The Site Shed | Systems, Strategy and Growth for Tradies and Contractors
The Site Shed is a global podcast for tradies and contractors who want clearer systems, stronger strategy, and steadier business growth. Each episode is designed to educate and inform around the topics that matter most in running and scaling a modern trade business.
Hosted by former plumber and digital agency owner Matt Jones, the podcast dives into real-world conversations on marketing, operations, apprenticeships, technology, hiring, leadership, finance, and more, all tailored to the trades and construction industry.
You’ll hear practical insights, honest lessons, and expert perspectives from across the globe.
Whether you work as a tradie, contractor, builder, electrician, landscaper, or run any service-based business, you’ll find ideas and experiences you can put into action straight away.
If you're ready to work smarter, not harder, The Site Shed gives you the tools, frameworks, and viewpoints to help your business move forward with confidence.
The Site Shed | Systems, Strategy and Growth for Tradies and Contractors
How to Turn a Trade Business Into a Sellable Asset | ft. Shayne Connolly | Ep. 509
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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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