Pitch meeting mistakes, uncomfortable questions, and fantastic failures, with angel investor Donald Thompson

As an angel investor, Donald Thompson has had some wins and some fantastic fiascos. On today’s show, Don asks Tim what he looks for in an founder, what mistakes he’s seen in pitch meetings, why an investor might choose venture capital over angel investing, and why he’s decided to share his knowledge with other investors.


Voiceover: Welcome to First Check, a podcast so you can learn how to be the next great venture capitalist or angel investor.

You’ve seen the Uber’s, Google’s, and Pendo’s of the world; the 10 X to 100 X returns. And you want to know how you can get in on the action. As a partner at Cofounders Capital, Host of First Check, Tim McLoughlin has invested over $43 million in startups. And on this podcast, he’s going to share with you what works and what doesn’t so you can be ready to write your first check.

On each episode, Tim brings on investors and founders so they can tell you the ups and downs of venture capital and what lessons they’ve learned along the way. But on this episode, one of the limited partners at Cofounders Capital is interviewing Tim. Donald Thompson is the CEO of The Diversity Movement and Walk West, and the host of the Donald Thompson Podcast.

He’s a serial entrepreneur and angel investor, but as you’ll find out, his investments haven’t always panned out. So today, Don is an investor soaking in the knowledge on how to become better.

Tim McLoughlin: So, welcome, Donald. Thanks for joining us for the first episode. How are you doing?

Donald Thompson: I’m doing good. Tim, I really appreciate it. I’ve been looking forward to this all week. With the back-to-back calendar life, we’re all rolling to get the chance to chop it up and talk about some wins and some misses. I’m all in.

Full Episode Transcript

Donald Thompson is the CEO of Walk West and The Diversity Movement, and is the host of the Donald Thompson Podcast.

First Check is hosted by Cofounders Capital partner Tim McLoughlin, and is a production of Earfluence.

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