Q: Dear SaaStr: How Can I Develop Confidence as a Startup CEO?

We’ve all been there in the early days — and even beyond.  You can have 1000% conviction in your start-up but still not be 100% confident in yourself as a CEO yet.  It’s OK.  It’s natural.

But you need to be confident enough to lead the team and make everyone believe.  At least 95%+ confident you can build something great.

Some ideas:

  • Find an amazing co-founder that is better than you that believes in you.  This goes very far.  You truly feel unstoppable when you have a partner than just knows you can build a unicorn together — and that’s even better than you.
  • Get great at just one important thing, especially getting customers.  If you are the best in the company (maybe even the only one in the company) at acquiring customers, you’ll gain a lot of confidence here.  Find your 10x feature that customers will value and pay for, even if it’s not enough to get you to $10m ARR, let alone $100m ARR.  More on a 10x feature here.
  • Find one amazing mentor or investor that you completely look up to you — that bets on you.  If she sees it in you … that’s telling.  Most of us don’t have this, and we miss or don’t appreciate it enough when things are starting to get good.
  • Care about your team for real.  Caring about your team and colleagues alone isn’t enough.  Your team needs to look up to you.  But knowing you’ve got their back, that you are helping them achieve their goals, and that you’ll never throw them under the bus … will help.  You need your team to believe in you.
  • Be aggressive AND humble.  Don’t be a wallflower.  Don’t be weak.  Be aggressive.  But listen and be humble.  People will respond to this, and it will create a confidence loop.
  • Do as much public speaking as you can.  The more you have to pitch it, the more confident you’ll become.  At least, externally.  Do more events, meet more investors, whatever.  Put together a YouTube channel and a podcast where you speak about your industry.  It always helps.
  • Don’t ever express even a hint of optionality.  Don’t let anyone think for one nanosecond you aren’t 110% committed for 7-10 years.  No matter what.  Period.  Folks have to believe you will always find a way.  Even if you don’t really know how the frack you’re gonna pull it off at this moment.
  • Be the first one in and the last one out.  Not literally, since most of us don’t have offices anymore, but in commitment.  Later, you don’t have to do this, and probably shouldn’t.  Don’t ask anyone else to do this.  Tell them to go home.  But as a first-time CEO, demonstrating insane commitment by proxy, by being first to show up to practice and the last to leave after the game … it works.

Just pick some that work for you.  Lead by example.

(note: an updated SaaStr Classic answer)

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