Michael Dempsey, Managing Partner at Compound, former analyst at Crane Partners and CB Insights, NYU graduate, and one of the most respected research driven investors in frontier technology, joins Personable to reveal how he has 5X every fund he has ever run, why he wrote the first check into Runway ML before anyone knew what it was, and how sitting out the biggest bull run in venture history in 2021 turned out to be one of the best decisions he ever made.

In this episode, Michael opens up about why he only makes six to eight investments a year and why that restraint is the entire strategy, how he called AI in 2016 when his LPs thought crypto was just for buying drugs on the internet, and why tech has gone from the coolest industry in the world to one of the most hated. From why pure capitalism is not the answer right now to why writing on the internet is the most important thing he has ever done in his career, this conversation is as intellectually sharp and honest as it gets.

This is an essential listen for anyone interested in venture capital, frontier technology, AI, deep tech investing, building conviction in a noisy market, and what it really takes to back the right companies before the rest of the world catches up.

He discusses:

◽️ How he wrote the first check into Runway ML and why being early is the only edge that truly compounds over time

◽️ Why he sat out the entire 2021 bull run when every other firm was deploying at record speed and why that was the right call

◽️ How he built a research driven firm that treats thesis building as the first class citizen and why most VCs get that completely wrong

◽️ Why tech went from the coolest industry in the world to one of the most hated and what needs to change

◽️ Why writing on the internet is the most important thing he has ever done and what it has taught him about himself

00:00 Introduction and Michael Dempsey background

02:30 Why investing and how public markets shaped the way he thinks

07:45 Compound the thesis driven approach and why research is everything

14:20 How he wrote the first check into Runway ML and what he saw that others missed

20:45 Why he sat out 2021 refused to deploy and how he stayed disciplined under pressure

27:10 How VCs find edge in 2026 and why the old playbook no longer works

34:50 Ethics responsibility and why tech is becoming the most hated industry in the world

41:30 Passive investing dispersion and how retail investors should be thinking about the next decade

47:55 Why writing online is the most important thing he has ever done in his career

54:10 Legacy predictions for 2036 and one thing every listener should take away

Michael Dempsey:

◽️ Website: https://www.michaeldempsey.me

◽️ X (Twitter): https://x.com/mhdempsey

Harvey Bracken-Smith:

◽️ LinkedIn: https://linkedin.com/in/harveybracken-smith

◽️ Instagram: https://instagram.com/harveybsmith

◽️ X (Twitter): https://x.com/harveybsmith_

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◽️ Website: https://www.personable.media/

Personable Podcast:

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Additional:

◽️ Fundraising: https://www.loulouracefoundation.org/donate

Personable is a podcast dedicated to helping listeners become the best they can be by learning from the world's best in their respective fields. This mission is inspired by my mother, Louise, who encouraged me to become the best version of myself before she passed away from cancer in 2023.

This content is for informational and entertainment purposes only and is not financial advice. Always consult a qualified financial advisor before making investment decisions. Investing involves risks, and past performance is not indicative of future results.