Charlie Songhurst – Lessons from Investing in 483 Companies - [Invest Like the Best, CLASSICS]

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people.  Charlie Songhurst is a brilliant strategist, accomplished executive, and prolific angel investor. This episode is one of my all-time favorite conversations, not just on the podcast, but period. Please enjoy this timeless discussion with Charlie Songhurst.

For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠here⁠.

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Show Notes

(00:00:00) Welcome to Invest Like the Best

(00:01:25) Stack ranking the vices of power, money, and fame

(00:02:41) Memorable response to the stack ranking question

(00:03:13) Best scenario to explore this stack ranking concept

(00:03:55) Other ways to rank founders

(00:04:44) Quick look at this career

(00:05:16) Time at Microsoft

(00:06:03) Features he looks for in startups

(00:10:55) Managing the declining curve of productivity

(00:14:55) Why founders are often unique people

(00:14:57) ⁠Jeff Gramm Podcast Episode⁠

(00:15:04) ⁠ Aliens, Jedi & Cults⁠

(00:09:43) How early entrepreneurs need to make recruitment a serious part of their work

(00:23:06) How successful founders win the best candidates

(00:25:27) The East Coast vs. West Coast investment strategies

(00:30:40) When it’s time to bring in quantitative factors into early stage investing

(00:34:36) The markers that pop up in companies that hit

(00:37:22) Boring but successful investments

(00:39:28) Investor aesthetics

(00:41:29) Characteristics of investors that he believes are important to success

(00:42:57) Impacts of Covid and some of the permanent changes that have happened as a result

(00:47:49) Investing opportunities in the local community

(00:49:13) His take on cryptocurrencies

(00:53:47) Most misvalued asset in the world

(00:55:16) Investing opportunities in Europe

(00:57:34) Make up of his 483 investments

(00:57:58) ⁠Matt Clifford Podcast Episode⁠

(00:59:17) Curation as a skill

(01:01:54) Timing and startup success

(01:05:11) Kindest thing anyone has done for him