^{A note from yours truly…}

You’ve Been Riding With Me. Let’s Take the Next Step.

Real talk: I’m constantly torn between just telling the story and promoting Habits. I never want this blog to feel like a sales funnel but the truth is, if even a fraction of you actually tried Habits, we’d blow past our growth goals and unlock a whole new chapter for this company.

So I’ll keep it simple:
→ Download the app and find out if working with a financial advisor makes sense for you
→ Or book a quick call

You’ve already supported me by reading this far. Now I’m asking you to take one more step.

👇 It takes 90 seconds. And it means the world.

^{Main Story:}

Hiring at a Startup

I’m going to say this in my typical direct and blunt nature…hiring is f**king hard as f**king sh*t. It’s messy, emotional, and personal. So with everything you’re about to read, please take all of this with a heavy grain of salt.

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

Two Guys, One Dream

The day Habits became real was the day Veera joined.

Veera’s my co-founder, my opposite, and my anchor. I’m the people guy with a background in financial advisors and storytelling. He’s the technical and operational brain, the one building the plane while I’m selling tickets mid-air.

For the first 18 months of taking this seriously, it was just the two of us, plus UK Matt (check out his YT page) our first “hire” and unofficial intern who was still in school at the time. And, of course, the dev agency we burned way too much money on.

We had no structure. No product-market fit. No real understanding of what we were building. Just some traction, some referrals, and a relentless desire to help people find financial advisors in a better way.

Don’t start hiring until you and your co-founder (or team or whoever is on this with you) know how you actually complement each other…and what the hell you’re building.

Interns, Agencies, and Dumb F**king Luck

Our first run at product was outsourced. A dev agency we’d used before, run by a friend-of-a-friend. It felt like a smart move… until it wasn’t. The agency didn’t get our vision, and looking back, I’d make the argument we hadn’t earn the right yet to build some sort of robust application.

Enter: UK Matt. Young, hungry, willing to work for free, and referred by someone we trusted. I didn’t give him a job description, and I’m pretty sure I just tossed him the title “research intern” (whatever that means). And I just started throwing random tasks his way. Eventually, he carved out a niche by simply figuring out what we needed.

That became our secret sauce.

For the next 12 months, we did what every scrappy startup does: cobble together 2–3 more people who were willing to roll up their sleeves, take some equity, and build something from nothing. Most of them came in as interns or part-timers and eventually rolled up to full-time hires.

You don't need a recruiter, you need to be damn good at spotting ownership potential in underdogs.

The Shiny Resume Trap

I used to fall hard for the flashy LinkedIn profiles. Early Uber? Early Stripe? Game over. I was sold. Veera, thankfully, wasn’t. He called bullsh*t every time. And every time, he was right.

I was saying yes in my mind too fast. Chasing names and obsessing over what the team slide would look on a pitchdeck instead of evaluating fit. And what we learned, painfully, was that pedigree doesn’t mean sh*t if the person isn’t bought in.

We didn’t have a salary to offer. No brand recognition. Just a decent flow of referrals and a semi-working MVP. But the right people showed up because we were honest about that.

The startup resume isn’t about where you’ve worked, it’s about what you’re willing to work through. Read that again.

Capital Changes the Game, But Not How You Think

We raised our round six months ago. It was a win, but more than anything, it gave us the opportunity to clean things up. We tightened roles. And unfortunately that required us to let a few people go who weren’t a fit anymore.

We also finally had a shot at hiring better because now we had some capital, some traction, and a more compelling story.

And suddenly, the things we used to wing onboarding, performance expectations, internal tools, etc. had to be real. Good teams require vision, structure, accountability, and yes, money. That whole “hire slow, fire fast” saying? It’s true. But only once you know what the hell you’re hiring for.

Capital doesn’t solve hiring…it just removes your excuses for doing it wrong.

Build a Franchise, Not a Family

We still have an evergreen application open, and Veera or I personally meet with anyone who stands out. We don’t rush. We don’t overpromise. We just stay curious.

One of the early Netflix folks said it best: “We’re not a family, we’re a pro sports team.” That’s the hiring philosophy we live by.

Families keep people around no matter what. Sports teams don’t. If you want to win, you need role players, clear responsibilities, high performance, and accountability.

We’re not here to fill seats, we’re building a championship roster.

Treat hiring like building a team that’s trying to win the damn title.

Feedback for Jack

Enjoyed this newsletter? Forward it to a friend and have them signup. Alternatively, use the referral link at the bottom of this email.

What’s Coming Next?

Next week I’m going to try my best to share how life has changed at Habits now that we are a few months out from announcing our raise.

Sharing Is Caring

Do me a favor, if you enjoy this, share it with a friend!