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

This is an audience participation post. I’m genuinely considering raising cash for Predictable.ai and I would love to hear your perspective. I’ve laid out my thinking below and nothing is decided. Please hit reply if you have any thoughts or an experience that resonates.

Sunday night I sat down with my wife and said something out loud I've been chewing on all weekend.

"I'm thinking about raising money."

I didn't have a pitch. I didn't have a deck. I just wanted to hear what it sounded like coming out of my mouth. Turns out it sounded like a guy arguing with himself for twenty minutes while his wife asked better questions than most investors I've met.

Some context. I've always bootstrapped. Predictable Revenue has never taken outside money. We've taken on debt, but nobody else owns a piece of the company. And for most of my career I've been pretty smug about that.

But I'm building software now, and I think it can be a lot bigger than me. The consulting side of my business will only ever be so big. It's me, helping startups. The software doesn't have that ceiling. 

So I walked my wife through the math of venture capital, which is a fun thing to do on a Sunday night.

A VC raises a fund. Say they make 20 investments at a million bucks each, just to keep the math easy. Most of those die. A handful return the money, maybe. And they need one to return a hundred million, because that one pays for all the others.

That's the business model. They don't want dividends. They want exponential returns inside a seven to ten year window. So the only reason to take venture money is if you can see a path to $100M in revenue. If you can't see that path, you probably shouldn't take it.

Once you take it, you're on the treadmill. You can't just let the money sit there. You have to grow, and you have to grow fast, because that's what you sold them.

I said this with a lot of conviction. Then my wife asked me how I felt about building something for seven years and then starting over. And I realized I'd been describing the treadmill like it was a thing I was trying to avoid.

Here's what I didn't say in my big VC explainer.

Every couple of months I lose a client. It's normal. Consulting clients come and go. But every single time, I get this pit in my stomach. I spend a week in stress mode. I'm making calls, chasing intros, trying to replace the revenue so I can pay the team, pay myself, and keep paying for all the tokens and tools that let me build the software.

And in my head it spirals. Lose one client, then two, then we're not profitable, then by Friday night I've mentally lost the house. I know that's not going to happen. I still go there every time.

Then I rebound. I get my stuff together, book some calls, find the next client, and get back to building. And for a few weeks I feel like a wizard, conjuring software out of nothing.

Then it happens again.

That's a treadmill. It's just a different one. It's the client treadmill instead of the investor treadmill, and I've been on it so long I stopped noticing.

So the question isn't "treadmill or freedom." There's no freedom option. The question is which treadmill you want to be on.

This is the part that's a little embarrassing.

If you've read this newsletter for a while, you know Carb.io is my favourite cautionary tale. We hit about $83k MRR within three months of turning on billing, and then flatlined because churn ate every new sale. The product was janky. Table stakes features didn't work. I kept pushing sales instead of fixing it.

For the last while I've been telling you the lesson was that we grew too fast. We couldn't iterate on the feedback we were getting. That's why I've been deliberately pacing the software I'm building now.

But on Sunday night, while trying to justify raising, I heard myself say the Carb.io mistake was not raising venture.

Which is it?

Honestly, probably both. We grew sales faster than we could fix the product, and we didn't have the money to fix the product while we grew. But I noticed that the lesson I pulled out depended entirely on the decision I was trying to talk myself into.

I think founders do this all the time. Your past failure becomes a Rorschach test. When you want to go slow, it proves you should go slow. When you want to go fast, it proves you should go fast. If your lessons keep changing shape to fit your current mood, they might not be lessons. They might just be stories.

I'll be straight about why I'm leaning toward it.

The big players in my space have raised hundreds of millions of dollars. If I build the best product, they can see it and copy it, then pour millions more into go-to-market than I'll ever have.

It's like sitting down at a poker table with a short stack. You get bullied. People put pressure on you every hand because they know you can't call. You're underpowered the whole game and it's not much fun.

There's also a window. Ideas like this work for a while, and then someone else does the same thing. If I bootstrap, I'm moving down the road at 20 kilometers an hour. If someone else comes along doing 100, they get there first and the window closes.

A modest raise would let me spend next year building instead of chasing clients. Maybe hire a person or two. Mostly, it would give me back the brain space that the client treadmill eats.

And I can see the exits. There are a handful of obvious acquirers in this space. I even know a few of them pretty well.

Raising a small round doesn't mean investors run the company. They can push. They can't force me to sell. But it does change the math. Investors usually get paid back first, so if things go sideways and I sell for less than I hoped, I could walk away with nothing.

And my wife asked the question I can't answer yet: would I feel more pressure, not less? A clock on the wall. A limited amount of time to make this work. Other people's money on the line.

I don't know.

I haven't decided. I just know that "I've always bootstrapped" isn't a reason. It's a habit. And "VC is a treadmill" isn't an argument when you're already running on a different one.

The last thing my wife asked me was which path gives me more time back with my family. I told her I genuinely don't know. That's probably the question I should have started with.

So I'll ask you. What would you do if you were in my shoes? I genuinely want to hear from you, so please hit that reply button. 

Collin

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