You could say that it all began with $73k in student loan debt.

…For a degree in Geography that Chenell Basilio had no specific reason for obtaining. (This is the problem with requiring kids to pick a major at 18, then asking them to pay for it with exorbitant loans.)

Luckily, in Chenell’s case, her student loan debt became the driving force that pushed her to build a solo venture which would generate nearly half a million dollars in a single year. 

And if you’re impressed by that, you’ll be even more impressed by how she managed to burn the whole thing to the ground. 🔥 

🍻 THE DRUNK BUSINESS ADVICE

👉 Never mistake perfect market conditions for a perfect business model.

👉️ And for f*ck’s sake — ask for help when you need it.

And now — the story behind why this advice matters. 👇️ 

A degree. A shit-ton of debt. Now what?

As a kid, it was evident that Chenell Basilio had inherited the nosy resourceful gene from her mother.

No matter what sort of gossip was running through town, Chenell’s mom could always get to the bottom of it, digging up public records and old newspapers to uncover the truth. “She should have been a CSI,” Chenell jokes.

The rise of the internet during Chenell’s teenage and early adult years swept her into rabbit holes of research. She was baffled when classmates seemed so certain of what they wanted to do with their lives. Why were they thinking so far ahead? There was so much to discover in the present.

Chenell preferred to deal with the world as it came at her.

This mindset is pretty great for adaptability — but troublesome for planning ahead.

When Chenell graduated from college, she realized that she needed to find creative ways to tackle her Everest-sized mountain of student loan debt. So she did what came most naturally — she burrowed deep into the research rabbit hole.

Along the way, Chenell discovered Pat Flynn’s Income Reports blog series, where he detailed sources of income from various projects. 👇

An Income Report for Pat Flynn’s book. Source: Smart Passive Income

That gave her an idea. 💡

Chenell didn’t have multiple sources of income (yet) — but she did have multiple sources of debt. So she launched a blog series called Debt Reports. Every month, she wrote about how she was paying down her debt. 👇

A screenshot from Chenell’s early “Debt Reports” blog series.

The blog kept her accountable, which was important — but it also had the potential to earn income. So in an effort to grow her blog on a shoestring budget, Chenell began consuming all the free marketing content she could get her hands on. 

At the time, she was working at AAA (ya know, the roadside assistance company) — in the marketing department.

(When she graduated college, CSI mom sent out Chenell’s resume to hundreds of companies, until one day she got a call from AAA. Go mom.)

Chenell brought her fresh marketing ideas to AAA, and before she could say “holy shit I’m not qualified for this”, she was managing their monthly advertising budget —  in the millions. 🤯 

Right place. Right time. Right skills.

Chenell’s personal financial blog was beginning to gain traction, so in 2016, she attended FinCon — a huge conference for creators working in the personal finance niche. At the conference, she connected with many of the popular finance bloggers she had been following for years.

And when they discovered that she was managing millions of dollars of ad spend at her day job, they had only one question for her—

“OMG, will you please help me run ads for my blog?”

Um. Yeah.

So Chenell began taking on marketing clients. It started with a few finance bloggers… A few online course creators… Her step-dad’s flooring company (because why the hell not?) 🤷

And as word of her talent spread, so did her side-business. She was waking up at 3am to service clients, working on the train, and taking calls during her lunch break. By May of 2017, Chenell had saved up enough money to feel comfortable leaving AAA, and took the leap into full-time entrepreneurship. 👇️ 

In 2017, Chenell’s little marketing company (which was composed of only Chenell) brought in $42k in revenue. She was thrilled. That was almost as much as she made at AAA.

In 2018, she absolutely soared past that number, and raked in $117k, officially becoming a six-figure solopreneur. Then she closed out 2019 with $212k in revenue — still running the business completely on her own.

“Why did people think entrepreneurship was hard?”, she thought, rolling her eyes at the millions of failed businesses around the country. (Not so fast, superstar…)

In 2020, the world of digital entrepreneurship exploded. The pandemic brought about a combination of two things that ignited a fire under Chenell’s business:

• Those who lost their jobs wanted to re-skill themselves to be able to work virtually.

• Online course creators who taught those in-demand skills had insane growth opportunities.

And guess who specialized in marketing for online course creators?? 👇️ 

Careful, Chenell. Mo money, mo problems.

Chenell’s solo business brought in $452k in 2020. 🤯

If you’re wondering how Chenell managed to serve $452k worth of client business as a solo operator — so is she. 🤷

But she had help from some pretty remarkable market conditions.

For the non-marketers out there, here’s what the digital marketing landscape looked like during the pandemic:

Worried about the economic and supply-chain impacts of the pandemic, big companies dramatically cut their ad spend. This drove down the price of digital advertising, allowing smaller companies to see unprecedented returns on their ad spend.

Companies like Chenell’s clients — many of whom were online course creators, whose demand was simultaneously skyrocketing, as millions of people sought to re-skill themselves.

So let’s be clear. Chenell: 

1. Had far too many clients for any one person to handle.

2. And was too overwhelmed to optimally serve them.

But the extraordinarily novel conditions of the digital advertising market, paired with the unprecedented demand for the services her clients offered, still delivered stellar results.

…Until it didn’t.

Oh shit oh shit oh shit

As COVID chaos cooled, the digital advertising market began to correct itself, and it wasn’t so easy for Chenell’s clients to achieve solid returns on their advertising spend.

And since Chenell barely had enough time to wipe her own —ahem—, she couldn’t provide the attention that each client deserved to get back on track. She tried (and failed) to onboard freelancers to help with the workload, but it was too little too late, and she wasn’t prepared to properly manage them.

Clients began bolting for the door. 

A few at first…

Then many…

Then nearly all.

In 2021, her revenue plummeted from $452k to $136k. And by 2022, it had fallen even further to $65k.

It kinda looks like a giant middle finger. 🤷 

Chenell doesn’t recall much from that period — it was all a haze. She was too mortified to reach out to her peers for insights on the constantly-evolving digital marketing landscape. Her ego told her she should already know everything.

And looking back, she feels like this was her biggest mistake:

Chenell was watching her business burn to the ground, and she didn’t know how to fix it. So she just did nothing. And it died. ⚰️

That really sucked, but…

Chenell was too traumatized to rebuild her digital marketing business. But she couldn’t live in a hole forever — she needed to figure out her next move.

In the same way Chenell stumbled on Pat Flynn’s personal finance blog years before, she caught a story about how Mario Gabriele earned $300k in one year by writing his newsletter, The Generalist. This piqued her interest, but no matter how deep she dug, nobody had written about how he had actually pulled it off.

So she decided to reverse-engineer his newsletter growth.

Chenell spent 60 hours poring over every piece of data she could find, and compiled a deep-dive detailing how Mario Gabriele created his hugely profitable business from writing a newsletter.

She thought other people might be interested in this too…

So on December 4, 2022 — she published it.

Source: Growth in Reverse

And since she had just reverse-engineered how someone earned mad dough by simply writing a newsletter, she figured she could do the same for herself.

Growth in Reverse was born, and Chenell became determined not to make the same mistake twice. These days, she runs a very manageable business, which pays her bills and gives her the lifestyle she desires.

When asked “what does ‘wealth’ mean to you?”, Chenell responded:

And in an effort to keep others from repeating her mistakes, Chenell launched a podcast and a community for newsletter operators to help each other, learn from each other, and never feel like they’re alone.

Way to turn it around, Chenell. 😘 

Cheers! 🍻 

-Kristin

Nothing better instilled in me the virtues of delayed gratification than the Easter mornings of my childhood.

Mom, a devout Catholic, would rouse her sleeping children, dress us up in itchy church clothes, and scoot us out the door through a maze of pastel foil-covered eggs, dotting every surface of the house.

Our groggy eyes would grow wide and we’d salivate like a pack of ravenous golden retrievers, but we weren’t allowed to have anything until we got home from Easter Mass. I was Aladdin, tip-toeing through the Cave of Wonders, not permitted to touch any treasures until I retrieved the magic lamp for Jafar, else risk eternal damnation.

Except in the Catholic version, we had to go repent for our sins and do penance before we could come home and eat our weight in cheap chocolate.

I think Mom was trying to teach us to be good Catholics. (We weren’t church-on-Christmas-and-Easter-people. We were hardcore tour-with-the-band-pew-sitters.)

Well… I’m a shitty Catholic. But that doesn’t mean she failed. Here’s why:

1. I’m pretty good at the wine part. 10/10

2. Practicing delayed gratification as a kid made hard things a lot easier to handle as an adult. I don’t feel like I struggled as much as other people.

So thanks, Mom. 💗 

And I hope y’all have a restful, chocolate-and-wine filled Easter (regardless of whether you celebrate.)

Cheers! 🍷 

-Kristin

P.S. — Don’t worry, I’ll be back in your inbox next Sunday with a full-length edition of Drunk Business Advice.

Holy shit. This the 100th issue of Drunk Business Advice.

And the only reason I’m able to keep doing this is because you keep showing up and reading it.

I say this with zero snark or sarcasm: 

Thank you. ❤️ 

I’m truly honored that you have trusted me with a coveted spot in your inbox. Your messages of support and appreciation over these last couple of years have meant the world to me.

Source: Giphy

🍻 THE DRUNK BUSINESS ADVICE

👉 If you want to be great at something, get great teachers.

And now — the story behind why this advice matters. 👇️ 

What is a “writer”?

Call me on my bullshit if you disagree, but I believe the title of “writer” is earned once someone gets paid to do it.

Up until that point, you might “write” — but you’re not a “writer”.

For instance, I play the piano, but I would never call myself a “piano player”. A piano player is a highly trained, paid musician who other musicians and audiences rely on to deliver flawless performances. 

I play the piano to relax at the end of a long day, and I occasionally compose when I’m feeling creative, but mainly I just bang out drunken choruses of “Oh, What a Night” when friends come over and stay too late.

It’s their signal to leave. 👋

And adding the prefix “professional” is redundant. If you tell me you’re a…

• Mechanic  

• Web Developer 

• Marketer 

• CEO

…you don’t have to use the word “professional”. You would sound like a moron.

All of this is to say that I didn’t become a “writer” until March 7, 2023, when my first article was published in Trends — the (then) premium research arm of the popular business & tech news publication, The Hustle.

The first story I ever got paid to write.

Trends was a premium newsletter, which meant ~16k subscribers were paying $300 to read it. That’s some insane pressure for a newbie. But I strangely felt right at home, and in a matter of weeks, I went from writing a few stories, to stepping into the Managing Editor role.

This didn’t happen because I was a terrific writer, or an editorial savant —  it was because our audience was composed of entrepreneurs and aspiring entrepreneurs. And I knew how to talk to them.

This is how I learned my first major lesson about the media industry:

👉 People enjoy good writing — but they pay for insight.

Writing is team sport

Up until this point, I had never worked on an editorial team. I always imagined writers as moody lone-wolves, constantly at odds with their peers, their editors, and their publication.

Maybe that’s true in some cases, or maybe I just watch too many movies. And I’m still relatively new to this, so my perspective here is limited.

But let me say this—

The editorial team at Trends was the absolute #GOAT.

They’re the MVPs of my life. Source: Giphy

The only reason I’m now a “successful” writer is because of three wily wordsmiths who unapologetically shredded my early writing, while somehow simultaneously making me feel warmly valued:

• Shân Osborn (who now publishes Oh look another health trend)

• Ethan Brooks (who now publishes Austin Business Review)

• Brad Wolverton (Editor of The Chronicle of Higher Education)

It’s a hugely vulnerable experience to pour yourself into a piece of writing, then hand it to someone else to critique. But Shân, Ethan, and Brad took everything I wrote and made it 10x better with their coaching. They weren’t simply red-penning the shit out of my work — they were teaching me how to be an effective writer, and a potent editor.

They truly cared.

Soon, I was editing stories from powerhouse writers like Chenell Basilio and Chris Orzechowski (who are also, coincidentally, delightful f*cking humans).                              

This illustrates what exemplary teachers Shân, Ethan, and Brad truly are, and I’m boundlessly grateful to them.

Every story I edited made me a better writer. Every story someone else edited made me a better writer. There wasn’t a single interaction I wasn’t learning from.

I fell in love with this process, and quickly decided that I wanted my next entrepreneurial venture to be in the media space.

From ghosting to drinking

Thanks to some opportunities brought to me by Ethan Brooks and Brad Wolverton (again, the power of the team is paramount), I launched Polymath Media, a little CEO ghostwriting outfit.

It was absolutely the best thing I could have done at that stage. 

I was forced to operate on a super regimented publishing schedule, writing from the “desk” of powerful CEOs with huge audiences and spiky points of view. In a year, I published 150+ thought leadership stories totaling 115k+ words, which garnered over 4.7 million unique reads.

I had to treat writing like a real job. Because that’s exactly what it was.

Some people make it look easy, but it’s hard shit. Source: Tenor

This experience gave me undyingly consistent practice. I was writing almost every day. And when I wasn’t writing, I was reading interesting things to fill my brain with inspiration.

(Which is a magical way to live, tbh.)

I’m forever thankful for those opportunities. But after a while, I thought…

“I’m publishing incredible stories for other business leaders, and people are f*cking loving them. But I’m also a business leader. I’m not just a writer. I should be doing this for myself.”

So I birthed Drunk Business Advice. (The word “birthed” is intentionally chosen, because it’s probably the closest thing I’ll ever have to a child.)

And for eight months, I was publishing Drunk Business Advice alongside my CEO ghostwriting commitments. 🤯

So when I stepped away from ghostwriting, I felt like a bodybuilder who usually lifts 300 pounds being handed a 50-pound kettlebell. While 50 pounds is a lot of weight for most people, I had been lifting 300 pounds so damn consistently, and for so damn long, that 50 pounds felt light as a feather.

So today, as I hit “send” on my 100th issue of Drunk Business Advice, I must ask myself: What comes next?

…Death?

Jerry Seinfeld has a joke that goes like this:

Yep. I feel that. With death, there might be pain. There might be judgement (depending on your beliefs). 

With public speaking, there is definitely pain and judgment. It’s guaranteed.

But I’m one of those weirdos who kinda likes a little pain and judgement. It comes with the territory of publishing a newsletter like Drunk Business Advice. And frankly, it fuels me.

Public speaking is something I’ve dabbled in a lot over the years, but never formally pursued. So with 100 issues of DBA under my belt, now is as good a time as ever to get serious about it. Especially because I have some incredible mentors in this space, like the prolific Carmine Gallo. 

And as I learned with writing, having badass teachers makes all the difference. ♥️ 

So y’all are the first to hear —

Kristin Kenzy is now a speaker on the keynote circuit! Oh god.

And I have a new personal website to promote it. 

(This is different from my old personal website where I just hee-hawed about LinkedIn shitposting, and had an OnlyFans icon that Rick-Rolled anyone who dared to click it. I’m, like, a real grownup now.)

So if you or someone you know is putting on an event, and you want to add a little spice to the speaker lineup, let’s talk! (It’s not a shameless plug if I never had any shame to begin with.)

Until we meet again…

🍻 Cheers to the next 100 issues of Drunk Business Advice. 

🍻 Cheers to bringing it to life on stage. 

🍻 And cheers to you — for all the support, friendship, and laughs. Y’all are the best.

Love,

-Kristin

Every company worth its weight in coffee is shouting this from the rooftops:

“We prioritize employee wellness!”

I want to be clear right at the start — I don’t believe this is a bad thing. I’m not a monster. I want people to be well. I want people to be happy. And I want companies to care about the wellness and happiness of their employees.

But here’s the part I can’t compute:

At this very moment, companies are spending more on wellness than at any other point in history — but we’re not getting any happier. In fact, we’re getting unhappier.

🍻 THE DRUNK BUSINESS ADVICE

👉 You can’t fix your employees’ lives. And you shouldn’t try.

👉 Instead, fix the culture problems inside the business that you can actually control.

And now — the story behind why this advice matters. 👇️ 

“Wellness” is a hunk of hooey

Over the past 50 years, self-reported happiness in the U.S. has declined. Not a ton — just a tad. But over that same period, workplace wellness programs have grown from a negligible concept to a nearly $20 billion-dollar industry. 👇

What the hell?

Ok… so there’s an argument to be made that happiness is impossible to quantify, therefore this data is useless. That might be a fair point, but let’s assume for now that self-reported happiness = actual happiness.

And there’s also an argument that happiness is impacted by all kinds of stuff that isn’t work related. Sure. But given that 40% of our waking adult lives are spent at work, it’s safe to assume there’s at least a partial correlation between what people do at work all day, and their overall happiness.

So we’re left questioning… why?

Mental health seems to be the focal point around which every conversation about workplace wellness orbits. Not only are we spending more cash on wellness than ever before, we’re talking about wellness more than ever before. Gone are the stigmas of privately struggling with things like burnout, bullies, and boundaries. 

Now those topics have their own damn Slack channels. 

Based on all this openness, and all these resources to address these issues at work, we should all be happier than pigs in mud. But we’re not. Why?

Well… I have a few theories.

It starts with alignment

First, workplace wellness programs simply don’t address the biggest elephant in the conference room:

Misalignment.

Decades of research consistently shows that happiness is driven by things like social connection, autonomy, meaning, and security — not by access to wellness services.

And as we’ve already established, we’re spending a shit-ton on wellness services.

This all suggests that if we have a happiness problem, that problem isn’t caused by a lack of wellness interventions, but a misalignment between the values that make people feel good, and what they actually experience at work.

My pal Simone Stolzoff (author of one of my favorite business books ever, with a new one coming out in May) said it beautifully:

Simone knows his shit. Source: LinkedIn

“Working on the wrong thing,” as Simone puts it, is not a problem that a free meditation app or corporate retreat could ever attempt to solve.

And honestly? Companies shouldn’t make themselves responsible for solving it. In most cases, the pursuit of happiness should fall squarely on the shoulders of the employee (ya know, an autonomous human adult with full agency). It’s up to them to recognize their misalignment, and make a change. To ask for what they need. Or to move on.

Companies should inspire workers to take charge of their own happiness instead of playing a relentless and expensive guessing game. Because no one else knows what alignment feels like for an individual — except that individual.

But we currently exist in a culture where employers are sticking money-colored bandaids on their miserable employees' heads, and claiming wellness victory. 

And the only winner is the company who makes the money-colored bandaids.

Optionality is the thief of joy

A few years ago, I was mentoring a 23-year-old through some career dissatisfaction. She had only been in New York for 18 months, and had already cycled through three finance jobs.

To top it all off — she was young and beautiful and dating. On Tinder. 

Our conversations would begin with her work woes, but somehow always migrated to her dating life. And I couldn’t help but notice a constant parallel between the two:

The possibility of shiny new options amplified the (often small) dissatisfactions she had with what was right in front of her. It was the “grass is always greener” paradox.

She would get home from a date and immediately begin thumbing through the infinite handsome hunks on Tinder, and spend her weekends browsing LinkedIn for other jobs.

Thank you, next. Source: Giphy

Was this an inherently bad thing?

At 23… probably not. Carouseling through jobs and boyfriends at that age seems like a perfectly normal, if not healthy, phase of self-discovery. 

But there was a problem: she was goddamn miserable.

She wasn’t telling a chauvinistic boss to shove it, and waltzing out of the office, proud to discover her own voice. She wasn’t assessing the qualities in her romantic partners that made her feel valued vs disposable, and using those assessments to guide her future dating decisions.

Instead, she was consuming an entire pharmacy’s worth of antidepressants and playing the “what if” game on repeat — ever envious of the version of herself that she could visualize as these “options” fluttered across her iPhone screen, just out of reach.

Now — I’m not saying that people should settle for a work situation that makes them unhappy. But I do question whether that unhappiness stems from their work situation, or from being constantly blasted with other, seemingly more appealing, options.

This is the part that’s gonna get me in trouble…

I have one more (tad controversial) personal theory about why happiness is declining, while attention and spending on mental health and wellness is going up.

Please don’t cancel me.

Oh god.

Here goes.

As workplaces become more open to accommodating the needs of unhappy or mentally unwell employees, trying to solve those highly personal problems with wellness initiatives, happy employees have to put up with a lot more shit.

Everyone is, of course, entitled to some bad days. Or even some bad seasons. It’s important for teams to establish trust and support one another during those times.

But now, the disengaged… the lazy… the narcissistic… the people who truly don’t fit in… are simply assigned an archetype by whatever personality test their company adheres to, and everyone is given training on how to best interact with that archetype.

The happy, productive, aligned people are forced to make accommodations for the unhappy people.

All in the name of “bringing your whole self to work”.

Because that’s what happens when workplaces try to solve people’s personal problems. The line is blurred, or disappears entirely, and all of a sudden “the full moon drained all my energy” is just as valid a reason to slack off at work as “my mother died”.

This sounds harsh, but I’m not (completely) talking out of my ass here. I’ve experienced this problem first hand. I was once a happy, aligned, and mentally well employee who simply wanted to do my job. 

But you know what drained all my energy? Making accommodations for colleagues who thought their happiness was the company’s responsibility (therefore my responsibility). Because the company had made it our responsibility.

A workplace culture that so proudly prioritized wellness turned me from a happy employee into a sad one. And while this was just my personal experience, I suspect I’m not the only one.

It’s not that bad I swear

Should companies ignore employee wellness? Absolutely not.

It’s just that the stuff they’re doing now seems pretty darn useless. These programs are all signal, with no substance. And the signal they’re throwing is “bring us all your personal problems and we’ll fix them,” which is a dangerous idea.

So what does an effective employee wellness program actually look like?

In my unqualified opinion, it should incorporate two key elements:

1. Normalizing frank conversations

Businesses have seasons. Life has seasons. They’re not going to ebb and flow in tandem, and collisions are to be expected. Alignment isn’t possible 100% of the time. 

So employers and employees need to be honest with each other about their needs, and those conversations should be rooted in tangible outcomes and timeframes. Listening is imperative — on both sides.

2. Prioritizing trust above all else

The shit that’s inducing ulcers, causing sleepless nights, and throwing employees into fits of anxiety, isn’t lack of lunchtime yoga classes. It’s “my boss is out to get me” or “my colleague dropped the ball”.

Wellness programs assume that if an employee could just breathe better, sleep better, or think more positively, the stress would melt away. But the best extinguisher of stress is to be surrounded by people you trust. 

Hell, being part of a trustworthy cohort can even make stressful situations fun — because conquering high-stakes conditions bonds people together, creates deep relationships, and seeds loyalty.

—

Despite the negative tone of today’s issue, I’m still an optimist. Do I think misguided wellness programs are silly and wasteful? Yes.

But I also view their existence as a positive sign that employers actually give a shit.

And if I rubbed you the wrong way today, I’ll try to rub you the right way next time. Just don’t report me to HR. 😉

Cheers! 🍻 

-Kristin

I was shitting myself.

Every spare moment was spent devouring every book on real estate development and finance that I could get my hands on, scrutinizing dozens of academic case studies, making flashcards for terms I was unfamiliar with, and building budgets for fun.

Why?

Because I was about to show up for my first day on campus — at Harvard.

And my imposter syndrome was bigger than a Kardashian caboose. 

Me — glancing back at my imposter syndrome. Source: Tenor

🍻 THE DRUNK BUSINESS ADVICE

👉️ As a species, we learn a little bit from books. We learn a little bit from teachers. We learn a little bit from practice.

👉️ But we learn the most by surrounding ourselves with wickedly smart, agile, and curious people who truly care about us. 

And now — the story behind why this advice matters. 👇️ 

I didn’t go to college

I wanted to. I tried to. I was smart enough. (I think.)

But it just never really worked out for me — partly because of circumstances like money and options, but mostly because I was a stubborn, impatient little asshole who walked out of the womb determined to be self-reliant.

And while college certainly isn’t the antithesis of self-reliance, it does delay it.

It’s hard to make enough money to be self-reliant when you’re busy writing term papers and showing up for class. So instead committing to the collegiate path, I decided to fudge my resume to get jobs I wasn’t qualified for, thinking:

“Why would I pay to learn stuff when I can get paid to learn stuff?”

As immature, short-sighted, and dishonest as that was, it worked out for me — and my employers. Because once I got the jobs I was unqualified for, I was incentivized (by money) to work harder than everyone else.

And as soon as I had some experience under my belt, I started my first business at the obnoxiously know-it-all age of 21.

The rest is history. I had a great career. Folks were shocked when I told them I didn’t have a degree. And I always told myself that if not having a degree ever prohibited me from taking the next step in my career, I would go back to school.

That never happened.

But about 15 years into adulthood, I began to feel stagnant — not in my career per se, but with my personal growth and world outlook. I didn’t need an education — I wanted one. But I had a pretty big barrier… the kind of education I wanted was an advanced degree… but I barely had a high-school diploma.

I had heard that there were some Executive MBA programs that didn’t require tertiary prerequisites, but after researching them, I found that most of them were, well, crap.

On a whim, I decided switch up my search criteria to include the term “real estate” (the industry I worked in), and came across a school I had never dreamed to consider—

Harvard.

Harvard Business School doesn’t offer an Executive MBA, but Harvard Graduate School of Design offers a comparable Executive Real Estate program. And it looked absolutely perfect.

To even apply, they required 15 years of experience, and two letters of recommendation from recognizable leadership figures (one of which I obtained from the legendary Frank Supovitz 🙏 ).

But they didn’t require a bachelor’s degree.

So I applied — thinking I didn’t have a shot in hell. It was Harvard, for christ’s sake.

Then...

The humor is not lost on me that I got accepted into Harvard on 420. 🤦 

I was instantly overcome with a confusing cocktail of:

• Euphoria: After years of being embarrassed by answering the question “Where did you go to school?” with “I didn’t”, if I worked hard and passed this program, I would officially be a Harvard Alumna.

• Disbelief: Was this some kind of mistake? Were they going to revoke my acceptance as soon as I told people I was going to Harvard? How humiliating.

• Panic: How the hell was I going to pay the $80k+ price tag? What if I’m truly not qualified? What if I fail?

This was going to be an intense and life-consuming endeavor. And expensive as hell.

So I had to honestly ask myself — was it worth it?

I began crafting a cost-benefit analysis to answer that question… And my husband threw it in the garbage.

“You’re going,” he announced. Then he walked out of the room. Mic drop. He cut through my bullshit, and pointed out what should have been obvious — this was an unmissable opportunity.

So I wrote Harvard a big fat check, and started preparing for what was sure to be the most transformative year of my life.

Back to shitting myself…

When the faculty sent over the required reading for the first two weeks of class, I printed it all out, and filled two 3-inch binders with case studies alone. That was on top of all the books and articles that were strongly encouraged.

I immediately cancelled a vacation I had planned to France before first term, and spent an entire month ignoring everything else in my life so I could study until I went cross-eyed. If I was nervous before, now I was one twitch away from tears every damn day.

And finally, it was time.

Anxiety was humming under my skin when I finally arrived at Harvard’s iconic campus, and stepped into Wasserstein Hall for my class’s welcome reception.

“Hey, it’s the ice skater,” bellowed a California accent from across the room.

An energetic man with a toothy smile darted over to introduce himself. He was one of my new classmates, and led the real estate division of the company that owned the Anaheim Ducks NHL team.

His name was Ian, he had read my bio and wanted to talk hockey, and to my great relief, he was the least intimidating person imaginable.

I unclenched a little bit.

Then I started encountering more classmates — all friendly, curious, and just as jittery as I was. Somehow, being in a group of people who are all nervous made everyone less nervous.

Once we all checked-in, the faculty ushered us into an event space, gave us alcohol, and split us into study groups with whom we were instructed to prepare for each day’s case studies.

Then, like a scene from The Amazing Race, they shot a metaphoric starting pistol, and told us all to grab our group mates and get to work. Have plans for tonight? Not anymore. You’re gonna spend tonight prepping the f*ck out of tomorrow’s case studies with a group of strangers.

Holy moly. This was real.

We all rushed out of Wasserstein Hall, and three different study groups ended up at the same restaurant near campus. After a short discussion about the following day’s case studies, the conversation shifted to a far more interesting topic — each other. We ordered another round, and got to know one another.

…Oh, why don’t we share a bottle of wine and chat some more?...

…Where did these cocktails come from? Gosh, y’all are funnn…

…Tequila shots? Well, if you insist… 😵‍💫

I stumbled home, and suffered the terrifying realization that I was unquestionably drunk. And tomorrow, beginning at 9am sharp, was our first day of class. 🤦

So, I endured my first official day at Harvard with one of the worst hangovers of my life. 

(Hey, at least I made it to class.)

Despite months of preparation, my mind felt cloudy, and I was cursing myself for my inability to jump into the conversation with creative insights that were on the tip of my tongue.

But that evening, when one of my classmates suggested we all go out again, I rallied. This became our normal routine. I grew accustomed to being hyped-up at night, and hazy in class.

This an official marketing photo for Harvard. If only they knew…

Sooo… Why did I do it?

Back then, I couldn’t identify the logic that pushed me to prioritize socializing over academics. It seemed ludicrous that I didn’t posses enough self-control to choose an early night hitting the books above drinking into the wee hours with friends when I knew I had intense classes the next day.

But I now realize that every minute that I spent with these people absolutely electrified me. They came from all over the world. They had unique perspectives, fascinating stories, and most importantly, they made me feel wanted and valued.

So in hindsight, it’s unmistakable — I had found my tribe. The sense of belonging this group offered me far surpassed all the other advantages Harvard delivered.

As a species, we learn a little bit from books. We learn a little bit from teachers. We learn a little bit from practice.

But we learn the most by surrounding ourselves with wickedly smart, agile, and curious people who truly care about us. 

Lifelong besties!!

This is what I missed out on by skipping college when I was young. I was only focused on outcomes, and not on relationships. I thought I could have success, or I could have friends — but not both.

What a shitty way to think.

After graduation (yes… I somehow made it to graduation), I became hooked on keeping the tribe alive. I visited my classmates all over the world, and joined the Leadership Board of our Alumni Association to spearhead new programs to keep everyone engaged and connected, long after we left Harvard Yard.

And in 2024, I received another unexpected email from Harvard asking if I —a loser without a degree who was hungover for all my classes— would consider joining the program on the instructor side.

I “gesture robustly”, as one colleague pointed out. I guess it’s better than gesturing flaccidly. 😆 

I’m now in my second year as an advisor, and just returned home from a galvanizing term on campus, getting acquainted with this year’s killer students in the classroom — and in the bar. 🍸️ 

As usual, it’s going to take me weeks to come down off this high.

And for my liver to recover.

Cheers! 🍻 

-Kristin

When I decided to write an issue of Drunk Business Advice about balancing business with parenting, I reached out to some dear friends who I admire as both entrepreneurs and parents.

Here are some exact quotes from those conversations:

Soooo… I think I struck a nerve there. 😳

Also, this is a prime example of why non-parents probably shouldn’t attempt to give parenting advice. I didn’t even know the right questions to ask.

🍻 THE DRUNK BUSINESS ADVICE

👉 Something’s gotta give. So when you’re forced into a tough decision, make it, move on, and don’t second-guess yourself.

👉 Go listen to this podcast. No questions. Just do it.

And now — the story behind why this advice matters. 👇️ 

I’m the kid of entrepreneurs

In my house, there was never any separation between work-life and home-life — it was all a mushy mess of moneymaking mayhem.

My family’s earliest business was a production company that installed entertainment on cruise ships:

I found this old promo sheet last time I visited my parents. Pretty cool, huh?

Mom and dad wrote the shows together. Then mom would handle the creative stuff, like casting and directing, and dad would handle the business stuff, like production and contracts.

My parents converted our garage into a rehearsal studio, complete with wooden dance floors, mirrored walls, and audio equipment to get performers ready for the stages on the high seas.

Walking around the house, you would stumble on singers, dancers, and musicians in every square foot, and the company’s musical director actually lived with us (his bedroom was right next to mine).

And my favorite part? Our closets were treasure chests bursting with sparkly costumes.

I love how it looks like I’m holding a cigarette like a real Vegas Showgirl. Pretty sure it’s a pretzel stick.

Why did my folks do it this way? Why didn’t they lease a production office and rehearsal studios? Why did they bring all this chaos into a home with two small children?

Because in a family business, every penny spent on the business is a penny not spent on the family. They wanted to maximize their margins. And the best way to do this was to run the entire business out of our house — decades before the internet made at-home businesses a normal, boring occurrence.

Of course, we spent a fair amount of time on the cruise ships as well, but the business operations were handled from our house.

And my little brother and I were there for all of it.

I have vivid memories of sitting at the casting table during auditions, perusing headshots and commenting on who I thought was talented and who sucked — usually loud enough for the poor auditioners to hear (soooo sorry about that).

And I recall another time when the xerox machine smudged some lyrics on a copy of sheet music, forcing a new cast member to guess a line during a South Pacific musical tribute rehearsal. I walked over, gave him the correct line, and walked away baffled that these people didn’t know every word to every Rodgers & Hammerstein song ever written. I mean… who doesn’t? 😉

I recently asked my parents how they approached the decision to weave their young kids into their business so tightly. Their answer wasn’t surprising:

“We didn’t really think about it.”

There was no intention there — just survival. They needed to make money, and this was the best way they knew how to do that. And they had kids, so of course we were around for it all.

I think we turned out alright. 🤷

I’m not a parent, but…

While I share entrepreneurship with my parents, I don’t actually share parenthood. So I interviewed 10 friends who are badass business owners and parents.

And as I mentioned earlier, I originally approached these conversations wanting to understand how they balance everything, so I could share those amazing secrets with all of you. But what emerged wasn’t balance — it was a shit-ton of collisions:

The moments that mattered most to their business, and the moments that mattered most to their family, had a strange habit of arriving at the same damn time.

So something’s gotta give.

And no one has the luxury of planning these decisions. They’re made in the moment. Some days the business will “win” in the moment, other days the family will “win”. 

But the best thing you can do when a collision occurs is just make the decision and move forward without endlessly second-guessing it. Because trying to hold both roles in perfect equilibrium is utterly unrealistic.

Most of the friends I spoke with have rockstar spouses who anchor the family during times when their business is blowing up. But when my friend Michael Jacobs went through a divorce, he suddenly became a single dad — and he still had to run his manufacturing company.

Yikes.

He surrounded himself with other parents for support, but realized they weren’t addressing the shit that really mattered:

Now that his kids are older (and he’s happily re-married), Michael has taken a step back to reflect on that nutty time. He decided to do what any motivated entrepreneur would do when examining a big question:

Start a podcast. 🎙️

Duh.

Here’s Michael interviewing Tony Berardo on why presence is more important than prestige.

Michael’s guests on Gap to Gig Podcast have included mental health professionals, entrepreneurs, and career coaches — but also some truly legendary high-achievers, like an Olympic high-jumper and a former fighter jet pilot.

And while he mainly focuses on fatherhood, moms and even non-parents (like me) have been listening in droves. Because this shit is universal.

We’re all seeking balance, but life is really about just managing collisions. That’s the essence of Drunk Business Advice.

So let this serve as your reminder to stop trying to be everything to everyone, and start enjoying the buzz. 🍺

Cheers!

-Kristin

P.S. — HUGE thanks to my incredible friends who took time to share their parenting woes with me. Y’all are legends:

• _{Tyler Cook, Owner of Hypermedia Marketing}

• _{Angela Smith, Owner of Work Nouveau}

• _{Rob Capili, Entrepreneur and Filmmaker} 

• _{Jacob Stone, Owner of WorqTap}

• _{Jacqui Myslinski, Owner of Productivity Nerd}

• _{Logan Zimmerman, Healthcare Entrepreneur}

• _{Jason De Los Santos, Owner of Pixelated Stories}

• _{Jesus Vargas, Owner of Low/Code Agency}

• _{Sarah Mcloughlin, Marketing Entrepreneur}

And of course… Michael Jacobs. Go listen to Gap to Gig. It’s f*cking rad.

Every time the teacher said “I’m going to put you in groups for this next assignment,” I’d stare at her like this:

Let me arrange my blocks in peace, you wretched woman.

It’s not that I’m anti-social. It’s not that I don’t play well with others.

It’s just that when something is important — I simply prefer to do it myself.

🍻 THE DRUNK BUSINESS ADVICE

👉 “Solo” doesn’t have to mean “alone” — but it does mean “in control”.

👉 If you’re a solopreneur, or thinking of becoming one, go read this report right now.

And now — the story behind why this advice matters. 👇️ 

🎶 Allllllll byyyy myyyy seeeeeeeeeeelf…

I can’t f*cking spell.

For someone who writes about business and entrepreneurship, you’d think I’d be able to spell “entrepreneurship” in my sleep.

Nope. I always mix up the “u” and the “e” in the second half of the word. Luckily, modern technology saves me:

But here’s the problem with spell check — it only works on words it recognizes. And this issue of Drunk Business Advice isn’t about entrepreneurship.  

It’s about solopreneurship. 👇

Even though Merriam-Webster officially added “solopreneurship” to the dictionary in 2020, most spell checks still don’t recognize the word. I didn’t have “being professionally and emotionally invalidated by spell check” on my 2026 bingo card, but here we are. 

Ladies and gentlemen, if you haven’t guessed yet — I am a proud solopreneur.

Why have I chosen the solopreneurship path at this stage in my career? Two big reasons:

1. I never again want to be an employee

2. I never again want to have employees

(Ok… “never” is a strong word, and life is long, but I’m pretty darn committed to this right now.)

I’m now on my third solo business, and I’m beginning to recognize the pattern that keeps attracting me back to this lifestyle:

👉 If I’m not in control, I’m miserable.

And no amount of money or stability can ease the stomach ache I feel when things go poorly due to factors I could have influenced — if only I had control. When I screw something up myself, I can live with those mistakes, because I learn from them. They help me grow and improve.

But to watch a project fumble… knowing I could have saved it if only my hands weren’t tied behind my back… that’s just pain for the sake of pain.

A shrink would probably tell me that I need to work on my control issues. That I need to learn how to trust people. That all this hoo-ha is negatively impacting my relationships. 

After all, no one ever says “control freak” like it’s a good thing. Folks don’t aspire to be control freaks. Parents don’t raise their kids to be control freaks. And no one wants to marry a control freak.

But here’s the thing—

A lifetime of evidence suggests that I’m happier in my relationships, and happier in my work life, when I’m flying my business solo. And since solopreneurship is a valid career choice, why not lean into my strengths?

You don’t have to be alone

The origins of the word “solopreneur” date back to the early 90s, and although there’s no official coiner credit, many look to Terri Lonier as the flame which ignited the solopreneur movement.

In 1993, she published the book Working Solo, which was the first ever practical guide to solopreneurship.

And earlier this week, I hopped on a call with her. 👇

The myth, the legend: Terri Lonier

But here’s the nutty part: I didn’t have the slightest inkling of her background prior to this call. 

I wasn’t doing research on solopreneurship for Drunk Business Advice (even though I’ve been planning this article for weeks). I wasn’t looking to rub shoulders with the badass who blazed the path for folks like me to run solo businesses.

We just wanted to talk about books.

Terri and I are both working on historical fiction novels set against the backdrop of the industrial revolution — so we decided to get together to nerd-out on history and fiction writing.

Business talk was not on the agenda.

But as we were easing into the conversation, I asked Terri how she got into writing, and she humbly told me about her first book… ya know… the one that shaped the entire solopreneur industry.

I had no clue I was speaking with a damn LEGEND. And this leads me to the most important lesson of solopreneurship:

You don’t have to be alone.

Solopreneurs might be “control freaks”, but we’re also humans who thrive on the creative juice that can only be squeezed by other humans.

We join communities and masterminds (which is precisely how I met Terri). We go to events. We learn about each other’s stories and outside interests. We’re less protective of our social bandwidth because we’re not bogged down by the barrage of conversation that comes with managing a team.

And I would argue this enables us to have stronger, more diverse, and more supportive professional relationships. We might be solo, but we’re far from alone.

So if you’re currently running a solo business, hit reply to this email and tell me about it. Let’s be solo — together. ♥️

Many uncomfortable considerations

If you’ve read up to this point, you might be thinking “Omg this sounds like me, I’m going to quit my job (or dump my team) and go solo!” —  But hold up a minute.

This. Shit. Is. Not. Easy.

For instance, in 2025, my business’s revenue plummeted nearly 80% compared to 2024. There are two big reasons for this:

1. I underwent a major surgery from which I’m still recovering.

2. And I pivoted away from cash-cow clients, and into productized services, which takes time to ramp up.

Getting work done is a tad difficult from a hospital bed.

When YOU are your business, it’s a high-risk game. 

Get sick? No one is going to cover for you. So it's imperative to build a model that accounts for this possibility, unless you’re genuinely cool with that risk, which most of us aren’t.

While there’s a stupid amount of money in client work, the health issues I had last year were a wake-up call in this regard — so I embarked on a gambit to mitigate that risk in the future. Which means my income is peanuts right now.

And this is just one of many uncomfortable considerations:

• Can you tolerate income volatility without spiraling? 

• Are you disciplined enough to get shit done without any accountability? 

• Can you handle long stretches of relentless work without any validation? 

• Do you actually want autonomy — or do you just hate your current boss?

Solopreneurship is not for everyone, and if you’re listening to advice from some bro on LinkedIn boasting about how he built a 7-figure solo business in three months, you’re already starting on the back foot.

One of the best breakdowns I’ve ever seen on this topic comes from my friend Adriana Tica, (who also writes a killer newsletter called Strategic AF).

She put together the State of Solopreneurship, a zero-bias report about how soloprenuers actually make their money. She interviewed over 150 of ‘em. Then she analyzed the shit out of what she learned, and crafted a practical guide to what it takes to be a successful solopreneur in 2026.

And since she’s a doll, she’s agreed to share it with Drunk Business Advice readers for free. You can grab it here.

Y’all — let’s all commit to making solopreneurship a little less lonely. I invite you to reply to this email with whatever is on your mind. It will give me the energy I need to make it through another week, and hopefully you’ll feel the same! ♥️

Cheers! 🍻

-Kristin

P.S. — Terri is (bravely) writing her novel in public! Go check out her Substack. Our conversation inspired me to carve out more time to work on mine, which has already been in progress for 8 years. Hopefully I’ll have something exciting to share with you on that front soon!

“Most people approach business relationships transactionally. You don’t. You help people without expecting anything in return. Why is that?”

Earlier this week, I was recording a podcast, and got hit with that question.

My first reaction was to feel wildly flattered by the host’s kind veneration of my character. He was basically saying that he believes I’m a genuinely nice person. How lovely. 🥰

But my second reaction was a painful acknowledgement that this “genuinely nice person” thing is an embarrassingly recent development in my life.

Because for most of my career, I was kind of an asshole.

🍻 THE DRUNK BUSINESS ADVICE

👉 Embrace your limits, and use them to guide you.

👉 The values that are most important to you in one season of your life might be hurting you in another season of your life. Regularly ask yourself what wealth really means to you.

And now — the story behind why this advice matters. 👇️ 

There was nothing I loved more than proving people wrong

Whether it was from my teachers, my bosses, my bullies, or even my parents, I never tolerated being told “no”. I’m an obsessively goal-oriented person — with a freight-sized chip on my shoulder.

At the onset of any challenge, my brain has never been like “Ehh, that goal seems a tad lofty, maybe I should slow down…” Instead it screams “LET’S F*CKING DO THIS AND PROVE THOSE B*TCHES WRONG!”

It’s no surprise my noodle works this way. As you learned last week, my first career was in competitive figure skating — which is basically gymnastics on butcher knives, and requires the confidence of a king.

Ahhh… young Kristin. So healthy. So vibrant. Such a jerk.

I spent my days flinging myself high into the air, rapidly rotating my body at 300+ RPMs, all while attempting to land gracefully on a 3mm blade.

On ice. 

Again. And again. And again. And again.

Sometimes I would land. Sometimes I would crash with the same downforce as a grand piano, splintering onto a frozen sidewalk.

I was just a kid, and had no intellectual understanding of the complicated physics that determined my ability to execute (or fail to execute) seemingly impossible skating maneuvers. I simply had to ignore my limits and remain steadfastly focused on my goals — even when my ass was bruised so badly that doctors would threaten to call CPS.

But while this kind of brutal determination to push through my physical and mental limits seems like a required character trait for a competitive figure skater, I’d argue that it carried a pretty undesirable side-effect:

It turned me into an insufferable jerk for most of my life. 🤦

Hear me out — I’m not saying that big goals are an inherently bad thing. I love having goals. I even teach classes about goal-setting, and how to set up systems to help people achieve their goals.

But the dark side of all that is a transactional approach to damn near everything — especially relationships.

You start viewing all the people in your life through a (pretty nasty) binary lens. They’re either:

1. Someone who can help you reach your goal, or

2. Someone who stands in the way of you reaching your goal

This is a depressing way to go through life. So let me propose an alternative:

Instead of setting goals, start leaning into your limits, and using them to guide you.

When we organize our life around achieving our goals, we view our limits as constraints we must break through — else we’ll fail — miserably and embarrassingly.

But what if constraints are a good thing? What if they’re the best compass we have to guide our path forward?

Real talk…

The last few years have dramatically knocked me on my butt.

Back in May, two of the most esteemed orthopedic surgeons in the world (not exaggerating) sliced my body in half (again, not exaggerating.)

They literally chiseled my hip socket off. It was like… completely detached from the rest of my body. Loosey goosey. Flubbly bubbly. Swimmy whimmy. My entire left leg was just sort of… out there.

Then they screwed me back together in a new position. 👇

Yes. This is a picture of the inside of my body.

I was bedridden for months. I had to be pushed around in a wheelchair whenever I left the house. And the whole ordeal was brutally painful.

Then, when things were supposed to begin looking up, I received news that I had developed not one, but TWO stress fractures (an uncommon complication from this procedure) — which would delay my recovery, and possibly require extra surgeries.

God dammit. 

But the pain and physical restrictions from the hip condition this surgery is designed to cure had been torturing me for two years before they ever even sliced me open. Pretty much every form of exercise was a no-go. Just walking around the city was torture. I couldn’t even roll over in bed without excruciating pain.

And I gained 40 agonizing pounds. 😭

I’ve been an athlete my entire life, so my physical deterioration not only impacted my mental health — it screwed with my entire sense of identity. And to top it off, I’m in the midst of building a new business, which means my income is hit-and-miss.

So let’s recap. I’m currently:

• Overweight

• In debilitating pain

• Mentally precarious

• And financially unstable

But strangely, I’m also the happiest I’ve ever been. How is this possible?

Because all this crap has forced me to no longer view my limits as constraints which keep me from reaching my goals and attaining happiness.

Instead, my limits are like bowling bumpers, keeping me out of the gutter as I move toward the pins at whatever pace I damn well please. And since my goals no longer involve crashing through limits, taking out anyone who gets in my way, my heart is open to helping others — which, it turns out, brings me far more pleasure than crushing goals ever has.

I’ve redefined what “wealth” means to me. 

It used to mean money and prestige. (And I do believe that definition served me well for the emergent season of my life.)

But now, “wealth” means flexibility, the freedom to explore creative pursuits, and most importantly, the ability to prioritize my relationships.

Being fat, poor, and immobile — constraints that challenged my ruthless goal-oriented mindset — ended up being precisely what I needed to find happiness in this new season of my life.

Who doesn’t love Alysa?

Unless you’ve been hiding out in a hut with no TV, internet, or smoke signals for 100 miles, you’ve probably paid witness to the inspiring story of America’s newest Olympic figure skating gold medalist — Alysa Liu.

I love a happy gal who drops an f-bomb on live TV. Source: Reddit

(I know I’ve been writing a lot about figure skating these last few weeks, but this is the brief moment that rolls around every four years where people actually give a hoot about my sport — and I’m gonna milk it thankyouverymuch.)

Now… I’ve seen a lot of “What Alysa Liu’s comeback taught me about B2B sales,” posts on LinkedIn these last few days (🤮), but there truly is a shit-ton of value to be gleaned from her story. 

Here’s how I see it—

Her entire identity was built on crashing through limits and crushing goals. Just like mine was. I have a stomach ache thinking about it. That’s a brutally hard life — a life where the line between soaring success and dismal failure is razor-thin.

Alysa’s surface-level story is": “Child prodigy burned out from the pressure, then discovered the joy of her sport, and returned to win Olympic gold”.

But I believe the reason she found joy in skating is because she redefined what “winning” meant to her.

I’m not in her head, so I can only speculate on what her goals actually are, but it’s pretty damn clear that she didn’t re-enter the sport to dominate the podium. She has said herself that she started skating again to make art and be with her friends. 

And that mindset shift just happened to also earn her the first Olympic gold medal for the U.S. in ladies figure skating… in her entire lifetime.

Her limits guided her to a much happier, and more successful, season in her life. And I f*cking love her for it.

Cheers! 🍻

-Kristin

“I blew it.”

That was the heartbreakingly honest response Ilia Malinin, our Team USA “Quad God” figure skater gave in an interview, mere moments after the gold medal favorite finished his disastrous free skate program on Friday.

But the first thing he did after “blowing it” was hug his rival — the man who was taking home the medal Ilia traveled to Milan to capture — and say:

My cheeks are still soaked with tears. Source: Reddit

My first career wasn’t in business — it was in competitive figure skating.

And I don’t think I’ve ever been prouder of the sport that kick-started my life.

🍻 THE DRUNK BUSINESS ADVICE

👉 No one else in the world understands your life as much as your greatest opponents. 

👉 Smart competitors know those relationships are a gift.

And now — the story behind why this advice matters. 👇️ 

Just some filthy rink rats from Florida

I was the one with the glow-in-the-dark jump rope. That made me a god.

All summer long, while the rest of Florida sweltered, my friends and I retreated to a 50-degree metal box for 10 weeks of training camp. Our sanctum contained a 20,000 square-foot sheet of ice (3,000 square feet bigger than any other sheet of ice in Florida — Olympic size.)

Our blades hit the ice at 5:30am for 30-minutes of compulsory school figures, a lost practice of slow and precise edges and turns, judged by the quality of the markings the skater leaves on the ice.

And unlike other figure skating disciplines, where judges perch comfortably on the sidelines, evaluating performances from behind the steam radiating from their coffee, those who judge figures walk out on the ice with delicate horse-hair brushes and magnifying glasses to scrupulously examine your etchings. 

Can you imagine anything more anxiety-inducing at 5:30 in the morning?

But although figures had been eliminated as an Olympic requirement by the time I entered the sport in the 90s, my coach insisted that her pupils practice them, and submit for testing. There was a right way to do this shit. And she wasn’t going to let standards slip.

After figures, we’d get our blood pumping for the next couple of hours, training our jumps, our spins, our footwork, and our power before the best part of our morning: breakfast break.

It was a full 30-minute break, but we’d scarf down our Pop-Tarts in one minute flat, and rush to an empty locker room where my glow-in-the-dark jump rope performed its most important job of the day — wrapped around whoever was “it” in our game of dark tag.

Because… we were kids.

Me with my famous jump rope, using it for the purpose it was actually intended — warming up.

We squealed and darted around the pitch-black windowless room, with nothing in our vision except the pale green glow illuminating from the jump rope tied around someone’s waist. 

Finally, a sliver of blinding light would cut through the darkness as somebody’s mom cracked open the door and shouted “Time to get your skates back on!”.

Back on the ice we’d go, training our tushies off for the rest of the morning.

Miss a jump in your program? You’d be ordered to skate 10 laps right after the music finished, already breathless, and on legs that felt like Jello.

Cut a lap short? That would earn you 20 pushups, center ice.

Collapse after 12 pushups? Alright, now everyone is lined up next to you, hands frozen into the ice, toe-picks holding a steady plank, completing the remaining eight pushups at a team.

We may have been adversaries at competition, but at training camp, we were bosom buddies.

The afternoon was reserved for off-ice training. Ballet. Yoga. Calisthenics. Weightlifting. Even rock climbing. If it improved strength, flexibility, or movement, we were doing it.

One particularly ruthless trainer even had us doing walking lunges around the entire perimeter of the building — on scorched pavement in the unforgiving Florida sun. We went from frostbitten fingers to puking from heat exhaustion. 

Think this all sounds like child abuse? You’re wrong. We were having the time of our lives, surrounded by our best friends, and achieving physical feats that our bullies at school could never dream of. 

This was probably the most unique thing about our situation—

We were Floridians. 

Unlike the frozen tundras of the Midwest or New England — where every mother’s birth canal is biologically altered to enable babies to be born with skates already strapped to their tiny feet — ice skating was a complete novelty in my home town.

And we weren’t simply ice skating. We were throwing ourselves into double and triple jumps with the grace of a ballerina, and the stamina of a goddamn racehorse. 

We were all gods.

How did I end up there?

By the time I was six years old, and had never seen snow, my Detroit-born father decided, “Enough is enough, my kids need a romp in the white stuff”.

And off we went on the only recreational family vacation we ever took. (After that, our travel budget was bled dry from my figure skating competitions and my brother’s hockey tournaments). 

Our destination was a mountain resort in North Carolina — the kind of place where we were guaranteed to see snow, regardless of whether or not it actually fell from the sky, because they were making it for skiing.

That was a good call. There was absolutely no natural snow to be found. 

So we frolicked at the base of the bunny hill, making snow angels, avoiding the skiers, and having the wintery fun experience my parents had planned for us. Mission accomplished.

Kudos, Mom & Dad, for the stylin’ snow suit.

Until one day we went for a drive, and stumbled upon a towering mound of snow near the road. Weird… where did that come from?

Turns out, we had found an ice rink. And not a stinky hockey arena — a beautiful outdoor rink, nestled in the mountains.

After a few minutes of watching us climb the Zamboni snow hill, my folks decided that it might be fun to throw their Florida beach kids on the ice rink to metaphorically “sink or swim”.

We walked in, and were surprised to have the place to ourselves. My parents bought skating tickets and rented us little skates. The sweet man working there said, “Don’t worry, I’ll refund you if the kids don’t like it. They’re a little young for this.”

Two hours later, they were dragging me and my four-year-old brother off the ice, kicking and screaming. No refunds were needed. We were both obsessed from the moment we stepped foot on the ice. 

I wanted to figure skate. My brother wanted to play hockey. And over the next few years, my parents made incredible sacrifices to get us into lessons and help us gain the foundational skills we would need to enter those sports — in a place where ice was sparse, and wickedly expensive.

Then one day we learned of a real estate developer who was considering building an ice rink in our town. Holy shit. That would be a game-changer for us.

So my parents reached out to him, offering their support.

That offer of support turned into them getting hired to run the place… Then taking over an ownership stake in the project… And finally buying it out entirely. 

We became the ice rink owners. This enabled my brother and me to pretty much live on the ice for the next decade, excelling in sports that shaped our entire future.

Thank god we ran into that mound of Zamboni snow in North Carolina.

Back to figure skating training camp…

I’m going to spoil it for you—

None of us ever competed at the Olympics. None of us even came close.

Partly because it’s a wildly competitive sport and we simply weren’t good enough, but also because it was an era of pubescent champions. Oksana Baiul was 16 when she took home Olympic gold in 1994, followed by two Americans who we all looked up to with stars in our eyes — 15-year-old Tara Lipinski in 1998, and 16-year-old Sarah Hughes in 2002.

With this trend of teenie bopper champions came an attitude of, “Oh, you’re 14 and haven’t qualified for Nationals yet? It’s already too late for you.”

All it took was one injury, and suddenly you had missed your chance. At least, that’s what happened to me.

Two weeks before I was slated to compete at Regional Championships (the first round of qualifying events for Nationals), I fell in training on the only triple jump in my program — a Salchow — and broke my hip.

I was 13 years old.

I fought the pain, gobbling up Advil like jelly beans, and got on the plane to compete at Regionals in Pittsburgh. I skated like shit, of course, and didn’t qualify for the following round.

The doctor told me I needed to take a year off skating to recover. I didn’t listen. I caused even more damage to my hips — damage that is still plaguing me to this day.

But I kept pushing myself… Summer training camps… Hours of practice before school… Competitions… Until the outcomes I had dreamt of were officially out of reach, and I retired from competitive skating at the washed-up old age of 16.

If the goal was a trip to the Olympics — I blew it.

And my friends? The ones who lined up shoulder-to-shoulder with me, performing pushups in the middle of the ice? The ones who actually showed up to my birthday party when my school friends cruelly bailed at the last minute? The ones who I fiercely competed against, then went out for pizza with an hour later?

We don’t look like rivals, do we? Yet we were all competing against each other. Wild.

They all experienced similar endings to their figure skating careers.

But they grew into remarkable f*cking humans.

Let’s look at Brittany and Joanna — my two closest skating friends. Brittany worked her ass off to become a doctor at an esteemed hospital, and Joanna is a successful entrepreneur. I beam with pride every time I think about them.

And me? I can trace every morsel of success I’ve achieved in my life back to figure skating. The discipline. The work ethic. The constant cycle of “preparation, execution, review”.

But more importantly, figure skating taught me how to fail — gracefully. And even in those painful moments of failure, to support your friends/opponents. No one else in the world understands your life in the same way they do. The depth of those relationships far outweighs the rivalry of competition.

Ilia Malinin, objectively the best figure skater of all time, failed on Friday. And his first instinct was to support his friend — the man who had beaten him.

I think we can all learn something from that.

Cheers! 🍻

-Kristin

I’d like to dedicate today’s issue to my life-changing coach, Sharon Martens. She drew the best out of us — as athletes, and as humans. Love you always, Big Red.

Five minutes into the first Olympic Curling event this week, the arena plunged into darkness. Whoops. 🥌 

But the athletes didn’t panic. Apparently the Olympic Curlers saw the blackout as an opportunity to dance and play air guitar with their brooms.

As someone who loves to curl, and can claim from first-hand experience that it’s the only Olympic sport one can perform while simultaneously drinking a beer (damn I wish someone had taken a photo that day), this behavior 100% tracks.

But do y’all remember when the power went out — at the Super Bowl?!

It was a tad more chaotic. And I’ve got the inside scoop on that madness for you today…

P.S. — It’s the last day to join Naked Newsletter Accelerator. Literally. We kick off TOMORROW! Omg.

🍻 THE DRUNK BUSINESS ADVICE

👉 Learning isn’t linear, so it pays to regularly revisit your past experiences

👉 You never know when a nugget from 20 years ago will save your ass today.

And now — the story behind why this advice matters. 👇️ 

Frank and the terrible, horrible, no good, very bad day

The year was 2013.

Inside the New Orleans Superdome, the Baltimore Ravens were leading the San Francisco 49ers 28–6 in front of a live crowd of 70k+ football fans.

Over 100 million viewers were tuned in globally.

And Frank Supovitz, the man responsible for producing the Super Bowl that year, was giving an interview to 60 Minutes from inside the NFL control room when something went “terribly, horribly, and spectacularly wrong.”

Shit.

Source: CBS/Showtime

The power mysteriously went out. Darkness rapidly engulfed the stadium.

What was happening? Was it a terrorist attack? A cyber attack? Was the entire city of New Orleans blacked out, or just the Superdome? Do we need to evacuate? Shelter in place? Cut the live feed because, ya know, we’re broadcasting live to millions of televisions around the world?

The confusion was palpable, and panic was beginning to take hold everywhere—

Except the control room. This was the kind of crisis that Frank had spent his entire life preparing for.

And he was the man in charge that day.

Let’s back up…

Frank Supovitz may not be a household name, but you’re familiar with his work.

Not only has he produced 10 Super Bowls ( 🤯 ), he also: 

• Led the NHL’s Events & Entertainment department for 13 years.

• Produced 31 League Drafts between the NHL, NFL, and MLB.

• Currently produces the Indy 500 pre-race show, among a ton of other events in the sports and entertainment world.

But I’d like to take you back to a sweet 15-year-old Frank — an usher at Radio City Music Hall…

Teenage Frank at Radio City Music Hall. Love the ‘stache.

“I was a child of the subway,” Frank told me. “If you can get to places, you can do things.”

Having proximity to such an iconic venue drew him in like a moth to the footlights.  And it was Frank’s time as a high school student / usher at the world’s most famous theatre that he stumbled upon a career-saving lesson:

But this lesson was lost on the executives at Radio City.

In their mind, the guest experience started when the curtain went up — not when folks stepped off 6th Avenue into the Art Deco palace that Frank was lucky enough to call his workplace.

They didn’t realize that:

• You have to count on everybody.

• You have to make clear to everybody what your objectives are.

• And you have to empower everybody.

You might be thinking, “Wow, what a great lesson to learn so young!”. Except Frank didn’t really learn this lesson. At least, not as a teenager.

“Learning is not linear”, Frank reminded me. “Changing how you do things is not linear. So although I learned that at Radio City, I didn’t really come to understand that until I got to the NFL” — 20 years later.

Well damn. That means that for 20 years of his career, Frank was sitting on absolute gold without even realizing it.

But that’s ok, because the lesson saved him when he needed it the most.

The game day transformation 🏈 

By the time Frank found a home at the NFL, the organization had begun re-thinking the stadium experience. Ticket sales were steady, but attendance was dropping. Broadcasts featured rows and rows of empty seats. Not a good look.

People were literally buying tickets to games — and not going.

WTF. 🤨

Frank and his team realized that it was no longer good enough to simply put on a great show inside the white lines. Clearly, something was keeping these folks out of their seats.

Every step of the fan’s journey was vitally important, yet they were only focusing on what happened on the field. It was Radio City Music Hall all over again. But this time, Frank was in a position to make a change.

So he brought in the big guns —or should I say— the top mouse.

The Disney Institute worked hand-in-hand with the NFL to transform the game day experience from one that was full of long lines, horrible hassles, and grumpy security guards, into…

Ta-Daa! Source: Giphy

This is when Frank made a major structural improvement that had not yet been attempted in the world of broadcast sports — he put the front-line forces in direct communication with the control room.

Recalling his own experience as a front-line worker back at Radio City, Frank realized that he needed to empower those guys by “inverting the pyramid” and prioritizing the people who were —ya know— actually interacting with customers.

What a concept. 🤷

Frank’s famous inverted pyramid.

That concept saved the Super Bowl…

Back to the Superdome blackout, where Frank didn’t take control of the situation — or at least not Frank “the man” per se. It was the system Frank set up for quick decision-making and clear communication that took control.

This system allowed him and his team to get out of their own heads (and ignore their soiled trousers) to focus on finding a solution to the problem.

To be clear, lots of meticulous planning, quick thinking, and talented people contributed to the professional handling of Super Bowl XLVII’s blackout—

👉 But it was the culture-shift of empowering the front lines that Frank initiated which kept everyone at work that day calm, collected, and in control.

What could have a been a catastrophe of biblical proportions turned into a small sliver of sports history that many may not even remember.

Frank’s book, What to Do When Things Go Wrong, dives deeply into his thorough approach to crisis prevention and management. (I highly recommend you read it. It’s my bible, and has saved my ass on more than one occasion.)

But I believe that Frank’s true genius lies in his ability to remain connected to his past experiences. He doesn’t just ask questions of the people around him — he asks those same questions to past versions of himself.

It’s easy to move on from an experience, collect your immediate learnings, then put it to bed. But there’s far more juice left in that squeeze for folks who are willing to hop in a time machine and revisit “finished” chapters of their career.

Because if you pay attention, those chapters are never truly finished.

Cheers! 🍻

-Kristin

P.S.— One of the best ways to access lessons from your past chapters is to start writing a newsletter. This is precisely what it did for me. So join Naked Newsletter Accelerator and we’ll get your newsletter launched together. 👊 

Today, I’m going to answer the most frequent question I’ve been asked since launching Drunk Business Advice back in 2024.

Not because I’ve been keeping it a secret.

Because I finally have an answer.

Thank god.

P.S. — It’s the last day to join Naked Newsletter Accelerator for $299. Naked is better with friends. 😉 

🍻 THE DRUNK BUSINESS ADVICE

👉 If you don’t examine your own process, you’ll never be able to teach a goddamn thing.

👉 And if you don’t teach a goddamn thing, you’ll never improve your process.

And now — the story behind why this advice matters. 👇️ 

The gospel of Jacob

Anytime an industry lowers its barrier for entry, markets get flooded. Investment dollars follow, values get inflated, quality goes down, and then… pop.

This can absolutely be said for the newsletter industry.

But the talented and fearlessly honest Jacob Cohen Donnelly, founder of A Media Operator, has famously (and repeatedly) said:

And I couldn’t agree more.

Here’s a photo I took of Jacob saying this to Katie Couric. Probably. I can’t remember exactly. But he definitely said it at some point on stage at the AMO conference.

When Jacob and I aren’t sucking down martinis while trauma-bonding (possibly based on a true story), we’re busy building media businesses that center around our (we hope) un-shitty newsletters.

But here’s the thing about un-shitty newsletters… They're not just anchors for successful media businesses. They are an unbeatable tool for building trust, no matter what your end goal is.

Which is why earning trust should be the #1 objective of any newsletter. With your audience’s trust, any goal is possible. Without it, no goal is possible.

Whether you want to…

…promote your business…
…earn subscribers who pay for content…
…monetize through sponsorship…
…attract new opportunities…
…advocate for a cause…
…shape the culture of your industry…
…get your ideas adopted by people who matter…

…it all boils down to one thing. 👇️ 

Billy Joel was the most compelling philosopher of the 20th Century. Fight me on it. Source: Tenor

I'd be hard-pressed to uncover a situation where building trust with your audience is not a worthwhile endeavor. A great newsletter will undeniably aid this process.

And it’s literally never been easier to start a newsletter. Which, for most people, means it’s literally never been easier to start a shitty newsletter.

Don’t be most people.

What should your newsletter be about?

Since launching Drunk Business Advice, many of you have reached out for my feedback as you considered launching your own personal newsletter. And the most common question I dodged was:

👉 “What should my newsletter be about?”

So… why was I dodging that question? Let me be clear… and this is very important…

Because I didn’t have a goddamn clue how to answer it. 

It’s like when people would ask me “How can I write like you?” …I dunno. I just… write. I didn’t know how I did it, or how to teach it. But I wanted to know how I did it. I wanted to be able to teach it.

So I put my writing process under a microscope. I spent months asking myself questions. I asked other people to ask me questions. I recorded everything. I even instructed AI to analyze every article I ever published to detect patterns that human eyes can easily miss.

And in the end, I was finally able to deconstruct my process with enough clarity and precision to teach it to others — which I began doing last year with a writing cohort called Rebel Scribes, and a premium instructional newsletter called Drunk Writing Advice.

Working with real people who were deploying my writing process gave me even more clarity. The more I taught, the better I got at analyzing and improving my own shit.

So why am I telling you this?

Because I recently underwent a similar protocol to finally be able to answer the “What should my newsletter be about?” question. And I’m going to share it with you now.

Your badass zone

_{This is a little preview of the Naked Newsletter Accelerator curriculum, kicking off February 9th. Today is the last day to register for $299. Let me help you find your badass zone.}

Damn, I really love a good Venn diagram. There’s something so clarifying about visualizing the intersection of seemingly unrelated virtues that, when joined together, spark something uniquely new.

It’s the soul of creativity.

So. What should your personal newsletter be about?

The theme of your personal newsletter should live at the intersection of:

• Value: What can you share with your audience that inspires them to take action?

• Authority: Where do you possess undeniable credibility?

• Vulnerability: Where have you faced moments of personal failure, crisis, uncertainty, or transformation?

This intersection is unique to every person. It’s not a slave to trends. It’s the center of both your genius and your most transformational stories. It’s the area where you can have the biggest impact on the world. It’s your badass zone.

Now — you might enjoy some good personal newsletters which nail two out of three of these things, and assume that’s enough. 

But I predict the ones who don’t already have a massive foothold (like a fandom beyond their newsletter) will get squeezed out. Maybe not as quickly as the shitty ones, but as space in the inbox gets even more competitive, they’ll fall to the bottom. Here’s why:

It’s about time

If you had told me 20 years ago that I would be writing a newsletter called Drunk Business Advice…

I’d probably believe you.

Because Drunk Business Advice sits well within my badass zone, and evidence of this dates all the way back to the beginning of my career. 

Sure, I didn’t have nearly as much authority as I do now, but even then, my favorite thing about my job was helping other people get better at their jobs — and I f*cked up a few times before really getting good at it.

See how it tracks?

I’d love to help you find your own badass zone. Today is the last day to register for Naked Newsletter Accelerator for $299. Stop dancing around this stuff, and commit to taking action. It all kicks off on February 9th.

Let’s work together. It’s my favorite thing to do.

Cheers! 🍻

-Kristin

P.S.—

👉️ Already have a newsletter? Naked Newsletter Accelerator will make the content better, and the operation easier to manage.

👉️ Not sure if you want a newsletter? Naked Newsletter Accelerator will improve your content, and your system for creating it, no matter which medium you prefer. But you should probably go ahead and launch a damn newsletter. 😉

👉 Don’t trust me yet? That’s fair. Here are some business badasses who have worked with me:

It feels a little –ahem– “cold” to be making a business announcement while half of North America is dealing with the worst winter weather event in recent memory, but I’ve decided to stick to my plan on this one—

If you’ve ever thought about launching your own newsletter, you won’t have a better chance than this. 👇

That’s right. I’m launching a new course called Naked Newsletter Accelerator, and oh lordy, I’d LOVE for you to join me! It’s far more fun to be naked together than naked alone. 😉 

🍻 THE DRUNK BUSINESS ADVICE

👉 If you have a newsletter, it should definitely be “naked”. It’s the fastest way to build trust.

👉 Surrounding yourself with talented people who care about your goals as much as you do is the most important business decision you’ll ever make.

And now — the story behind why this advice matters. 👇️ 

It took me a goddamn year to launch the Drunk Business Advice newsletter

It makes me a little queasy to admit this, but it’s 100% true.

And I’m not saying, “Oh, I had a vague idea for a newsletter, and it just fell to the back burner for a year until I was ready to get serious about it.”

No — I began taking concrete steps toward launching Drunk Business Advice a full year before I actually published my first issue.

If you need proof, he’s an old test issue in my current email platform that I PUBLISHED in July of 2023. I didn’t launch Drunk Business Advice until April of 2024. 🤦

And here’s the shittiest part — I actually knew a little bit about publishing newsletters. Having worked at The Hustle for a couple of years, I was far from green.

But managing editorial for an established publication is quite different from launching a scrappy personal newsletter. I had a clear view of the outcome I wanted, but I didn’t know what steps to take to get there.

So I went in circles… playing with points-of-view, toying with tech, deliberating on distribution channels, drafting and re-drafting and re-re-drafting welcome flows and landing pages and test issues… until I had buried myself under mountains of mediocre manure. 💩

Then I had to figure out how to dig myself out from under the manure mountain.

Frankly, my arms are still a little tired.

So how did I finally get here? How did I navigate my way out of the fog? How did I manage to actually launch this newsletter back in 2024, and continue to publish it every damn week since then?

I’ll share all these juicy details with you in the upcoming Naked Newsletter Accelerator. 😘

It shouldn’t be that hard

If it took me –someone who actually knows a little bit about newsletters– a full year to launch Drunk Business Advice, how long might it take someone else to launch a quality personal newsletter?

How long might it take… you?

There are dozens of indisputably good reasons why a business leader should be publishing a personal newsletter. But it really boils down to this— 

Showing up consistently for your audience with personal stories that deliver value is the fastest way to earn trust.

So whether your goal is to get hired… get people to buy from you… get people to want to work for you… or get people to pile your lap full of opportunities… publishing a personal newsletter is a no-brainer. It will definitely GET YOU NOTICED.

But if you fill it with directionless, generic, putrid, AI slop, you will be forgotten in an instant. Or worse — you’ll garner distrust. 

So there’s a lot of pressure to get it right. And that’s one of the reasons it took me so damn long to launch Drunk Business Advice.

But it doesn’t have to be that hard. You just need a little help. Here’s what we’ll cover in Naked Newsletter Accelerator: 

👉 Doing the right shit in the right order. I’ll give you the precise steps to take to launch your powerful personal newsletter in four weeks. Don’t get swept up in a tornado for a year (like I did) — just follow the yellow brick road.

👉 Templates that really work. You don’t need hundreds of email templates. You just need ones that actually work. I’ll be sharing subscriber flows that have earned me 80%+ open rates, and 50% click rates, while teaching me a ton about my readers. 

👉 Personalized support. We’ll have six LIVE coaching calls that exist for the sole purpose of getting your questions answered. You’ll also meet other business badasses who share your newsletter goals.

👉 A sustainable system. After publishing an average of 1,500 words per week for 90+ weeks straight, I’ve incorporated everything I’ve learned into a killer content planning platform. Never stare at a blank page again. Oh, and I’m giving you access to it for an entire year. 🤯

Time to get naked…

So what, exactly, is a “Naked Newsletter”?

A Naked Newsletter cuts the B.S. and inspires the reader to trust you.

People don’t trust super polished content. They trust real people who share honest experiences, critical mistakes, and embarrassing flaws.

Which can be pretty hard when you’re this damn flawless. 👇 😘 

Ooh, la la! No, this is NOT a real picture. It’s my face photoshopped onto a famous photo of Demi Moore. I know some weirdo out there won’t read this caption, and will think it’s real, but PLEASE KNOW THIS IS A JOKE OMG!

Ok… time for me to actually get naked, jokes aside. 😉

I fear I never would have found the right path to launching Drunk Business Advice if it weren’t for one man: Rob Capili.

Rob and I were both in Stealth Mastermind, a community for experienced entrepreneurs. I wanted to launch a newsletter. Rob wanted to launch a YouTube channel. So we decided to work together.

Rob had never launched a newsletter, and I had never launched a YouTube channel, so you’d think we were the blind leading the blind. But we provided each other with the three things we both desperately needed:

1. Accountability

2. Brutally honest feedback

3. And a deadline

This is when I realized that surrounding myself with talented people who care about my goals as much as I do was the most important business decision I would ever make.

And this is why I’ve decided to deliver the Naked Newsletter Accelerator as a group course. 

Aside from you and I getting to know each other better through this process, I’d love for you to find the kind of peer support I received from Rob, who remains a vitally important partner to his day:

Get yourself a friend who enthusiastically jumps to deliver the most wildly outrageous favors with zero context and zero questions asked. 😆

I sincerely hope you’ll join me! It would truly be an honor to help you launch your personal newsletter. We’re gonna have some fun. 😘

Cheers! 🍻

-Kristin

P.S.—

👉️ Already have a newsletter? Naked Newsletter Accelerator will make the content better, and the operation easier to manage.

👉️ Not sure if you want a newsletter? Naked Newsletter Accelerator will improve your content, and your system for creating it, no matter which medium you prefer. But you should probably go ahead and launch a damn newsletter. 😉

Who the f*ck did I think I was?

I was just a 20-something nobody. These were important men who did important work. Why in the world would they hire me as a consultant?

Perched high above the humming Manhattan streets, I was nervously quivering inside the most wildly intimidating board room I had ever seen.

I couldn’t focus. The iconic Brooklyn Bridge loomed just outside the window. It taunted me with its tenacity and importance.

Oh god. 🤦 

🍻 THE DRUNK BUSINESS ADVICE

👉 Stop selling. Start solving.

👉️ The gap between what they assume, and what you know to be true, is where all your leverage lies.

👉️ The trick isn’t learning to talk better. It’s not even learning to listen better. It’s learning to see better. 

And now — the story behind why this advice matters. 👇️ 

What is a consultant?

I’ve thought long and hard about this question, and eventually settled on the following three definitions:

If you happen to be a consultant, and you’re reading this newsletter, I dearly hope you fall under the first definition — otherwise we’re going to need to have a little chat. 

That first definition also applied to me for a period of my career. In my case, I realized that I had unique expertise that could benefit a lot of blue chip real estate companies. But I had an employability problem — most of those companies didn’t require my expertise on a permanent basis.

And let’s face it. I’m a shitty employee. 🤦 

So I was stuck taking jobs that leveraged a little bit of my “special sauce”, but mainly filled my plate with stuff that I could competently do, but wasn’t thrilled about. I got bored quickly. I got annoyed by the red tape and politics. And I would give my left tit to never get called into HR again.

Finally, in my late 20s, having spent most of my young career launching new subsidiaries for established firms, and co-founding a successful startup of my own, I decided it was time to zero-in on my expertise, and establish a consulting practice as my full-time focus.

I figured that since I was already an “experienced entrepreneur”, running a consulting business would be a breeze.

Um. No. 

Just because you’re an in-demand-subject-matter-expert, or even an experienced businessperson, does not mean you’re qualified to run a consulting practice. Pretty much nobody is when they start. And nobody actually realizes how unqualified they are when they start, either.

Operating a consulting business is a skill that no one possesses until they do it for a while. Every time I talk to someone who is new at consulting, the same questions arise:

• “How much should I charge?”

• “How do I screen clients?”

• “How do I fire clients?”

• “What should I do when a client doesn’t take my advice?”

• “How much of my expertise should I “give away for free” to sign clients?”

Those are all important questions, but none of them matter until you’ve established the critical gap between what your client assumes, and what you know.

It’s much faster and easier to flip an assumption than to educate from scratch.

And guess what? This nifty little trick applies far beyond consulting. So listen up.

Back to the boardroom…

…Where I was anxiously prattling to three men in dark suits — two of whom were definitely old enough to be my father. These guys were incomprehensibly busy, and I was stunned that they all agreed to meet with me that day.

So, in the blessed short time I had with them, it was my mission to:

1. Convince them they had a problem

2. Demonstrate why I was the only one who could solve it for them

This was my first major pitch. I had launched my consulting practice only a few months prior, and none of the client conversations I had conducted thus far came close to the size and significance of the project this team was working on—

The redevelopment of New York City’s Seaport District following the devastation of Hurricane Sandy.

The guys on the other side of the table were legendary pros. George Giaquinto was the VP of Development for The Howard Hughes Corporation (yes, that Howard Hughes) – the lionshare holder of real estate in the Seaport District.

Bill Flemm ran operations for The Howard Hughes Corporation, connecting the dots across all the various initiatives.

And Frank Supovitz, like me, was a consultant — but with a profoundly beefier resume. Having directed the Super Bowl for a decade, he was now lending his entertainment production knowledge to projects like this one.

I had no clue what I was doing in that room with such giants. 🤷 

They walked in, shook my hand, and George immediately scoffed, “So how much is this going to cost me?”.

*Cue Kristin shitting her pants.* Source: Giphy

George tightly gripped the purse strings for the redevelopment project — as well he should. He was accountable for every penny that was spent, and the leaders of each initiative kept asking for more and more pennies.

So from his point of view, these guys better have a damn good reason for wanting to throw money at yet another “consultant”.

I knew in my gut that I could add enormous value to this project, but my own fluttering nervousness made the room unbearably tense. I was stumbling — sputtering like a beat-up Vespa, sliding down a cobblestone street in the rain. I spat out some words that seemed correct, but had no clear direction. "The operational efficiency of your development will depend on..." 

What an unfortunate moment to learn that I’m ego-crushingly terrible at pitching myself.

Shit.

A few minutes into my self-imposed corporate crucifixion, with the conversation going nowhere, the big boys took pity and decided to roll out some blueprints — literally. And when those drawings graced our table, a portal in my mind swung open.

It was goddamn Amazing Grace. I once was lost, but now am found — was blind, but now I see. I said a little prayer thanking the gods of real estate, because I had truly been saved.

With the plans rolled out in front of me, I could immediately visualize how people would move through the spaces they were building. I knew exactly how the elements of the operation would play out in practice, and could anticipate where things were bound to go wrong. I saw dozens of assumptions I could easily flip.

Finally. I could stop selling. I sucked at selling. I still suck at selling. Instead, I was nose-to-nose with a plan that was rife with problems — and I had solutions to those problems.

So I started solving.

I stood up, and leaned over the drawings. I pointed to design elements, asked questions about their placement, highlighted the issues, and proposed solutions.

This was my kill zone.

I had been so small and meek sitting in that chair — desperate, intimidated, and terrible at “pitching”. Now I was taking up space, controlling the conversation, and showing these guys the value I brought to the table.

I will never forget (nor could I ever repay) what Frank did after about 20 minutes of this. He stood up and said, “Guys, this is the stuff Kristin gets paid to talk about. I think we’ve heard enough to decide if we want to work with her.”

A few days later, they hired me.

The gap you should neatly nestle into

It was pure, dumb luck that this particular meeting went the way it did. And I’m grateful every damn day.  Not only because these guys ended up becoming my most valued and enjoyable client relationship — but because, in the short meeting I barely deserved, I got a knuckle-busting crash course on how to run a consulting business.

It’s a simple formula:

1. Identify the assumptions your prospective client has.

2. Flip one.

3. Shut up. (Hat tip to Frank). They can pay for the rest.

Moving forward, whenever I was prospecting a new client, I did my best to procure some sort of visual representation of what they were proposing — because I understood what an important mental unlock it was for me.

Sometimes this involved walking a physical site. Sometimes they had blueprints. And in the absence of those two things, I asked for detailed descriptions that I would personally map out on paper to give myself context before the meeting. Hell, even a napkin sketch would get me halfway there.

Once I had some sort of visualization, their incorrect assumptions became stupidly apparent to me — but not to them. And the gap between what they assumed, and what I knew to be true, was where I thrived.

Frankly, it’s where we all thrive, no matter our profession. But we have a tendency to make asses of ourselves long before that gap actually presents itself.

Why?

Because we’re all trying to look insightful and important. We interrupt. We posture. We try to solve problems we barely understand because silence feels like surrender, and nobody wants to be the one caught without a brilliant comment when the spotlight swings their way. 

So we speak first. Or loudest. Or most. Because in this pungent, performative bullshit stew of perception-over-progress, waiting feels risky. We’re wired to chase the mic like it’s a goddamn oxygen tank.

In that fateful meeting, I walked in with a vague understanding of their problem, slid right into my pitch, and completely shat myself in the process. I thought “This is my time to talk, I better not waste it.”

But the trick isn’t learning to talk better. It’s not even learning to listen better (most clients have no damn clue what their problems are anyway).

It’s learning to see better. 

The fastest way I found to do that was by literally laying the problem out on paper. When I could visualize it, I could spot the assumptions. I wasn’t guessing anymore, or trying to “sell” them on my expertise. Instead, I was diagnosing problems. And people would listen, not because I demanded the floor, but because I had real solutions.

The smartest people in the room don’t have it all figured out — they’re simply experts in quickly identifying the gap between what other people assume, and what they actually know.

That gap is where all the leverage lives. ✌️ 

Cheers! 🍻

-Kristin

Hand up if you hated high school. 🙋

Then consider yourself forewarned — today’s issue will trigger some eye-rolls you may never fully recover from.

Now, hand up if you’ve ever dealt with HR bullshit.

Same warning.

🍻 THE DRUNK BUSINESS ADVICE

👉 Don’t make stupid rules.

👉 If you find yourself defending a stupid rule, you’re probably defending your own ego.

👉 And if you find yourself battling a stupid rule, try lying. It usually works. 🤷 

And now — the story behind why this advice matters. 👇️ 

High school suuuuuucked

Let me be clear — I don’t think it’s “cool” to hate high school. I truly wish I had an amazing experience filled with tons of friends, school dances, football games, and classic coming-of-age moments.

It would have been so much easier. Source: Giphy

Instead, I had a helluva time fitting in at pretty much every level of the ecosystem — and not just with my classmates. Even teachers and administrators didn’t really know what to make of me. And I was just a kid, so I didn’t know what to make of myself, either. 🤷

It was a confusing period. But in 10th grade, I was tossed a lifeline:

I was accepted into a college dual enrollment program. 📚

This meant that I didn’t have to physically attend high school anymore — I was able to complete all of my classes at a local community college, and work full-time in my family’s business.

So at 16 years old, I stopped going to high school, and ventured into the “adult” world.

The following year, I was invited to enroll in a special early admissions college program in NYC, which meant leaving my sleepy Florida town, and moving into a Brooklyn dorm room.

Dinner on the floor of my dorm was a regular occurrence. And I f*cking loved it.

It was heaven. I finally felt like I was living a life that belonged to me.

But then they changed the rules — for seemingly no reason whatsoever 🙄

One day, my mom received a dramatically upending phone call.

She was informed that the school district had changed the rules for my dual enrollment program, and I had already “maxed out” the number of college classes I was permitted to take under the new rules.

So, for the second semester of 12th grade, they were forcing me to GO BACK TO HIGH SCHOOL. 🤯 

It was inconceivable to me. I had been living as an adult in New York City for f*ck’s sake.

I fought the decision, but since the public school system isn’t exactly known for its flexibility and understanding, I was forced back into high school — only a few months before graduation.

It was torture. So in an act of short-sighted rebellion, I rarely showed up for class. If I didn’t have a test or an assignment due, I just blew off school all together. What were they gonna do? Fail me?

Yep. 😳 

About a week before graduation, I got called down to the office… Where the Assistant Principal told me that she was going to fail me. ❌ 

How was that possible? I had A’s in all of my classes, a 4.2 GPA, and was the only student to have earned a perfect score on the statewide standardized test — twice.

Apparently that didn’t matter. I was informed that, at their discretion, the administration could fail a student simply due to absences, no matter what their grades were.

So I did what any desperate kid would do:

I forged a letter from my Mom claiming that the Mono I had in 7th grade had relapsed, and requested that all of my absences be excused due to my medical condition.

Listen to Ferris Bueller if you won’t listen to me. Source: Giphy

I doubt the Assistant Principal believed it, but she reluctantly allowed me to graduate. After all, she had made her point and “taught me a lesson” about the importance of following asinine, arbitrary rules.

Years later, I learned that my Dad lied to his high school about getting a girl pregnant so they’d let him graduate without one stupid PE credit he was missing.

I invented a disease to graduate, he invented an entire family. Well done, Dad! Fight the power!

And this is the story of how I learned that lying is totally acceptable when you’re forced to follow a stupid rule.

This shit extends far beyond high school

As a teenager, I thought stupid rules existed so that fatuous adults could control independent-minded kids.

Turns out, stupid rules also exist so that fatuous adults can control anything that threatens their ego.

About 10 years ago, I was hired by a large global firm who was (secretly) looking to acquire a company in an adjacent space to expand its offer. They knew me because I had been a big client of theirs in that adjacent space, and they wanted me to help facilitate the acquisition, then oversee that new division.

It was a killer opportunity, and I jumped at it.

But not long after I joined the team, the CEO got himself fired, and the acquisition plan was put on hold. Instead of letting me go, they threw a bunch of other projects my way. Some I enjoyed, but most had me doing things that were outside of my expertise and interest, and they were killing me with travel.

After about a year of this, it was time for me to step out of limbo. I sat down with my boss, and explained that I would be resigning in eight weeks.

However, I told him that I was willing to stay on if I could transition to non-traveling role, focusing on some key projects that would prepare the company for the eventual acquisition.

Y’all — this was NOT a contentious situation.

We’re all friends here. Source: Tenor

I was resigning with generous notice, while giving the company an option to keep me on if they felt they still had a need for the unique skills I brought to the table. My boss understood my position, and appreciated my thoughtfulness. He circled back to me shortly after with a decision for me to stay on, and told me that he and the other stakeholders were happy with the terms I had proposed.

Cool beans. After 8 weeks, as promised, I transitioned into my new role.

But the company wasn’t in great shape, and less than a month later, the board voted in favor of a headcount reduction.

❌ I got the ax, along with many colleagues. And they only gave everyone 2-weeks severance.

This was a pretty shitty thing for them to do to me, given how transparent I had been with them. They should have just accepted my resignation, which would have given me ample time to line up other income sources before leaving the company.

But I recognized that the layoffs were outside of the control of those who wanted me to stay, so I only had one request:

I wanted my employment record to reflect that I had resigned on good terms with plenty of notice — not been laid off.

My boss thought it was a reasonable request (since that’s what should have happened), and put me in touch with the HR Director to coordinate it.

Unfortunately, I didn’t look up the term “haughty bitch” in the dictionary before talking to this woman, else I would have seen her photo and been prepared for the utterly absurd conversation I was about to have.

It was high school — all over again. 🤦 

Um. What.

I hopped on the phone with the HR Director to explain the situation, and respectfully request that my record be updated.

She outright refused, saying that if she did it for me, she’d have to do it for everyone they had just laid off.

Well that makes no sense. Source: Tenor

Um. No.

I pointed out that no one else had resigned with 8-weeks notice, and agreed to stay on longer at the company’s behest — only me. 🙄

So then she decided to hold my pitiful little severance hostage, telling me that if she changed my record, she wouldn’t allow payroll to deposit the two weeks of salary I was owed.

That was the rule — if I “resigned”, I wasn’t owed severance. No thoughtful discretion. Apparently.

She literally huffed when I rebutted that I had provided the company with 8-weeks notice, so if they had simply accepted my resignation when it was given, I would have no need for severance.

And if the words coming out of her mouth weren't disgusting enough, her attitude was unreservedly vile. I felt like Oliver Twist, begging for more gruel. 

MOOOOOOORE?! Source: Tenor

Before I worked for this company, I had been one of their biggest clients, engaging them for projects worth millions of dollars. 

And just because I wasn’t going to be employed by them anymore didn’t mean I was disappearing from the industry. In all likelihood, I would be returning to my previous status as a vital f*cking client.

Her top priority should have been ensuring that my departure from the company was handled with enormous care, and a desire to continue our longstanding relationship.

Instead, she wanted me to sign a document that stated that if she did what I asked, I would “never seek employment” with the company again. 🤯

Not wanting to say something I would regret, I finally gave up, thanked her for her time, and hung up the phone.

The CEO eventually made things right with me when he became aware of what happened. (I really hope he fired her, but haughty HR bitches have an innate way of clawing their acrylic nails into big companies for decades.)

As expected, I returned to my status as a client, and continued to engage them for projects in the years that followed. But the damage I could have done to their company, not just by withholding my own business, but through my sphere of influence with their other major clients, would have lost them tens of millions of dollars.  

All because some HR Director wanted to assert her authority.

👉 Just like my high school Assistant Principal, all those years before. 

They were the same person, using arbitrary “rules”, and the tiny amount of power they had over me, to feed their own egos.

But as much as these stories conjure up old feelings of red-hot anger, those emotions are quickly replaced by something rather surprising—

Peace. 💜 

Not because it’s natural. Because I’m choosing it.

And the next time you’re in a situation like this, I encourage you to do the same.

Cheers! 🍻

-Kristin

The last corporation I ever worked for had recently laid off 500 employees when they called a virtual all-hands meeting across the entire company.

I was not one of the employees they had just laid off. 

Probably because I had already absorbed an entire second role without a penny added to my salary — “There will be no raises this year,” HR reluctantly revealed when I (first) nicely asked for, then later demanded, higher pay for twice the work. 🤦

🍻 THE DRUNK BUSINESS ADVICE

👉 You’re not crazy. They really are trying to convince you that less money for more work is a gift.

👉 Always question a word salad. If they can't explain it in plain language, you don’t want what's being served.

And now — the story behind why this advice matters. 👇️ 

A bunch of nincompoops

The company was in trouble. They were attributing our collective woes to shifting market conditions, and downplaying the reality— 

The reason we were in such a sticky wicket was because of a series of neglectfully short-sighted leadership decisions which failed to recognize that… ya know… market conditions can shift.

So thousands of employees from across the globe jumped on Zoom to listen to the C-Suite spout canned excuses and respond to carefully pre-selected questions from the workforce.

It. Was. So. Icky.

I just wanted it to end. Source: Giphy

But it was also exactly what I expected. Except for one thing that floored me—

They knew they had to address the fact that they weren’t giving raises to anyone, even folks who got promotions or absorbed more work. So they presented an anonymous “question” from the audience to the CMO. It was something like:

“How will this year’s revised strategy impact our own personal career progression?”

The CMO took a moment and pretended to think about his (obviously pre-rehearsed) response.

Then he said (I’m paraphrasing, but this is pretty damn close to an exact quote):

I couldn’t roll my eyes hard enough at that spin. 🙄

But there it was. He had just told everyone what I already knew — we were all going to have to do more work for less pay because the executives had shit the bed. 

The Zoom chat immediately lit up like a Christmas tree, and I thought “Lord, he’s about to have thousands of people call out his crank.”

But that’s not what happened. Instead, everyone was like:

👏 “WOW, that’s so true, progression isn’t linear, how insightful!”

👏 “What a great opportunity, I’m honored to work here!”

👏 “So pumped for this new direction!”

And a million heart and applause emojis flew across the screen. ♥️👏

What in the actual f*ck.

Were these people brainwashed Kool-Aid drinkers? Or just plain morons? How was it possible they didn’t catch the meaning behind the CMO’s carefully curated word salad?

That was the moment I began planning my escape. It’s one thing to be asked to do more work for less pay because the company is in trouble. But it’s total bullshit to frame it as an “opportunity”—

And I wasn’t going to work with a bunch of nincompoops who actually believed it. 💩

She was diabolical

Look — I certainly can’t claim that I’ve never allowed myself to be manipulated. I have absolutely fallen for bullshit.

One interaction that still keeps me up at night involves a well-known executive (my former boss) who is an absolute master of plausible deniability. She puts dirty politicians to shame.

Let’s face it. ALL politicians are dirty. Source: Giphy

And because of her overall shittiness, the place had become an intolerable work environment. So as soon as an opportunity presented itself elsewhere, I noped right out of there.

The day after I submitted my resignation notice, she called me into her office. I was fully prepared to tell her exactly why I had quit. Burn that bridge. 

Instead, this was the conversation:

She didn’t ask a single question, or open the door to a conversation. Instead, she masterfully manipulated the exchange by making statements that were technically true — which forced me to agree — then showed me the door.

After that, she could truthfully tell anyone who asked, “I spoke to Kristin, she’s leaving because she got a great opportunity, and we couldn’t convince her to stay.”

But if I had been prepared to expect her bullshit, I would have responded to “So, I hear you’re leaving us for a great opportunity,” with “Nope, that’s not all…” — and laid it on her.

But even that kind of preparation wouldn’t have been a match for her expert-level bullshit spinning, as was evidenced by what happened to one member of my team who quit shortly after I did.

Knowing how she had manipulated my conversation, he didn’t hold back, and listed all of the unsavory reasons he was choosing to leave the company, concluding with:

“For my own mental health, I cannot tolerate it here any longer.”

Bingo. He gave her exactly what she wanted. 

She turned around and told everyone he was leaving for “mental health reasons.”

That one was pretty diabolical. It still pisses me off. Especially since she’s still with that company, and even got promoted.

Bullshit.

Nobody joins a cult

There’s a popular saying: “Nobody joins a cult”. It means that nobody chooses to be manipulated, exploited, or bullshitted. Because at the beginning, manipulation, exploitation, and bullshit are disguised as things like:

• An unmissable opportunity

• Personal growth

• Passion-driven work

• Mission alignment

• The solution to your problems

By the time you realize you’ve been bullshitted, it feels a helluva lot harder to get out than it was to get in. So you sink deeper. You lie to yourself. You become the bullshitter.

And I’m not just describing an actual cult here—

This is a bullshit workplace. A bullshit partnership. A bullshit client relationship.

And you’ve probably been in one. In fact, you might be in one right now.

I’m so sorry. Source: Giphy

If you think I might be describing you, my advice is to take two simple steps:

1. Pretend to not understand

Bullshitters use language loopholes to get people to agree to things they wouldn’t usually agree to, like that wily CMO who said “career progression shouldn’t be linear”.

Everyone knew what those words meant individually. Most of them probably even knew what they meant strung together. But what they didn’t know was why they were chosen.

This is where a simple “What do you mean by that?” comes in handy. Even if you think you understand what they’re saying, force the bullshitter to speak in plain language. And if you don’t like what you hear…

2. Abandon sunk costs

Bullshitters keep a carrot inches from your nose at all times, so keep a close eye on moving goalposts.

You’re always just days away from that promotion, that promise of an important project if only you’ll complete one more menial task for that obnoxious client, or that “Double Diamond Ambassador” level if you can just recruit 10 more housewives to sell ugly leggings. 

(Lord, I hope there aren’t actually any pyramid schemers on my mailing list…)

You think, “I’ve worked so hard to get this far, I can’t give up now…” — but you absolutely should. Trust the part of you that’s embarrassed to have put so much time/effort/money into the bullshit, and get the f*ck out.

Cheers! 🍻

-Kristin