In this episode, Todd Platt, CEO of Hillwood Investment Properties, shares more about Hillwood's vision and strategy, his leadership style, lessons learned, commitment to service, and excitement for the future. Todd leads the firm’s investment strategy, capital procurement, and overall operations. Hillwood’s success is rooted in its long-term ownership mindset, deep capital resources, vertical integration, and relentless focus on customer service. That’s why they’ve become the go-to development partner for global leaders like Amazon, Walmart, Target, FedEx, UPS, and Home Depot.

Todd’s impact goes far beyond real estate. He’s a passionate advocate for brain health, a longtime supporter of the Center for BrainHealth in Dallas, and a recipient of their Legacy Award. He and his wife Laurie are known for their generosity and belief in lifting others, whether through mentorship, philanthropy, or quiet leadership.

In this episode, Paul Olschwanger and Dan Meader unpack the core elements of Trinity Investors’ dealmaking philosophy—from sourcing and structuring to post-close support. They explore how relationships, transparency, and strategic alignment shape every investment, whether in private equity or private real estate. Along the way, they define key terms like IRR, preferred return, capital stack, and major decision rights—giving listeners a shared language for future episodes.

[00:00:00] Introduction and Reminder of Why behind the podcast
[00:01:15] Glossary Segment featuring EBTDA, Preferred Return, Waterfall Structure, and Capital Stack (i.e. Pancakes)
[00:7:00] Transition to main conversation
[00:8:55] Deal Sourcing, Due Diligence, Management team, Profit margins, Size, Partners, and Price
[00:12:50] Assessing Affiliated Partners
[00:14:25] Performance and how to measure starting with IRR
[00:15:55] Cash-on-cash (dollar-based return)
[00:17:12] Cap Rates defined
[00:19:30] Fee structures - know the differences and at what level (deal vs investor)
[00:22:22] Governance at board, management, and employee level
[00:24:16] Carried Interest - percentage of profits upon disposition of business, performance-driven
[00:26:07] Final thoughts on why understanding terms makes a difference with sourcing, underwriting, structuring, and communication with investors
[00:28:12] Wrap-up and thinking about future episodes

In this inaugural episode of Insights Behind the Deal, host Paul Olschwanger sits down with Dan Meader, founder and Managing Partner of Trinity Investors. Together, they lay the foundation for the podcast and explore why now is the time to pull back the curtain on private equity and real estate investing. Dan reflects on Trinity’s growth from a kitchen table operation to a $7B firm, the human side of deal-making, and the essential balance of hard and soft skills in the investment process. He also shares memorable stories that highlight the importance of trust, transparency, and risk-adjusted returns in long-term value creation.

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[00:00:00] Introduction to the podcast’s mission and guest Dan Meader.

[00:01:07] Dan on starting Trinity Investors and why this podcast matters now.

[00:02:32] The importance of team-based investing and Trinity’s value creation approach.

[00:04:00] Why podcasting is a vital medium for explaining complex investment topics.

[00:05:58] Overview of Trinity’s investment focus: real estate and operating companies.

[00:08:06] Beyond the model—why soft skills matter as much as hard analysis.

[00:10:09] Relationship dynamics and people as the core of any successful deal.

[00:12:54] Trust, transparency, and red flags when buying businesses.

[00:15:46] The Trinity ecosystem and the variety of stakeholders involved.

[00:17:11] What listeners should take away from each episode: learning and confidence.

[00:18:58] The pediatrician analogy—knowing the right questions to ask.

[00:19:29] Storytelling as a tool for understanding complex financial concepts.

[00:21:11] Long-term investing lessons: diversification and liquidity.

[00:22:42] Dan’s nod to Dolores and closing thoughts on future episodes.

Links:

www.wendellrhoads.com

www.trinityinvestors.com