🫱🏻‍🫲🏼 Book a Free Strategy Call with Tradie Web Guys: https://tradie.wiki/tssyt 60% of business transitions fail — and it's rarely the tax strategy that kills them. The real culprit is the stuff nobody wants to talk about: unclear expectations, poor communication, and the relationships between the people involved. Matt Jones sits down with Andrea Carpenter from The Transition Strategists to unpack why so many family business successions fall apart, and what trade business owners can do to make sure theirs doesn't. Whether you're thinking about stepping back in 2 years or 20, Andrea breaks down the three generations of transition thinking, the Transition Compass tool, and why starting the conversation 7 to 10 years out isn't too early — it's just smart. If you've ever thought about selling, handing down, or stepping away from your business, this one's for you. 🎥 Watch the full episode: https://youtu.be/LCu3zgBwLho KEY CHAPTERS 00:00 - Introduction 00:55 - The Site Shed Hits 500 Episodes 02:00 - Meet Andrea Carpenter 02:20 - What Is a Business Transition? 03:20 - Internal vs External Transition Options 04:10 - Why Trade Businesses Are Now Sellable Assets 07:00 - The Real Reason Transitions Fail 10:30 - Transition 1.0, 2.0 and 3.0 Explained 14:00 - Fairness vs Equality in Family Business 19:00 - Designing the Transition With Your Successor 22:00 - The Transition Compass Tool 26:00 - How to Start the Conversation Early 30:00 - Working Yourself Out of Your Own Role 33:00 - How Long a Transition Really Takes 37:00 - Why 75% of Owners Regret Selling 41:00 - Closing Remarks and Resources About the Guest: Andrea CarpenterAndrea Carpenter is the founder of The Transition Strategists and specialises in business succession and transition planning. She works with family-owned and privately held businesses — including trade and home service operators — to help owners design exits that actually work. Her focus is the human side of transition: the relationships, conversations, and structures that determine whether a handover succeeds or falls apart. Website: https://transitionstrategists.com/ Free resource: https://beforebuysell.com/ LinkedIn: https://www.linkedin.com/in/andreakcarpenter/ CONNECT WITH THE TRADIE WEB GUYS!Website: https://www.tradiewebguys.com.au/ YouTube: https://www.youtube.com/@TradieWebGuysOfficial?sub_confirmation=1 Facebook: https://www.facebook.com/TradieWebGuysOfficial Instagram: https://www.instagram.com/tradiewebguys/ LinkedIn: https://au.linkedin.com/company/tradie-web-guys Matt's LinkedIn: https://www.linkedin.com/in/iamthemattj/ If you enjoyed this podcast, please take a moment to leave us a review: ⭐ https://lovethepodcast.com/TheSiteShed Love the audio version of this podcast? Subscribe to the link below: ⭐ https://followthepodcast.com/TheSiteShed #podcast #thesiteshed #tradiewebguys #businesstransition #familybusiness #exitstrategy #successionplanning #tradiebusiness Your Next Step:Join Tradie Academy, our free community packed with templates, checklists, and resources shared by podcast guests, coaches, and successful tradies.👉 Join free and grab your next growth tool here: https://tradie.wiki/podFollow The Site Shed:Facebook: The Site ShedInstagram: @thesiteshedLinkedIn: Matt JonesWebsite: thesiteshed.comYouTube: @TheSiteShedIf you enjoyed this podcast and the series, please take 5 minutes to leave us a review:⭐ https://lovethepodcast.com/TheSiteShedLove the audio version of this podcast? Subscribe to the link below:⭐ https://followthepodcast.com/TheSiteShed