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Strategy at Scale
Brought to you by Outthinker, Scaling Up, and Growth Institute
In a sea of contradictory business advice, Strategy at Scale breaks through the noise to deliver practical, proven strategies to predictably scale the value of your business. Each week, we interview successful entrepreneurs and business builders across industries to extract simple, high-impact strategic concepts that work. From avoiding costly missteps to executing systematic processes that fuel growth, you’ll gain lessons from the masters to scale your enterprise more effectively.
Strategy at Scale
From $5M To $50M EBITDA: Brett Hickey’s Scale Checklist For Operators
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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.
