Wealthy Barber and Dragons’ Den alumnus David Chilton makes Whisky Wisemen festival go that much smoother

In an entertaining speech, Chilton shared some of his favourite deals and the business lessons he learned on the hit show

It isn’t every day you get to chase a talk by a best-selling author with some of the world’s best whiskies. More than 200 people recently had that privilege when they gathered at the Imperial Vancouver for the latest instalment of the Be Wise Speaker Series & Whisky Festival.

The event is one of many organized by the Whisky Wisemen Society, a Vancouver-based non-profit that brings professionals together over a dram to raise money for charity. Whisky Wisemen CEO Lesley Anne Brown emceed the evening, whose media partners were BCBusiness and Vancouver magazine. Proceeds went to the Working Gear Clothing Society, which gives low-income and unemployed men the attire they need to join the workforce.

Natalie Cartwright, founder and COO of Vancouver-based fintech firm Finn AI, welcomed the crowd. Whisky host was Gez McAlpine, Canadian brand ambassador for Bruichladdich single-malt Islay whisky. 

After a three-part Bruichladdich tasting during the speaker portion of the night, guests enjoyed a whisky festival featuring brands such as Scotland’s Glenmorangie, Japan’s Nikka Whisky and U.S. bourbon maker Buffalo Trace Distillery. (Two recommendations: get your hands on some Nikka Coffey Malt and Glenmorangie Nectar d’Or.)

The keynote speaker was David Chilton, author of The Wealthy Barber: The Common Sense Guide to Successful Financial Planning, which has sold more than 2 million copies in Canada since he self-published it in 1989. Chilton also spent three years as a judge on the CBC Television show Dragons’ Den and has released a followup book.

I’ll take your money

A gifted storyteller, the unassuming Ontario native launched into a rapid-fire series of anecdotes about his life as an entrepreneur, celebrity and family man. When his son was in Grade 1, he asked Chilton to come to school and tell the class what he did for a living. First, though, Dad had to explain to his six-year-old boy what a financial expert is.

“I said, ‘Scott, you know when you’re sick, you go to the doctor, and the doctor makes you better? Well, when people’s money is sick, they bring it to me and I make it better,'” Chilton recalled. “I thought this was quite clever.

“So off we go to school the next day, and the teacher said, ‘Who is this?’ And Scott said, ‘This is my dad.’ And she said, ‘Oh, great, what does he do?’ And he said, ‘He takes sick people’s money.’ Which, frankly, I’m not above, to be honest.”

One really good idea

Chilton, 56, may have grown wealthy with help from his books, Dragons’ Den deals and public appearances, but as you’d expect, he doesn’t throw money around. For more than two decades, he’s lived in a 1,300-square-foot house in the countryside near Waterloo, Ontario. Long after he became successful, he drove a beater.

“I’ve always lived a humble life, and it’s got nothing to do with The Wealthy Barber and teaching thrift,” he said. “It’s because I don’t like stuff.”

Persuaded to join Dragons’ Den in 2012 after rebuffing the CBC, Chilton is glad he did. “I learned so much. I found the whole thing very humbling,” he said. “When you see 280 pitches a year, you’re reminded how much of a role luck plays in your success.” (Just a fraction of those pitches make it onto the show.)

“I was very lucky. I’m honestly not that sharp,” Chilton continued. “I had one really good idea, and that was it, and then it paved the way for my success. I had it at such a young age that all kinds of other opportunities ended up finding me because the brand got so strong.”

Kevin O’Leary, nice guy?

Thanks to Dragons’ Den—the show that the most Canadians have seen at least once—people often recognize Chilton and ask him questions. “The problem in Canada is it’s always the exact same question: Should I pay off my mortgage or max out my RRSPs? I’ve had that question 30,000 times. I hate that question.”

But Chilton doesn’t get it anymore. The replacement: “‘Is Kevin [O’Leary] really an asshole?’ I get that question every day. Yeah, he pretty much is, to be honest.”

Chilton added that generally speaking, he and fellow Dragons’ Den alumnus O’Leary get along. “In fact, I stay in fairly close touch with him. He’s a nice fellow.”

The same goes for the other Dragons, Chilton said. “One thing I would say CBC did exceptionally well is they chose people who would harness the brand power the show gave them to go back and get involved in charities. That was very high on their list, as it should be, and the people have really honoured that.”

Chilton explained that CBC also strives to maintain the integrity of Dragons’ Den pitches: for example, the show doesn’t reorder events or manufacture drama. “We don’t cheat the system at all in that show,” he said of the Dragons. “We don’t get any clues in our ears; we don’t get to see anything ahead of time. When [contestants] come down the stairs, we’ve never seen them before.”

It’s all about the execution

In the first five or six years of the show, which launched in 2006, there were very few successful deals, Chilton recalled. That isn’t surprising, given that the Dragons work with inexperienced entrepreneurs, he said.

“You’re investing in small companies that have a very, very low chance for a takeover,” Chilton observed. “So you have to make your money back slowly, through dividends, et cetera.” It’s a tough space: “If you look at the net net return of angel investing, it’s negative,” he said, referring to the value of a business after deducting liabilities from current assets.

Still, Chilton was particularly lucky, he said. “In the three years I was on the show, I did a lot of deals and closed a lot of deals, and they almost all seemed to work out fairly well, for whatever reason. And again, luck played a major, major role.”

One of Chilton’s best deals was with Steeped Tea, an Ontario-based company that does direct sales via Tupperware-style home tea parties. The founders were seeking $250,000 for 20 percent of the business; two years after Chilton and Jim Treliving invested, annual sales had surged to $20 million.

The company’s entry into the U.S. went well, but since then it’s faced some challenges, Chilton said, putting Netflix at the top of the list. “The reason Netflix has hurt that business is husbands and wives are very busy now. Kids are way more involved in extracurricular activities than they were when I grew up….So when they both are home one night, they want to stay in and watch Netflix together.”

What was Chilton’s biggest takeaway from Dragons’ Den? “The one thing I think the show has done poorly: it’s convinced too many people it’s about the idea. It’s not about the idea; it’s about the execution. It is all about the attention to detail, the pride in craftsmanship and all those types of things.” 

Be likable

Toward the end of the night, Chilton recounted how he joined forces with sisters Janet and Greta Podleski to publish their Looneyspoons cookbook in 1996. The book, which features inventive health-conscious recipes, set a Canadian publishing record, selling some 850,000 copies in the first 15 months, he said. The Podleskis have gone on to release three more cookbooks and branch out into everything from frozen food at Costco to kitchen gadgets at Canadian Tire.

“Of all the things they’ve done well—and they’re very talented—they are so nice, and they treat everybody with kindness and respect,” Chilton said of the sisters. “The more we learn about how you forge relationships and how sales works, for that matter, people deal with people they like and people they trust. Now we all know that, but take the next step: be likable and be trustworthy.”