Wish You were Here!
At 21 Hats Live, we don't drink just any bourbon.
Good morning!
Here are today’s highlights:
It was another smart, insightful, moving, delicious day of 21 Hats Live.
On this week’s Dashboard, Hannah Sandmeyer explains how her startup, Steward Market, helps business owners achieve better exits.
21 Hats Live: Cincinnati
On Thursday, the 21 Hats Live crew visited New Riff Distilling, which is right across the river in Newport, Ky. and which was recently awarded the honor of World’s Best Bourbon. No arguments here. We met with Molly Lewis, president of New Riff, who explained why the business is thriving at time when many distilleries are struggling. It has to do with smart pricing, a multifaceted business model, and a special water aquifer.
THE 21 HATS PODCAST: DASHBOARD
The Anti-PE Marketplace: Hannah Sandmeyer spent years acquiring ecommerce businesses for an Amazon aggregator, giving her a front-row seat to how deals get done—and what often gets lost in the process. Too many owners, she came to believe, are forced to choose between shutting down their businesses or selling to buyers whose priorities may have little to do with preserving the company, the culture, or the people who built it. So she decided to build an alternative. Hannah is now founder and CEO of Steward Market, which she describes as “the first marketplace for ethical exits.”
In this week’s Dashboard, she explains what makes an exit “ethical,” why some owners are actively looking for alternatives to private equity, and how Steward Market hopes to connect values-driven sellers with buyers who want to continue what those owners have built—not simply maximize short-term returns. She also explains why the company chose a business model that doesn’t rely on taking commissions from deals.
You can subscribe to the 21 Hats Podcast—brought to you by Grasshopper Bank—wherever you get podcasts.
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FinTeam Business Consulting: Complimentary Drake Check for 21 Hats readers. “How is my business actually doing?” We heard that question so often from business owners that we built a formal process to answer it. The Drake Check is a one-week financial assessment for businesses with revenue between $1 million and $25 million, evaluating profitability, cash flow, leverage, and accounting processes. All we need is a quick intro call, a signed NDA, and access to your accounting software. We handle the rest. You leave with a clear picture of where things stand and concrete next steps you can take to improve financial performance.
THE 21 HATS PODCAST
The Real Payoff May Be in Owning, Not Selling: When Kate Morgan started thinking seriously about selling her business, she assumed the big payoff would come at closing. But as she tells David C. Barnett and Paul Downs this week, she’s come to understand that the smarter move might be not selling—at least not yet. Why? Because if the business keeps performing and she can gradually remove herself from the day-to-day operations, she may ultimately make more money by continuing to own it. That’s partly because, as David explains, small businesses often sell for lower multiples than owners expect. Which means the real value may not be in a clean exit, but in continuing to collect profits while slowly transitioning ownership to key employees. “So you’ll be selling the business,” says David, “and you’ll be collecting dividends or distributions on top of that. This is one of the most lucrative exits there can be.”
Of course, delaying a sale comes with its own risks. Markets change. Businesses cool off. Buyers get nervous. “You have to make the decision and make the sale happen while you’ve got a full head of steam,” David warns. Wait too long, and the numbers can start sliding in ways that dramatically reduce what buyers are willing to pay.
Plus: A Reddit post raises a brutal management challenge: What’s the best way to lay off a relative? “It really can’t affect your decision,” says Paul. “Because if it needs to be done, it needs to be done.” That doesn’t make it easier. It just means you may have to live w
You can subscribe to the 21 Hats Podcast—brought to you by Grasshopper Bank—wherever you get podcasts.
Thanks for reading, everyone. — Loren