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.