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80% of businesses that go up for sale never actually sell. Shayne Connolly is one of the ones who did, and even he wasn't ready for what came after. He thought he'd be popping champagne. Instead, on the day the money hit the bank, he says he's never felt so deflated in his life.

In this episode, Matt Jones sits down with Shayne Connolly, a returning guest who spent the last few years turning his trade business into something he could actually sell, then went through the process of doing exactly that. Shane walks through the mindset shift from "business owner" to "asset owner," why the emotional side of exiting gets ignored in favour of the mechanics, what he wishes he'd asked himself before signing anything, and why he's now building a platform to help other owners see the asset sitting in front of them before it's too late to plan for it.

🎥 Watch the full episode: https://youtu.be/WGlussL7LIg

KEY CHAPTERS

00:00 - Introduction

01:56 - Meet Shayne Connolly

03:38 - Two Life-Changing Events at Once

04:38 - The Emotional Side of Selling a Business

06:43 - Knowing Your Exit Number

07:55 - From Business Owner to Asset Owner

09:48 - The Golden Handcuffs Problem

12:00 - Why He'd Rather Build Than Run

23:12 - The Conversation With His Wife

25:16 - Selling to Someone He Already Trusted

34:52 - Did He Even Need to Sell?

37:47 - Why Brokers Were a Waste of Time

45:11 - The First Chapter Is: Do You Really Want This?

46:26 - Closing Remarks and Resources

About the Guest: Shayne Connolly built his trade business into a genuine asset, one that could run without him, then sold it to a trusted team member rather than going through a broker. He's the author of Exit Plan and is now building OwnerHQ, a platform designed to help business owners understand the real value of what they've built and plan their exit long before they need one.

Website: https://exitplan.au

Software (in beta): https://ownerhq.biz

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