David Chilton is in Detroit settling in for what will be a long interview.
It’s 1991, the United States is in the middle of the savings and loans crisis, Detroit is experiencing mass population decline and economic turmoil, and Chilton is riding a high after publishing one of Canada’s bestselling books on personal finance, “The Wealthy Barber.”
Chilton is ready for the moment.
“Let’s talk hair care,” is how she opens the interview.
If you’re one of the few Canadians who haven’t read the Canadian bestseller that sold more than two million copies, Chilton is not a barber, and his book is not about the latest trends in hair fashion.
The radio host — as it turned out — had not read his personal finance book. In fact, it was clear she didn’t even know what the interview was supposed to be about.
“Yeah, that was a bit of an embarrassing, humbling moment,” said Chilton, now 64, with a long sigh and a chuckle from his home in Waterloo Region.
More than three decades later, Chilton is back on a media tour for his latest update to the 1989 classic, bringing an old steady voice to the chaos of 2025’s meme-fuelled, crypto bro finance world.
To clarify for the kids: no, he’s not here to cut your hair, but he is here to help you plan for your retirement.
“I’ve got to be the only author in history who became known as the character in their book,” he said. “When you think of Herman Melville, nobody calls him Moby Dick, right? But wherever I go, people say, ‘that’s the wealthy barber.’ So, that’s what I’m known as. I’m not David Chilton, I’m the wealthy barber.”
David Chilton at his Wellesley Township home.
Mathew McCarthy/Waterloo Region Record
The anecdote has more layers the more you speak to Chilton.
Not only has he never actually cut anyone’s hair, but he hasn’t even changed his own hair cut since he was six years old — “I grew it out a little bit in high school, but other than that, it’s pretty boring up here.”
It was an unlikely pathway for Chilton’s literary fame, from a guest columnist in Waterloo’s “Exchange Business Magazine” to celebrated author.
The original idea for his first book didn’t even take place in a barbershop. It was about a wealthy bartender, an idea he dreamt up after watching an episode of “Cheers.” But when it got time to start writing and alcohol got involved, the story got too messy. He changed the focus to a barbershop, and the rest is history.
Now, unlike Chilton’s haircut, it’s time for a makeover.
After 36 years, Chilton is taking readers back to the barbershop with the release of a fully-updated version of the Canadian smash-hit, bringing his sound financial advice to a new generation of Canadians.
A lot has changed in the world of investing, but the self-described finance nerd has never stopped learning and tinkering with his strategy to help everyday Canadians reach financial freedom.
“There’s enough change out there in terms of products, costs, the economy, that a fully updated version was very much needed. And again, people say, ‘why did you write it now?’ Well, it really comes down to two reasons. First, it’s challenging times out there. And second, I’m old. I knew if I didn’t write it soon, I was going to be dead. The clock’s ticking here.”
David Chilton, author of “The Wealthy Barber,” sits in the White Star Barber Shop in Waterloo, Friday, April 1, 2005.
Mathew McCarthy/Waterloo Region Record file photo
This marks the third update in the franchise after “The Wealthy Barber Returns” in 2011.
Chilton tried to do something different in that book, with a new narrative flow featuring short chapters in his own voice.
This latest instalment returns to the original format following a set of fictitious characters — some old and some new.
“Roy and his buddies are more or less there in an old form, but there are new characters that come into the shop, different names, different backgrounds, a little bit different personalities,” he said.
“Why did I do that? I wanted a few more scenarios to cover off. There are enough different circumstances now that I felt that if I could have one more character, that gave me some different ways I could play and different people doing different things. Subtle nuances matter, so you’re trying to give yourself as much opportunity as you possibly can, and it seems to have gone over well.”
In general, a lot of the teachings have stayed similar, he said. What’s changed is how you apply them.
Chilton still preaches paying yourself first and investing between 10 and 15 per cent of your income for long-term growth. In an ideal world that’s based on your gross income, he said, but for others it might mean net income.
It’s easier said than done, he said, and part of the book factors in these realities and discusses options that are realistic.
When he wrote the original, he largely focused on options like the registered retirement savings plan (RRSP).
But now there is also the registered pension plan (RPP), tax free saving account (TFSA) and first home savings account (FHSA), and you have to understand them to understand what you should prioritize.
“Well, by the way, the FHSA, if you’re eligible, you always prioritize,” he said.
“You’re walking people through not only how they work, but their pros, their cons, their subtle nuances, so they can decide which route to take. That’s the challenge with the rewrite and keeping it all flowing and not overwhelming and not getting so far into the weeds that you lose the reader.”
It may seem like a tall order for someone whose big hit came in 1989, but the gaps in between books haven’t meant gaps in between his learning, and that includes a three-year stint as one of the angel investing dragons on CBC’s Dragons’ Den.
“I may be the biggest financial geek you’ll ever come across. To this day, I still read 30-40 books a year and I still follow everything very closely. My social life is embarrassingly bad, and so I tend to spend a lot of time watching YouTube videos about all the different spaces. And so, I had the knowledge, and it was really about getting it onto the page.”
Dave Chilton and the cast of Dragons’ Den.
THE CANADIAN PRESS
There’s no shortage of get rich quick schemes out there.
The growth of social media sites like TikTok and Instagram have seen many so-called financial experts go for engagement and quick hits, but they can often miss the subtle nuances about personal finance.
And every time young investors throw away their money on the latest trendy stock, Chilton just shakes his head.
“I’ve been upfront that when I was a young guy, lots of people took a small part of their RRSP and played penny stocks in the Vancouver Stock Exchange, he said. “What people didn’t do was take 100 per cent of their portfolio and do these types of meme stocks or strange crypto coins, it’s very frustrating.”
That doesn’t mean he is against crypto. But just like any other investment, he preaches caution, research and a balanced portfolio.
He has a similar answer when it comes to buying a house.
“I’m very mixed on it. I think when you do an accurate accounting of the cost of home ownership, you can make a fairly compelling case for renting,” he said. “I didn’t pull any punches or try to make things look better than they are. The home ownership chapter took longer to write by far than any chapter in the book. It was tested over and over again, and I think settled in at a very nice spot.”
The thing about personal finance is that there isn’t a one-size-fits-all approach, he said. And while there are many sound, responsible investors with followings online, there is also a lot of slop designed to bring in clicks and eyeballs.
It’s an intimidating world to delve back into.
“I’ll be honest that I was very worried about competing with the new era and all the videos,” he said. “We all struggle with attention, and I’m the first to admit I struggle with it. I think the hope is that there is comfort in going to a single source from someone who has been around.”
He isn’t chasing two million book sales this time — though that wasn’t the goal the first time around, either. He would have been happy with 25,000 copies sold, and it was looking like it would play out that way until the spring of 1990 when corporate sales started coming and it just snowballed.
It wasn’t a fluke, and there was a lot of sweat equity involved, but he won’t be spearheading another monster marketing push for this update, and that mostly comes from enjoying his current stage of life. He lives in a small rural home that’s about 1,300 square feet and has a new puppy that he calls a “terrible financial investment” that he is happy to lose on.
With this new book, he’s just looking for impact.
“If I’m out at the Daily Grill one day and someone comes up and tells me, ‘hey, I wasn’t taking advantage of my group RRSP at work, but you harassed me so much in that book about how stupid that was, so I signed up now.’ I mean, that’s fantastic, and that’s really what I’m hoping for.”