Serious startup founders slay the big dragons that will kill their startup

When investors evaluate a tech startup or growth-stage company, they look at things like the potential market size, your team, traction, customers, and product.

But they are really asking one big question about the CEO in charge.

Can this person lead the company to overcome all the startup-killing challenges that will come their way to win this game successfully?

There are a lot of smart and hard-working leaders who can figure out the things they need to master to do well in their jobs.

The hard-but-figuroutable things like funding, GTM, building software, and hiring.

There are few founders that will overcome the 10-20 killer challenges that will come their way.

The inevitable big challenges that prevent most startups from growing into high-value companies and getting to a successful exit.

Hard challenges like these:

  • You’re running out of cash and your lead investor pulls their term sheet offer
  • Your product has problems and your lead engineers quit for a better compensation with a big company
  • You have an industry focus and a COVID virus kills that industry in two weeks
  • A competitor gets a ton of funding and aims directly at you
  • Your company grew 200% but the CEO (you) didn’t grow their abilities that fast
  • Your biggest customers stop using your software
  • A co-founder isn’t working out and is making big trouble
  • You get into some legal trouble that takes all your time
  • You hired a hotshot salesperson or engineer and they are making their peers quit
  • The market assumptions you made have shifted quickly in a different direction
  • You made some bad decisions and ran out of cash
  • You make poor or slow leadership hires that drag you down
  • A major personal crisis happens at home: sickness, family issues, mental health

These are just the common ones that big angel or VC investors expect as you grow.

It takes a special founder/CEO to face down and successfully overcome big challenges like these.

Like slaying killer dragons over and over. It’s a long movie and there are a lot of dragons. And sometimes the dragon wins.

The faster you grow, the more money you raise, and the more employees you have, the more dragon-sized challenges you will face.

I’m still amazed at the dragon-slaying abilities of startup founders like Bill Gates and Mark Zuckerberg who grew from scrappy coders to capable CEOs of very large, global companies.

They figured out a lot very quickly. But they kept slaying the big dragons that seemed to kill their competitors. Over and over.

If you say “We’re a scrappy startup now but someday we’ll be very big as a leader in our market” you are saying you are a Dragon Slayer and you will overcome all the big challenges you will face.

Is that what you signed up for? Just checking.

Investors all ask the same type of question about the CEO:

“Is this founder a slayer of all the dragons they will face to win the game?”

What are other dragon-sized killer challenges you have seen startups face?

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