$4B Crypto Fund, Manhood, Discipline, VC: Haseeb Qureshi

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
(06:38) Imposter Syndrome and Proving Yourself
(09:14) The Airbnb Culture Mismatch
(17:41) Running Dragonfly Like a Championship Team
(22:00) The Instinct to Teach
(26:40) Learning by Teaching: How to Master Any Domain
(37:40) From Poker Player to Engineer to Crypto Investor
(41:13) Why He Chose Crypto Over AI
(43:47) Marc Andreessen and the Danger of Role Models
(48:20) Joining Metastable and Founding Dragonfly
(55:00) Why VC is Cringe (But Dragonfly Isn't)
(58:00) How to Stress-Test Co-Founder Trust
(01:11:55) The Search for Meaning in His 20s
(01:15:00) Greatness vs. Excellence vs. Flourishing
(01:18:00) Legacy — and Why He No Longer Cares
(01:22:00) Personal Writing and the Need to Be Witnessed
(01:32:45) Masculinity, Strength, and Responsibility
(01:41:50) Society's Masculinity Crisis
(01:55:30) Discipline Systems and Contracts With Yourself
(02:02:10) Vipassana and the Valley of Darkness
(02:07:20) Goal Setting: Outcome vs. Process Goals
(02:13:45) Lightning Round: Money, Mentors, Movies, and More
(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/