From $5M To $50M EBITDA: Brett Hickey’s Scale Checklist For Operators
Tue Jan 27 2026
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.
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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.