716: Ryan Spent 13 Years Without a Single Breakout Moment - Then Doubled His Whiskey Brand In 6 Months

Ryan Thompson ran a restaurant for 25 years, sold a couple of quick-serve spots, built a financial services company, and even ran a motel before he noticed the craft distillery movement taking off and decided someone in Vail, Colorado ought to start one - so it might as well be him. He went to Moonshine University in Kentucky, learned distilling from A to Z, wrote a business plan, and scraped together every dollar he could. Thirteen years later, 10th Mountain Whiskey & Spirit Company makes seven spirits, runs two tasting rooms, and donates to military nonprofits - named in honour of the historic 10th Mountain Division that helped start American skiing (and, as it happens, Nike).

In this episode, Ryan is candid about the unglamorous reality of scaling a spirits brand online: the genuinely bizarre regulatory maze of shipping alcohol across state lines, why his growth has never looked like a hockey stick, and the brick-by-brick philosophy that's quietly doubled his monthly sales.

What you'll learn in this interview:

Why a 120-seat restaurant and a fixed-bed motel have a hard ceiling on growth - and how that revenue cap is exactly what pulled Ryan toward the uncapped potential of e-commerce

How he started distilling on a tiny 13-gallon still (nicknamed Old Bessie) to keep early mistakes small and cheap, before scaling to a 500-gallon copper column still

Why he launched through two tasting rooms first - getting direct, over-the-bar customer feedback for a full year before selling a single bottle online

The regulatory maze most founders never see: being banned from direct-to-consumer sales entirely, the Washington D.C. licensed-liquor-store workaround, and why his online orders start in Colorado but ship from D.C.

Why he can only ship directly from his distillery to two states - California and Arizona - and how a fulfilment partner (Rackhouse) handles the rest

How he turned a tasting-room visitor behaviour (not wanting to check a bag with a bottle in it) into early organic online sales with no ad spend

The hire that changed everything: spotting 15 years of digital agency experience on a resume submitted for a tasting-room job, and redirecting that person to run marketing instead

Why his growth has always been slow and steady rather than explosive - and the "nice brick in the wall" mindset of stacking 2-4% conversion improvements instead of chasing a single game-changer

The real numbers: roughly $20-25K/month before joining Founder Operators i