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My Life In Four Leaps

We’ve added over 1,000 new subscribers in the past two weeks, so I figured now’s the right time to take a step back and share a little more about myself.

Not the shiny LinkedIn version. The real version. The messy, terrifying, “holy sh*t, did I just blow up my life?” version.

Risk-taking gets dressed up like it’s some heroic act in TED Talks. The truth? It’s horrible. It’s waking up at 3am with a pit in your stomach. It’s doing math on the back of a napkin and realizing you’ve got maybe three months before you’re broke.

I should know. My life has basically been a series of reckless leaps. Here are four of them…the ones that shaped me, terrified me, and somehow landed me here.

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Single Income Households…

Last week, this post popped off. And it led me to finally cross 10,000 followers on LinkedIn!

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Leap One: The Bluff

In 2017, I was a finance student at Butler University. Mondays, Wednesdays, and Fridays, I worked at Charles Schwab in what was pitched as a “fancy apprenticeship.” It paid well ($27 an hour) but it sucked.

While my friends were out on Thirsty Thursday’s, I was setting a 5am alarm to cover pre-market trading. My life at 21 was basically a call center headset and lukewarm coffee.

Schwab dangled a full-time offer, but I wanted something else…so I quit. No offer or good job prospects at graduation. Just vibes.

I graduated that May, spent my last dollars backpacking Europe, and somehow lucked into an interview with JPM from hostel common rooms. Picture me in Budapest, rocking my last clean shirt, begging the Wi-Fi gods to hold up.

I didn’t hear from them for week and I got desperate. At one point, my dad asked me at dinner, “So what’s your plan?” And I actually said: “Well…the guy down the street runs a CutCo operation. I could go door-to-door selling knives until I figure it out.”

I went to the CutCo orientation. Drove to a sketchy office off the highway. Kids were being dropped off by their parents. I sat there pissed off at my life choices and walked out. That same afternoon, JPM called. They were desperate to fill their last analyst slot before training began. I’d bluffed that I had another offer. They bought it.

Later that day, I cried like a baby when the offer came in. Ran upstairs to tell my mom we didn’t have to worry anymore.

Sometimes the “plan” is a bluff that barely works out.

Leap Two: Goodbye $250k/yr Paycheck

I spent five years at JPM. Great title, good money, but I was restless. I felt like I was wasting the prime years of my life building someone else’s dream. So I quit.

This time, I told everyone I landed a flashy venture capital gig. The truth? It was a three-month Techstars contract paying me $6,000 total (less than a single JPM bi-weekly paycheck).

That leap opened a wild door. I landed at Puma Hoops. One minute I was traveling the world, the next I was working nights and weekends with Veera trying to get Habits off the ground. I had a long-distance girlfriend, no free time, and my life was 24/7 chaos.

Still, it felt like I was finally building something of my own. Puma even offered me a full-time Chief of Staff role. I turned it down. Why? Because Habits was starting to show traction. I had $400k in angel commitments. I thought, this is my chance.

Walking away from “safe” is the only way you ever build your own thing.

Leap Three: The Near-Death Stage

And then the market imploded. Banks failed. Angel commitments vanished.

That’s when I made the dumbest—and best—decision of my life: I took my entire JPM nest egg, about $92,000 (basically my last bonus), and injected it into Habits. My financial advisor still gives me sh*t for it. He’s right. There were a million safer options. But I was stubborn, and I wasn’t ready to quit.

Then reality hit. Suddenly, I was in Boston paying $2k rent with maybe $0 coming in. I begged a college buddy to let me crash in his rental in Indianapolis for $600/month. Eventually, I moved back in with my parents.

It was humiliating. I thought I’d blown it completely.

But desperation breeds creativity. With no money and nothing left to lose, I started making TikToks about personal finance. I didn’t overthink it. Just hit record, rambled into my iPhone, and posted.

That was the seed of Habits. Not a boardroom. Not a VC check. Just me at rock bottom, posting into the void.

Sometimes the worst financial move is the only one that keeps the dream alive.

Leap Four: The Content Gamble

Making TikToks turned into something bigger.

Within a year, I’d racked up 5M total views and 15k followers. So I tried Instagram…grew it to 25k. Then I took LinkedIn seriously…just hit 10k this week.

On paper, it sounds clean: 75k+ followers, millions of views, brand partnerships, new users for Habits. Easy, right?

Not even close.

Content is the hardest industry I’ve ever been in. 100x harder than banking. 1,000x harder than I expected. Brutal algorithms. Trolls. Mental gymnastics every time you hit “post.”

But content also made me a mental titan. It brought money, growth, wild opportunities. DMs from comedians I love. Comments from professional athletes. Invitations to events I’d never dream of. Even if my closest friends and family just roast me for being “the TikTok guy.”

Content opened more doors than any single leap before it. And it forced me to show up every day…no excuses, no hiding.

Putting yourself out there is the scariest leap of all. But it changes everything.

The Takeaway

Risk isn’t about being fearless. It’s about moving anyway when you’re broke, scared, and convinced you’re screwing up your life.

Every leap I’ve taken has been messy as hell. But I wasn’t running from something. I was running toward something bigger.

And if there’s one thing I’ve learned, it’s this:

• Believe in yourself when no one else does.

• Bet on yourself even when the odds suck.

• And when the leap is in front of you, take it.

Because your brain will always scream about what could go wrong. Don’t forget to consider what could go right.

The biggest risks don’t just change your career. They change who you are.

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What’s Coming Next?

Next week, I’d like to dive into more about the state of personal finance. It amazes me the sh*t people believe online and the things I overhear at coffee shops or at airports.

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