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

Invest Like the Best with Patrick O'Shaughnessy

Colossus

Investing, Business, Technology

4.8 • 2.4K Ratings

🗓️ 27 June 2025

⏱️ 68 minutes

🔗️ Recording | iTunes | RSS

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Summary

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. ----- This episode is brought to you by ⁠⁠WorkOS⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠WorkOS.com⁠⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit ⁠joincolossus.com/episodes⁠. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up ⁠here⁠. Follow us on Twitter: ⁠@patrick_oshag⁠ | ⁠@JoinColossus 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

Transcript

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0:00.0	Welcome to this classic episode. Classics are my favorite episodes from the past 10 years,
0:04.0	published once a month. These are end-of-one conversations with end-of-one people.
0:08.3	Charlie Songhurst is a brilliant strategist, an accomplished executive, and a prolific angel investor.
0:13.7	It's one of my all-time favorite conversations, not just on the podcast, but period. I hope you enjoy it.
0:20.7	Here's a puzzle. What do open AI, Cursor, Perplexity, Versal,
0:24.5	Plaid, and hundreds of other winning companies all have in common? The answer is that they're
0:28.6	powered by today's sponsor, Work OS. If you're building software for enterprises, you probably
0:33.7	felt the pain of integrating SSO, skim, Rback, audit logs, and other features required
0:39.1	by big customers. WorkOS turns those deal blockers into drop-in APIs with a modern developer
0:44.4	platform built specifically for B2B SaaS. Whether you're a seed stage startup trying to land
0:49.2	your first enterprise customer or a unicorn expanding globally, WorkOS is the fastest path to becoming enterprise ready
0:55.4	and unlock growth. It's essentially striped for enterprise features. Visit WorkOS.com to get
1:01.0	started or just hit up their Slack support. Yes, they have real engineers in there who will
1:05.2	answer your questions fast. WorkOS allows you to build like the best with delightful APIs,
1:10.2	comprehensive docs, and smooth developer experience. Go to WorkOS. you to build like the best with delightful APIs, comprehensive docs, and smooth developer experience.
1:13.2	Go to workOS.com to make your app enterprise ready today.
1:17.2	Hello and welcome everyone. I'm Patrick O'Shaughnessy and this is Invest Like the Best.
1:21.2	This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your
1:27.6	money. If you enjoy these conversations and want to go deeper, check out Colossus Review, our
1:32.1	quarterly publication with in-depth profiles of the people shaping business and investing.
1:36.3	You can find Colossus Review along with all of our podcasts at join colossus.com.
1:42.3	Patrick O'Shaughnessy is the CEO of Positive Sum.
	...

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