Bill Gurley on

regret

5 quotes · Oct 2025 – Apr 2026

Saidverbatim, newest first

  1. Gurley cites survey data showing 60% of people would choose a different career if they could start over.

    “we did a survey where we asked people if you could go back in time and start your career over again, would you do something different? Six out of 10 said yes.”

    4:00 · Silicon Valley Girl Clips · 27 Apr 2026 · permalink
  2. Gurley explains that regrets of inaction intensify with age more than mistakes made.

    “Daniel has, in his book on regrets, talks a lot about regrets of inaction. He calls them boldness regrets.”

    17:17 · Metis Strategy · 10 Apr 2026 · permalink
  3. Gurley's survey found six to seven out of 10 college graduates would do their career differently if starting over.

    “if you could start your career over again, would you do it differently? And in our original SurveyMonkey, seven out of 10 said yes. With Wharton, it was six out of 10.”

    5:44 · Anthony Scaramucci · 17 Mar 2026 · permalink
  4. Gurley's Wharton survey found six in ten people would choose a different career path if starting over.

    “We hired we hired Wharton to do an official academic review, and that one came out six and ten. There's a book by Daniel Pink about regrets called the power of regrets.”

    19:33 · Bloomberg Podcasts · 5 Mar 2026 · permalink
  5. Gurley's Wharton survey found six in ten people would choose a different career if they could go back.

    “It led to us doing this survey with Wharton where we asked people, if you could go back in life, would you choose a different career? And six in 10 people say yes.”

    1:09:22 · Tetragrammaton with Rick Rubin · 12 Feb 2026 · permalink

Everything Bill Gurley is on record saying · RSS