How did WarmUp start, and what did six months of betting on it teach me?

WarmUp started in 2019 as a six-month bet. The consulting company I worked for, Fretless, was being acquired, and I had a choice: take the safe job, or go full-time on WarmUp. I gave myself six months. If it could not pay the bills by then, I would go and get a regular job.

That was nearly seven years ago. It worked, barely, and I first told the story on LinkedIn. This post is the longer version, with what the years since have taught me.

Why did I give myself six months?

I gave myself six months because a deadline turns a dream into a test. Six months was long enough to find out whether people would pay for what we did, and short enough that I would not drift. If it did not work, there was no shame in having tried.

Honestly, those were the scariest six months of my life. The deadline did not make the fear go away. It did make the question clear: does this pay the bills yet, or not?

What changed between selling deals and building a company?

What changed was the kind of puzzle. In sales I spent years solving how to close a particular deal. Building a company is a different level: how do you position a business so the right customers find it, and how do you build systems that create opportunities consistently instead of one deal at a time?

The deal puzzles are still fun. But the go-to-market engineering ones, GTME for short, are where the real leverage is, and they are the most interesting problems I have worked on. A good deal closes once. A good system keeps producing conversations after you have stopped thinking about it.

That shift is also the job we do for clients now. We build the systems that find, qualify and route the right buyers, run them until the numbers hold, and hand them over. You can read how that works in what GTM engineering is.

Why should you find people smarter than you and pay them?

You should find people smarter than you and pay them because the cost of not knowing what you should know compounds. Every month spent guessing at something an expert could teach you in an hour is a month of slower decisions, and the gap widens while you guess.

Dan Rosenthal has taught me more about GTM engineering than any course or book. I once asked him, seriously, how much I would have to pay him to be my friend every month. He laughed kindly. I was not joking.

The lesson is not about Dan in particular. It is that the fastest way to learn a field is to spend time with someone who is already good at it, and that paying for that time is one of the best investments a small company can make.

How do you get through the hard stretches?

You get through the hard stretches by expecting them and trusting that they end. Building a company hurts more than you think it will, more often than you think it will. The ability to endure may be the most important trait a founder has, because most people quit before they make it, and some get very close and still quit.

My former boss Brian Rowe used to say that every day you do not quit, you are one day closer to not dying. It sounds dark, but it is true.

We have had two big climbs.

1. The pivot. In late 2020 we had to change the entire business model, from software to services, in six months. It was a complete rebuild, and it was hell.
2. Clay. Years later we had to learn Clay and learn how to sell it. That was another huge mountain, and Deisy Lewis led it.

Both times, the thing that got us through was not a clever plan. It was not stopping.

Why treat everyone like humans?

Treating everyone like humans is the one rule I have tried to run WarmUp by, because it sounds simple until you notice how many decisions it touches. How you treat employees, clients and partners is decided in small moments every day, and a single clear rule makes those moments easier to get right.

Miles Sterrett and Davey Strus lived this during my years at Fretless, and I carried it forward. I have not been perfect. But the rule has guided my decisions, and I have ended up surrounded by people I actually want to spend time with.

That is the best part of surviving this long. Right now we have interesting problems, great clients and a team I genuinely like working with. Most of the time you do not get all three at once.

What would I tell someone deciding whether to keep going?

If you are building something right now and wondering whether to keep going, keep going. The market for what we do is the strongest I have ever seen, and GTM engineering is growing fast. The hard part is staying in the game long enough to be there when it turns.

If you do it long enough and do not compromise on the human part, work stops feeling entirely like work.

If you want to talk about your own journey, reach out. Do what I did with Dan. You can find Deisy and me on the about page, with a link to each of our LinkedIn profiles.