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:

1. Why storytelling is the #1 skill in entrepreneurship, fundraising, and hiring
2. The inside story of investing early in unicorn Ollipop
3. How Barrel Ventures evaluates founders, teams, and grit
4. Why family offices behave differently than VCs
5. How to find and pitch family offices for acquisitions and rollups
6. Portfolio strategy, power laws, and identifying future breakout companies
7. How to think about rollups in industries like distribution, HVAC, CPG, and more
8. What makes a founder fundable (and what kills deals fast)

Perfect for founders, CEOs, dealmakers, and anyone raising capital or scaling through acquisitions.

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:

1. Three failed businesses
2. Bankruptcy
3. Divorce
4. Homelessness
5. And the exact lessons that rebuilt his life and fortune

We break down:

1. Why 95% of businesses exit involuntarily
2. The three types of exits every founder faces: involuntary, dictated, and custom-tailored
3. How private equity really buys companies — and how founders get trapped
4. Why “everybody exits” should shape every decision you make today
5. How to build on two tracks: cash flow now and exit leverage later
6. The 52-week exit prep system Jason uses in his own acquisitions
7. Due diligence mistakes that cost founders millions
8. How culture, certainty, and leadership decide post-acquisition success
9. Why 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.

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.

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 yourself
• How private equity really values a business
• Why consolidation forces you to choose: roller, roll-in, or get rolled
• The simple mistakes that torpedo deals (family lawyers, fantasy multiples, hiding issues)
• How to structure deals that close now and true-up later
• Why 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.

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.

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, premium talent, and scalable systems helped him stand out in a competitive industry. From overcoming challenges in leadership to transforming his team’s approach to growth, JC offers advice for entrepreneurs looking to scale with intention and impact.

Chapters:

• 00:00:00 - Why Entrepreneurs Thrive with Their Own Systems
• 00:00:49 - Meet JC Hite: Transforming Agencies Through Innovation
• 00:01:41 - How Hite Digital Scaled to 16 Offices in Record Time
• 00:02:48 - Evolution of Business Models: From White Label to Franchise
• 00:04:52 - Building a High-Performance Team in Latin America
• 00:07:49 - Navigating Cultural Challenges and Staying True to Core Values
• 00:11:16 - Taking the Leap: Starting a Business from Scratch
• 00:14:50 - Why the Franchise Model Simplified Growth and Increased Revenue
• 00:18:27 - Overcoming Client Issues with Long-Term Partnerships
• 00:20:14 - How JC Recruited and Retained Franchise Partners
• 00:21:33 - The Downside of Entrepreneurial Freedom in Franchises
• 00:27:32 - Pioneering a New Business Model: Equity and Rev-Share Partnerships
• 00:29:06 - Breaking Down Equity and Profit-Sharing Deals for Growth
• 00:35:37 - Closing Thoughts and an Invitation to Future Events

Links and Resources

• The Hites
• JC on LinkedIn
• JC on Instagram
• Hite Digital 
• Scale with Stability
• Digital Agency Hacker by JC Hite
• The Hites on YouTube
• Tom Shipley 
• Tom on LinkedIn
• Agency Ventures Aggregator 

Thanks so much for joining us this week. Want to subscribe to Deal Playbook? Have some feedback you’d like to share? Connect with us on Spotify, Apple Podcasts and YouTube to leave us a review!

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 innovative pricing models, Brian offers game-changing insights into building multi-platform success. Whether you're an e-commerce entrepreneur or a growth strategist, this episode is packed with actionable takeaways on scaling fast, fostering client relationships, and staying ahead in the ever-evolving digital landscape.

Chapters

• 00:00:00 – Unlocking TikTok Shop Success: How Affiliates are Changing the Game
• 00:01:00 – Meet Brian Burt: From Scrappy Startup to Scaling E-commerce Empires
• 00:02:00 – Building Canopy Management: Lessons from Growing a Multi-Platform Agency
• 00:04:05 – The Power of Acquisitions: How Strategic Buys Built Canopy’s Backbone
• 00:06:54 – Innovating Pricing Models: Creating Win-Win Client Success Stories
• 00:13:41 – Relationships and Vision: Brian’s Path to Long-Term Growth and Future Plans
• 00:15:34 – Final Takeaways: What’s Next for E-commerce Titans and Industry Disruptors

Links and Resources

• Brian on LinkedIn
• Canopy Management
• Tom Shipley 
• Tom on LinkedIn
• Agency Ventures Aggregator 

Thanks so much for joining us this week. Want to subscribe to Deal Playbook? Have some feedback you’d like to share? Connect with us on Spotify, Apple Podcasts and YouTube to leave us a review!

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 and why building a repeatable process can make transactions smoother and faster. With over 100 deals a year, Robyn offers up advice for buyers and sellers looking to make smart decisions.

Chapters:

• 00:00:00 – Nailing the Buying Thesis: Say No to the Wrong Deals
• 00:01:00 – Robyn Siers on M&A Mastery: Why Experience Matters
• 00:02:30 – Top Advice for Entrepreneurs Navigating Their First M&A Deal
• 00:03:15 – Is AI Part of Your Buying Thesis? The Future of Acquisitions
• 00:05:00 – How Seller Motivation Can Make or Break Your Deal
• 00:07:45 – Creative Deal Structures: Getting More Than Just Cash Upfront
• 00:18:00 – M&A Nightmares: The Challenges of Closing Tough Deals
• 00:21:30 – Wrapping Up with Robyn: What to Expect at DealCon

Links and Resources:

• Robyn on LinkedIn
• JonesSpross
• Tom Shipley 
• Tom on LinkedIn
• Agency Ventures Aggregator 

Thanks so much for joining us this week. Want to subscribe to Deal Playbook? Have some feedback you’d like to share? Connect with us on Spotify, Apple Podcasts and YouTube to leave us a review!

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 struggling while others are thriving, how to measure success in a world with less data, and the role acquisitions can play in growth. Whether you're an agency owner or a business looking to scale, Molly's insights offer practical, actionable advice for winning in 2024.

Chapters

• 00:00:00 - How Data-Driven Decisions Shape Success
• 00:01:00 - Meet Molly Pittman: From Intern to Industry Icon
• 00:02:30 - Surviving Market Shifts: Insights from the Field
• 00:05:10 - Smart Growth Strategies for Scaling Your Business
• 00:06:50 - Deep Dive: The Latest Paid Media Analysis
• 00:08:30 - Offers That Win: Reinventing Business Models
• 00:11:45 - Mastering Content & Personal Branding for Growth
• 00:15:20 - Native Ads vs. Non-Native Ads: What Actually Works
• 00:19:10 - Future Trends in E-Commerce and Digital Marketing
• 00:20:30 - Attribution & ROI: The Ultimate Guide to Measuring Success
• 00:22:50 - Scaling Up with Acquisitions & Lead Generation
• 00:24:30 - Closing Thoughts: Simplifying for Success

Links and Resources

• Molly Pittman
• Molly on LinkedIn
• Molly’s LinkTree 
• Molly on Instagram 
• Smart Marketer 
• Smart Marketer Podcast 
• Tom Shipley 
• Tom on LinkedIn
• Agency Ventures Aggregator 

Thanks so much for joining us this week. Want to subscribe to Deal Playbook? Have some feedback you’d like to share? Connect with us on Spotify, Apple Podcasts and YouTube to leave us a review!

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 chances of closing a good deal. With examples, including a case study on Social SEO’s 8X growth, this episode is packed with advice for agency owners looking to sell.

Chapters

• 00:00:00 - Kickoff: Making Partners as Happy as Customers
• 00:00:53 - Meet Todd Taskey: Maximizing Digital Marketing Exits
• 00:01:54 - The Top Advice for Agencies Eyeing an Exit
• 00:02:15 - Aligning with the Right Buyer for Lasting Success
• 00:03:38 - How Social SEO Scaled 8X with Private Equity
• 00:04:46 - EBITDA Demystified: Boosting Your Transaction Value
• 00:10:24 - The Power of Realistic Projections in Business Deals
• 00:11:56 - Earn-Outs and Retention: How to Stay in Control
• 00:17:20 - Navigating Market Trends & What They Mean for Agencies
• 00:23:28 - Secrets to Client Retention: Don’t Let Them Walk
• 00:33:19 - Final Prep: How to Ensure a Successful Business Exit

Links and Resources:

• Todd on LinkedIn 
• Second Bite Podcast
• Potomac Business Capital
• Tom Shipley 
• Tom on LinkedIn
• Agency Ventures Aggregator 

Thanks so much for joining us this week. Want to subscribe to Deal Playbook? Have some feedback you’d like to share? Connect with us on Spotify, Apple Podcasts and YouTube to leave us a review!