David Chilton balancing a new business with writing a new book

By Ian Hunter

The pandemic has forced many people's lives to slow down, but in many ways, life sped up for best-selling author, David Chilton.

He’s accustomed to being on the road for nearly one-third of the year, but with most travel halted, he’s staying but staying grounded. Chilton spends his time split between his two home bases these days; Kitchener-Waterloo and Sarnia.

He was born in Sarnia but grew up in Waterloo and went to university at Wilfrid Laurier. In the pre-pandemic era, he might spend the week flying cross-country, but now he’s stationed at one of his two outposts.

“My whole life was travel,” Chilton said. “Even when I was running businesses, I was still running them a lot from hotels, airports, and airplanes because I’ve been on the road for almost 30 years as The Wealthy Barber.

“You’re out 100, 100-something days a year. If I’m not in a plane, I was off at the Royal York in Toronto and working out of that facility a lot. So, it’s been different being home non-stop, and I’ve really liked it.”

The Wealthy Barber author recently started a new business, Chilton & Associates, which helps small businesses and entrepreneurs implement exit strategies to sell their businesses. He came up with the concept about a year ago and officially launched this past spring.

One reason he’s so busy with this new venture is the demographics of his clients, which are predominantly baby boomers who started their own businesses in their 20s, 30s and 40s. They’re now looking to establish a succession plan, which is where Chilton & Associates assists with that transition.

As someone who started his first business at age 18, Chilton is no stranger to the world of small business and entrepreneurship. He enjoys the variety of this new venture and said this is likely the last business he will run.

“It’s one of the things I’ve enjoyed most in my career,” Chilton said. “I’ve been lucky to like most of what I’ve done, but this is right in my hotspot. I love the negotiating, the deal structure, I like dealing with the entrepreneurs, all of it.”

Kitchener-Waterloo has long been the home for The Wealthy Barber author, and when he’s not swimming in Lake Huron at his other home in Sarnia, he’s back on home turf in Waterloo. Many of Chilton’s best friends still live in Waterloo Region, which is why he often migrates back to KW.

“It’s a great community, it’s well diversified and there’s a high sense of community involvement,” Chilton said. “There’s not many economically similar areas to Kitchener where you’ve got all the success that and the broad base of industries that’s led us to all kinds of opportunities with the infrastructure and everything else. There are not too many places I’d rather live.”

When he’s not helping people selling their business, Chilton is hard at work on his forthcoming release, a third book as a follow-up to The Wealthy Barber and The Wealthy Barber Returns.

He’s aiming to have it ready sometime within the next year, and the new book will be outside of the realm of personal finance. Here's a sample of a chapter he released on Twitter earlier this year:

Chilton released his two previous books back in 1989 and 2011, but writing and marketing a book in today’s environment comes with unique challenges. With an endless stream of distractions, he said Twitter is his biggest weakness, and he sometimes gets sucked into the time pitfall when he’s doing research for the book.

With attention spans seemingly at an all-time low and with hundreds of distractions swirling around readers at any given moment, Chilton reveals the secret to keeping people engaged with a book.

“Anything you write has to be entertaining,” Chilton said. “You can’t just be a purveyor of information, even if the information is important, even if you’ve written it relatively well, it’s not going to work. How do you rise above the noise, capture people’s attention and then more importantly keep it once you’ve captured it?

“You have to do that through stories, you have to do that through keeping short, you have to do it through very compelling examples, and you probably in many instances have to do it through humour.”

Other than his best-selling books, most people know Chilton for his three-season stint on CBC’s Dragon’s Den show. He enjoyed all the people he met through the program — the entrepreneurs, the dragons, and the crew — but after making all those deals with new partners from the show, the time commitments became too much to handle.

In one case, he stood in as the quasi-CFO for the company since their business wasn’t large enough to have their own. Chilton loved the opportunity to be on the show, but admits it was overwhelming near the end.

Today, Chilton doesn’t miss the constant hustle of travelling on planes, trains and automobiles and living out of a suitcase. He relishes this unique opportunity to slow down, to appreciate his surroundings, and to do what he loves for a living.

“I’m a pretty lucky guy. I love what I do. Every day I’m excited about things. I say this to people and they think I’m kidding, but a lot of times I go to bed at night and I have trouble sleeping because I’m so excited about the next day, and I’m looking forward to all the things coming at me.”

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