GB Ep 51: What I Learned from Interviewing 70 Entrepreneurs


Today I’m going to tell you some of the things I’ve learned after interviewing 70 entrepreneurs. In the last year and a half, I’ve talked to people who have founded multi-million dollar companies, billion dollar companies, and even people like Ron Klien who invented the magnetic credit card stripe. It’s been really humbling to talk to these people.

  • I’ve gotten better at hosting interviews and become more comfortable in my own skin. You can see the difference in my first interviews with Pat Flynn and Rand Fishkin. [01:42]
    • My recommendation for anyone else trying to start a podcast is to secure your first five interviews and just do them. [02:08]
  • The first commonality I’ve noticed from all of these entrepreneurs is tenacity: they continue to push and make things happen. There isn’t a willingness to back down easily. [02:32]
  • I usually ask a question about user acquisition, about how they got their first 100 or 200 customers. The answer is always the same: it’s hand-to-hand combat. [03:00]
  • The third commonality I’ve noticed is when I ask about their favorite book. Over 17 times, The Hard Thing About Hard Things has been recommended. This tells me that entrepreneurs look up to other entrepreneurs who have really made it happen. They like to take stories from biographies and make them into their own. [03:35]
  • Most entrepreneurs are very willing people, even though they’re so busy. They’re happy to give 30 minutes to an hour to share their knowledge and give back to the community. [05:00]
  • They are very methodical and focused, and they’re always willing to share about their methods. This has helped me learn to start asking better questions. [05:44]
  • They have mentors and/or are a part of peer groups. Almost all of them have mentors, and in some of the episodes we talk about Entrepreneur’s Organization, Young Presidents’ Organization, or WPO. Interacting with ambitious people who share some of the same challenges and struggles is important to success. [06:52]

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