The Scaling CEO

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.