Most companies say “people are our most important asset,” but few can prove it. Tom Alexander is trying to change that.

As co-founder and CEO of Holistic, Tom is building tools to help companies actually understand and improve the employee experience. Not with vague platitudes, but with measurable, actionable data. In this episode, we dig into what’s really changed since the early days of Holistic, how the modern employee mindset has evolved, and why transparency isn't just a buzzword. It's a survival strategy.

From his time shaping ecosystems at 1871 to building a company rooted in operational rigor, Tom shares what founders still get wrong about culture, how to build alignment before tension erupts, and why playing your hand face up is now the only winning move.

Here’s what stood out:

Entrepreneurship Isn’t Personal. Until It Is.
Seven years in, Tom admits the emotional intensity hasn’t dulled. Every client loss, every critique, still stings. Why? Because when you believe your product genuinely helps people, rejection feels like something deeper. The real challenge is learning how to care deeply without taking everything personally.

Employee Experience Is No Longer Just Perks
Today’s employees want impact, clarity, and to feel part of a mission that matters. But here’s the catch. That mission has to be real. Holistic’s approach is about building cultures that don't rely on surface-level benefits, but instead align expectations, actions, and outcomes.

AI Might Undermine Loyalty. But It Can Also Rebuild It.
In a world where employee tenures are shrinking and layoffs are data driven, Holistic is using predictive tools to help leaders intervene before people walk out the door. Loyalty, Tom argues, isn’t dead. But the companies that want it back will need to earn it differently.

This episode is a must listen for leaders navigating culture in a hybrid world, and for founders wondering what culture really means when the rubber hits the road.

John Moakley has spent decades building, running, and investing in data-driven companies—long before “data science” had a name. In this conversation, John joins Mike and Corey to pull back the curtain on what private equity really looks for, how companies often miss the value sitting right in front of them, and why the current hype around AI mirrors the early days of data monetization.

From turning a magazine subscription list into a revenue stream, to helping scale a $70M data business, to earning the nickname Dr. No inside a private equity firm, John shares lessons from both the operating and investing sides of the table.

This episode is about more than data. It’s about pattern recognition, strategic pivots, and the often-overlooked cultural cost of change. And yes, we finally go remote for the first time because when the guest is this good, we don’t let geography get in the way.

What does a board member really look for in a CEO? What signals competence, and what quietly erodes confidence?

In this episode, Mike and Corey sit down with returning guest Ira Weiss—educator, investor, and longtime board member—to decode the often-misunderstood relationship between boards and founding teams. Drawing from over 60 investments and hundreds of founder interactions, Ira shares how he evaluates early-stage CEOs, the underrated power of persistence and curiosity, and the true markers of success (spoiler: it’s not always the outcome).

They dive into:

• How founders can turn board meetings into strategic assets
• When and why boards start thinking about leadership changes
• The real reason investors push for independent board members
• Why transparency—especially from the C-suite—is a signal, not a vulnerability

Whether you're raising your first round or leading a growth-stage company, this episode is a practical guide to working with your board, not just reporting to them.

Anar Isman didn’t start Ageless RX to build a business—he started it to challenge one of humanity’s most accepted limitations: aging. What began as personal curiosity turned into a mission-driven company now generating over $70 million in annual revenue.

In this conversation, Anar joins Mike and Corey to unpack how he built Ageless RX from a late-night side project into a fast-growing, telemedicine-powered platform at the center of the longevity movement. He shares how COVID unlocked the company’s early traction, how off-label science meets mainstream demand, and why he still interviews every hire to protect the culture.

We also get into customer listening, red tape, and what it takes to scale a direct-to-consumer health company in one of the most regulated and misunderstood categories in the market.

From a farm town in Ohio to penthouse events with billionaires in Chicago—Andrew Gunderman’s journey is anything but ordinary. By his early twenties, he had already founded and sold a startup, built founder communities from scratch, and begun curating some of the city’s most exclusive circles of entrepreneurs, investors, and influencers.

In this conversation, Andrew joins Mike Shannon and Corey Ferengul to unpack the strategy behind building Renowned Chicago, why exclusivity works when it’s paired with openness, and how relationships—not just capital—can accelerate a founder’s trajectory. He shares how aggressive outreach, mentorship, and an obsession with learning shaped his path, and why he believes networks can be one of the most valuable assets an entrepreneur can build.

We also dive into the evolving world of creators and influencers, the hidden leverage in connecting siloed communities, and how AI is already beginning to reshape how networks form.

If you’ve ever wondered how to break into circles that feel closed off—or how to turn relationships into real opportunities—Andrew’s story offers a playbook worth studying.

Uncertainty isn’t just a buzzword -- it’s basically the operating environment for every leader in 2025. From economic volatility to the unknowns of AI’s impact, executives are navigating conditions where the variables outside their control keep multiplying. In this episode, Mike and Corey break down how to lead through the fog—identifying what’s controllable, building flexible plans for the uncontrollable, and creating the right communication cadence with boards, teams, and customers. They share real-world stories of pandemic playbooks, financial “break points,” and unpopular calls that paid off. The takeaway: leading in uncertainty isn’t about having all the answers; it’s about knowing when to decide, what levers you can pull, and how to keep trust intact when the stakes are high.

Arnav Dalmia didn’t set out to build a fitness brand for older adults—but listening to customers led him there. In this conversation, Arnav joins us to unpack the unlikely evolution of Cubii, the company he co-founded that sold for north of $100 million after a decade-long grind that began with Kickstarter and a desk pedal idea.

They dig into why early investors passed, what everyone got wrong about the market, and how a hard-earned product-market fit with seniors turned Cubii into a category-defining brand. Arnav shares the inflection points that changed the company’s course: from bootstrapping out of necessity, to embedding customer feedback into the culture, to resisting the temptation to scale too soon.

If you’ve ever wondered when to pivot, how to listen better, or what lean actually looks like in practice—this one’s a blueprint.

In this episode, Corey and Mike dive deep into one of the defining trends shaping AI’s next chapter: verticalization. They explore why general-purpose AI isn’t enough—and how the most compelling solutions are now being purpose-built for specific industries, starting with Mike’s own experience building an AI operating system for independent financial advisors.

The conversation traces the journey from general tools to tailored workflows, covering:

• How to choose the right vertical by listening for signal, not just scale
• Why true differentiation lies in domain depth, not just technical features
• And how trust, service, and context are shaping the future of human-in-the-loop AI

From relationship managers to compliance nuance, they unpack why vertical-focused AI is creating a new class of companies—ones that feel more like high-leverage service partners than classic SaaS. Whether you’re building, buying, or just trying to keep up, this is the blueprint for what’s next.