Independence by Design™

If you’re trying to grow your business without creating a mess of misaligned incentives, resentment, or comp plans that backfire—this episode is for you. I brought Jennifer Davis back on because she built one of the most intentional compensation systems I’ve ever seen. We walk through how she tied her company’s mission and KPIs directly to each person’s comp—and connected it all the way down to their personal goals. We talk about cleaning up old promises, removing politics, and building a system that creates momentum instead of confusion. It’s tactical, practical, and deeply aligned with what we talk about in Independence by Design™—because comp is strategy. And when you get it right, everything gets easier. 

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Jennifer Davis is the co-founder and former CEO of Davisware, a bootstrapped ERP platform scaled to over $20M in revenue and sold to private equity. She’s a tech entrepreneur, mom of 10, and author of two books including Living Exponentially. Now through her new venture BExponential, she helps growth-minded women lead with clarity and purpose. Her story blends grit, systems thinking, and a deep commitment to impact. 

Chapters:  

Resources: 
Jennifer's site: jenniferleedavis.com (consulting/retreats/book). 

BExponential: bexponential.com (women's leadership). 

Davisware: davisware.com (former ERP company). 

Ryan Tansom Website https://ryantansom.com/

What if the success you're chasing isn't the final destination, but the beginning of something more? 

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Most business owners I talk to know AI matters—but many are still stuck thinking it’s just for writing emails or something their IT team should handle. That’s not the game we’re playing.  

In this episode, I sat down with Geoff Woods to talk about what it really means to become an AI-driven leader. We’re not talking about automation—we’re talking about thinking. Geoff and I break down how AI becomes your most powerful thought partner once you’re clear on your goals, your constraints, and your role as the owner. If you’ve been wondering how to actually integrate AI into your business at a strategic level, this conversation is for you. 

We covered everything from the CRIT prompting framework to building executive-level AI boards, why most people struggle to think clearly, and how the education system trained creativity out of us. I also share how I’m using AI with my clients to build strategic plans, model out deals, and clarify ownership goals faster than ever before. 

This episode is for the owner who wants to stay ahead—who’s ready to think bigger, make better decisions, and design a business that works without them. 
 
Geoff Woods is the author of The AI-Driven Leader and the founder of AI Leadership. He previously co-founded the company behind The ONE Thing and served as Chief Growth Officer at Jindal Steel, where he helped grow its market cap from $750M to over $12B. Geoff teaches CEOs how to use AI as a strategic thought partner—not a task robot—so they can lead more effectively, make smarter decisions, and build companies that thrive in an AI-driven future. His frameworks, including CRIT and the AI Empowerment Curve, are helping leaders around the world operationalize AI from the boardroom to the frontlines. 

 
Chapters:  

Resources: 
The AI-Driven Leader by Geoff Woods  
AILeadership.com  
Ryan Tansom Website https://ryantansom.com/

What if the success you're chasing isn't the final destination, but the beginning of something more? 

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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 Small Giants Community, to trace the full arc of a founder's journey: from building and selling BerylHealth to scaling a culture-first company within a public firm, to co-creating the Small Giants movement that has helped thousands of values-driven leaders build something that lasts. 

What ties all of Paul's chapters together, from Beryl to Small Giants to Kintsugi Village, is a deep commitment to clarity, purpose, and process. 

This isn't just a conversation about business, it's about designing a life that means something. 

We talk about how values in a company often show up before we have the words for them, how the discipline of reflection creates repeatability, and how purpose, when acted on over time, turns into legacy. 
 
Paul Spiegelman is the co-founder of Kintsugi Village and the Small Giants Community, and the former founder and CEO of BerylHealth. He also served as Chief Culture Officer at Stericycle, where he brought his people-first approach to a publicly traded company. 

Paul is a New York Times best-selling author, Ernst & Young Entrepreneur of the Year, and a recognized voice on leadership, corporate culture, and values-driven business. His insights have been featured in the Wall Street Journal, Forbes, and Inc. Magazine. What sets Paul apart is his ability to live out what most leaders only talk about—building companies that align with values, operationalize culture, and last beyond the founder. Today, through Small Giants and Kintsugi Village, he helps steward a new generation of entrepreneurs who want to build with purpose—and chase something more than just growth. 

Chapters:  

Resources: 
Small Giants Community https://www.smallgiants.org 
Small Giants by Bo Burlingham https://www.amazon.com/Small-Giants-Companies-Instead-10th-Anniversary/dp/014310960X 
www.paulspiegelman.com 

What does it actually mean to build a company that lasts? 

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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 owner eventually faces: when and how to let go. 

We unpack the deeper reason Small Giants exists: to support leaders who want to build purpose-driven companies where people thrive, cultures endure, and success isn’t just measured by size. We also talk about what it means to scale values, not just revenue—and why Jean is uniquely positioned to carry this movement forward. 

Whether you’re in the thick of operations or starting to imagine your next chapter, this episode will help you re-anchor to what matters most—and show you that you’re not alone in the process. 
 
Jean Moncrieff is an entrepreneur, coach, and the current leader of the Small Giants Community—a global network of values-driven founders committed to building purpose-first businesses that prioritize people, culture, and long-term impact. Jean’s own journey includes founding, scaling, and exiting multiple 7- and 8-figure companies across Europe and South Africa. But what defines his work today is helping leaders clarify their vision, let go with intention, and grow companies that outlast them—not just operationally, but culturally and philosophically. Based in Zurich, Jean splits his time between Europe, the U.S., and South Africa, where he continues to coach CEOs, foster authentic community, and guide the next chapter of Small Giants with the same values that made it what it is. 

 
Chapters:  

Resources: 
Small Giants Community https://www.smallgiants.org/ 
Small Giants by Bo Burlingham https://www.amazon.com/Small-Giants-Companies-Instead-10th-Anniversary/dp/014310960X 
Jean Moncrieff on LinkedIn https://www.linkedin.com/in/jeanmoncrieff/ 
Ryan Tansom Website: https://ryantansom.com/ 
 

Sound Bites 

“At some point, every founder faces this question: how do I let go without losing what made this special?” 

“The heart of a Small Giant isn’t the founder—it’s the values that shape the culture long after they’re gone.” 

“We’re not trying to be big for the sake of it. We’re trying to be great, so the company—and the people in it—can thrive without us.” 

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™. 

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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 spirituality all fit together? If you’ve ever wondered why I care so much about alignment, ownership, and how we spend our time, this is the foundation. This is the throughline behind the Playbook, the coaching, the podcast… all of it. I talk about: 

If you’re on your own journey of trying to make your life and business make sense, this episode is for you. It’s not doctrine. It’s not advice. It’s a flashlight into the questions I’ve been living through. 

Chapters:  

Resources: 
 
Ryan Tansom Website: https://ryantansom.com/

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. 

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In this conversation, Jennifer walks us through the full arc of building, leading, and eventually stepping away from a company she built from the ground up. We talk about the early growth years, the identity shift from founder to CEO, what she learned inside private equity, and how she’s now designing her next chapter with clarity and intention. 
 
Jennifer Davis is the co-founder and former CEO of Davisware, a bootstrapped ERP platform scaled to over $20M in revenue and sold to private equity. She’s a tech entrepreneur, mom of 10, and author of two books, including Living Exponentially. Now, through her new venture BExponential, she helps growth-minded women lead with clarity and purpose. Her story blends grit, systems thinking, and a deep commitment to impact. 
 
Chapters:  

Resources: 
Jennifer Davis: https://www.itsjenniferdavis.com/ 
Davisware: https://www.davisware.com 
Ryan Tansom Website: https://ryantansom.com/ 
 

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? 

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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 talk candidly about what’s really driving—or stalling—transactions in today’s environment.  

We cover everything from deal structure, buyer behavior, and interest rate dynamics to why some owners are stuck in “no man’s land” between SBA buyers and private equity funds. Jeff shares the patterns he sees across the market and what business owners can do right now to improve their position and expand their options, even if they’re not ready to sell. 

Whether you're prepping for an exit, considering a recap, or just want to understand what drives valuation and interest in the middle market, this episode gives you a grounded, experience-backed view into what's working—and what’s not—in M&A today.  

This conversation ties directly into the Elevate phase of the iBD™ Magic Model—helping owners increase strategic value, attract aligned capital, and design a business that’s ready for optionality. 
 
Jeff Buettner is a Managing Director at ButcherJoseph, where he works with owner-led businesses exploring recapitalizations, ESOPs, and strategic exits in the lower middle market. With deep experience across private capital markets, investment banking, and founder transitions, Jeff specializes in helping owners navigate complex deal dynamics while maintaining control and clarity. He is known for his honest, practical approach and his ability to bridge the gap between what founders want and what the market will support. 

Chapters:  

Resources: 
ButcherJoseph: https://www.butcherjoseph.com 
Jeff Buettner LinkedIn https://www.linkedin.com/in/jeff-buettner-8839432/ 
Ryan Tansom Website https://ryantansom.com/ 
 

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? 

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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 English, then connect those insights directly to the decisions owners are making around growth, liquidity, and long-term wealth. 

This isn’t about timing the market. It’s about understanding the rules of the game you're playing. Whether you’re holding cash, thinking about M&A, or planning for an exit, this episode helps you zoom out, think in first principles, and protect the future you’re building. 
 
Joe Brown is the founder of Heresy Financial, a YouTube channel and financial education platform that helps people understand how the economy really works. With millions of views and a growing audience of investors and entrepreneurs, Joe translates complex monetary policy, debt cycles, and macro trends into simple frameworks for decision-making. His contrarian, first-principles approach is trusted by those who want to protect their time, value, and wealth in a system built to extract them. 
 

Chapters:  

Resources: 
Heresy Financial YouTube Channel https://www.youtube.com/c/HeresyFinancial 
Ryan’s article on “How the System Steals Your Time” https://www.youtube.com/watch?v=lRUiyZNVrmA 
Ryan Tansom Website https://ryantansom.com/ 
 

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?  

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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 shows how business can be a platform to fund the life you actually want. Not someday—now.  

We unpack how to reclaim your time, align your ventures with your values, and stop optimizing for someone else’s scoreboard. If you’ve built a successful company but feel boxed in by what comes next, this episode is a wake-up call. You don’t need to sell to find meaning. You need clarity, ownership, and the courage to design your future on purpose. 
 
Mark Cleveland is a lifelong entrepreneur, investor, and business builder who’s launched and led multiple companies across industries—from logistics to retail to software. Rather than optimizing for scale or exits, Mark intentionally structures his ventures around what gives him energy, purpose, and time with his family. His philosophy flips the default growth narrative and shows that the real prize of entrepreneurship isn’t scale—it’s alignment. 
 

Chapters:  

Resources: 
Mark Cleveland on LinkedIn https://www.linkedin.com/in/markhcleveland/ 
37signals – calm company inspiration https://37signals.com/ 
Ryan Tansom Website https://ryantansom.com/

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. 

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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 built to be bought. 

We break down what actually happens when a $1–5M owner tries to exit: how they think, what they miss, and what buyers really see when they dig into the financials. Along the way, we talk through working capital expectations, earn-outs, founder dependency, and how to structure a deal that actually works. 

If you’re thinking about buying a business to grow—or you want a better understanding of how the lower market operates—this episode will give you the lens of a buyer and the clarity of someone who’s seen it all. 
 
Clint Fiore is the founder of Bison Business, a boutique M&A advisory firm that helps owners sell their companies and buyers find the right opportunities in the lower middle market. With experience as both an entrepreneur and a broker, Clint has built, scaled, and sold companies—and now helps others do the same. He’s personally advised on hundreds of deals, from owner-operated shops to more complex transactions, and he knows what buyers care about: clean financials, transferable operations, and a clear path to post-close success. Before founding Bison, Clint built and exited a national consumer brand, led sales in high-growth tech, and served aviation clients as a top commercial broker. In addition to leading Bison, Clint is developing Dealonomy—a new platform designed to modernize the small business deal marketplace by combining tech, transparency, and relationship-based brokerage. He’s also a private pilot, father of four, and a lifelong entrepreneur who brings a grounded, no-BS perspective to buying and selling businesses. 
 

Chapters:  

Resources: 
 
Bison Business Brokers – http://lackbeltmembers.com 

Clint’s LinkedIn - https://www.linkedin.com/in/clintfiore/ 

Ryan Tansom Website https://ryantansom.com/