Brett Hickey is the Founder and CEO of Star Mountain Capital, a multi-billion-dollar private investment firm focused on the U.S. lower middle market. Over more than two decades, Brett has built a specialized platform spanning private equity, private credit, and secondaries—backed by a clear philosophy: align incentives like owners, run strategy through probabilities, and build value where markets are fragmented and overlooked. He’s also made 500+ placements into private companies, giving him rare pattern recognition on what actually helps businesses scale.

In this conversation, Brett breaks down how to spot opportunity in big, fragmented markets, why a probability-driven approach beats certainty-driven planning, and what has to change when strategy can no longer live inside one leader’s head. If you’re a founder or operator trying to grow from “founder-led intuition” to durable scale—through structure, talent, incentives, and clear execution—this episode is a practical playbook.

Brett on LinkedIn: https://www.linkedin.com/in/bhickey/
Star Mountain Capital: https://starmountaincapital.com/

In this episode, you’ll learn:
•A checklist for identifying opportunity in fragmented markets before they’re obvious.
•What probability-driven strategy looks like in practice—and how it reshapes risk decisions.
•Why “your customer’s customer” matters for long-term durability and downside protection.
•The strategic foundations to move from $5M to $50M EBITDA: plan clarity, metrics, leadership, board, talent.
•How to design incentives and ownership so employees think like owners—at every level.

00:00 Introduction and Personal Investment Philosophy

00:36 Welcome to the Strategy at Scale Podcast

00:55 Introducing Brett Hickey and Star Mountain Capital

01:45 Brett Hickey's Career and Investment Insights

03:58 Understanding Market Opportunities and Risks

06:47 Investment Strategies and Market Analysis

10:13 The Importance of Differentiation and Competitive Advantage

19:56 Star Mountain's Unique Approach and Employee Ownership

25:36 Overcoming Challenges on Wall Street

26:44 Aligning Interests for Success

27:19 Navigating COVID-19 as a Team

28:11 Structuring Equity and Performance Metrics

30:49 Comprehensive Business Solutions

37:50 Strategic Agility and Talent Development

43:31 Resources for Entrepreneurs

46:20 Conclusion and Contact Information

Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks.

Steven Gaffney is a leadership advisor and author who helps teams perform under pressure through honest communication, change management, and practical leadership tools. Having advised leaders across Fortune 500 companies as well as government and military teams, Steven has seen firsthand that strategy doesn’t fail because teams lack intelligence—it fails because they operate in the wrong “mood,” leave critical things unsaid, and confuse facts with the stories they tell themselves about those facts. His latest book, Unconditional Power, lays out a practical framework for moving teams from reaction mode to execution mode—especially when information is incomplete and the pressure to move fast is real.

In this conversation, Steven breaks down the three morale states that determine whether teams take action or stall, why hidden disagreement is more dangerous than open conflict, and how leaders can create real alignment after debate (without requiring artificial consensus). If you’re a founder, executive, or operator responsible for guiding strategy through uncertainty and human dynamics, this episode gives you a repeatable playbook for making better decisions, faster—with your team fully committed.

👉 Learn more about Steven and connect: https://stevengaffney.com/

👉 Connect with Steven on LinkedIn: https://www.linkedin.com/in/stevengaffney/

👉 Contact for a free chapter of Unconditional Power: https://justbehonest.com

In this episode, you’ll learn:

•The three morale states—powerless, conditionally powerful, and unconditionally powerful—and how each one shapes execution.

•How to separate what you notice (facts) from what you imagine (assumptions) to prevent meetings from running on stories.

•A simple “T-chart” method to resolve disagreements quickly and move forward with clarity.

•Why “getting the unsaid said” is the fastest way to fix trust, alignment, and performance breakdowns.

•How great leaders build accountability through commitment—so teams stop complying and start owning the mission.

00:00 Introduction to Leadership and Learning

00:59 Introducing Steven Gaffney

01:19 Fundamentals of High Performing Teams

03:01 Diving into Unconditional Power

03:52 The Importance of Mood and Morale

04:25 Three Moods of Morale

07:01 Taking Action in Uncertainty

13:10 Distinguishing Facts from Stories

18:09 Leadership Gravitational Pull

21:00 Leadership Team Dynamics

22:11 The Importance of Honest Communication

23:23 Getting the Unsaid Said

25:29 Balancing Authenticity and Mission

30:54 Creating Accountability and Commitment

34:24 Scaling Leadership Principles

37:04 Connecting and Learning More

Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks and Verne Harnish of Scaling Up.

Bill George is the former CEO and Chairman of Medtronic and a longtime professor at Harvard Business School. Starting from an early conviction that leadership had to mean more than chasing titles, he helped transform Medtronic from a 4,000-person medical device maker into a 30,000-person, purpose-driven global leader. Along the way he codified a playbook for “True North” leadership that combines clear purpose, distinctive strategy, and uncompromising values.

In this conversation, Bill unpacks what authentic leadership really is (and isn’t), why purpose has to precede strategy, and how leaders actually grow as their organizations scale. If you’re a founder, executive, or intrapreneur trying to build something durable—not just profitable—this is a masterclass in aligning who you are with how you lead.

👉 Bill’s latest book, True North: Emerging Leader Edition: https://billgeorge.org/book/true-north-emerging-leader-edition
👉 Connect with Bill on LinkedIn: https://www.linkedin.com/in/williamwgeorge

In this episode, you’ll learn:
•How to use crucible moments to find your True North, deepen self-awareness, and stop “faking it to make it.”
•Why purpose and uniqueness—not “being the best”—should anchor your strategy and define how you win in the market.
•What it really takes to scale from thousands to tens of thousands of people, including upgrading your leadership bench and shifting from managing to coaching.
•How to build leadership circles and feedback systems that create psychologically safe spaces, grow authentic leaders, and keep values alive at scale.
•How to design metrics that actually matter, resist short-term gaming of the numbers, and hold your values under pressure from boards, investors, and the market.

Timestamps

00:00 Introduction to Self-Leadership
01:16 Welcome to the Strategy at Scale Podcast
01:39 Meet Bill George: Leadership Luminary
04:05 Bill George’s Leadership Journey
06:04 Defining Strategy and Purpose
11:38 Authentic Leadership Explained
23:01 The Importance of Crucibles in Leadership
29:23 Introduction to the Men’s Group
29:45 Weekly Meetings and Topics
30:11 Dealing with Illness in the Group
31:14 Personal Reflections and Values
34:56 The Importance of Metrics
42:16 Leadership and Growth
44:42 Challenges and Solutions in Leadership
49:12 The Role of Values in Leadership
53:07 Final Thoughts and Reflections

Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks and Verne Harnish of Scaling Up.