What if the secret to building generational wealth isn’t finding the perfect investment—but finding the right people and holding great businesses for decades?
In this episode, I sit down with Jason Pritzker, Managing Director and Vice Chairman of The Pritzker Organization and founder of 53 Stations, to discuss the investing principles that helped shape one of America’s most successful business families. Jason shares the story of how the Pritzker family built its fortune, why long-term ownership creates power...
What if the secret to building generational wealth isn’t finding the perfect investment—but finding the right people and holding great businesses for decades?
In this episode, I sit down with Jason Pritzker, Managing Director and Vice Chairman of The Pritzker Organization and founder of 53 Stations, to discuss the investing principles that helped shape one of America’s most successful business families. Jason shares the story of how the Pritzker family built its fortune, why long-term ownership creates powerful advantages, and how partnering with exceptional leaders compounds value over time.
Highlights:
- How the Pritzker family built a multi-generational investment empire
- Why finding the right partners matters more than finding the perfect deal
- The advantages of long-term ownership versus constant buying and selling
- Lessons Jason learned transitioning from private equity to venture capital
- Why great founders matter more than investment theses
- How 53 Stations developed its venture investing strategy
- The surprising similarities and differences between PE and venture investing
- Why board structure and governance can make or break a company
- The role of customer introductions as a venture capital value-add
- How family values and upbringing shaped Jason’s investing philosophy
Guest Bio:
Jason Pritzker is Founder and Managing Partner of 53 Stations, the venture arm of The Pritzker Organization, where he also serves as Vice Chairman. Backed by an inaugural $187 million commitment, 53 Stations invests in early-stage technology companies, bringing flexibility and scale to its founder partnerships, building companies that stand the test of time.
Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at david@weisburdcapital.com.
We’d like to thank AlphaSense for sponsoring this episode!
Sponsor:
AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.
Stay Connected with David Weisburd:
X/Twitter: @dweisburd
LinkedIn: https://www.linkedin.com/in/dweisburd/
Weisburd Pierce: https://www.weisburdcapital.com/
Stay Connected with Jason Pritzker:
LinkedIn: https://www.linkedin.com/in/jasonpritzker/
Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.
Disclaimer:
This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.
(0:00) The Forgotten Decision That Built the Pritzker Fortune
(2:03) Why Picking the Right Partner Matters More Than Any Deal
(5:27) The Hidden Flaw in the Traditional Private Equity Playbook
(8:48) When Selling a Great Company Actually Makes Sense
(11:21) Why Most Family Offices Lose Money in Venture Capital
(15:14) The Private Equity Habits That Fail in Venture Investing
(18:36) Why Great Founders Matter More Than Great Markets
(21:09) The Surprising Advantage Behind 53 Stations’ Investment Strategy
(25:04) The Boardroom Mistake That Weakens Startups
(36:35) The Career Advice He Wishes He Learned a Decade Earlier
