Deal Playbook with Tom Shipley

Tom Shipley
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

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 exit. Ideal for anyone searching for expert guidance on mergers, acquisitions, and business exits.

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

    Apr 2

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

    Most entrepreneurs are taught to build everything from scratch.I lived that path. It’s slow. It’s painful. And eventually, it hits a ceiling. 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. 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 talk about: - Why organic growth eventually stalls - How acquisitions solve real business problems - The “add a zero” mindset that forces better decisions - Turning breakdowns into breakthroughs - Why trust, timing, and people matter more than deal mechanics If you’re a founder doing $1M–$100M and thinking seriously about your next chapter, this episode will challenge how you see growth, leverage, and risk.

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

    Mar 19

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

    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. Jay doesn’t talk tactics. He talks leverage. 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. This is a masterclass in how to: Demand more yield from everything you already haveTurn partnerships, JVs, and acquisitions into growth accelerantsEscape the “incremental trap” and enter the exponential zoneThink like private equity before private equity shows upBuild dominance without adding risk, capital, or complexity If you’re a founder doing $1M–$100M and looking for unfair advantages, this episode will permanently upgrade how you think about growth. If you want to gain access to the Jay-I, you can do so here: https://ai.abraham.com/

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

    Mar 5

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

    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. 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). 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-Corps, “double taxation” myths, entity layering, and why the right setup can create an immediate EBITDA lift and unlock capital for hiring, tech, and acquisitions. What you’ll learn: Why most “organic growth” plans stall (and what to change drastically)The harsh reality of exits and why banking on a sale is riskyHow entity structure can create more free cashflow without outside capitalThe C-Corp “double tax” misconception and the math that flips itHow founders turn tax savings into a scaling engine (operators become architects) If you’re doing $300K–$1M+ in profit and still feel cash-constrained, this episode will change how you think about growth.

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

    Jan 29

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

    Venture capital isn’t luck. It’s pattern recognition, storytelling, and backing founders who refuse to quit. 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. 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. You’ll also learn how family offices operate, why they differ from traditional VC, and how founders can partner with them for rollups, acquisitions, and long-term growth. From venture portfolio construction to rollup strategies and founder psychology, this conversation is a masterclass in how real investors make decisions. Topics We Covered: Why storytelling is the #1 skill in entrepreneurship, fundraising, and hiringThe inside story of investing early in unicorn OllipopHow Barrel Ventures evaluates founders, teams, and gritWhy family offices behave differently than VCsHow to find and pitch family offices for acquisitions and rollupsPortfolio strategy, power laws, and identifying future breakout companiesHow to think about rollups in industries like distribution, HVAC, CPG, and moreWhat makes a founder fundable (and what kills deals fast) Perfect for founders, CEOs, dealmakers, and anyone raising capital or scaling through acquisitions.

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

    Jan 21

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

    Everybody exits. The only question is how. 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. Jason shares his real story: Three failed businessesBankruptcyDivorceHomelessnessAnd the exact lessons that rebuilt his life and fortune We break down: 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 you make todayHow to build on two tracks: cash flow now and exit leverage laterThe 52-week exit prep system Jason uses in his own acquisitionsDue diligence mistakes that cost founders millionsHow culture, certainty, and leadership decide post-acquisition successWhy business is a machine — not your identity This episode is for founders doing $1M–$100M, operators considering acquisitions, and CEOs who want to collapse time, avoid bad exits, and play offense. If you’re buying, selling, or scaling through M&A, this conversation will permanently change how you think about business.

    51 min
  6. Building, Exiting, and Leading: Empowering Women to Win in Business Exits with Carrie Kerpen

    Jan 2

    Building, Exiting, and Leading: Empowering Women to Win in Business Exits with Carrie Kerpen

    Women are starting businesses at twice the rate of the rest of the population but they’re still massively underserved when it comes to acquisition strategy, exit preparation, and deal-making clarity. Carrie Kerpen is changing that. In this episode of The Deal Playbook Podcast, I sit down with Carrie, founder of Likeable Media, exited agency CEO, and now founder of The Whisper Group, a powerful collective built to help women navigate exits, acquisitions, and strategic growth from a position of strength. Carrie built one of the first social media agencies, grew it through industry upheaval, and sold at the height of the 2021 market. Now, she’s helping women founders step into the rooms, conversations, and opportunities they’ve historically been shut out of, with the frameworks and confidence to win. Inside this episode, we break down: • Why female founders need tailored exit strategy support, and why most don’t get it • How women can use acquisitions to scale faster, strengthen their position, and increase exit value • The “personal readiness” factor, especially critical for women balancing multiple roles • How diverse-led companies often outperform (and why they’re strong acquisition targets) • Why women tend to underestimate projections and how to use that to build trust in deals • How to reduce founder dependence and build true enterprise value • What it takes to own your narrative, elevate your secret sauce, and shift from transactional exits to transformational ones Carrie also unpacks her WHISPER Framework that has helped dozens of women founders prepare for exits, acquire businesses, or step into a bigger vision for their company and their wealth. This is more than an interview, it’s a roadmap for women who want to build optionality, negotiate from strength, and lead their next chapter on their terms. If you’re a woman founder, or you lead alongside them, this episode will change how you think about exits, acquisitions, and the leverage you already have.

    46 min
  7. How Agencies Scale Through Acquisitions: Valuation, Timing & PE Strategy with Bob Glazer

    12/14/2025

    How Agencies Scale Through Acquisitions: Valuation, Timing & PE Strategy with Bob Glazer

    Most founders grow by effort. The smart ones grow by acquisition. In this episode of The Deal Playbook Podcast, I sat down with Robert Glazer, founder of Acceleration Partners, a 300-person global performance marketing firm that scaled 20–30% a year for a decade and turned into a true acquisition platform. Bob built a real business with real systems, then partnered with private equity and used M&A to accelerate growth. But the reason I brought him on isn't the highlight reel, it's because he’s one of the few operators who tells the truth about valuation, timing, and what actually determines the outcome of a deal. Most founders get this wrong. They confuse a P&L with a bank account. They wait for the “perfect year.” They misread the market. And by the time they’re ready to sell, the window has already closed. Bob breaks it down with clarity and data: When to sell and when you’re lying to yourselfHow private equity really values a businessWhy consolidation forces you to choose: roller, roll-in, or get rolledThe simple mistakes that torpedo deals (family lawyers, fantasy multiples, hiding issues)How to structure deals that close now and true-up laterWhy AI won’t replace agencies but will replace agency roles He also shares the founder's reality almost no one talks about: when 99% of your wealth sits in one illiquid asset, your “wait another year” strategy is actually a risk strategy, and a dangerous one. If you’re growing a business, thinking about acquisitions, preparing for a sale, or trying to build a platform instead of a practice, this conversation will give you the clarity, frameworks, and mindset to play offense. This is the episode I wish every founder listened to before stepping into a negotiation.

    45 min

  8. 09/06/2025

    Startup to Unicorn IPOs to Leveraging M&A in the AI Era: Brett Hurt’s Playbook

    In this episode of The Deal Playbook, Tom Shipley sits down with Brett Hurt, one of Austin’s most accomplished entrepreneurs and investors. Brett has built and successfully exited three companies, including: Coremetrics (acquired by IBM for ~$300M)Bazaarvoice (scaled to $100M+ ARR and a unicorn IPO in 2012)data.world (a B-Corp acquired by ServiceNow in July 2025 to power their enterprise AI platform) Through Hurt Family Investments, Brett and his wife Deborah have also backed over 146 startups and 47 VC funds, making him a cornerstone of the Austin tech and venture ecosystem. Tom and Brett dive deep into: The buy vs. build rubric and how to know when an acquisition will compound value.Lessons from PowerReviews and Longboard Media acquisitions—what worked, what didn’t, and why.How Bazaarvoice became one of the most capital-efficient SaaS unicorns of its time.Preparing your company for acquisition—what must be true before conversations begin.Why culture is the real integration strategy in M&A.Brett’s perspective on AI, agentic systems, and the future of deal-making.His new mission through Love Conquers Fear—a podcast, book, and holding company aimed at shaping humanity’s future in the AI era. Whether you’re running a 7–9 figure company or planning your first acquisition, this fireside chat is packed with hard-won lessons, cautionary tales, and forward-looking strategies that will help you scale smarter and exit stronger.

    34 min
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About

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 exit. Ideal for anyone searching for expert guidance on mergers, acquisitions, and business exits.

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