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

🧠 Episode Summary:
In this insightful episode, Alex Rawlings is joined by Brian Reavell, Founder of R-Squared Advisors and seasoned Private Equity Operating Partner, to dive deep into the world of go-to-market (GTM) strategies. Brian shares a comprehensive GTM playbook for PE-backed portfolio companies—spanning from due diligence and customer segmentation to talent evaluation and post-investment execution.

With over two decades of commercial leadership and consulting experience, Brian explains why private equity firms often overestimate internal talent, underestimate customer orientation, and misalign incentives—leading to missed growth targets. Packed with case studies and actionable frameworks, this episode is a goldmine for anyone looking to drive scalable and sustainable sales growth within a PE-backed environment.

⏱️ Timestamps:

00:00 – Introduction to Brian Reavell and today's GTM focus
01:26 – Common mistakes PE firms make around organic growth assumptions
03:21 – The three critical GTM pillars: Ideal Client Profile, Talent, and Segmentation
05:38 – Why talent is the most overlooked area in due diligence
08:00 – Assessing sales talent beyond resumes and black books
09:28 – Quantitative vs. qualitative approaches to evaluating salespeople
11:20 – EQ, IQ, and AQ: The key characteristics to assess in talent
13:18 – Building a GTM strategy post-investment: Process & execution
14:45 – Case Study: GTM transformation in a $4B building products distributor
16:56 – Impact of role design and customer segmentation on profitability
18:50 – $500M top-line and $100M EBITDA opportunity unlocked
20:42 – Managing change in founder-led businesses
23:07 – Overcoming resistance at field and leadership levels
24:53 – Case Study: Cultural and GTM integration in a K-12 education platform
27:43 – Creating flexible but standardized playbooks
29:35 – Assessing and top-grading sales and marketing leadership
31:02 – Succession planning and commercial leadership turnover
32:54 – What creates board-level confidence in GTM leaders
33:52 – Brian’s top reading and learning resources
35:19 – The First 90 Days, AI, and making tech an enabler
36:17 – How to connect with Brian Revelle

📚 Resources Mentioned:

• Winning Moves & Intelligent Equity by Dan Kremins
• The First 90 Days by Michael Watkins
• ChatGPT and AI tools for sales enablement and productivity

📨 Connect with Brian Reavell:
Email: brian@r-squaredadvisors.com
Company: R-Squared Advisors (not linked in transcript, assumed domain)

Raw Selection partners with Private Equity firms and their portfolio companies to secure exceptional executive talent. We focus on de-risking executive recruitment through meticulous search and selection processes, ensuring top-tier performance and long-term success.

🔗 Connect with Alex Rawlings on LinkedIn: https://www.linkedin.com/in/alexrawlings/
🌐 Visit Raw Selection: www.raw-selection.com

Guest: David Rowley, Operating Partner at Diversis Capital
Host: Alex Rawlings
Topic: Product Strategy, Artificial Intelligence, and the Evolving Role of the Operating Partner

🔍 Episode Overview:

In this episode, Alex Rawlings is joined by David Rowley, Operating Partner at Diversis Capital, to explore how private equity can drive value creation through smarter product strategies and the integration of artificial intelligence. With a career spanning back to the 1980s in software product development, David shares practical insights into aligning executive teams with PE theses, building agile innovation pods, and how AI is transforming both product development and organizational structures.

💡 Key Discussion Points:

• The Critical Role of Alignment:
  David highlights that one of the most frequent causes of failure in portfolio companies is a lack of alignment between leadership and the PE firm's investment thesis.
• Product Strategy Framework:
  Distinguishing between goals, vision, and strategy, David explains his approach to creating adaptive product strategies optimized for optionality and driven by data.
• AI’s Evolving Impact:
  David discusses how AI is reshaping product development, comparing the current inflection point to the rise of agile methodologies in the early 2000s. He introduces the concept of small, highly-focused “cocktail party” innovation pods to build and iterate rapidly.
• Scaling Innovation Across Portfolio Companies:
  He emphasizes the need for organizational models that support rapid, creative innovation while maintaining core operations—balancing “keeping the lights on” with breakthrough work.
• Grassroots AI Adoption:
  David shares how he's cultivating a culture of experimentation across Diversis’ portfolio companies, allowing individual contributors to explore AI tools, sparking internal champions and grassroots innovation.
• Avoiding AI Hype Distractions:
  With AI now included in many value creation plans, David outlines how to distinguish between superficial use cases and those that drive meaningful operational improvements.
• Leveraging CTO Experience as an Operating Partner:
  David reflects on how his hands-on CTO background across multiple sectors enhances his intuition and effectiveness in the PE world—particularly when decisions must be made before data is complete.
• Trends in the Operating Partner Role:
  From a recent operating partner forum, David notes the growing trend of more hands-on involvement from operating partners, suggesting a broader shift in private equity away from consultants and toward in-house expertise.

⏱️ Timestamps:

00:00 – Introduction to David Rowley and today’s topics
01:28 – Biggest mistake PE firms make: lack of leadership alignment
02:50 – Defining product strategy vs. goals and vision
05:10 – Key indicators for pivoting product strategy
06:32 – How AI is changing product development structures
08:55 – Traits and structure of high-performing innovation teams
10:42 – Balancing innovation pods with ongoing operations
12:31 – David’s early exposure to AI (40 years ago!)
14:52 – Deploying AI across portfolio companies
16:44 – Using AI agents in business operations
17:39 – Avoiding AI distractions and integrating AI into value creation
20:00 – Testing leadership alignment through AI transformation
21:14 – From CTO to operating partner: Lessons and intuition
23:08 – Takeaways from the Operating Partner Networking Forum
24:58 – Trend toward in-house expertise and interim CTO roles
25:51 – How to connect with David
26:20 – Wrap-up and final thoughts