Cash generation over quick flips

Why do the best investors spend more time preparing for what can go wrong than forecasting what might go right? In this episode, I talk with Mark Sotir, President of Equity Group Investments, about what it really means to invest with an owner’s mindset. Mark shares lessons from working alongside Sam Zell for nearly two decades, why staying alive matters more than maximizing any single outcome, and how long-term capital changes behavior inside portfolio companies. We break down why protecting downside creates asymmetry, how adaptability beats prediction, and why value creation comes from operating discipline, not transaction timing.

Highlights:

• The difference between being an owner vs. a trader
• Why “the hundred-year storm happens every ten years”
• Preparing instead of predicting in volatile environments
• Staying alive as the core compounding strategy
• Why long holding periods create better outcomes than fast flips
• Cash flow discipline as risk management
• Why control enables transformation, not micromanagement
• How flexibility inside companies prevents brittleness
• Why value is created operationally, not transactionally
• The danger of rigid planning in dynamic markets

Guest Bio: Mark Sotir is the President of Equity Group Investments, the private investment firm founded by Sam Zell, where he oversees the firm’s investment portfolio and works closely with portfolio companies to improve strategy and operations. He also serves as Chair of the investment committee at Chai Trust Company, the corporate trustee for the Zell family trusts. Mark joined EGI in 2006 and has held senior leadership roles across operating companies, including as CEO of Sunburst Technology and President of Budget Group, with earlier experience at Coca-Cola. He holds an MBA from Harvard Business School and a BA from Amherst College.

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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 Capital. 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) Introduction (0:28) Owner's mindset and risk management in private equity (1:35) Adapting investment strategies and the "hundred year storm" concept (2:22) The importance of capital structure and not over-leveraging (3:42) Navigating unpredictable market changes and staying in business (6:13) Dedicated capital base and long-term value creation (11:41) Cash flow generation and disciplined investing (12:20) Control in portfolio companies and leveraging multiple strategies (16:07) Avoiding attachment and the importance of team diversity (17:34) Balancing empathy with business decisions and founder transitions (21:01) Founder readiness and adapting to company culture (24:43) Business development, CRM strategies, and succession planning (27:40) Leadership transition, trust, and optimizing operations (29:23) Sourcing deals and the evolving landscape of private equity (30:23) Closing remarks