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.

Benji Shomair is an entrepreneurial operator and investor who spent over a decade at Facebook (now Meta), where he built and scaled multiple billion-dollar global businesses across ads, messaging, and commerce. Most recently, he served as VP of Commerce Business at Meta, leading the commerce experiences team and shaping how billions of users engage with shopping on Facebook and Instagram.

Benji has had a front-row seat to the evolution of digital platforms— scaling Facebook’s ads business globally, turning messaging into a powerful sales engine, and helping brands adapt to a content-driven commerce world. Benji has been a 3i Member since 2024.

In this episode, hear about:
• How “following the customer” helped inform the development of new products and business at Facebook (now Meta) 
• How messaging became the go-to sales channel for SMBs globally
• Why content is the new storefront—and what brands must do to stay relevant

What do BlackBerry, Swiffer, Impossible Burger, Sonos, and Febreze have in common? They were all named by one man—David Placek, founder of Lexicon Branding, the agency behind more than 100 iconic brand names. Fast Company calls Lexicon “the most envied branding agency in the world.”

A 3i Member since 2024, David has spent decades naming companies—from Silicon Valley startups to global giants like Apple and Coca-Cola—craft the language that defines their brands. He also lectures on creativity at Stanford GSB and UC Berkeley Haas, advises startups, and runs River Lane Vineyard in Sonoma.

In this episode, David sits down with Mark Gerson to reveal the surprising stories behind some of the world’s most recognizable names—and why the best ideas often come from unexpected places. He explains:

• How Lexicon’s three-team system helps spark creativity through controlled chaos

• The strategy behind names like Impossible, PowerBook, and Dasani

• Why the sound of a name matters just as much as its meaning

• How risk, discomfort, and even polarization signal a name that has real power

• What entrepreneurs often get wrong when naming their company or product

A 3i Member since 2024, Ankur Bansal is the President of HomeLight Inc. He brings over a decade of experience as a founder, operator, and investor in the technology space. Ankur began his career in private equity before launching SnapSaves, a receipt-scanning cashback app that was acquired by Groupon in just 11 months. He later served as a founding executive at SnapTravel (now Super.com), where he helped scale the business from inception to over $175 million in revenue in just two years.

In this episode, Ankur talks about:
 • Lessons from building and exiting SnapSaves in under 12 months
 • Opportunities and emerging trends in proptech—and where the space is heading
 • How AI is already reshaping mortgage operations and real estate workflows
 • Why product-market fit is a spectrum—and how entrepreneurs should think about raising capital

A 3i Member since 2022, Adam H. Schwartz is a Partner and Portfolio Manager at First Manhattan, where he has worked since 2001. Adam played a pivotal role in launching the FM First China Funds in 2009—First Manhattan's China-focused investment vehicles—and regularly travels to China to collaborate on research, portfolio management, and due diligence. He holds a BA in Economics and International Relations from Brown University and an MBA from Columbia University Graduate School of Business.

First Manhattan has a deep-rooted legacy of partnership and investment alignment with Warren Buffett. Throughout his 25 years at First Manhattan, Adam has embraced and carried forward this tradition, fostering lasting relationships with Berkshire Hathaway and securing exclusive access to the Annual Shareholder Meeting on behalf of 3i members for the third consecutive year.

In this episode, Adam shares:

• Effective strategies for investing in China

• Importance of management incentives and compensation

• Long-term discipline in navigating technological disruption

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 1947-1949
• Fighting Back: Stan Andrews and the Birth of the Israeli Air Force

Documentary:

• Above and Beyond (2014 documentary featuring Craig Weiss)

Craig's Professional Links:

• Flagstaff Ventures (Craig Weiss's Venture Firm)
• Craig Weiss LinkedIn

Additional References from Conversation:

• Reason.com article covering Sen. Rockefeller’s vaping remarks
• Cast a Giant Shadow (1966 film about Mickey Marcus, mentioned in episode)

3i Members Links:

• 3i Members Official Website
• 3i Members LinkedIn

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.

Peter Boockvar is the Chief Investment Officer at The Bleakley Group and publisher of The Boock Report. He is a trusted voice in financial media, regularly contributing to CNBC. Prior to joining Bleakley, Peter was the Chief Market Analyst at The Lindsey Group, a macroeconomic and market research firm founded by former Federal Reserve Governor Larry Lindsey. Earlier in his career, he worked as a Macro Analyst and Portfolio Manager at Omega Advisors and served as an Equity Strategist and Portfolio Manager at Miller Tabak + Company. Peter has been a 3i Member since 2023.

In This Episode, Hear About:

• 2025 Market Predictions: Positioning portfolios for shifting economic cycles
• Global Opportunities: Leveraging Asia’s growing middle class and regional momentum
• The Role of Crypto: Evaluating digital assets as a hedge and growth opportunity in volatile markets

Learn more about 3i Members at 3imembers.com and follow us on LinkedIn for updates. 

Mawi Asgedom is a world-renowned speaker, bestselling author, and entrepreneur. After fleeing Ethiopia as a child and spending years in a refugee camp, Mawi overcame incredible challenges to graduate from Harvard University, where he delivered a commencement address to 30,000 people.

Driven by his passion for social-emotional learning (SEL), Mawi founded Mawi Learning in 1999, transforming education for millions and earning prestigious awards before its acquisition by ACT in 2019. In 2023, he launched Inner Heroes Universe, a groundbreaking platform empowering kids with mental health and SEL skills through innovative tools for parents and educators.

In this episode, you’ll discover:

• How Mawi’s journey from refugee to Harvard graduate shaped his resilience and entrepreneurial vision
• Lessons on grit, goal-setting, and overcoming imposter syndrome
• The impact of Inner Heroes Universe on education and youth development

Learn more about 3i Members at 3imembers.com and follow us on LinkedIn for updates. 

You can learn more about Mawi at Mawi.com and InnerHeroesUniverse.com.

Ed Newman is a Managing Director and Partner at Boston Consulting Group (BCG), where he leads the firm’s Corporate Strategy business in North America and the private equity and M&A team in the Midwest. With over a decade of experience, Ed specializes in corporate strategy, portfolio management, and shareholder value creation. He has co-authored influential reports, including “Ten Lessons from 20 Years of Value Creation Insights” and “Four Ways PE Can Accelerate Returns in Automotive.”

Listen to the episode to hear:

• Insights into effective corporate strategy and value creation

• Common pitfalls in corporate management and how to avoid them

• Advice for young professionals entering corporate America or consulting

Learn more about 3i Members and follow us on LinkedIn for updates.