[inetknght]

> I’ve worked with hundreds of startups over the last 20 years.

That's averaging 5 startups every year. How can you get good experience, or even truly understand a business, if you're averaging just around two months at a company or multiple companies in the same period?

[projectazorian]

He said "worked with" not "worked at." Likely as a contractor. And if so it's not uncommon for some projects to be very short while others might take 10-20% of your time for 2-3 years. Plenty of time to gather domain knowledge especially if clients are clustered in the same industry.