---
title: "Relentless Optimism: Lessons from the people who built Venmo."
description: Venmo's co-founder, former CEO and first investor talk about creating Venmo during a fireside chat at SFJAZZ.
image: https://blog.basistheory.com/hubfs/VenmoChatRecap.png
---
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October 1, 2026
 [Basis Theory](https://blog.basistheory.com/author/basis-theory-team) ·
[Payments](https://blog.basistheory.com/tag/payments)
# Relentless Optimism: Lessons from the people who built Venmo.
## Table of Contents
- [Lessons From the Stage](https://blog.basistheory.com/venmo-fireside-chat#Stage)
- [The Lesson to Take Home](https://blog.basistheory.com/venmo-fireside-chat#Home)
- [Watch the Full Conversation](https://blog.basistheory.com/venmo-fireside-chat#Video)
If experience is the greatest teacher, there aren’t many classrooms better than the one we created at SFJAZZ after Labor Day.
Basis Theory organized a fireside chat with the founders, early investors, and team members of Venmo to reminisce about the early days, and what it took to build a fintech business. The nostalgia factor was high, and the insights were candid, inspiring, and a little silly from the folks who built what we now know as a verb.
“The through-line from the entire evening was having relentless optimism,” explains Peyton McGovern, Marketing Program Manager for Basis Theory.
Below are highlights from the guests on stage and the key lesson we took home. A full video of the conversation is at the end of this post.
The quotes below have been edited for clarity.
## From the Stage
### Iqram Magdon-Ismail, Co-Founder of Venmo
“In the early days, we knew all of our users. And because we built Venmo on a BlackBerry, everyone was sending these quirky messages to each other. You could make a Venmo payment over BlackBerry and that was part of our growth.”
“The social feed came from us getting these daily activity emails, and it’s like, look at all these people using Venmo. The notes were kind of interesting. So what if we just put them out in the public and built privacy around it? And now we have the social feed.”
[Follow Iqram on LinkedIn](https://www.linkedin.com/in/immigrantgroove/)
### Bill Ready, Former CEO of Venmo and Braintree
“We were looking for great talent to help us build out a consumer side with what we were doing at Braintree and as we looked around, we met \[Venmo Co-Founders Iqram Magdon-Ismail and Andrew Kortina\] through an entrepreneur event. These guys knew nothing about fintech, but they would find a way and figure it out. I was super excited about the possibility of coming together and building.”
“And there’s this advantage of having a beginner's mind, and not knowing being an advantage. These guys were always going to find a way.”
“When we started working together, Venmo had something like 3,000 users. It had its first iPhone app, and the social feed was brand new. This was 2012. We had a lot of debates, and even within the Venmo team there were a lot of debates on this. I didn’t love it (the social feed). I saw so many ways for it to go wrong. But there were really interesting conversations happening, and it was an appropriate forum where it was five to 10 people who you wanted to have more intimate experiences with.”
[Follow Bill on LinkedIn](https://www.linkedin.com/in/williamready/)
### Sam Lessin, First Investor in Venmo
“It takes being irrationally optimistic, especially for things that change the world.”
“Obviously Venmo is a technology company, but in a lot of ways it is culturally pitch perfect in terms of the execution.”
“Venmo is difficult to talk about, and credit goes to the people who were on that journey and were willing to defend it. It was a cultural startup, run by cultural leaders, who understand technology.”
[Follow Sam on LinkedIn](https://www.linkedin.com/in/wlessin/)
[Return to Top](https://blog.basistheory.com/venmo-fireside-chat#TOC)
## The Lesson to Take Home
Despite opening this post with the idea that experience is the greatest teacher, the irony is that Venmo’s story argues the opposite.
The team didn’t know what money transmitter licenses were, there was skepticism about the social feed—and yet they built Venmo anyway.
Colin Luce, CEO and Co-Founder of Basis Theory, moderated the fireside chat and is leading the release of a documentary on the origins of Venmo, said ignorance in a specific domain can be a blessing.
“It took unabashed optimists to get Venmo off the ground,” Luce said. “Venmo is a verb now, we take it for granted. But it took people who were naive to pull this off, the idea of relentless optimism. You need that kind of attitude, and these guys have it.”
More than a decade after Venmo began, that attitude was felt all over the room at SFJAZZ among the agentic builders, fintech founders, and payments teams.
The next Venmo will likely not come from someone who knows all the rules, either.
[Return to Top](https://blog.basistheory.com/venmo-fireside-chat#TOC)
## Watch the Full Conversation
[Return to Top](https://blog.basistheory.com/venmo-fireside-chat#TOC)
[](https://blog.basistheory.com/hs/cta/wi/redirect?encryptedPayload=AVxigLIQEQCUN7Xd%2F0%2FRvI0aehDF1cIHRekEK1VVasXqkO%2BiOh7EuSIgzqHmeoRxvGu2tunS9J28wbOwrS%2FmO0tBb9keX2gs6%2Fsl7Pcd1DndTvmLybx6dkYq5wxQO7fkWFpKOiehJsId2VTy%2B%2BfheQvBsS6a4vA4mc%2Fpz5K8Tgm%2BeVkU8k4uL23WoMH%2FmTnU97fKYjEzkEJJitqAMw87EeXBBlKl8r8wG%2B4%3D&webInteractiveContentId=171491046931&portalId=22332934)
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