#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. 

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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: <...

Chapters

• (00:00:00) - Independence by Design Podcast
• (00:02:14) - Jumping In at Level 10
• (00:04:28) - How Did Your Parents Get Interest in Finance?
• (00:10:39) - Finance vs. Health: The Difference
• (00:13:46) - Cashing Out on Your Career
• (00:18:07) - Raymond James' Private Equity and Investment Banking Jobs
• (00:21:03) - George Conway on Financial Engineering vs Macro
• (00:25:51) - Private Equity and the Rest of Business
• (00:31:17) - On Gross Profit and VC Exporters
• (00:36:10) - Open Doors: The Business of Homebuying
• (00:37:43) - How to Make Money as a Public Company
• (00:40:35) - Private Equity vs. VC: Cash Flow
• (00:43:28) - In the Elevator With VCs
• (00:45:06) - Having Freedom Over My Time
• (00:47:22) - How To Change the Game
• (00:52:03) - Ideas for Starting a Business on a Mat Leave
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