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.
Mar 31, 2026•18 min•Ep. 108
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....
Mar 31, 2026•17 min•Ep. 107
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.
Mar 31, 2026•19 min•Ep. 106
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 consume...
Mar 31, 2026•21 min•Ep. 105
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.
Mar 24, 2026•22 min•Ep. 104
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.
Mar 24, 2026•22 min•Ep. 103
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.
Mar 24, 2026•23 min•Ep. 102
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....
Mar 24, 2026•19 min•Ep. 101
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 deci...
Mar 17, 2026•21 min•Ep. 100
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.
Mar 17, 2026•19 min•Ep. 99
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 communicatio...
Mar 17, 2026•23 min•Ep. 98
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 comp...
Mar 17, 2026•25 min•Ep. 97
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.
Mar 10, 2026•21 min•Ep. 96
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.
Mar 10, 2026•19 min•Ep. 95
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.
Mar 10, 2026•18 min•Ep. 94
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.
Mar 10, 2026•24 min•Ep. 93
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.
Mar 03, 2026•24 min•Ep. 92
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.
Mar 03, 2026•24 min•Ep. 91
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.
Mar 03, 2026•21 min•Ep. 90
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 mast...
Mar 03, 2026•19 min•Ep. 89
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.
Feb 25, 2026•20 min•Ep. 88
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 perfe...
Feb 25, 2026•20 min•Ep. 87
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....
Feb 25, 2026•19 min•Ep. 86
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.
Feb 25, 2026•23 min•Ep. 85
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.
Feb 17, 2026•22 min•Ep. 84
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.
Feb 17, 2026•18 min•Ep. 83
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.
Feb 17, 2026•21 min•Ep. 82
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 stakeholders, and deciding when leaders must change—or step aside—for the company to grow.
Feb 13, 2026•20 min•Ep. 81
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, building the right leadership mix, and how CEOs can modernize operations without losing momentum.
Feb 10, 2026•21 min•Ep. 80
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, building learning cultures, and operationalizing AI across engineering, finance, and leadership wo...
Feb 10, 2026•20 min•Ep. 79
