Hi {{ first_name | there }},

Happy new year! In 2026, I'm writing more about becoming an AI-fluent knowledge worker. You can expect our editions to be 70% practical, 30% meta.

Today, in 10 minutes or less, you’ll learn:

• 👻 Why "PhD test passing ghosts with adolescent-like cognitive abilities" perfectly captures today's AI tools

• ⚡ How I'm leveraging LLMs to design UI, write SQL, and fix bugs as a generalist

•  🔥 What finally made work feel magical again after feeling stuck and uninspired

🚀 Live Workshop: Claude Code for Non-Coders 101 (RSVP)

Learn how to build reusable AI workflows with Claude Code slash commands - no coding required.

I'll demo my actual content and event automation, then we'll build your first command together.

What We'll Cover

• Live demo: My slash commands for newsletters, workshops, and events

• Hands-on: Build your first slash command for a task you do weekly

• Q&A: What works, what doesn't, and how to iterate

Who It's For

• Knowledge workers who want to automate repetitive tasks

• Anyone curious about AI agents but unsure where to start

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

👨‍💻 How I'm using agentic tools in January 2026

In the past month, multiple business owners told me AI keeps them up at night.

To start, I'm blown away by last year’s LLM advancements. I have written about using tools like Claude Code and Relay to do things in minutes that would’ve taken me days before - like synthesizing user research. I’ll share more examples later.

On the other hand, countless media outlets predict the death of knowledge workers (which they also did 10 years ago. Hmm). Many of my peers have admitted feeling afraid of losing their jobs or being replaced by technology. And who can blame them?

I'm a knowledge worker too. Everything feels like it’s changing.

I don't know what the future will bring, but I try to focus on what's in my power to shape my own future.

One thing I’m doing is obsessively learning and practicing new technology. Leading with curiosity. I treat it a bit like a game.

My current learning agenda: trying to get more out of agentic tools like Claude Code and Cursor.

LLMs are powerful, but also finicky and unreliable. Andrej Karpathy, former OpenAI co-founder, had this sticky line where he describes LLMs like ghosts that can pass PhD tests but still possess adolescent-like cognitive abilities.

Not the AGI we all expected.

My hope is that by pushing the boundaries of the edge tools habitually, I can figure out how to best apply them to interesting problems. Like wiping the fog off the window just enough to catch a clearer glimpse of the future.

Here are four ways I'm leveraging agentic tools to accelerate my work:

1/ Filling in gaps as a generalist

The 2010's were defined by technical specialists.

Information asymmetry and domain knowledge scarcity meant specialists led organizations, commanded high salaries, and found themselves in high demand.

In the late 2020's, we can now use LLMs to quickly fill our knowledge gaps faster than ever before. We’re one step closer to being like Neo instantly uploading kung fu skills in the Matrix.

Let’s take vibe coding. Yes, there’s quality issues, but I’m increasingly seeing non-technical friends building productive apps for their work. The inverse is also happening - I see more engineers filling the gaps of product/business people in small teams.

15 years ago, Chris Dixon said, "The next big thing will start out looking like a toy." (which he borrowed from Clayton Christensen).

I think we're seeing it here too.

How I'm implementing this:

In my pod, I'm filling in the gaps wherever possible to relieve bottlenecks:

• When our designer was still deliberating her offer, I stepped in to design a few UI/UX flows to unblock development.

• When our engineers were heads down on crucial tech milestones, I fixed bugs myself and submitted PRs for review.

• When our firm needed to automate reports, I wrote the SQL queries instead of waiting for us to hire a data analyst.

Charles Munger, famed investor, lamented often about how our top educational institutions failed to train our grads in interdisciplinary thinking.

In this era, working across disciplines is not a luxury, but a necessity.

2/ Delegating repetitive work

Learning how to automate the energy-sucking parts of your job is becoming table stakes.

Take doc-writing for a traditional product manager.

Writing PRDs, planning docs, tickets, specs, and Slack messages used to consume dozens of my hours every week. And I’d still be drowning in more work.

Today, writing docs and Slack messages is 3x-10x faster. Notion AI helped, but setting up Claude Code slash commands + Notion MCP led to a much greater lift for me.

As a result, I freed up more of my time to interface with portfolio firms, problem-solve, and prototype/validate my ideas. (the fun stuff!)

How I'm implementing this:

Prototyping used to be something I only got around to once in a blue moon.

I remember at Dropbox a decade ago, I depended on my designer to create UI mockups for customer feedback. But they were so busy, we only did it once a month at our best.

Contrast that to now: I can whip up a prototype, deploy to Vercel or a staging server, and get client feedback in 1-2 days.

Here's a subset of the tasks I'm delegating to Claude Code, Gemini, etc.:

• Writing SQL queries

• Synthesizing research

• Making presentation graphics and slides

• Debugging code

• Drafting PRDs and specs

• Creating prototypes

The list keeps growing every week.

Testing image gen using Nano Banana MCP

3/ Investing upfront time in context scaffolding

I’ve realized the quality of my AI output is directly proportional to the quality of my input.

Garbage in, garbage out.

However, if I input structured context, the output quality is wildly better.

I'm now spending more upfront time collecting, organizing, and structuring context than before.

This feels a bit counterintuitive - shouldn't AI reduce my task checklist? But I think of it like onboarding a new employee. You need great onboarding for them to ramp up faster.

How I'm implementing this:

I’m obsessive about creating a "data layer" that feeds my LLM tools:

• Notion as a knowledge base - We use Notion at work, and I use it for Portfolio Path too. Every meeting note and project doc lives here. I then use Notion AI as a chief of staff to surface what I need. When I need Claude to help with a coding/writing project, I can use Notion MCP to feed Claude the full context in seconds.

• Structured templates - I've created templates for common documents (PRDs, specs, retrospectives). The structure makes it easier for AI to parse and generate consistent outputs.

• Voice notes → transcripts → organized notes - I capture ideas via voice, transcribe them, then organize into my knowledge base. This raw material becomes fuel for Claude to help me create content briefs and outlines.

This has shifted my mental model:

I'm not just picking up new AI tools. I’m building personal data scaffolding that gives these tools significantly more leverage.

It's like the difference between asking a new hire to do something before vs. after they’ve onboarded properly. Same skills, but vastly better results.

My Notion content calendar is context scaffolding.

4/ Practicing meta-skills differently

Data fluency, management, communication, and learning to learn.

These skills matter more than ever. But they don't look like how I viewed them traditionally.

How I'm implementing this:

Data fluency - This used to be about basic data analysis, Excel, and reporting. Now it's about setting up context scaffolding to feed into my LLMs and agentic tools. I spend more time organizing my knowledge base (Notion, markdown files, project READMEs) than creating excel analyses.

Management - This used to be about hiring and building a large team. Now it's veering towards managing the AI/agentic tools I have to scale my team's output.

Communication - This used to be about communicating up, down, and sideways in complex cross-functional situations. Those situations still exist, BUT I also have to master LLM prompting and context engineering to get the results I want.

Learning to learn - The most meta skill. This used to be about learning one skill intensely in a continuous stretch of time. Now I'm learning a skill enough to clear bottlenecks before switching to what's demanded by the next bottleneck.

Admittedly, this feels a bit like a dance right now. It started off feeling random, but gradually picked up on the coherent rhythm and pattern behind the movements.

The most important thing I’ve discovered

I know I've talked a lot about output and productivity.

But the most important part about all of this isn't what I'm doing, achieving, or even learning.

It's that I'm having more fun with work than recent years.

As a kid, I was obsessed with using new web technologies for the first time. It felt magical. Like seeing into the future.

25 years later, I feel like I've rekindled some of that spark I had from my first web impressions.

Candidly, before this, I was feeling hesitant about working in the tech industry again. It started to feel a bit repetitive and uninspiring.

But for now, I'm having a great time. I hope it'll last for a while.

In Summary

Here are four ways I'm using agentic tools in January 2026:

1. Becoming a generalist - Filling knowledge gaps with AI to relieve bottlenecks (design, code, data)

2. Delegating to automation - 3x-10x faster docs, prototypes in days not weeks, growing task list for AI

3. Investing in context scaffolding - Building a personal database (Notion, markdown, templates) that makes AI tools higher leverage

4. Refining meta-skills - Data fluency, management, communication, and learning to learn - but done differently for the AI era

These edge tools are still finicky. Ghosts that can pass PhD quizzes, but possess elementary student like cognitive abilities.

But by using them daily, I can wipe the mist off the window just enough to catch a clearer glimpse of the future.

P.S. Thanks for reading! Are you using agentic tools in your work? What's working, what's not? Reply and let me know.

💎 Last Week’s Gems

• Foundations: My 1999 (and part of 2000) (Michael Burry)

• Is it a Bubble? (Howard Marks)

• AI tools are overdelivering: results from our large-scale AI productivity survey (Lenny Ratchisky & Noam Segal)

• 6 Surprises From 2025 (Ben Carlson)

• Australia Just Kicked Kids Off Social Media. (Is the U.S. Next?) (Cal Newport)

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

I’m back after a busy month moving from Mexico City to Singapore (and work trip to London).

It’s also been an exciting month for AI product launches!

Today, in 10 minutes or less, you’ll learn:

• 🎨 The AI tools that just gave you illustration and slide design superpowers

• 🔍 Why NotebookLM beats other AI document tools for research workflows

• 📊 How to transform meeting transcripts into professional presentations instantly

SPONSORED

🖋️ 2025 Year in Review Workshop

Before we sprint into the new year, let’s pause for a moment of reflection — to take stock of how far we’ve come, what we’ve learned, and what we want next.

Join us for an energizing 45-minute session designed to help you reflect on your 2025 portfolio journey and start shaping your roadmap for 2026.

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

📗 NotebookLM builds my slide decks now

I hate creating slides.

I’m writing this as I fly from London back to Singapore after visiting our portfolio accounting firm for the first time.

On this trip, I showcased a product demo and created slides using Canva, my go-to presentation tool for the past 3 years. 

Even though Canva sped up slide creation, I still spend way too much time tweaking font sizes, dragging-and-dropping rectangles, and aligning layouts.

That’s why my mind was blown when I tested Gemini 3, Nano Banana Pro, and NotebookLM’s Slide Deck.

🗺️ My AI journey milestones

I’ve personally had a few AI magic moments that transformed how I work:

1. My first ChatGPT conversation

2. Using my first AI meeting transcription + notetaker

3. Writing my first newsletter using Claude + training data

4. Coding my first app using Cursor/Claude Code

5. Discovering AI voice dictation

Now NotebookLM Slides and Nano Banana Pro.

📚️ How I’m using NotebookLM

Google describes NotebookLM as “the AI research tool and thinking partner that can analyze your sources, turn complexity into clarity and transform your content.”

I’ve been busting out NotebookLM several times per week at work:

• Synthesizing over 20 research calls on a similar topic

• Creating summary Slack messages for our team standups/syncs

• Conversing about a research-backed idea or concept quickly

In terms of my research workflow, I’ve found it superior to other tools:

First, it’s seamlessly integrated across Google Workspace. Since my employer is using Google Workspace, I can record Google Meets and then easily import transcripts into NotebookLM.

Additionally, NotebookLM excels at citations. I reference quotes and citations very frequently in my research, so this characteristic puts it ahead of other AI document tools for me.

Here’s an example report I generated from importing my recent “AI for professionals” newsletter editions:

However, now with Slides, NotebookLM has gone from useful tool to potentially must-have workflow.

From the same newsletters earlier, I generated these slides:

Honestly, this output is higher-quality than what I do on my own.

It feels a bit like magic.

But given my experience with unpredictable AI tools, I remain skeptical.

Next, I’m going to test NotebookLM rigorously for various use cases.

Like my recurring meeting workflows:

1. Record meetings transcripts and video

2. Import meeting transcripts

3. Generate summary snippets for Slack/email/etc

4. Add additional dot points for next meeting

5. Generate Slides for next meeting

I’d love to get to a point where I’m fully hands-off for recurring meeting communications - aside from planning agenda for next meeting.

Things to keep in mind as you’re playing around with NotebookLM:

1. Start with research or ideation use cases - In my experience, NotebookLM is stronger than other models for these use cases.

2. Start with good source material - NotebookLM is only as good as the content you feed it. Garbage in, garbage out.

3. Tailor with a last-mile prompt - You have the option to customize by using your own high-level outline, strategy, style, or dot points - which will help you get closer to your desired output.

🍌 Bonus: Nano Banana Pro

Nano Banana Pro is Gemini 3’s image generation and editing model. It’s available for Google Workspace customers in Google Slides, Vids, Gemini, and NotebookLM.

The output quality is insane. Night-and-day vs previous image models. 

Here’s an illustration I generated from a one-shot prompt:

Visuals are now table-stakes for communicating ideas.

I’ve always wanted add entertaining illustrations in Portfolio Path newsletter and my work docs - but simply got too lazy.

Finally, with Nano Banana Pro, I have no more excuses!

In Summary

NotebookLM is fundamentally changing how I approach my operational workflows.

While it’s still early days, I can already see how slides that used to take me 2-3 hours to build now takes ~15 minutes.

And the quality is often better than what I'd create manually.

The barrier to creating professional-quality outputs keeps dropping.

Five years ago, you needed design skills to make decent slides. Today, you need good input data and a lightweight prompt. But that’s about it.

I suspect in another five years, even customizing the prompt won't be necessary.

The future is bright.

P.S. What workflows have you used NotebookLM or Nano Banana Pro for? Hit reply and let me know.

P.P.S I’m hiring full-stack software engineers - DM me if the roles below sound interesting:

1. Product Engineer JD (Singapore/South East Asia)

2. Product Engineer JD (Cantonese-speaking, Singapore/HK)

💎 Last Week’s Gems

🚂 The Railway Bubble vs. the AI Bubble (Ben Carlson)

⚙️ Agentic Workflows Explained (Department of Product)

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

We have only 3 weeks left in Mexico City, before we’re off to Singapore. Wow, that’s fast!

Today we’ll cover one of my favorite new discoveries: Notion AI ✨ 

In 10 minutes or less, you’ll learn:

• ⏰ 5 specific workflows that transform busywork into strategic thinking time

• 🎯 Real examples of AI handling research synthesis, task management, and content extraction

SPONSORED

🤓 Stop drowning in admin (let Notion AI handle it)

Drowning in scattered notes, endless to-dos, and research that lives in 47 different places?

Join us for a hands-on workshop where we'll leverage Notion AI into your personal chief of staff.

What we'll cover:

🗂️ Building a centralized research repository that actually works
⚡ Auto-generating planning docs and project briefs in seconds
🤖 Automating task management updates so you can focus on real work
💡 Extracting insights and patterns from your data

Perfect for professionals, founders, and portfolio careerists who are tired of admin work eating their best hours. No technical skills needed.

Join us:

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

🛠️ How I use Notion AI as a chief of staff

I used to waste hours writing docs that gathered dust in Google Drive.

Admin work as a PM was kinda the bane of my existence. At its worst, I felt like a glorified Slack and Google docs monkey. 🐒 

Unsynthesized client calls would pile up in Google Docs. Research insights would get buried in an obscure corner of my Dropbox. Tasks would get lost in the shuffle.

At some point, the constant busywork killed some of my excitement for the role.

That’s when I discovered how Notion AI can become my chief of staff to reclaim hours per week from busywork.

And how anyone reading this can do it too.

In this edition, I'll show you exactly how I transformed my workflow by “hiring” Notion AI as my chief of staff - not just another documents tool.

📝 From busywork to fulfilling work

Last month, I had 17 client research calls in 2 weeks. I wanted to map out UX workflows, synthesize into research, and draft planning documents.

The old me would have spent 7-10 hours per week just organizing notes, writing summaries, and drafting initiative plans.

I loved talking to customers, but the busywork that followed often felt slow and painful.

The new me fortunately lives in 2025, where we have a gazillion new AI and automation tools at our fingertips.

Since September, Notion AI was one I’ve adopted a lot - which surprised me.

Frankly, I’m a heavy Notion user, but the AI features were lackluster up until the fall. I could use Notion AI to edit a single page, but only get mediocre results.

But then they launched Notion 3.0 with Agents. Now the AI agents can work across the entire workspace and databases, and the output feels like 2x-3x higher quality.

I’ve found myself go from barely touching Notion AI to using it daily.

Twitter tweet

🤖 How I built my AI chief of staff

Notion has a Notion AI link in their main menu. If you click it, you’ll see their equivalent of a ChatGPT/Claude home screen.

The first steps:

1. Setting up the AI personalization

2. Linking Notion AI to my email, Slack, and files to ingest context

This is the agent identity I setup for my Portfolio Path workspace (it might look familiar):

Setting up the connectors was also easy, although I’ve yet to leverage them fully. I’ve mainly used Notion AI within the workspace.

Here’s 5 things I’ve used Notion AI for:

🗂️ 1/ Synthesize a centralized research repository

I dump everything from client calls into one Notion page, let’s call it “Research Notes”:

• Meeting transcripts and AI summaries

• Screenshots from client calls

• Competitive research

• Random thoughts and observations

I’ve liked putting everything in one view so I don’t have to click to see more. I can just scroll.

You can use a database for more organization.

One pro of doing this is Notion AI is now good at referencing source pages - so if you have meeting notes in separate pages, it’ll link the citation:

Later, when I want to leverage this “Research Notes” page, I just have to tag it @Research Notes:

Now let’s walk through how I translate these insights into actual initiatives:

⚡ 2/ Generate planning documents in minutes

First, I’ll setup a planning doc template. I like to write section headers and short descriptions to describe what goes into each section to help guide AI (much like guiding a human).

Here’s examples of sections I have in my template:

Then instead of staring at the blank template, I write quick bullet points in the appendices:

• Key problem statements

• My hypothesis

• Proposed solutions and components

Then I input this prompt into Notion AI:

The key is creating contextual sources and tagging them appropriately in Notion AI - so it doesn’t run out of context window searching for the most appropriate source.

In my work, I’ve setup context using:

• Research Note docs like above

• Discovery board/database with initiatives organized by theme

• Task tracker database

• Team knowledge base docs

For example, here’s an output I generated for planning my Notion AI Workshops with citation links.

It’s not bad as a first pass, but could be even more useful if I ask the AI to include specific quotes from these meeting transcripts:

After I generate the first draft, 99% of the time I edit manually and/or refine through continued prompting.

Typically I’ll take one of two paths:

• 0% to 60% of the way there → I continue prompt

• 60%+ of the way there → I’ll edit

Still this means adding somewhere between 5-30 minutes, for what used to take me hours to write manually.

✅ 3/ Automate task management updates

I used to constantly forget to create or check off tasks. I always wished this set of work could be automated.

Finally, it can!

Now I just ask Notion AI to do it:

It scans my completed work based on timestamps, updates task statuses, and keeps my personal task board current.

For example, my team has a running Standup Notes document.

So I have Notion AI ingest this document’s context to check off and add tasks to my personal task board.

This is super helpful especially if I’m feeling wiped out at the end of a busy day and can’t recall what I exactly did (that ever happen to you?).

🔍 4/ Review and extract content

Every newsletter I write now gets auto-reviewed against my writing checklist:

Also instead of manually hunting for great quotes or insights from the newsletter, I ask Notion AI to extract quotes/images/insights from the newsletter and drop it in the appendices for my future writing.

This helps me automatically build my content library.

📊 5/ Automate database creation and updates

I used to dread spending couple hours every week keeping my project boards up-to-date, but now it’s a quick and painless task.

I ask Notion AI to propose new initiatives to create database items for, then I’ll review the ideas before it creates the rows.

What’s really powerful is using it to auto-complete complete/update database fields like:

• Statuses

• Tags

• User Stories

• Calculations

You definitely need sufficient context, but I’ve found it works to get each row to a good spot, then I’ll review and edit minor issues in a few minutes.

📈 The compound effect

These small workflow changes unlocked the work I actually wanted to do.

Instead of spending 7 hours I used to spend on overhead, I can spend them with clients, diving into their biggest pain points. Instead of rushing through the research synthesis to get to "real work," I can go on a walk and think through patterns I otherwise would’ve missed.

I feel less mentally taxed from the busywork, so I can think about the hard problems and trade-offs more clearly.

I’m less likely to be a bottleneck for my team’s workflows. And ultimately, I hope this helps clients get valuable solutions in their hands faster.

What this means for your portfolio career

Most people use AI tools for isolated tasks. Write an email. Draft a Linkedin post.

That's thinking small.

The real opportunity is building systems where AI removes the work that drains you, so you can focus on work that energizes you.

Here are the five use cases we walked through:

1. Synthesize a centralized research repository

2. Generate planning documents in minutes

3. Let AI maintain your task statuses

4. Review content systematically and extract reusable insights

5. Automate project board creation and updates

Remember whether you're working full-time or building your own business - your competitive advantage isn't how fast you can write status updates.

It's your ability to solve complex problems and build meaningful relationships with clients.

Now go forth and hire your own AI chief of staff!

Thanks for reading. If you’re interested in setting up Notion AI as your chief of staff, I’m hosting a free upcoming workshop on this topic. Join us!

💎 Last Week’s Gems

• Are Millennials Doomed? (Nick Maggiulli)

• Why AI Will Widen the Gap Between Superstars and Everybody Else (WSJ)

• Letter to a Young Person Worrying About AI (Commoncog)

🤩 Community Spotlight

Here’s what our members have been up to in the past 2 weeks:

🍱 Li Si sent her first invoice for mentoring Singapore companies on Australian market entry and celebrated with Japanese dinner

🤝 Betty received a surge of mentorship requests, reminding her how much she loves giving back to the community

💪 Jenny signed another coaching client and got strategic about saying "no" to misaligned project proposals

🚀 Deassy completed 135 offline in-depth interviews in just 2 months (compared to agencies doing 15 online interviews in 1.5 months) and built a new human-AI research workflow

📝 Nishant posted daily on LinkedIn all month while managing an infant, plus lined up a ghostwriting package with an AI founder

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

With the new tools available, it’s easier than ever to steer your career ship. 🚢 

Today, in 10 minutes or less, you’ll learn:

• 🎯 How I stopped waiting for my manager to notice my potential (and started driving my own growth)

• 🗺️ The 4-part framework that turns vague aspirations into concrete proposals

• 🤖 How to build an AI copilot that preps you for career growth conversations

SPONSORED

🤩 Join the Portfolio Path Community

Tired of navigating your portfolio career alone?

If you have 5+ years of working experience and are building a portfolio career, apply to join our invite-only Portfolio Path Membership

• 🚀 Why join the community: Accelerate your learning, grow your revenue, and build genuine relationships with like-minded peers on the portfolio path—so you can go further together than solo.

• 🎯 What you get: Monthly community calls, expert fireside chats, 30-day challenge, accountability buddies, and shared resource library.

• ⏰ Why now: Early members lock in founding member perks and the best lifetime rate.

We can't wait to meet you!

Limited November 2025 spots available.

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

💬 How I prep for career growth chats using AI

"Where do you see yourself in six months?"

Your manager asks you out of the blue. You freeze.

That feeling of being caught unprepared :*(

You know you want more. More scope, more complexity, maybe a different direction entirely.

But how do you articulate that without sounding unfocused or entitled?

Here's the thing most people miss about career growth.

It's not about waiting for your manager to notice your potential. It's about driving your own growth autonomously with clarity and intention.

In this edition, I'll walk through the career growth framework I've used for years—and show you how an AI copilot can make it 10x more powerful.

😨 The problem with winging it

In my early 20’s, I'd walk into performance reviews unprepared.

I'd ramble about wanting "more responsibility" or "growth opportunities." My managers would nod politely. Nothing would change.

I realized I was making a crucial mistake. I waited on my manager to outline my career paths for me. Whatever they didn’t verbalize, I also wasn’t bringing to the table for discussion. Hence, they couldn’t help me navigate either.

Here’s the thing:

It wasn’t their job to manage my career growth. It was mine.

This is doubly or triply important in startups or portfolio careers where roles are fluid.

The reality is that no one is going to care about your career as much as you. You need to own it. All of it.

That means getting crystal clear on what you want. Then building a plan to get there.

🗺️ Discovering a career growth framework

When I joined Dropbox in 2015, I learned a simple career planning framework.

This wasn’t perfect, but it was helpful structure I was missing at the time.

Early career growth plan example

This broke down into four core components:

1. Personal brand
What do you want to be known for?

No this isn’t about your Linkedin profile. It's about identifying the unique value you bring to the world.

2. Short-term goals
What do you want to achieve in the next 3-6 months?

Be specific. Not generic things like “get promoted” or “get a raise.” For example “facilitate a design thinking workshop with CXOs” or “hire a new engineer on the team.”

3. Long-term goals
Where do you want to be in 1-3 years?

This gives you a direction to march towards. An internal compass. It helps you say no to opportunities that don't align with where you want to ultimately go.

4. Key strengths
What are you already excellent at?

Finally, these are your leverage points. Double down on them to make a bigger impact in your role. Or perhaps it’s about finding a new role that aligns better with your strengths.

Once you have these four pieces, it’s not over. There’s more:

👈️ Working backwards

Let's say your short-term goal is taking on a role that doesn't exist yet.

(This was my friend's situation recently. She wanted to propose a scope change to her manager, but the role/scope doesn’t exist at her company.)

Here's how to prepare:

Step 1: Identify the skills gaps.
What skills do you need that you don't have yet?

Step 2: Build a plan to acquire these skills.
How will you develop those skills? Through volunteering for new projects at work? Joining courses?

Step 3: Identify people.
Who can support you and how? Your manager? Mentors?

Step 4: Craft your pitch / business case.
This part is missed 90% of the time. Why does it benefit the company to help you acquire these skills or make connections to the people you want to meet?

How do you connect your goal to something valuable for the business, executives, or your manager?

By the time you’re done answering these questions, you’ll have turned an aspiration into a concrete proposal to your manager.

That concludes the traditional way of doing things. Now let’s talk about how an AI copilot can help you take this to the next level.

🫶 How to setup an AI career copilot

I’ve really enjoyed using LLMs as a sounding board in business and career.

Here’s what I’ve done:

Set up a Claude Project as your career co-pilot. (ChatGPT project is fine too)

Upload your career growth plan from earlier. Or just your reflections and notes on the topic so far.

Then provide context about your role, company, and goals.

I adapted and modified the AI copilot prompt from Tal Raviv:

I am a [role] at [company name], and you are my expert coach and advisor, assisting and proactively coaching me in my role to reach my maximum potential.

I will provide you with detailed information about our company, such as our strategy, target customer, market insights, products, internal stakeholders and team dynamics, past performance reviews, and retrospective results.

In each conversation, I will provide you with information about a particular initiative so you can help me navigate it.

I expect you to: ask me questions when warranted to gain more context, fill in important missing information, and challenge my assumptions. Ask me questions that will let you most effectively coach and assist me in my role.

Encourage me to: [list the values and behaviors that make you successful in your role]

I want you to find the balance of: [traits you want in a thought partner and coach that will be both effective and fun to work with]

To set it up, I’ve fed the copilot prompt a shortlist of things to encourage me to do.

This helps fine tune the questions it asks me.

Then every time I have a career related topic, I’ll go into my copilot project and start a new chat thread.

For example, you can ask it to encourage you to:

• Suggest daily actions to take to help you reach your short-term goals

• Identify blind spots like where you’re not taking advantage of your strengths

• Spar with you on how to craft your business case for your manager

• Role-playing challenging conversations before they happen

Personally, I’ve asked my copilot to balance being a supportive colleague vs challenging/pushing me beyond my comfort zone.

I’ve asked it to ask me questions about trade-offs, challenge my thinking, and encourage me figure out how to deliver value quickly.

Give this a try and share your results. Curious how it goes.

🍎 Make it a habit

Here's my final suggestion:

Have a career growth conversation with your manager every six months, then use your AI copilot to prep for it.

If your company has a performance review cycle, sync with that. You can use the chance to prepare for your pre-scheduled manager chat.

If not, pick your own cadence. Propose a career growth conversation with your manager. Use your AI copilot to refine your document to share with your manager.

Plus, using the copilot makes the whole process a bit less dreary - and more fun.

✔️ In summary

• Own your career development instead of waiting for others to drive it

• Use four components: personal brand, short-term goals, long-term goals, key strengths

• Work backwards from goals to identify skills, people, and narratives you need

• Set up an AI career copilot to challenge your thinking and prepare for conversations with your manager

• Review your plan every six months to stay on track

In the spirit of autonomy, it’s all about putting you in the drivers seat of your career. Not your manager.

What's your biggest challenge with career growth planning? Reply and let me know.

💎 Last Week’s Gems

🗣️ Choose Your Own Adventure: How to Have a Career Conversation (Deb Liu)

🚀 Here is how I approach starting a new job (Elena Verna)

◀️ Reverse impostor syndrome (Wes Kao)

💌 Reader Notes

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

I started a full-time role 2 weeks ago.

After two years building my consulting practice and Portfolio Path, this might sound like I'm abandoning what I’ve been writing about.

But here’s the thing: this move actually enables my portfolio career vision.

Today, in 10 minutes or less, you’ll learn:

• 🚪 Why I walked away from buying an accounting firm after months of work

• 💼 How this full-time role actually fits my values and accelerates my other portfolio bets

• 💰 How I’m getting business ownership while minimizing capital risk

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🇸🇬 I just took a full-time job (here's why)

Last year, my wife and I spent a few months trying to buy an SMB accounting firm.

We analyzed deals. Spoke with brokers. Partnered with accountants. Our vision was clear: take a traditional cash-flowing business and transform it with technology.

But we eventually shelved the idea.

Either partnerships didn’t work out, the deals didn’t make sense, or the capital required exceeded our risk appetite.

Then earlier this year, I caught up with Noah Pepper.

He was building Multiplier Holdings - which originally started with financial SaaS. Last year, they pivoted to acquiring and tech-enabling professional service firms.

Essentially what I wanted to do, but with $27M+ in capital and a world-class team including the former eng lead of Stripe Billing, M&A specialists, and firm owners.

Not to mention, it aligned with a life transition my wife and I were planning (I’ll explain below.)

That’s why I recently joined to lead the new corporate accounting pod, which transforms their portfolio accounting firms. It’s been more fun than I expected.

Here’s how I thought about this decision:

🎯 Why this move fits my portfolio path

I spent the last few weeks explaining this to some confused friends:

"But weren't you all about autonomy and flexibility?"

Yes, I still am.

I don’t see portfolio careers as collecting only part-time gigs. Instead, it’s about creating a portfolio of bets that help you live according to your values.

Mine include autonomy, curiosity, adventure, and relationships.

Here are the reasons why this move supports what I care about:

1/ Relocating to Singapore + location flexibility

After a lot of reflection, my wife and I decided to relocate back to Singapore to eventually start a family. This means we’ll move from Mexico by January.

Exploring Oaxaca, Mexico

Multiplier is based in Singapore, which perfectly matches our plans. It’s also a fully remote company - which allows me to work from anywhere.

This comes with trade-offs (coordinating London, Singapore, and SF time zones is no joke!). But totally worth it in my book.

2/ Gaining ownership while reducing capital risk

Previously, I struggled with the idea of borrowing >$1M with a personal guarantee to buy a business.

Now instead of buying one firm with my own capital, I can help transform multiple firms with Multiplier’s funding.

On top of that, my compensation is directly tied to the cash flow I generate for our portfolio firms. I get the upside of ownership without putting my own capital at risk.

3/ Pursuing my curiosity in AI and automation

I used to dread the admin/ops parts of PM jobs. But with AI automating lots of that away, I've never felt more excited about building products.

A typical PM day, pre-AI

Prototyping is 10x faster using Magic Patterns and Claude Code. I can leverage LLMs to transcribe, create notes, and generate Mermaid diagrams from research sessions. It’s quick to setup agentic workflows to automate my ops.

I also get to work at the edge of applying this new tech to cash-flowing traditional businesses. Building products feels like play again.

4/ Going from solo to talented team

Let’s be real. Being a solopreneur gets lonely. It’s been energizing to work with a tight knit team that I learn from and grow with.

No matter what businesses I build in the future, I’ve realized how I want to work with partners instead of doing it alone. It fundamentally changes the quality of the experience.

—

With that said, this doesn’t mean that I’m giving up Portfolio Path. Quite the opposite.

Here’s how I see the journey evolving from here:

🚀 My portfolio path evolves

Most people think portfolio careers mean cobbling together five different income streams.

But sometimes the right portfolio move is doubling down on something you really believe in.

Beyond values, I zeroed in on a few factors in this decision:

• Cashflow and equity upside

• Time and location flexibility

• Meaningful, values-aligned work

To be clear, I'm still running Portfolio Path and advising startups. But I also believe this role will accelerate other bets in my portfolio.

If there’s anything I’ve learned over the past 12 years of working, it’s that careers are not linear. Sometimes doubling down on 1 thing helps you unlock 10 other doors.

💡 What this means for you

If you're wrestling with similar decisions, here's what I learned:

Seek opportunities to gain upside while minimizing risk. I wanted to buy an SMB firm with my own capital. Now I'm transforming multiple firms without taking on additional capital risk - and I still get a piece of our upside from cash flow generation.

Be clear on your portfolio-friendly terms, but stay open minded. I knew my wife and I wanted to relocate back to Singapore. I knew I wanted remote work to manage my time more effectively. Don't assume "full-time" means giving up flexibility.

Build leverage on your time, money, and/or relationships. This role helps me become a stronger builder, AI practitioner, and partner to business owners. I'm also getting rare insight into high-performing businesses in a new industry - which will serve me well down the line.

📍 The bottom line

The portfolio path isn't about avoiding employment.

It's about strategically choosing bets that align with your bigger vision.

Sometimes it’s a side hustle. Sometimes it's fractional work.

And sometimes, it's a full-time role that connects the dots between your values, skills, goals.

P.S. I'm hiring software engineers and a product designer in Singapore/Southeast Asia for my team. Hit reply if you’re curious, I’d love to chat.

💎 Last Week’s Gems

🤔 Why the 4% Rule is More Like the 2% Rule (Ben Carlson)

💡 The 25 Most Interesting Ideas I've Found in 2025 (So Far) (Derek Thompson)

🗒️ 15 Hot Takes That Cut Through the AI Hype (Peter Yang)

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

Recently, I’ve been heads down in Claude Code. I wanted to share a practical workflow you could implement in your business today.

Let’s dive in!

Today, in 10 minutes or less, you’ll learn:

• 💎 Why drowning in client feedback is actually a goldmine waiting to be unlocked

• ⚡️ Why Claude Code beats regular Claude Projects for serious customer development

• ⏱️ How a non-technical person can build a client research workflow in 15 minutes

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🎯 What you get:

• Lifetime access to Portfolio Path Community

• Expert fireside chats, peer workshops, & community calls

• 30-day challenges and group accountability

• Shared resource library (AI workflows, offer templates, etc.)

• Full access to PT Consulting Launchpad lessons + workbook

• Full access to Consulting Offer Blueprint

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💡 How I built a client research analyst in 15 minutes (using Claude Code)

You’ve gotten your first clients. You’re finally scaling up.

But now you’re drowning in service delivery. Overwhelmed.

You absolutely don’t have time for customer research, when you barely had time to do your own laundry yesterday.

However, you just know your 14 recent client calls must contain nuggets of insight that can help level up your service quality or grow your business faster.

So how do you unlock these insights without overburdening yourself?

Previously, I showed you how to use AI prompts for customer research.

An obvious solution: Dumping your client meeting notes into a Claude Project, then running an effective prompt over them. I still do this a lot. It’s fantastic.

But sometimes it’s not enough.

In these cases, I bring out the heavy artillery - Claude Code.

While it looks intimidating at first, I’ve found it extremely powerful even as a non-technical person.

Today, I’m going to show you how I leverage Claude Code to accelerate my client research workflow in 15 minutes.

1/ Why Claude Code?

I still use Claude Projects a lot, but have run into several pains:

• Too much copy-pasting between Claude + docs

• Repetitively uploading files into projects

• Difficult to move context across chats

• Losing track of my prompts

• Inability to update docs

Not to mention - that feeling of horror when I see my Claude Desktop app freezing yet again.

Claude Code emerged onto the scene this spring.

At first I was skeptical. But then I tried it after hearing so much hoopla about it - and was blown away. Using it was the first time I felt a visceral “agentic AI” moment.

Now I’m leveraging the tool not only for coding, but also business workflows.

Hopefully this client research walkthrough can show you how Claude Code can help you too.

2/ How to setup Claude Code as a non-technical user

First things first. To get Claude Code running, I whipped up the ol’ Terminal:

If you’re not a dev, don’t be scared of Terminal. You’ll get used to it.

Next, I downloaded Claude Code by entering this command into terminal (Anthropic’s full instructions). Here it is for Mac:

curl -fsSL claude.ai/install.sh | bash

And for Windows:

irm https://claude.ai/install.ps1 | iex

Then, I created a “customer_research” folder in my Finder and navigated to it using the command “cd customer_research” (quick instructions).

Once I was there, I typed “claude” in the terminal to open Claude Code:

Boom. You’re in.

Now for the exciting part - building your own analyst.

3/ Building a client research analyst

Now that we’re in Claude Code, I’m going to show you how I setup my research analyst.

I created a sub-folder meeting_notes and uploaded all my meeting notes, transcripts, and documents as markdown files.

Afterward, to avoid having to copy-paste prompts, I created a Claude Slash Command. To do this, I created two prompt files in the folder .claude/commands:

• topic_analysis.md: Analyzing customer feedback and bucketing them into 4 topics: pain points, blockers, customer requests, and solution feedback.

• insight_generation.md: taking the output and grouping similar snippets into common insights with actionable recommendations.

This basically saved my prompts as markdown files in a folder, which is pretty convenient. No more losing track!

Next, I prompted Claude Code to run the topic analysis and save the output in a markdown file called topic_analysis_output.md

Then, I fed this output into the insight generation prompt to created the final synthesized insights.

Voila! I got a research summary of client insights, supporting quotes, actionable recommendations grouped by the topic.

The actual research output was a great starting point:

I’ve been impressed by how Claude Code manages context more smoothly than Claude Projects, producing higher-quality outputs IMO.

In particular, these insights helped me answer questions like:

• What are the common pain points, requests, and feedback?

• What are the actual quotes clients have said related to this insight?

• What actions should I take in response to this feedback?

Separately, I’ve also built a web dashboard to visualize this data with charts and a structured UI. (Not covering this today, but so much easier to create than before with Claude Code.)

4/ Wrapping up

From here onwards, I can see tons of possibilities.

I can use this research output to do things like:

• Craft ideal client profile descriptions

• Create a dashboard UI (like above)

• Generate sales landing page copy

• Build the actual landing page

• Create a discovery call script

• Write sales emails copy

All within Claude Code. And that’s just the tip of the iceberg.

So would I recommend Claude Code?

It might seem intimidating as a non-dev, but I’d recommend trying it out if you’re feeling inspired and not afraid to get your hands dirty.

And if you do, building your own customer research analyst could be the perfect weekend project. Let me know how it goes.

💎 Last Week’s Gems

🤯 Shorting the AI jobs apocalypse (David Deming)

🧠 On the Reverse Flynn Effect (Cal Newport)

💵 How to Keep This Hot Stock Market From Melting Your Retirement Dreams (WSJ)

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

The internet seems divided into two camps:

1. Never ever do free work!!!

2. Free work is the best thing since sliced bread

Which camp is right? Let’s dive in.

Today, in 10 minutes or less, you’ll learn:

• 🎯 When free work is a smart investment vs. a costly mistake

• 💰 How successful portfolio careerists used free projects to get their first clients and even build 7-figure businesses

• 🛡️ A strategic framework for setting boundaries and maximizing returns

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Our waitlist enrollment ends in 48 hours (Tuesday, Sept 9). The cohort kicks off on Sept 17th.

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🤔 Should you do free work?

“Should I do free work for this potential client?”

This is one of the most common questions I’ve gotten in our cohort.

The person asking usually has 10-15 years of experience, is exploring some version of fractional work, consulting projects, or advising - and just got off a call with a client who liked their offer but just couldn’t pay.

For my own work, I have completely flipped my answer.

A few years ago, I used to be firmly in the camp of “free work devalues your skills!”

This is how I viewed free work. Maybe you resonate?

When I was doing career coaching, I met well-meaning coaches get burned out from coaching “for free” on repeat. At its worst, free work felt like a tragic waste of time.

But the longer I’ve been working, the more portfolio careerists and entrepreneurs I meet who started out by doing a free project (or two) for a friend or ex-colleague. And as a result, they garnered testimonials. Reputation. Referrals to clients.

I also noticed how free work accelerated my own progress too.

Hindsight is really 20/20.

Here’s my personal journey with free work, how other professionals deal with it, and how to leverage it strategically in your portfolio career:

🤷‍♂️ My love-hate relationship with “free work”

In 2019, I started career coaching by providing free discovery calls, which led to garnering positive reviews on Hireclub. I wasn’t formally trained as a coach (ICF or otherwise), so this was an excellent way for me to test the waters for demand.

While I still do free discovery calls, one thing I learned is that folks who booked repeat discovery calls - over and over - rarely signed up for my services. I grew wary of this.

Around the same time, I met several other coaches who struggled with a low conversion rate due a smattering of reasons. The clients didn’t have their finances in order, weren’t serious enough, were just exploring, etc.

These insights left a deep impression on me. I saw what I wanted to avoid.

🟡 Lesson #1: Free work sometimes attracts clients with no intention to pay. Be wary of who you’re attracting.

—

However, I was surprised by one event. I had a paid client who was struggling with her mental health at her workplace. We tried to help her navigate this in a couple sessions, but I didn’t feel confident we could help her achieve her desired results.

So I refunded her and suggested exploring a mental health professional.

Turns out, this client later wrote a strong positive review about my services in a career-related FB group - which referred potential clients to me even 2-3 years later.

💚 Lesson #2: Free work for the right clients can lead them to share your services with others, generating word-of-mouth referrals. 

—

Later, I paused coaching in 2023 due to launching B2B product consulting and advising services.

I didn’t do free B2B projects given I already had industry experience to leverage, but being actively involved in a startup ecosystem means you are freely giving value all the time:

• Having a 60-minute brainstorming call with a founder

• Speaking at a conference or company’s office

• Hosting a workshop for an accelerator

• Writing content for tech publications

Doing this made me realize the 3rd lesson:

💚 Lesson #3: I prefer to charge two prices for my value - free and premium

—

Ultimately, it wasn’t until recently that I’ve internalized that doing free work is one of the best forms of distribution on the planet!

Counterintuitively, I’ve attracted really amazing clients via doing free work.

And you can always charge a premium price for a premium service, which more than covers the cost of this free work you do.

Of course, you need to balance this with the challenge of doing the right free work (demonstrates your expertise) and for the person or group (strong willingness to pay for value).

Now let’s take a look at how others approach this:

🙌 What other professionals have done

In our community, we’ve hosted a number of fireside chats with experts (🎯) and our cohort alumni (🎓) who did free work earlier in their journey:

• 🎯 Audrey, founder of Mapo Studios, a 7-figure product design studio, started with zero design experience as a PM, working at Canva. To get started, she did free design projects for startup founder friends to build credibility and testimonials for her design work.

• 🎓 Ines, a content strategist for 7-figure creators (Ali Abdaal, Veritasium, Zaid Khan), started out by sharing free content breakdowns with her potential clients before starting a paid engagement - which demonstrated her expertise.

• 🎓 Makar, a fractional CTO, began by providing free audits or health checks for traditional commercial service firms to show how off his capabilities.

• 🎓 Janani, an engineering program manager at Apple, started offering free coaching sessions for project managers to build trust before launching paid workshops and bootcamps.

Audrey sharing her 0-to-1 insights

As you can tell, free work helped these professionals with things like transitioning into a new function and building fresh credibility.

Finally, let’s switch gears to when and how to use free work:

🎯 When to leverage “free work”

✅ You're entering a new domain or skill area. Like Audrey pivoting from PM to design, or when you're applying existing expertise in a new industry. Free projects can help you build domain credibility fast.

✅ You have zero testimonials or case studies. No one wants to be your first paying client. But people will let you prove yourself for free, especially if they know and trust you personally.

✅ You want to validate your service quality. Test whether your service actually delivers results before charging premium rates. Better to discover gaps in a free project than with a paying client.

✅ The client is willing to share their network. Working with one well-connected person can open doors to multiple paid opportunities - because referrals!

❌ When NOT to do free work:

• You already have paying clients and strong testimonials (usually)

• The person isn’t a fit for getting value out of your services

• The person has a pattern of asking for free help repeatedly

• They can clearly afford to pay but choose not to

• You're feeling desperate or undervaluing yourself

Even if you have paying clients, free work can be useful as distribution - to spread awareness of your expertise.

Free work can be powerful when done well, but you need to be strategic about it.

⚡ How to do “free work” strategically

• Ask for testimonials - If the client is happy, then I’ll end the engagement by asking “Would you be open to giving us a shoutout or testimonial?” If they say yes, I send them a list of questions they can answer on video or through Testimonial.to.

• Build case studies - Document the results you achieve, even from free projects. "Helped drive +20% MoM growth” or “Launched a new product line” becomes awesome social proof for future paid clients.

• Validate your service quality - Often, you don’t know if your service is that good yet at the beginning. That’s why now is the perfect time to get real-world feedback on your service quality - before you start charging gobs of money for it 😉 

• Choose clients strategically - Sometimes it makes sense to do counterintuitive things like work with a startup with no budget vs an enterprise with tons of cash because the former is willing to introduce you to all their founder friends.

💡 The bottom line

I used to hate the idea of free work, but now I’ve done a 180.

When done strategically, free work helps you build credibility and becomes your best distribution channel.

When done carelessly, it can be a colossal waste of energy and time.

The pros who I see succeed with free work leverage it to:

• Switch to new domains

• Build trust and reputation

• Validate their service quality

• Garner client referrals

And as a result, they jumpstarted their portfolio careers.

What's your experience with free work? Hit reply and let me know - I read every response.

P.S. If you're ready to build a part-time consulting business, join our final Launchpad cohort by September 9. Enroll now.

💎 Last Week’s Gems

📊 Treasury Bonds Can Appreciate in Value (Financial Samurai)

🐻 Why I’m Bearish on U.S. Stocks (for the Second Time Since 2017) (Nick Maggiulli)

🧑‍💻 There is significant unmet demand for developers who understand AI (Andrew Ng) - Side note: I recommend Andrew’s DeepLearning.AI newsletter. Bit technical but grounded takes on what’s AI hype vs reality.

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

Back home in Mexico City from our honeymoon and feeling refreshed! 😎 

This week’s edition is going to be a quick one covering what you can expect from me and the team at Portfolio Path for the rest of 2025 and beyond.

Let’s dive in!

SPONSORED

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After this cohort ends, the Launchpad will only be accessible as a self-paced course within our community.

Here's what you need to know:

• Waitlist Enrollment opens September 3, 2025

• Only 10 Spots Are Available

• Cohort kicks off on September 17

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🚁 A new vantage point

Last week, I felt terrified I was going to fall out of helicopter over the eroded volcano.

We took an open-door helicopter ride in Kauai, and I was surprised by just how beautiful the lush landscape looked from above vs from the ground.

The waterfall-laden mountains were like a scene out of Moana. Seriously.

Without switching to an aerial view, I’d have missed out on this magic.

For the past 6 months, I’ve been heads down - in the weeds - of building Portfolio Path.

On my honeymoon, I got to see things from a different vantage point, connect the dots, and envision what work looks like for me in 2025 and beyond.

Through my reflections, I realized what’s most important.

When I launched Portfolio Path in February, I didn’t set out to just teach consulting tactics.

Our mission has always been to empower intentional high-performers to live on their own terms.

Yet after talking to hundreds of our readers/members (mainly tech workers), a few patterns emerged:

• Professionals feel heightened fear/anxiety around economic volatility and disappearing traditional job security

• People recognize AI helps future-proof their careers, but don’t know what actually moves the needle

• Portfolio careers are highly desired, but people don’t want to do it alone nor get left behind

The biggest barrier to taking an unconventional career path doesn’t seem to be possessing enough role-related expertise but rather the fear of navigating this shift alone/getting left behind during a tough economy.

Hottest topic in my reader calls (no pun intended).

That’s why Portfolio Path is evolving to meet your needs.

Over the next few months, we’re doubling down on content and programs that help you adapt to this rapidly changing work landscape - and build sustainable portfolio careers in the 2020’s.

Below I share three key updates you can expect from the newsletter and programs help you start, grow, and thrive on your portfolio careers.

🗺️ Recapping where we’ve been

I’m proud of the milestones we’ve crossed in the past few months:

• Launched a brand-new community with over 40 members including ex-FAANG professionals, fractional CTO/CFO/COOs, agency owners, and PT tech consultants

• Completely revamped our Launchpad product, delivered 2 strong cohorts (9/10 avg rating)

• Launched the Blueprint, generating our first digital product revenue

• Helped dozens of professionals launch portfolio careers via our programs

Not to mention more mundane things like fully migrating off the Kajabi platform (ugh).

As chaotic as wildebeests crossing the river.

With that said, it hasn’t always been smooth sailing.

I experienced my fair share of entrepreneurial anxiety/self-doubt, witnessed the gradual erosion of social media, and had to make hard decisions about market direction.

Despite these challenges, Portfolio Path is alive and stronger for it.

Now here’s what you can expect from us going forward:

🔑 What you can expect from us

We’ll be doubling down on Portfolio Path becoming the leading community for portfolio careerists to experiment, learn, and grow together.

Our focus is serving mid-career professionals - especially those in the tech industry and/or possessing a startup/entrepreneurial mindset.

I’ve learned that in the AI era, it won’t be enough to possess skills. Judgement and relationships will play a huge role in differentiating yourself in the talent market.

That’s why I strongly believe communities will be essential for those seeking career autonomy.

Communities are a unique opportunity to build peer, mentor, and partner relationships that can help you take control of your portfolio path.

Personally, I’ve received heaps of value from being a part of multiple professional communities - from growth groups in SF in my early career to entrepreneur/creator circles today.

In the Portfolio Path community, we’ll accept a limited intake of new members every month to ensure a high-quality experience. (You can apply here.)

All smiles at our Singapore members meetup last week!

Meanwhile, I'm spending more time working on AI projects.

I enjoy nerding out on emerging tech, but that’s just one reason why.

As I’ve written previously, I view high-leverage AI adoption as a key trend enabling the rise of 10x workers and portfolio careers.

I’ve already started seeing small teams become insanely productive, underscoring the potential emergence of new business/employment models. This is exciting to me.

For example, some of our community members are already heavily using AI to run their agency/service businesses. Using the tech, they can scale their output and deliver a more compelling client experience without hiring more staff like 5 years ago. Pretty cool.

My goal is to stay 6-12 months ahead of the curve of what’s practically possible in AI to help business owners get more leverage and take control of their time.

Along the way, I’ll share what I learn as much as possible with you - so that you can apply it to your own portfolio career or business.

Here’s what this means for you:

1. More signal, less noise. Instead of weekly updates, you’ll receive bi-weekly high-quality deep dives starting September 14th.

2. Final Launchpad LIVE cohort starting in September. Afterwards, it’ll only be accessible as a self-paced course in our community membership. If you've been thinking about launching a consulting business, this is your last chance to join our popular 8-week program.

3. Practical AI content. I'll write about specific AI business workflows and insights helping our members leverage their output by 50%, 2x, or even 4x.

🙏 That’s a wrap

Keeping this edition short and sweet. For everyone reading over these past few months, thank you for supporting Portfolio Path.

I owe a lot of our recent successes to readers/members like you, and can’t wait to continue serving you over the coming months and years.

P.S. What do you think of this new direction? Reply and let me know your thoughts!

💎 Last Week’s Gems

🪴 How to Build a Career That Thrives Alongside AI (Ines Lee - our alum!)

🤑 2025 State of the American Investor (Fidelity)

🧑‍💻 These AI-Skilled 20-Somethings Are Making Hundreds of Thousands a Year (WSJ)

➕ What are you optimizing for (Jack Raines)

🤩 Community Spotlight

🇸🇬 Michael hosted our first-ever in-person Singapore meetup!

🇬🇧 Marilyn is launching her first event at the Royal Society of Arts in London on 8 September: When Everything Changes at Once: Navigating AI + Career Disruption

🤓 Deassy recently onboarded new global team members for her product research firm.

Join the waitlist for our invite-only community and we’ll notify you when our September intake begins:

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

Taking this week off for my honeymoon! We are safari-ing in Tanzania, then poke bowl-ing in Kauai.

If you’re looking to learn something in the meantime, check out our best deep dives in the archives.

Ready to build your portfolio path? Two ways to join us:

• Founding member access to our invite-only community

• 8-week PT consulting cohort starting September 17

Back next week with stories and fresh insights!

Dexter

Hi {{ first_name | there }},

Everyone obsesses over the ROI of AI automations. But there's something way more important than time savings alone.

Today, in 10 minutes or less, you’ll learn:

• ⚡️ How a 19-year-old's data entry nightmare sparked a career-long mission against tedious work

• 🎯 The counterintuitive "energy drain" filter that beats traditional ROI calculations

• ⭐️ 3 proven workflows you can set up this week (with templates you can steal)

SPONSORED

🚀 Launch your consulting side business in 8 weeks

Click Here to Early Enroll

Ready to finally get started?

Part-Time Consulting Launchpad is our 8-week cohort program to build your profitable consulting business - without quitting your day job.

Our alums include over 100 senior professionals from Google, Apple, Stripe, Tik Tok, and fast-growing startups.

Here's what you need to know:

• Waitlist Enrollment opens in Early September

• Only 10 Spots Are Available

• Cohort kicks off on September 17, 2025

• Lifetime Access

Waitlist members get an exclusive 25% OFF and 24-hour early access before public enrollment - so make sure you save your seat:

Can’t wait? Get immediate access to our invite-only community

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

⚡️ How to automate the energy-sucking parts of your job

When I was 19, I spent my summer painstakingly plugging numbers from tax forms into a giant spreadsheet - as an intern for a nonprofit consulting group.

To be clear, I did get to do exciting projects. But I absolutely dreaded this manual data entry task (at least I wasn’t fetching coffee).

After the summer ended, I promised myself I’d never take a job filled with corporate drudgery. No matter how much they paid me.

Last week, I saw this Linkedin post from Jay Singh, CEO of an AI product studio:

His view tracks closely with how I see work evolving over the next 5 years.

The priority for leaders and managers shouldn’t be about replacing humans (although this is certainly happening).

Instead, the priority should be:

Attracting, hiring, and retaining top talent.

Leaders have prioritized this strategy for centuries because it’s effective, and the 2020’s are no different. The tools have just changed.

A smart talent strategy sounds like leveraging AI and technology to automate away the tedious parts of jobs, so top talent can spend more time on energizing work.

And if you’re a solopreneur, then you are the management AND employee. You are the one in charge of designing work that gives you energy.

In this edition, I walk through exactly how I prioritize automations, what tools to use, and popular use cases you can apply to your work - whether you’re a professional, solopreneur, or business owner.

🏔️ Find your biggest obstacle

Before giddily jumping into automating everything, make sure you’re focused on the right-sized problem.

For example, I used to work on automating financial operations. The worst feeling was spending months automating a complex compliance requirement only to realize it didn’t need to exist in the first place!

💯 The counterintuitively simple way to prioritize

Now that you’ve picked a problem worthy of automation, generate your hypotheses and start ranking them using the factors from Jay’s post:

1. Repetitive

2. High-effort

3. Energy drain

I personally love how he weights low-creativity / energy-draining work.

This is a super underrated criteria.

I’ve worked with many leaders who cultivate a culture of grind for the sake of grinding. But the leadership style I admire and adopt is making work fun and energizing - because I strongly believe this enables people do their best work.

🧰 Your automation starter pack

If you’re just starting out, I recommend trying Relay and Make.

Why?

• Affordable options that you can quickly setup to justify ROI

• Relatively easy to use for non-technical users, especially Relay

• Extensive integrations list with most popular tools

• Both have a solid free plan for getting started

I use both in my work.

Here’s a quick hits list of what I’ve tried:

• Entry-level (non-technical):

  • Zapier - the OG automation tool

  • Relay - AI-native, user-friendly, free tier available

  • Lindy - similar to Relay but higher price point

• Mid-level:

  • Make - established automation with new AI modules, good customization, inexpensive

• Advanced:

  • N8n - very popular, requires API/JSON knowledge, has native AI agent capabilities

  • Vector Shift - enterprise-level, built for complex workflows/scale

🏆️ Quick wins (steal these templates)

Now that you have your tools, let’s show you a few quick wins.

Linkedin/X are filled with viral AI automation posts claiming “I automated my whole business with n8n!!!”

But how much of that is real?

That’s why I’m only sharing workflows I actually use (and any professional can use):

1. Weekly task review report

2. Newsletter summarizer

3. Voice note → content brief generator

1/ Weekly Task Review Report

Struggling to stay on top of your tasks?

I track all my team tasks in a Notion board, then ask GPT-4o mini to send a weekly task report to Slack that summarizes:

• Progress Last Week

• Plans This Week

• Problems/Issues

After reviewing this in Slack, I update my plans for the upcoming week.

👉️ Get the Make Template

The report I get every week

2/ Newsletter summarizer

Every week, I spend some time digesting my 50+ newsletter subscriptions, so I can:

• Find interesting content to share in the Last Week’s Gems section

• Curate ideas of topics for future content

• Learn a new skill or knowledge

Obviously, going down this rabbit hole can get extremely time-consuming.

That’s why I took an out-of-the-box Relay template for generating newsletter summaries - and then lightly edited the GPT prompt to also extract insights for Portfolio Path readers/clients.

I highly encourage this technique.

Start with an existing automation template, then tweak it for your personal or business goal.

👉️ Get the Relay Template

The email digest I get everyday

3/ Voice note → Content brief generator

Every week, I write a newsletter - but I’m embarrassed to admit I save it to the last minute way too often.

I have been feeling a bit frustrated at myself because I’m proud of being “consistent” but at the same time I’m treading water!

To get ahead, I’ve started recording voice notes on my afternoon walks, then setup a Make automation to generate a Notion content brief.

I then use this brief to guide my writing.

Even if you don’t have a newsletter, we all write so much in knowledge work. Imagine if you can cut down your writing by talking podcast-style instead.

Wouldn’t that make things easier?

👉️ Get the Make Template

The content brief I generated last week

In summary

The AI opportunity isn't about replacing humans - it's about redesigning work to be more energizing.

No one I know wants to be grinding through repetitive tasks, but it’s just the proactive people I know who are systematically eliminating the energy-sucking parts of their work.

Here's what we covered:

• Start with your biggest obstacle - Don't automate everything, automate what’s a real problem

• Use the energy-drain filter - Prioritize repetitive, high-effort tasks that drain your creativity

• Begin with entry-level tools - Relay and Make offer the best ROI for most professionals IMO

• Steal proven workflows - Weekly task reviews, newsletter summaries, and voice-to-content generators

In spite of the doom-and-gloom news reports, I’m excited about what the future holds for folks who take charge of transforming their work for the better.

What energy-sucking task will you automate first?

The 19-year-old intern in you will thank you for it.

Thanks for reading! What automation are you most excited to try? Hit reply and let me know.

💎 Last Week’s Gems

😡 How One Big Private-Equity Fund Makes Its Numbers Incomprehensible (WSJ)

🤑 The Best Leading Indicator of Wealth (Nick Maggiulli)

🧠 No one knows anything about AI (Cal Newport)

💭 Doomprompting Is the New Doomscrolling (Anu)

📆 Upcoming Workshops

• September 4th, 6pm PST / 9am SGT: Topic TBD → Register

• October 2nd, 6pm PST / 9am SGT: Topic TBD → Register

Dates don’t work? You can visit our website for more upcoming events.

💌 Reader Notes

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hey {{ first_name | there }},

Solopreneurship is all the rage, but why not go duo instead of solo?

Today, in 10 minutes or less, you’ll learn:

• 🤝 Why a 25-year tech veteran chose a business partner over going solo

• 💰 The counterintuitive revenue split and simple framework they use to decide which projects to take

• 🔥 Why their biggest "conflict" is actually their secret weapon for impressing founders

SPONSORED

🤩 Join as a Founding Member of our Invite-Only Community

Click Here to Apply Now

Ready to accelerate your portfolio career with like-minded peers?

If you have 5+ years of working experience, join our invite-only community (launching August 2025).

🚀 Why join the community: Accelerate your learning, grow your revenue, and build genuine relationships with an exclusive group of portfolio professionals

🎯 What you get:

• Lifetime access to Portfolio Path Community

• Expert fireside chats, peer workshops, & community calls

• 30-day challenges and group accountability

• Shared resource library (AI workflows, offer templates, etc.)

• Full access to PT Consulting Launchpad lessons + workbook

• Full access to Consulting Offer Blueprint

Only 5 founding member spots available. Apply now - we'll notify accepted applicants within the next couple weeks:

OR learn more about our Community Track vs Cohort Track

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

🧨 Building a Fractional Partnership | Ha Nguyen

Over the past two years, I’ve met many portfolio careerists but 90% are going solo.

I understand that solopreneurship is all the rage, but my ears perk up when I hear about alternative models like fractional collectives and multi-person consulting teams.

That’s why when I saw Ha Nguyen, a Silicon Valley tech executive for over 25 years, choose to build a two-partner consulting business instead of going it alone, I knew I had to interview her.

From day 0, her and her business partner Garrett have built Next Step Consulting and Advisory together.

In this unique feature, Ha shares how they met, decided to work together, structured their fractional partnership, and whether or not they’ll continue with the model in the near future.

Without further ado, here is Ha:

Ha is a managing partner at Next Step Consulting and Advisory, where she and Garrett work with seed to series B startup founders on strategy, operations, and people excellence. She has 25 years of tech experience, starting as one of the first six product managers at eBay when it had just 200 people. After spending five years in venture capital, she took a COO role at Swimply during the pandemic—her favorite role of her career—where she built the company from the ground up, hired the executive team, the entire team, ran operations, supply side growth, community, HR and people.

Most fractionals seem to operate solo—what made you decide to bring on a partner instead?

I knew that I did not want to go at it alone. If I had to, I would have. But I felt like consulting is going to be lonely.

And I'm not always going to know the answers. No matter how much experience I have, there's stuff that you can always learn and grow and have a perspective on. That's why I knew I wanted to have a business partner.

Garrett and I met when I brought him onto the team at Swimply, which was the Airbnb of swimming pools. I was the COO, and after that first summer of running operations, I realized it's all about dealing with trust and safety problems. I needed to bring in somebody who actually knew what they're doing as opposed to somebody like me who was just making it up as we went along.

I reached out through LinkedIn to every director level person and above I could find leading trust and safety at Airbnb, Instacart, Uber, DoorDash, and similar companies. In one of those conversations, I got introduced to Garrett.

When Garrett came in, not only did I have him lead trust and safety, but then I realized that he had a knack for strategy, operations, and business operations. He essentially ended up being my chief of staff and kept me sane through all the craziness. We worked together for a year and a half at Swimply. That's where I really got to see how he operated, his thoughtfulness, his wisdom, and his approach to problem solving.

When I decided to leave after two years and realized I wanted to do fractional consulting, I knew that there was only one person that I wanted to ask to be a partner in this journey. I have a huge network with 15,000 connections. And I've worked with amazing people, but there was just one person that came to mind. It had to be Garrett.

It took me about four months to convince him to say yes because he was still in his career building years, but I wouldn't take no for an answer. I was very savvy about it - I would hop on calls with him once or twice a week, sometimes I would go up to Portland to visit him, and we'd map out what this could look like if we were to do this together.

Ha and Garrett

How do you divide business development responsibilities between you two?

It's interesting because I have the network. Everything comes in through me. I might take an initial call with the founder by myself. And if there's anything there, then I'll pull in Garrett into the next meeting.

I like to do calls with Garrett together for a few reasons:

1. It’s good that there's two of us so that we're not missing anything.

2. It makes me sound smarter because if there's something that I have no idea what to say, he has something to say or vice versa.

3. We can always debrief afterwards. What do you think of the founder? What do you think of the business? Do you think we can help?

I have more confidence in doing the business development and closing the deals when Garrett's with me. Somewhere in the call, the founder will figure out that there's something real - i.e. Ha's smart, Garrett's smart, or we're both a dynamic duo. If I was by myself, I might not sound so smart. But the two of us, we figure it out.

How do you two make those decisions together on whether or not to take a project?

In terms of whether or not to take on a client, it’s easy.

Usually, when we're introduced to a founder, we hop on a call together to learn about the business, the founder, and their needs. Then depending on what the founder's needs are, there are some things that naturally make sense for Garrett to take and then other things that make more sense for me to take. If Garrett doesn't want to take it and it’s not in my wheelhouse, then I say, let's just pass.

We do sometimes bring each other on to help with client engagements that we're individually working on. From time to time, there might be a need the founder might have that is in the other person's wheelhouse. We'll just bring them on and renegotiate the engagement to add a second person.

When a client wants to work with both of you versus just one, how do you price that?

It will probably be doubly expensive. But the reality is more nuanced - there will always be a lead partner. So it's rare where we're both equally contributing. It'll usually be Garrett taking the lead, and I will just support in some of the areas or vica versa.

In terms of pricing structure, they’re all monthly retainer agreements. It's roughly based on a number of hours or fraction of our time. For example, if it’s a 20-hour week retainer engagement, maybe it's me taking 15 of it and Garrett taking 5 of it. But we price it as just one price.

If we just start with one of us, but we eventually pull in a second, then we increase the scope and price.

How do you actually split revenue between you two?

We structure as a 50/50 business partnership - meaning we split all revenue and expenses 50/50.

I probably bring in more, but I don't care because I'm not in it to make money. Of course, I should get paid for the value that I bring to founders, but money is not the main motivator. What I want is for us to be a true partnership of equals.

This means that we both have an equal say in how we want to structure our firm. Do we want to grow it? What direction we want to take it? I want him to always feel like this is an equal partnership. I never wanted him to think “oh, I'm not making as much money in this business or I'm a junior partner.” After all, we started this together.

What's been your biggest partnership conflict so far, and how did you resolve it?

I don't know that we've had a conflict. It is pretty crazy how well we work together.

The only thing is we have such different working styles.

For me, I'm constantly coming up with ideas. If I have the idea, I need to get it out. I'm constantly pinging him on WhatsApp. And that is not his style at all. He's much more thoughtful and organized and disciplined.

When we usually get together at least once or twice a year in person, we'll do strategy off-sites. We'll do reflections. And I do always check in with him. I’ll ask, what about me drives you crazy? And vice versa.

For him, it might be, the way that you work is different than the way I process things. And then my feedback to him is to give me a bit more to work with. But we don't have conflicts. It's just different working styles.

What's your plan for the future—do you plan to stay a two-person shop, scale up, or take things in a different direction?

I ask Garrett every year. Do you want to keep going? Is there anything that you would change? I was in Portland last week spending time with him and asking him if he wants to keep going. And fortunately, he said yes.

All the hypotheses that I had in terms of why I wanted to have a partner—why I wanted to do it with Garrett—have all been checked off. All of that continues to be true.

I didn’t want to do this by myself. I think it's lonely.

I wanted somebody with complementary skill sets. I really do think that in this case, one plus one equals three. We bring in different skills.

I'm really good at the hustle, business development, networking, and credibility given my 25 years in tech and venture. But there's just something that's really special about his approach, his style, the way he works, his thoughtfulness, and his wisdom.

It's all kind of played out the way I had envisioned it. So why change up what’s working really well?

Where can we go to learn more about you?

Our website is nextstepfwd.com.

But you can find us on LinkedIn: Garrett Kelly and Ha Nguyen.

💎 Last Week’s Gems

• 🧸ྀི How AI, Healthcare, and Labubu Became the American Economy (Kyla Scanlon)

• 2️⃣ Why You Should Have (at Least) Two Careers (HBR)

• 🤝 How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time (How I AI)

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hey {{ first_name | there }}, today we're talking about what gets conveniently left out of those highlight-reel LinkedIn posts.

Today, in 10 minutes or less, you’ll learn:

• 🔥 4 harsh realities not enough people talk about before going portfolio

• 💸 The hidden costs that can lead to getting stuck in the messy middle

SPONSORED

👉️ Join Our Invite-Only Community

What you’ll see when you become a Portfolio Path member!

Tired of navigating your portfolio career alone?

If you have 5+ years of working experience, join the waitlist for our invite-only community (launching August/September 2025).

🚀 Why join the community: Accelerate your learning, grow your revenue, and build genuine relationships with like-minded peers on the portfolio path

🎯 What you get:

✅ Lifetime access to Portfolio Path Community
✅ Expert fireside chats, peer workshops, & community calls
✅ 30-day challenges and group accountability
✅ Shared resource library (AI workflows, offer templates, etc.)
✅ Full access to PT Consulting Launchpad lessons + workbook
✅ Full access to Consulting Offer Blueprint

Limited founding spots available. Join the waitlist, and we'll contact you about the next intake soon!

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

🎢 4 ugly truths of the portfolio path

A quick Google search for “tech careers” returns 2,180,000 results.

FAANG career ladders, compensation schemes, “how to become X” guides, bootcamps, and countless case studies.

But unlike well-trodden tech career paths, there’s not a cookie-cutter script for building a meaningful portfolio career.

Instead, it depends entirely on you.

Your values, strengths, faults, personality, and experiences.

What’s standing in between you and Person-Path Fit is a mix of self-discovery, experimentation, financial constraints—and candidly, the cojones to act.

On the other hand, I have definitely noticed several common pitfalls that people struggle with along the way. That’s as close to a “standard script” as we can get.

In this piece, I’ll highlight 4 ugly truths about portfolio careers that not enough people talk about and what you can do about them.

Truth #1: Your income will feel volatile like entrepreneurship 📊 

Let me start with the one that hits many people hard:

Mixing finance and independent work is certainly not for the faint of heart.

Going from consistent bi-weekly paychecks to feast/famine cycles is an emotional rollercoaster.

If you’ve only worked full-time roles, then portfolio careers will seem like your “escape the 9-to-5” Get Out of Jail Free card.

My favorite Monopoly card!

But I assure you - you’ll soon realize you’ve been sorely mistaken.

Like any other entrepreneur - startup founder, solopreneur, or consultant - with a portfolio career, you’re forced to eat only what you kill. That means hunting to survive, or else risk starving out on the field.

So what’s an aspiring portfolio pather to do?

How to deal with it:

1. Follow the 1-2 Rule. If you haven’t left your FT job, shoot for 1x year of expenses saved and 2x monthly expenses from your business income.

2. Consider securing your future retirement first (Coast FIRE). Being on track for my financial goals gave me more confidence to experiment.

3. Take turns with your partner. It’s rarely discussed in public, but when I talk to couples privately, if one is pursuing a portfolio career (or entrepreneurship), the other is a spouse with FT work and benefits (see next truth).

Truth #2: Healthcare becomes a big monthly expense 🏥 

Self-employed health care is rough, especially in several mature markets like ‘merica.

If you go down the Reddit rabbit hole, you’ll see comments like one from an American self-employed couple spending ~$11k/year with a $7K deductible plan and a family of 4 is spending over $20k/year on their basic plan. 🤯 

In short, self-employed health care plans cost 2-3x what you pay as an employee.

High-deductible plans means you’re pretty much uninsured for anything under a few thousands dollars.

How to deal with it:

• Check out self-employment benefits platforms like Besolo.io. By aggregating under a national PPO, they can access better rates or networks.

• Shop for healthcare on the open marketplace

• Use international health care plans if living abroad. I used SafetyWing Complete (affiliate) for my health appointments while living outside of the US, and it’s worked smoothly while being reasonably priced ($208/mo).

Truth #3: Self-employment taxes are more complex 💰️

The first time I realized I had to make quarterly tax payments was a rude awakening.

If you’re American, (or resident of an entrepreneur-unfriendly tax jurisdiction), get ready to go down the rabbit hole of tax minimization.

I know I know, everyone’s favorite pastime!

For example, American solopreneurs get hit with the full self-employment tax (15.3% on top of income tax).

You can deduct expenses to reduce your taxable income substantially, but you’ll still pay higher Social Security/Medicare taxes than employees.

You also have to pay your estimated taxes quarterly. If you don’t, you risk penalties and interest.

There are definitely ways to minimize your tax burden through careful planning (S-Corps, Solo401k’s, expat tax exclusions) but that means spending time learning or money hiring an accountant to help you.

Ready to start talking about taxes at dinner parties?

How to deal with it:

• Set aside 15-20% of your income for taxes immediately. I setup an auto-transfer for 15% of my business income to a tax sub-account using Mercury Business (affiliate).

• Take advantage of your business deductions. Expenses like home office, software, internet, phone, travel, and even health insurance premiums.

• Get an accountant early. Did you find what I wrote confusing? Time to seek a professional to help you with 2026 tax planning.

Truth #4: Your professional identity gets scrambled 🔮 

"So what do you do exactly?"

This question used to make me break into a cold sweat.

And I’m not the only one —

Tim Huang, former PM in SF and Portfolio Path reader; Youtuber Ali Abdaal; and Andy Johns, former tech exec in Silicon Valley, all recently wrote about the challenges of leaving behind a “successful career” and reconstructing their personal sense of value and self-worth.

Here’s the harsh truth people rarely tell you:

If you’ve been high-achieving for the majority of your life, it is going to take some serious deprogramming and inner work to go from living a “successful” life to an interesting life - without hitting the abort button.

But let’s say that you’re giving it your best shot. And now you’re in the messy middle - the valley after leaving behind the last mountain peak of your career.

How do you navigate through the valley to reach the second peak?

How to deal with it:

• Discover and double down on your zone of genius. No matter your title or business, you can always count on the intersection of your strengths and what brings joy.

• Run tiny experiments. Test new aspects of your identity for 1-2 weeks instead of making permanent declarations. "I'm trying writing for 30 days" beats "I'm a writer now."

• Get creative with work arrangements. Mix consulting, FT roles, advising, and teaching. Don't limit yourself to one box just because it's easier to explain.

• Find like-minded peers. It can get lonely in the valley. Shameless plug - we designed our invite-only community exactly for this reason: to help you connect and grow with other portfolio careerists. Come join us.

The bottom line

Portfolio careers aren't the “escape the 9-to-5” dream that you see on Instagram.

They're a set of trade-offs. More autonomy and flexibility, yes. But also more uncertainty and accountability.

That’s why I strongly believe the people who thrive on this path aren’t running away from something. They’re running towards a compelling vision of work that aligns with their values.

If you're considering the portfolio path, factor in these realities:

• Build a bigger financial runway than you think you need

• Prepare for potential admin complexity (taxes, healthcare)

• Invest in systems and community to combat isolation

• Accept that you’ll likely deal with identity conflicts

However, for those who are prepared for these ugly truths?

The ability to design work around your life instead of the other way around make the challenges worth it.

I wouldn’t have it any other way.

Thanks for reading. If you’d like to grow alongside other portfolio careerists, join the waitlist for our invite-only community.

💎 Last Week’s Gems

🧩 What Gen Z’s Portfolio Careers Mean for the Workforce (Upwork)

😫 Why Are Managers So Miserable at Work? (WSJ)

📊 The Substack AI Report (Arielle Swedback)

😰 Encore Anxiety (Anu Atluru)

🤩 Community Wins

Our members have been crushing it in their 30-day lead gen challenge! Here's what's been happening behind the scenes:

🔗 Brandon → Built solid lead pipeline from networking in local startup events

🌏 Michael → Balanced cold outreach with getting a paid startup mentorship (Southeast Asia market entry)

📚 Li → Published 3-part resilience series + sent first proposals to potential clients

💡 Adi → Generated 95 content ideas + launched new consulting website

👶 Chloe → 70% book completion + newsletter launch (while new parenting!)

🎭 Hari → Led B2B Marketing Workshop for our community + pursued creative projects like busking on the streets of Dublin!

Want to join exclusive members events? Join the waitlist for our invite-only community. We’ll notify you for our next intake.

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

How are others navigating their tech careers when AI is reshaping the industry? My friend Jay’s story is telling.

Let’s dive in!

Today, in 10 minutes or less, you’ll learn:

• 🚀 Why a 15-year design veteran chose to work on a new continent & industry

• 🎯 The brutal truth about AI hype vs. what AI skills actually matter

• ⚠️ How to dodge the "vibe coding" trap and create something people love

SPONSORED

🎫 RSVP for August 7th Workshop: Offer Design 101

RSVP for the Free Workshop

Confused about how to design your first offer?

Join us for this month’s workshop on Offer Design 101 - where we’ll walk through a lightweight framework for designing & pricing consulting offers.

The Portfolio Path Workshop is a free monthly live session for those walking the portfolio path:

🌟 Senior professionals building something on the side
🌟 Portfolio careerists creating multiple income streams
🌟 Founders/consultants maximizing their time and impact

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🖊️ From Grab to AI Products at Canva | Jay Demetillo

In 2023, we featured overseas tech job search tips from Jay Demetillo, previously a lead UX designer at Grab.

This post was a hit!

Since then, he moved from Singapore to Australia to help build Canva Sheets — a top secret AI project until recently announced to the public.

Today, I’m excited to bring Jay back for round two to discuss:

• How he moved his tech career to a new market (yet again!)

• How he finds the signal amidst the noise in the AI Era - especially in navigating his own tech career

Curious about how others are navigating their tech careers in a rapidly shifting landscape? This edition is for you.

Here’s Jay:

Jay Demetillo is a design leader and consultant. He has 15+ years of experience working with tech companies such as Canva, Grab, Twitter, Pinterest, and Yahoo across the US, China, Singapore, and Australia. He was an adjunct professor at CCA in San Francisco and has taught in China for ACG.

🎨 What motivated your transition from Grab (Singapore) to Canva (Australia), and how did you position yourself for an AI-focused role?

I felt I was given an amazing opportunity to work on something totally different that could impact people at a large scale. Grab is great. I have no regrets working there. I have some amazing memories and products I’ve built there, but Canva gave me an opportunity to level up.

I’ve told other people this as well. If I were a sports athlete, I’d love a chance to play in different leagues. This is no different. Working in a different market, getting to know a new space.… it’s super fun.

As for an AI-focused role, I wouldn’t say I positioned myself for it. It just happened and I caught the wave at the right time. Being in the right place and in the right time seems to be a theme of my career.

🤖 What AI skills actually matter in building products versus what's hyped on social media?

I think it depends. AI is wonderful as a thought partner. It’s great at starting a project from the ground up, and it’s awesome at creating designs to a certain extent.

That being said, we’re now hitting the era of everyone creating their own app. To a degree that’s cool but just like when people figured out how to code their Myspace home page and show off, the shine is going to wear off.

The experience and design is going to be the differentiator with all these applications. Sure, it’s great to build something from 0 to 1 but in reality, everyone is building from 0-50 in the Age of AI. The last 50% is actually getting into the weeds, giving your users a delightful and meaningful experience that’s different from competitors.

One example I talk about is looking at the car industry. Car models were relatively similar until Tesla came around. When Tesla came out, people mocked the experience of having a large screen while you were driving, but turns out Tesla was right. This actually improved the driving experience and now you see all other car models adapting with screens as well.

So in the end, a smart and delightful design experience matter even in the Age of AI.

🛠️ What were the biggest challenges in building Canva Sheets from scratch, and how did you overcome them?

Like any other new product, there are always challenges navigating between serving users who are considered experts to certain types of experiences versus newbies. I think if you ask any product or design person, there is a balance to strike here.

How do you make your product accessible and inclusive to scale for all user types? Some people will assume AI can save you in this regard. AI cannot give you all these answers even if it does tests for you because it’s built on existing data.

You still need to talk to real users to get those on-the-ground truths or insights as user behaviors change over time whether it’s due to uncontrollable factors like the economy or tech rapidly changing. It’s happened to products I’ve been a part of whether it’s in finance, sports, ride-hailing, e-commerce, etc...

Having a proper obsession with serving your users and testing consistently when you find product market fit is the key to success.

💭 What's your reaction to trending AI developments like vibe coding? Overhyped or underrated?

Personally, I feel it’s a bit overhyped but there are some really nice feel good stories and applications that have come out of this wave of AI Development.

You are starting to see that as folks post more about their vibe coding builds on social (like when folks figured out how to build out their Myspace or Xanga back in the day). There is nothing wrong with being proud about vibe coding cool apps, but the problem now is there’s a saturation of applications.

There is no differentiation on how this product is considerably better than others. It’s really hard to tell especially when the word “AI” is thrown around and everyone assumes it must be amazing.

I’m not trying to be negative. Personally, I think it’s great to see designers (and anyone else who hasn’t coded) jump into space of building because the differentiator at the end of the day is delightful and easy to use applications.

But if you’re going to deliver true user value, the story you tell needs to change to ensure your platform is accessible and people understand it’s value for daily habits. Also what you build needs to be stable as the lack of code QA on some of these experiences is concerning.

I do predict though a lot of folks will have their own products for personal use. I think that’s awesome but if you’re truly looking to make a difference, I’d love to see more folks push for their own differentiated products and startups that makes a difference around the world.

Jay’s favorite non-human (not AI)

💡 What advice would you give to tech professionals looking to incorporate AI into their career growth?

Just jump in and don’t be scared of the learning curve. Try tools like ⁠Cursor, Claude, ChatGPT, V0, Tailwind, Railway and making AI agents through various tools.

I love that companies are giving employees a chance to figure out how to better use AI in their workflows. How are you using these abilities to speed up a project or better collaborate with teammates? We’ve just done this at Canva and it was super helpful.

I’d find the right communities of people to surround yourself with as well. Product & design people to follow: Joe Natoli, Mia Blume, Andy Budd, Harrison Wheeler, Ha Phan.

I am not part of the rah-rah AI crowd but I build on the side, at work, or for experimentation. I have my own startup ideas but I would rather build in secret instead of sharing them for now. I also surround myself with realists which has helped my perspective on AI.

If you are serious about building products with AI, put your money where your mouth is, invest in the tools, the right people, and the right messaging. As we learned anything from politics and social networking in tech, your messaging and story matters long term. Embrace AI because it’s not going away anytime soon.

🔗 Where can we go to learn more about you?

• Connect and shoot me a message on Linkedin

• Subscribe to my Substrack “The Drifting Frame”

• Get mentored by me on Mentor Cruise

• See me speak at Design Matters Tokyo

💎 Last Week’s Gems

🧒 My wife & her friend are helping kids become illustrated book authors (TIMS)

🤔 Zero-sum Thinking and the Labor Market (Kyla Scanlon)

💭 When o3 Plans Your Career Better Than You Do (Katie Parrott)

📆 Upcoming Workshops

• August 7th, 6pm PST / 9am SGT: Offer Design 101 → Register

• September 4th, 6pm PST / 9am SGT: Growth Engine 101 → Register

• October 2nd, 6pm PST / 9am SGT: TBD → Register

Want replays? You can access our vault of workshop recordings here.

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

Today’s edition is about the tango between two of my favorite subjects - personal finance and a portfolio path.

Let’s dive in!

Today, in 10 minutes or less, you’ll learn:

• 🧠 Financial independence vs financial flexibility

• 💰 Why Coast FIRE helped unlock my portfolio career

• ❓ Three questions to separate money anxiety from actual financial constraints

SPONSORED

🤩 Apply to Portfolio Path Membership

What you’ll see when you become a Portfolio Path member!

Tired of navigating your portfolio career alone?

If you have 5+ years of working experience and are building a portfolio career, apply to join our invite-only Portfolio Path Membership - launching August/September 2025.

• 🚀 Why join the community: Accelerate your learning, grow your revenue, and build genuine relationships with like-minded peers on the portfolio path—so you can go further together than solo.

• 🎯 What you get: Monthly community calls, expert fireside chats, 30-day challenge, accountability buddies, and shared resource library.

• ⏰ Why now: Early members lock in founding member perks and the best lifetime rate.

We can't wait to meet you!

Limited founding spots available. Apply now, and we'll contact you with more information soon.

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

🔓️ How to financially unlock your portfolio path

In 2023, I left my last full-time tech job.

This means I’ve been working independently for the last 2 years. (time flies!)

But before pulling the trigger, I assessed factors like my personal finance goal:

Did I feel financially secure enough to take a risk?

If you’re like me and the hundreds of professionals I’ve spoken with, you want to avoid getting yourself into a tough spot financially:

Here’s the conventional wisdom online:

Save aggressively until you hit financial independence. Then you are free to do whatever the hell you want. (In my 20’s, I bought into this.)

But I realized something recently:

Financial flexibility is very different from financially independent. I wasn’t FI, but that didn’t mean I wasn’t secure.

In this edition, I define financial flexibility vs financial independence, why I chose Coast FIRE, and 3 questions to ask yourself to financially unlock a portfolio path.

💰 Financial flexibility vs financial independence

Nick Maggiulli, personal finance blogger and COO of Ritholtz Wealth Management, recently wrote about the differences:

• Financial Independence (FI) is when you reach a level where the income generated from your investments and assets can pay for your lifestyle expenses without your needing to work.

• Financial Flexibility is about having options with your money. You don’t need FI to have financial flexibility.

For a long time, I chased financial independence.

But in my early 30’s, I began to question if it was the right goal for me - and asked myself why.

After reflecting, I realized that growing up in a financially unstable household led me to latch onto the idea of FI. It felt safe. Comfortable. Freeing.

Most FI people I meet don’t use flamethrowers. (Credit: NYT)

But I also felt skeptical:

On one hand, I've met professionals who hit FI, allowing them and their families to live their rich life. When executed well, it’s awesome.

On the other hand, I've watched others obsess over their FI number - to the point of sacrificing relationships, health and fun.

That’s when I started to separate the notion of financial security from 100% financial independence.

Enter Coast FIRE.

🌊 Why Coast FIRE unlocks options

I forget where I heard about Coast FIRE, but it shifted my perspective.

Coast FIRE means having enough invested that your current portfolio will grow to cover your future retirement - without adding another penny.

Unlike traditional FI, you don’t need to focus on aggressively saving until you achieve retirement.

Instead, you just need to cover your life expenses through work you enjoy.

Credit: Money

To be clear, you don’t get to stop working like FI.

However, you get more flexibility to switch to lower-paying but more meaningful work, start a business, or even pursue a portfolio career.

This resonated with me deeply.

I love working. It brings me a sense of purpose and I can’t imagine stopping for the sake of retirement.

But at the same time, I wanted greater career and life flexibility.

📊 How the math works

I used this online calculator to calculate my Coast FIRE number.

You need to input assumptions like age, annual spending, monthly contributions, growth rate, and inflation rate.

What I used:

• 7% investment growth rate

• 3% inflation rate

Here's an example of what a 31-year-old expecting to work until their mid-60’s would need to invest to hit CoastFIRE:

🧠 The psychological shift I made

Something clicked when I ran my Coast FIRE numbers.

It sounds silly, but I felt the pressure I put on myself vanish.

For the first time, I could separate my current income needs from my long-term retirement.

I obviously still needed to cover rent, food, and daily life expenses. But I didn’t need to optimize for maximum wealth accumulation.

This realization helped me give myself permission to run experiments. To make career decisions irrespective of money.

That’s when I launched the expat money newsletter and took on a couple of startup advising gigs.

None of these moves would have made sense if I was chasing FI.

🚧 The real barrier is not money

Now, I realize that the biggest obstacle to pursuing a portfolio path isn't money. It's the story we tell ourselves about money. (Plus, identity.)

Many professionals think they need complete financial independence before they can explore alternative career paths.

But that's a perfectionist myth.

The truth is simpler:

You need enough financial security to responsibly experiment without risking your daily lifestyle needs.

But beyond that, you have quite a bit of flexibility.

📝 Three questions to ask yourself

And if you're still feeling stuck, consider these other questions:

1. First, what's really driving your fear of pursuing something unconventional? Is it actual financial constraints, or anxiety about what might happen?

2. Second, does financial security need to mean complete financial independence for you? Or could it mean having enough flexibility to take thoughtful risks?

3. Third, if you reframed your goals around financial flexibility rather than financial independence, what would become possible?

These questions helped me change my relationship with fear - especially around money.

Hopefully they help you too.

🛤️ The path forward

Reframing financial independence as financial flexibility opened new doors for me.

Here’s what we covered:

• Financial independence vs financial flexibility

• Why Coast FIRE unlocked options

• How to calculate your Coast FIRE number

• The psychological shift I made

• The real barrier isn’t money

• Three questions to ask yourself

But ultimately, this is just my story.

I look forward to hearing about ways you find to financially unlock your portfolio path.

What’d you think of this piece? Reply and let me know your thoughts - I read every email.

💎 Last Week’s Gems

✈️ The Death of the Amex Lounge: Why the Upper Middle Class Isn’t Special Anymore (ODAD)

🧑‍💼 Are middle managers reconsidering what a fulfilling career looks like? (LinkedIn)

🧰 Curious Beginner’s Guide to AI Agents (Peter Yang)

🤩 Community Spotlight

If you've been considering joining the Portfolio Path Membership, now is the time. We have so many great speakers coming in to share their knowledge.

This week? Makar Stetsenko, Fractional CTO & cohort alum, is showcasing exactly how he landed his second fractional CTO client in just a few weeks.

Apply to Portfolio Path membership and come join events like this LIVE. We’ll be addressing Q&A from specific members on this call.

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

Back in CDMX! Recently, many of you voted for learning more about future-proofing your portfolio career with AI. 🤓 I’d love to hear about how you’re using AI:

Today, in 10 minutes or less, you’ll learn:

• 🤖 Why "What can I optimize with AI?" is the wrong question

• 🧠 How to envision your ideal team (then build AI to match)

• 🏗️ How to build workflows that handle boring tasks while you create

• 📝 Real example: Voice notes → newsletter briefs automatically

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With Attio, AI isn’t just a feature—it’s the foundation.

• Instantly find and route leads with research agents

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• Build AI automations for your most complex workflows

• Join fast growing teams like Flatfile, Replicate, Modal, and more.

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To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

🏗️ How to scale yourself using agentic workflows

“What can I optimize with AI?”

Everyone’s asking this question, but it’s too tactical.

The danger is climbing the wrong mountain - instead of tackling the bigger problem:

I spent years working with teams automating financial operations. And boy, let me tell you - nothing feels shittier than wasting months automating the wrong process or one you didn’t need in the first place!

Instead, ask yourself a broader question:

“If I had unlimited resources, who would I hire?”

Inspired by Khe Hy’s post, I asked myself this question for my portfolio career education business.

Not only was it a fun exercise, but it was clarifying.

I envisioned my ideal team, then built a bridge backwards to the incremental changes needed.

One more thing - don’t worry if you’re not technical.

While I use Make the most, tools like Relay.app, Lindy (and n8n for more technical folks) are making it easier than ever to build agentic workflows.

In this edition, I’m going to show you step-by-step how I designed my dream team, re-imagined my newsletter writing process, and started implementing an agentic workflow.

My Dream Team

Currently, I have two part-time team members:

• Thao - helps run our cohort program and community

• Trang - my exec assistant supporting me across the business

They’re doing great work (and leveraging AI).

My aspiration is to build a hybrid dream team - humans + AI working together in concert.

And so I answered the question “who else would I hire?”, and came up with the following specialist roles:

• Newsletter writer and editor

• LinkedIn writer

• Graphic designer

• Slide creator

• Customer researcher

• Event coordinator

• Marketing email creator

• Sales page creator

• Client testimonial coordinator

Let’s pick one that I came up with - Newsletter writer.

Now I’ll walk you through how I ideated a broader vision, then broke it down into agentic workflows.

Let’s demystify some jargon first:

🧑‍🍳 What the h*ll is an agentic workflow?

Recently, we watched Culinary Class Wars, a Korean cooking reality competition show. It’s fire 🔥 . Highly recommend.

So I’m going to use cooking as an analogy:

• Workflows = following a step-by-step recipe

• Agents = head chef in a kitchen adapting to available ingredients

• Agentic workflows = some steps are handled independently by assistant chefs, still guided by the head chief

While you can find heaps of sexy “AI agent” marketing demos on Linkedin, the reality is they’re difficult to run as 100% autonomous workers due to challenges like accuracy, security, and cost.

Enter agentic workflows.

They allow you to start making changes right now.

📝 How do I write newsletters today?

I feel a bit embarrassed to admit that feel like I’m constantly wrangling with my newsletter writing process.

It has never felt like a goldilocks “just right.”

But I’m going to give it to you straight anyway.

How I get my newsletter ideas:

• Shower thoughts or walking in the park

• Talking to readers, friends, and my wife

• Interesting quip or article I read online

• Life event that happened

After this, I plan out the newsletter using a Notion content brief:

Then, I open up Beehiiv, load up a newsletter draft template and use this as my main workspace:

• I start with a title, deep dive intro, and key bullets for the body.

• Meanwhile, my assistant helps me design a newsletter thumbnail and populates the Last Week’s Gems and other sections.

• Once I have a draft, I write the newsletter intro bullets (“here’s what you’ll learn:”) and drop in graphics.

• Finally, I get feedback from my wife or a friend, edit everything, and hit schedule.

That’s the process in a nutshell. Altogether it takes between 2-14 days to publish.

Here’s everything distilled into a tidy 6-step diagram:

Thanks Claude + Mermaid Charts

🎨 How would I re-imagine this workflow?

This is where I start dreaming up new possibilities:

Step 1: Brainstorming ideas

• Record and transcribe voice notes while on-the-go (Voicenote)

• Summarize raw notes into structured output (Claude)

• Attach the summary to a new Claude Project

Step 2: Planning the newsletter

• Pre-fill Notion content brief using my voice note summary (Claude + Notion MCP)

• Automatically generate Notion page in my Content Calendar

• “Pitch” newsletter to an AI editor to get feedback (Claude)

Step 3: Drafting newsletter content

• Generate outline based on my content brief and RAG of past newsletters (Claude)

• Then I write the deep dive draft manually

• Insert memes/image using an AI-based search or meme generator tool

• Draft intro (“This week you’ll learn”) using generated bullets (Claude)

• Draft other sections (“Community"”) by summarizing raw bullets/notes (Claude)

Steps 4-5: Editing and feedback

• Revise and edit the newsletter draft using LLM feedback (Claude)

Note: I do not want AI to automate my actual writing.

However, I do want AI to automate away the repetitive bits (operations) around my core creative work (writing).

Now, let’s get to how I turn this vision into actual agentic workflows:

🗣️ Example: Voice note → content brief generator

Let’s say we want to automate Step 1: Brainstorming Ideas.

Here is how I would setup an agentic workflow in Make:

• Trigger → During my walks in the park, I open up Voicenote and hit record. Once the note is created, this triggers a Make automation via webhook

• Action → Then Make prompts Claude using the transcript (or summarized notes) to output a pre-filled Notion content brief template

• Output → Make Slackbot asks me to approve the pre-filled content brief - “approve” or “no.” If not approved, Make repeats the previous action again to generate a new content brief

• Output → If approved, it creates a new page in my Notion Content Calendar and appends my pre-filled content brief. Then I start writing my draft outline

To be clear, I haven’t setup this automation yet (that’s this week :)).

But if this works as expected, it could save me ~30 minutes of planning per newsletter or ~26 hours every year. Not bad.

And that’s only Step 1.

I hope I did a decent job of showcasing why you stand to gain a lot from doing this exercise!

🏁 Wrapping up

That was fun. Today we showed you how to scale yourself by envisioning your dream team, re-imagining your workflows, and implementing agentic sub-flows.

Want to try this exercise out yourself?

Here’s your next steps:

1. Ask yourself, “If I had unlimited resources, who would I hire?”

2. Brainstorm specialist roles you’d like to hire

3. Pick one of the roles and design an ideal agentic workflow

4. Bridge backwards to identify sub-flows you'd implement

5. Build a simple version this week using Relay.app or Make

This is only the beginning. Have fun building!

Thanks for reading. What agentic workflow are you going to build? Reply and let me know! I respond to every email I get.

💎 Last Week’s Gems

• 💪 Here is how I approach starting a new job (Elena Verna)

• 🤔 Why ‘Success Is Quieter’ for Younger Americans (WSJ)

• 💭 My $2,400 failure of imagination (Khe Hy)

✨ Join Our Next Workshop

• Next Workshop: August 7, 2025 6pm PST / 9am SGT → Register Here

• Get Past Replays: You can access our vault of workshop recordings here

Dexter Zhuang
Say hi 👋 on LinkedIn or Substack Notes
🚀 Partner with Portfolio Path

Hi {{ first_name | there }},

I’m taking this week off to celebrate 4th of July and my wife’s birthday with family. 🥳 

If you’re looking to learn something in the meantime, I encourage you to dive into our newsletter archives.

Enjoying homemade Shanghainese food 🥘 

And if you’re up for weekend reading, here’s a few gems:

• Why financial independence is overrated (but Coast FIRE is a great alternative)

• How I stopped worrying about AI and learned to value my humanity

See you next week!

Dexter

Hello from Traverse City, Michigan! Growing up, I wanted to get out of Michigan as quickly as possible. Now we love spending part of our summers here.

Change is also the theme of this edition. Let’s dive in.

Today, in 10 minutes or less, you’ll learn:

• 🎭 Why "So what do you do?" becomes your worst nightmare after quitting

• 🧰 7 unconventional tools to rebuild your identity beyond job titles

• 🔬 How to run "tiny experiments" to discover what actually makes you come alive

SPONSORED

🎫 RSVP for our July 3rd Workshop: Tech Portfolio Careers 101

Wondering if a portfolio career is for you?

Join us for this month’s workshop on Tech Portfolio Careers 101 - where we’ll showcase real-life examples of tech workers building portfolio careers.

The Portfolio Path Workshop is a free monthly live session for those walking the portfolio path:

🌟 Senior professionals building optionality into their work
🌟 Portfolio careerists creating multiple income streams
🌟 Founders/business owners maximizing their time and impact

Only 15 seats available for this session.

Sign up now:

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🪞The identity crisis no one warns you about when you quit

"So what do you do exactly?"

In 2019, this question made me break into a cold sweat.

I had just left my full-time SF tech job to travel the world, and my parents were convinced I'd become unemployable forever.

Every month, they'd call asking when I was getting another "real job."

Up to that point, so much of my identity had been wrapped up in being a “PM at Dropbox.” I didn’t know who I really was because I hadn’t carved out space to allow my own dreams to percolate.

I’d be lying to you if I said I didn’t feel anxious, self-doubt, and like I was making a huge mistake.

Fast forward to 2023. I left my Singapore tech job again, this time to build my own business and creative projects.

When industry associates and VCs questioned, "so what are you doing exactly?" I just shrugged.

This time, I felt more comfortable in my own skin.

What changed? Well, to start I learned about untangling my self-worth from my work.

But the real breakthrough was learning about the importance of Person-Path Fit.

In this newsletter, I'm sharing the tools that helped me (and dozens of others) navigate this identity shift towards Person-Path Fit after leaving a full-time role.

🤝 It’s an identity party

After chatting with readers and researching online, it’s clear I’m FAR from being the only one grappling with identity when faced with many different paths in front of me.

Take:

• Tim Huang, former PM in the Bay Area and Portfolio Path reader, shared that after leaving his full-time role to travel, “the hardest part was learning to stay indifferent to other people's expectations, so I could figure out what I actually care about.”

• Youtuber Ali Abdaal wrote about his struggle with what to call his identity after he quit his high-prestige job as a doctor.

• Andy Johns, former tech executive in Silicon Valley, wrote about leaving behind his highly successful tech career and learning how to reconstruct his sense of value and self-worth.

• Here’s a Reddit thread from a tech leader echoing the above:

And that’s just the tip of the iceberg.

But let’s say that you’re in the messy middle - stuck in the valley after leaving behind the last mountain peak of your career.

How do you navigate through the valley to reach the second peak?

After going through this twice myself and talking to dozens of others, I’ve found a handful of tools to be powerful:

🧰 An unconventional toolkit for identity shifts

First, you’ve probably heard the standard fare like “lean on friends and family”, “get a hobby”, “build a side hustle,” yadda yadda… So I’m not going to talk about those.

Instead, let’s get into the non-obvious stuff:

Tool #1: Self-reflection

As you can probably tell from my last edition on AI prompts for career coaching, my favorite questions zoom in on clarifying your strengths and curiosities — key ingredients of your Zone of Genius:

When I left my SF tech job, I realized I had perceived my Zone of Genius only in the context of one company for the past 4 years. Now it was a chance to redefine what it was for a broader industry over the next 4 years.

👉️ Try out exercises like:

1. Strengths: “Think back to 3-5 experiences when you felt like you were thriving. Write down what happened in each experience, then identify the strengths you were exercising in each story.”

2. Curiosities: “What are the problems you’re obsessed with solving?” “Why are they so interesting to you?”

This works because often we struggle to identity our own attributes, but can easily recall experiences when we felt the most alive.

If you want to supercharge these exercises with AI, grab my free prompts here.

Tool #2: Peer feedback

I’ve also found it very helpful to get a trusted friend or colleague to share how they perceive my strengths.

👉️ Try sending these questions to a friend:

1. “What do you see as my strengths?”

2. “What can you imagine me doing that would utilize these strengths? It doesn’t have to be a job title.”

Sometimes we have total blind spots. And our closest circle can just see things that we can just can’t.

Tool #3: Social validation

A FAANG product manager who left his job recently shared with me that connecting with others in the midst of similar transitions helped him validate his new path.

👉️ How to get this validation:

1. You can join communities of entrepreneurs, career changers, and portfolio careerists (like our very own!)

2. Share your on-going tiny experiments (more on this below) and get feedback

3. Collect insights on how your peers are approaching their tiny experiments, informing your own direction

4. Hire a coach who is a few steps ahead of you

Unlike only asking for peer feedback, this is much more focused on your experiment hypotheses (and theirs). Instead of reflecting on the past, it’s more forward looking.

Our new community! Apply here

Tool #4: AI brainstorming

Additionally, you can leverage your favorite LLM to pick up blind spots, share feedback, or generate new ideas. This works especially well if you’re using one with long-term memory.

Or once you have greater clarity on your strengths, you can do some fun stuff.

👉️ Try this prompt:

If you want to play around further, you can grab more of my AI prompts here.

Tool #5: Identity expansion

Many tech workers are also struggling with fear of AI.

And if you believe AI is inevitable, then this is something we’re all going to have to deal with whether we like or not.

Julie Zhou, former VP Product Design @ Facebook, suggests focusing on identity expansion instead of attachment instead:

While her advice is targeted towards adapting to AI, substitute “tools” for “job title” and these lines apply quite nicely.

Tool #6: Tiny experiments

Many high-achievers I know struggle with “all or nothing” thinking.

Anne-Laure Le Cunff, neuroscientist and founder @ Ness Labs, suggests that instead of setting rigid long-term goals about who you "should" become, start with small 1-2 weekly experiments.

👉️ Try these 3 steps:

1. Design the action: Define the hypothesis.

2. Set a specific number of trials: Run the test multiple times to collect enough data and see if there’s anything interesting to learn from it, e.g. do you actually enjoy writing or was it just that 1 time?

3. Collect the data: Do [the action] for [a set duration of time].

This experiment recipe gives you a great tool for testing different aspects of your identity to help you move towards Person-Path Fit (e.g., "I'll try writing daily for 30 days to see if I actually like writing.").

The data is your internal feelings - do you feel a sense of joy doing the activity?

I haven’t read Tiny Experiments yet, but heard good things.

Tool #7: Creative work arrangements

Finally, crafting a unique work structure that fits you can be powerful.

Elena Verna, Head of Growth at Lovable, writes about how when she decided to go full solopreneur, “stepping out on [her] own was brutal on [her] identity.”

However, she derisked by crafting a unique work structure that mitigates the risk that her experience languishes (therefore her credibility):

1. Structuring her advising work to maximize learning

2. Taking on full-time roles but as an interim leader (predetermined end date)

3. Creating alternative income streams to smooth out pipeline volatility

At Portfolio Path, we don’t believe in limiting ourselves to just “consulting.” Consider the full menu of options - FT work, fractional, teaching, etc.

Don’t be afraid to get creative.

In Summary

Quitting your high-powered job often triggers an identity crisis no one warns you about.

But this uncomfortable valley between career peaks is actually the perfect time to explore your Person-Path Fit.

We walked through 7 unconventional tools to help you go beyond the job title and discover who you really are:

1. Self-reflection

2. Peer feedback

3. Social validation

4. AI sounding board

5. Identity expansion

6. Tiny experiments

7. Creative work arrangements

Remember - the goal is NOT to identify another dream job title.

It’s about expanding your identity beyond the socially acceptable constructs (like job titles) and reveal what actually makes you come alive.

That’s what real success feels like to me.

Thanks for reading! Are you going through an identity shift? Reply and let me know how it’s going. I response to every email.

💎 Last Week’s Gems

🚀 When are the best and worst times to join a startup? (Dan Hockenmaier)

🤖 When AI Has Better Taste Than You (Julie Zhou)

🤯 A solo founder just sold his 6 months old AI startup for $80M (Substack)

👫The Separate + Joint Method: How My Spouse and I Manage Our Money (ODAD)

✨From Our Community

• Join our Community Beta: Apply to join our upcoming invite-only community beta → Apply Now

• Get Past Replays: You can access our vault of community call recordings here

💌 Reader Notes

Dexter Zhuang
Say hi 👋 on LinkedIn or Threads
🚀 Partner with Portfolio Path

Hello from SF! We’re here celebrating a friend’s birthday, then visiting family in Michigan for the next 2 weeks.

This edition will be on leveraging AI for your (portfolio) career discovery and growth. Let’s dive in!

Today, in 10 minutes or less, you’ll learn:

• 🤖 6 AI workflows to tackle your biggest career roadblocks

• 🎯 How to use ChatGPT as your career coach

• 🚫 What NOT to use AI for in your career journey

SPONSORED

🔥 Last Call: Join Portfolio Circle Beta

Limited Seats. Apply Now.

In the past few days, we’ve welcomed amazing folks to the Portfolio Circle community like:

A fractional CFO for climate tech, former Google sales leader, 4x entrepreneur, and B2B product manager… and many more!

Apply now to join our invite-only Portfolio Circle beta launch before it closes for the summer:

🚀 Why join: Accelerate your learning, grow your revenue, and build genuine relationships with like-minded portolio pathers—go further together than solo.

🎯 What you get: Monthly community calls, expert fireside chats, 30-day challenge, accountability buddies, and shared resource library).

⏰ Why now: Beta members lock in founding member perks and the best lifetime rate when we open to the public this fall.

Beta spots are very limited (2/3 full already).

Applications close 5pm PST Wednesday June 23rd:

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

🛡️ Future-proofing your portfolio career with AI

In my late 20’s, I felt like I had hit a wall in my tech career.

I had spent my career thus far pursuing other peoples’ definition of success, but hadn’t looked inward enough to gain clarity of my own success criteria.

I felt frustrated and lost.

But the silver lining of this moment was uncovering a treasure chest of career tools that I use to this day (and also used to help guide tech workers at companies like Meta, Google, Amazon, and Square in their careers).

Now these tools can be supercharged with AI.

Last month, we published editions focused on leveraging AI in your job search (Chris Ming) and landing your first consulting client.

Whether you’re building a portfolio career or not, the future might be looking increasingly uncertain due rapid AI and technological disruption, economic shifts, and changing social norms.

So how do you adapt?

Today, we’re going to show you 6 AI workflows that you can use to help you unlock clarity in your career discovery and accelerate your career growth.

Let’s get into it:

🔮 Career Discovery

“I don’t know what I’m good at”

Understanding your strengths is mission-critical to making good career decisions. Not knowing what you’re good at is like throwing darts with a blindfold on.

👉️ Try these exercises:

1. Think back to 3-5 experiences when you felt like you were thriving. Write down what happened in each experience, then identify the strengths you were exercising in each story.

2. Ask a few people in your circle who know you from various aspects of your life for feedback — including your friends, family members, colleagues, and mentors: “what do you see as my strengths?” and “what career paths can you imagine me doing that would utilize these strengths?”

3. Finally, upload all your reflection/peer interview notes to ChatGPT and input this prompt:

“I don’t know what I want to do”

Struggling to figure out what career path to pursue? Sometimes, we have blinders on due to the role or company we work in.

I personally find it useful to periodically zoom out and think big picture about my career direction. Having a career coach - or AI sounding board - can help trigger fresh ideas you previously wouldn’t have thought of.

👉️ Try this prompt:

After you get the results, pick the ones you’re interested in pursing and setting them to the side.

In the next workflow, you’ll learn how to find people on these career paths and use their feedback to validate your career experiments.

“I don’t know whether or not I’d like this career direction”

When I talk to folks stuck at an impasse, I often suggest running career experiments.

What I mean by this is to define a hypothesis about what’d you like - perhaps it’s a new role, business, or employer.

Then validate this hypothesis by either (1) talking to someone a few steps ahead of you or (2) working on a small project in this new direction.

👉️ Try this workflow:

1. Use Happenstance (free) to conduct an AI search on your Linkedin and Google Contacts network. E.g. if you’re looking to break into climate tech, you can search for “climate tech operators” and find out who in your network.

2. Write a short outreach message either using our 11 proven email & DM scripts or Claude. Hint: Leverage commonalities you share like same school, job, etc.

🚀 Career Growth

"I don't know which skills to prioritize"

Let’s say that you realized you’re super excited about transitioning into the AI software industry. But your background is primarily in health tech.

How do you know which specific skills you’re missing? And how do you build them?

👉️ Try this prompt:

"I can't see my blind spots or growth areas"

Sometimes we're too close to our own performance to see the harsh truth.

This is a good use case for AI can help synthesize feedback from multiple sources to surface insights you might miss.

👉️ Try this prompt:

"I struggle to position myself uniquely in the market"

Standing out in a crowded market is hard. Think of it like selling a product — except the product is yourself.

Similar to packaging a product, this requires understanding both your unique value and what the market needs.

👉️ Try this workflow:

First, answer the following reflection questions (I used to share a version with career coaching clients):

1. Your unique selling proposition: What specific value do you bring that other candidates don't?

2. Employer needs: What gaps is the employer trying to fill with this role?

3. Market research: What are are the strengths, weaknesses, and experiences of other candidates for this role?

4. Competitive advantages: What are your top 2-3 superpowers that make you stand out?

5. Packaging: How do you package yourself in a convincing, understandable way for employers?

Next, grab a link to your desired JD, attach it and your notes into ChatGPT, and try this prompt:

❌ What not to use AI for

While AI is amazing, I don’t recommend relying on it for EVERYTHING:

• Relationship building: Nothing replaces genuine human connection and creating trust.

• Final decision-making: Use AI for synthesis annd generating ideas, but make major career moves with your own critical thinking.

• Replacing human feedback entirely: AI can synthesize feedback, but can't replace seeking out real mentors and peers.

• Treat AI like a smart intern: It’s not a genius. Always review and customize the output.

💡 In Summary

In my late-20’s, I spent many months on trial and error with career discovery. But with the tools we have now, career clarity might’ve come faster.

In this edition, we covered 6 AI-powered workflows to tackle the most common career roadblocks:

• “I don’t know what I’m good at”

• “I don’t know what I want to do”

• “I don’t know whether or not I’d like this career direction”

• "I don't know which skills to prioritize"

• "I can't see my blind spots or growth areas"

• "I struggle to position myself uniquely in the market"

Start with 1 pain that resonates with you. Pick a workflow. Test it out this week.

We live in more volatile times than ever, but the flip side of the coin is that we can leverage insight-triggering tools to adapt.

Don’t use AI to make career decisions for you, but do leverage it as your thinking partner to navigate uncertainty with more confidence and speed.

Thanks for reading! Which AI workflow will you try first? Hit reply and let me know.

💎 Last Week’s Gems

🧠 ChatGPT's Impact On Our Brains According to an MIT Study (TIME)

💭 The Next Great Distribution Shift (Substack)

🤔 Hybrid Still Isn't Working (HBR)

👪️ The Portfolio Career That Made Him a Better Parent | Ben Erez (Dad of 1, PM Coach/Product Advisor) (Youtube)

✨From Our Community

• Join our Community Beta: Apply to join our upcoming invite-only community beta kicking off June 23, 2025 → Apply Now

• Get Past Replays: You can access our vault of community call recordings here

💌 Reader Notes

Dexter Zhuang
Say hi 👋 on LinkedIn or Threads
🚀 Partner with Portfolio Path

Hi {{ first_name | friends }},

It’s a beautiful day here in Mexico City. I love our global community - spanning SF, NY, Singapore, London, Sydney, and more. Today's story perfectly highlights this cross-cultural energy.

Quick favor - I’m writing a piece on career identity shifts. If you have recently left a FT role and grappled with your identity, hit reply. I’d love to hear from you.

Today, in 10 minutes or less, you’ll learn:

• 🕺 How a former pro breakdancer pivoted into healthcare and built a 6-continent career

• 🎯 The exact steps he took to turn organic conversations into board advisory roles

• 💼 How he structures his consulting deals that work for both cash flow and equity upside

SPONSORED

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Limited Seats. Apply Now.

Tired of navigating your portfolio career alone?

Apply to join our invite-only Portfolio Path Community beta launch - launching June 23, 2025.

🚀 Why join: Accelerate your learning, grow your revenue, and build genuine relationships with like-minded peers on the portfolio path—so you can go further together than solo.

🎯 What you get: Monthly community calls, expert fireside chats, 30-day challenge, accountability buddies, and shared resource library.

⏰ Why now: Beta members lock in founding member perks and the best lifetime rate when we open to the public this fall.

Beta spots are very limited.

Applications close 5pm PST Wednesday June 18th:

To get your brand in front of 7k+ professionals, founders, and consultants, fill this out and let's chat.

🌍️ From pro breakdancer to Oxford EIR | Benny Axt

Since starting this newsletter, I’ve been proud of featuring stories of amazing portfolio careers across tech, finance, and health.

This time, I’m excited to spotlight Benny Axt, a healthcare leader who has led an adventurous, impactful global career—while building an impressive portfolio of board advisory and consulting clients.

Benny and I connected as Dartmouth alums and expats (naturally diving into the fun world of international taxes 😂)

One fun fact from our chat:

He had a 1-year stint as a professional breakdancer in South Korea before he launched his career in health care!

In the past few weeks, I’ve been gently nudging him to come and share his story with our Portfolio Path readership.

I’m very happy that we finally roped him in - just in time to announce this feature in lockstep with him launching his next chapter at Oxford.

Without further ado, here is Benny:

Benny Axt is an Entrepreneur in Residence in the Health Tech team at Oxford Science Enterprises (OSE), the largest university-affiliated investment company in the world. As a seasoned healthcare strategist, operator, and corporate development leader, he has spent over 15 years building health care businesses across 6 continents.

His experience experience includes scaling venture-backed start-ups, leading strategic turnarounds, guiding international expansion strategies, and supporting IPOs. In addition to his role in venture capital, he serves as a board advisor and healthcare consultant to leaders who seek guidance with healthcare strategy, operations, project and program management, and international expansion.

You’ve had 15 years of experience building healthcare businesses across 6 continents. How did you first get into health care, then grow your career?

I spent half a dozen years working around the world after university—a year in Asia, one year in Africa, and several years in South America. After returning to the US, I pursued an international MBA to build a stronger professional toolkit around my disparate global business experience.

Before starting the MBA, I spoke with an alumnus of my b-school who ran a boutique consultancy. He offered me a position as a consultant in his firm. Many of our engagements focused on healthcare and life sciences—it helped that his dad was the head of infectious diseases at the Mayo Clinic.

When I finished the MBA, I was recruited to join the DaVita Redwoods MBA Leadership Program. Initially, I was an operator in the Bay Area.

In 2014, an opportunity arose to support DaVita's International CEO with a historic contract in the Kingdom of Saudi Arabia (KSA). As the Kingdom sought to privatize healthcare services, DaVita won the largest healthcare delivery tender on record, supporting half of the end-stage renal disease patient population.

I was one of the first expatriates on the ground and had a hand in building the infrastructure, services, and team to execute the contract. Our success in the Kingdom helped launch my global healthcare career, which has given me opportunities to work in healthcare systems on six continents.

In addition to being an entrepreneur and operator, you’re a board advisor and healthcare consultant. What was the key turning point that made you decide to pursue these opportunities?

I had a unique vantage point into the North American health tech ecosystem while working as the Vice President of Strategy for Dialogue Health Technologies Inc., one of the largest healthcare technology companies in Canada. In addition to strategy, I oversaw corporate development and innovation while supporting the CEO as Chief of Staff. I joined the company during the scale-up and was part of the 6-person leadership team.

This experience gave me a chance to connect with people across the health tech ecosystem such as investment bankers and healthtech CEOs. In many of my interactions, I heard consistent pain points that I had personal experience solving—such as how to guide international healthcare companies on US market entrance, challenges with innovation and product market fit, and cohesion among C-level teams.

Following these conversations, I often found myself sharing articles or posts that I had written on a certain topic. I would then be asked to structure a proposal to help provide support on the issue. The business development began organically and it quickly became clear that I should put more thought into establishing a more formal consulting practice.

What was the process like for getting your first board advisory positions?

My first board advisory role was the result of a relationship that I cultivated in a McKinsey forum attended by various healthcare leaders from around the world.

I formed a quick rapport with Mark Wien, the CEO of PocketPatientMD (PPMD). We spent time on the sidelines discussing Africa and the various opportunities and challenges he was facing to scale his digital platform in low- and middle-income countries. We had several conversations thereafter, which culminated in a board advisory arrangement.

One opportunity can serendipitously beget another. As part of my board work with PPMD, I cultivated a friendship with another PPMD board advisor who is a Gambian pulmonologist in West Texas. He plans to return to The Gambia in a few years and contacted me to help him think through development of a hospital and the launch of a medical education service line. The timing of his call came just before I started a Master program at Dartmouth. I pulled together a Dartmouth consulting team to provide support and was offered a board advisory position.

Another opportunity came through a word-of-mouth recommendation from a former colleague in Germany.

How did you structure your consulting offers at first? How about now?

When I began my consulting practice, I focused on a typical fee-based, cost-plus consulting model. I often asked for an upfront retainer and milestone-based payments throughout an engagement.

Board advisory work differs. My brother-in-law works at the Founder's Institute and I've always been a fan of their Founder / Advisor Standard Template (FAST Agreement) for structuring equity-based compensation. Over time, I've adopted a hybrid approach with cash and equity, though I tend to structure most consulting engagements with an approach that skews more heavily towards cash-based compensation.

Ultimately, I try to remain flexible and structure engagements in accordance with the needs of the CEOs that I serve.

Balancing multiple commitments is a challenge for many of our readers. Can you walk us through how you developed your consulting practice while still maintaining executive roles?

When I was pondering the launch of a consulting practice, I reached out to a mentor of mine in the UK who sits on various boards across the world. 

His responsibilities extended far beyond the corporation where he worked so I was curious about how he had structured an effective agreement which allowed him to take on external work. 

He opened my eyes to possibilities that I hadn’t considered, such as negotiating external consulting hours into an employment contract. Generally speaking, these conversations need to happen in advance of starting any new position with clearly aligned contractual covenants (e.g. non-competes, scope, hours, etc.).

I’m a naturally gregarious person and I strive to maintain relationships. For example, I have a personal goal to meet with 500 new people over the next year.  As a head nod to the book Your Network is Your Net Worth by Porter Gale, I’ve often found that second and third degree connections are most effective for surfacing opportunities.  

What advice would you give to senior professionals looking to build a portfolio of consulting and advising work like yours?

A few things to consider: 

1. It can take years to build a book of business so have patience when you launch and get creative about initial leads. For example, if you are just starting out, you can gain some experience providing your services via accelerators or entrepreneurship centers at different universities. These organizations may not be commercially lucrative out of the gate, but you will have a chance to hone your craft and build an initial book of business.  Serving as a mentor in these types of programs is also a wonderful way to meet entrepreneurs and develop some brand equity in your area of expertise.  

2. Social media is a critical vehicle for personal branding. My preferred medium is LinkedIn. I suggest starting with one channel and mastering that channel before taking a multi-pronged approach.

3. Never underestimate your value! Everyone has unique skills so know your value proposition and don’t sell yourself short on the tremendous gifts that you are bringing to the world.

Where can we go to learn more about you?

Please visit my websites: Bennyaxt.com and Heroesofcare.com.  As mentioned, I’ve got a goal to meet 500 new people this year so feel free to get in touch via email too.

💎 Last Week’s Gems

📉 Everything is converging. Treasuries, stocks, cash and corporate bonds all yield about the same. Strange thing to see in a chart!

🤖 Build AI agents as a team or not? Cognition says don’t build multi-agents, whereas Anthropic says yes build multi-agents.

☕️ Starbucks is doubling down on human baristas after years of investing in automation, while certain tech CEOs have pushed for AI over humans.

✨From Our Community

• Join our Community Beta: Apply to join our upcoming invite-only community beta kicking off June 23, 2025 → Apply Now

• Get Past Replays: You can access our vault of community call recordings here

Dexter Zhuang
Say hi 👋 on LinkedIn or Threads
🚀 Partner with Portfolio Path

Hey {{ first_name | readers }},

We’re headed to SF and Detroit at the end of June - holler if you’re around!

Today, in 10 minutes or less, you’ll learn:

• 💸 Why growing revenue can counter-intuitively leave you feeling broke (and the 5-step system that fixes it)

• 🏦 How to implement a Profit First automation that avoids cashflow chaos

• ⚡️ The exact workflow that separates business profits from personal spending (with real percentages and timelines)

SPONSORED

☀️ 6-Week Summer of Growth Challenge: Starts Next Week

Apply Now (Limited Seats)

Tired of saying “I’ll start tomorrow”?

Join talented peers in our FREE 6-week “Summer of Growth” challenge, starting between June 16-23.

Here’s what we’ll do to help you accelerate your portfolio career growth:

• 🌐 Where: Inside our new Circle space. Also the home of our invite-only beta community (public launch this fall).

• 🎯 What you get: Bi-weekly live sessions, accountability check-ins, and a seat at the founding members' table to shape the community from day one.

• ⏰ Why now: Early joiners lock in founder perks and the best lifetime rate when the full membership opens.

Spots are limited.

Ready to stop overthinking and build momentum this summer?

APPLY NOW →

To get your brand in front of 7k+ professionals and entrepreneurs, fill this out and let's chat.

⚡️ How I automate business & personal finances (without the chaos)

Recently, my wife and I finished our May Money Review in just 15 minutes.

I used to be flying blind - like some entrepreneurs I know - when it comes to managing business and personal finances.

Mixing personal and business expenses, having no clear profit allocation system, and wondering why you’re always stressed about cashflow.

Until I made a few non-obvious but crucial changes.

In this newsletter, I'm breaking down exactly how I integrate and automate my business and personal finances - avoiding the chaos that plague a lot of fractionals, entrepreneurs, and small business owners.

☁️ Dream vs reality

Many people start a business with a dream of growing profits rapidly, paying yourself a FAT monthly salary - and having plenty left over EOY for rich bonuses for you and your staff.

However, the reality just hits different.

Especially when starting a service business. (Helloooo “feast or famine” cash cycles!)

A couple years ago, my business revenue was growing, but I felt broke.

Money would flow in, then disappear into sporadic spikes of a SaaS annual subscription renewal and self-employment tax payments.

I'd pay myself randomly. Sometimes $0 one month, $10k another month.

This made it tough for me to plan my family finances. How much can I contribute to our joint expenses? Joint sinking funds? Man I had no clue.

It felt like nothing was predictable.

Sounds familiar? Perhaps you’ve been there (or are there right now!)

That pain led me to spend dozens of hours researching and implementing the 5-step system I have today:

🏦 Step 1: Set up Profit First allocation

The first step was fixing my business accounts - er… account.

Because I basically only used one.

Today, I’ve implemented the Profit First playbook by setting up auto transfer rules in my Mercury Business accounts.

I suggest using any bank accounts that allow you to set up auto transfers:

Mercury screenshot (Not my account)

👉️ How I implemented this:

Every dollar that hits my Mercury Business income account gets automatically allocated:

• 30% Operating Expenses

• 50% Owner Pay

• 15% Taxes

• 5% Profit

On a daily basis, the revenue that hits my main accounts get distributed immediately to separate accounts using these percentages.

Even though this workflow sounds deceptively simple (how boring!), I can’t overstate how helpful it has been to calculating my expected spend on OpEx and Owner’s Pay.

Instead of wondering, “do I have enough cash?”, all the time…

Now I can just look at my bank sub-accounts and answer that question.

Pro-tip: Check out these Profit First guidelines on Profit, Owner’s Pay, Tax, and OpEx splits:

Next, let’s talk about paying yourself:

💼 Step 2: Establish consistent owner pay

I recently converted my US LLC to be taxed like an S-Corp.

Don’t worry if that means nothing to you - this isn’t going to be a US tax deep dive.

However, what matters for this article is that I can pay myself in two ways:

1. W-2/employee salary

2. Owner distribution

👉️ How I implemented this:

For (1), I set up Gusto to pay myself a monthly paycheck as consistently as possible.

Payroll compliance gets complicated, so I like using a tool like Gusto to handle things like tax withholdings automatically.

Note: Each state / country has its own payroll rules - e.g. pay frequencies, pay methods, etc. Definitely follow these to your best ability to avoid potential fines/penalties.

📊 Step 3: Optimize recurring expenses

When I started out, I kept getting hit with sudden spikes in SaaS subscription renewals, quarterly tax payments, and contractor payments.

👉️ How I implemented this:

Now I’ve smoothed out some things (not perfect, but getting there):

1. Converted majority of my SaaS to annual subscriptions that start in December - this helps me forecast how much cash I’ll need in my account by December

2. Pay my self-employment tax monthly automatically as part of my payroll instead of needing to remember quarterly estimated tax payments

3. Asked my team members / contractors to send me monthly invoices so I handle payouts in 1 batch per month

4. Auto-track my business expenses broken down by category using Kick.co

Of course, I still have miscellaneous spikes for things like attending conferences and business travel. However, my expenses - and therefore cashflow - are much more predictable than before.

🏠 Step 4: Design personal finance workflow

After getting married, it took several months to decide how we combined our finances, joint spending, and joint savings goals.

No, we’re not a “Combine ALL THE THINGS” kinda couple. (Although we do view our portfolio as “our portfolio.”)

We adopted a Yours, Mine, Ours approach:

• Joint checking for fixed costs (rent, utilities, groceries/food)

• Joint savings for goal #1 (honeymoon)

• Joint savings for goal #2 (family/childbirth)

• Joint investment for goal #3 (529 college fund)

• Joint investment for goal #4 (K-12 fund)

• Separate personal spending + investing accounts (retirement)

👉️ How we implemented this:

1. Open a Mercury Personal account ($240/year) - which has been great because it doesn’t require a SSN to add my non-US spouse as user on bank accounts.

2. Set up a savings or investment account per joint sinking fund

3. Add my individual checking account to payroll in Gusto

4. Set up transfer from personal checking to joint checking

5. Set up transfer from joint checking account to each joint sinking fund/investment account (and our personal checking to personal retirement)

6. Boom! We have our savings/investments allocated

🔄 Step 5: Automate what’s possible

Taking care of this stuff manually blows, so naturally I’ve tried to automate what I can:

• Profit allocation (Mercury auto-transfer)

• Owner salary (Gusto)

• Sinking fund transfers (Mercury auto-transfer)

• Investment contributions (Brokerage auto-contributions)

• All bills (autopay)

👉️ How I implemented this:

Want to see how this plays out? Here’s an example monthly schedule that’s inspired by my own workflow:

🙅‍♂️ What this system won’t do

This system feels like I got a real engine working behind the scenes now, but it’s definitely not perfect either:

• It won’t solve underlying business problems. If you don’t have profitability, the profit first system isn’t going to help.

• It won’t eliminate the “feast and famine” nature of service businesses. It will help you manage it, but the other part is stabilizing revenue.

• Finally, it won’t set itself up. You’ll need to do maybe 1-2 hours of upfront work, but once it’s running it’s pretty simple to maintain. (I just tweak Gusto and Mercury once a in awhile.)

✅ Next steps

My favorite part isn’t just the time savings. It’s the peace of mind.

I have a clearer picture of where the money comes from and goes - so I can just get back to doing what I do best in my work and life.

Here are the steps we covered:

1. Setup Profit First allocation

2. Establish consistent owner pay

3. Optimize recurring expenses

4. Design personal finance workflow

5. Automate what’s possible

So there you have it. Wishing your next money review takes under 15 minutes (or none at all!)

Thanks for reading. What's your biggest challenge with handling business or personal finances? Hit reply and let me know.

💎 Last Week’s Gems

👵 What % of retirees do you think spend down their principal in retirement? I’m shocked by this stat: “Across all wealth levels, 58 percent of retirees withdraw less than their investments earn, 26 percent withdraw up to the amount the portfolio earns, and 14 percent are drawing down principal.”’

🧑‍💻 NYTimes: Don’t Call It a Side Hustle. These Americans Are ‘Polyworking.’ Polyworking isn’t what I expected as the mainstream manifestation of portfolio careers, but I’ll take it. Step in the right direction I suppose 🤷‍♂️ 

🛢️ I just finished reading Kochland - an investigative book about Koch Industries, the 2nd largest private company in the US, family-owned, and one of the most secretive. The CEO and his brother were at one point wealthier than Bill Gates. Absolutely fascinating read.

✨From Our Community

• Summer of Growth Challenge: Kicks off between June 16-23 → Register Here

• Get Past Replays: You can access our vault of community call recordings here

Community Spotlight: Li Si Wong

Li Si is a senior product leader and founder of The Side Door, where she writes monthly insights on pattern recognition in business and life. She currently leads product at Altus, a scale-up in the project management space. She’s based in Melbourne.

How would you describe what you do to someone outside of your industry?
I decide what problems need solving and then collaborate with others to find effective solutions.

What triggered your interest in exploring the portfolio path?
I started wanting to be more intentional with how I spend my time - especially around who I meet with and what I say yes to. That shift in mindset opened up space for me to explore different paths outside of the traditional 9 to 5.

What’s your current portfolio career mix?

1. Product management for scale up

2. Real estate

3. Investment portfolio

What advice would you give to someone starting a portfolio career?
It’s okay to experiment. You don’t need to have it all figured out - just start, learn from what happens, and keep iterating. One quote that really shapes how I make decisions: “If it’s reversible, the biggest risk is moving too slow. If it’s irreversible, the biggest risk is moving too fast.” 

What’s a fun fact about you?
I have an unusual mixed-handedness trait! I write and play sports with my right hand, but instinctively use my left hand for everyday tasks like brushing my teeth, using my phone, and combing my hair. Apparently, this pattern of task-specific hand preference only occurs in about 1% of people and suggests unique brain wiring!

What's one piece of media that impressed you lately?
Tenacity is a Success Code by Dr. Julie Gurner

How can people connect with you?
LinkedIn

P.S. Did you enjoy this spotlight? Hit reply and let me know—or suggest another amazing portfolio pather we should feature next!

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Dexter Zhuang
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