Listen to This Podcast Episode Here
by Patrick O’Shaughnessy

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