The Scaling CEO

In this episode, I talk with Cleveland Brown, CEO and Co-Founder of Payscout, about building a culture that scales. We discuss why great leaders create environments for better decision-making, how to integrate culture during acquisitions, the importance of defining company values, fostering innovation, and how executives should think about adopting AI inside their organizations.

In this episode, I sit down with Neill Feather, CEO of Point Wild, to discuss leadership, scaling through acquisitions, and the growing impact of AI on cybersecurity. We explore how AI is changing cyber threats, what leaders should know about protecting their businesses, how to integrate acquisitions successfully, and why mentorship and continuous development remain essential as companies scale.

In this episode, I speak with Jennifer Rotner, Founder and CEO of Elite Creative, about scaling both yourself and your business. We discuss letting go as a founder, building systems that support growth, creating a thriving remote culture, and why human judgment is becoming even more valuable in the age of AI. Jennifer also shares how her company is embracing AI while keeping people at the center of every decision.

In this episode, I sit down with JR Butler, Founder and CEO of Shift Group, to explore what it really takes to build a high-performing sales organization. We discuss why the best salespeople challenge conventional thinking, how founders should transition from founder-led sales to scalable sales teams, lessons from building companies through hypergrowth, and how AI is changing the future of selling. If you're leading a growing company, this episode is packed with practical leadership and sales insights.

In this episode, I talk with Daniel Arbour, President and CEO of Oshawa Power, about leading culture change inside established organizations. We discuss transforming legacy systems, building a performance-driven culture, empowering frontline employees, managing large-scale operational change, navigating the future of energy, and preparing organizations for AI. Daniel shares practical lessons on leadership, feedback, execution, and how executives can create lasting change by challenging old assumptions.

In this episode, I sit down with Ali Wing, CEO of Oobli, to explore one of the biggest challenges leaders face as their companies grow: becoming the bottleneck. We discuss building teams that can operate without constant executive involvement, scaling through systems and frameworks, leadership growth, board governance, consumer-focused innovation, the future of food technology, and how AI is transforming organizations. Ali also shares lessons from Nike, startup leadership, and leading businesses through periods of rapid growth.

In this episode, I speak with Sriram Subramanian, CEO of Link ToAny, about the challenges of scaling a company without losing confidence in your own vision. We discuss transitioning from developer to founder, building a unique go-to-market strategy, hiring mistakes, creating your own leadership playbook, transparency with employees, and how AI is reshaping the future of commerce. Sriram shares why founders and executives sometimes need to trust their instincts instead of blindly following conventional advice.

In this episode, I sit down with Daniele Horton, Founder and CEO of Verdani Partners, to discuss what it takes to scale a business when the systems, skills, and strategies that got you here are no longer enough. We talk about building a fractional team model, scaling sustainability across thousands of properties, embracing AI, making the leap from expert to executive, and why leaders must constantly evolve if they want their organizations to keep growing. Daniele also shares her journey from architect to entrepreneur and the lessons she's learned scaling a global company.

In this episode, I sit down with David Ly, founder, chairman, and CEO of Iveda, to discuss what it takes to lead a company through more than two decades of technological change. We talk about building trust, scaling globally, communicating across cultures, why leaders must personally verify execution, and how David turned operational challenges into AI-powered innovations long before AI became a trend. This conversation is packed with lessons on leadership, accountability, resilience, and long-term growth.

In this episode, I sit down with Diana Steinhoff, President and CEO of Renaissance Life and Health Insurance Company of America. We discuss the power of asking better questions, creating psychological safety, scaling leadership without getting lost in the weeds, balancing digital transformation with empathy, and using AI to improve customer experiences while keeping humans at the center. Diana also shares how her clinical background shaped her leadership philosophy and why understanding how customers feel is critical to building great organizations.

In this episode, I sit down with Grant Bowen, founder and CEO of Peak Projects, to discuss one of the hardest transitions every founder faces: letting go. We talk about building trust in your team, scaling a service business without sacrificing quality, developing future leaders, creating repeatable processes, and using AI to improve efficiency without losing the human judgment clients depend on. Grant also shares lessons from growing Peak Projects into a nationally recognized firm serving high-profile clients across the country.

In this episode, I sit down with Jay Rosenzweig, CEO of Rosenzweig & Company, to discuss what separates scalable leaders from those who get stuck. We explore why humility, curiosity, and integrity are essential leadership traits, how CEOs should think about building leadership teams, when founders need to let go of control, and what Jay has learned from placing hundreds of executives and advising high-growth companies. We also discuss AI, talent, succession planning, and the future of leadership in a rapidly changing world.

In this episode, I sit down with Zach Papenhausen, President and CEO of Apollo Corporation. We discuss the dangers of overbuilding products, why customer research can still lead you in the wrong direction, and how CEOs can avoid falling in love with features instead of customer needs. Zach shares lessons from acquiring a company just before COVID, scaling with limited resources, balancing data with human impact, and using AI to help small businesses compete with much larger organizations.

In this episode, I sit down with Dan Turner, President and CEO of Xperigo. We explore why trust is the foundation of great leadership, how strong culture drives business performance, and why CEOs must learn to let go and empower their teams. Dan shares lessons from leading through uncertainty, overcoming imposter syndrome, building one of Canada's most admired workplace cultures, and using AI to support people without losing the human touch that customers value most.

In this episode, I sit down with Mike Winterfield, Founder and Managing Partner of Active Impact Investments. We discuss the biggest mistakes founders make when trying to scale sales, why CEOs should stay close to customers longer than they think, and how to transition from founder-led sales to a scalable sales organization. Mike also shares insights from evaluating dozens of startups, coaching founders, servant leadership, venture capital, and how AI is changing productivity, hiring, and company growth.

In this episode, I sit down with Dr. Shalabh Gupta, Founder and CEO of Unicycive Therapeutics, to discuss what it really takes to scale a company in a high-stakes industry. We talk about prioritizing when everything feels urgent, creating a culture where employees are not afraid to take risks, identifying your blind spots as a leader, and continuously upgrading yourself as a CEO. Shalabh also shares lessons from taking a biotech company public, working with investors, and using AI to accelerate growth and commercialization.

In this episode, I sit down with Bryan House, CEO of Elastic Path, to discuss scaling software companies through multiple growth stages. Bryan shares why customer success teams often outperform traditional sales teams, how leaders must let go to scale, lessons from helping build Acquia into a billion-dollar success story, and why staying close to customer problems matters more than ever. We also explore AI-driven commerce, developer adoption, open-source growth strategies, customer relationships, and how CEOs can scale themselves as their organizations grow.

In this episode, I speak with Gregory Shepard, founder of Startup Science and serial entrepreneur who has built and sold 12 companies. Greg shares what his research revealed after interviewing more than 1,200 founders, why most startups fail in the first 18 months, and how founders often build through their own lens instead of the market's reality. We discuss product-market fit, delegation, startup frameworks, founder mindset, competitive positioning, meditation, and how structure can dramatically improve a company's chances of success.

In this episode, I talk with Eric Edelson, CEO of Fireclay Tile, about scaling a craft-based business into a high-growth platform. Eric shares how his team transformed manufacturing complexity into repeatable systems, why bringing order to chaos is the key to growth, lessons from acquiring Fox Marble, and the challenges of scaling service businesses. We also discuss leadership, company culture, continuous learning, AI adoption, operational excellence, and how great businesses create structure without losing craftsmanship.

In this episode, I sit down with Ed Kopko, CEO of Bold Business and former CEO of Butler International, to discuss what it really takes to scale a company through decades of growth and change. Ed shares why CEOs struggle to find time for strategic thinking, the costly leadership mistakes he would avoid if starting again, the importance of benchmarking against the best, and how AI is reshaping workforce solutions. We also explore organizational change, leadership instincts, global scaling, and what it means to build an AI-first company in today's rapidly evolving business environment.

The signal this month is clear. The companies winning with AI have stopped running pilots and started scaling what pays. New data shows that 80% of enterprises running AI agents now report measurable return. Firms stuck on chatbots fall behind. The difference comes down to execution.This month McKinsey told CEOs to move past productivity demos and ask a harder question: how will AI change the economics of your business? IBM found that companies redesigning core functions around AI are four times more likely to hit their goals. The message to the corner office is blunt. AI is now a board-level value lever, and your P&L is where the proof lives.I host The Scaling CEO podcast. I just finished interviews with 19 leaders across industrial manufacturing, software, and private equity backed hospitality. They have settled the question of whether AI works. Now they decide faster, scale what pays, and kill what stalls. Here are the five things they do to drive ROI and protect their lead.

In this episode, I talk with Ross Meglathery, CEO of Integra Tech and former Marine Corps officer, about leadership under pressure and what CEOs get wrong when scaling companies. Ross explains why leaders fail when they refuse to acknowledge their weak spots, how military leadership shaped his approach to business, and why building trust matters more than authority. We also discuss operational discipline, company culture, AI in business operations, and how CEOs can build resilient teams during periods of rapid growth.

In this episode, I sit down with Stacey Epstein, CEO of Structured and former executive at SuccessFactors, ServiceMax, and Freshworks, to talk about the realities of scaling as a CEO. Stacey shares the leadership lessons she learned moving from CMO to CEO, why founders often neglect the areas they think they already understand, and how culture changes as companies grow fast. We also discuss AI, partner ecosystems, leadership pressure, scaling teams, and why AI should act as a thought partner, not a replacement for people.

In this episode, I talk with Steve Harmon about the hidden pressure that comes with leadership. Steve shares lessons from scaling a family business into a multi-company operation managing millions of square feet of industrial space. We discuss stress management for CEOs, leading with culture, balancing growth with people leadership, building service businesses, and how AI is increasing productivity across operations and logistics.

In this episode, I sit down with Matt Tharp to explore how great leaders actually use data. Matt explains why many teams misuse metrics to defend their opinions instead of uncovering problems. We also discuss behavioral design, product-led growth, scaling remote teams, adapting leadership styles, onboarding experiences powered by AI, and what founders can learn from building companies in rapidly changing industries.

In this episode, I talk with Ben Behzad Bayat about scaling a fast-growing engineering company and the warning signs leaders often miss. Ben explains how businesses fail the same way structures fail and how small cracks appear long before collapse. We discuss leadership under pressure, hiring through uncertainty, building systems that detect problems early, and using AI to enhance employees instead of replacing them.

In this episode, I speak with Marianne Abib-Pech about what it really takes for founders to scale. We discuss why many investors wrongly assume founders cannot evolve, how scaling can actually expand creativity instead of limiting freedom, and what separates resilient founders from the rest. Marianne also shares her perspective on industrial deep tech, leadership psychology, founder-investor dynamics, and the role of AI in decision-making and capital strategy.

In this episode, I sit down with Erik Berggren to talk about the discipline required to scale as a CEO. Erik shares lessons from elite sports, military operations, and hypergrowth companies, including how leaders burn out by focusing on the wrong battles. We discuss prioritization, resilience, scaling teams across cultures, coaching founders through growth, and how AI is reshaping operational leverage inside modern businesses.

In this episode, I sit down with Ken Jisser, founder and CEO of The Pipeline Group, to talk about what most companies are getting wrong about AI, sales growth, and scaling globally. Ken shares how he built a 500-person company across 36 countries without raising funding or taking on debt, why adaptability matters more than resources, and how CEOs should actually measure the success of AI inside their organizations. We also talk about SDR turnover, remote culture, pipeline management, and the systems that help companies scale sustainably.

In this episode, I talk with Andy Vaughn, president and CEO of Alliant International University, about leading through pressure, regulation, and organizational change. Andy shares how he helped navigate major regulatory threats, why CEOs sometimes need to personally step into difficult situations, and how relationship-building helped shape critical outcomes for his institution. We also discuss employee engagement, leadership communication, higher education, AI in organizations, and what it really takes to lead during uncertainty.

In this episode, I sit down with Steven Collens, CEO of Matter, to discuss the hidden leadership challenges that appear as companies grow. Steven explains why early employees don’t automatically share the same founder mindset, how culture can quietly drift during scaling, and why storytelling and values become critical as teams expand. We also explore healthcare innovation, startup ecosystems, AI adoption inside organizations, and how leaders can build companies people genuinely want to be part of.

In this episode, I speak with Kendall Dabaghi, co-founder and CEO of Kingdom, about building a biotechnology company from personal experience, scientific research, and real market demand. Kendall shares how his own health struggles led him into microbiome research, why founders must solve problems customers actually care about, and how he turned a scientific platform into a scalable business. We also discuss product-market fit, entrepreneurship, AI, ingredient innovation, and scaling a deep-tech company in a highly competitive industry.

In this episode, I sat down with Jeff Helfgott to discuss how CEOs should lead through change, especially during growth and acquisitions. We talked about why poor communication creates fear and resistance, and how involving people early and setting clear expectations builds trust. Jeff also shared insights on scaling teams, delegating effectively, and how to approach AI in a practical way that improves operations and empowers people without unnecessary risk.

In this episode, I spoke with Hilary Dubin about the transition from doing everything as a founder to building a scalable company. We discussed how growth starts when you replace yourself with experts, the importance of systems and clear ownership, and how to navigate leadership as a co-CEO. Hilary also shared how her team approaches AI, from internal experimentation to using data and personalization to improve their product and customer experience.

In this episode, I sat down with Doug Merritt to talk about what truly drives success when scaling a company. We explored why focusing too much on outcomes can hold you back, and how learning, curiosity, and strong feedback systems are what actually create long-term results. Doug also shared insights on building culture, aligning teams, and how leaders should think about AI, not just as a technology shift, but as a human challenge that requires adoption, learning, and discipline.

In this episode, I spoke with Kevin Hohe about what it really takes to scale a business, from letting go of doing everything yourself to building a true people-first company. We discussed how many founders tie their identity to the work, why culture must be protected at all costs, and how resilience and belief in your vision are what keep you going when things get tough. We also explored hiring, leadership, and how Kevin thinks about using AI to support people, not replace them.

In this episode, I talk with Alberto Gimeno about product market fit and one of the hardest decisions CEOs face, focus. We discuss what happens when you try to serve too many markets at once, why that slows growth, and how to identify where real demand is coming from. Alberto shares how testing multiple customer segments helped validate demand, but also created complexity, and why committing to one segment is what ultimately unlocked growth. This is a practical look at how CEOs should think about focus, ICP, and scaling.

In this episode, I sit down with Steven Monterroso to talk about one of the biggest bottlenecks in scaling a company, the CEO. We break down why operating from a daily to do list is a warning sign, and how delegation, systems, and processes are what truly enable growth. Steven shares how CEOs can stop chasing tasks, let go of perfection, and build teams that execute without constant involvement. We also discuss prioritization, operational efficiency, and how to free yourself to think strategically.

In this episode, I speak with Talbot Gee about what really changes as a company scales. We discuss why many CEOs get stuck operating in their comfort zone and how that becomes a limitation as the organization grows. Talbot explains how the role of a CEO evolves across finance, operations, sales, and strategy, and why leaders must continuously adapt. We also explore curiosity, learning from peers, and how the best CEOs keep evolving as their companies become more complex.

In this episode, I sit down with Howard Chang to unpack one of the most overlooked barriers to scaling as a CEO, ego. We talk about how early success can create blind spots, why many leaders struggle to trust people who are better than them, and how that limits growth. Howard shares lessons from failure, rebuilding, and leading multiple companies, including how to think about problems more deeply, build the right team, and shift from doing everything yourself to surrounding yourself with the right people.

In this episode, I sit down with Chris Crowe to break down how AI is reshaping organizations and leadership thinking. We discuss why blindly trusting AI outputs is dangerous, how to shift from a doing mindset to a thinking culture, and what it takes to scale operations while maintaining control. Chris also shares insights on compliance, communication, team building, and how CEOs can use AI effectively without losing critical judgment.

In this episode, I talk with Kriti Sharma about how AI is changing the way CEOs should think about building products and scaling companies. We discuss why starting with real customer problems matters more than data, how to achieve product-market fit faster, and why focusing on a few key customers allows you to solve multiple problems at once. Kriti also shares how immersive, on-the-ground building leads to better outcomes and stronger adoption.

In this episode, I speak with Joshua Gould about the real weight of being a CEO. We go deep into what changes when you take the top seat, from making decisions alone to managing a global company across 80 countries. Joshua shares lessons on handling pressure, scaling internationally, navigating complexity, and how AI is transforming operations while still requiring human judgment.

In this episode, I sit down with Chris Rolls to talk about what it really takes to scale as a CEO. We explore the shift from being hands-on to leading globally, why trying to do everything slows your company down, and how to build a leadership engine that keeps growing with the business. Chris also shares how to invest in people, manage global teams, and use AI without losing quality as you scale.

In this episode, I speak with Nathan Louer about how to scale a consumer business while staying efficient. We discuss unit economics, labor and cost management, and how scaling can create efficiencies across locations. We also talk about prioritization, how to align leadership teams, and how to focus on long term growth instead of short term noise. We also explore how AI can improve internal efficiency and how to think about digital experience without losing brand identity.

In this episode, I sit down with Darren Kimura to talk about what it really takes to scale a company. We discuss product market fit, why market feedback matters more than product vision, and how to avoid wasting time on the wrong ideas. We also cover acquisitions, cultural alignment, and how to think about scaling strategies over time. We also explore how AI can be integrated into workflows and how companies can use their own data to improve decision making.

In this episode, I talk with Tom McCarty about how to scale a SaaS company and operate more efficiently as a CEO. We discuss the shift from enterprise to startup environments, how to balance structure with flexibility in sales, and why removing obstacles for your team matters. We also break down how to use AI to eliminate repetitive work, surface insights faster, and focus on high value thinking. We also touch on workforce planning and how AI is changing how teams operate.

In this episode, I sit down with Gyner Ozgul to talk about what it takes to scale a people-first organization. We discuss how early operational experience shapes decision making, why defining integration matters during acquisitions, and how to improve pricing and efficiency without slowing growth. We also talk about leadership communication, how to balance delegation with personal connection, and why vulnerability builds trust across teams. We also explore how AI can improve workflows and customer outcomes.

In this episode, I sit down with Joseph Antoun to explore how to build a company in a completely new category while still attracting top talent. We discuss his journey from medicine to leading a global nutrition company, the concept of food as medicine, and the challenges of scaling without clear market benchmarks. Joseph explains why great people are drawn to vision and purpose, not just compensation, and how storytelling becomes a CEO’s most powerful hiring tool. We also dive into leadership growth, building mission-driven teams, and how AI is being used to drive smarter decisions across the company.

In this episode, I talk with Jim Dukhovny about what it really feels like to build something at an extreme scale, including leading a company developing a flying car. We discuss how passion removes the line between work and life, how to manage overwhelming demand with limited resources, and why leadership can look more like partnership than hierarchy. Jim also shares his thinking on decision-making, building from vision to reality, and where AI should, and should not, be used, especially in high-stakes environments where safety is critical.