Today I'm talking to Haseeb Qureshi, Managing Partner of Dragonfly Capital. Dragonfly just closed a 650M fund 4 with over 4B raised in total.
Haseeb is a former professional poker player, self-taught engineer, Airbnb alum, and one of the most respected voices in crypto investing.
We talk about manhood, meaning, and what it takes to build a life worth living. Haseeb opens up about his unlikely path — from poker tables to Silicon Valley, from viral salary blog posts to leading one of the most competitive funds in crypto — and what it's actually taken to prove himself at each step.
Topics covered
- How a viral salary blog post made Haseeb the most controversial new hire at Airbnb
- The genealogy of his love for teaching — and why it starts with his mother
- Why he thinks VC is "kind of cringe" — and how Dragonfly is different
- From poker to code to crypto: how he chose his path using first principles
- What makes a great co-founder partnership (and how to stress-test one)
- Masculinity, strength, and responsibility in a feminized society
- Greatness vs. excellence: why he stopped caring about legacy
SO much more!
Timestamps
(
00:00) Intro
(
01:14) How We Met at Airbnb
(
03:00) The Viral Salary Blog Post
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06:38) Imposter Syndrome and Proving Yourself
(
09:14) The Airbnb Culture Mismatch
(
17:41) Running Dragonfly Like a Championship Team
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22:00) The Instinct to Teach
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26:40) Learning by Teaching: How to Master Any Domain
(
37:40) From Poker Player to Engineer to Crypto Investor
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41:13) Why He Chose Crypto Over AI
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43:47) Marc Andreessen and the Danger of Role Models
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48:20) Joining Metastable and Founding Dragonfly
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55:00) Why VC is Cringe (But Dragonfly Isn't)
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58:00) How to Stress-Test Co-Founder Trust
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01:11:55) The Search for Meaning in His 20s
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01:15:00) Greatness vs. Excellence vs. Flourishing
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01:18:00) Legacy — and Why He No Longer Cares
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01:22:00) Personal Writing and the Need to Be Witnessed
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01:32:45) Masculinity, Strength, and Responsibility
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01:41:50) Society's Masculinity Crisis
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01:55:30) Discipline Systems and Contracts With Yourself
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02:02:10) Vipassana and the Valley of Darkness
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02:07:20) Goal Setting: Outcome vs. Process Goals
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02:13:45) Lightning Round: Money, Mentors, Movies, and More
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02:23:20) Is Crypto Happening?
Links
Haseeb Qureshi
X: https://x.com/hosseeb
Luba Yudasina
Instagram: https://instagram.com/lifeoflubaa
X: https://x.com/LubaYudasina
LinkedIn: https://www.linkedin.com/in/yudasinal/