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.