The Scaling Executive

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 ho...

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....

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...

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 compensa...

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-makin...

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 e...

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...

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 leader...

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, mainta...

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...

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 connecti...

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...

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....

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...

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 t...

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...

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, avoid...

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...

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 humi...

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 lea...

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, an...

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 in...

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, a...

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 operationa...

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 an...