Ben Choi has spent three decades across the technology ecosystem—as a product leader, founder, and venture investor—and today serves as a senior leader at Next Legacy Partners, where he helps oversee $3.5B+ invested across premier venture capital firms and early-stage startups.

In this episode of Investing in Integrity, our host Ross Overline and Ben navigate the intersection of venture capital, philanthropy, and moral leadership. Ben shares how Next Legacy’s flagship model is designed to multiply capital—and then give it away.

From there, the conversation goes deeper than mechanics. Ben outlines the values that shaped his leadership and why generosity is often driven not by one motivation, but by the shared joy of impact beyond yourself.

Finally, Ross and Ben wrestle openly with capitalism—how it’s the best economic system ever tested at scale, it can still evolve to be even better, and what responsibility future finance leaders carry to make that a reality.

Whether you’re a student trying to define success or a senior leader shaping institutions, this episode is a masterclass in using capital with clarity, humility, and purpose.

Meet Ben Choi

Ben Choi is a Managing Partner at Next Legacy. He manages $3.5B+ in investments with premier venture capital firms and directly into early-stage startups. His venture track record includes pre-PMF investments in Marketo (acquired for $4.75B) and CourseHero (last valued at $3.6B). He previously ran product for Adobe Creative Cloud offerings and founded CoffeeTable, raising venture financing before selling the company.

Ben studied Computer Science at Harvard University and earned his MBA from Columbia Business School. He lives in Los Altos with his wife, Lydia, their three sons, and a ball python.

David Roberts spent nearly four decades in finance—starting on Wall Street in 1983 and joining Angelo Gordon in 1993, when the firm was a 15-person shop managing about $300M. By the time he left, the firm managed roughly $50B in assets, and David contributed to that growth by helping build and launch several of the firm’s businesses. After retiring, he created Sparks From Culture, a widely read Substack, which provides its nearly 9,000 readers with “weekly personal essays on wealth, status, and family from someone with generational wealth, writing with transparency.”

Our host, Ross Overline, is one of David’s readers.

In this conversation, David and Ross explore the hardest questions finance leaders rarely discuss publicly: How do you know when you have “enough”? Why does comparison keep resetting our definition of success? What are the risks of wealth concentration?

They discuss inequality, philanthropy, competing views of capitalism’s current state, and how greed often shows up as self-justification. David makes the case for generosity as a stabilizing force in society—and shares how he’s translated these beliefs into real, high-impact giving.

The episode closes with a simple but unforgettable principle: the butterfly effect—small acts of generosity can change a life more than you’ll ever know.

Meet David

David Roberts is a retired Partner of Angelo Gordon, where he joined in 1993, helping build and scale investment platforms across real estate, structured credit, and net lease. After retiring in 2022, he briefly served in public service as Senior Advisor to Maryland’s Secretary of Commerce.

In recent years, David has become a thoughtful public voice through his Substack newsletter Sparks From Culture (no payment necessary). All proceeds from paid subscriptions are donated to the Robin Hood Foundation, reflecting David and his wife Debbie’s long-standing commitment to impact-driven giving.

He holds a B.S. from The Wharton School of the University of Pennsylvania.

In this episode of the Investing in Integrity podcast, Ross Overline, CEO and Co-founder of Scholars of Finance, welcomes Stephen Philipson, Vice Chair and Head of Wealth, Corporate, Commercial, and Institutional Banking at U.S. Bank, America’s fifth-largest bank, to unpack how principled leadership shapes modern finance.

Stephen shares how embracing calculated risk, most notably during the 2009 crisis, can accelerate long-term growth when paired with disciplined downside assessment. He explains U.S. Bank’s interconnected approach to banking, where unified business lines strengthen client relationships and operational resilience. The conversation also explores why authenticity, transparency, and ethical clarity remain essential traits for leaders navigating rapid technological change. From AI’s role in enhancing, not replacing, client service to impact finance opportunities, Stephen offers a blueprint for building durable institutions grounded in purpose and integrity.

Meet Stephen Philipson

Stephen Philipson is a vice chair and head of Wealth, Corporate, Commercial and Institutional Banking (WCIB). He has been with the organization since 2009. WCIB comprises several businesses, including Asset Management and Institutional Services, Commercial Real Estate, Equipment Finance, Global Capital Markets, Global Corporate Trust, Global Fund Services, Institutional Client Group, U.S. Bancorp Impact Finance, and Wealth Management. Prior to becoming head of WCIB in 2024 and adding oversight of U.S. Bancorp Impact Finance to his responsibilities in 2025, Philipson led the Global Markets and Specialized Finance group within WCIB. Philipson has more than 20 years of financial services experience.

His past roles include working at Morgan Stanley in Global Capital Markets and then Fixed Income Trading, and at Wachovia, where he was director of the Financial Institutions Syndicate. Philipson chairs the board of governors of Isidore Newman School and serves on the boards of directors of the Foundation for the Charlotte Jewish Community. He serves on the board of directors of the Securities Industry and Financial Markets Association (SIFMA). He earned a bachelor’s degree with a double major in economics and East Asian studies from Washington and Lee University

Episode Timeline

• 00:00 Intro

• 04:40 From New Orleans to Wall Street: Stephen's Early Finance Journey

• 15:51 Joining US Bank During the 2009 Financial Crisis

• 18:26 Building a $670B Balance Sheet: Growth Strategies Across Diverse Businesses

• 22:24 Leading 16 Leaders: Management Committee Dynamics at US Bank

• 25:53 Innovation Without Recklessness: Balancing Safety and Evolution

• 28:21 AI as a Productivity Multiplier, Not a Job Eliminator

• 34:21 Impact Finance: Profitability and Purpose Working Together

• 37:08 Leadership Through Authenticity and Radical Transparency

• 39:12 Creating Unified Culture Across Capital Markets, Trust, and Real Estate

• 41:41 The Three Non-Negotiables for Next-Generation Finance Leaders

• 44:08 Rapidfire Round