Invest Like The Best
Episode 181 Lessons from Investing in 483 Companies
Invest Like The Best

Episode 181: Lessons from Investing in 483 Companies

Invest Like The Best

Episode 181

Lessons from Investing in 483 Companies

Charlie is an investor and the former head of strategy at Microsoft. We cover what kills startups at each phase of their funding, the importance of recruiting the best people, and how boring investments can be successful.

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[00:01:25] – (First question) –  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

[00:19:43] – 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 mis valued 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

Lessons from Investing in 483 Companies

Introduction

Patrick
So, it's a two part question, one is stack ranking the virtues: working with people you like; working on amazing problems; and having impact. And then the three vices: power, money; and fame. You can't avoid them, but they have to be viewed separately. And it's really trying to get at the differences between them. There's no good answer, but there are definite good fit answers.

So, someone who's interested in power tends to be better at execution. Someone's more interested in money, tends to think more about some capital efficiency. I tend to avoid people interested in fame, but if you are doing something in showbiz, it would presumably be the number one criteria. If you think about the difference between impact, intellectual interest, working with people, you really get impression of where people are going to be happy and where they're not going to be happy.

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