Guinness's horse, Country House, was the 2019 Kentucky Derby winner with the improbable odds of 65-1. Country House claimed the win after Maximum Security was disqualified for interference, a shocking and historic finish. Guinness is also the founder and president of Blackwood Distilling Co., a luxury Kentucky whiskey brand rooted in one of the most improbable stories in recent Derby history. Blackwood is named after the horse stable that Guinness and his wife Lisa owned.

That next chapter is a case study in unconventional leadership. Guinness didn't start out in horse racing. He was living in Reno working construction until the housing market crashed, and a friend suggested he try the horse industry instead. He worked his way up from a groom to eventually owning a Derby-winning Thoroughbred. By his own admission, that win reshaped how people saw him overnight. Suddenly his opinion mattered in rooms it never had before. Rather than resting on that moment, he pointed that same outsider's drive at an entirely different industry.

The result is Blackwood Distilling Co., launched in 2020 in the middle of the COVID-19 pandemic. Blackwood breaks from convention here too: instead of batching and finishing barrels the traditional way, it re-barrels aged Kentucky straight bourbon and Indiana straight rye one-to-one into new toasted barrels, a proprietary process built on craft over volume. Guinness's path is a throughline of betting on himself in industries where he started as an outsider, and it's exactly that journey we dig into on this episode.