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

    24 JUL

    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.

    56 min
  2. Beyond Business: Intersection of Authorship and Spiritual Growth with Craig Weiss, Managing Partner of Flagstaff Ventures

    13 MRT

    Beyond Business: Intersection of Authorship and Spiritual Growth with Craig Weiss, Managing Partner of Flagstaff Ventures

    Craig Weiss is a leading Entrepreneur, Investor, and an Author. Currently, he is the Managing Partner of Flagstaff Ventures, where he brings entrepreneur-focused perspective to the venture capital field as one of the few institutional investors to have both built a unicorn as a CEO and also identified and invested in an early-stage startup that has achieved unicorn status. Craig has been a 3i Member since 2023. In this episode, Craig discusses his experience writing two books on Israel's War of Independence, coining the concept of a "karmapreneur," and finding deep community value in Зі. He reveals how spiritual and commercial aims merge to create both financial and societal impact. Listen to the podcast to learn more about: Lessons from Authorship: Through archival research, interviews, and declassified military documents, Craig uncovered overlooked historical narratives-an approach he sees as mirroring the diligence required in startup investing. Pivoting from Patent Attorney to CEO: How a background in patent law primed Craig for evaluating inventions and led to growing a vaping-tech startup that helped bring about a near smoke-free generation. Integrating Business & Spirituality: Craig reflects on seeing seemingly different domains—venture investing, intellectual life, and moral purpose—as fundamentally connected, guiding his vision for future “karmapreneurs.” Craig's Books: I Am My Brother’s Keeper: American Volunteers in Israel's War for Independence 1947-1949Fighting Back: Stan Andrews and the Birth of the Israeli Air ForceDocumentary: Above and Beyond (2014 documentary featuring Craig Weiss)Craig's Professional Links: Flagstaff Ventures (Craig Weiss's Venture Firm)Craig Weiss LinkedInAdditional References from Conversation: Reason.com article covering Sen. Rockefeller’s vaping remarksCast a Giant Shadow (1966 film about Mickey Marcus, mentioned in episode)3i Members Links: 3i Members Official Website3i Members LinkedIn

    43 min
  3. Charting the AI Frontier: From Generative Models to Market Impact with Zoë Weil, Co-Founder & CEO of Sequen AI and Former SVP at Citi

    20 FEB

    Charting the AI Frontier: From Generative Models to Market Impact with Zoë Weil, Co-Founder & CEO of Sequen AI and Former SVP at Citi

    Zoë, formerly the Senior Vice President of AI at Citi, is a distinguished leader in the AI field with over 12 years of experience. At Citi, she spearheaded the adoption of agentic AI across the firm, enhancing various business processes. Prior to this, as a Staff Applied Scientist at Etsy, she led initiatives in personalized search and discovery. A graduate of NYU with a deep background in AI, Zoë holds three patents in large language models and is an active angel investor in AI-first startups such as Tough Day, Starcycle, and Eden Labs. She is now the co-founder and CEO of Sequen AI, where she patented the first-of-their-kind scalable specialized agents that autonomously seek to maximize conversion rates. She has been a 3i member since 2024. In This Episode, Hear About: Sector Impact: Discover how AI is transforming sectors like banking, healthcare, and retail, setting the stage for future innovations and investment opportunities. Bridging the AI Ecosystem: Zoë shares insights from her experiences on how AI strategies vary between corporate giants and nimble startups across various fields. Emerging AI Trends: Zoë highlights the latest advancements in AI, including generative models, Deepseek, and agentic technologies, and their profound effects on the market. Learn more about 3i Members and follow us on LinkedIn for updates.

    34 min

Info

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.