Dear SaaStr: What Were Some of the Toughest Lessons You Learned About How to Build a Successful SaaS Business?

Some of the toughest lessons I’ve learned … and continue to re-learn:

  • Even very talented co-founders may leave. You need to also make sure they are 110% committed. More here.
  • Very mediocre VPs are often very good at talking the talk. Mediocre execs often talk the talk even better than the best up-and-coming ones. You have to make sure they can actually do it. Especially at your stage.
  • Your first and even second release likely won’t be good enough. It just takes longer to get a true sellable product to market than most budget for.
  • Almost no products just sell themselves. How will you get folks to find it, let alone buy it?
  • As a first-time founder, a lot of folks won’t believe in you. But it’s OK. You just need a few to. A few anchor customers. 1 great investor.
  • Great folks will leave. I’m still re-learning this. But do whatever you possibly can to get them to stay.  More here.
  • Competition can maim you, but it rarely kills you. If you truly have a better team than the other guys, you can still beat them. At least in one niche, one segment. Yes, worry about the competition. But worry more about how to close the next customer.  More here.
  • Pick VCs and investors you can truly trust. This is more important than adding value. This is much more important than being “nice”. Actually, investors that seem too nice are often just selling something. Folks you trust actually often give you some hard, tough advice.  More here.
  • You will start to slow down around $1m-$2m unless you bring in a good VP or two. You just can’t be the VP of Everything yourselves anymore.
  • As soon as you have even 2 Big Customers, bring someone in full-time to make them happy. This always pays off.  Customer Success really is a single-digit hire (i.e., in your first 9 employees) for most of us.  More here.

Just a few!

And a related post here:

The Top 10 Pieces of Advice I’d Give to My Younger CEO Self

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