The Tax Implications of Selling Your Business
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Release Date: 01/09/2026
The Tax Implications of Selling Your Business
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | Episode 26 | The Tax Implications of Selling Your Business 💼 Welcome to the second series of Boss Talk: Selling Businesses with Jim Parker and Carey Sobel! Just like the first series, you’ll get an inside look at the world of business brokerage, but this time, Jim and Carey are welcoming guests to the podcast. These powerhouse brokers and their guests dive into real, unfiltered conversations about buying and selling businesses, going far beyond balance sheets and financing. Let’s dive in. 🎙️ Join Jim and Carey in...
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Finding the Right Buyer
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses with Jim Parker and Carey Sobel | EP 25 | Finding the Right Buyer Link to video podcast episode: 💼 Welcome to Boss Talk: Selling Businesses with Jim Parker and Carey Sobel! Learn about the world of business brokerage on this video podcast. These two powerhouse brokers talk real talk about how to sell and buy, and it's far, far deeper than balance sheets and financing. Let's dive in! 🎙️ In this episode of Boss Talk, Jim and Carey cover the crucial topic of 'Finding the Right Buyer' from a seller's perspective. They break down the key...
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Red Flags That Can Cost You Your Business Sale
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 24 | Red Flags That Can Cost You Your Business Sale Link to video podcast episode: Welcome to Boss Talk! In today's episode, Jim Parker and Carey Sobel dive deep into the red flags that could jeopardize your business sale. 🚩 From declining financial trends 📉 to financial inaccuracies, heavy owner dependency, and unrealistic seller expectations, this episode covers it all! 🚀 Learn the importance of having clean financials, minimizing customer concentration, maintaining up-to-date systems, and disclosing any legal or...
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When Is the Right Time to Sell My Business?
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 23 | When Is the Right Time to Sell My Business? Video podcast link: Join Jim Parker and Carey Sobel in this eye-opening episode of Boss Talk as they tackle one of the most frequently asked questions by business owners: 'When is the right time to sell my business?' Timing is crucial and can determine whether you walk away with financial freedom or disappointment. They discuss key factors like personal readiness, financial preparedness, performance indicators, market cycles, and the challenges of predicting the best...
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No Such Thing as a Clean Closing
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 22 | No Such Thing as a Clean Closing Link to video podcast episode: The Truth About Business Closings: There Is No Such Thing as a Clean Closing 🏢📉 🎙️ In this episode of Boss Talk, Jim Parker and Carey Sobel explore the complexities of closing business deals. They delve into why there's no such thing as a smooth, problem-free closing, discussing various issues that can arise from third-party assignments to emotional meltdowns and last-minute surprises. They also talk about how the process has changed due to...
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How to Be a Good Buyer
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 21 | How to Be a Good Buyer Welcome back to another episode of Boss Talk: Selling Businesses With Jim Parker and Carey Sobel! In this episode, learn how to stand out as a top buyer in a seller's market. In this episode, learn how to stand out as a top buyer in a seller's market. Hosts Jim Parker and Carey Sobel discuss the challenges buyers face in a seller's market and how to stand out as a good buyer. With private equity groups on the rise and many corporate professionals looking to acquire businesses, it's essential to...
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Deal Structure 101
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 20 | Deal Structure 101 Link to video podcast episode: Welcome back to another episode of Boss Talk: Selling Businesses With Jim Parker and Carey Sobel! In this episode of Boss Talk, Jim Parker and Carey Sobel delve into the complexities of deal structure in business acquisitions. 💼🔍 They bust the myth that the purchase price is the only crucial factor, highlighting the importance of terms, buyer suitability, and negotiation points. The hosts break down asset sales vs. stock sales, discussing their pros and cons,...
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The Emotional Aspects of Selling Your Business
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 19 | The Emotional Aspects of Selling Your Business Link to video podcast episode: Welcome back to another episode of Boss Talk: Selling Businesses With Jim Parker and Carey Sobel! In this episode of Boss Talk, hosts Jim Parker and Carey Sobel dive into the important but often overlooked emotional aspects of selling a business. They discuss the deep personal connections business owners have with their companies, the emotional highs and lows throughout the sales process, and the impact on decision-making. The script...
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Financials: The Cornerstone of Selling Your Business
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses with Jim Parker and Carey Sobel | EP 18 | Financials: The Cornerstone of Selling Your Business Welcome back to another episode of Boss Talk: Selling Businesses with Jim Parker and Carey Sobel! In this episode of Boss Talk, hosts Jim Parker and Carey Sobel delve into the critical role of financials when selling a business. They emphasize that organized and accurate financial statements are crucial from the initial listing to the final closing. Topics include the importance of clean financial records, how personal and one-time expenses impact the valuation, and the...
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How Long Will It Take to Sell My Business?
Boss Talk: Selling Businesses with Jim Parker & Carey Sobel
Boss Talk: Selling Businesses with Jim Parker and Carey Sobel | EP 17 | How Long Will It Take to Sell My Business? Link to video podcast episode: Welcome back to another episode of Boss Talk: Selling Businesses with Jim Parker and Carey Sobel! In this episode of Boss Talk, Jim and Carey discuss why there is no definitive answer to how long it will take to sell a business due to the myriad of variables involved. The two seasoned brokers elaborate on the importance of preparation, the critical first 30 days on the market, and how hiring professionals can expedite the process. They also examine...
info_outlineBoss Talk: Selling Businesses With Jim Parker and Carey Sobel | Episode 26 | The Tax Implications of Selling Your Business
💼 Welcome to the second series of Boss Talk: Selling Businesses with Jim Parker and Carey Sobel! Just like the first series, you’ll get an inside look at the world of business brokerage, but this time, Jim and Carey are welcoming guests to the podcast. These powerhouse brokers and their guests dive into real, unfiltered conversations about buying and selling businesses, going far beyond balance sheets and financing. Let’s dive in.
🎙️ Join Jim and Carey in the latest episode of Boss Talk as they dive into 'The Tax Implications of Selling Your Business.' Featuring special guest Richard Hayes from Coastal Investment Company, this episode explores the critical topic of tax planning for business sales. Learn about purchase price allocation, asset vs. stock sales, depreciation recapture, and the advantages of proactive tax planning. Discover how to maximize what you keep in your pocket post-sale with expert insights and practical advice. Don't miss this informative discussion designed to help you navigate the complex world of business tax implications! 🎯
📌 Business owners, if this content resonated with you, feel free to contact Boss Group International for any inquiries or to get started with a Broker’s Opinion of Value. We're here to serve you and ensure your business goals are met with excellence.
🌐 For more information on selling your business, visit https://www.bossgi.com
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00:00 Introduction to Boss Talk
00:26 Introducing Today's Topic: Tax Implications
00:58 Meet the Expert: Richard Hayes
03:19 Understanding Tax Planning for Business Sales
04:01 The Importance of Purchase Price Allocation
15:21 Asset Sale vs. Stock Sale
22:15 Tax Implications of Installment Sales
27:47 Understanding Amortization
29:24 Exploring 1031 Exchange
33:04 State Tax Considerations
35:47 Retirement Planning and Lifestyle Impact
42:04 Common Mistakes and Final Advice
#TaxPlanning #BusinessSales #BossTalk #SellingBusinesses #BossGroup #CoastalInvestments #BusinessBroker #BusinessPodcast