Independence by Design™

What if the success you're chasing isn't the final destination, but the beginning of something more?   Watch on YouTube   This episode is the natural continuation of last week's conversation with Jean Moncrieff, the new leader of the Small Giants Community. But today, we go back to the source to get the full origin story of the Small Giants Community. I sit down with Paul Spiegelman, co-founder of...

What does it actually mean to build a company that lasts?   Watch on YouTube Not just one that grows. Not just one that sells. But one that thrives beyond the founder—because it was built with values at the core.   In this episode, I’m joined by Jean Moncrieff, an entrepreneur, coach, and the new leader of the Small Giants Community, for a conversation about identity, legacy, and the tension every...

This episode is different. No guest. No business mechanics. Just me, reading from my journal and unpacking the questions that have been driving my work, my life, and everything behind Independence by Design™.   Watch on YouTube A few questions have been front and center for me since my first memories. Why are we here? What’s the point of all this work? And how do money, time, biology, and spiritua...

Jennifer Davis is the co-founder and former CEO of Davisware, a vertical ERP platform she and her husband started at 17. Over two decades, they scaled it to $20M+ in revenue, built a team of over 200, and sold to private equity. She’s also the mother of ten kids and the author of two books, including Living Exponentially.   Watch on YouTube In this conversation, Jennifer walks us through the full...

What’s happening in the M&A market right now? Who’s buying, who’s selling, and how should owners think about timing, value, and optionality?   Watch on YouTube In this episode, I sit down with Jeff Buettner from ButcherJoseph, an investment banker who specializes in founder-led companies in the lower middle market. We unpack the current state of dealmaking for $2M to $10M EBITDA businesses and...

Most owners rely on gut instinct, advisors, or market trends to make decisions, but few stop to ask: What’s actually happening underneath the economy?   Watch on YouTube In this episode, I’m joined by Joe Brown—creator of Heresy Financial—for a macroeconomic breakdown that actually makes sense for business owners. We unpack inflation, interest rates, debt cycles, and monetary distortion in plain E...

We’ve all heard it: “Pick one thing. Focus. Go all in.” But what if that advice doesn’t apply once you’ve built real optionality?     Watch on YouTube In this episode, I’m joined by Mark Cleveland—an experienced entrepreneur, investor, and self-described parallel entrepreneur—to rethink how owners can design the next chapter of life. Instead of scaling endlessly or exiting just to feel free, Mark...

If you're running a mid-sized company and considering acquisitions—or you just want to understand how smaller companies get valued—this episode is for you.   Watch on YouTube I sat down with Clint Fiore, a business broker who’s helped hundreds of Main Street businesses try to sell. And here’s the truth: most of them don’t get what they want. Not because their business is bad—but because it’s not b...

You’ve probably heard that business valuation is more art than science. But what if the art is just smoke and mirrors—and the science has been hiding in plain sight all along?   Watch on YouTube In this episode, I’m joined by Graham Stephen and Kyle McCulloch, the team behind Bizval, a company that’s quietly building a tool that may completely disrupt how business owners understand valuation. What...

What happens when the business you built no longer protects you from the parts of yourself you've been avoiding? Alex McClafferty co-founded and sold WP Curve to GoDaddy—but it wasn’t until after the exit that he found himself face-to-face with an identity crisis, emotional collapse, and a brutal confrontation with his shadow self.   Watch on YouTube In this raw and wide-ranging conversation, we t...

What really happens when an entrepreneur sells their business? For John Rood, it was the start of a deeply personal reckoning with identity, purpose, risk, and time. In this episode, we go beyond the typical exit story and talk about what it actually feels like to step away from the company you built—and what comes next when you’re no longer busy, no longer needed, and no longer sure what’s next....

This episode is fire. Elliott Holland is a straight shooter who has seen hundreds of deals from every angle—searcher, investor, operator, and QofE provider. In this conversation, we cut through the noise to talk about what’s really going on in the acquisition market, why most self-funded searchers fail, and how owners can actually position their business (and themselves) for the next chapter.   Wa...

Most business owners are exhausted by marketing that feels like a black box—random tactics, disconnected agencies, and no clear ROI. Kim Clark knows that pain—and she’s built the solution. As the former head of sales and marketing at ITR Economics, Kim helped transform the business from a founder-led consulting firm into a scalable company that exited at eight figures—without relying on Brian or A...

This episode sets the bar. Pat Hobby, my former business partner, is one of the best CFOs I’ve ever worked with. He’s not just a CPA or an operator—he brings an investor mindset and decades of experience managing financials with the purpose of building long-term value. In this conversation, we break down exactly what a business owner should expect from a high-performing CFO—and why most don’t even...

Many owner-operators begin their journey driven by the vision of personal and financial independence, only to find themselves entrenched in the daily operations, unable to step away without fear of chaos. In this episode, I talk with Rob Dube, co-founder of ImageOne and visionary behind The 10 Disciplines for Managing and Maximizing Your Energy™, about how to break free from the owner-operator tra...

Today I'm talking with Shannon Susko, a serial entrepreneur who developed the 3HAG (3-Year Highly Achievable Goal) and Metronomics frameworks. What sets Shannon's approach apart is how directly it connects your strategic plan and execution rhythms to clear, measurable financial outcomes. It's an operating system built specifically for business owners who understand their numbers but want greater c...

SBA loans have always been a key tool for financing business acquisitions, but recent changes have opened up new opportunities for both buyers and sellers. If you're thinking about selling your business, acquiring one, or financing a transition, these updates could have a major impact on your strategy.   Watch on YouTube In this episode, I sit down with John Thwing ("The SBA Guy") from Live Oak Ba...

The economy is shifting fast, and if you’re a middle-market business owner, the moves you make today will define your future—whether that’s navigating capital markets, securing financing, or making critical reinvestment decisions.   Watch on YouTube In this Quarterly Economic & M&A Update, I bring together three powerhouse guests to give you real-time insights you won’t find in mainstream...

Scaling a business isn’t just about increasing revenue—it’s about building the right leadership team to support that growth. Too often, business owners get stuck because their team isn’t structured for the future, leaving them to fill the gaps instead of leading strategically.   Watch on YouTube In this episode, I sit down with Rick Rittmaster and Mike Frommelt to break down how to design a future...

More revenue, more employees, and more complexity can actually pull you deeper into the day-to-day grind—unless your business is structured the right way.     Watch on YouTube In this episode, I sit down with Nick Bradley, a business growth strategist and private equity veteran who has worked on billion-dollar deals and now helps business owners scale with purpose. We dive into the hidden traps of...

Many business owners dream of building a company that thrives without them, but few understand what it takes to make that a reality—especially when facing a leadership crisis. In this episode, I sit down with Heather Braimbridge-Cox, CEO of Windings, and Bill Mills, founder of The Leadership Process™, to break down how to transform a struggling culture, develop high-performing teams, and turn an E...

I’ve spent the last handful of episodes diving deep into business valuations, M&A jargon, and how buyers think about value. But here’s the thing—most of it doesn’t matter unless you actually have cash left over at the end of the day.     Watch on YouTube That’s why I brought Patrick Donohue back on the show. He and I have been in the trenches, working with owner-operators who are juggling cash...

Most business owners go through a pivotal moment—their first real look behind the curtain at how buyers value companies. For Rens Hayes, that moment came when he went through a sale and due diligence process for his father’s structural steel business. What he learned from that experience completely changed how he approached building and scaling his own company, H&O Structural Engineering.   Wa...

In a world full of business jargon and complicated metrics, free cash flow stands out as the foundation of value creation for both owner-operators and investors. kXVm3nQBij8   Watch on YouTube Ken Sanginario returns to focus on this core principle, unpacking the noise around financial metrics and zeroing in on sustainable free cash flow—cash available after debt, taxes, and working capital. Togeth...

Most business owners focus on the offer price when selling their business—but the deal structure is what ultimately determines how much you walk away with, when you get it, and how much risk you take on.     Watch on YouTube In this episode of Independence by Design™, I sit down with Dave Diehl, CEO of Prairie Capital Advisors, to demystify the complex world of deal structures. Dave walks us throu...