Episode Summary: In this insightful episode, Alex Rawlings is joined by Brett Hickey, the CEO and founder of Star Mountain Capital. Brett shares his unique journey from humble beginnings in Northwestern Canada to leading a multi-billion-dollar asset management firm in the U.S. With deep reflections on leadership, value-based investing, building collaborative ecosystems, and what truly drives sustainable success in private markets, this is a masterclass in private equity thinking. Brett also discusses the strategic opportunities in the U.S. lower middle market, the implications of aging demographics, his risk-aligned investment strategy, and the power of culture in scaling a firm. If you're looking to understand how to build a high-performing investment organization from the ground up—and what books, frameworks, and philosophies support that—this episode is essential listening. ⏱️ Episode Highlights & Time Stamps: 00:00 – Welcome and Introduction to Brett Hickey 00:41 – Overview of Star Mountain Capital and its focus on U.S. lower-middle market private credit, secondaries, and private equity 01:12 – Key mistake PE firms make: passive asset management vs. active value creation 03:08 – Aging demographics as a key investment opportunity 04:05 – Valuation arbitrage in lower middle market businesses 05:05 – Reflections on a possible downturn: macroeconomic risks and “air pockets” 07:59 – Aging populations and structural economic concerns 09:53 – The importance of cash flow and capital protection 10:21 – Brett’s entrepreneurial journey – from launching his first fund at 26 to building Star Mountain Capital 12:41 – The S-shaped growth curve and persistence through innovation 13:40 – Brett’s data-driven approach to strategy and decision making 15:35 – Why aging demographics and inefficient markets create opportunity 17:08 – Biggest challenge in building the firm: People 19:30 – Aligning team culture and expectations through transparency and shared values 20:57 – Why Star Mountain is 100% employee-owned – benefits and challenges 22:54 – Building trust and long-term alignment through ownership 24:45 – Observations on asset management failures and strategic missteps 25:44 – What is the Collaborative Ecosystem and how it drives results at Star Mountain 27:34 – How peer networks like EO and YPO influenced the firm’s internal culture 28:31 – Leveraging insights between secondaries and direct investments 29:59 – Case studies, adjusted EBITDA, and forensic underwriting 31:18 – Using real business alignment as a differentiator in competitive deal processes 33:13 – Recommended reading: Brett’s top books and content on leadership and execution 33:41 – Never Lead Alone by Keith Ferrazzi 34:37 – Agility by Leo Tilman and General Chuck Jacoby 36:54 – Harvard Business Review and Rob Kaplan’s work on leadership 38:48 – Principles by Ray Dalio and how it influences Brett’s thinking 39:18 – A practical tip: triangulating decisions with deep experts 41:13 – Final reflections on value investing, risk management, and staying grounded 42:09 – How to get in touch with Brett and Star Mountain Capital 42:38 – Wrap-up and takeaways from Alex 🔗 Connect with Alex Rawlings on LinkedIn: https://www.linkedin.com/in/alexrawlings/ 🌐 Visit Raw Selection: www.raw-selection.com
