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Independence by Design™

Independence by Design™ is a framework to help owner-operators get out of the weeds and lead from the boardroom. I built it because I lived this trap. In 2009, I joined my dad in our $21M family business. We turned it around and sold it for eight figures in 2014 — enough to pay off debt, cover taxes, let my dad retire, and leave me with a chunk of cash at 27. But the sale gutted our team, systems, and identity. It looked like a win, but it didn’t feel like freedom. I bawled in the driveway. After

business entrepreneurship

All Episodes

01:57:14

#456: Panel Debate | The Ownership Game (the 2%) vs....

Independence by Design™ ·

2025/08/28

Most advice treats all owners the same. The reality? There are two different games. For the 98% (smaller, tightly owner‑dependent companies), the job and the asset are commingled. Generic “exit planning” advice often creates noise: the math, buyers, and timelines rarely line up. For the 2% (true middle‑market owners with durable EBITDA and a management team), the game shifts to the boardroom. It’s about capital allocation—protecting value, preserving

en

01:17:42

#455: Jim Carlisle | Boardroom Ownership: Protecting...

Independence by Design™ ·

2025/08/21

If your goal is to run your company from the boardroom, the real work isn’t just stepping out of day-to-day operations. It’s making sure the business—and your wealth—are protected no matter what happens. In this conversation with attorney and deal advisor Jim Carlisle. Jim has guided hundreds of owners through sales, ESOPs, continuity crises, and legacy planning—and he’s seen what works, what destroys value, and what keeps owners up at night. We unpack

en

01:17:42

#455: Jim Carlisle | Boardroom Ownership: Protecting...

Independence by Design™ ·

2025/08/21

If your goal is to run your company from the boardroom, the real work isn’t just stepping out of day-to-day operations. It’s making sure the business—and your wealth—are protected no matter what happens. In this conversation with attorney and deal advisor Jim Carlisle. Jim has guided hundreds of owners through sales, ESOPs, continuity crises, and legacy planning—and he’s seen what works, what destroys value, and what keeps owners up at night. We unpack

en

01:41:01

#454: Candice Bradley | Designing the Game You Want...

Independence by Design™ ·

2025/08/14

If you want to design a business that works for your life — not the other way around — you need to understand the actual game you’re playing. Watch on YouTube In this episode, I sit down with Candice Bradley, a business owner, investor, former banker, and strategic advisor who’s lived through nearly every ownership structure in the capitalist playbook: banking, investment banking, private equity, public markets, venture capital, and now private business

en

01:41:01

#454: Candice Bradley | Designing the Game You Want...

Independence by Design™ ·

2025/08/14

If you want to design a business that works for your life — not the other way around — you need to understand the actual game you’re playing. In this episode, I sit down with Candice Bradley, a business owner, investor, former banker, and strategic advisor who’s lived through nearly every ownership structure in the capitalist playbook: banking, investment banking, private equity, public markets, venture capital, and now private business

en

01:34:49

#453: Jennifer Davis | From Chaos to Cash: The Comp...

Independence by Design™ ·

2025/08/07

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,

en

01:34:49

#453: Jennifer Davis | From Chaos to Cash: The Comp...

Independence by Design™ ·

2025/08/07

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,

en

01:23:32

#452: Geoff Woods | Author of The AI-Driven Leader

Independence by Design™ ·

2025/07/31

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

en

01:23:32

#452: Geoff Woods | Author of The AI-Driven Leader

Independence by Design™ ·

2025/07/31

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

en

01:12:09

#451: Paul Spiegelman | The Origin Story of the Small...

Independence by Design™ ·

2025/07/24

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 Small Giants Community, to trace the full arc of a founder's

en

01:12:09

#451: Paul Spiegelman | The Origin Story of the Small...

Independence by Design™ ·

2025/07/24

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 Small Giants Community, to trace the full arc of a founder's

en

01:13:39

#450: Jean Moncrieff | Letting Go, Leading with...

Independence by Design™ ·

2025/07/17

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 owner eventually faces: when and how to let go. We unpack

en

01:13:39

#450: Jean Moncrieff | Letting Go, Leading with...

Independence by Design™ ·

2025/07/17

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 owner eventually faces: when and how to let go. We unpack

en

00:33:28

#449: Ryan Tansom | Understanding the Meaning of...

Independence by Design™ ·

2025/07/10

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 spirituality all fit together? If you’ve ever wondered why I care so

en

00:33:28

#449: Ryan Tansom | Understanding the Meaning of...

Independence by Design™ ·

2025/07/10

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 spirituality all fit together? If you’ve ever wondered why I care so

en

01:28:42

#448: Jennifer Davis | Bootstrapping Davisware to...

Independence by Design™ ·

2025/07/03

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 arc of building, leading, and eventually stepping away from a

en

01:28:42

#448: Jennifer Davis | Bootstrapping Davisware to...

Independence by Design™ ·

2025/07/03

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 arc of building, leading, and eventually stepping away from a

en

00:45:15

#447: Jeff Buettner | Q2 2025 M&A Update: What Buyers...

Independence by Design™ ·

2025/06/26

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 talk candidly about what’s really driving—or

en

00:45:15

#447: Jeff Buettner | Q2 2025 M&A Update: What Buyers...

Independence by Design™ ·

2025/06/26

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? 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

en

01:00:28

#446: Joe Brown | What Every Owner Should Know About...

Independence by Design™ ·

2025/06/19

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 English, then connect those insights directly to the decisions

en

151 results

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