Start-up Investing: Head Versus Heart

Jason Fried | Inc

Over the years, we’ve had lots of chances to invest in other businesses. But it never felt right. Until now.

Last month, we did something we had never done. We invested in another company. We purchased a small, noncontrolling stake in the Starter League, a Chicago-based business that teaches people with no experience how to program.

Over the years, we’ve been offered opportunities to invest in other companies or individuals. In some cases, the financial or strategic rationale was easy to see, and we probably could have made good money if we’d pulled the trigger. But we always balked, and I don’t regret it.

Because even if those deals were potentially lucrative, the opportunities simply–for lack of a better phrase–didn’t feel right. You have to live with your decisions every day. Why live with one you’re uneasy with? “Because it’ll make you money” is a common reply. But I don’t think that’s good enough.

What makes the Starter League different? For one thing, we love businesses that have been built to scratch a personal itch. Mike McGee and Neal Sales-Griffin, the company’s co-founders, wanted to learn how to program. They bought a ton of books and tried a bunch of online tutorials. Neal and Mike are smart guys, but they couldn’t figure it out.

As it happened, one evening the two of them were in the classroom-style theater in our Chicago offices; we’d loaned the space to an instructor for a three-hour course about the programming language Ruby. There was another neophyte student in that class: me. I’m a business guy, not a programmer–though I’d like to learn.

Neal was sitting behind me. After the class, we chatted a bit. Neal told me about how difficult it had been to learn to program. He also told me that he and Mike were thinking of starting the kind of school they wished existed.

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