The Wealthy Barber gives back to Lindsay’s Academy Theatre

It was only fitting that on the eve of his 65th birthday, Dave Chilton, better known to Canadians as The Wealthy Barber, took the stage at Lindsay’s Academy Theatre for one of his final speaking engagements before his planned retirement at the end of this year.

The evening was billed as “Finance and Life Lessons with Dave Chilton,” but for me, the real theme was generosity, kindness and community. Here’s why.

When I heard Dave was retiring after nearly four decades helping Canadians get smarter about their money, I sent him a text. I’ve known Dave for years, and I thought it would be wonderful to bring him to the Academy Theatre, where I served on the board of directors.

He called me back five minutes later with a question.

“Is your theatre a not-for-profit?”

When I said yes, he made an offer I couldn’t refuse. He would deliver his popular keynote, give every ticket holder two of his bestselling books, and waive his fee entirely.

Why? Because he loves theatre. That’s Dave Chilton. A guy who has enjoyed enormous success but hasn’t forgotten the importance of giving back.

The response from the community was equally generous. The show sold out, with every dollar raised going directly to support the Academy Theatre.

But a sold-out show doesn’t happen by itself.

Behind the scenes, the theatre’s small but mighty team worked tirelessly to make the evening special. From coordinating and managing countless details to welcoming guests and Dave, everyone went above and beyond.

And then there are the volunteers. The people who take your tickets, show you to your seats, serve your drinks and do countless other jobs that keep this historic theatre operating. Their generosity of time is something we should never take for granted.

Of course, an evening like this also needs businesses willing to invest in their community.

A huge thank you goes to Wards Lawyers, our presenting sponsor, whose enthusiastic support helped make the event possible. I invited Jessica Bolla from Wards onstage to explain why the firm continues to support so many local initiatives. Her answer captured the spirit of the evening.

“We’re a local firm. This is our home,” she explained. “Our business thrives because the community supports us. And it’s a responsibility, really, to give back, and we take it seriously.”

It’s a philosophy worth celebrating. When local businesses support local arts and culture, everyone benefits.

And then there was Dave. For more than an hour, he had the audience laughing while sharing the financial wisdom that has made him one of Canada’s most beloved money experts.

His number one lesson hasn’t changed since The Wealthy Barber was published nearly 40 years ago.

Pay yourself first.

Before you spend your paycheque, put a portion aside for your future. Make it automatic. Make it a habit. And keep doing it. Simple advice, but as Dave reminded us, simple doesn’t necessarily mean easy.

He also encouraged people approaching retirement to seek professional advice about how to draw income from their savings while managing taxes and the risk of running out of money.

He had some particularly pointed advice about estate planning. Have a will. Review it regularly. Make sure your executor is still the right person for the job. And don’t overlook powers of attorney.

For those of us in cottage country, Dave offered another warning: leaving the family cottage to multiple children can create more problems than parents ever imagined. His advice? Have those difficult conversations while you’re still around to participate.

What makes Dave such an engaging speaker is his ability to deliver serious advice without taking himself too seriously. He can have an audience laughing one minute and reconsidering their financial decisions the next.

There was one more surprise.

At the end of the evening, the theatre’s general manager Andrew Archibald rolled out a birthday cake, Dave blew out his candles, and the entire theatre sang Happy Birthday to a man who has spent much of his career helping Canadians build a better future.

It was a lovely way to thank him for helping secure the future of our theatre.

The Academy Theatre has been a cultural jewel of the Kawarthas since opening its doors in 1893. But preserving a 133-year-old building is no small feat. There’s always something that needs repairing, restoring or replacing, and it costs a lot of money just to keep the doors open. Protecting this legacy for future generations takes a community, which is why the generosity of people like Dave Chilton, our sponsors, volunteers and audiences matter.

Sign up for the Academy Theatre newsletter to discover what’s coming next. Buy a ticket, bring a friend, or consider volunteering.

Keeping this cultural jewel shining is something we can all play a part in.