Solutions with Henry Blodget

Legendary VC Bill Gurley: How to Thrive in Your Career

7 snips
Feb 2, 2026
Bill Gurley, veteran venture capitalist behind early bets like Uber and Zillow and author of Running Down a Dream. He recounts pivoting from engineering to finance and the curiosity that drove his career. He explains spotting exceptional founders, why Uber’s network effects mattered, and why AI may become a winner-take-all battleground. Practical career wisdom and big tech strategy collide in lively conversation.
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ADVICE

Keep Options Open Early

  • Do explore different careers early and allow yourself to switch after trying something for a few years.
  • Avoid locking into high-cost lifestyles that reduce flexibility to change paths later.
ANECDOTE

From Engineer To Wall Street Analyst

  • Bill Gurley switched from engineering to Wall Street after realizing he didn't want to do engineering for 30 years.
  • He cold-called analysts, got nine no's and one yes, and then proactively wrote a 20-page PC industry analysis to land coverage.
ANECDOTE

Danny Meyer’s Risky Learning Path

  • Danny Meyer left a high-paying sales job for humble restaurant apprenticeships, even paying to work in top restaurants.
  • He learned he preferred the front-of-house role and built a hospitality business from that insight.
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