In this episode, I sit down with Bryan Murphy to explore why AI is a structural shift, not a feature you simply add to an existing business. We talk about moving from services-heavy models to AI-first platforms, the discipline required to stay focused as a CEO, and the personal blind spots that emerge at scale. Bryan shares lessons from scaling multiple companies, making painful contrarian bets, operationalizing AI across the organization, and building management systems that prevent leaders fro...
Feb 10, 2026•21 min•Ep. 78
In this episode, I talk with Pano Anthos of XRC Ventures about why educating the market is one of the most expensive and underestimated barriers to scale. We explore bootstrapping discipline, founder CEO transitions, AI application layers, and why distribution—not capital—is becoming the ultimate competitive advantage for startups and venture-backed companies.
Feb 04, 2026•25 min•Ep. 77
In this episode, I speak with Ted Krantz, CEO of interos.ai, about why product usage is the clearest signal of real product-market fit. We break down daily versus monthly usage, why partial PMF is dangerous, how AI is reshaping SaaS strategy, and what CEOs must prioritize when scaling beyond revenue metrics to build truly sticky, defensible companies.
Feb 04, 2026•20 min•Ep. 76
In this episode, I sit down with Brandon Colby, CEO of Sequencing.com, to unpack what it really takes to scale companies built on complex, scientific technology. We discuss why deep technical understanding at the CEO level matters, where AI truly helps versus where it fails, and how leaders avoid dangerous shortcuts when building products for consumers in highly sensitive domains like genomics and healthcare.
Feb 04, 2026•20 min•Ep. 75
In this episode, I sit with Eric Martell to break down decision discipline at scale. We talk about why saying yes too often leads to burnout, why defaulting to no kills growth, and how experienced CEOs build clear decision frameworks. We also cover pivots, capital discipline, the shift from builder to leader, and how AI is changing how modern companies operate.
Jan 27, 2026•21 min•Ep. 74
In this episode, I talk with Asad Zaman about why hiring today is harder—and riskier—than ever. We unpack the talent crunch, how AI is shrinking teams while raising the talent bar, and why CEOs must stay involved in hiring longer. We also discuss leadership decay, stage-appropriate hires, CEO energy, and how leaders scale themselves in a high-pressure environment.
Jan 27, 2026•23 min•Ep. 73
In this episode, I speak with Elias Stahl about why a company can’t outgrow its CEO. We dive into leadership maturity, building elite teams, vulnerability as a leadership tool, and how founders must scale themselves as fast as the business. We also explore AI’s role in creativity, manufacturing, and how leaders introduce new technology without breaking trust or culture.
Jan 27, 2026•21 min•Ep. 72
In this episode, I sit down with Trip Adler to explore the tension between customer feedback and CEO vision. We talk about scaling Scribd over 17 years, when listening too closely can stall innovation, and how leaders make visionary leaps when customers can’t see what’s next. We also cover culture design, delegation vs detail, and how AI is reshaping creativity, copyright, and modern companies.
Jan 27, 2026•16 min•Ep. 71
In this episode, I sit down with Greg Schott, former CEO of MuleSoft, to talk about how culture directly affects results as companies grow. We discuss how I should think about building a strong culture at scale, why talent density matters, and how my role as CEO changes as the organization becomes more complex. Greg also shares lessons from scaling an enterprise software company with discipline and focus.
Jan 20, 2026•23 min•Ep. 70
In this episode, I speak with Asher Mathew, CEO of Partnership Leaders, about why growth often breaks once companies reach the $50–80M stage. We discuss when I should start thinking seriously about partnerships, how partners create leverage beyond sales, and how to design a scalable go-to-market strategy. Asher also shares how values, operating models, and AI fit into building a company that can grow sustainably.
Jan 20, 2026•24 min•Ep. 69
In this conversation, I sit down with Kim Hansen, CEO of Cake Equity, to explore why the skills that helped me succeed early may now be limiting my growth as a leader. We talk about self-awareness, letting go of control, and how I should evolve my role as the company scales. Kim also shares how equity and incentives shape behavior and how I can use AI to support better thinking without losing focus.
Jan 20, 2026•22 min•Ep. 68
In this episode, I talk with Ben Borodach, CEO of april, about why chasing fast growth can quietly damage long-term outcomes. We discuss how I should think about building a company in a regulated environment, how to handle pressure from investors, and how to decide when patience matters more than speed. Ben also shares how he uses AI to create leverage and how a CEO’s role must change as the business matures.
Jan 20, 2026•21 min•Ep. 67
In this episode, I talk with Matt Blosl about why companies fail to scale even after hiring great executives. We explore the idea of leadership teams operating as one engine, not silos of functional excellence. Matt shares how CEOs should think about focus during scale, building alignment across product and commercial teams, managing remote organizations, and using AI deliberately rather than chasing hype. This is a deep discussion on execution, leadership design, and sustainable growth.
Jan 14, 2026•20 min•Ep. 66
In this episode, I sit down with Adam Spector to unpack why impatience quietly destroys good strategy. We talk about why founders change direction too early, how many decisions require more time and data than CEOs expect, and why execution compounds when leaders stay focused. Adam also shares hard truths about delegation, outsourcing non-core work, valuing CEO time correctly, and how AI should be used to move faster without distracting from what truly drives growth.
Jan 14, 2026•20 min•Ep. 65
In this conversation, I talk with Brett Sharenow about why most CEOs struggle to clearly explain their business and why that failure blocks both growth and capital. We break down what a compelling case for customers actually is, why investors don’t fund technical explanations, and how clarity drives revenue, valuation, and exits. Brett also shares common CEO blind spots around focus, financial models, scaling discipline, and how AI is reshaping fundraising, competitive moats, and exit planning....
Jan 14, 2026•22 min•Ep. 64
In this episode, I sit down with Ross Wainwright to talk about why AI is no longer optional for CEOs. We unpack what it really means to have an AI agenda, why moving too slowly now creates existential risk, and how leaders should think about AI beyond hype, cost cutting, or automation. Ross also explains the difference between employee experience and customer experience, why leadership vulnerability builds trust at scale, and how speed, experimentation, and breaking silos are critical advantages...
Jan 14, 2026•20 min•Ep. 63
Over the last few months, I interviewed 50 CEOs across manufacturing, logistics, SaaS, and EdTech to understand how leaders are actually using AI today. What I found is clear: the experimentation phase is over. CEOs are embedding AI directly into strategy, operations, engineering, customer support, and risk management. In this episode, I break down five real ways AI has moved from pilot to infrastructure.
Jan 12, 2026•6 min•Ep. 62
In this episode, I sit down with SC Moatti to explore how AI is redefining product management. We discuss why traditional experimentation is breaking down, how AI introduces new risks, and what CEOs must rethink when building and scaling products today.
Jan 09, 2026•20 min•Ep. 60
In this episode, I talk with Patrick Brown about why execution breaks down without measurement. We explore how CEOs can build measurable systems, scale global teams, and avoid being controlled by the business instead of controlling it.
Jan 09, 2026•18 min•Ep. 61
In this conversation, I speak with David Rabie about the moment a critical funding round collapsed with only weeks of runway left. We unpack how he managed the pressure, kept the team aligned, and turned a near-failure into a defining leadership moment.
Jan 09, 2026•17 min•Ep. 59
In this episode, I talk with Chris Jones about how cash flow—not outside funding—powered his company’s growth. We break down why starting with limited capital forced discipline, protected margins, and helped build a profitable business while others burned cash.
Jan 09, 2026•19 min•Ep. 58
In this episode of The Scaling CEO Podcast, I speak with Levi King, CEO and Chairman of Nav, about a hard truth of leadership: many problems at scale start with the CEO. We talk about self-reflection, owning mistakes, people decisions, and how leaders lose alignment when they blame others instead of looking inward. Levi also shares lessons from building multiple companies, sitting on boards, and how CEOs should think about using AI to work better without losing accountability.
Dec 22, 2025•21 min•Ep. 57
In this episode of The Scaling CEO Podcast, I speak with Carver Anderson, CEO of Suggestic and former co-founder of MindBodyGreen, about the real decisions that determine whether scaling works—or quietly fails. We talk about recognizing when a strategy is no longer right, scaling teams and leadership capacity, trusting others to take ownership, selling into large regulated enterprises, and how AI can accelerate both internal operations and customer-facing outcomes.
Dec 22, 2025•21 min•Ep. 56
In this episode, I talk with Mark Wald about the financial blind spots that show up as companies scale. Mark explains why growth puts pressure on cashflow before it shows results, how CEOs should think about the right metrics, and why poor visibility hides real performance issues. We also talk about the shift from founder to CEO, building systems that scale, and where AI actually helps in finance and operations without replacing human judgment.
Dec 22, 2025•21 min•Ep. 55
In this episode, I talk with Mehdi Daoudi about failure, leadership, and what really matters when you’re scaling a company that can’t afford downtime. Mehdi shares a mistake that took down 5,000 ad servers and explains how the response to that failure shaped how he leads teams today. We also talk about blind spots CEOs develop as they scale, why staying close to customers and hiring matters more than ever, how quality and resilience become company-wide responsibilities, and how AI is changing op...
Dec 22, 2025•20 min•Ep. 54
In this episode, I talk with Lindsey Carnett about the competitive mindset every CEO needs to scale. Lindsey shares the tough-love lessons she learned as an athlete and how they shaped her approach to beating competitors, building a stronger team, and finding blind spots in your growth strategy. We also talk about financing, data-driven marketing, and how AI is changing the way agencies operate.
Dec 15, 2025•19 min•Ep. 53
In this episode, I talk with Damon Lembi about imposter syndrome and why every CEO feels it at some point. Damon walks through his four-step process for beating it, built from his years as an athlete and CEO. We also discuss delegation, building a learning culture, developing leaders at every level, and how AI is reshaping what it means to lead today.
Dec 15, 2025•21 min•Ep. 52
In this episode, I talk with Jim Schleckser about one hard truth: most CEOs are the bottleneck in their own companies. Jim breaks down how to find the real constraint, why great CEOs delegate early, and how to shrink your to-do list so you can focus on what actually drives growth. We also talk about hiring, replacing yourself in key roles, and how AI is changing the work of every leader.
Dec 15, 2025•20 min•Ep. 51
In this episode, I talk with Simon Goodall about why your team sees problems long before you do. Simon shares how frontline insight can transform a company, how leaders create clarity during change, and why every person in an organization is a leader. We also discuss scaling yourself as a CEO and how AI is reshaping operations and customer experience.
Dec 15, 2025•19 min•Ep. 50
In this episode, I talk with Sam Hodges about what founders get wrong as they try to scale. Sam shares why many CEOs fail to grow with the company, how to shift from doing the work to building a machine that can scale, and why honest feedback is so critical. We also talk about the real impact investors have on a business and how AI is reshaping insurance and startup risk.
Dec 08, 2025•21 min•Ep. 49
