How dating expert Damona Hoffman handles her relationship with money

We chatted with Damona about one of the most impactful relationships in your lifetime: the one you have with your finances. Here’s what she had to say.

Who are your money heroes?

The first money guru that I followed was Suze Orman. Her advice is always delivered with confidence and clarity. I spent many late nights binge-watching back-to-back episodes of her on television and taking notes. I had never thought of myself as interested in finance or investing until Suze made it accessible to me. We actually had planned to interview her for the FreshBooks I Make a Living podcast in Season 3 but couldn’t line up schedules. It was probably for the best, because I would’ve had finance fangirled all over the place.

How do you like to spend your free time? 

I work hard and I play hard. I love doing activities with my two kids, either educational activities (like museums) or adrenaline-filled activities (like riding rollercoasters). With my husband, we are foodies and love to find the hottest new restaurants to eat at. Coming from the entertainment industry, we also both love movies and live theatre. When I’m solo, you can find me sipping lattes at our local coffee shop, doing yoga, or at the spa. How L.A. is that!?

If money were no object, what would you be doing right now?

Honestly, I don’t let money stand in the way of what I want to do. I’m doing what I want to do right now, and I always find a way to make the finances support my interests. I probably would do more traveling, but as a mom and an entrepreneur with lots of clients to serve, there are a lot of other factors that prevent me from exploring the world as much as I would like to.

What was your first memory about money?

My first memory about money was probably getting money from the tooth fairy. As someone who always wanted to believe in supernatural things I wanted her to be real so badly, but I found it odd that the rates for teeth varied so dramatically from house to house.

What’s the first thing you remember buying with your own money?

I’m dating myself when I say this, but here goes: I accompanied my older sister to the record store when I was about 10 years old and I saw a cassette tape of Lisa Lisa & Cult Jam. I listened to music on the radio and I had several records of kids’ music, but I had never bought my own music before, let alone anything cool and Top 40. I only knew one of their singles and wondered if I would like the rest of the album, too. My sister reasoned that if I liked one of their songs, I would probably like the others, so I bought it.

What was your first job?

My very first job was actually doing billing for my mom’s business when I was about 13 years old. My mom hated math (still does) and was desperate to outsource the work to someone else, and I was desperate to earn more money to buy more cassettes and see more movies at the mall.

What was the biggest money lesson you learned as an adult? 

My biggest money lesson was learned while buying my first home. It happened by accident. My boyfriend (now husband) and I had been dating for a few years, and we started to go to open houses for fun. One Sunday, we unexpectedly stumbled upon my dream house, and it was in our price range and had been sitting on the market for a while. I called my friend who was a realtor and she walked me through the process, assuring me that we’d have the 30-day escrow period to change our minds. In the end, I got the keys to the house and an engagement ring on the same day. It is where we started our family, where I first ran my business, and where we formed many memories. During the economic downturn in 2008-2009, our house lost nearly half its value and I worried that I’d made a terrible mistake but in the end we held onto it and were able to sell it a few years later for a little more than we paid with multiple offers to choose from. 

I learned the power of real estate investment. Owning property has turned out to be the best financial decision that we ever made. Of course, the devil is in the details, so I was lucky to have a realtor and financial advisor that I trusted along the way to make sure we were getting the right mortgage and weren’t buying more house than we could afford. I think Suze Orman would have approved!

What’s the best money advice you’ve ever received?

I worked for a real estate developer in college who would tell me “work smart, not hard.” We’ve been conditioned to think that working harder will generate more income, but I’ve learned that it’s more about being strategic and smart about managing your money.

What’s the worst money advice you’ve ever received?

My parents told me not to buy a house with someone I wasn’t married to (remember I got engaged the night we got the keys), but actually, co-owning a home was our first major partnership together and a bigger sign of commitment than any engagement ring.

Would you rather receive a large sum of money all at once or a smaller amount of money every week/month for life? 

That’s easy, a large sum all at once (assuming I don’t have to pay taxes on it upfront haha). I would invest the majority of it so it could grow into a bigger pot through compound interest.

What do you think is the most underrated financial advice, tip or strategy?

I actually have two for entrepreneurs: 

1. Bill right away. I had a terrible habit of procrastinating on billing until I found FreshBooks. They made billing so easy I couldn’t procrastinate anymore. When you are slow to bill, you risk having to chase payments or forgetting about them entirely. Plus, you are essentially giving the company or person who owes you a free loan.

2. Balance your books regularly. I also was terrible at this without FreshBooks, but being more organized about what’s coming in and going out has helped me get clarity on the things I’m spending on, if I need to pull back, and when I am beating projections and have more to invest in the business than expected!

What is the biggest misconception people have about growing money?

That you have to work for it. You can build wealth through investments that are still your money. Even if you didn’t put in 40 hours a week on it.

Can you share a money regret?

I didn’t buy Peloton stock when I bought my bike (prior to the pandemic). By the time I figured out the trend the share price was already rising. I could’ve made a lot more money if I had trusted my gut on that one.

What is something you don’t mind spending money on that someone else might not?

I love to spend money on experiences instead of on stuff. Since you can’t take any of it with you, I like to use money to enhance my time while I’m here. For me, a pair of Manolos isn’t going to do that as much as a flight to Hawaii—I know others might disagree. Values are hugely important and actually something I try to have my dating coaching clients get clear on before moving into a relationship. Having shared values, especially around how you spend your money, is a big predictor of long-term compatibility.

What’s the first major purchase you made as an adult?

My first car that wasn’t gifted to me. I opened a credit union account at work—I was a junior executive at Paramount Studios at the time—because I heard you could get great interest rates and pre-approvals on auto loans from them. I had a little money taken out of my check each week to go into my car fund. Then I test-drove every car I could find until I landed on the Toyota Matrix. I’ve owned several other cars since, but I still have this car and it’s going strong over 100,000 miles later.

What’s your take on debt?

Well, there’s good debt and bad debt. It all comes down to how the debt you incur can lead to the betterment of your life, what your plan is to pay it down, and what interest rate you’re paying. I survived my first few years as a low-paid assistant in Hollywood living off of credit cards, and my grandmother never understood why. Growing up in the depression, she said I shouldn’t spend more than I had. But I looked at that period as an investment in my future and I knew that as soon as I broke into the next level of my career I would be able to pay it off. It took many years but it was worth it.

What was your most recent splurge?

I flew to New York for Lavern Cox’s 50th birthday party. Airline tickets were insane but I knew it would be an unforgettable experience that wouldn’t come around again so it seemed worth the investment. And trust me, it was.

What is the last money-related book you read?

The Mindful Millionaire: Overcome Scarcity, Experience True Prosperity, and Create the Life You Really Want by my friend Leisa Peterson. There aren’t nearly enough books about money from women. Leisa’s approach is so unique and her writing is so captivating. She reframes long-held beliefs about money that were overdue for a re-write.

What is something you always have in your wallet?

My Capital One Visa. My husband thinks I’m a maniac about accruing points, but he also loves all the free airline tickets and upgrades the card earns us.

What is your favourite possession? 

My yoga mat. Wherever I lay it down is home. 

What’s your next money goal?

I would love to take an international trip with my family next summer and with four tickets to buy now, points alone won’t cut it. As a small business owner, I always make sure my team is paid first, and I invest in the business second, so I don’t traditionally take a large salary for myself. I’m planning to increase revenue in the next two years, so I can benefit from the momentum I’ve built.

Read more My MoneySense profiles:

• From being wired to spend to the emotional attachment to money, Shaun Maslyk unpacks how psychology can affect finances
• Ambitious Adulting’s Liz Enriquez on growing up low-income, the worst financial advice she’s received and more
• What a mutual fund flop, part-time jobs and a box of Nerds taught Sandy Yong about managing her money
• “I took a break from Bay Street to co-write a musical”: Myron Genyk on his money values and getting financially cut off at 20

About MoneySense Editors

MoneySense editors and journalists work closely with leading personal finance experts in Canada. Since 1999, our award-winning magazine has helped Canadians navigate money matters.

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