Let’s Get Tropical Vulnerable

This is the final blog in my “getting personal” series, and trust me—I saved the best for last. This is where I get raw and honest about the biggest risks I’ve taken in life and why sometimes, you just have to bet on yourself.

(And I’ll share what’s coming next for this blog at the end)

The video below is a great example. And in < 24hrs had over 125k+ views.

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1871 Winning Pitch - Video

Last week I shared the presentation, this week I’m sharing my entire pitch from start to finish!

Use code “HABITS” to access our #1 voted pitch out of 46 globally distributed fintech startups.

My Life in Three Leaps

Risk-taking gets dressed up as some heroic act in business books and TED Talks. But the truth? It’s messy, f**king terrifying, and usually means lying awake at night wondering if you just made the biggest mistake of your life.

I should know—I’ve made taking risks my entire personality. Here are three of my biggest leaps, the ones that had me questioning my sanity but ultimately got me here.

Story #1: Leaving Schwab With No Plan

In 2017, I was working a decent gig at Charles Schwab about 20hrs a week during my senior year at Butler University. Call center life wasn’t glamorous, but they dangled a decent opportunity in front of me, and everyone thought I’d be stupid to walk away. But here’s the thing: my dream wasn’t to climb the Schwab ladder. I wanted to be in a big bank analyst training program, the kind of thing that sets your career to the moon (at least in my eyes at the time).

So, I left in April—no job offers, just vibes—and graduated college in May. Then, because I clearly hate stability, I took my last few bucks and went backpacking in Europe with my friends. While they were sightseeing and drinking cheap wine, I was interviewing for a role in the JPM analyst program. I did virtual interviews in hostel common rooms, dodging travelers, rocking my last clean shirt, and hoping the Wi-Fi held up. My final interview? No tie, no shave, no dignity—just desperation while in Budapest.

(And remember, this is all wayyyy before ZOOM or WFH was even a thing)

When I got back to the U.S., I still didn’t have an answer. So I pulled out my biggest bluff: I told JPM I had another offer (I didn’t) and said, “But this is the job I want.” I was so desperate that earlier that day, I sat through a CutCo orientation session trying to figure out if selling knives was my future.

When the JPM offer came through, I cried like a baby. I ran upstairs to my mom, bawling, and told her we didn’t have to worry anymore. Risk one: survived.

Story Two: Leaving JPM For A Lie

A few years later, I had what most people would call a dream job at JPM. But I was restless. I told everyone I was leaving for a flashy venture capital gig because, well, it sounded cooler than the truth: I’d accepted a three-month contract with zero guarantee of what came next. I was betting on myself, but damn, it was a risky bet.

That gamble paid off, though. By some miracle, I landed a role at Puma Hoops, and let me tell you, it was everything 22-year-old me could’ve dreamed of. I was traveling the world, working with NBA athletes, and building connections with influencers. But as great as it was, my dream wasn’t to work for Puma—it was to build something of my own.

So, when Puma offered me a full-time role - to essentially become the Puma Hoops Chief of Staff, I said no. I thought I had everything lined up: Habits was just starting to gain traction, and I was riding high on $400K in angel commitments. I figured, “Why not? This is the leap.”

Story Three: The Leap That Almost Killed Me

And then the market imploded. Banks started failing, the commitments dried up, and I found myself in a panic. My rent in Boston was nearly 2k a month and saw the future of having $0 in the bank. I ended up calling one of my college buddies and begging him to let me live in his Indianapolis-based rental property for $600 a month because it was all I could afford.

It got worse. Money got so tight that I moved back in with my parents. For a while, I felt like I had failed completely. But desperation does something to you—it makes you creative. Broke and terrified, I started making TikToks about personal finance. I didn’t overthink it; I just hit record and talked.

That’s how Habits began. Not with a boardroom or a big check, but with me, a smartphone, and the willingness to try something—anything—to make it work.

The Takeaway: Run Toward It

Here’s the thing about risk: it’s not about being fearless. It’s about having the guts to keep moving forward even when everything feels like it’s falling apart. Every leap I’ve taken has been terrifying, but I didn’t do it because I wanted to escape something. I did it because I was running toward something bigger.

If there’s one lesson I’ve learned, it’s this: believe in yourself, even when no one else does. Bet on yourself, even when the odds feel impossible. And don’t be afraid to take the leap—you never know where it might land you.

Let this be a friendly reminder that our brains may force us to consider what could go wrong, but don’t forget to consider what could go right…

What’s Coming Next?

My next few blogs will focus on 0-1, bootstrapping, getting our first angel check and all things before our followers, raise, and customer base.

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