Dissolving My C-Corp Was Actually a Relief

I filed the paperwork to dissolve Unforced Pickleball, Inc. a few weeks ago. I expected to feel gutted. Instead, I felt something I didn't anticipate: relief.

For years, "company failing" sat at the top of my fear-setting exercise. It was the nightmare scenario, the thing I was supposed to avoid at all costs. Having now lived through it? Far less devastating than I'd imagined. Not painless—but not the catastrophe my anxiety had constructed either.

What follows isn't a humble-brag dressed up as vulnerability. It's an honest accounting of the expensive lessons I learned, the mistakes I'd undo if I could, and why I'm walking away from this experience more equipped than when I started.

Build Painkillers, Not Vitamins

Here's the first truth that cost me dearly to learn: I built a vitamin when I should have been building a painkiller.

The difference matters more than most first-time founders realize. A vitamin is nice to have. It improves things incrementally. People nod along when you describe it. They might even say "that's cool."

A painkiller? People reach for their wallets. They say "take my money" before you've finished your pitch. They're desperate for the solution because the problem is urgent.

I spent months building something people appreciated in theory but didn't need in practice. The enthusiasm was there in conversations, but it evaporated when it came time to actually pay. That gap—between polite interest and genuine demand—is where startups go to die.

If I could go back, I'd be ruthless about this filter: Is this problem so painful that people are actively searching for solutions? Are they already spending money on inferior alternatives? If the answer isn't an emphatic yes, keep looking.

Revenue Before Boats

Businesses cost money. This isn't exactly a revelation, but the implications are easy to underestimate when you're fueled by optimism and a compelling vision.

The conventional startup wisdom says burn the boats. Commit fully. Go all-in.

Here's my counter-take: generate that stream of revenue before you torch the fleet. Even a trickle of paying customers changes everything. It validates your hypothesis with the only metric that matters. It gives you runway that doesn't depend on anyone else's belief in your story. It lets you answer to no one.

Bootstrap. Bootstrap. Bootstrap.

I'm not saying outside capital is always wrong—but the freedom of building something that sustains itself from day one is worth more than most founders appreciate until they've experienced the alternative.

Think Twice (Then Think Again) About Raising Money

Speaking of outside capital: really, really think twice about raising money.

The VC model is built on portfolio math. They're hunting for potential billion-dollar exits because that's how the returns work out. Most investments will fail, so the winners need to be enormous to make the fund's economics work.

This isn't a criticism—it's just the reality of how venture capital functions. But if your trajectory doesn't point toward a massive exit, you're setting yourself up for misaligned incentives. The pressure to grow at all costs, to prioritize scale over sustainability, to make decisions that serve the exit rather than the business—it warps your judgment in ways that are hard to see until you're deep in it.

And friends and family money? That's its own minefield.

Before you take a check from people you care about, ask yourself: Is there obscene growth happening? Do you have genuine conviction—not hope, conviction—that you can not only return their money but grow it?

Trust me on this one. Losing money that belongs to people you love is a specific kind of pain. It strains relationships in ways that are hard to repair. The Thanksgiving table feels different when you're carrying that weight.

Co-Founder Dynamics Will Make or Break You

Equal skin in the game isn't just important—it's essential.

When the curveballs come (and they will), imbalanced dedication strains the relationship in ways that are hard to recover from. If one person is all-in and the other is hedging, that asymmetry creates resentment. It poisons decision-making. It makes hard conversations harder.

The best co-founder relationships I've observed share a few traits: aligned commitment levels, complementary skills, and most importantly—the ability to have brutally honest conversations without the relationship fracturing.

Get this wrong and you're not just risking the business. You're risking friendships, professional reputations, and years of your life spent in a partnership that's working against itself.

Resist the Urge to "Solution"

This one was an expensive lesson in patience.

When you see a problem, the instinct is to jump straight to building. To do something. The energy of creation feels productive. It feels like progress.

But that urge to "solution" often leads you to build the wrong thing, or to build the right thing for the wrong problem, or to build something nobody actually needs.

Time spent up front—validating, questioning, pressure-testing your assumptions—isn't wasted time. It's the most valuable time you can spend. Every hour invested in truly understanding the problem saves weeks of building in the wrong direction.

I wish I'd been more patient. I wish I'd sat with the discomfort of not knowing for longer before I started writing code and burning cash. The validation phase feels slow, but it's nothing compared to the cost of building something that misses the mark.

Walls vs. Mountains

Startup culture loves the "run through walls" mentality. Obstacles are just tests of your commitment. Persistence wins. Never give up.

There's truth in that—to a point.

But here's a question I learned to ask myself: Is this another wall I need to run through, or am I staring at El Capitan?

Hustle culture is real. But so is the data you're gathering every single day. The market feedback. The customer conversations. The numbers that tell a story if you're willing to listen.

Honest reality checks save time and money. Sometimes the most courageous thing isn't pushing harder—it's acknowledging that the evidence points in a direction you don't want to go.

This isn't about giving up at the first sign of resistance. It's about developing the judgment to distinguish between temporary obstacles and fundamental problems with your thesis. That discernment is hard-won, and I'm still learning it. But I know now that ignoring clear signals isn't persistence—it's denial.

The Plot Twist

Here's what surprised me most: closing the company isn't the failure I'd built up in my head.

Yes, the business didn't work. Yes, I made mistakes I'll carry forward. Yes, there's real loss—money, time, opportunity cost, the sting of things not panning out the way I'd hoped.

But failure? That word doesn't quite fit.

What I have now is an education I couldn't have gotten any other way. I understand things about building companies, about myself, about risk and resilience that no book or course could have taught me. The scars are real, but so is the growth.

And honestly? I'm pretty excited about what's next.

Not in a toxic-positivity, "everything happens for a reason" kind of way. More like: I know what to do differently now. I've been pressure-tested. The fears that used to paralyze me have been lived through and survived.

The Value Is in the Scars

If you're reading this and you're in the middle of your own startup struggle, I'm not going to tell you it'll all work out. I don't know if it will. Nobody does.

What I can tell you is this: the value isn't just in the outcome. It's in the scars, the growth, and most importantly—knowing what to do differently next time.

Dissolving my C-corp was actually a relief. Not because I'm glad it's over, but because I'm ready for what comes next. Whatever that turns out to be.

Thanks for reading. If any of this resonated—or if you've got your own hard-won lessons to share—I'd love to hear from you.