Dear SaaStr: What Mistakes Did You Make When Starting Your Business That, In Retrospect, You’re Glad You Made?

I think some of my biggest mistakes, at the time I made them, I had to make them to survive. Still, they were terrible mistakes 🙂

My list:

  • Launching too early. In both my start-ups, I launched too early. We almost always launch a bit too early, but I pushed too hard and the products in both cases needed another 3–4 months in the oven. I still make the same mistake today, the difference is I am better at mitigating the risk. The advantage is it does push the team … maybe too hard, but it works. My learning: Launching early is OK if you can afford to stumble a bit. It’s too risky if it’s Lights Out if it doesn’t work.
  • Trying to hire a “rockstar” too early. I kept making this mistake, and almost all founders do as well. In my first start-up, I hired the top COO in the world. But in the end, he wasn’t ready to join something too small. He backed out after signing the offer letter. I’ve made the same mistake again since. My learning: hiring a “rockstar” super early is OK — as long as you don’t count on them being a magician. Assume they may not work out, and maybe sure you can thrive if they don’t.
  • Moving on from founder conflict better, and more quickly. I keep also making this mistake. I hate founder conflict, and hate churn on the team. But the time often comes when founder conflict just can’t be resolved. The reason is always the same: you both just don’t have the same vision, goals — and commitment. Still, sometimes it’s a risk you just have to take. My learning: you know when a co-founder is a risky hire. And plan around that. Try harder to make it work. Communicate more. Apologize. Play to their strengths. But when it really can’t work — get zen, and try to just leverage the best of what they have built into something new. Don’t let it get under your skin. You knew it was risky.

All these mistakes almost killed me. Yet, without them I would have failed.

I keep thinking on this. A bit more here: My Top 10 Year One SaaS Mistakes. Save Yourself Some Pain & Just Don’t Make Them Yourself. | SaaStr

My Top 10 Year One SaaS Mistakes. Save Yourself Some Pain & Just Don’t Make Them Yourself.


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