Hello {{First name|Predictable Revenue community}},

VClist update: I have built out the golden path that everyone asked in the last feedback call. “Find me relevant investors that are still active” then “show me who can introduce me to them”. If you want to be an early alpha tester, I’m hosting a feedback call at 230pm PT today. Come give me some feedback and your first list is on the house. Hit reply if you want to join.

Onto the newsletter…

I should have shut it down in 2017.

That's not hindsight talking. I knew it then. Somewhere in my gut, I knew Carb.io wasn't going to become the thing we wanted it to be. The product wasn't getting traction. The market wasn't responding the way we needed. The signs were all there.

But I didn't shut it down. I didn't try to sell it. I didn't do any of the rational, strategic things a founder is supposed to do when a product isn't working. Instead, I just kept going.

Not because I had a plan. Because I was scared.

Here's the thing. I wasn't afraid of failure. I could handle saying "that didn't work." I'd been through enough by that point to know that failure is just part of the game.

What terrified me was the idea that I might not be an entrepreneur anymore.

That sounds dramatic, but if you've been in it, you know what I mean. There's this identity you build around yourself. You're the person who's building something. You're in the arena. You have a company, a product, a vision. You wake up every day with a purpose that feels different from having a job.

I was afraid that if I shut down Carb.io, if I found the natural conclusion of that chapter, I'd lose the momentum. And momentum, once lost, felt impossible to get back.

So I held on. I convinced myself that the next iteration would work, that we just needed to pivot one more time, that the services side of Predictable Revenue would carry us while we figured it out. And technically, it did carry us. The consulting and outsourced sales development business kept the lights on. But "keeping the lights on" is a terrible mission statement.

What followed was roughly eight years of doing work I didn't love.

I want to be careful here because it wasn't all bad. We helped a lot of companies. We built a real business. Worked with some truly amazing people. Aaron and I created something meaningful with Predictable Revenue. But I spent most of those years searching for something I'd already lost. I was trying to recreate the magic of 2014, 2015, 2016, those early days when everything felt electric and possible and like we were building something that mattered.

You know that feeling when you're at a party and you can tell the energy has shifted but you don't want to leave because maybe it'll come back? That was me for eight years. Standing in the corner, nursing a drink, waiting for the DJ to play the song that made the first hour so great.

The song wasn't coming back. The party had moved somewhere else. I just couldn't admit it.

Every few months I'd get a burst of energy about some new angle. A new product idea. A new way to package the consulting. A new market to go after. And for a few weeks it would feel like the old days. Then reality would set in, and I'd realize I was just rearranging deck chairs again.

I think this is one of the most dangerous traps in entrepreneurship, and nobody talks about it enough.

We talk all the time about persistence. Grit. Not giving up. Every founder biography is a story about the person who almost quit but didn't, and then everything worked out. We celebrate the hold-on stories.

But there's a version of holding on that isn't grit. It's fear wearing a grit costume.

Real grit is staying in the fight because you genuinely believe in what you're building and the evidence supports that belief. Fear dressed as grit is staying because you can't imagine who you are without the fight.

I was the second one. For years.

The outsourced sales development clients kept coming in. The consulting revenue held steady. We grew. We hit 85 employees and $5 million in revenue. From the outside, it probably looked like mission accomplished. But I have never been unhappier than when we had 85 employees. Not because of the people. Because of what it meant. It meant we had a real services business, and a successful one. But I didn't want a services business. I wanted to build products. I wanted Carb.io to work. And I couldn't get through the fear that if I shut it all down or found my way out, I'd never be able to start something again.

So I stayed. And the thing kept growing in a direction I didn't want to go.

And here's the cruel irony. The thing I was hanging onto out of fear became something that wouldn't let me go. We tried to sell a few times. But you know what every buyer wanted? Me to stay for two to four years to help with the transition. You know what's worse than being stuck in your own company? Being stuck in someone else's with a big chunk of your net worth on the line. No thank you.

I'm on the other side now. I'm still an entrepreneur. I'm building ReplyLoop with Matthew, doing customer development the right way this time, writing this newsletter, helping founders through my consulting work. The fear that I'd lose the thread forever turned out to be completely wrong.

But I can't pretend those eight years were easy. And I can't pretend they were necessary.

If I could go back to 2017 me, here's what I'd say: ending a thing doesn't mean you're not an entrepreneur anymore. It means you're an entrepreneur who's between things. And "between things" is actually one of the most powerful places to be, because you're free. Free to listen to the market without bias. Free to follow your curiosity. Free to build something you actually want to build instead of something you feel obligated to maintain. Free not to work 12 hours a day on a business you hate running.

The courage isn't in holding on. Sometimes the courage is in letting go, trusting that what makes you an entrepreneur isn't the company you happen to be running. It's something deeper than that. Something that doesn't disappear just because you close a chapter.

I'm not naive enough to think everything I touch from here will work. ReplyLoop might not become what we want it to be. VClist might not hit. Something will eventually need to end.

But what I keep coming back to is the lost cycle. I could have shut down Carb.io, started something new, and seen it through to whatever conclusion it found. I'd still be here in 2026 ready to work on the next thing. Instead, the fear cost me a cycle. A whole company. Another shot at chasing the dragon of strong product-market fit.

So next time, I want to be intentional about finding that ending. I want to recognize the moment when persistence stops being strategy and starts being self-preservation. I want to have the conversation with myself honestly, without the identity panic clouding the picture.

Because the worst outcome isn't shutting something down. The worst outcome is spending eight years in a holding pattern, waiting for a feeling to come back, when the feeling was never in the company. It was in the building.

And you can always build again.

Collin

PS - I didn’t want to write this email. Well, I wrote it, then I read it but I still didn’t want to send it. But chickening out seemed like the wrong move so here we are. Hit reply and let me know if it resonated.

PPS - Thanks Ryan! The best part of this newsletter is getting to interact with folks that have read the book, whether it’s in the replies to the newsletter or hanging out on the monthly GTM calls. If you want to be cool like Ryan, you can check out the book he’s reading here. (spoiler alert, it’s my book).