^{Shameful Plug}

Let’s skip the awkward money convos…

What you are going through isn’t simple. That’s why we built Habits differently.

• ❌ We don't sell your data

• ❌ You won’t get spammed by 10 salesy advisors

• ✅ You stay anonymous

• ✅ First call is always free

• ✅ You only talk to advisors if you want to

• ✅ We accept <1% of advisors who apply

We’ve helped thousands of people, many of whom didn’t think they were “ready." You don’t need to have it all figured out. You just need a place to start.

Alternatively, you can reply directly to this email, visit our website or download our mobile app (iOS or Android)!

No pressure, just options.

^{Main Story:}

How We Got Lucky: 4 Random, Ridiculous, and Totally Engineered Breaks That Built Habits

Early on in my founder journey, I did what every wannabe entrepreneur does: I binged Y Combinator’s Startup School on YouTube. In one of those episodes, Gary Tan said something that cemented itself onto my brain: “A founder’s job is to maximize their chance to get lucky.”

He followed it up with a bunch of stories (wild ones) of founders who “just happened” to be in the right place at the right time. But if you listen closely, none of them were sitting around waiting. They were getting eyes on their product, on their problem, on themselves.

I’d argue the same for us. At Habits, we’ve been incredibly lucky. But it wasn’t magic. We engineered it. We stayed in the game long enough to get the bounce.

Here are the four moments where we “got lucky”and how we did the unglamorous work that made those moments possible.

1. The Venti Cold Brew Office and the JPMorgan Launchpad

From the outside, I looked like I had it figured out (back in 2017)…I got a full-time JPMorgan analyst offer right out of college. But what people don’t know is that I failed 30+ superdays over junior and senior year. I turned “getting a job” into a full-time job. While most of my classmates were gunning for 4.0s, I made a bet: the difference between a 3.5 and a 4.0 GPA wasn’t worth missing out on the real world.

So I camped out in the Butler University Starbucks, bought one venti cold brew (never drank it, always looked fresh), and set up shop. I’d book back-to-back coffee chats with analysts, alumni, random strangers on LinkedIn literally anyone who’d talk to me. Half of it went nowhere. But then, things started clicking.

In my last semester, I participated in the CFA Research Challenge with two undergrad buddies. We beat out grad programs like Notre Dame, IU, and University of Louisville, won the Midwest, and got flown to Seattle for the global finals. It didn’t get me an offer right away, but two months later, I got the JPM call. Throughout my banking career, I learned how to talk to CEOs, cold call founders, execute under pressure, and (most importantly) save like hell. By 25, I had close to $400K to my name, which eventually gave me the cushion to quit and take a swing at Habits.

Luck favors the obsessive. No one sees the years you spend working late nights or weekends in silence until the door opens.

2. A Random Techstars Call, Couch-Surfing, and Veera

After JPM, I did what a lot of people do…I tried to break into VC. I applied to nearly 50 gigs, networked with dozens of people, and landed a contract role with Techstars. That only happened because they called me while I was literally twiddling my thumbs waiting for another Zoom to start. Right place, right time—but also, I answered the phone.

Techstars became my MBA. I soaked up everything: how angel investors think, what separates real startups from fluff, how capital actually works. But the bigger win? I met Veera, my now co-founder.

It was so random. I messaged a Techstars CTO through their internal directory. He happened to go to high school with Veera. And Veera had just left his job. Our mutual friend warned me: “He’s probably not going to go full-time because his typical salary is between $350k+/yr.” But we started chatting anyway. And met up about a month after I just had moved to Boston. It took time to figure out how to work together, but over the years we’ve built one of the most honest, intense, complementary partnerships I could’ve asked for. That connection came from a single message thread. Butterfly effect.

And Boston? Total cheat code for early-stage founders. It’s got a great startup community. The perfect combo of size, talent, competitivesness, and willingness to help others. Candidly, I only moved there because a former soccer teammate needed a roommate, and just so happened to share that on his Instagram story, the very day I got offered a new contract position out there. Butterfly effect x 2.

The best co-founder is probably three introductions away, you just have to give the universe enough swings.

3. TikTok, Content, and the “Minimal Viable Personal Brand”

In early 2023, Habits was in scramble mode. Bank collapses had wiped out the capital we thought we were going to raise. I was couch-surfing, half-digital nomad, half-desperate founder. I told my girlfriend daily that Habits might die.

So I pivoted to TikTok. I started posting. For 30+ days, nothing happened…ghost town. Then a video hit 500K views. I didn’t sleep. That moment was all I needed to go all-in.

@jack_boudreau_

#stitch with @wallstreetoasis “That’s not a recommendation. It’s a prescription” #timemanagement #investmentbanking #w... See more

That one post sparked everything: growth, users, investor interest. And it wasn’t just TikTok —> Reels, LinkedIn, you name it. We built what I now call a “Minimal Viable Personal Brand.” Turns out, people want to hear from real founders, not just glossy logos. And VCs have started paying attention to that too. I’ve heard from other founders that some VCs now evaluate companies on their organic reach and narrative control.

Our content has closed investors, converted users, hired team members, and created social proof from nothing.

The algorithm is a roulette wheel, but you can spin it every damn day until it hits.

4. Chicago, 1871, and the Fintech Snowball

In 2024, I moved back to Chicago. We got into 1871’s accelerator program, right place, right city, right network. The cohort was stacked with great startups, and during the FinTech Innovation Lab Summit, we won the People’s Choice Award.

That win kicked off a tidal wave: we closed a round, got introduced to major enterprise customers, and even found ourselves inside the Morningstar conference by total accident (long story). We weren’t scheming, it was just the result of showing up, putting our name out there, saying yes to the weird events, and taking the meetings most people ignore.

The story behind every big break has a dozen micro-moments like that…unsexy, tiny advantages that add up to a head start.

Luck compounds the more you show up; the more doors you knock on, the more open up.

The Luck Formula (That Isn’t Luck at All)

People say “you just got lucky.” And I say: hell yeah, but luck doesn’t chase people who sit still. Everything good that’s happened with Habits came from us manufacturing surface area—putting ourselves in situations where something could happen.

Want to get lucky?

1. Network like you will run out of cash tomorrow.

2. Insert yourself into ecosystems that scare you.

3. Ship content until the algorithm blushes.

4. Keep moving—geographically, emotionally, and mentally.

You do this long enough, and eventually, people start calling you an overnight success. Smile. Nod. Get back to work.

Because luck isn’t lightning, it’s friction. And founders? We’re the match.

(sorry for the corny ending…couldn’t resist)

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