The Scaling Executive

As AI makes it easier for everyone to build products, what will actually make your company stand out? In this episode, I speak with Ezra Menaged, CEO of Hometalk, about the future of competitive advantage in the AI era. We discuss scaling from growth leader to CEO, developing executive judgment, empowering teams with AI, building data-driven businesses, and why taste and decision-making will matte...

AI is changing leadership faster than any technology before it. In this episode, I sit down with Jascha Kaykas-Wolff, CEO of Visiting Media, to discuss why executives must personally lead AI adoption instead of delegating it. We explore agile leadership, scaling from CMO to CEO, building AI-first organizations, empowering teams with AI agents, and preparing employees for the future of work. If you...

Building a successful company starts with the size of your vision. In this episode, I speak with Dan Hnatkovskyy, Co-Founder and CEO of Jome, about why ambitious goals attract better talent, investors, and customers. We also discuss lessons from multiple startups and exits, hiring exceptional people, scaling leadership, building AI-powered products, and why every executive should think bigger if t...

Most founders believe they need to reinvent everything to build a successful company. In this episode, I sit down with Travis Hedge, Co-Founder and CEO of Vouch, to discuss why that mindset can actually slow your growth. We talk about transitioning from CRO to CEO, leading through listening instead of assumptions, building strategic partnerships, scaling from startup to a $160M-backed company, and...

This article is a summary of what many different senior executives have told me about what they are doing with AI right now. As we enter July 2026, the state of AI in the executive office is defined by a striking paradox: executives are spending aggressively and taking personal control, yet most remain unable to prove clear financial returns. Roughly 72% of CEOs now identify as their company's...

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 o...

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...

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 le...

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 trans...

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...

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 constant...

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 t...

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 als...

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....

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 advis...

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 wit...

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...

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 fo...

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 shar...

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 e...

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, st...

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, co...

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 work...