The Exit - Presented By Flippa

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 -- Are you trying to grow your business by 10% year over year? You might be leaving massive wealth on the table. In this episode, we sit down with Tom Shipley, a former Special Forces operator turned serial entrepreneur and aggressive investor. Tom challenges the traditional startup narrative with a shocking reality: Growing organically might increase your value by 50% over five years, but buying competitors can increase it by 1,200%. Tom shares his incredible journey from the dot-com bust, where he was days away from missing payroll, to buying a $15M division of Boise Cascade without using his own capital. We unpack the "Programmatic M&A" playbook, how to use acquisitions to solve operational weaknesses, and why the best path to a massive exit is often buying your way there. -- Tom Shipley is a serial entrepreneur and M&A strategist known for creating the “Add a Zero” growth philosophy, which helps founders rapidly scale their businesses through strategic acquisitions. From his early career as an IDF special forces operator to building and advising brands that have generated more than $2 billion in revenue, Tom brings a rare combination of disciplined execution and bold dealmaking. A pioneer of programmatic M&A for mid-market companies, he has raised over $100 million, led multiple acquisition platforms, and now teaches 7 to 9 figure founders how to accelerate growth, close capability gaps, and engineer premium exits through smart, repeatable deals. Websites - https://www.tshipley.com/ - https://dealconlive.com/ LinkedIn - https://www.linkedin.com/in/t-shipley/ Time Stamps: 00:00 - Intro 02:47 - Buying a division of a Fortune 500 company without cash 05:05 - Scaling a beauty brand from $30k to $100M+ via acquisition 08:09 - How Mezzanine debt works (and why it’s better than pure equity) 12:51 - The Golden Stat: 50% vs. 1,200% Enterprise Value growth 17:58 - The thought exercise that will force you to raise your prices today 20:41 - The biggest mistakes entrepreneurs make when selling 24:14 - Why "Day One" after closing is the most dangerous time 27:31 - What is Programmatic M&A? -- 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/

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 -- Are you running your business, or is it running you? In this episode, we sit down with Alexis Sikorsky, co-founder of Nightscale, who reveals the brutal truth about the "Grind" and the specific strategies he used to exit his banking software company for a massive multiple. If you are a founder stuck at the $5M–$10M revenue plateau, this episode is a masterclass in cashing out. Alexis breaks down the "$50 Million Mistake", a calculation of the money and time he lost by not knowing the secrets of Private Equity earlier, and how you can avoid it. What You’ll Learn: The "Fish and Chip" Trap: How Private Equity firms lure founders with high valuations only to chip away at the price during due diligence—and how to stop them. Nominal EBITDA vs. EBITDA: The financial metric that matters more than your bottom line. Learn how "dressing the bride" and identifying add-backs can instantly increase your valuation. The Magic Number: Why a $40M valuation is the specific target for a lifestyle where you never have to touch your capital again. The Due Diligence Reverse Card: How to investigate a PE firm by calling the founders they don't want you to talk to. Escaping the Operator Trap: Why you need to fire yourself from day-to-day operations to make your company sellable. -- Alexis Sikorsky is a seasoned entrepreneur, strategic advisor, and #1 international best-selling author who helps founders and SMEs scale with confidence, make smarter strategic decisions, and prepare for long-term growth and successful exits. Over his career, he has founded, scaled, and led multiple companies, including building and selling a software business to private equity in a nine-figure transaction. He is the founder of Sikorsky Consulting Ltd. and a co-founder of KnightScale Partners, where he works closely with founders as a true operator partner, providing experienced, founder-to-founder guidance on scaling, leadership, and value creation. Holding an EMBA from Oxford University, Alexis blends real-world entrepreneurial experience with strategic insight to help business owners future-proof their companies and navigate critical inflection points. Website - https://www.knightscalepartners.com/ LinkedIn - https://www.linkedin.com/in/alexis-sikorsky-consulting/ -- Time Stamps: (01:11) Surviving the 2008 crash: Losing 75% of revenue overnight. (03:46) The "Unbelievable" Offer: Selling for 11x EBITDA based on a future plan. (06:00) Calculating the $50 Million / 5-Year Mistake. (08:59) When is the right time to sell? (The mathematics of the exit). (14:00) Red Flags: Detecting the "Fish and Chip" strategy. (20:30) How to boost valuation using Nominal EBITDA and non-recurring costs. (27:30) Why you should do M&A earlier than you think. -- 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/

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/

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/

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/