^{Sponsorship opportunity}

Sponsors? Possibly You!

I’ve done a bunch of brand deals on Instagram and TikTok—and now a few of those brands are sliding into this blog too. So here’s the deal:

• If you’re an early-stage startup with no marketing budget? Cool. I’ve been there. Hit me up.

• If you’ve got a brand with sick shoes, socks, or coffee? Send a sample. I’ll wear it, sip it, and if it slaps, I’ll shout it out.

• If you’re a brand with a massive marketing budget? DMs are opennnnn.

Or if you just happen to own a cozy B&B / short-term rental in Portland, Maine and want a shoutout in exchange for a memorable stay this July… I’m listening.

But seriously, if you’re building something cool, and think it’d vibe with this audience of scrappy founders, curious readers, Habits enthusiasts, and finance focused zillennials, let’s make some noise together.

^{www.usehabits.com}

Want to know your options?

I’ve met and spoken with a dozen users in the past week at Habits.

Whether you want a financial advisor or not, the beautiful part about our marketplace is figuring out your options. Answering questions like…

• At what age does it make sense to work with a financial advisor?

• What if I just want a quick, TL;DR review of my finances?

• Where do I rank amongst my peer group(s)?

• What does a financial advisor cost?

So I’ll keep it simple:
→ Download the app 
→ Or book a quick call

^{Main Story:}

6 Months Post-Raise

I’m writing today’s blog from the office of our lead investor, Atlanta Ventures. Literally, I’m posted next to a few of the partners, probably taking someones standing desk, and genuinely trying to digest what has actually changed for Habits post-raise.

This is not a playbook, but what worked for us.

If You’re New Here…

Habits started as a scrappy little LLC registered in Indiana (or maybe Illinois? honestly, who knows) back in June 2022.

At some point, I blinked and we had a few employees, about 20 advisory firms on board, and 30–50 people every month reaching out for help finding a financial advisor.

To fund the growth, we strung together a few SAFE notes $5K here, $25K there. Just enough to keep the wheels turning. I didn’t start paying myself until July of last year.

Eventually, we got two VCs to take a bet on us, and in November 2024, we closed a priced round led by Atlanta Ventures. We announced it on stage after winning a pitch competition in Chicago…competing against 46 insanely impressive fintech startups from around the world. Still feels surreal.

TL;DR — I know what it’s like where shit breaks if someone pays on the 29th instead of the 5th. And if you don’t get that joke…it’s probably because you’ve never been that close to the edge.

Bootstrapping: Stress and $1,000 Credit Card Charges

For two years, I bootstrapped Habits while working a full-time job. Nights, weekends, whatever it took. At one point, I was pitching financial advisors, families, and VCs from a friend’s brother’s mattress, typing on a standing desk I bought for $100 off Amazon.

I remember the stress of pulling out my personal credit card to file our Delaware C-Corp. That $1,000 felt like I was setting my life on fire. And now? I’ll spend $1,000 on travel for a $50k sales meeting and still flinch the same way.

That’s not because I hate spending money. It’s because bootstrapping scars you in a way most people don’t talk about. There’s this constant mental trauma loop…every decision feels like it might kill your company. Every delay, every hiccup, every “hey just checking in” Slack from a team member you’re paying out of pocket feels like another punch in the mouth. And you just keep getting back up.

What’s worse is the constant internal voice: Am I wasting other people’s time? 

That’s the one that eats at you. Because once people start believing in what you’re building, the stakes multiply. Now it’s not just your time on the line. It’s theirs too.

Raising a Round: You're Suddenly a “Success”

When we raised our first round, led by Atlanta Ventures, everything changed. And nothing did.

The weirdest part? People started texting me. Competitors, VCs, people I hadn’t heard from in years: “Congrats, man!” Suddenly, we were legit. We were in the club.

But here’s the part no one prepares you for: raising money doesn’t give you peace. It just gives you options. And those options come with new pressure.

The second we closed that round, the game changed. Now we had to go faster. Think bigger. Execute cleaner. Our old worries (like whether an advisor paid on the 29th vs. the 3rd and if it would screw up payroll) got replaced with new ones: Are we building the right features? Are we hiring fast enough? Are we spending wisely? Is the burn worth the bet?

VC money is like a steroid shot. You either grow fast and strong or tear yourself apart trying. There’s no in-between.

Seedstrapping: The New Game

That’s where this idea of seedstrapping comes in. You’re still scrappy, still moving fast, still wearing eight hats, but now you’ve got some capital in the bank and a couple legit investors watching. You’re no longer just building a product. You’re building a company. Real processes. Real headcount. Real expectations.

It’s like going from pickup basketball to the G-League. You’re still hustling, but now people are watching your stats.

And don’t get me wrong raising gave us breathing room. We finally had time to think strategically instead of just trying to survive the week. We got to hire. Build. Plan. Dream a little.

But the founder mindset? That didn’t change. I still wake up wondering if we’re doing enough. If I’m letting people down. If I’m burning too slow or too fast. If I’ve earned the right to be here…

So... What Did Change?

Someone asked me recently, “What changed after you raised?”

I didn’t have a great answer in the moment. But the best way I can put it is this:

We unlocked optionality.

We now get to solve problems with time or money. That’s a gift, but it’s also a trap. Because the more money you have, the more tempting it is to try and shortcut your way through stuff you should still be doing the hard way. Like talking to users. Making sh*t yourself. Staying uncomfortably close to the chaos.

The stakes are higher now. That’s the real difference.

Before, it was survival. Now, it’s acceleration.

Before, it was “can we make this work?” Now, it’s “can we make this scale?”

Funny enough, what took four years to cobble together with duct tape and optimism might now take 3–6 months. That’s not because we got smarter. It’s because we finally learned what not to waste time on.

Final Thoughts: You're Not Crazy

If you’re in the thick of it right now, bootstrapped, overworked, wondering if you’re delusional, just know this: you’re not crazy. You’re doing the hardest job there is. Convincing other people (and yourself) that something nobody asked for deserves to exist.

Whether you’re raising, thinking about raising, or committed to never taking a dollar…there’s no right path. There’s just your path. And it’s probably going to be ugly, unpredictable, and weird as hell. Embrace that.

Oh, and one last thing: get a co-founder. Trust me. You don’t want to do this shit alone.

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What’s Coming Next?

I recognize this emotional rant was more geared towards founders, but next week is going to be all about corporate life vs. “working for yourself.” I graduated 8 years ago, and spent about half the time in corporate and the other half in no man’s land.

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