From $5M To $50M EBITDA: Brett Hickey’s Scale Checklist For Operators

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.