Deal Playbook with Tom Shipley

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 ou...

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....

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). Chri...

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,...

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 businesses Bankruptcy Divorce Homelessness And the exact lessons that rebuilt his life and for...

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 c...

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...

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 pl...

This episode features JC Hite, founder of Hite Digital, sharing how he disrupted the traditional digital agency model by blending franchising with global talent acquisition. JC recounts his evolution from a white-label provider to building one of the fastest-growing agency networks, spanning 16 offices across the U.S. and Latin America. You will gain insights into how focusing on integrity, premiu...

Brian Burt, founder of Canopy Management, shares his incredible journey from a scrappy Amazon seller to leading one of the fastest-growing e-commerce agencies in the country. Brian breaks down the strategic role acquisitions played in scaling his business, revealing how buying companies unlocked massive growth opportunities. From leveraging TikTok Shop's powerful affiliate network to designing inn...

Robyn Siers is a seasoned M&A attorney telling you her insights on what it takes to successfully navigate mergers and acquisitions, especially in the marketing and tech industries. She talks about the importance of having a clear buying thesis, understanding seller motivation, and using creative deal structures to close deals. Robyn also discusses how AI is becoming part of the M&A world a...

Molly Pittman, CEO and Managing Partner at Smart Marketer, shares her proven strategies for growing businesses in today’s rapidly changing digital marketing landscape. Due to how she helps brands scale from $5 million to $50 million, Molly talks about the importance of strong offers, using native ads, and thinking big-picture when navigating market shifts. She also discusses why many brands are st...

Todd Taskey discusses the key strategies digital marketing agencies need to know when preparing for a successful exit. He explains why finding the right buyer matters more than you think and how clear messaging about your business can drive up your transaction value. Todd also covers the importance of realistic projections, navigating earn-outs, and the factors that can either help or hurt your ch...

Jason Swenk breaks down how agency owners can scale their businesses, overcome common challenges, and position themselves for success. He shares his Eight System Framework, which has helped countless agencies grow from scratch to eight figures. Jason also dives into the power of strategic acquisitions, the importance of having a clear vision, and why most agencies fail to get the right clients. Wh...

Josh Snow shares how he built a multi-million dollar brand by tapping into the power of TikTok and leveraging an army of creators. He explains the strategies that helped him generate $1 million in sales within days of launching on TikTok Shop and how this platform has become a game changer for e-commerce. Josh breaks down the importance of viral content, affiliate marketing, and how TikTok’s uniqu...

Rudy Mawer shares his journey of building multimillion-dollar businesses through strategic partnerships, celebrity collaborations, and leveraging AI and automation. Rudy shares insights on acquiring iconic brands during the COVID-19 pandemic, his strategic partnership with Ty Lopez, and building multi-million dollar businesses while running an expansive agency. He reveals his innovative approach t...

Joshua B. Lee, known as the "Dopamine Dealer of LinkedIn," shares how he’s helped businesses scale by focusing on authentic human connections. He talks about the evolution from MySpace to LinkedIn, revealing why personal brands are critical for business success today. Joshua talks about content strategies that work on LinkedIn, the importance of trust in business deals, and how AI is shaping the f...

In this episode, Erik Huberman, founder and CEO of Hawke Media, shares his entrepreneurial journey, from starting his first business at age six to building a marketing empire that has generated over $2.9 billion in revenue for clients. He opens up about the highs and lows of running a business, including how mental health challenges nearly led him to quit. Erik also breaks down his approach to sca...

Max Finn shares his journey from early success with Facebook marketing to leading the charge on TikTok. He discusses the mindset shift required to approach deals with confidence, the importance of having options, and the fine line between abundance and scarcity in negotiations. Max also talks about key strategies for leveraging media to raise capital and the value of knowing when to walk away from...

Tom Shipley and Matt Bodnar break down the world of business valuations and deal structures. They talk about how valuations are more an art than a strict science, influenced by market conditions, negotiation strategies, and individual motivations. Their discussion covers examples of how businesses are bought and sold, highlighting the strategies that can make or break a deal. With case studies and...

Digital marketing pioneer Dennis Yu shares his expert advice on how businesses can amplify their success by focusing on what works and scaling those wins. From his proven Dollar-a-Day strategy to the power of the Lighthouse model, Dennis breaks down steps for growing agencies and boosting client results. Whether you're running local campaigns or working with global brands, this conversation offers...

Tom Shipley and Matt Bodnar discuss the often-overlooked strategies for sourcing acquisition opportunities that go beyond traditional methods. They challenge the common reliance on brokers and competitive marketplaces, advocating instead for the power of off-market deals and the value of weak ties in your network. Tom and Matt provide simple and effective steps to consistently generate high-qualit...

This episode breaks down the immense potential that agencies and e-commerce brands hold for strategic acquisitions. Tom and Matt share their insights on why these sectors are prime for investment, highlighting the overlooked opportunities that many business owners miss. They argue that now is the time to capitalize on these opportunities, with a focus on the untapped potential in smaller agencies...

Tom Shipley and Matt Bodnar discuss the power of acquisitions as a growth strategy that can outpace run-of-the-mill methods. They share how even in the face of financial hardship, strategic acquisitions allowed their businesses to break through barriers that would have been almost impossible otherwise. They push back against the traditional strategies, showing that buying the right company at the...