Most business owners wait until they’re tired to think about selling. By then, it’s too late — and it can cost them millions.

In this episode of CEOs Unscripted, host Jane Gentry sits down with Ryan Frederick, principal of Transform Labs — a serial entrepreneur who has started and sold company after company, and whose latest venture was just acquired.

Ryan and Jane pull back the curtain on what buyers actually want, why a full calendar can be a red flag, and the uncomfortable truth about being the bottleneck in your own business. If you’re a mid-market CEO who ever plans to sell — or simply wants to build a business that can run without you — this is the conversation to hear.

Key Topics Covered:

• Why you should plan your exit the day you open the doors — not the day you’re tired
• The “full calendar” trap and how being busy can signal you’re the bottleneck
• Why you can’t sell a business you’re still working IN
• How to get honest feedback and why your team may never give it to you
• The “mock transaction” test to determine whether your business is truly sellable
• How to prepare your people and leadership team for a successful integration
• Why culture and values can quietly kill more deals than valuation
• How long you really have to stay after a sale — and why it’s often shorter than the contract suggests
• The 30% haircut that can hit unprepared businesses at the negotiating table
• The emotional side of selling and figuring out who you are after the business is gone

💬 A Few Lines That Stuck With Us:

• “You’re climbing the ladder, doing activity — but how do you know it’s leaning against the right wall?” — Jane Gentry
• “You’re not selling the past. The story you’re selling is the future.” — Jane Gentry
• “We get what we earn. Not what we deserve, but what we earn.” — Ryan Frederick

📌 Episode Timestamps:

• 00:00 — “You Need a Mirror”: Cold Open
• 00:53 — Welcome to CEOs Unscripted
• 02:29 — Meet Ryan Frederick: A Serial Entrepreneur’s Story
• 04:38 — The High-Risk Reality of Going Out on Your Own
• 05:37 — Job Security Is Dead & the Rise of the Influencer Career
• 08:35 — Get an Exit Plan the Day You Open the Doors
• 11:22 — The Full Calendar Trap: Working IN vs. ON the Business
• 14:04 — Ego, Identity & Why Founders Can’t Let Go
• 17:28 — Surround Yourself With People Who’ll Tell You the Truth
• 21:36 — Is Your Ladder Leaning Against the Right Wall?
• 22:07 — BREAKING: Transform Labs Has Been Acquired
• 23:49 — Sell the Future, Not the Past
• 24:33 — The “Mock Transaction” Test & Integration Readiness
• 25:33 — Prepping Your People & Leadership Succession
• 28:30 — How Long You Really Stay After the Sale
• 31:15 — Why Deals Die: Culture, Gut & Buyer’s Remorse
• 35:36 — When Values Kill a Deal: The Company Car Story
• 37:56 — The Emotional Side of Selling: Who Are You After?
• 40:52 — Succession Planning: Why Owners Wait Too Long
• 45:22 — Breaking the Owner’s Delusion & the 30% Haircut
• 48:11 — What’s Next for Ryan + The Truth About Retirement
• 51:43 — Closing Thoughts

👤 About Ryan Frederick:

Ryan Frederick is the principal of Transform Labs and a serial entrepreneur with multiple exits under his belt. Following the recent acquisition of Transform Labs, Ryan continues to work with the acquiring company, leading integration and growth while also traveling the country speaking about AI.

🎙️ About CEOs Unscripted:

CEOs Unscripted is a bi-weekly podcast for mid-market CEOs, featuring real conversations with leaders scaling $10M–$500M businesses. Hosted by Jane Gentry, the show cuts through the fluff and jargon to share honest lessons from CEOs, founders, and executives who’ve been where you are.