Insights Behind the Deal

In this episode, Paul Olschwanger chats with Lisa Armstrong, a former banker who spent years working with private equity firms and large companies before shifting her focus to advising small and middle‑market businesses.

Lisa shares how bankers think, how private equity evaluates opportunities, and why founders often misunderstand what capital providers are actually looking for. She also breaks down her unique approach that...

In this episode, Paul Olschwanger chats with Tom Burchill, Managing Partner at Seven Point Equity Partners, for a candid conversation about buying “fixer‑uppers” in high‑growth industrial markets — and what it really takes to create long‑term value in private equity.Tom breaks down how Seven Point identifies companies that have been growing faster than the general economy, why operator quality is the rea...

In this episode, Paul Olschwanger talks with Bob Baumann, founder of The House of Baumann, about reinvention, presence, and the power of helping people step into their best selves.

Bob’s story is remarkable: he began as a truck driver with no college education, unsure of what his future might hold. Along the way, he discovered a rare gift — the ability to tell a story that moves people. That talent was unleashed thro...

In this episode, Paul talks with Steve Cockrell, CEO of Integribuilt Roofing, for a grounded and refreshingly honest conversation about leadership, humility, and the realities of building a trusted brand in one of the most competitive roofing markets in the country.
Three years ago, Steve made a pivotal decision: he bet on himself. He stepped into the CEO role at Integribuilt with a belief in his own potential — and that l...

In this episode, Paul sits down with Matt Murphy, CEO of CareGivers of America and a four‑time private‑equity–backed CEO, for a powerful conversation about leadership, purpose, and the human side of scaling a mission‑driven organization.
Home health care isn’t a typical private equity play. It’s not tied to interest‑rate cycles or market swings. It’s a heart business — one built on dignity, trust, a...

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 relentles...

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&md...

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 esse...

Insights Behind the Deal is your backstage pass to the world of private equity and alternative investing. Hosted by Trinity Investors, each episode unpacks the strategy, relationships, and real-world impact behind the deals that shape industries and communities. From real estate to operating companies, we go beyond the numbers to explore the people, principles, and perseverance that drive long-term prosperity. Whether you're an inv...