Iqram Magdon-Ismail is the co-founder of Venmo and current founder of Jelly, a video-first social app. After building Venmo from a text-message prototype to a verb used by millions (ultimately acquired by PayPal via Braintree), Iqram is now tackling what he sees as social media's biggest problem: it became all ads, influencers, and flexing instead of genuine connection.

What you'll learn:

How Venmo started from forgetting a wallet at dinner and evolved into a cultural phenomenon
The near-shutdown moments when Wells Fargo threatened to close their account
Why Venmo raised only $3.4M total before the Braintree acquisition
The strategy behind keeping Venmo invite-only for five years
How the team's close friendship shaped Venmo's personality as a product
Why Iqram believes AI made startups polished but soulless
The shift from building for purpose (helping musicians) to building for metrics (ARR, funding)
What it's like working at PayPal after selling your startup
How Jelly uses crypto infrastructure to enable global money movement through video
Why immigrant founders bring a different hunger and work ethic to building companies

In this episode, we cover:

(00:00) Introduction to Iqram and his founder journey

(00:49) The origin story of Venmo - forgetting a wallet

(03:08) Building on Google Voice and eating credit card fees

(08:40) The near-death moment with Wells Fargo

(12:01) How the Braintree acquisition saved Venmo

(16:56) Working with Bryan Johnson at Braintree

(18:57) The regret of not having more equity in Venmo's success

(21:06) What makes Venmo feel different than other payment apps

(22:16) Why modern startups lost their personality and purpose

(26:00) Life at PayPal after the acquisition

(27:38) Consumer vs B2B founder-product fit

(30:23) Social media became a nightmare of ads and flexing

(32:20) Demo and vision for Jelly

(39:06) Using crypto and meme coins in social apps

(41:15) Why invite-only launches create quality users

(42:38) Rapid fire questions on inspiration and mistakes

(45:28) What it means to be an immigrant entrepreneur

152 - Trampled Under Snow