0059 - Why He Sold a $16M Business for $100K; What Every Buyer Needs to Know

In this episode, Tim sits down with Alan Underwood, a coach, speaker, investor, and entrepreneur, to talk about the seller side of small business transactions. Alan shares the story of building and selling a car dealership, including launching from a former junkyard, surviving a fire before opening, navigating the 2007 credit crunch, and eventually growing the business into a multi-location dealership doing roughly $16 million in annual revenue. Tim is an entrepreneur who believes everyone should explore the opportunities that business and real estate can provide on the path to financial freedom. He owns and operates a wine & liquor store, a software startup, a consulting company, and a growing portfolio of commercial and residential real estate. Tim's passion for independent business has led him to support dozens of other business owners. For over a decade, he has worked with businesses on strategy, processes, finances, and marketing. These experiences, along with analyzing dozens of other businesses for potential acquisition, have provided Tim with an immense knowledge base to pull from. Tim has appeared on multiple top-tier podcasts in the financial space, such as Bigger Pockets Money and The Freedom Chasers Podcast. Content note: This episode includes discussion of grief, depression, PTSD, and suicidal ideation. 00:00 – 01:34 | The Burning Junkyard and Seller Perspective 01:34 – 03:02 | The Car Dealership Alan Sold 03:02 – 08:15 | Choosing Ownership Over Security 08:15 – 13:21 | Launching From a Junkyard on Fire 13:21 – 18:38 | Learning Business Through Pizza and Systems 18:38 – 27:18 | Growing Through Financing, Customers, and Process 27:18 – 34:30 | Why Alan Decided to Sell 34:30 – 40:09 | Understanding the Seller's True Situation 40:09 – 50:51 | Healing, Coaching, and Final Lessons Guest Bio Alan Underwood is a coach, speaker, investor, and entrepreneur who has built and sold multiple businesses, including pizza restaurants and a car dealership. His car dealership grew to two locations, earned strong customer reviews, built a major local following, and reached approximately $16 million in annual revenue. Connect with Alan: Instagram: instagram.com/thealanunderwood/ Facebook: facebook.com/alan.underwood.54 Website: thealanunderwood.com/ LinkedIn: linkedin.com/in/the-alan-underwood Connect with Tim and the community on social media for more tips and updates: Website: https://www.powerofbiz.com YouTube: https://www.youtube.com/@powerofbiz Instagram: https://www.instagram.com/timtdelaney/ Threads: https://www.threads.com/@timtdelaney LinkedIn: https://www.linkedin.com/in/timothytdelaney/ Facebook: https://www.facebook.com/timtdelaney Tweetable Quotes "Pray hard, work hard, and treat people right." — Alan Underwood "A business can be financially valuable and personally crushing at the same time." — Alan Underwood "The number on the offer sheet does not always tell the whole seller story." — Tim Delaney