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Why Paddleboarding and Entrepreneurship are similar: Chris Milliken, CEO of Pengwine

It's water to wine for private chef turned sommelier, Chilean winery boss, author and even technopreneur.

There’s no stopping Chris Milliken from getting to the water’s edge. The 43-year-old made sure Lake Michigan was in the proverbial front yard of his summer house before paying for the lot. There’s also a smaller lake 150m away. All that, for the express purpose of being able to paddleboard, kayak or jet-ski on a whim.

To show he isn’t bluffing, the president of Chilean winery Pengwine and Singapore-based liquor wholesalers Amigos y Vinos spins his smartphone around. Two and a half golden kilometres of Lake Michigan’s shoreline glitter through the Skype video call. The prolific entrepreneur, his wife and two daughters leave their Tiong Bahru abode each summer for the holidays, so a video call is a prime opportunity to get a glimpse of his lifestyle.

On the screen, there’s no opposing bank in sight. “I enjoy seeing just how far I can go on my paddleboard. Being in nature is calming, and very humbling,” says Milliken. “It teaches you to recognise your limits. You never know when you’re going to get slammed to the bottom.”

That sense of adventure is a product of his sea-loving family’s expeditions. Milliken is into a dozen adrenaline-fuelled hobbies, including kickboxing and roller hockey, and they’ve landed him in perilous situations. Once, during snowboarding, a boot strap broke off.

“I went flying off the wrong side of the mountain, into a ravine. The bottom was sheet ice, and I broke right through that, into freezing cold water. I pulled myself out, but my legs were going numb.” Any regrets, I ask. “No, I went right back up the mountain. In my mind, I had to do it.”

That story checks out. After all, this is a man who went from kitchen hand to private chef, then winemaking in Chile after finding a business partner. To create more sales avenues, he pushed doggedly for new alcohol distribution regulations in the US, succeeding in 25 of the 52 states. That latter, trailblazing act saw an Amazon rep knock on Milliken’s door, asking how he managed it.

He’s also just written and published White or Red, It’s all in Your Head – a great introductory read for wine newbies – and made sure Pengwine was the first wine brand globally to roll out an app-based measure against counterfeiting. The technology scans the bar code of a bottle and keeps track of its movement around the world.

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So, does cresting choppy currents on a paddleboard have anything to do with Milliken’s entrepreneurial flair? Certainly, he says.

“In both cases, you know it’s entirely up to your own ability. You are absolutely going to fall down, whether it’s due to external factors like the waves or competition, or internal factors such as ‘misbalancing’ or mismanagement,” says Milliken in a sobering tone. “But you also know you’re going to climb back on, and get back up – you have to.”

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