Powered by RND
PodcastsTechnologyThe Exit - Presented By Flippa

The Exit - Presented By Flippa

The Exit - Presented By Flippa
The Exit - Presented By Flippa
Latest episode

Available Episodes

5 of 272
  • 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/
    --------  
    34:25
  • 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/
    --------  
    28:45
  • 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/
    --------  
    32:37
  • You Just Sold Your Business. Now What the Hell Do You Do? Common Mistakes Entrepreneurs Make with Carolyn Nolan
    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 founders obsess over the deal - valuations, terms, negotiations. But few ever ask the most important question: What comes next for you? In this episode of The Exit, Steve chats with Carolyn Nolan, CEO and Private Wealth Advisor at TNG Private Wealth, about what really happens after you sell. From emotional comedowns to tax traps, Carolyn reveals why the money is actually the easy part—and how to build a life that’s just as successful as your exit. 🎯 Key Takeaways: Why entrepreneurs struggle to “switch off” after selling The one question that reframes your entire next chapter The two extremes that destroy post-exit happiness Avoiding the tax blindside that catches almost everyone “Workhorse vs. racehorse” investing explained Why your discretionary expenses probably aren’t Passing wealth down—without raising entitled kids The surprising loneliness that follows exits ⚠️ Common Post-Exit Mistakes: Ignoring tax implications Overspending on real estate Gifting too early Freezing up and spending nothing out of guilt Waiting until after the exit to plan your life -- Carolyn Nolan’s superpower is igniting positive energy and meaningful action by brainstorming what could be, unapologetically speaking her truth, and creating tools for the taking in her ‘CNo toolbox’. She helps people stay strategically prepared, simplify life’s juggling act, and embrace change with confidence, inspiration, and a sense of adventure. LinkedIn - https://www.linkedin.com/in/carolynlaunienolan/ Website - https://www.ameripriseadvisors.com/team/tng-private-wealth/ -- 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/
    --------  
    30:56
  • From Startups to the Stock Exchange: How Callum Laing Took 100 Companies Public and Redefined the Exit Gam
    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, host Steve sits down with Callum Laing, partner at Unity Group, author, and serial entrepreneur who has helped take more than 100 companies public. With decades of experience across Asia, Europe, and beyond, Callum shares his contrarian approach to growth, exits, and how founders can use the capital markets as a scaling tool, not just a finish line. From his first recruitment business during the dot-com boom to running a global group that helps small businesses access public market advantages. Callum has seen it all, from booms, busts to breakthroughs. He explains why most entrepreneurs under-optimize for profit when gearing up to sell, how boards can fast-track business maturity, and why timing the market is less about prediction and more about preparation. Callum’s insights extend beyond valuation multiples. He talks candidly about common M&A mistakes, the power of strategic positioning, and why founders should sell “as soon as they can” to regain their most valuable resources: time and capital. This episode is a masterclass in scaling smart, negotiating with leverage, and learning faster through failure. -- Callum Laing is a seasoned entrepreneur, investor, and M&A specialist with over two decades of experience building and scaling companies across multiple industries. As a Partner at Unity Group and Founder of the Global Investment Leaders Directive (GILD) and the Veblen Director Programme, he helps business owners unlock liquidity, accelerate growth, and gain access to global capital markets. A passionate advocate for ethical capitalism and entrepreneur-led innovation, Callum has worked extensively with private equity firms, family offices, and public markets to bridge the gap between fast-growing private enterprises and institutional investors. LinkedIn - https://www.linkedin.com/in/callumlaing/ Website - https://callumlaing.com/ -- 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/
    --------  
    33:28

More Technology podcasts

About The Exit - Presented By Flippa

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 https://flippa.com/the-exit-podcast/
Podcast website

Listen to The Exit - Presented By Flippa, Deep Questions with Cal Newport and many other podcasts from around the world with the radio.net app

Get the free radio.net app

  • Stations and podcasts to bookmark
  • Stream via Wi-Fi or Bluetooth
  • Supports Carplay & Android Auto
  • Many other app features
Social
v8.0.7 | © 2007-2025 radio.de GmbH
Generated: 12/6/2025 - 10:11:49 PM