Strategy at Scale

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. 

  1. JAN 27

    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.

    48 min

  2. JAN 13

    Unconditional Power: Steven Gaffney’s 3-State Framework For High-Performing Teams

    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.

    39 min

  3. 12/09/2025

    How Bill George Uses Authentic Leadership: Building Companies That Outlast Markets

    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.

    55 min

  4. 11/25/2025

    From Booking.com To WeRoad: How Andrea D’Amico Built A €100M Community

    Andrea D’Amico is the CEO of WeRoad, one of Europe’s fastest-growing travel companies, and former regional VP at Booking.com. After nearly two decades helping scale Booking.com from a 100-person startup to a 20,000-person global giant, he stepped back post-COVID to rethink what he actually wanted to build next. That reflection led him to WeRoad, now a €100M-revenue, pan-European community that has brought 300,000+ young professionals to 125+ destinations through nearly 1,000 itineraries and more than 3,000 trip coordinators. This conversation matters because Andrea bridges corporate scale and scrappy early-stage execution, showing how to design a business that doesn’t just grow, but compounds through community. For founders, operators, and intrapreneurs, his story offers a repeatable playbook for turning local, human experiences into a scalable, tech-enabled platform—without losing cultural integrity or financial discipline. Inside this conversation: Why stepping out of your corporate comfort zone can clarify the kind of company you’re wired to build—and how that self-awareness shapes every scaling decision.How WeRoad turned post-COVID loneliness and the old stigma around “group travel” into a differentiated position for solo travelers who don’t want to travel alone.The WeRoad flywheel: travelers → coordinators → travel producers → long-tail itineraries—and the tech, processes, and metrics that keep the machine scalable.The four guiding principles Andrea uses (ambition, agility, ownership, community) to hire, organize local teams, and keep six offices rowing in the same direction.A pragmatic view on fundraising: when to raise, what “smart money” really looks like, and how to choose investors who match your strategy—not just your valuation. Andrea’s journey is a reminder that durable scale comes from aligning model, community, and capital around a clear purpose—and there’s at least one flywheel decision from this episode you can apply to your own business this week. Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks.

    43 min

  5. 11/11/2025

    Scaling With Purpose, Not Capital: How Brad Stevens Built Outsource Access

    When growth gets real, strategy has to scale with it. In this conversation, we unpack a practical playbook with Brad Stevens—founder of Outsource Access—on turning constraints into capacity, and values into velocity, using a global-talent model anchored in culture, systems, and smart economics. From bootstrapping through a prior business crunch to building a Philippines-based team of full-time, benefits-backed “teammates,” Brad shares how he identified a durable opportunity, designed for retention and quality, and aligned giving and culture with the UN Sustainable Development Goals—without outside capital. In this episode, you’ll learn:  • A four-part strategy lens—Promise, Power, Process, Profit—to test opportunities and scale decisions.  • How to create real advantage (preferential inputs, scalable capabilities, and customer “captivity”) that drives pricing power.  • The two-question audit that surfaces hidden bottlenecks and converts them into high-ROI roles and workflows.  • Building “Process” the right way: org design, incentives, operating cadence, and managed offshore teams that improve retention.  • Profit discipline without external funding: pricing, unit economics, FX sensitivity—and why investing in people and tools comes first. Ultimately, this is a story about reframing work: pairing AI with global talent to free your best people for their highest and best use—and to build a company that scales on purpose. Let’s dive in with Brad Stevens. Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks.

    36 min

  6. 10/21/2025

    From Gas Station to CEO: How Shirin Behzadi Scaled a Multi-Brand Empire

    What does it take to build—and sell—a thriving business born from resilience and clarity of purpose? Few stories capture it as powerfully as Shirin Behzadi’s. At 17, Shirin fled Iran alone during the revolution, arriving in the U.S. with little money and no family. She started as a gas station cashier—and eventually rose to become CEO of Home Franchise Concepts, the parent company behind Budget Blinds and several other national home-service brands. Under her leadership, the company more than doubled in size, expanded into multiple industries, and achieved a successful private-equity sale—all while staying true to its core values and people-first culture. In this episode, you'll learn: Why adversity can become your greatest strategic advantageHow to identify your company’s true core competencyThe power of a “listening tour” to realign culture and accelerate growthHow to navigate private-equity partnerships without losing your missionWhy clarity of purpose drives both leadership and negotiation successShirin’s journey proves that grit and gratitude can scale just as powerfully as capital. Let’s dive in with Shirin Behzadi, author of The Unexpected CEO. Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks.

    53 min

  7. 10/14/2025

    Spotting a Billion-Dollar Opportunity: Radek Sali on Turning Swisse into a Global Brand

    What does it take to transform a small supplement company into a global wellness powerhouse valued at over $1 billion? Radek Sali has the answer. As CEO of Swisse Wellness, Radek led the company through one of Australia’s most remarkable growth stories—turning a niche vitamin brand into a household name through intuition, bold marketing, and a people-first culture. Where others focused on health claims, he reimagined the category through aspiration, storytelling, and purpose. Today, Radek is an investor, advisor, and advocate for conscious leadership. In this episode, you’ll learn: How to use intuition as a strategic edge in identifying real opportunitiesThe flywheel model that fueled Swisse’s explosive global growthWhy culture is the only competitive advantage that can’t be copiedHow to balance purpose, performance, and profit at scaleThe lessons every entrepreneur can apply from wellness to any industryRadek’s story is a testament to scaling with heart, clarity, and conviction. Let’s dive in with Radek Sali. Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks.

    35 min

  8. 09/23/2025

    After the Idea: Julia Austin on Building Startups That Last

    Most founders obsess over the spark of an idea—but the real test begins after the idea. Julia Austin knows this better than most. As an operator at Akamai, VMware, and DigitalOcean, an advisor to hundreds of startups, a faculty member at Harvard Business School, and now the author of After the Idea, she’s seen what truly drives sustainable growth. In this episode of Strategy at Scale, Julia challenges the “move fast and break things” mindset and offers a grounded, evidence-driven playbook for building enduring companies. She shares how to spot real product-market fit, create a culture that fuels execution, and design systems that make scaling possible. You’ll learn: Why the hardest part of entrepreneurship starts after the ideaHow to test product-market fit with scrappy, real-world experimentsThe link between clarity, culture, and long-term resilienceWhat big companies often get wrong about innovationWhy “slow down to move fast” might be the smartest strategy of allWhether you’re leading a startup or driving innovation inside a large organization, Julia’s insights will help you scale with clarity, discipline, and purpose. Thanks for listening! This episode is brought to you by Kaihan Krippendorff of Outthinker Networks.

    38 min
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About

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. 

Information

  • Creator
    Outthinker
  • Years Active
    2024 - 2026
  • Episodes
    25
  • Rating
    Clean
  • Copyright
    © 2026 Outthinker
  • Show Website
    Strategy at Scale