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.
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.
19 Mar 2026
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 have
Turn partnerships, JVs, and acquisitions into growth accelerants
Escape the “incremental trap” and enter the exponential zone
Think like private equity before private equity shows up
Build 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/ (https://ai.abraham.com/)
5 Mar 2026
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 risky
How entity structure can create more free cashflow without outside capital
The C-Corp “double tax” misconception and the math that flips it
How 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.
Who has been a guest on Deal Playbook with Tom Shipley
Names identified in recent episode analyses. Showing up to five guests.
Nate Cooper
Jason Cisneros
Carrie Kerpen
Robert Glazer
Brett Hurt
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
1 ratings
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Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about Deal Playbook with Tom Shipley
Who hosts Deal Playbook with Tom Shipley?
Tom Shipley host the show. Published by Tom Shipley.
How often do new episodes come out?
The show publishes weekly, based on its RSS feed.
Does Deal Playbook with Tom Shipley take guests?
Yes. Guests have been identified in episode analyses.
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