Dean Bradshaw co-founded the Cresco Wealth Management team in 1999, but his experience in the industry goes back even further. This month, we’re celebrating his 30th anniversary in the business! We love hearing Dean’s story from his early days—here’s what he had to say:
Thinking back to your early days, what did you want to be when you grew up?
Professional golfer. Absolutely.
How did you get started with golf?
It’s a funny story. I played competitive hockey growing up, and when I was 14, my team entered a tournament in Butte, Montana. We were expected to dominate, but we didn’t even make the playoffs. With time to kill, I kept pestering my mom for quarters for arcade games, and she finally told me to stop. Then, my friends and I noticed a golf course across the way. We wandered over and the pro offered us a chance to play for $5. He gave us one set of clubs to share and some old balls. I had a great time, and that’s how it started.
Where did your golf career go from there?
From 14 to 17, I got really into golf. Following high school, I was working multiple jobs —pumping gas and serving coffee at a Bingo Palace—but I saved up about $3,000 and decided to give golf a real shot. I moved to Victoria and played in a few Canadian tour events, but being a professional golfer wasn’t as glamorous as it seemed. I racked up credit card debt and struggled to pay rent. At one point, I had to admit to myself that this wasn’t working. That’s when I started looking for jobs.
How did you get through the tough times early in your career? There were definitely tough times. I applied to all sorts of jobs and couldn’t even get hired at Red Robin. I was embarrassed and ready to move back home when Midland Walwyn finally called me for an interview. I had seen a job posting for a wire operator, a role where you type in trade orders. I was a super-fast typist in high school with really high accuracy so it seemed like a good fit. I practically begged for the job, even offering to work for free for a month to prove myself. They hired me, and my first salary was $19,500. I thought I’d hit the jackpot!
What were the early days like? It was the perfect position for me. I’d start my day at 4:30 a.m., and by 5:15 or 5:30, I was at the office. I’d enter all the trades from the night before and get organized for the day. Back then, the markets closed at 1 p.m., so I was done by 1:30 and on the golf course by 2. In Victoria, that worked out well—I could still play 36 holes and get plenty of practice. I continued playing in amateur events and other competitions. But by the end of the second year, I knew I could make a difference for people and I knew this was what I wanted to do.
How did you transition from wire operator to Advisor? I was a hard worker—no ego, willing to sacrifice, and eager to learn. I was just 21 at the time, and I looked even younger, so I wondered how people would trust me with their money. I teamed up with veteran banker Ron Jacobson and together we started Cresco. It wasn’t easy—I had setbacks, including breaking my jaw early on and having my mouth wired shut for two months. But we pushed through.
What’s it like being on the Wellington-Altus Advisory Board?
I think we, as an industry, need to do better for our clients and for advisors. I’m very honest, and I don’t shy away from calling out things that need improvement. It’s challenging, but I believe we’re making a positive impact.
Reflecting on your team today, how do you feel about how far you’ve come?
I have nothing but pride for this team and the people on it. We are one of the leading wealth management practices in the country, at the top-rated investment dealer in the country.
What advice have you carried with you throughout your career?
I don’t have one particular mentor, but I’ve always been motivated when people tell me I can’t do something. That drives me. I’ve also learned that it’s about progress, not perfection.
