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Satire Always Wins

Let’s face it…building a brand on life, career, financial, or any type of serious advice is boring.

People like to laugh! So every few weeks I like to keep my audience on their toes with satirical traps while impersonating an out of touch financial influencer.

You can also watch this on Instagram Reels.

@jack_boudreau_

For the record, it’s a walk up in Williamsburg

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Going from 1 → 10

Earlier this year, I wrote a series about going from 0 to 1. Everyone loves to say that’s the hardest part. And sure, it’s terrifying — because when you’re at zero you don’t know anything. You’re living in constant uncertainty:

• The first time you get ghosted by a prospect.

• The first product bug that shuts everything down.

• The first investor who backs out last minute.

• The first paying user who churns.

• The first re-subscriber that shocks you.

But here’s the thing: 0 → 1 is mostly about courage. Surviving that initial highs and lows of getting something off the ground.

1 → 10? It’s a figure of speech, but a different beast. It’s trench work. It’s saying yes before you’re ready. It’s testing 10 things and keeping the 3 that work. It’s realizing half the job is just surviving long enough to learn.

Here’s what 1 → 10 has looked like for me across sales, users, consumers, content, and product.

Sales: Saying Yes Before You’re Ready

There’s one meeting with Veera I’ll never forget. Big boardroom. Fancy executives. We’re sitting across from them like impostors in a room we barely deserved to be in. They started asking for features that didn’t exist — stuff we had maybe sketched on a whiteboard but were nowhere near completion.

And I said yes.

Veera shot me a look like, “Are you actually doing this right now?” But that’s what 1 → 10 looks like in sales. You say yes first, then figure it out later.

On the rainy Uber ride back, soaked and tired, he asked me, “So… how are we going to pull this off?” I just laughed: “What do you mean? That’s your problem.” (Kidding, but also not.)

That moment sums it up: at this stage, you don’t have a polished sales machine. You just have conviction, some duct tape, and the audacity to commit before you’re ready.

For example, here is a screenshot of our current pipeline. You can see that nearly ever day we have a new firm submitting a request to join.

The best part? We can handpick the ones who come on board.

The better part? Compliance approvals unlock huge referral channels.

The bad part? We’re a team of f**king 6 people. How in the world could we manage ~300+ firms and nearly 1,000 advisors overnight!?

Users: The First L’s That Shape You

Early on, I met a founder who literally laughed at me when I pitched Habits. They had about 120 employees and I figured since many of them had equity comp, that a financial advisor network would be beneficial. He did too, but when he heard me pitch he straight-up laughed.

It felt like a punch in the gut.

But he made solid points. We had no interface for his leadership team to track employee financial wellness, no self service onboarding experience, and at best…a janky mobile prototype that kept crashing.

Which is why we legit call, email, and text every user that comes through. So we can get feedback like this every day.

Consumers: Just Be Human

In Q1, I started hosting weekly cold-call Zooms with our GTM and customer success team. Old-school style: each of us would call users live, and sweat it out in real time.

The core problem was we were hitting record number of users through co-branded landing pages, sign up forms, blog submissions, social media DMs, but too many were falling through the cracks.

One of these sessions, I dialed our highest-net-worth user to date ($40M+) and not even 40 years old. Whole team went silent. He picks up and the first thing he says is, “Pretty sure you’re on my wife’s TikTok algo.”

Without thinking, I shot back: “Wait… do you watch your wife watching TikTok?”

The guy burst out laughing. My team turned red. It wasn’t polished. It wasn’t in a playbook. But it worked because it was human.

That’s 1 → 10 with our users. Not some perfect formula. Just being real enough to connect. We’ve come to recognize that being authentic and being ourselves, is what drives this community forward.

Content: Cringe and Backlash = Progress

Posting online is the most awkward part of my job. It feels cringy. It makes you a target. And when you lean into controversial stuff? You get backlash.

I once posted a video that triggered people so badly I thought I’d ruined my reputation. The comments were brutal. But then the views rolled in. 5 million+ across TikTok and Instagram.

jack_boudreau_

23K followers

View more on Instagram

That’s the tradeoff. If you want content to carry you from 1 → 10, you need thick skin. Because the only thing worse than being hated online is being ignored.

Because when you fight long enough, you finally start to see results. For example, LinkedIn is quickly becoming our #1 source of client acquisition. Last year it was Instagram, and the year before it was TikTok. And these days, they all complement one another.

Product: Welcome to Your Typical Morning

Our product evolution looks clean in hindsight: Squarespace landing page → duct-taped CRM → mobile app → web app → advisor dashboards.

But in reality? It’s chaos. We run three Jira boards, constantly triaging tickets, and arguing about what’s actually a priority.

Here’s a tiny example from this week. I cold-called a user who couldn’t log in. After troubleshooting with him live, we got it working. Ten minutes later, another teammate told me about a young family who’d spent ten minutes stuck in the same loop. Google’s SSO kept telling them they already had an account… except they didn’t.

That’s when it hit us: our login screen was confusing as hell. New users were trying to log in instead of signing up. Which begged the scarier question: how many dozens, hundreds, maybe thousands of people had hit the same wall and just given up?

Welcome to a typical morning at a startup. 1 → 10 in product isn’t clean roadmaps. It’s firefighting, learning from users in real time, and fixing the same issue three different ways before noon.

Closing

Everyone glamorizes 0 → 1 because it makes for a clean origin story. But the real grind is 1 → 10. It’s not one heroic leap — it’s hundreds of messy, uncomfortable, sometimes hilarious steps.

• It’s sitting in boardrooms promising features that don’t exist.

• It’s getting laughed at by founders and learning to sharpen your pitch.

• It’s cold-calling millionaires and accidentally making them laugh.

• It’s posting cringe on the internet until 5 million strangers show up.

• It’s realizing your login screen is confusing as hell and fixing it while wondering how many people you already lost.

That’s the truth of 1 → 10: there is no playbook. Just survive, experiment, and stay human enough that people want to stick around.

10 → 100? That’s a different game. And when I get there, I’ll write about that too.

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What’s Coming Next?

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