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 450+ interviews, thousands of owners, and multiple ventures, I saw the real issue: we didn’t know the difference between being owners and operators. Our goals weren’t aligned. And we had no framework to guide us.
That’s why I built iBD — to help owners avoid regret, reclaim their time, grow real equity value, and build a business that gives them freedom — whether they stay, scale, or sell.
This show is the one I wish I had.
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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 450+ interviews, thousands of owners, and multiple ventures, I saw the real issue: we didn’t know the difference between being owners and operators. Our goals weren’t aligned. And we had no framework to guide us.
That’s why I built iBD — to help owners avoid regret, reclaim their time, grow real equity value, and build a business that gives them freedom — whether they stay, scale, or sell.
This show is the one I wish I had.
#454: Candice Bradley | Designing the Game You Want to Play: Ownership, Capitalism & Real Decision Making
Independence by Design™
1 hour 41 minutes 1 second
2 months ago
#454: Candice Bradley | Designing the Game You Want to Play: Ownership, Capitalism & Real Decision Making
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 ownership.
Candice doesn’t just know the rules of finance and business ownership — she’s played in every field. And in this conversation, she unpacks what most owners miss: the game isn’t just about money. It’s about the structure you choose, the bets you make, and whether those bets are actually worth your time.
We go deep into:
Why understanding valuation, risk, and cash flow is foundational to making good decisions as an owner
How different forms of ownership — from PE to VC to private — come with built-in expectations that shape your life
What happens when you finally see the system for what it is… and choose to design your own rules
And toward the end, we cut through the jargon and speak plain English: the fiat system is broken. Time is scarce. And if we’re not choosing our game and constraints consciously, they’ll be chosen for us.
This is a conversation for owners who are ready to lead with clarity — and design a business that gives them options, not just obligations.
Key Themes:
The connection between valuation and decision clarity
Why private owners must define their own timelines and targets
Tradeoffs between financial engineering and operational cash flow
Escaping fiat-based illusions and designing a game that actually works for your life
Who This Is For:
If you're an owner-operator who:
Is tired of gut-based decisions and wants a clear strategy
Feels the weight of every tradeoff between time, cash, and equity
Wants to understand how different financial models and ownership structures actually affect your freedom
...this episode is for you.
Candice’s journey will help you see the full landscape — and start placing your bets with intention. Candice Bradley is a 3x founder and seasoned operator with 20+ years across investment banking, private equity, venture, and entrepreneurship. She’s built and scaled businesses from both sides of the table — as investor and owner — and now helps founders navigate the tradeoffs of growth, cash flow, and exit. Her current focus: acquiring and operating a $15M+ company with intention and impact.
Chapters:
(00:00) Introduction and Ryan's excitement about the conversation level
(02:11) Can...
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 450+ interviews, thousands of owners, and multiple ventures, I saw the real issue: we didn’t know the difference between being owners and operators. Our goals weren’t aligned. And we had no framework to guide us.
That’s why I built iBD — to help owners avoid regret, reclaim their time, grow real equity value, and build a business that gives them freedom — whether they stay, scale, or sell.
This show is the one I wish I had.
