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State of the Union

The post below took off, not just because it was funny, but because it’s real.

Let’s be honest: a lot of people are scared right now. About money, jobs, mortgage/rent, the world. Humor’s one of the few universal truths which was the inspiration behind this post.

You can also watch it on TikTok.

jack_boudreau_

25K followers

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The Gift of Being Underestimated

Everybody loves to hop on a bandwagon. Momentum attracts cheerleaders. Progress attracts praise.

But before all that, there’s a long stretch of silence…when nobody gives a damn who you are or what you’re building. That’s the real gift of being underestimated.
When nobody’s watching, you learn to crawl, scrape, and claw your way forward. You stop chasing applause and start chasing proof.

And the hardest lesson of all? Enough is never enough. No matter what number you show, someone will say it isn’t big enough, fast enough, or good enough. So you stop building for approval and start building for conviction.

1. The Ones Who Believe Early

A big chunk of 2023 and 2024 was pure scrappiness. We pitched advisors using Figma mockups and half-built workflows. We barely had a product, just conviction and charm.

The truth? Most advisors were skeptical. And rightfully so. But the families or individuals we came across, they’re the ones who kept us alive.

Talking to them has been and will always be my favorite part of this whole journey. These people get it. They want better lives, better systems, better guidance. And when they find something that works, they’ll move heaven and earth to help you.

We’ve done over 3,000 one-on-one calls with users. And no matter how tired I am, if I talk to even one person who says, “You helped me finally understand this stuff,” it reignites everything.

When we won the People’s Choice Award at 1871 earlier this year, it wasn’t a huge payday or a big contract. It was something better, hundreds of real people choosing to root for us.

It reminded me why we started: most people don’t root for you until everyone else does. But those who do? They’re the foundation that keeps you from collapsing.

You don’t need everyone to believe, you just need a few who really do.

2. The Bandwagon Effect

I’ll never forget the first time we pitched investors in person. Veera and I were at this event in Indianapolis, basically investor speed dating. Ten meetings. Twenty minutes each. Ten minutes to pitch, ten minutes for Q&A.

We sat down with a fund that bragged about being “first check in.” On their website, it said they like to see $50,000 in monthly recurring revenue. We had…a landing page, a contact form, and a handful of TikTok videos and nowhere near that revenue mark.

Within five minutes, their associates were openly dismissive. Picking apart every word, smirking through our pitch. I get it, there was a lot to sh*t on back then. But the worst part? Five minutes later, I 100% saw one of them openly laughing about us across the room.

Eighteen months later, that same associate followed me on TikTok. Three months after that, his MD emailed Veera and me asking for a meeting.

We took it. Played it cool. Pretended like we didn’t remember. And it was wild watching how their tone shifted, suddenly we were “impressive,” “interesting,” “a company to watch.”

That’s when it really hit me: nobody cares about ambition. They care about momentum. People love being the last one on the bandwagon because when the bus finally pulls into the station, they get treated like they’ve been there since day one.

Being underestimated is a gift. It forces you to build something worth believing in.

3. The Chaos of Being Seen

Creating content is its own kind of war. The human brain wasn’t built to absorb 10,000 opinions about you in a day.

I’ve made my fair share of controversial posts…satire, comedy, finance jokes, startup rants, all of it. I’ve also gotten DMs that made me physically sick. I used to spend hours on a single post. Now I spend maybe 30 minutes. Because as long as I lead with good intentions, I can sleep fine.

A friend of mine with 500k followers once said, “Instagram and TikTok aren’t social media anymore. They’re dopamine casinos.” He’s right. It’s quick, volatile, and brutal.

But here’s the thing: being underestimated online builds resilience offline.
When people misread you, doubt you, or mock you and you still show up the next day, that’s your edge. That’s your moat.

Because when the algorithm stops caring, the people who’ve been quietly rooting for you are still there.

If you can handle being misunderstood, you can handle almost anything.

4. The Long Game

I’ve spent the last two years splitting time between Indianapolis, Chicago, Boston, New York, Houston, and a bunch of one off stay’s for a month at a time.

I’d take Zoom calls from random parks, answer DMs on planes, and pitch investors while sitting in rental cars. I’ve literally lost deals mid-sentence because I drove through a dead zone in West Virginia or Pennsylvania.

But that’s the grind. You sell, you get rejected, you repeat. And slowly, people start to pay attention.

Now, as we open our office, rebrand the company (stay tuned), and build the next phase of Habits, I remind myself every day that this is the point. Being underestimated is freedom. It’s space to build without noise.

When nobody’s watching, you get to define what “enough” actually means.

Being underestimated is the greatest advantage you’ll ever have, if you know how to use it.

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