The Scaling CEO

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.

In this episode, I sit down with Bernardo Hernández to break down what really changes as you scale a company, from doing everything yourself to building a team that can outperform you. We talk about why execution is the real challenge in business, how to hire the right people for each stage of growth, and why transparency through metrics is critical, especially in areas like engineering. We also explore how CEOs should think about boards, leadership evolution, and how AI is reshaping companies faster than most organizations are ready to adapt.

In this episode, I speak with Tom Ragen about one of the biggest bottlenecks for CEOs, which is waiting for perfect information before making decisions. We explore how this mindset slows down execution, how Tom learned to operate with just enough data, and why speed and adaptability matter more than certainty when scaling a company. We also discuss leadership growth, building teams that can solve problems without you, navigating acquisitions, and how to start using AI inside operations even if you’re not fully ready yet.

In this episode, I sit down with Mark Mullahy, CEO of Montgomery Place Chicago, to explore why culture is the foundation of any successful turnaround. We discuss how organizations fail when employees disconnect from the mission, why silos and lack of clarity break performance, and how leaders can rebuild alignment and trust. Mark also shares how to lead across multiple locations, adapt your leadership style, and maintain strong culture while scaling operations.

In this episode, I sit down with Michael Cherney, co-founder and CEO of Cooler Logistics, to talk about what it really takes to scale as a leader. We discuss the mistake of trying to do everything alone, why asking for help is a turning point for growth, and how building a team that challenges and supports you unlocks scale. Michael also shares insights on balancing process and flexibility, maintaining culture while growing, and using AI to improve efficiency without losing the human element.

In this episode, I sit down with John Karsant, founder of LevelUp Leads, to break down a common mistake CEOs make when scaling sales. We talk about why increasing volume without clarity leads to poor results, how most companies misunderstand their ideal customer profile, and why traction should come before scale. John also shares how to refine messaging, delegate effectively, and free up your time so you can focus on growth instead of getting stuck in operations.

In this episode, I sit down with Christopher Jane, CEO of Proper Good, to talk about what really drives scale beyond strategy and execution. We unpack why business is fundamentally about people and how many teams become too transactional through Slack and email. Christopher shares how to build culture intentionally in a remote environment, why small teams can outperform when there is real connection, and how constraints like COVID forced sharper focus and better decisions while scaling a consumer brand.

In this episode, I speak with Ryan Baird, CEO of Baird Augustine, about why resource allocation is one of the biggest challenges CEOs face. We break down how founders should think about capital, time, and people to drive growth. Ryan shares why spreading your team too thin can slow everything down. We also talk about risk, global expansion, and thinking like an investor as a CEO. We close with how AI is helping automate operations and improve efficiency.

In this episode, I sit down with Sean Hurwitz, CEO of PIXO VR, to talk about why timing is everything when it comes to scaling. We discuss the risks of raising too much capital too early and why that can hurt long term growth. Sean explains what real product market fit looks like and why many founders get it wrong. We also talk about understanding market signals and evolving as a leader over time. We wrap up with how AI is changing the way companies build and scale products.

In this episode, I speak with Skyler Badenoch, CEO of Hope for Haiti, about what it really takes to scale an organization. We break down why hiring the right people and building an aligned team is critical for growth. He shares how partnerships and funding play a key role in scaling sustainably. We also talk about leadership, culture, and creating an environment where people can do their best work. We close with how he uses AI to improve efficiency and decision making.

In this episode, I sit down with Carla Larin, CEO of maxRTE, to talk about why CEOs often become the bottleneck in their own growth. We discuss the shift from strategy to execution and what it really means to let go as a leader. Carla shares how hiring the right people and aligning incentives can unlock growth. We also get into building a sales function from zero and making better decisions over time. We close with how she is thinking about AI and staying focused on real customer problems.

In this episode, I sit down with Ganesh Padmanabhan, CEO of Autonomize AI, to talk about how AI is changing the way companies scale and compete. We discuss why having access to the same tools is no longer an advantage, and why human agency and creativity are becoming the real differentiators. Ganesh also shares lessons from scaling inside large enterprises and startups, how to think about evolving product-market fit in the age of AI, and how leaders can use AI to improve both operations and decision-making.

In this episode, I sit down with Roger Jansen, CEO of Exponential Health, to explore what really determines whether a company can execute and scale. We talk about why strategy alone is not enough, how talent is the true driver of execution, and why hiring the right people is more important than having the perfect plan. Roger also shares insights on leadership, building high-performing teams, avoiding hiring mistakes, and how CEOs can create a culture that drives performance and growth.

In this episode, I sit down with Danny Sigurdson, founder and CEO of Courier Health, to talk about what really drives successful scaling. We break down why product-market fit is the foundation of everything, how sales can sometimes hide deeper problems, and why founders need to be brutally honest about what they’re building and who it’s for. Danny also shares lessons from moving from sales leader to CEO, how to think about process at different stages, and why clarity, alignment, and communication are critical as your company grows.

In this episode, I sit down with David Simnick, CEO of Soapbox, to break down what it really takes to build and scale a company over time. We talk about why grit matters more than talent, how founders fail when they can’t take pressure, and how to build a strong team instead of trying to do everything yourself. David also shares how he evaluates entrepreneurs as an investor, the importance of humility in leadership, and how to stay focused while growing a mission-driven business in a highly competitive market.

In this episode, I speak with Mike Newman, CEO of Returnity Innovations, about the realities of turning a big idea into a scalable business. Mike explains why many CEOs fall in love with their vision but underestimate the operational discipline required to build real growth. We discuss infrastructure, partnerships with large enterprises, simplifying your business model to scale faster, and how leaders must balance innovation with operational execution.

In this episode, I speak with John Podlewski, founder and CEO of WealthyPlanet, about a hidden productivity problem inside many companies: employee financial stress. John explains how financial anxiety impacts productivity, retention, and decision-making inside organizations. We also discuss leadership lessons from his time as a military medic, building an AI-driven financial planning platform, and why CEOs must address financial wellness if they want their teams to perform at their best.

In this episode, I sit down with Neissan Monadjem, founder and CEO of LINKSPORTS, to talk about what it really takes to scale a company globally. Neissan shares lessons from building technology platforms across multiple countries and cultures. We discuss why your mission must stay rigid while your execution adapts locally, how diversity and empathy shape innovation, and why investors ultimately invest based on emotional conviction, not just spreadsheets.

In this episode, I speak with Sam Jacobs, founder and CEO of Pavilion, about the real challenges of scaling a membership business. Sam shares how raising $25M changed the way he thought about growth, status, and success, and how those shifts led to strategic mistakes inside Pavilion. We talk about hiring the right leadership team, rebuilding focus, why exclusivity matters in premium communities, and how CEOs can recognize when their organization is drifting away from its core principles.

In this episode, I sit down with Jeff Perkins, CEO of Soundstripe, to talk about what it really takes to scale from scrappy startup to high-growth company. Jeff shares why early utility players eventually need to be replaced by specialists, how to know when it’s time to let go as CEO, and why hiring the right A-players removes stress at the top. We also explore how to use AI to increase operational efficiency and protect your competitive edge.

In this episode, I talk with Matt Martin, CEO of Clockwise, about the personal side of scaling. Matt shares why your company’s daily wins and losses should not define your self-worth, and how separating the two makes the CEO role sustainable. We also explore 10x growth thinking, product market fit, experimentation speed, hiring people smarter than you, and how AI is changing product development and internal operations.

In this episode, I speak with Leigh Sevin, co-founder and CEO of Endear, about building and scaling in retail tech. Leigh explains why done is better than perfect and how early founders lose time chasing polish instead of feedback. We dive into scaling omni-channel customer experience, choosing the right buyer, building integrations that matter, hiring intentionally, and using AI internally and in product to increase sales.

In this episode, I sit down with Rajeev Kapur, CEO of 1105 Media and former Dell executive, to talk about what really causes companies to stall. Rajeev explains why many businesses fail not because they do the wrong thing, but because they keep doing the right thing for too long. We unpack how to avoid becoming the next Kodak or Blackberry, how to build resilient and transparent leadership, how to scale globally, and how to operationalize AI without overwhelming your organization. This is a masterclass in adapting before it’s too late.

In this episode, I speak with Karthik Ganesh about scaling a company from $48M to nearly $500M in revenue while staying resilient under pressure. We discuss why long-term strategies fail without adaptability, how focusing on process over outcomes drives performance, and why purpose must anchor culture. Karthik shares how personal loss reshaped his leadership philosophy, how he aligns teams around a North Star, and how AI can enhance healthcare without removing the human element.

In this episode, I talk with Sam Lewis about moving from corporate leadership to building a high-growth startup from the ground up. We discuss why momentum matters more than perfection, how to scale talent inside a startup, and how humility strengthens leadership. Sam explains how AI automates operations while freeing humans to focus on trust and client relationships. We also explore execution discipline, customer insight, and the importance of simply getting started instead of waiting for perfect conditions.

In this episode, I sit down with Mason Lin to discuss scaling a global payments infrastructure business across complex regulatory environments. We talk about staying committed to your long-term vision despite market noise, balancing customer demands with product roadmap discipline, and building a leadership team to support sustainable growth. Mason explains how resilience fuels execution, how AI increases operational efficiency, and how to scale internationally without losing strategic focus.

In this episode, I speak with Premal Shah about transitioning from technical expert to scaling CEO. We explore why leadership at scale requires leverage, not control, and how building the right team creates durable growth. Premal shares lessons on hiring, culture alignment, strategic clarity, and avoiding the trap of over-optimizing product while ignoring system integration. We also discuss operational use of AI and how data-driven healthcare innovation must fit real-world workflows.

In this episode, I speak with Gamiel Gran of Mayfield about what truly determines whether a CEO can scale. We discuss why self-awareness predicts success, how to recognize real product-market fit, and why founders pivot too broadly instead of focusing deeply. Gamiel also explains how CIOs are rebuilding the tech stack for an AI-first world—and what CEOs must do now to stay relevant.

In this episode, I speak with Canay Deniz, CEO of Ren Systems, about scaling a relationship-driven company in an AI-saturated world. We explore his transition from machine intelligence leader to CEO, how top Fortune 500 leaders manage their networks intentionally, and why AI should amplify human connection—not replace it. We also discuss culture, values, and building trust with enterprise clients over the long term.

In this episode, I sit down with Mike Stacy, CEO of ID90 Travel, to talk about scaling through survival, hypergrowth, and long-term profitability. We discuss raising $13M and learning capital discipline the hard way, why team quality determines whether growth breaks you, and how leadership style must evolve at every stage. Mike also shares how he’s using AI to accelerate development while protecting the human touch that drives a 95 NPS score.