E118: Loyola University's $1.2 Billion Edge

In this episode of How I Invest, we’re joined by Michael Kakenmaster, Director of Investments at Loyola University Chicago. Michael shares his journey and expertise in managing university endowment portfolios, with a focus on private markets and hedge fund strategies. He offers valuable insights on how to build sustainable, diversified portfolios and the strategies that have led to success in his role. We also discuss the evolving landscape of venture capital and how institutions like Loyola are adapting to market changes.

E117: What Will Family Offices Invest into in 2025? w/Hansen Ringer

Hansen Ringer, Managing Director at Sepio Capital sits down with David Weisburd to discuss the asset class that delivers equity-like returns without the market risk, what distressed credit reveals about market cycles and investor behavior, and what happens when stocks and bonds move together.

E116: How Everyday Investors can Access Private Equity w/Pantheon ($70B AUM)

Victor Mayer, Managing Director, Head of Private Wealth at Pantheon sits down with David Weisburd to discuss why top GPs are rushing to evergreen funds, how Pantheon balances small-cap potential and large-cap stability, and the benefits of Pantheon’s no-cost co-investment deals.

E115: Is the 60/40 Portfolio Outdated? w/James Langer

James Langer, Chief Executive Officer and Chief Investment Officer at Redmont Wealth Advisors sits down with David Weisburd to discuss how Reason small cap stocks are crushing large caps, the academic approach to outperforming with small cap strategies, and the history of top stocks since 1926.

E114: Brockenbrough $4.3 Billion Investment Edge

Chris Dion, Co-Chief Investment Officer and Managing Partner at Brockenbrough sits down with David Weisburd to discuss what makes small buyout funds resilient, how small buyouts outperform big private equity deals, and why the deal leader matters more than the firm.

E113: Christopher Zook: Playing to Win - Lessons Learned from Scaling CAZ Investments to $8B and Building a Winning Culture

Christopher Zook, Founder, Chairman, & Chief Investment Officer at CAZ Investments sits down with David Weisburd to discuss the cost of keeping the wrong person on the team, the crucial mistake CEOs make when building a strong culture, and the secret behind faster growth and success.

E112: Jake Paul: How to Build a Multi-Billion Dollar Startup

Jake Paul and Joey Levy, Co-Founders of Betr, sits down with David Weisburd to discuss Jake Paul’s bold vision for the future of sports betting and how the company seeks to become the market leader in the space.

E111: KFF’s (Kaiser Family Foundation) CIO on their $700 Million Venture Capital Edge

Dean Duchak, Chief Investment Officer at KFF sits down with David Weisburd to discuss the lessons learned from 13 years at KFF, how to create a culture of collaboration in endowments, and Dean’s perspective on diversifying investment strategies.

E110: How Legacy Knight Scaled $1.5 Billion in Under 5 Years

David Sawyer, Chief Operating Officer & Managing Partner at Legacy Knight : Multi-Family Office sits down with David Weisburd to discuss the top mistakes investors make in GP stakes, why middle-market GP stakes could be a game-changer for investors, and how GP stakes outperform traditional investments in 2024.

E109: Top Tier Capital Partners ($7B+ AUM) - Lessons Learned from Investing in 450 Funds

Ben Challgren, Principal at Top Tier Capital Partners sits down with David Weisburd to discuss what makes a top-performing fund, the surprising role of local managers in European venture success and the secrets to spotting a winning startup before it’s big.

E108: What is the Future of Venture Capital? w/Charles Hudson

Charles Hudson, Managing Partner at Precursor Ventures sits down with David Weisburd to discuss how to support first-time fund managers, innovative strategies for sourcing deals in venture capital and tips for success on building relationships with limited partners.

E107: Caltech’s CIO’s $4.6 Billion Investment Strategy

Scott Richland, Chief Investment Officer at Caltech sits down with David Weisburd to discuss key portfolio secrets inside Caltech’s $4.5B endowment strategy, the importance of strategy discipline in asset management and how direct investments are chosen behind Caltech's opportunistic bucket.

E106: How Pantheon ($60B) Invests Globally

Kunal Sood, Managing Director at Pantheon sits down with David Weisburd to discuss how US institutional investors can access Indian venture capital and private equity, key trends shaping India's unicorn startup ecosystem for global investors and how to leverage local expertise to navigate asia-pacific private markets.

E105: Ryan Serhant: How Successful Entrepreneurs Manage Time (1,000 Minute Rule)

David Weisburd speaks with Ryan Serhant, founder and CEO of Serhant, about the explosive growth following the Netflix debut of *Owning Manhattan*. They discuss how the show has transformed the business, increasing market diversification, website traffic, and lead engagement. Ryan also shares his insights on scaling a real estate business, the importance of culture in a distributed workforce, and why he sees Serhant as more than a brokerage—defining it as a sales as a service company with an innovative approach to training and technology. Throughout the conversation, Ryan reflects on his personal journey, the challenges of transitioning from broker to CEO, and the responsibility of building a brand tied to his own name.

E104: How to Start a Single Family Office w/Justinas Milašauskas

Justinas Milašauskas, Investment Manager at Willgrow sits down with David Weisburd to discuss the risks and rewards of investing in spinouts, top lessons learned from investing in venture and private markets and lessons on investing in emerging managers and navigating fragmented markets.

E103: Alex Hormozi - Private Equity’s Next Billionaire?

Alex Hormozi, entrepreneur and founder of Acquisition.com, joins David Weisburd to share his journey of building a $150 million net worth. He discusses the lessons learned from losing his fortune twice, the importance of controlling revenue streams, strategic risk-taking in business, insights into scaling businesses, and the mindset required for long-term success. Hormozi also explains how he leverages his social media presence to drive deal flow and growth for Acquisition.com.

E102: Interview w/Kellogg School of Business Dean

Francesca Cornelli, Dean at Northwestern University - Kellogg School of Management sits down with David Weisburd to discuss how private equity firms handle CEO turnover, why private equity firms benefit from enlightened disagreement and diverse opinions, and the importance of mentorship in private equity.

E101: Lessons from University of Texas ($70B) and Stanford Endowment ($40B)

Mark Shoberg, CIO & Partner at Capital Creek Partners sits down with David Weisburd to discuss the keys to successful institutional investing, how large should an endowment be for optimal returns, and how to build the perfect investment platform for family offices and endowments.

E100: CIO of $2.9 Billion University of Illinois Endowment

Travis Shore, CIO at University of Illinois Foundation sits down with David Weisburd to discuss how CIOs can adapt to the next big change in time, the critical mistakes made in mastering risk in uncertain markets, and identifying which strategy may save your endowment in the next crisis.

E99: How to Pick Top Decile Venture GP’s

Albert Azout, Managing Partner at Level Ventures sits down with David Weisburd to discuss how to spot unicorn founders early in Venture Capital, what separates great fund managers from the rest, and digging deep into the role of data in unpacking venture fund performance.