3i Member Spotlight

3i Members

Listen to the 3i Member Spotlight podcast for interviews and insights with notable 3i Members in technology, finance, and real estate. In these thirty-minute episodes, our members share their success stories, lessons learned, and invaluable business wisdom. 3i Members is an invitation-only investment network designed for founders, family offices, and fund managers, founded in 2021 by Mark Gerson (GLG), Billy Libby (Upper90), and Teddy Gold. Learn more at 3imembers.com.

  1. Sep 3

    Payment Rails, First Principles, and the $100,000 Black Hole with Alex Fine of Fun

    Our latest Member Spotlight podcast features Alex Fine, Founder and CEO of Fun (fun.xyz), the payments company building the deposit and withdrawal rails behind platforms such as Polymarket, Aave, and Lighter. Fun moves more than $18 billion annually for users in over 100 countries, following a recent $72 million Series A led by Multicoin Capital and SignalFire. In conversation with 3i Members Co-Founder and Chairman Mark Gerson, Alex traces his path from a Bay Area kid who idolized startup founders the way other kids idolized rappers or sports stars to building the infrastructure that quietly moves billions on-chain. He entered Stanford already planning to drop out and now focuses on solving one of crypto's biggest challenges: making blockchain payments reliable at scale. In this episode, Alex shares: The investor playbook: how first-principles thinking shapes his approach to building a business and his conversations with investorsThe $100,000 black hole: how a $400,000 transfer lost $100,000 in conversion and why solving that problem is at the core of what Fun doesWhy "good enough" isn't: why "move fast and break things" is the one startup mantra Fun can't afford to followWhere blockchain growth is heading: why 98% of Fun's business is already outside the U.S. and why Alex sees trillions moving on-chain00:00 Welcome and introduction01:27 The first company, built in middle school03:22 Stanford, and deciding to leave04:23 Who should go to college now06:27 The problem: money sent into a black hole07:14 Why value moves from databases to blockchains09:01 What databases cannot do11:37 A $400,000 transfer that arrived as $300,00014:09 Mistake-proof rails, and why the biggest orders get the worst price15:50 Why Fun stays invisible to the consumer16:35 Why early startups have no moat19:55 Talent density21:13 Perfectionism, six nines, and Henry Ford24:10 Rejecting work-life balance25:29 The top priority: pull-based fiat rails26:42 When the world hears about Fun27:55 Ten years out29:39 Reflecting on 3i

    Payment Rails, First Principles, and the $100,000 Black Hole with Alex Fine of Fun
  2. 07/24/2025

    The Pioneer of Fintech: How Mitch Caplan Built the First Branchless Bank and Transformed E‑Trade into a Digital Powerhouse

    Mitch Caplan brings over 30 years of experience leading innovation across the financial‑services industry. He co-founded Telebanc, the first branchless bank in the U.S., and scaled it from $50 M to $5 B in assets before striking a $1.8 B sale to E‑Trade that was negotiated and announced in just nine days. The deal formally closed the following January. He then served as CEO of E‑Trade, cutting $1 B in costs, and building one of the first fully integrated online financial platforms.  Caplan later served as CEO of Jefferson National, where he launched a tech‑enabled, low‑cost tax‑deferred investment platform that was ultimately acquired by Nationwide. Today, he is President of Tarsadia, a $2 B+ investment firm where he oversees strategy and investments across fintech, healthcare, technology, and real estate. Most recently, he was named interim CEO of Yieldstreet, where he also serves as Chairman of the Board. Mitch has been a 3i Member since 2023.  In this episode:  • How Mitch built the first branchless bank, and why it worked when regulators said it wouldn't  • The story behind the $1.8 B E‑Trade deal, and how it was negotiated and announced in just nine days  • Why most fintechs fail, and what Mitch looks for in companies built to last  Learn more about 3i Members at 3imembers.com and follow us on LinkedIn for updates.

    The Pioneer of Fintech: How Mitch Caplan Built the First Branchless Bank and Transformed E‑Trade into a Digital Powerhouse
4.7
out of 5
14 Ratings

About

Listen to the 3i Member Spotlight podcast for interviews and insights with notable 3i Members in technology, finance, and real estate. In these thirty-minute episodes, our members share their success stories, lessons learned, and invaluable business wisdom. 3i Members is an invitation-only investment network designed for founders, family offices, and fund managers, founded in 2021 by Mark Gerson (GLG), Billy Libby (Upper90), and Teddy Gold. Learn more at 3imembers.com.

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