My guest this week is Bill Gurley, a general partner at Benchmark Capital and one my favorite investment thinkers. As you’ll hear, despite enormous success through his career, Bill is clearly still in love with business and investing. Where many might discuss past glories, I’ve been incredibly impressed with how both Bill and his partners emphasize the current portfolio and market landscape. I’m thankful to have had the chance to speak with him in this format. I hope you enjoy our conversation.

Show Notes

1:13 – (First Question) – The idea of increasing returns

1:21 – Competiting Technologies, Increasing Returns, and Lock-in By Historical Events

2:07 – Complex Systems Theory – Santa Fe Institute

4:35 – Markers that could be a sign of network effect in a company

6:27 – The opportunities for companies to capture network effect

8:46 – Are there certain teams/leaders that are more conducive to leading a network effect company

11:55 – Liquidity quality

13:35 – How important is the revenue model at the beginning

15:59 – Fascination with Nextdoor

17:56 – Paradox of Choice

18:39 – Finding opportunities

20:17 – Potential marketplaces and assets that could be commoditized

20:20 – All Markets Are Not Created Equal: 10 Factors To Consider When Evaluating Digital Marketplaces

21:39 – Usage yield on the world’s assets

23:50 – Has technology changed the world of value investing

26:28 – Hyper niche marketplaces

27:52 – Challenges of labor marketplaces

30:12 – User generated content businesses

32:44 – People who are capable of building UGC businesses

33:16 – His interest in Discord

34:31 – Factors of a healthy marketplace

37:57 – Fools’ gold in marketplace businesses

39:04 – How influx of cash is impacting the marketplace business landscape

40:43 – All Revenue is Not Created Equal: The Keys to the 10X Revenue Club

43:20 – How does the influx of money into the space impact him

46:44 – Spending money to attack top brands

50:32 – Regulatory capture

53:36 – His thoughts on the IPO market

57:49 – How did he realize this was his passion

1:00:42 – Qualifying his passion

1:01:52 – Favorite thing about working with entrepreneurs

102:48 – Honing your craft

1:04:33 – Making yourself a good mentor

1:05:56 – Kindest thing anyone has done for him