Dear SaaStr: Which Mistakes Have You Learned the Most From as an Entrepreneur?

The top mistakes I’ve learned from:

  • You can do OK with a so-so founding team, but you can’t do great. And great individuals do not necessarily make great co-founders. So slow this part down. We’re all in a rush, but you can go so, so much further, and with so much less stress and drama, if you truly have a great co-founder.  More here.
  • Always Be Recruiting. Nothing matters but the team, ever, and especially once you have product-market fit. When in doubt, be recruiting. Drop other things.  If after $1m-$2m ARR, you aren’t spending 20%+ of your time recruiting … you are doing it wrong.  More here.
  • Budget More Time. Some of the worst decisions I’ve made were because I felt under pressure to deliver before “time was up”. This pressure is real. But still, somehow, budget more time.
  • Spend More In-Person Time with Customers, Partners, and People. The internet is not an excuse to not meet people. In fact, it’s a reason to meet up with them even more. There were many business relationships I should have spent more face-to-face time with. They would have been much stronger. More here.
  • Pick the Right Investors. It does matter. Yes, all money is green. But ultimately, if you are in a business that requires capital, having alignment with your goals makes life much easier. Pick investors that have your back, and that also, have the same exit / scale goals as you. At least, if you have choices.  More here.
  • Get Rid of VPs, Partners, and Others You Can’t Trust. Talent does not make up for lack of trust. If you can’t trust your team, you cannot scale. You cannot do it all yourself, at least, not after the very early days.  More here.
  • Get Rid of folks not 100% committed. Same as prior point, just a little different. You don’t have time for the semi-committed, except at the margin as contractors.  More here.
  • Paying Customer Feedback Trumps All. 90% of advisors, executives, regular old smart people you know, etc. will tell you your startup is a mediocre idea, or Too Small, or undifferentiated, or other valid criticisms. They may well be right — today. But in the early days especially, don’t listen too much to the folks that tell you why it won’t work … if there is anyone that will actually buy. Instead, focus all your efforts on replicating what does work. The reasons why even just 1 or 2 customers will buy today.  More here.
  • Great Teams Are What Makes it All Worthwhile. You’ll look back later, and in most cases, the product you built won’t matter so much. Markets change, vendors change. But it’s a great team that did amazing things together that you’ll not just remember — but cherish. A great team working on a “boring” product is a 500x better journey than a disjointed, infighting team working on a super-cool product.  More here.

A related post here:

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

(more time image from here)

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