The Exit - Presented By Flippa

• Inside the World’s Record $13M Domain Sale with Jeffrey Gabriel

  Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- A quick note on audio: We experienced some technical gremlins with the microphones during this recording. While the sound quality isn't perfect, the quality of the information is 10/10. Is your business sitting on digital gold, or did you buy a liability? In this episode, we sit down with Jeffrey Gabriel, the founder of Saw.com and the man who broke the Guinness World Record for the largest domain sale in history, brokering the sale of a domain for $13 million. Jeff takes us behind the scenes of the high-stakes world of "online real estate." Whether you are a bootstrapper looking for a creative way to secure a premium .com, or an investor looking to understand the wild valuation swings between .net, .ai, and .io, this episode is a masterclass in digital assets. We dive deep into how to value a name, how to negotiate deal structures that require $0 down, and why the "Chinese Chip" market and AI trends are reshaping the internet. In this episode, you’ll learn: The $13M Deal: The true story behind the complex bankruptcy sale. Valuation Framework: The specific metrics Jeff uses to determine if a domain is worth $5,000 or $500,000 (Length, CPC, and Universality). Creative Financing: How to acquire a six-figure domain name using "Earnest Money" and lease-to-own structures, perfect for cash-strapped startups. The TLD Debate: Why .net is the "New Balance" of domains, and when you should actually buy a .ai or .io. Market Trends: From the "Chinese Chip" market to the Crypto crash and the current AI boom. Timestamps: (02:36) From selling loans to selling the internet: Jeff’s entry into the domain space. (11:49) Breaking the World Record: The logistics of selling [suspicious link removed] for $13 Million. (15:32) Business Strategy: Should you buy the .com, .net, or .ai? (20:50) The Friend.com case study: Spending $2M on a domain for viral marketing. (23:51) The Valuation Formula: How to calculate the worth of a URL. (30:29) Deal Structuring: How to use options and milestones to buy domains without full capital upfront. (37:34) The history of domain trends: From Ringtones to Chinese "Chips" to AI. -- Jeffrey M. Gabriel, founder and CEO of Saw.com, is a domain industry veteran with over 15 years of experience and over $550 million in completed transactions. Known for high-profile deals like the Guinness World Record-breaking sale of Sex.com for $13 million, the top .ORG sale of Poker.org for $1 million, and the recent sales of Diamond.com, AI.com, Media.com, Data.ai and countless others. Jeffrey and his team have a reputation for delivering exceptional value to clients. Previously, he held key roles at Uniregistry, Igloo.com, and Sedo. An active industry expert, Jeffrey has contributed to Forbes and is a member of the Internet Commerce Association, frequently sharing insights on domain acquisition, sales, and strategy. Website - https://saw.com/ LinkedIn - https://www.linkedin.com/in/jeffreymgabriel/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

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• Battling Cancer, Buying Out a Co-Founder, and The "Napkin Pitch" Strategy with Chelsea Jones

  Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- What happens when your business explodes with growth at the exact moment your personal life falls apart? In this episode, we sit down with Chelsea Jones, co-founder of Sunny Road, to unpack a journey that defines entrepreneurial resilience. From losing her life savings on a failed MLM venture to building a successful agency during the chaos of COVID, Chelsea’s story is a masterclass in pivoting. We dive deep into the messy reality of agency life, discussing the "dark side" of partnerships, how to navigate a buyout while battling a cancer diagnosis, and the complexities of merging two seven-figure companies. Chelsea also opens up about the "Napkin Pitch" concept and why women entrepreneurs need to stop waiting for perfection and start selling their vision. If you are an agency owner, an e-commerce founder, or an entrepreneur navigating a transition, this episode offers the blueprint for survival and scale. In this episode, we cover: The "Fail Fast" Mentality: Lessons learned from a $5,000 loss and early MLM failure. The COVID Scale-Up: Going from 5 to 32 employees overnight and the operational debt that followed. The Buyout & The Battle: How Chelsea bought out her burning-out partner while simultaneously undergoing cancer treatment. Merging & AI: Navigating a merger between friends and how AI has slashed design fees from six figures to low fives. The "Napkin Pitch": Why you need to run into the room with your idea before it's fully fleshed out. Exit Strategy: How to prepare your books and your mindset for a sale long before you're ready to leave. Key Timestamps: (00:00) Intro (01:55) The $5,000 mistake: Learning from early failure (05:14) Scaling during COVID: Managing rapid growth and team burnout (07:27) The Crucible: Buying out a partner while fighting cancer (10:50) Merging companies and the impact of AI on agency pricing (13:21) How to prepare your financials for a merger or exit (18:15) When is the right time to sell? (20:02) The "Napkin Pitch": Overcoming perfectionism in business (23:38) What Sunny Road does for E-Commerce brands -- Chelsea Jones is a visionary e-commerce leader, Shopify Platinum Partner, and co-founder of Sunny Road. She first built her reputation at Chelsea & Rachel Co., the first women-founded agency to achieve Shopify Premier status, where she created high-performing online stores and became a trusted partner for brands looking to scale. In 2023, she joined forces with Drew Himel of Fireside Digital to launch Sunny Road, a digital agency that blends creative excellence with data-driven growth. Today, Chelsea leads with the same passion and client-first approach that have defined her career, helping brands build e-commerce experiences that shine. Website - https://sunnyroad.co/ LinkedIn - https://www.linkedin.com/in/chelsea-jones101/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

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• Why 50% of Founders Regret Selling (and How to Add 40% to Your Deal Value) with Chris Spratling

  Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- Most business owners believe selling their company is a single event—a signature on a dotted line. But according to Chris Spratling, Founder of Chalk Hill Blue, treating your exit like an event is the fastest way to leave millions on the table. In this episode, we unpack why the "illusion of readiness" kills deal value and why over half of all founders regret their exit within 12 months. Chris shares his experience from the private equity and consulting worlds to explain exactly what modern buyers are looking for. We move beyond basic EBITDA multiples to discuss the psychology of the seller, how to survive forensic due diligence, and the shift from "growth at all costs" to "predictability." If you are building a business with the intention of selling—whether next year or in a decade—this conversation is your blueprint for maximum value and zero regret. In this episode, you will learn: The "Illusion of Readiness": Why having a profitable business does not mean you have a sellable business. The 8-10 Drivers of Value: What acquirers actually look for (hint: it’s not just your bottom line). Deal Structure Strategy: How to align earn-outs, non-competes, and tax efficiency with your personal life goals. The Negotiation Edge: How one seller secured a 40% premium over the initial offer simply by being better prepared than the buyer. Market Shifts: Why post-COVID buyers are paying for predictability over hockey-stick growth. The Regret Trap: Why 50% of owners hate their deal a year later and how to ensure you aren't one of them. -- Timestamps: (01:49) Why selling is a journey, not an event (03:36) The difference between Perceived Value and Market Value (05:56) Seller Readiness vs. Business Readiness (09:21) How to negotiate deal structures and multiple bids (17:55) How buyer psychology has changed in the last 5 years (22:54) The #1 piece of advice: "Prepare like your life depends on it" -- Chris Spratling is the founder of Chalkhill Blue Limited, a leading business coaching and consulting practice that helps UK business owners scale effectively and prepare for profitable exits. With more than 30 years of experience owning, buying, and selling multiple seven-figure businesses, he brings deep, practical insight to every client engagement. He is also the author of The Exit Roadmap: The Insider’s Guide to Selling Your Business Profitably, where he distills his proven approach to exit planning and leadership transformation, including how to understand whether a business is truly sale-ready. Website - https://chalkhillblue.org/ Check out his book - https://a.co/d/cKVGTFs Take the Exit Readiness Survey - https://chalkhillblue.org/exitreadiness-survey -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

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• Smart Scaling, M&A Strategy, and Why Most Founders Raise Money Too Early with James Rose

  Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- If you're an entrepreneur wondering when to raise capital, how to scale through acquisition, or what really drives valuation multiples, this conversation delivers tactical advice you can actually use. In this episode of The Exit Podcast, James Rose, Founder and CEO of Inflective Group, unpacks the strategic decisions that determine whether a business exits successfully or stalls out. James shares hard-won lessons from his journey building and selling businesses across Eastern Europe, spending over a decade in the startup world, and now helping agency founders navigate their own exits. What You'll Learn On Common Founder Mistakes: Why raising money too early can make your business less acquirable The hidden execution risks that come with rapid scaling How hiring the wrong people costs you 18 months and momentum Why one A-player delivers what five B-players struggle to achieve On Exit Timing and Preparation: Why the best businesses get bought, not sold The truth about "exit prep" and when it becomes a distraction How to know if you're actually ready to scale or should stay focused What life-changing money really means at different stages On Scaling and Valuation: Why small operational improvements won't significantly change your multiple The three paths to scale: raising capital, acquiring competitors, or joining a larger group How to think about EBITDA multiples and what actually moves the needle Why scale is the ultimate multiplier, not process optimization On M&A and Deal Structure: How to create competitive tension in negotiations (and why you need it) The "longest list" negotiation strategy that actually works Why most founders focus on the wrong deal terms Red flags to watch for in private equity deals and earnout structures How minority investments can empower founders instead of limiting them On Growing Through Acquisition: The financial commitment calculation: when will you actually see ROI? Managing the distraction of M&A while protecting your core business Why leverage matters more than scale in acquisitions How to ensure people stay and remain motivated post-acquisition -- James Rose is Founder & Director of Rose Equity Partners and also leads as Founder & Group CEO of Inflectiv Group, bringing over two decades of entrepreneurial leadership in launching, scaling and advising high-growth media, marketing and technology ventures. He has driven commercial strategies and go-to-market execution for private-equity-backed companies while taking revenues from early stage through to £7M+ outcomes. With a deep passion for partnering with ambitious entrepreneurs and creating sustainable value, James combines operational expertise, investor insight and strategic vision to help founder-led businesses navigate growth inflection points and deliver meaningful impact. Website - https://www.inflectivgroup.com/ LinkedIn - https://www.linkedin.com/in/jamesroseequitypartners/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

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• How I Bought 20 Companies for £1 (And Why Your Business Might Be Unsellable) - Exit and Acquisition Lessons with Lee Smith

  Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit Podcast, host Steve sits down with Lee Smith, an acquisition entrepreneur at Verdani Capital with 12 years of M&A experience. Lee shares hard-won lessons from acquiring 20+ businesses and reveals what buyers really look for when evaluating companies for acquisition. KEY TOPICS COVERED: The #1 Red Flag Buyers See (And How to Fix It) Lee reveals why owner-dependency kills deals and how to build transferability into your business 2-3 years before exit Inside the Valuation Process Real multiples for blue-collar businesses (2-4x true profit, not EBITDA) and why adjusted earnings can backfire Deal Structure That Works How Lee structures acquisitions to align incentives: buying 60-80% stakes with future upside potential that often doubles the founder's payday The Biggest Deal Mistakes From buying distressed companies to discovering hidden equity agreements 30 minutes before closing—lessons learned the hard way The £1 Business Acquisition Strategy How Lee has purchased 20 businesses for just one pound, including a remarkable turnaround that saved a founder from £500K in debt When Concentration Risk Isn't a Deal-Breaker Strategic approaches to handling clients that represent 60-70% of revenue, including key customer clauses in SPAs Building Trust in M&A Deals Why "two ears, one mouth" matters more than spreadsheets when structuring successful acquisitions The EOS Framework for Integration Using simple systems to manage acquired businesses without disrupting teams or culture -- Lee Smith is a values-driven entrepreneur and dealmaker with more than 25 years of experience and a respected track record in UK M&A. After completing his first acquisitions in 2014, he went on to buy and turn around nine underperforming companies before founding Verdani Capital, where he continues to acquire and scale larger UK businesses. To date, Lee has completed 26 acquisitions across sectors such as Manufacturing, Professional Services, Construction, HVAC, and IT Services, supported by training from leading M&A mentors in the UK and US. His current portfolio generates over £2M in annual profit with a clear path toward £10M, strengthened by three strategic exits in 2024. Grounded in spirituality and conscious leadership, Lee combines substance, strategy, and long-term thinking in every partnership. Website - https://www.leeasmith.co.uk/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/

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