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Strategy at Scale

Strategy at Scale

Written by: Outthinker
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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.

© 2026 Outthinker
Economics Leadership Management & Leadership
Episodes
  • Why Copying Winners Fails: Dwayne J. Clark on Finding Real Business Edges
    Mar 31 2026

    Dwayne J. Clark is the founder of Áegis Living, known for building a hospitality-first approach to senior care and a culture-led operating system. In this conversation, he shares the “black box” method he used to turn rejected ideas into real differentiation—and how purpose, community, and people practices became his growth engine.

    This episode is a practical playbook for leaders who want durable scale: how to hire your weaknesses, build a tribe, and codify culture into repeatable systems.

    In this episode, you’ll learn:
    •Why “embracing failure” is a strategy advantage—and how to mine it for opportunity
    •The “black box” process for testing ideas and finding true points of difference
    •How to build culture as retention, brand, and execution leverage
    •What it takes to hire your weaknesses (and when ownership backfires)
    •How to lead with head, heart, and guts—situationally

    Dwayne J. Clark: https://dwaynejclark.com
    Áegis Living: https://www.aegisliving.com
    LinkedIn: https://www.linkedin.com/in/dwaynejclark

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


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    51 mins
  • From $5M To $50M EBITDA: Brett Hickey’s Scale Checklist For Operators
    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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    48 mins
  • Unconditional Power: Steven Gaffney’s 3-State Framework For High-Performing Teams
    Jan 13 2026

    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.


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    39 mins
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