It’s Not Common for Big Company Leaders to Succeed in Startups

Can experienced corporate leaders succeed in startups? Can startup leaders succeed in big companies?

The answer to both is the same:

It’s possible, but it’s not common.

Most people who are successful in big companies struggle to retrain themselves for the different sport of working in crazy startups.

Most successful startup founders and leaders struggle to learn and accept the very different sport of corporate life.

They are different sports. They are both played by smart and capable people.

You are the rare exception if you have done both well for a long time.

I have seen this inside the three companies I helped grow from scrappy startups to bigger companies. Two were acquired and I stayed on to lead the teams inside the new companies for a couple of years.

In the end, I couldn’t put up with the slow speed, the bureaucracy, and not having enough control over critical resources. I was a foreigner in these big companies and everyone knew it.

Of the hundreds of software CEOs I know who sold their companies to bigger software companies, maybe 10% of them are still with their new teams three years later.

Of the experienced corporate leaders who want to start or join early startups (less than $1-2M ARR), maybe 10% of those folks dug in and made a big impact.

They are both smart and hard-working. The games they play are very, very different.

It’s like immigrating to a new country. Most people don’t do it and fewer still totally assimilate. It’s possible, just not common.

Leaders of fast-growing startups feel these changes daily as their companies grow from 10 team members to 100 to 500 or more employees. Different sports almost every year.

This is also why most startup and growth-stage CEOs don’t stay around forever in the rare case their companies grow into billion-dollar businesses. These founder-CEOs need to change their spots at each stage to keep up.

If someone is successful at both startups and huge companies, generally they are best suited for one and put up with the other for a long time.

  • The corporate instigator that finally went out on her own.
  •  The steady company builder-founder who built the larger company they wanted to work in.

Big companies aren’t evil. Startups aren’t stupid.

They’re just very different. Pick your poison.

What do you think?


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