Boss Talk: Selling Businesses with Jim Parker & Carey Sobel

Boss Group International
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Jim Parker & Carey Sobel help people buy and sell businesses. Their expertise in this is unmatched, as is their passion for taking great care of all parties involved. This show, Boss Talk: Selling Businesses With Jim Parker and Carey Sobel, is Jim & Carey hashing out what is going on in the world of business brokerage and the best practices that surround getting it right. It's built for business owners to listen and prepare their business to be the best, salable property possible. It's built for business buyers to learn how to identify a good opportunity, offer well, and transition powerfully. This is a show for people who really care to be a part of business transitions in all the right ways.

  1. FEB 12

    Life After the Sale: What's Next for Business Owners?

    Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | Episode 27 | Life After the Sale: What's Next for Business Owners?    💼 Welcome to the second series of 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!   🎙️ Welcome to Boss Talk! In this episode, Jim and Carey discuss the crucial topic of 'Life After the Sale: What Comes Next for Business Owners.' 🏢💼 Selling a business is more than just a financial transaction; it's an emotional journey as well. The pair delve into the planning required for a successful exit, including the importance of having a life plan in place. They share insights into the emotional challenges faced before, during, and after the sale, and emphasize the significance of maintaining social, intellectual, and physical health post-retirement. Whether you're thinking of selling your business soon or years down the line, this episode offers valuable advice on how to prepare for this major life transition. 🌟👨‍💼👩‍💼 📌 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  👉 Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel    ⁨@ListenToBossTalk⁩   ✍️ Leave us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode.  👉 Catch up on past episodes here: https://www.youtube.com/playlist?list=PL6P2KZ69USp7uXhVKINeFL6IzcV9dr0fa  00:00 Introduction and Hosts 00:15 The Importance of Planning Life After the Sale 00:44 Emotional Aspects of Selling a Business 02:10 Identity and Prestige Post-Sale 02:57 Seller Experiences and Emotional Stories 06:34 Buyer's Perspective and Due Diligence 13:47 Realistic Valuation and Market Expectations 20:56 Social and Personal Considerations Post-Sale 23:29 Planning for a Gradual Transition 24:13 Balancing Work and Personal Life 27:14 Financial Considerations for Retirement 29:05 Emotional and Practical Aspects of Selling a Business 35:38 Post-Sale Responsibilities and Challenges 41:53 Common Post-Sale Mistakes to Avoid 45:40 Embracing Retirement as a New Chapter #BossTalk #SellingBusinesses #BossGroup #CoastalInvestments #BusinessOwner #BusinessBroker #BusinessPodcast

    48 min

  2. JAN 9

    The Tax Implications of Selling Your Business

    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 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  👉 Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel @ListenToBossTalk ✍️ Leave us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode. 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

    52 min

  3. 12/04/2025

    Finding the Right Buyer

    Boss Talk: Selling Businesses with Jim Parker and Carey Sobel | EP 25 | Finding the Right Buyer Link to video podcast episode: https://youtu.be/NftfxLebZj4   💼 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 factors that influence choosing the ideal buyer into three categories: working with people you like, finding a buyer that offers the best chance to close, and identifying a buyer for the long term. Through real-world examples and personal experiences, they discuss how emotional attachment, cultural fit, communication styles, and financial qualifications play pivotal roles in the selling process.  Whether it's seller financing, equity rollover, or post-closing transitions, this episode offers invaluable insights for sellers looking to find not just any buyer, but the right one.  Stay tuned to the next series of Boos Talk, coming soon! 🎯 📌 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   👉 Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel   @ListenToBossTalk  Leave us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode.  Catch up on past episodes here: https://www.youtube.com/playlist?list=PL6P2KZ69USp7uXhVKINeFL6IzcV9dr0fa  00:00 Introduction and Episode Overview 00:40 Choosing the Right Buyer: People You Like 01:47 Cultural Fit and Communication 06:12 Buyer-Seller Relationship Dynamics 13:05 Evaluating Buyer Experience and Financial Capability 22:28 Handling Multiple Offers and Buyer Behavior 23:35 Buyer Preparedness and Professionalism 24:03 Negotiation Strategies During Due Diligence 25:18 The Importance of Synergy Between Buyer and Seller 28:00 Understanding Equity Rollover 31:51 Seller's Perspective on Business Growth and Retirement 35:07 Finding the Right Buyer for Long-Term Success 40:41 Final Thoughts and Advice for Sellers #bosstalk #sellingbusinesses #businesspodcast #businessbroker #bossgroup #businessowner #businesssales

    44 min

  4. 10/30/2025

    Red Flags That Can Cost You Your Business Sale

    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: https://youtu.be/xVa98fYWNyo  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 compliance issues. Whether you're looking to sell your business or buy one, this episode is packed with essential insights that you can't afford to miss. Tune in to avoid these pitfalls and make your business transaction smooth and successful! 🔑 📌 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   👉 Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel  ⁨@ListenToBossTalk⁩   us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode.  Catch up on past episodes here: https://www.youtube.com/playlist?list=PL6P2KZ69USp7uXhVKINeFL6IzcV9dr0fa   00:00 Introduction to Boss Talk 00:45 Understanding Financial Red Flags 01:35 The Impact of Declining Financial Trends 03:56 Financial Inaccuracies and Their Consequences 05:09 The Importance of Business Financeability 07:43 Owner Financing: Pros and Cons 12:39 Seller's Motivation and Trustworthiness 17:32 Employee and Vendor Turnover 21:37 Client and Vendor Concentration Risks 27:07 Owner Dependency in Business 27:23 The Problem with Overworking 28:49 Interdependency and Relationships 32:04 Importance of Systems and Documentation 37:24 Legal and Compliance Issues 42:33 Competitor Threats and Industry Changes 51:01 Unrealistic Seller Expectations 53:50 Conclusion and Final Thoughts #bosstalk #sellingbusinesses #businesspodcast #businessbroker #bossgroup #businessowner #businesssales

    55 min

  5. 10/02/2025

    When Is the Right Time to Sell My Business?

    Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 23 | When Is the Right Time to Sell My Business?  Video podcast link: https://youtu.be/JFs-CIaQfTY  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 time to sell. With real-world examples and expert advice, this episode is packed with insights for any business owner considering their exit strategy. Don't miss it! 🏢💼📈 📌 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  👉 Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel     ⁨@ListenToBossTalk⁩   Leave us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode.  Catch up on past episodes here: https://www.youtube.com/playlist?list=PL6P2KZ69USp7uXhVKINeFL6IzcV9dr0fa  00:00 Introduction to Boss Talk 00:18 The Importance of Timing in Selling Your Business 00:58 Exit Planning as a Business Strategy 01:23 The Three Legs of the Stool: Personal Readiness 02:31 Recognizing Burnout and Loss of Passion 06:48 Financial Readiness: When Your Business is Gravy, Not Oxygen 10:13 Business Attractiveness: Indicators for Selling 15:44 Market Cycles and Economic Factors 25:52 The Hot Market for Home Services 26:51 The Importance of Exit Planning 27:51 The Role of Business Brokers 29:24 Preparing Your Business for Sale 40:28 Family Transitions in Business 47:22 When is the Right Time to Sell? 51:07 Conclusion and Key Takeaways #bosstalk #sellingbusinesses #businesspodcast #businessbroker #bossgroup #businessowner #businesssales

    53 min

  6. 08/28/2025

    No Such Thing as a Clean Closing

    Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 22 | No Such Thing as a Clean Closing Link to video podcast episode: https://youtu.be/czgB-1XnAhM  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 technology and the importance of adaptability. With plenty of anecdotes and practical advice, this episode is a must-watch for anyone involved in business transactions. 🤝💼! 📌 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   👉 Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel   @ListenToBossTalk     Leave us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode.  Catch up on past episodes here: https://www.youtube.com/playlist?list=PL6P2KZ69USp7uXhVKINeFL6IzcV9dr0fa  00:00 Introduction to Boss Talk 00:19 The Myth of a Clean Closing 00:40 Unexpected Obstacles in Transactions 02:51 The Role of Technology in Closings 05:41 Common Causes of Closing Delays 06:30 Third-Party Complications 16:01 Post-Closing Challenges 22:51 Handling Disputes and Post-Closing Adjustments 23:54 Merchant Services and Prorations 27:22 Transition Expectations and Employee Management 29:52 Leading Up to Closing: Documents and Emotions 37:31 Final Steps and Closing Realities #bosstalk #sellingbusinesses #businesspodcast #businessbroker #bossgroup #businessowner #closing #businesssales #realestateclosing

    42 min

  7. 07/24/2025

    How to Be a Good Buyer

    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 follow a respectful and organized approach. They emphasize the importance of having a strong bio, demonstrating financial capacity, and being clear about one's wants and needs. The episode also covers common pitfalls, such as unpreparedness and acting entitled, and offers actionable advice on being courteous, respectful, and transparent throughout the buying process. 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   Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel  ⁨@ListenToBossTalk⁩   Leave us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode.  Catch up on past episodes here: https://www.youtube.com/playlist?list=PL6P2KZ69USp7uXhVKINeFL6IzcV9dr0fa  00:00 Introduction to Boss Talk 00:46 Understanding the Seller's Market 02:50 How to Stand Out as a Good Buyer 07:52 The Importance of Courtesy and Respect 13:06 Being Organized and Punctual 14:28 Introduction to Business Discussions 14:51 Understanding Seller's Motivation 15:50 Importance of Preparation and Response Time 16:21 Effective Buyer-Seller Communication 19:19 Transparency and Trust in Transactions 24:01 Pitfalls of Misrepresentation 29:17 Final Thoughts and Recommendations #bosstalk #sellingbusinesses #businesspodcast #businesssales #podcast #bossgroup #businessfinance #businessowner #businessbroker #sellersmarket

    30 min

  8. 06/26/2025

    Deal Structure 101

    Boss Talk: Selling Businesses With Jim Parker and Carey Sobel | EP 20 | Deal Structure 101 Link to video podcast episode: https://youtu.be/NrRCfFWST6I  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, tax implications, and scenarios where each is applicable. 📊 They also emphasize crucial negotiation elements such as seller financing, earn outs, rollover equity, and other non-price terms. If you're thinking about buying or selling a business, this episode is a must-watch for understanding the ins and outs of deal structure! 🚀 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  Subscribe for the latest from Boss Talk: Selling Businesses with Jim Parker and Carey Sobel on YouTube  @ListenToBossTalk    Leave us a comment, like, and share! We welcome your feedback! Let us know if there is a topic that's on your mind, and if you would like us to cover it in a future episode.  Catch up on past episodes here: https://www.youtube.com/playlist?list=PL6P2KZ69USp7uXhVKINeFL6IzcV9dr0fa   00:00 Introduction to Deal Structure 101 01:22 Understanding Asset Sales vs. Stock Sales 02:41 Pros and Cons of Stock Sales 08:15 Pros and Cons of Asset Sales 09:52 Negotiation Points in Deal Structure 10:11 Non-Compete Agreements 14:03 Familiarization and Transition Periods 20:47 Asset Allocation and Tax Implications 23:04 Breaking Down the $5 Million Allocation 23:57 The Importance of Asset Allocation 26:47 Seller Financing Explained 29:13 The Risks of Seller Financing 33:50 Earnouts and Contingent Payments 38:27 Rollover Equity in Private Equity Deals 41:49 Key Negotiation Points in Deal Structuring 44:38 Conclusion and Final Thoughts #bosstalk #sellingbusinesses #businesspodcast #businesssales #podcast #bossgroup #businessfinance #businessowner #businessbroker #stocksale #assetsale

    45 min
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About

Jim Parker & Carey Sobel help people buy and sell businesses. Their expertise in this is unmatched, as is their passion for taking great care of all parties involved. This show, Boss Talk: Selling Businesses With Jim Parker and Carey Sobel, is Jim & Carey hashing out what is going on in the world of business brokerage and the best practices that surround getting it right. It's built for business owners to listen and prepare their business to be the best, salable property possible. It's built for business buyers to learn how to identify a good opportunity, offer well, and transition powerfully. This is a show for people who really care to be a part of business transitions in all the right ways.

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