Most owners talk about “creating value,” but few stop to ask a more fundamental question: 
Value for what? 

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In this episode, I sat down with my friend Nick Bradley—entrepreneur, investor, and host of The Scale Up Podcast—to explore how your ownership goals determine everything about your value-creation strategy. Nick comes from the private equity world, where the goal is clear: build to sell. I work with mid-market owners designing companies that can outlast them. 
We both work with the same kinds of businesses—but from opposite ends of the ownership spectrum. Together, we dig into how clarity of intent changes the entire game: the capital structure you choose, how you lead your team, and how you allocate your time and cash flow. 
 
This isn’t about chasing one “right” path. It’s about picking your game—and understanding what freedom, wealth, and legacy look like depending on whether you’re designing for a third-party exit or an internal transition. 

What We Covered 

• Why every ownership strategy starts with defining the end game 

• How valuation, structure, and leadership priorities change across exit paths 

• The investor lens: what third-party buyers actually look for 

• The owner lens: what matters most in family or internal transitions 

• How clarity on your long-term goal aligns your strategy, team, and time 

• The tradeoffs between liquidity, legacy, and control 

• Why “value creation” looks different depending on the game you’re playing 

Who This Is For 
For any owner trying to decide what’s next—whether to sell, transition internally, or redesign their role—this episode will help you see the tradeoffs clearly. If you want to understand how your value-creation plan must align with your personal and ownership goals, this conversation will give you the clarity to design your next move intentionally. 

Nick Bradley is an entrepreneur, investor, and former PE-backed CEO/Operating Partner who has scaled 100+ businesses and driven $5B+ in exits. Host of the top-ranked Scale Up with Nick Bradley podcast and author of the #1 bestseller Exit for Millions, he works with founders generating $1M+ EBITDA to diagnose true enterprise value and 2–10x it through operational excellence, acquisitions, and systems—so owners create freedom, optionality, and elite businesses. 

Chapters:  

• (00:00 ) Nick Bradley joins to discuss his new book 

• (05:24 ) Ryan's ownership operating system and ideal client profile 

• (08:36 ) Three layers of exit and different coaching approaches 

• (18:34 ) Scale to sale framework and five pillars explained 

• (32:40 ) Private equity playbook and value creation strategies 

• (35:50 ) Real deal example: Rolling up three companies strategy 

• (46:15 ) Valuation expectations gap and education challenges explained 

Chapters

• (00:00:00 ) - Business Owners: Independence by Design
• (00:01:03 ) - Scaling Up For Life With Nick Bradley
• (00:03:59 ) - Nick and Ryan on Catching Up
• (00:05:56 ) - Exit the Company From the Boardroom
• (00:10:01 ) - Private Equity and the Collab
• (00:14:18 ) - How To Decide Between Scale and Sale
• (00:17:10 ) - Has Private Equity Bubble Stopped?
• (00:18:12 ) - Expletive for Millions: Scale to Sale
• (00:21:33 ) - Preparation and Profit Up
• (00:22:18 ) - Exploring the Exit Story
• (00:23:14 ) - When to Sell a Company to Private Equity
• (00:23:44 ) - The Fifth Pillar of a Strategic Sale
• (00:24:45 ) - TIA: Simple Strategy, Complex Execution
• (00:29:29 ) - Private Equity Is Going Through Some Turmoil
• (00:30:41 ) - Private Equity: Cash Flow and Value
• (00:33:00 ) - Private Equity: The M&A Market
• (00:38:25 ) - Private Equity: The Alternative to Countdowns
• (00:39:08 ) - Why the Multiple Gap Is So Real
• (00:41:36 ) - Philanthropist and Debbie Downer: How to Sell a Business
• (00:46:01 ) - The Role of Strategic Consultations
• (00:50:34 ) - What's Your Joy in the High-Value Acceleration?
• (00:51:09 ) - How to Scale Your Business.
• (00:53:40 ) - Ideas for Scale and Value Expansion
• (01:00:15 ) - On The Future of Family Businesses
• (01:04:11 ) - The Value of a Board Member
• (01:06:54 ) - No More Neglecting My Clients