^{Training the Street}

Training the Street

The most overlooked skill: self-teaching.

It’s the #1 required skill for any Wall Street job, and I’d argue the same for founders or business owners.

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They’ve got you covered with:

A full Investment Banking Bundle, discounted 25% off for my readers (code: HABITS_25)

If you’re serious about leveling up or breaking in → Training The Street is where the pros go to prep.

^{Big Announcement!!!}

“Best In Show” Winner

I’m happy to announce that last night, Habits was awarded “Best In Show” out of 12 incredible FinTech startups at Morningstar’s Investor Conference.

Let’s break it down below 👇️ 

^{Main Story:}

How We Landed "Best in Show" at Morningstar While Still Building the Damn Plane

It’s 11:50pm. I’ve had a couple drinks, been on the road for 10 days, and am sitting on the edge of a bed trying to type this before my brain gives out. I don’t know if this is a blog post, a voice memo to the universe, or just a little journal entry to remember what today felt like.

But I think it’s important to write this down while it’s still fresh. Because today was one of those rare days in startup land where something clicked. Where the universe cracked open and said, “Hey. You’re on the right path. Keep going.”

Let me explain.

The Full-Circle Moment

Three years ago, I was wrapping up a short-term contract with Techstars, working on what would eventually become Habits. I was broke, mostly alone, and legit begging people to take my calls. Cold emails, cold DMs, warm intros that ghosted. All of it.

Fast forward to today: Habits just won “Best in Show” at Morningstar’s Global Investor Conference. Not a local pitch night. Not a fintech mixer in someone’s office basement. Morningstar. One of the most respected, globally recognized names in the financial space.

Let that sink in. Former presenting companies include M1 Finance. Altruist. Acorns. Advisor360. Halo. AssetMap. Absolute beasts in our space.

Just being in the room is a win.

Some milestones aren’t about the money—they’re about the moment.

The Butterfly Effect: From Cafeteria to Conference Stage

Funny thing is, the reason we even got nominated was because of a cafeteria meeting. Habits had just joined the 1871 Fintech Lab last fall. One day, we toured Morningstar’s HQ, and I pitched two execs over lunch. Backpack on. Laptop open. No deck. Just vibes.

We didn’t hear from them for weeks. Then we won 1871’s Fintech Pitch Competition (out of 46 companies), sent the recap their way, and suddenly we got a reply: “We want you back in Chicago. You’re pitching at Morningstar this June.”

It wasn’t magic. It wasn’t a warm intro from some VC. It was a chain reaction of small moments: show up, give a shit, and follow up.

Momentum comes from moments that don’t feel big…until they are.

Startups Have No Deadlines (So You Have to Make Them)

Here’s the thing no one tells you: startups don’t come with built-in urgency. Customers buy when they feel like it. VCs invest when the narrative feels right. Engineers ship when the thing works. So how do you create urgency?

Events like Morningstar. Big public milestones. Artificial pressure. We told our team: this is the date. We’re launching the new web app. We’re unveiling the new site. We’re shipping the mobile update. Period.

Because otherwise? Everything slips.

This conference gave our entire company a reason to sprint. It gave us something to look forward to and to rally around. It also gave us a way to speak with urgency to users (“book now before we’re booked up”), investors (“we’re not raising right now, we’re laser focused on this”), and advisors (“lock in this rate before Morningstar pricing hits”).

Deadlines are fake. Momentum is real. Use the fake ones to get the real one.

5,000 People. 3 Football Fields. Oh Sh*t, We’re Here.

Walking into the Morningstar Conference hit me like a truck. The scale? Unreal.

Three football fields of booths, most of which probably cost $100K+. A sea of financial advisors, investors, execs, and media. For a second, I froze. Like, damn… we’re really here.

I met up with Veera, my co-founder. We talked to our Morningstar sponsor, who helped nominate us. Then snuck into a side room to rehearse the pitch one last time.

People think I don’t get nervous before speaking. I do, it just doesn’t come from the crowd. It comes from who I represent. I think about Matt, who’s been with us for two years. Buddy, our engineering lead. Brandon, who started as an intern and is now becoming a pillar on the team. Juan, Sakthi, Frank….all the devs who deal with our chaos and still manage to ship.

And I think about Veera. The guy who sets up our meetings. Who knows every sponsor, every booth, every face. He lives for this conference stuff. I’m the on-stage guy. He’s the get-shit-done guy.

So yeah, I rehearse. I step away. I try to tune everything out so I can remember: this is for them.

The best speeches aren’t about the speaker → they’re about the people behind the scenes.

The Pitch, the Crowd, and the Polls

Our pitch? Five minutes. Snappy. Honest. Zero buzzwords. We did our Q&A. Watched the other 11 startups do their thing. And man… what a group. These weren’t noobs. These were sharp operators with real traction.

Two awards were up for grabs: one from the judges, one from the crowd.

Let me be real: I didn’t care about the judges. I cared about the people.

Because Habits is built for the people. The DIY-ers. The anxious budgeters. The couples trying to figure it out. The 31-year-old with a new baby and a ton of questions. I am our target customer. Our whole strategy is to be relatable, useful, and real. Not institutional.

Build for the people. Speak to the people. Win with the people.

Best in Show, Announced via… Bar Gossip?

After the pitch, we went to go see the CEOs of Morningstar, Vanguard, and Dodge & Cox talk shop. Titans of finance. Heavy-hitters.

They finished their speeches, hopped on their private jets, and left. Veera and I? We grabbed some food and accidentally showed up late to the closing happy hour. We had no idea they’d closed the polls and everyone knew we had won Best in Show prior to our arrival.

People started congratulating us the moment we walked in. At first we were like, “Thanks, appreciate it.” But then a Morningstar employee pulled us aside and said, “Check the polls. It should be bolded in black by now. Y’all won.”

Best in Show.

We missed the actual announcement. But honestly? It made the whole thing even more perfect. We weren’t there for the photo op. We were there to do the damn work. And it turns out, the work was enough.

If you show up and give a shit, people notice. Even if you’re late to the party.

It’s Not the Award. It’s What Comes Next.

Let me be super clear: this isn’t about a plaque. Morningstar’s not cutting us a check. We’re not getting acquired next week. We’re still on the same grind we were on last month.

But now? The story’s different. The doors feel a little more open. The meetings come a little easier. The next conversation might start with, “Hey, saw you guys won Morningstar.”

And that’s the whole game in startups. You collect little story fragments and stack them into something that earns trust.

The story doesn’t sell the product. But it opens the door.

Celebrate It. Then Get Back to Work.

I’m flying to Vegas tomorrow. Witnessing my first-ever UFC fight on Saturday as we celebrate a friend of mine who I’ve known for over 25 years. I’m exhausted. I’m happy. And I’m so, so ready to go home.

But come Monday? We get back to work. We keep building. Keep fixing bugs. Keep onboarding users. Keep telling this wild story we’ve been lucky enough to live.

Thanks for being along for the ride. More to come.

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What’s Coming Next?

tbh i’m so exhausted right now, and can’t even think about next week’s blog. So have a good rest of the week and see your inbox next Thursday.

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