Raising capital for a drinks brand has fundamentally changed — and Mike Solow is on the front lines of that shift.

In this episode of Business of Drinks, we sit down with Mike Solow, Co-Founder & Partner at 99 Proof Partners and Cask Strength, to unpack what founders actually need to know about fundraising right now — from equity vs. debt, to diligence, to investor expectations that most founders underestimate.

99 Proof is a boutique investment firm making early- and mid-stage investments in beverage alcohol, typically writing $500K–$1M checks across equity, debt, and real-estate-backed structures. Cask Strength, their venture-debt arm, focuses on flexible capital solutions — from barrel-backed lending to expansion and production financing — designed to fuel growth without choking a business’s runway.

Mike breaks down why equity capital has become harder to raise, why venture debt is gaining traction, and how valuation resets and shorter hold periods are reshaping the market. He explains what 99 Proof looks for in founders — experience, clarity, grit, and creativity — and why most founders still aren’t prepared for today’s diligence environment.

We also get highly tactical: What makes a deck an automatic “yes” or “no,” why messy storytelling and lack of polish kill opportunities instantly, and how 99 Proof’s publicly shared 40-plus-item diligence checklist is meant to help founders raise smarter capital — even if they never work with 99 Proof.

Mike shares real examples from the portfolio, including why brands like Archer Roose stood out early, how category overlap actually works in portfolio construction, and why “five-year exits” are increasingly unrealistic for most brands today.

The big takeaway: This is a tougher moment — but a healthier one. The correction is rewarding disciplined operators, clear communicators, and founders who understand how capital really works.

If you’re raising money, restructuring capital, or planning your next growth phase, this episode is required listening.

Don’t miss our next episode, dropping on January 14.

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Erica Duecy, co-host: Erica Duecy is founder and co-host of Business of Drinks and one of the drinks industry’s most accomplished digital and content strategists. She runs the consultancy and advisory arm of Business of Drinks and has built publishing and marketing programs for Drizly, VinePair, SevenFifty, and other hospitality and drinks tech companies.

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Scott Rosenbaum, co-host: Scott Rosenbaum is co-host of Business of Drinks and a veteran strategist and analyst with deep experience building drinks portfolios. Most recently, he was the Portfolio Development Director at Distill Ventures. Prior to that, he was the Vice President of T. Edward Wines & Spirits, a New York-based importer and distributor.

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Caroline Lamb, contributor: Caroline is a producer and on-air contributor at Business of Drinks and a key account sales and marketing specialist at AHD Vintners, a Michigan-based importer and distributor.

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Instagram @borkaline

If you enjoyed today’s conversation, follow Business of Drinks wherever you’re listening, and don’t forget to rate and review us. Your support helps us reach new listeners passionate about the drinks industry. Thank you!

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