Startups are hard. What was a consistent theme in the founder discussions is that founders were not having fun. In the attributes of jobs that I want to have, hard + not fun is not a combination I want.
I'm naturally optimistic, and considered how I could avoid it. What made them unhappy? What makes startups hard?
I've got a lot of thoughts on what makes startups hard. I've never had so many balls up in the air at the same time - multitasking and learning new skills are two of the top reasons, if not the top two. In many ways though, I love that it's hard. As long as I'm enjoying it.
But what makes most founders unhappy? Even Stewart Butterfield, CEO of Slack, commented at a recent conference I attended "It sucks being the CEO of a startup that's doing super well." Man, even if you're doing super well as a founder, you're still unhappy? What am I getting myself into?
In talking to a well known VC recently, I discussed my last sabbatical, where my wife and I took our kids around the world for a few months. He commented how much he wished he could do that, he was just waiting for the right break in his career. I offered some words of encouragement that you just need to set a date and go. His response was that he had four funds he was responsible for - there's no good breaks in his line of work. I don't think he's going to make it on that vacation while his kids are still kids. Sad.
So back to "should we take funding?" On one hand, it would allow us to hire people and move more quickly. On the other hand, my new boss(es) may have a similar mindset to the VC - very focused on the success of those funds. Having money that makes more money, while a perfectly admirable pursuit, should not feel like my purpose.
From talking with founders, it seems like they're feeling the pressure of that pursuit even more so that the pressure to solve the problem that originally stoked their passion. When the pressure to multiply money overtakes the pressure to passionately solve a problem, I think people become unhappy.
For founders who are in it for the money, this is probably not an issue. For me, it may be.
While we don't know if we'll need funding down the road, it seems like a likely path to becoming less happy, not more.
For now, I'm cautious, and planning to bootstrap.
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