Hey Founder: Embrace the gift of Bootstrapping

I’ve met plenty of people along the way who wax poetic about the fantasy of being a startup founder. They binge the stories about billionaires who had the big idea, the relentless drive, the oversized vision, and perfect timing. They read like superheroes. But here’s the truth—they aren’t. Some are brilliant, sure. But most fail. More fail than succeed. We all know that, but it doesn’t stop us from chasing the diamond in the rough.

This post is about saying the quiet part out loud from my short journey in startup land. When I talk to successful founders who’ve exited, I hear the same refrain: I wish I had bootstrapped longer. Those who took VC too early almost always regret it. The money was nice, but it came with strings—and mistakes—they wish they could undo.

So here’s the case: bootstrapping your business should be the relentless pursuit at the starting gate. Yes, maybe one day you’ll take outside money. But early on? Do everything you can to avoid it. Because the second the cash flows in, so does the pressure. Suddenly, scaling becomes the religion. But what if waiting just a little longer uncovered the kind of market insight that would help you scale smarter? What if going slower actually gave you more control over how the story unfolded? What if the board member pressuring you to go faster is totally fucking clueless and not worth the money they gave you?

Take it from an accidental bootstrapper: it was the best thing that ever happened.

Let's talk about "The Leap"

Getting your company started is some scary shit!

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Let’s face it—the idea of doing it is often way sexier than the reality. It took me until I was 52 to finally get the guts to do it. Which is funny, because I’ve spent my entire career in innovation. From the first day I set foot in the working world, I’ve been pushing boundaries, changing cultures, evangelizing new ideas, challenging conventional wisdom, envisioning the future, and engaging in innovation as a contact sport as a principle. ]The list of ways I’ve broken shit over the last 30 years in the name of innovation and evangelism is long and unending.

I’ve also innovated at the bottom, the middle, and the top of organizations—big and small—without budget, people, or authority. I always like to say it's easy to innovate when you get to tell a group of 50 people where they need to go because you have authority, it's another thing when you have to influence your way to change with nothing but your skills, abilities and wits as weapons. Essentially, I learned to hack my way forward in every possible direction before I ever "took the leap" into "founderdom".

So why talk about this part of “the leap”? Because the moment you decide to do it, one question will cross your mind immediately: how the fuck am I going to get someone to fund this crazy idea?

And better yet, how the hell are you going to keep the plane flying while you’re still bolting on the wings, the weather is shifting from sunny skies to hailstorms every five minutes, the engines sound like they’re coughing up spare parts, sometimes the whole thing is moving faster than the fuselage can even handle, or worse—you finally get the damn plane built and no one wants to climb aboard your half-finished death trap? It’s like juggling flaming chainsaws while riding a unicycle on a tightrope that’s greased with butter—technically possible, but one slip and you’re toast.

That’s the brutal truth: you have to fund this sucker and constantly push financial death just a little further down the road. And don’t kid yourself—financial death is always waiting around the corner. Here’s a stat I wish I’d known when I started: only 4% of startups ever reach $1M ARR. And a measly 0.4% ever hit $10M.

I don’t share that to scare you off. Taking the leap comes with rewards way beyond getting rich. But the numbers matter, because if you want to avoid financial death, you need a plan, a strategy, and the resilience to keep the plane in the air even when it feels like it might fall apart mid-flight.

So you’ve taken the leap. Now how do you keep from face-planting the second your feet leave the ground?

You’ve got your idea. It feels great. Liberating even. You’re convinced you’re about to drop something new into the world, shake up a market, and disrupt all the dinosaurs who came before you. Awesome. But here’s the rub: you need money. Where do you get it? What do you even need to get it? And, maybe more importantly, what the hell do you actually have at the very beginning that’s worth anyone’s attention?

Here are a few things to get real about before you go sprinting off on the funding path.

Thing 1: Practice your “Grandparent Pitch”

First things first—you’ve gotta be able to explain your idea in five sentences or less. That’s it. If your grandmother or grandfather can’t understand it and repeat back why it matters, you can’t pitch it. End of story.

And no, this isn’t easy. Founders love to believe their genius is obvious to anyone who hears it. But the reality is most ideas sound like gobbledygook if you can’t break them down to the bare bones. Investors will shred you if you can’t do this. Your customers will ignore you. And your team will look at you sideways if you can’t make it simple.

So practice. In the shower, over coffee, when you’re bored in traffic, hell, tell the barista. Keep hacking it down until it’s sharp. Grandparents first. Investors later.

Thing 2: Actually agree on culture principles…right fucking now

Way too many people treat culture like it’s optional. It’s not. Culture is just the way you and your co-founders work together—what you value, how you fight, how you forgive, what you reward, what you absolutely will not tolerate.

So write it down. Don’t overthink it, just get it on paper. “This is how we operate.” That way, when new people join, you can show them what matters to you instead of hoping they magically guess. Because here’s the thing: the mismatch will kill you faster than bad code or clunky sales decks.

We did this, and here’s what happened. The folks who lined up with those cultural principles thrived. The ones who didn’t? They’re gone. No drama, just gone. The earlier you make culture tangible, the easier it is to spot who belongs and who doesn’t.

Thing 3: Talk to some freakin’ customers…a lot of them. Then talk to more.

Brilliant founders think they’re brilliant. They fantasize about the mythical story where someone sketches a pitch on a napkin, shares it mid-jog with a parrot on their shoulder while eating a sandwich, and—bam!—some investor opens their wallet.

Bullshit. Maybe it happens once in a blue moon, but if that’s your plan, you’re delusional. Ideas are like alien assholes—everybody’s got one.

If you don’t know your customer, you don’t have a business. Period. And you don’t get to know your customer by reading TechCrunch or Medium posts. You get to know them by watching them scrub their toilets in Chicago (as I really got to do when I worked at Clorox), asking open-ended questions, shutting the hell up, and listening.

Executives are way easier to get for 45 minutes on an “interview” than on a sales pitch. Use that. Collect stories. Collect frustrations. Collect words that become your bridge between a shiny idea and a real problem worth solving. Don’t trick yourself into thinking you know better. You don’t. You might see better, but until you’ve listened, you’re just making shit up.

Thing 4: Get someone to actually pay you to build it

You’d be shocked how many founders I’ve met who are years in, massively diluted, and still don’t have a single paying customer. They bought into the Valley fairy tale: get VC money, get a sweet valuation, and ride off into the sunset.

Here’s the truth: if you can’t get someone—anyone—to open their wallet to help build your idea, you don’t have a good idea.

So go to your network. Find people who trust you. Pitch them first. Pilot customers don’t just fund you, they validate that what you’re building matters. And they’re not buying from your company yet—they’re buying from you.

And if you can’t sell it, get help. There are plenty of fractional sales leaders who can turn your raw brilliance into a real process. But please, for the love of god, don’t sit around waiting for VC cash before you test whether anyone will pay. That’s how you fail slowly instead of failing fast.

Thing 5: Build a freaking prototype—don’t pitch vaporware

Decks are cute. Prototypes are real. If you can, get a customer to fund it. If not, scrape the cash together. Just make something.

I’ve said for years (and no one loves this line but me): a picture is worth a thousand words, but a demo is worth a million. You can dazzle people with slides all day, but when you put something in their hands—even if it’s duct tape and string—it changes everything.

If your idea is drones, fine, strap a GoPro to a Roomba and make the point. Don’t be the schmuck with vaporware. Make it live, no matter how ugly.

Thing 6: Sure, pitch for money—but mostly to learn why you shouldn’t

We pitched. A lot. Over 100 times. And here’s what I learned: rejection is rocket fuel—but not for pitching more. It’s fuel for building.

Every “no” helps you see where you’re weak, what investors really care about, and—most importantly—who you never want on your board. We figured out exactly the type of investor we did want, not because we got funded, but because bootstrapping forced us to keep pitching with no safety net. Every rejection made us sharper.

Thing 7: Bootstrapping makes you strong

Here’s the dirty secret: a fat bank account makes you dumb.

With $5 million in the bank and two years of runway, you start doing stupid shit. Fancy office. A marketer before you even know if you have product-market fit. A sales leader before you even have a product. Free lunch every day. All waste.

Bootstrapping forces discipline. Every dollar matters because financial death is staring at you every single night. That weight forces precision. You think harder, decide sharper, move faster, and cut cleaner. You don’t have the luxury of time, so you develop the muscle of balancing urgency with caution. It hardens you. It makes you the kind of founder who can actually keep the damn plane in the air while it’s half built.

Too many VC-backed founders are polishing their shiny airplane on the runway, while bootstrappers are already flying rickety but functional contraptions over the ocean. Guess which one actually learns how to fly?

Thing 8: Embrace the happy accidents

When you bootstrap, you don’t have the cash to cover mistakes. That sounds terrifying. But it’s actually a gift.

Happy accidents are the false starts and course corrections that show you where not to go. The sales strategy you thought was perfect until the market laughed in your face. The hire who seemed amazing but crashed and burned. The vertical you thought was gold but turned out to be a dead end.

When money is scarce, you can’t just plow ahead pretending. You’re forced to notice, adjust, and pivot. And those pivots—those little serendipities—are often the reason you eventually land on product-market fit. Bootstrapping doesn’t just make you lean. It makes you lucky.

Thing 9: Angels rule—they’re more valuable than money

Let me be clear: angels are not just walking checkbooks. Good angels are weapons.

They help you sell. They help you pitch. They help you model finances, hire talent, and keep perspective. More than anything—they believe. They’re easier to pitch than VCs, they move faster, and they can literally be the vaccine that keeps financial death from knocking on your door.

Angels are the bridge between pure bootstrapping and scaling. Choose them wisely, because the right angel can be the difference between grinding in the mud and finally catching some altitude.

Thing 10: Do it as long as you can—until the market says you can’t

If you can bootstrap your way to profitability, do it. Total control. No dilution. It’s the dream. But don’t be stupid. If you move too slow, the market will kill you. If you raise too fast, the money will kill you.

This is the paradox: you have to love the bootstrap and hate the bootstrap at the same time. The tension never goes away. It just evolves.

Thing 11: Set a target and hit it

My co-founder was always in the bootstrap camp. Me? I wanted to raise. Guess what—we were both right.

The trick was trusting each other enough to keep the debate alive. We’d set a target, grind toward it, then revisit. And now that we’ve hit the target, the real decision is here.

A happy bootstrapper’s story always walks a frustrating, miserably bumpy road.

This was ours. We ate the dog food we just served up. We practiced the grandparent pitch until even our kids could repeat it back. We wrote down our culture principles before we had a single customer. We sat in rooms, bit our tongues, and listened to customers who knew more than we did. We duct-taped prototypes together. We chased paying customers instead of vanity metrics. We embraced the happy accidents that showed us where not to go. And we found angels—real ones—who weren’t just money but champions who believed when financial death was breathing down our necks.

When we started this company, people told us: “Just slap a deck together, raise a couple of million in pre-seed, and get moving.” We thought, we’ve got a great idea—this should be easy. It wasn’t. In fact, 2023 was the year of ghost VCs—operating and failing at the same time. Valuations tanked. It was safer to put money in a CD than back a startup. Nobody wanted to write a damn check.

So we pitched. We got bupkis. Then we did the things above. We got customers. Financial death came for us. Angels showed up, pushed it back. We grew. More happy accidents. People came and went. Our hypothesis was right but needed constant adjusting. We doubled down, financial death showed up again, and the angels answered again. We added talent, the market spoke louder, and on and on it went.

The point is this: the bootstrap journey isn’t for the faint of heart. It’s for strategic warriors who laugh in the face of financial death, knowing it’s always waiting just around the corner. It’s for founders who are willing to fly a half-built plane through a storm, juggling happy accidents and angel lifelines, while every decision could save you or sink you. It’s hard, it’s scrappy, it’s relentless. But it’s the path that forges real businesses—and real founders.

Go with god. Go with strength. Lace up your boots. Be willing to die with them on.