Dear SaaStr: What Are Some Things That Make a Founder Look Naive?

A few in my experience:

  • Mocking the competition, especially successful competition. The best founders do win, but they also profoundly respect the competition — and understand and learn from them.
  • Hiding core issues during fundraising. Hiding that they don’t really have a CTO, or that they’ve already raised a ton of money, or other big issues. Get them out there, at least during fundraising.
  • Thinking they can Go Big with just a tiny team or only a tiny amount of funding. Sometimes this is possible, but it’s rare. Few of us are Craigslist or Mailchimp.
  • Arrogance. This just never plays well. I love the talk from the co-CEO of Atlassian below saying he still has Imposter Syndrome. Sometimes a little is OK from a top CTO, but basically never a CEO.
  • Generic outreach. The best founders reach out with amazing emails. Not generic LinkedIn Inmails.

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