The Scaling Executive

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...

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...

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...

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 dis...

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 i...

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 operat...

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...

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 protecti...

In this episode, I sit down with Sameer Ahuja to unpack the personal evolution required to scale as a founder and CEO. We talk about why early success becomes a liability, how ego quietly limits growth, and what it really means to commit to a new version of yourself. Sameer also shares insights on distribution strategy, identifying true product-market fit, scaling platforms with multiple stakehold...

In this episode, I speak with Dana McCauley about why innovation investments fail to deliver results in growing companies. We explore the tension between efficiency and modernization, how innovation debt quietly accumulates, and why many organizations buy powerful systems without the depth to use them properly. Dana also shares practical insights on industrial AI, automation in manufacturing, buil...

In this episode, I talk with Sankalp Arora about the leadership shift technical founders must make as their organizations grow. We discuss why communication replaces product as the CEO’s core job, how repetition creates alignment in complex organizations, and why ignoring human irrationality breaks scaling efforts. Sankalp also shares lessons on managing context switching, protecting mental health...

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, o...

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.

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.

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...

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.

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.

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.

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.

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 an...

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 g...

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 busin...

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 focu...

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 chas...