreds of specialized SaaS applications exist and you could spin your whole thing up for nothing.

Zero cost startup overhead. Useful.

In the last month the tech hype of OpenClaw would have us believe that SaaS tools are a dying breed because now you have your own AI agents building exactly the features you need. Despite marketing and naming snafu’s, the open-source autonomous AI assistant that you can run on your computer has gone viral.

You simply use natural language for every interaction. And can ask it to do things such as conduct research on a topic of your choice, compose a reply to an email summarizing when you’re available for a meeting — or even code up any capability that it doesn’t already have. I touched on it a few weeks ago in The power of one.

Rarely have I seen technology hype explode like these AI agents. It took internet browsing 15 years to reach critical mass. It took smart phones a decade. In less than a month my timeline is filled with ideas about buying Mac Minis to build a farm for your own agent workforce.

The agents found each other online and built their own Reddit-like community with no human interaction. Of course that comes with more than a little concern. The panicans are having a field day.

Anthropic released a set of plugins for Claude Cowork. Not a new model. Not a chatbot upgrade. Plugins.

And within 24 hours, software stocks lost $285 billion in market value.

Relax people. This is just the first version of personal assistants the feels like Jarvis from Iron Man. And while it is pretty cool that you can simply message your personal agent and have them code up solutions, the first versions rarely survive hyper tech growth. Better answers are coming.

Agents are not going to kill SaaS. But they will need to work with it. Today’s best practice startup probably does employ both AI and more traditional SaaS tools. All still free or very cheap to spin up.

And like most of the major tech changes of the past, the best outcomes will come from the best inputs. Garbage in, garbage out. When expertise is applied via new technology quality stands far apart.

• Did PageMaker make everyone a high-end Designer?

• Did no-code tools make everyone a lead web developer?

• Did large language models make all users award-winning writers?

• Will personal AI agents make us all professional coders?

Of course not. The tools improved layman ability but did not make us expert.

The tools are the commodity and they just get swapped out.

Same old story.

The bigger story is possibility.

Inexpensive personal agents give every startup a broader horizon. Professional coders with a deep Github library might just turn out super-human work with agents working around the clock.

You do have the opportunity to build a much bigger business with an army of bots. But only if you think differently. The software only makes the business more efficient. Perhaps hyper efficient in ways never dreamed possible.

I’m happy to be wrong, but my take today is that these types of tools allow the possibility to help create the first billion dollar solopreneur.

So, just like before, there’s never been a better time to start something new.

Now go launch something 🚀 

200+ AI Side Hustles to Start Right Now

While you were debating if AI would take your job, other people started using it to print money. Seriously.

That's not hyperbole. People are literally using ChatGPT to write Etsy descriptions that convert 3x better. Claude to build entire SaaS products without coding. Midjourney to create designs clients pay thousands for.

The Hustle found 200+ ways regular humans are turning AI into income. Subscribe to The Hustle for the full guide and unlock daily business intel that's actually interesting.

Start making AI money

Modern Tools

OpenClaw is a personal AI assistant you run on your own devices. It answers you on the channels you already use (WhatsApp, Telegram, Slack, Discord, Google Chat, Signal, iMessage, Microsoft Teams, WebChat), plus extension channels like BlueBubbles, Matrix, Zalo, and Zalo Personal. It can speak and listen on macOS/iOS/Android, and can render a live Canvas you control. The Gateway is just the control plane — the product is the assistant.

If you want a personal, single-user assistant that feels local, fast, and always-on, this is it.

GitHub - openclaw/openclaw: Your own personal AI assistant. Any OS. Any Platform. The lobster way. 🦞

Your own personal AI assistant. Any OS. Any Platform. The lobster way. 🦞 - GitHub - openclaw/openclaw: Your own personal AI assistant. Any OS. Any Platform. The lobster way. 🦞

Beehiiv: The newsletter platform built for growth.

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Free Knowledge

Startup founders can find many free credits as they bootstrap their new new thing. Here is a partial list of ways to minimize cash flow as you Launch:

• Microsoft for Startups Founders Hub ($5k in azure credits)

• HubSpot for Startups (up to 90% off first year)

• Cloudflare for startups (up to $250k credits)

• Twilio Segment startup program ($50k credits)

• Notion for startups (6 months free)

• Amazon AWS Activate ($1000 credits)

• DigitalOcean Hatch program ($5k credits)

• Posthog for startups ($50k in credits)

• MongoDB for startups ($3k)

• Retool for startups (up to $60k)

• Datadog for startups (up to $100k credits)

• Elevenlabs startup grants (3 months free)

• Linear for startups (6 months free)

• Google Cloud for startups ($2k for early MVP stage)

• Algolia startup program ($10k credit)

• Intercom for startups (90% discount)

• Stripe Atlas partner perks (credits and discounts across tools after incorporation)

• Vercel for Startups (up to $200k in platform credits)

• Supabase for Startups (up to $25k in credits)

• Sentry for Startups (up to $50k credits) GitHub for Startups (GitHub Enterprise free for 1 year)

• GitHub Copilot for Startups (free Copilot seats for eligible teams)

• Figma for Startups (free Professional plan for 1 year)

• Atlassian for Startups (up to $50k credits across Jira, Confluence, etc.)

• JetBrains for Startups (free IDE licenses for your team)

• Brex for Startups (cash rewards, credits, and partner perks)

• Zoom for Startups (discounted or free licenses)

• Canva for Startups (free Pro access)

• Fastly for Startups (CDN credits)

• Loom for Startups (free Business plan period)

• Typeform for Startups (free or discounted plans)

Recommendations

📚️ StoryBound : StoryBound is the first-ever educational storytelling series designed to bridge the gap in finance literacy, career development, and personal growth concepts that the classroom left out.

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

🖥️ Startup Marketer Newsletter - Your cheat sheet for marketing news, insights & tips tailored for the startup space.

CrowdHealth - Healthcare Crowdfunding

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Visual Crapshoot

Welcome back to the Launch Key 🚀

This community started with friends and family and today one of the OGs steps in to deliver an important message about mastery. Steven Shorkey has mastered countless traits with an interesting career portfolio that includes Investment Banker, Creative Writer, Humorist, Storyteller, and Problem Solver.

Throughout our careers we master many things that we may not categorize as ‘important.’ But if we really take stock of our uncommon knowledge, we find many unique pieces that can only be leveraged by us.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

• Modern Tools

• Old School Wisdom

• Recommendations

• Visual Crapshoot

This week’s guest author is Steven Shorkey: a retired investment banker, Steven spends his days immersed in creative writing (novels, short stories, scripts, articles).

Pull to Eject

In the mid-seventies, I jetted off to Belgium to spend eleven months as a foreign exchange student. My new home and school would be in Hasselt, in the Flemish (a spoken-only, dialectic version of Dutch) speaking region of that tiny country.

I was expected to take all of my senior year high school subjects in Dutch. To be clear, I was not a Dutch-speaker upon my arrival. So, in order to keep up with my subjects, I was desperately trying to learn the language. We were told that because of our total immersion—literally every waking moment—we’d become competent in our new tongue in about three months (which turned out to be accurate) and sometime later, fluent.

Hasselt

Sitting in Dutch class one day early in the school year (not a Dutch language class, but one similar to the English class US students take that focuses on grammar, vocabulary, etc.) I could follow along well enough (I should note the teacher never called on me in class, as he presumed I didn’t understand his lectures) to recognize that our teacher was admonishing us to use the proper Dutch word for everyday items that cropped up in our speech, rather than a shortcut version. For instance, in English we often call a woman’s purse her bag when it might more properly be called her handbag.

One example he used was vuilnisbak, the Dutch word for trash can. One would often hear that refuse container referred to as a vuilbak, leaving out the nis portion of the word.

Fast forward to the same class near the end of the school year. I don’t recall the lecture topic, but it involved the teacher constantly turning to write lengthy sentences on the chalkboard (yes, this was the low-tech 70’s). Each time he turned his back, one student—a notorious class cut-up—would stand at his desk and throw a wad of paper at someone across the room, usually hitting his target with a “thwack,” and causing a titter of subdued laughter. Predictably, after several incidents, the teacher feigned his turn toward the board, and then turned back in time to catch the student in mid-throw.

He sternly scolded my friend and insisted he collect the wads of paper and throw them in the—vuilbak.

I immediately spoke up: “Nee, Meneer, hij moet zeker de papieren in de vuilnisbak gooien.” Translation: “No, Sir, surely he must throw the paper in the vuilnisbak.”

Naturally, the class broke into a raucous chorus of laughter: the American correcting the Dutch teacher. The teacher smiled at me and applauded my observation.

It was a lesson I never forgot. Mastery has a way of sneaking up on us.

Throughout our career, we are in the trenches every day, learning how to run and improve our business, and deciphering all the events and factors that bombard us constantly. While there are some obvious ah-ha moments, most days we unconsciously file away lots of information that we refine, expand upon and draw from throughout our careers. It’s easy to believe we haven’t mastered many things in the course of our working life. But that’s seldom the case.

Senior business people have had multiple vuilnisbak moments. Your true value lies in your hard-earned mastery. You know your stuff, perhaps even better than the practitioners you learned from. You have a lot more to offer the business world than you know.

Now go launch something 🚀 

Fast, accurate financial writeups

When accuracy matters, typing can introduce errors and slow you down. Wispr Flow captures your spoken thinking and turns it into formatted, number-ready text for reports, investor notes, and executive briefings. It cleans filler words, enforces clear lists, and keeps your voice professional. Use voice snippets for standard financial lines, recurring commentary, or compliance-ready summaries. Works on Mac, Windows, and iPhone. Try Wispr Flow for finance.

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Modern Tools

One of the biggest sticking points for would-be entrepreneurs is health care. Small businesses have traditionally not had great benefits.

Enter CrowdHealth. Only pay for the health care you need.

After years of paying premiums for health care that I never used - plus a very high deductible - I left for CrowdHealth. Your mileage may vary, but it’s worth your research.

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Old School Wisdom

Robert Greene knows that each one of us has within us the potential to be a Master. Learn the secrets of the field you have chosen, submit to a rigorous apprenticeship, absorb the hidden knowledge possessed by those with years of experience, surge past competitors to surpass them in brilliance, and explode established patterns from within.

Mastery: Robert Greene

The bestseller author of The 48 Laws of Power, The Art of Seduction, and The 33 Strategies of War, Robert Greene has spent a lifetime studying the laws of power. Now, he shares the secret path to greatness.

Beehiiv: The newsletter platform built for growth.

Starting a newsletter? Access the best tools available in email, helping your newsletter scale and monetize like never before. Get 20% off your first 3 months of a paid plan, after your complementary 30-day free trial.

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀

Even more AI agent hype this week as the tech du jour is Clawdbot on a Mac mini to create your first assistant. Stories exploded. And frankly it is a pretty cool concept to text commands to your little tech helper. But it’s also full of security threats.

In reality, technology continues to be a commodity. And our grey-haired wisdom is the secret sauce. Apply it along with cool agent tech? World changing possibilities.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • Your unfair advantage after 50

  • The Energy Management framework

  • Models That Work

• Modern Tools

• Old School Wisdom

• Recommendations

• Visual Crapshoot

Pull to Eject

You all know the hustle narrative: the 4am wake-up call, the cold plunge, the 14-hour grind, posting build-in-public clips. LinkedIn likes and comments tell us this is what success looks like.

If you’re over 50 and looking to launch a business, you might wonder: Do I really need to do all that?

Absolutely not.

Welcome to the anti-hustle hustle — a strategic approach to entrepreneurship that respects your life stage and leverages the wisdom you've accumulated over the decades.

Hustle culture has convinced us that exhaustion equals ambition. What a crock.

Many entrepreneurs proudly declare, "No one will outwork me," only to find themselves burned out and ineffective. We’ve already survived decades of corporate grinding. We know what burnout feels like. Why would we replicate that toxic pattern in our own ventures?

Success doesn't come from working more hours; it comes from aligning effort with purpose. New technology can absolutely fit in here. But on our terms.

Why Hustle Culture is Killing Your Success - ChrisDucker.com

Are you hustling yourself into burnout? Discover why the relentless grind of hustle culture is more harmful than you think. Learn how I transitioned from overworked to balanced success by rejecting toxic hustle and embracing a smarter, purpose-driven approach.

Your unfair advantage after 50

Your body and brain work differently now than they did at 25. This is your greatest asset.

At this stage, you possess:

• Zero tolerance for BS: You can smell a bad opportunity immediately.

• Deep expertise: You’ve spent 25+ years mastering valuable skills.

• Professional networks: You don't need to build trust from scratch; you have decades of it banked.

• Better judgment: You recognize patterns and make smarter decisions faster.

The 25-year-old hustler has to work 14 hours because they are learning everything for the first time. You don't. You can trade speed for strategy.

The Energy Management framework

Forget time management. At this stage, energy management is the metric that matters.

1. Work From Your Rhythms

Stop fighting biology. If you are sharpest at 7am, do your deep work then. If you crash at 2pm, don’t schedule client calls. Build the business around your reality, not an arbitrary discipline schedule.

2. Productize Your Expertise

Don't be a beginner. The 25-year-old startup founder has to learn the ropes. You should simply productize the knowledge you already have. Converting your existing expertise into a business model isn't laziness—it's leverage.

3. Build for Sustainability, Not Scale

What if your business doesn't need to be a unicorn? A venture generating $10K monthly on 20 hours a week might be perfect. Hustle culture worships scale, which often brings the exact corporate complexity you're trying to escape. Choose freedom instead.

4. Leverage Your Network

You have something young founders desperate for attention don't: a Rolodex. One conversation with a former colleague who trusts you is worth more than 10,000 TikTok followers. Mine your network first.

5. Price for Value

When you're young, you compete on price. Now, you compete on insight. Charge premium rates for solving high-value problems efficiently. This shift alone transforms a business from exhausting to sustainable.

Models That Work

Avoid commodity work. Focus on high-leverage models:

• High-leverage consulting: Retainers over hourly billing.

• Digital products: Turn your repeated presentations into courses.

• Advisory roles: Fractional executive work that requires judgment, not grinding.

• Niche services: Solves one specific problem for one specific market.

You don't have to hustle like a 25-year-old to win. You’ve paid your dues. The "always-on" culture is a game for people who lack leverage.

You have wisdom, expertise, and strategy on your side. That is a far better foundation for success than hustle ever was.

So, keep your eyes on the new technology possibilities. But understand the value your wisdom brings to any new venture.

Work with intention.

Now go launch something 🚀 

Need help getting started? 🚀

This step-by-step pre-Launch kit helps you discover and frame up your unique experience and authentic voice. Use lightweight freemium software tools to create a stack that you control. Research links, real life examples and necessary steps gleaned from 30 years of creating innovative digital products. Differentiate before you launch.

Smarter CX insights for investors and founders

Join The Gladly Brief for insights on how AI, satisfaction, and loyalty intersect to shape modern business outcomes. Subscribe now to see how Gladly is redefining customer experience as an engine of growth—not a cost center.

Subscribe now

Modern Tools

Do you pay yourself? Or have your first employee? Do you have freelancers? Or just need help managing all the things related to payroll, taxes and benefits?

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Old School Wisdom

Ryan Crownholm is a serial founder and entrepreneur, mentor, investor, and US Army veteran. But after an almost deadly accident he changed his work perspective. In The Hustle Trap, he shares the principles that helped him build a passive seven-figure income while creating more free time to focus on what matters most.

The Hustle Trap: A How-To Guide for Doing Less and Making More with Your Business

The Hustle Trap: A How-To Guide for Doing Less and Making More with Your Business

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Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀

My timeline has blown up with vibe-coding folks starting 2026 building new products. And while that feeds into the backstory of why this newsletter exists, I’m seeing some excellent personal use cases for AI agents. Focused useful tools that probably won’t get funding but are changing my opinion.

Are you leveraging AI agents? Interesting research? Proof of concepts? Do you see other uses we should cover? Comment below and bring us all up to speed.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Like this content? Forward to folks who can improve our community.

Table of Contents

• Pull to Eject

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

One of the themes that both Elon Musk and Marc Andreessen talk about is how AI will free us all up to not have to work in the future.

And I’ve struggled with that concept.

Maybe it’s my Protestant upbringing or boomer age bracket, but I have a hard time seeing a future where working age citizens only have hobby interests because machines are doing all the so-called work.

Consumers have adopted Generative AI at a never-seen-before pace. The first gen images (remember the 6 fingered humans?) and content slop (sales email, LinkedIn, X, etc) didn’t leave me impressed. I keep updating my opinion as the trend accelerates.

Now that the large language model story has simmered, the growth of agents is the focus.

Microsoft expects 1.3 billion AI agents to be in operation by 2028 – here’s how it plans to get them working together

The tech giant wants to make copilots more agile with a new low-code service to help businesses fine-tune copilots with their own data

My opinion is that corporate is going to have a very hard time - culturally - acting like an agent-powered startup. There are huge governance and security concerns. How will they allow employees to manage hundreds of agents - some they didn’t create? How will employees react to reporting to an agent?

Corporations will get there, but the road is full of potholes.

But individuals? Solopreneurs? Late-career folks? Non-technical founders? Way easier. A team of one can move faster, break things, test something new and deploy this afternoon.

And even if you don’t have a business, agents can multiply your success in a single area of your life. Or just save time allowing you to focus on more important tasks.

Former Y-combinator founder Matt Schlicht shared this idea about wealth agents that make a lot more sense. We all have multiple sources for disparate financial data. The agent dashboard is an idea to handle tasks we all do need to do like shop for insurance, credit cards, or mobile phone deals. But agents can also manage your money and make better real time decisions.

Twitter tweet

Or a home command center where AI agents manage your property. Agents monitor your electrical, plumbing, irrigation systems and schedule maintenance as needed. Agents could also assist in a renovation project and apply for permits.

Or a similar idea for personal health monitoring. Not just your Whoop or Apple watch data, but a personal health command center where AI agents manage your body like you have a full-time medical team.

They monitor your vitals, track your macros, order your groceries, find preventive scans your insurance covers, message your doctors to extract maximum help, analyze your sleep, score your workout form via camera — all while talking to each other in real-time.

Could these types of AI agents free up my time and resources? Absolutely.

Could similar monitors improve a business? Or become the foundation of a new one?

You know the answer.

Now go launch something 🚀 

Modern Tools

Vibecode, powered by Claude Code, lets you build a web app and deploy it to the internet with one click. Build a professional mobile app that accepts payments and ship it to the app store.

Vibecode

Turn your app idea into reality in minutes with Vibecode. The best AI-powered mobile app builder that lets you design, build, and publish apps to the App Store without coding.

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It’s free to set up your company with Gusto. You won’t pay a cent until you’re ready to run payroll. Create a Gusto Account today.

Beehiiv: The newsletter platform built for growth.

Starting a newsletter? Access the best tools available in email, helping your newsletter scale and monetize like never before. Get 20% off your first 3 months of a paid plan, after your complementary 30-day free trial.

CrowdHealth - Healthcare Crowdfunding

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Free Knowledge

Greg Isenberg and Professor Ras Mic lead a beginner-friendly crash course on using Claude Code (and AI coding agents in general) without feeling overwhelmed.

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

🎓️ Daily MBA : Compound Your Knowledge. Join the free Daily MBA community to start receiving daily, 5 minute lessons in Strategy, Finance, Marketing and more.

Visual Crapshoot

Good morning Launch Key 🚀 community!

I hope you’re still working those New Year Resolutions. While I don’t have literal Resolutions, I am a big fan of writing down ideas. You absolutely get more of what you write about (see Human-generated content).

I do listen to big thinkers as they roll out their predictions each year though. Based on my career, the thinkers I’ve listened to most are technology luminaries like Mary Meeker, Marc Andreessen and the boys from the All-In pod.

This week we check in on some of their 2026 predictions.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • AI is the obvious prediction

  • All-In Podcast predictions

  • The Takeaway

• Old School Wisdom

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

I’m not good at predictions.

But I do believe in reading the economic tea leaves and listening to experts to build my opinions. And I’ve shared those opinions with clients, employees and partners for decades. In fact, here’s 36-year old Rob’s 1999 opinion (Common Sense) as we rolled into the 21st century.

History definitely rhymes.

My words from 25-years ago could be repurposed today for all things AI. Eventually any new technology needs to demonstrably improve efficiency, reduce costs or increase sales. The common sense of business ROI rarely stops being sexy.

AI is the obvious prediction

The froth around AI makes it the obvious 2026 prediction. But with hype comes expectations and there are starting to be cracks in the narrative.

In the midst of last year’s AI boom narrative, Michael Burry (made famous in The Big Short) bet against Nvidia, Palantir and Oracle. Time will tell if Burry was a one-trick real estate pony, or if he’s early again – this time with AI.

Marc Andreessen gave a more interesting AI view on this A16z podcast. A technology optimist, Andreessen shares a great 30,000 foot view that the cost of intelligence is collapsing faster than Moore’s Law.

Marc Andreessen's 2026 Outlook: AI Timelines, US vs. China, and The Price of AI

Podcast Episode · The a16z Show · 01/07/2026 · 1h 22m

Truthfully, AI has had boom and bust cycles since the 1960’s. But he believes we are still very early in the game. And unlike the 1990’s internet which included the need to actually build out the infrastructure, 5+ billion potential users already have access in their pocket.

Andreessen is blown away by new AI abilities, ideas and discussions he has with startups. But, he pays more attention to what people do with AI versus what they say. Workers say they’re worried about AI replacing them, but at the same time, millions are actually using AI for daily tasks.

The democratization for AI is unlike anything before.

I spoke with an old friend last week who is grey-headed top-tier code talent. And he admitted that his code skills have been marginalized by less-experienced coders delivering excellent results from AI. And some AI researchers are making more than professional athletes. Those researchers are folks who only gained their knowledge in the past few years. In the early innings of new trends the barrier to expertise is shorter.

Small models can compete.

It’s not just Fortune 500 companies who are winning with AI. Individuals and small groups are changing dynamics. One of the biggest stories of 2025 was Deepseek. It didn’t come out of a large Chinese government-backed company. It was released by a small independent group as open source.

Last week the story blew up on X about AI bots not predictively trading, but taking advantage of slop. The variance in time on bitcoin prices between polymarket and binance is being used to print winning orders.

@CRYINGLITTLEBABY on Polymarket

Check out this profile on Polymarket.

BTC drops 0.3% on Binance. The move already happened. But without real-time data, Polymarket still shows old odds. The down outcome sits incorrectly priced by 30 cents. Bot slams the order. Waits. Window closes. Collects. Not a prediction. A receipt for something that already occurred.

This is simply a technology efficiency play and exactly why my last business was blockchain based. Instant, immutable contracts clean up reconciliation for many types of transactions.

All-In Podcast predictions

These guys get a lot of hate, but you can’t argue with their success. Self-made billionaires volunteering their time, bickering about big picture trends, politics and technology have been right many more times than the average investor.

They review their 2025 business predictions (pretty good track record) and give their opinions for 2026.

• Friedberg thinks Huawei and Polymarket will be a big business winners this year.

• Chamath is betting on copper - still needed for much of the technology we use daily.

• Sacks thinks 2026 will be a huge year for IPO’s - perhaps the biggest in US history.

• Jason is betting on Amazon - because of AWS, increased warehouse robots and same day delivery.

Interesting insights from a very plugged-in group.

The Takeaway

2026 will be as good or bad as other entrepreneurial years. Your product or service needs differentiation and a market. The technology discussed above is important but probably not the main thing. When you’re running your own business you figure out which things really matter. It’s likely not geopolitics, but energy costs and affordable rent. Access to capital and a strong labor pool matter.

There are an awful lot of econometrics adding up to 2026 being a solid year.

The jobs market is not great. So if you have a good job it’s might be better to add AI to it instead of jumping for greener pastures. Start the side hustle.

Growth could be very good. Key interest rate cuts and the ongoing data center boom, coupled with a shrinking trade deficit and increased onshoring, could all converge to boost U.S. GDP growth to 5% – and perhaps even higher.

Earnings are expected to continue to accelerate. Inflation is manageable. Government waste and fraud are being removed. Regulatory restrictions are being cut. Energy costs continue to decline. Tax returns will put more money in almost everyone’s pocket because of the OBBB.

Stir in the 250th 🇺🇸 birthday bash, the World Cup on US soil plus a mid-cycle election year.

The end result? 2026 might just be the perfect time to start that thing you’ve been thinking about.

Now go launch something 🚀 

Old School Wisdom

Are you a business owner or leader who needs a 2026 jumpstart? BGW hosts the Best Year Ever workshop Wednesday January 14. In-person (Charlotte) or Zoom.

Join for a rare morning to slow down, think clearly, and get intentional about what you want in 2026. No noise, no busywork — just space to clarify your direction.

Seats are almost all filled. Signup below:

Best Year EVER 2026

Make 2026 your best year ever

Ship the message as fast as you think

Founders spend too much time drafting the same kinds of messages. Wispr Flow turns spoken thinking into final-draft writing so you can record investor updates, product briefs, and run-of-the-mill status notes by voice. Use saved snippets for recurring intros, insert calendar links by voice, and keep comms consistent across the team. It preserves your tone, fixes punctuation, and formats lists so you send confident messages fast. Works on Mac, Windows, and iPhone. Try Wispr Flow for founders.

Start flowing free

Modern Tools

Do you finally think its time to learn the possibilities of AI? Coursiv has beginner-friendly classes that anyone can understand. No technology background necessary.

Know more than your co-workers in weeks.

Coursiv — AI Courses for Beginners | Learn AI Skills Step by Step

Master AI with beginner-friendly courses. Learn ChatGPT and other AI tools for work and practical automation. No tech background needed. Join 800K+ learners.

coursiv.io/en

CrowdHealth - Healthcare Crowdfunding

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Free Knowledge

I tend to agree with David Friedberg that Polymarket is worth watching. From trending news to sports, crypto, earnings, tech, politics, culture, elections and more. I’m not a degenerate gambler, but Polymarket has insight on trends worth betting on.

Polymarket | The World's Largest Prediction Market

Polymarket is the world's largest prediction market, allowing you to stay informed and profit from your knowledge by betting on future events across various topics.

Recommendations

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Welcome back to the Launch Key 🚀

One of my favorite parts of the holidays is that they include college football bowl games. The time of year when fan bases get a truly honest understanding of just how good this years team is.

Spoiler alert: few are as good as their X-posting fan bases believe.

This year’s bowl season has given us entertaining last second wins as well as blowouts. But it’s also shined the light brightly on coaches and their leadership.

There’s a late-career connection in that many only get their biggest opportunities after years of struggle. So – a little college football fodder for your own startup thinking.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

Everybody is an athletic freak in the NFL, but for me, the college game – despite the taint of NIL, corporate dollars and mediocre NCAA leadership – still represents the best football.

College kids can make phenomenal plays or boneheaded mistakes that turn a game. Coaches have risk and reward moments throughout every game that can cement their future or make them uproot their families … again. It’s crazy good entertainment.

But the best teams all have one thing in common: outstanding leadership.

No one embodies that more than Nick Saban. As a college football coach, Saban won seven national titles (at both LSU and Alabama) and one unclaimed national title, the most in college football history. Saban's career record as a college head coach is 292–71–1. Along with the National titles, he also won 9 SEC titles, coached 4 Heisman Trophy winners and was inducted into the College Football Hall of Fame last year.

Sabans excellence was personally painful as his teams beat my Georgia teams frequently in SEC championships and National title games.

Saban turned his coaching success into premium priced ($250,000) late-career speaking engagements to share his collected wisdom. Aflac, Mercedes Benz, Home Depot, VRBO and other companies pay him to represent their values in advertisements. (see Influencers aren’t a new trend). Corporate pays him willingly because of Saban’s reputation.

But he also left the coaching woodpile far higher than he found it by seeding current programs with his successful program traits. 14 current head coaches including Kirby Smart (Georgia), Steve Sarkisian (Texas), and Lane Kiffin (LSU) all understudied with Saban. Incredibly, this year’s final 4 teams all have former Saban assistants as their head coaches.

Twitter tweet

Not being an Indiana fan, I’ve found the most interesting story in Curt Cignetti - the ‘cocky nerd.’

Indiana coach Curt Cignetti didn’t become a head coach until age 49. Like other late-career business leaders, he didn’t start at the top of the profession. He had good and bad stints along the way that formed his coaching template and leadership style.

He took over a losing IUP program as his first head coach job. He improved them and got his second head coaching job at Elon. He improved them. And then another at JMU. Fifteen years later, he’s leading the undefeated Indiana Hoosiers in their best season in program history.

He learned under Saban, but he’s imprinted the Indiana program with his ideas and culture. And his ideas are very useful for any business owner. His interviews over the past few weeks have given the world a glimpse into what Indiana (and JMU etc) all knew - Cignetti is singularly focused on success. And he is an incredible leader.

Twitter tweet

He is a stickler for not wasting time. Not his players time. Not his coaches time. He teaches in short time periods. 90 minutes is enough. His coaching style is relentless. Surgical. Non emotional. Hyper-efficient.

The culture he has created has not only elevated Indiana football, but just like Nick Saban, it has positively touched hundreds of lives. This year Gignetti’s culture also produced Indiana’s first Heisman Trophy winner, QB Fernando Mendoza.

Twitter tweet

Over the weekend Indiana crushed Alabama 38-3 in the Rose Bowl. The same Alabama that Saban coached to greatness was boat-raced by the old assistant coach. In October, the university rewarded him with a contract extension worth more than $11 million per year. He’s come a long way.

Cignetti learned from the best, but added his own style along the way. And his style won games. A lot of them. Cignetti is now in the company of only a very few best of the best.

He is his own kind of leader. And this week’s reminder to make your own path.

Now go launch something 🚀 

Modern Tools

Do you pay yourself? Or have your first employee? Do you have freelancers? Or just need help managing all the things related to payroll, taxes and benefits?

if you answered ‘Yes’, you need Gusto. Earn $100 VISA card after running your first payroll.

Free payroll software setup in minutes

It’s free to set up your company with Gusto. You won’t apy a cent until you’re ready to run payroll. Create a Gusto Account today.

CrowdHealth - Healthcare Crowdfunding

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Beehiiv: The newsletter platform built for growth.

Starting a newsletter? Access the best tools available in email, helping your newsletter scale and monetize like never before. Get 20% off your first 3 months of a paid plan, after your complementary 30-day free trial.

Free Knowledge

Nick Saban tackles the dangers of mediocrity and shares his secrets to achieving excellence.

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot

Happy New Year Launch Key 🚀 community!

I hope you are all enjoying time with family and friends as we close out another calendar. As much as I have loved having a house full of guests, I do not need any more desserts for the foreseeable future.

But before the Resolutions, a quick review of 2025 for this little newsletter enterprise. It’s been a solid creative outlet for me. But you’ve helped me grow by sending articles, reposting and forwarding issues to your own networks. More importantly, you’ve given me enough positive feedback that I keep working on improvements for the next gen of whatever Launch Key becomes.

So I begin 2026 with two simple words: Thank You.

• Gmail users may wish to read online since some parts may be clipped.

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

• Modern Tools

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

The 2025 Launch Key story has been steady 40% growth.

I started this list with friends and family and an audience of my peers – some of whom had asked for software recommendations. Most were over 50, experienced professionals, bored of corporate, interested in adding something entrepreneurial to their late-career portfolios.

Everyone should have a side hustle.

As many of you know, I started Launch Key as an old guy side hustle and a way to share Creator Economy ideas, links, modern tools and old school business insight. I have long believed that the people were more important than the technology. Still true today.

I believed a newsletter was my best creator avenue because I :

• enjoyed the writing/editing process

• wasn’t sure I could beat the search engine algo’s

• could experiment with content, polls, surveys, ads, etc

• started with a 35-year business network

I chose the new-to-me newsletter platform of Beehiiv.

As 2025 comes to a close, the company sent personalized slides of the year in review. And the few I include here are a good overview of how Launch Key performed.

Consistency wins over time.

I spent a little time most mornings working on content. But it wasn’t perfect consistency because … life. I’m still adjusting to opportunities in our new town. Honestly, I chased more fish and played more golf. I worked around the routine of our blind silver lab. We hosted family and friends and spent time in the NC mountains with mediocre internet access. Writing a newsletter can work around all of that.

Still, these once a week diatribes turned into 50,000 words and 365,000 impressions. And today’s issue marks 119 straight weeks.

I wouldn’t call it income generation, but I took in some advertising dollars from the Beehiiv ad network. I’ve sold a few digital products (Gumroad). I paid for some audience boosts, got boosted by others, worked to clean out unresponsive subscribers and did a mediocre job of reposting on LinkedIn. I can’t control the LinkedIn algo so who knows how much reach that gets.

Thanks to you, email opens and reader engagement is solid.

The year-end takeaway confirms my original premise: anyone can build a newsletter.

Or create a podcast. Or a blog. Or a product. Or write a book. Or start a consulting practice.

At any age.

Here are examples from a few Launch Key subscribers who have done just that:

• So you want to start a newsletter

• Have you thought of writing a book?

• Should you start a podcast?

The tools are affordable. The reach is global. Your uncommon knowledge is the differentiator. You are the brand.

And with just a bit of consistent effort, your audience could fill Red Rocks! 😉 

If you have ideas about creating a digital product or starting something in 2026, then join us and help make the Launch Key community even better.

Comment online. Share your ideas. Send articles. Do you have products or people that I should highlight? Ask questions. I’ll bet that our growing network can help answer them.

Thanks for your support and Happy New Year! 🎆 

Now go launch something 🚀 

Need help getting started? 🚀 

This step-by-step pre-Launch kit helps you discover and frame up your unique experience and authentic voice. Use lightweight freemium software tools to create a stack that you control. Research links, real life examples and necessary steps gleaned from 30 years of creating innovative digital products. Differentiate before you launch.

Modern Tools

I’ve used many email platforms over the past few decades, including both enterprise and individual solutions. I never really loved any of them, until Beehiiv 🐝.

If your business will send newsletters, I can’t recommend it strongly enough.

• They’ve made it drag-and-drop easy and free to start

• They have built-in design tools

• They have a very good recommendation engine for other newsletters

• Their Advertiser network is robust and growing

Each week I get suggestions of companies who want to boost or sponsor my newsletter. I simply choose the ones I think will make the most sense for this audience.

Everything is automated: scheduling, distribution, payments, sponsorships, recommendation engine - all integrated with easy-to-use tools.

Ready to get started?

Click on the link below to save 20% off your first 3 months of a paid plan after a complimentary 30-day trial.

Beehiiv: The newsletter platform built for growth.

Starting a newsletter? Access the best tools available in email, helping your newsletter scale and monetize like never before. Get 20% off your first 3 months of a paid plan, after your complementary 30-day free trial.

Free Knowledge

One of the biggest sticking points for would-be entrepreneurs is health care. Small businesses have traditionally not had great benefits.

Enter CrowdHealth. Only pay for the health care you need.

After years of paying premiums for health care that I never used - plus a very high deductible - I left for CrowdHealth. Your mileage may vary, but it’s worth your research.

CrowdHealth - Healthcare Crowdfunding

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

A big 2026 starts now

Most people treat this stretch of the year as dead time. But builders like you know it’s actually prime time. And with beehiiv powering your content, world domination is truly in sight.

On beehiiv, you can launch your website in minutes with the AI Web Builder, publish a professional newsletter with ease, and even tap into huge earnings with the beehiiv Ad Network. It’s everything you need to create, grow, and monetize in one place.

In fact, we’re so hyped about what you’ll create, we’re giving you 30% off your first three months with code BIG30. So forget about taking a break. It’s time for a break-through.

Start building for 30% off today.

Recommendations

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

🖥️ Startup Marketer Newsletter - Your cheat sheet for marketing news, insights & tips tailored for the startup space.

Visual Crapshoot

Merry Christmas Launch Key 🚀 community!

I hope you all enjoy time with family and friends this week.

The end of the year is a time when most of us take stock, so I’m revisiting a topic you’ve said you liked: Refirement.

In reality, we can refire any time of the year.

Let's get into it.

• Gmail users may wish to read online since some parts may be clipped.

• See also: The Late-Career Entrepreneur: Why Starting After 50 Is a Competitive Advantage, Not a Handicap

• Comment below and let me know if we’re on the right track.

Table of Contents

• Pull to Eject

  • Rewrite Your Narrative

• Modern Tools

• Old School Wisdom

• Free Knowledge

• Recommendations

• Visual Crapshoot

Pull to Eject

There’s a host of blogs and AARP articles about refirement for retirees, but that’s not exactly today’s topic. I’m talking about aiming yourself toward something new you could start while you’re still working.

Work takes far too much time to not enjoy what you’re doing. Sure, in our 20’s everyone needs to grind. But late-career you should able to pick and choose the type of clients and work you prefer.

It’s never a bad idea to review your work.

• What don’t you want to do?

• What can you do better than others?

• What problems do peers bring to you?

• What unique solutions have you created?

• What insight do only you bring to projects?

We all need to be fired up about what we do.

It’s not just work – but relationships, religion, kids, fitness, hobbies, travel, side hustles, creative energy. One of the reasons Launch Key came about was from late-career friends confiding in me that they felt trapped in their corporate gigs.

I first thought about refirement when my Charlotte pastor, David Chadwick started Moments of Hope after being ousted from the previous church he built. His late-career idea created a whole new church model with low overhead, fantastic outreach and organic growth.

Many others have started late-career businesses because of their refirement. Business strategy and supply chain expert Dr. James A. Tompkins founded Tompkins Ventures for just such a reason.

Refirement Beats Retirement Any Day

Refirement beats retirement any day. This alternative to traditional retirement helps you find new purpose and embrace continued growth.

Rewrite Your Narrative

We can do it any time, but typically we get a few windows to completely rewrite our story.

• When our playing days come to an end

• Or we leave for college

• When we start a new job

• Or fail at one

• When we get married

• Or have a child

• When we get fired

• Or move to a new town

• When we start a business

Why not completely change up in our 50’s, 60’s or even 70’s (see Silver Startups)?

Clean out the debris from corporate and do something meaningful – for you. Leverage experience into your new new thing.

I came across this excellent David Epstein substack interview of Steve Magness, about rewriting your whole narrative. Magness’ honesty is refreshing. He made a really bad decision but eventually changed course to align with his values.

His latest book can be found in Old School Wisdom ⬇️ 

Rewriting your Personal Narrative for Growth

You don’t need to rationalize taking a banned supplement to make a radical change. You don’t need to become a whistleblower on the sport you love or deal with public criticism like Magness did.

You don’t even need to move.

It can start pretty small right where you are. The digital opportunities today outweigh all the cost of change and starts with your own list of uncommon knowledge.

I write about the possibilities of the Creator Economy for people of a certain age. You can find a few examples below.

• Attention is the new oil

• Human generated content

• The anti-IPO plan

Sometimes a change of scenery does help though. My own move late last year has given me new neighbors with new insights and plenty of new ideas.

But to my friends who have wondered – yes – it is more like a Refirement Community.

Now go launch something 🚀 

7 Ways to Take Control of Your Legacy

Planning your estate might not sound like the most exciting thing on your to-do list, but trust us, it’s worth it. And with The Investor’s Guide to Estate Planning, preparing isn’t as daunting as it may seem.

Inside, you’ll find {straightforward advice} on tackling key documents to clearly spell out your wishes.

Plus, there’s help for having those all-important family conversations about your financial legacy to make sure everyone’s on the same page (and avoid negative future surprises).

Why leave things to chance when you can take control? Explore ways to start, review or refine your estate plan today with The Investor’s Guide to Estate Planning.

Download your free guide now!

Modern Tools

Do you hire freelancers? Or have your first employee? Or just need to help managing all the things related to payroll, taxes and benefits?

if you answered ‘Yes’, you need Gusto.

Free payroll software setup in minutes

It's free to set up your company with Gusto. You won't pay a cent until you're ready to run payroll. Create a Gusto account.

Old School Wisdom

Striving is in our nature. We all want to perform at our best when it matters most.

Renowned performance scientist and bestselling author Steve Magness reveals a new path to sustainable success. In Win the Inside Game, Magness argues that excellence and fulfillment are not mutually exclusive; we can and should seek both.

Win the Inside Game: How to Move from Surviving to Thriving, and Free Yourself Up to Perform: Steve Magness

Magness draws on his vast wealth of experience as an Olympic coach and whistleblower, highly popular consultant, and premier expert on performance, as well as scientific findings, interviews, and case studies, to provide a three-part framework to help us learn to focus on what really matters and achieve success.

Need help getting started? 🚀 

This step-by-step pre-Launch kit helps you discover and frame up your unique experience and authentic voice. Use lightweight freemium software tools to create a stack that you control. Research links, real life examples and necessary steps gleaned from 30 years of creating innovative digital products. Differentiate before you launch.

CrowdHealth - Healthcare Crowdfunding

Tired of health insurance policies that are confusing and expensive? Join CrowdHealth and finally break free from the insurance system. CrowdHealth is not health insurance. It's an innovative model to use and pay for health care without insurance middlemen and government influence.

Free Knowledge

Five Steps to Reset Your Career | For Professionals in Career Transition — The Leadership Coaching Lab

If you've reached a point where your career no longer sparks joy (or even a flicker of interest), try the RESET method described in this post to navigate a courageous journey towards a more fulfilling career.

Recommendations

🖥️ Startup Marketer Newsletter - Your cheat sheet for marketing news, insights & tips tailored for the startup space.

💼 Thriving Freelance - Gigs and Growth : Hundreds of job opportunities sent directly to your inbox each week, plus timely resources to support you as you grow and evolve.

📕 MGMT Playbook : Practical management insights straight to your inbox every Wednesday.

🗃️ Dealroom Business Success Uncovered : Learn directly from billionaire entrepreneurs on how to grow a business. Join a community of 2,000+ innovators.

Visual Crapshoot