Q:  What are the signs that an entrepreneur will always be small time?

“Always” is a bit extreme.

But let me share what I’ve learned are signs an entrepreneur likely won’t be going for it / won’t build something big.  And there’s nothing wrong with wanting to be part of a less intense journey.  That can be better in many cases.

From my experience here are the top signs though that a CEO isn’t really looking to build a unicorn:

  • Talks a lot about selling the company for “say, $20m-$30m”. This is a very logical thing to think about. But selling your company for $20m-$30m isn’t consistent with raising VC capital or going big.
  • A lot of immature language from the CEO, especially on social media. This I’ve found to be a big flag in B2B/SaaS. You have to carry yourself as the CEO you want to be in 2–3 years, and act with that level of professionalism. Including on social media, etc. CEOs that act immature on social media I’ve found often don’t go that far. Great CEOs don’t think the world is out to get them. Then tend to be realistic but positive-sum folks.
  • Lack of fluency in the competition and the competitive landscape. Folks that are going big know the competition cold.
  • Changes strategy too often. Your tactics can change each quarter or faster in the early days. But your strategy shouldn’t change weekly or monthly. That lack of conviction in having the right vision is a big flag.
  • Doesn’t really know what the customers think. In B2B/SaaS, the best CEOs are always close to the customers. When they don’t know what a Top 10 customer thinks … that’s a bad sign.
  • Never hires any great VPs. Hiring is tough. It’s always tough. But the best CEOs find a way. You can’t scale without great leaders.
  • Doesn’t share enough metrics, data, etc. Especially if things aren’t perfect. The best CEOs share when times are great, but also tough. CEOs that go dark when things are tougher … I’ve rarely seen them come back and go big.

A related post here: 11 Signs To Predict If a Venture Investment Will or Won’t Work Out | SaaStr

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