Ali St Cyr, 32

As a co-owner of Tomlin St Cyr Real Estate Services, Ali St Cyr works not just with one parent, but two. Her father, John Tomlin, and mother, Holly Tomlin, founded the Tampa-based company in 2016. But they came from different work backgrounds and leaned on St Cyr’s real estate expertise — she had previously worked for Coldwell Banker — as they got the new family business up and running. 

St Cyr says working with family members, particularly one’s parents, doesn’t have to be as tricky as it sounds. The key is to check emotional baggage at the door and think of yourselves as business partners first and foremost. 

“In a family, some things can be very dramatic, but it can't be that way in business,” she says. "Basically, I've had to build an entire new relationship with my parents, which is cool because I've learned a lot about how their mindset works in a way that I anticipated would be very different when we started this.” 

St Cyr says her parents’ willingness to experiment and take risks with the business surprised her, at first, but she was able to put herself in their shoes and understand their perspective. 

“I thought, ‘I'm the young buck — I'm going to want to take risks and try new things,’” she says. “And then my dad and my mom, they're like old corporate. … They're going to want to stay in their box, do things the way it's always been done. And it has been the total opposite. My parents scare the heck out of me sometimes when they want to try new things. And then I'm the one saying, ‘Well, nobody does it that way.’” 

Her parents, St Cyr came to realize, like to think outside the box because they’re closer to the end of their careers and want to quickly find out what works and what doesn’t, whereas she was prone to being overly cautious because she feared making a big mistake that would negatively affect her future. Understanding also came from her father’s insistence on writing out defined roles for him, Holly and Ali and coming up with a formal business plan. 

“We like to say that a family business is not for everyone,” St Cyr says. “The beginning can be rough, until you figure out your lane. We’re all chiefs, but we can’t all be chiefs all the time. So we have to decide who gets to make the decisions based off of certain scenarios and who has the best experience in the group to ultimately make the final decision.” 

Name: Ali St Cyr

Age: 32

City of residence: Tampa

Employer: Tomlin St Cyr Real Estate Services

Title: Broker/owner

Birthplace: Tampa

Years on the Gulf Coast: 32 — all my life!

Marital status/children: Married with one son

Alma mater/degree: University of Florida

What community group or organization are you most involved with? Big Brothers Big Sisters, Lions Eye Institute Board Chair, Junior League

What's your top tip for being productive? A disciplined work routine. Time blocking and prioritizing every day and making sure you "protect your calendar."

If you could have a side hustle, what would it be? Singing in a band

What's your favorite off-hours activity? Boating

What's your favorite board game, game show or video game? "Impractical Jokers"

What’s your go-to delivery service (DoorDash, Uber Eats, GrubHub, Bite Squad, etc.)? Uber Eats

What do you use most — Zoom, Skype, Microsoft Teams or Google Meetings? Google Meetings

What’s the best binge-worthy show you have enjoyed during the pandemic? "Tiger King" — I know I'm not alone here!

What’s the longest virtual meeting you’ve been on since mid-March? Two and a half hours

How many times had you used video for a work meeting prior to the pandemic? Three

What’s the most important lesson you’ve learned during the pandemic? I was able to cut out a lot of things that I used to think were important. It has allowed me to focus on my family and that happiness comes from what we create.

What do you miss most about the world pre-pandemic? I miss seeing Mikey, my little from Big Brothers Big Sisters, the most. I think about him every day and wish we could be together.

What have you been spending more time doing during the pandemic? Playing piano — I bought a keyboard in April.

Do you prefer working from home or working from an office? Office — I have a 1-year-old.

How have you kept up camaraderie with colleagues during the pandemic? I started having lunch dates in my conference room where we can spread out. I miss seeing everyone's smiles. We have also played some fun games during our monthly video meetings. We've gotten pretty creative.

What’s the first thing you’ll do after the pandemic? Travel