Talent hits a target no one else can hit. Genius hits a target no one else can see. —Arthur Schopenhauer
The second that the next round of funding hits the bank, every new CTO starts obsessing over the same thing: Who the hell do I hire next? The answer is surprisingly non-obvious. You’re told that you always want—scratch that, need—the best of the best, your startup’s future depends on it. You’re told your company is unique, special, and it requires the most hardcore among researchers, designers, engineers, and product managers. You never skimp on who builds the golden goose. You can’t succeed with any less than that.
But, is that actually true?
Every startup-hustle YouTube video, VC podcast and celeb founder interview regurgitates that the key to success is to hire the very best people, no matter what it takes. And yet you live in the real world, with real-world constraints. You have only so much money in the bank. Only so much time and bandwidth to hire. Only so much attention in a given day. And you’re not alone in your hunt. You’re competing with hundreds of other players in your geography, industry, and problem space looking for “the best.” Many of them have a more famous brand, more cash, more promising equity, more charming founders, and maybe even a high production value promo video showcasing happy employees, rare wood office counters and a shoes-off policy.
Will you actually hire the best of the best against those odds? Many years ago I found myself in this pickle and I had to learn all the relevant lessons the hard way. I share these lessons here, so that you don’t have to struggle through that same maze yourself. My pain is your gain.
My first time around the startup world in 2012, I hardly knew what I was doing and relied mostly on luck—and unfortunately, firing—to end up with a team I could be proud of. I had no real point of reference for greatness, for what “the best” in our area could look like, and building that model required lots of experimentation, with high highs and many low lows.
The story of David, our brilliant infrastructure ops engineer at Freckle, has stayed with me ever since. David applied to the company back when we were only hiring for an ops role. We were growing slowly, so there was zero room for anybody who wasn’t absolutely essential on the team. We had no open-ended extra seat for a smart person who just happened to be on the market, unlike some companies these days.
David was 100% what we were not looking for. He had never done any ops. In fact, he had never done anything related to web dev or product engineering. I’m not sure he even knew what AWS was at that point. He was a sharp physics guy working with a professor on simulations in an academic context. He didn’t let that deter him. He wanted to work at Freckle, thanks to our reputation as one of the few software startups in the world using Haskell in production at scale. We were an odd outlier in a sea of buggy and laborious Rails apps, a shelter for people who didn’t want yet another web slop gig. And Haskell was oh-so-hot in the Hacker News programming language theory space at the time, a technology attracting software nerds obsessed with correctness and new, better ways of developing bug-free apps.
I immediately told David that he was not a fit; he had none of what we were looking for. And yet he persisted, emailing me that he would do whatever test project we threw at him, and if he bombed it, no problem, he would go away. But if he nailed it, we would have proof that he was qualified, in spite of what his CV indicated. Fine. I sent him a meaty cloud ops take-home project, expecting to never hear from him again. Importantly, this was in the days before you could have Claude Code slap that together for you in two prompts.
A day or two later, he returned the project to us, and it was pretty much flawless, doing even more than we had asked for. That was not expected. I got curious about what else he could do. We weren’t drowning in applicants anyway, so I figured I didn’t have much to lose. We took him through the usual interview process. He was humble, optimistic, well-spoken, actively communicating and taking feedback well, eager to get to work. He was pumped about everything he could learn on the job, about the doors that would eventually open if he nailed it. He didn’t have much experience, as someone who had never written commercial software before, but he was really quick to absorb everything we threw at him.
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