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New Segment Alerttttttt

Shoutout to Stan, a subscriber who called out something obvious in hindsight: most of you found this blog through Instagram, TikTok, LinkedIn, or www.usehabits.com 

But I post different stuff on each platform….some raw, some funny, some viral.

So going forward, I’ll share one post each week that popped off. Think of it as the highlight reel for those who want the good stuff without scrolling.

jack_boudreau_

23K followers

View more on Instagram

^Over the last few weeks I’ve been caught in a satirical phase. Also, I filmed this reel at a coworking space when I met up with a couple blog readers. Shoutout to MJ Ventures!

^{Main Story:}

The Ugly Truth About Scaling

There’s this fairytale version of startups that plays on LinkedIn every damn day. You know the type — “we raised $15M in our first year” or “sold for $80M after nine months.” Cool. Happy for them.

But those are lottery tickets. What no one wants to talk about is the boring, brutal, borderline psychotic reality of what it actually takes to scale.

Because truth is, 0 to 1 is a milestone. It’s exciting. Your first customer. First investor. First press hit. First time your product doesn’t crash.

But that next part — the “now what?” — that’s where most startups quietly bleed out and die a slow death.

The Funnel Starts with Noise, but Survival Is About Signal

Top of funnel. Fancy term for one thing: do people know you exist?

For us, that’s TikTok, Instagram, LinkedIn. That’s content. That’s storytelling. That’s memes and reels and emotionally unhinged carousels. Call it what you want, it’s our lifeline.

We reach millions of people a month now. But look at our backend data and you’ll see the spikes are wild. One week it’s 3M views, the next it’s tumbleweeds. That’s what the top of funnel actually looks like…momentum whiplash. One post away from explosion or obscurity.

And yeah, I could act like we’re geniuses with some scalable, polished “brand flywheel,” but the reality is most of this game is just showing up every f**king day with content that doesn't suck.

Key takeaway: Getting attention is hard. Keeping it is harder. Converting it is art.

Middle of Funnel = Where Startups Go to Die

This part is where shit gets real. Everyone talks about growth, but nobody talks about how gross it is.

Our early CRM was just a graveyard of Google Sheets, half-finished Airtables, a Zoho trial we never used, and a bunch of inboxes filled with “Hey, just following up...” It worked…until it didn’t.

So we built structure. Actual lifecycle stages. Here’s how we break it down now:

• Identified: You popped up. Maybe you booked a call, ghosted us, saw us at a conference, or filled out a form through your employer. You’re on the map, but that’s it.

• Aware (MQL): You opted in. Gave us your info. Downloaded the app but didn’t finish onboarding. You're interested, but not committed. You're circling the pool, but haven’t jumped in.

• Interested (SQL): You’ve met with one or more advisors. You’re engaged. You're poking around the product. You're in the damn building.

• Evaluating: You told us you're choosing. You’re asking questions, talking to your spouse, checking your budget. We probably know you by name. And we’re holding our breath.

• Customer / Evangelist: Either you found your advisor — or you didn’t, but still believe in the mission. You refer your friends. Your HR team. You text us like we’re your unpaid therapist. You get it.

We run about 500-ish SQLs a month now. These are people who are in the thick of it. They need a nudge, a text, a well-timed GIF — something to keep them from slipping out the back door.

But as volume grows, so does the chaos. And this is where most startups drown. They never make the jump from “we have users” to “we know what to do with them.”

Key takeaway: Most founders can get someone in the door. Very few know how to keep them from wandering back out.

Scaling Feels Like Doing the Same Thing…Just Way, Way Faster

Let me explain something people don’t understand about GTM: it’s not one big breakthrough. It’s a thousand little repetitions. It’s getting someone to say yes, and then doing it again. Then again. And again. Faster. Cleaner. Louder. Cheaper.

At first, one advisor joins every few months. Cool. Then it's one a month. Then every week. Then every day. Then it's: “Why didn’t three sign up before lunch?”

The wins don’t change. Just the speed and the pressure.

And this f**king sucks if you don’t have a machine. Because now it’s not just marketing and product — it’s coordination. Ops. Data. Customer success. You have to build an engine while it’s already running at 6,000 RPM.

Fixing a bike is one thing. Fixing a commercial airliner at cruising altitude is another. That’s the difference between 0 to 1... and scale.

Key takeaway: It’s not the reps that get you. It’s the pace. Growth demands rhythm or it’ll chew you up.

The Goal Is Not “Hype.” It’s Surviving Long Enough to Find Your “Aha.”

Everyone wants a shortcut. But here’s the cold truth: Uber? Founded in 2009. Airbnb? 2008. OpenAI? 2015. Stripe? 2011. None of this happened fast.

You know what all those companies have in common? They lasted.

They didn’t just ride a viral moment. They made it through the quiet years. The “is this working?” years. The awkward pivots, dead experiments, and shitty dashboards.

Startups don’t die because the product sucks. They die because the team runs out of gas before they find the thing that clicks.

At Habits, I think we’re finding it. Every dollar we put in feels like it generates $10 of value. We’re getting smarter. More surgical. More repeatable. We know how to talk to our audience. When. Where. With what message. What features to build. What to ignore.

But it took years of guessing, reworking, and testing in real-time. You don’t get to skip that. Not if you want to build something that actually matters.

Key takeaway: Survive long enough to earn your “aha” moment — and everything changes.

Final Thoughts

The thing about go-to-market is it sounds like a department. A strategy. A process.

But for founders, it’s the whole f**king job.

You're the marketer. The closer. The therapist. The janitor. The air traffic controller. And if you don’t obsess over this stuff, someone else will — and they’ll win.

I thrive in this chaos. Because this is where things get interesting. It’s where growth gets real. And yeah, it’s hard. It’s humbling. It breaks you down and forces you to level up in ways you didn’t know you had in you.

But if you keep pushing? If you keep solving and building and surviving?

You get to watch the engine roar.

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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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