Deal Playbook with Tom Shipley

Welcome to The Deal Playbook Podcast — the ultimate show for entrepreneurs, CEOs, and founders who want to scale their businesses, diversify risks, and unlock multiple exit opportunities through strategic acquisitions and deals. Hosted by Tom Shipley, an experienced entrepreneur with 18 successful acquisitions and exits, this podcast offers invaluable insights into the world of M&A. Each episode features expert guests who share their knowledge on how to identify once-in-a-lifetime deals, navigate the acquisition process, and engineer lucrative exits.Discover how top business leaders overcame their toughest challenges, maximized wealth, and turned obstacles into opportunities. Whether you're looking to scale your company, explore exit strategies, or learn from others' successes and failures, this podcast is packed with actionable advice, practical tips, and inspiring stories. Tune in to The Deal Playbook Podcast to sharpen your business acumen and accelerate your path to a successful e

Deal Playbook with Tom Shipley is a business podcast hosted by Tom Shipley, with 24 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Tom Shipley hosts Deal Playbook with Tom Shipley, a business show with 24 episodes published.

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  Episode #24

  Add a Zero: How Acquisitions Collapse Time for Founders with Callum Laing

  Apr 2, 202639 minS0

  <p>Most entrepreneurs are taught to build everything from scratch.I lived that path.</p><p>It’s slow.</p><p>It’s painful.</p><p>And eventually, it hits a ceiling.</p><p>In this interview with Callum Laing, I share why acquisitions became the single biggest force multiplier in my career—and how they’ve allowed me to scale faster, reduce risk, and think like a CEO instead of a grinder.</p><p>I walk through real stories: running out of money, hitting walls, facing breakdowns, and making the decision to buy instead of build when it mattered most.We...

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  Episode #23

  The Mind Behind $75 Billion in Growth: Jay Abraham on Preeminence, Force Multipliers, and Exponential Scale

  Mar 19, 202651 minS0

  <p>In this episode of Deal Playbook, I sit down with Jay Abraham, the most trusted strategic mind in modern business and the force behind over $75 billion in growth across 10,000+ companies.</p><p>Jay doesn’t talk tactics. He talks leverage.</p><p>We break down why most businesses stay stuck in incremental growth, how elite operators engineer exponential upside, and why strategy—not effort—is the real unlock. Jay walks through his philosophy of Preeminence, revenue geometry, force multipliers, and how the smartest founders scale without betting the company on risky moonshots.</p><p>This is a masterclass in how to...

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  Episode #22

  Mastering Wealth & Financial Freedom: Tax Leverage Strategies to Scale Your Business (Without Outside Capital) with Chris Jarvis

  Mar 5, 202636 minS0

  <p>In this episode of Deal Playbook, I sit down with Chris Jarvis, financial fixer, wealth strategist, TED speaker, and author, to break down what most founders miss about building real wealth.</p><p>We go straight at the trap: the “comfortable” $300K–$500K income that quietly becomes a ceiling… and the fairy tale that your business sale will be the payday (when most businesses never actually sell).</p><p>Chris explains how the real game is structure, how to redesign entities, cashflow, and tax exposure so you can fund growth from money that would’ve gone to the IRS. We talk C...

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  Episode #21

  How Venture Capital Really Works: Storytelling, Unicorn Investing & Family Office Strategy with Nate Cooper

  Jan 29, 202630 minS0

  <p>Venture capital isn’t luck. It’s pattern recognition, storytelling, and backing founders who refuse to quit.</p><p>In this episode, I sit down with Nate Cooper, Founder & Managing Partner of Barrel Ventures, an early-stage VC fund behind breakout brands including the unicorn beverage giant Ollipop.</p><p>Nate shares the inside story of writing the first check into Ollipop before it hit a grocery shelf, how the company scaled to a multi-billion-dollar valuation, and what he looks for when evaluating early-stage founders.</p><p>You’ll also learn how family offices operate, why they differ from traditional VC, an...

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  Episode #20

  Everybody Exits: Ethical Capitalism Is How You Control It with Jason Sisneros on M&A, Due Diligence & Building to Exit

  Jan 21, 202651 minS0

  <p>Everybody exits.</p><p>The only question is how.</p><p>In this episode, I sit down with Jason Sisneros — serial acquirer, operator, and creator of the Built-to-Exit system — for a raw, unfiltered conversation on business failure, acquisitions, exits, and ethical capitalism.</p><p>Jason shares his real story:</p>Three failed businessesBankruptcyDivorceHomelessnessAnd the exact lessons that rebuilt his life and fortune<br/><p>We break down:</p>Why 95% of businesses exit involuntarilyThe three types of exits every founder faces: involuntary, dictated, and custom-tailoredHow private equity really buys companies — and how founders get trappedWhy “everybody exits” should shape every decision y...

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