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Lenny’s Podcast111 min

I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea.

Andrew Wilkinson · Jul 3, 2025
Key learnings
  • Choose a business in an area you're genuinely interested in, but look for the unglamorous niche where competition is low…
  • Pick a first business that delivers a quick, simple win, since early success builds the confidence and narrative needed to keep…
  • Look for a unique edge (skills, background, or access to audiences) and pivot toward the most profitable customer segment for…