From the pressures of professional sports to the grind of entrepreneurship to the fast-paced world of live television, three high-profile leaders revealed how they made a career out of doing what they love, sharing their experiences at last night’s networking and professional development event hosted by The Ottawa Business Club.

The crowd of roughly 100 attendees listened to a series of fireside chats featuring Will Aiello, co-host of CTV Your Morning Ottawa; Jennifer Stewart, founder and CEO of Syntax Strategic and co-founder of The Honest Talk and The Women’s Summit; and Adrian Sciarra, president of the Ottawa Redblacks and Ottawa 67’s.

The event took place at Venue Twenty Two. For some, it was their first time in the scenic space, located high above our city’s downtown on the 22nd floor of The Westin Ottawa hotel.

After 90 minutes of socializing, everyone was welcomed by Conrad Dickinson, founder and president of The Ottawa Business Club (OBC). He was joined by his team: Billy Donovan, Michael Kouts, Erin Ritchie, Talia Zaidi, Jon Hindo and Ian Alexander, who participated in a series of fireside chats with the special guests.

The Ottawa Business Club’s volunteer team consists of, from left, Jon Hindo, Talia Zaidi, Conrad Dickinson (founder and president), Ian Alexander, Michael Kouts, Erin Ritchie and Billy Donovan. Photo by Caroline Phillips

For Aiello, returning to his hometown last year added a whole new layer of meaning to his day-to-day. “Everything I do has a bit more heart and passion because it’s the city I grew up in,” said Aiello, whose decade-long career in broadcasting has included stints in Sudbury and Kitchener.

He shared that his morning ritual starts with an immersive cold plunge at 3:30 a.m. An hour later, he and his colleagues are working hard on the morning show. “It’s go-go-go,” said Aiello. (It was impresive he was even at the OBC event, considering how early he rises and shines).

He talked about the evolving media landscape and, in an era of growing “fake news,” expressed pride in working for a company committed to both local reporting and authentic storytelling. He also talked about how people’s habits around news have changed. “Everything used to be all about the newscast and now it’s ‘Let’s get it online first’,” said Aiello.

His advice to early-career professionals was to find the confidence to be themselves. “It’s easier said than done, but be your true, authentic self,” said Aiello, recalling how he struggled to figure out his own direction in high school while juggling roles as both lacrosse team captain and the lead in the musical Grease.

Aiello said he explored several areas before finding his way into broadcasting. “I just focused on what mattered to me and what would make me happy. I went down that road and have never looked back.”

Will Aiello, centre, co-host of CTV Your Morning Ottawa, in a fireside chat with Michael Kouts, far left, and Billy Donovan, both from The Ottawa Business Club. Photo by Caroline Phillips

The room heard how Stewart was only 25 when she started her own business. Syntax Strategic has grown into an Ottawa-based national full-service strategic communications, marketing and public affairs firm. It just opened an office in Vancouver and is looking to expand into the Maritimes.

While described as a “success story,” she modestly admitted that she never thinks of herself that way. “You just keep grinding and you keep working and you keep striving for what’s next,” said Stewart, a married mother of two. “When I think of what success looks like, I’m thinking about what impact looks like, how I can best serve my team and what kind of clients we want to work with.”

Her life goal, she said, is to live fully and with purpose. “I know it sounds a bit morbid, but when I’m on my deathbed, I want to be able to say I really lived while I was on this earth.”

When asked what’s next for her company, she had the room laughing with her tongue-in-cheek answer: “Global domination.”

Stewart shared that, until a few years ago, her days started at 5 a.m., giving her evenings free to be with her children. She acknowledged that she’s worked exceptionally hard over the years and is the kind of leader who isn’t afraid to embrace opportunity and responsibility.

As if running a company weren’t enough, she also co-created The Honest Talk podcast and media platform with her friend, communications expert and professional emcee Catherine Clark, to hold more candid conversations about what the workplace looks like for women.

It started as an idea, discussed over a glass of wine, and was turned into something that now has national reach. The pair also host The Women’s Summit. It’s returning to the Brookstreet Hotel this November and is already sold out.

Jennifer Stewart, founder and CEO of Syntax Strategic and co-founder of The Honest Talk, participated in a fireside chat as part of The Ottawa Business Club’s latest networking and professional development event, held at The Westin Ottawa on Tuesday, Feb. 17, 2026. Photo by Caroline Phillips

Sciarra talked about what it’s like to lead both the Ottawa 67’s and Ottawa Redblacks, sharing insight on what it takes to successfully run professional sports organizations and how to manage the unique pressures that come with the territory.

“I always say 95 percent of my day is probably the same as anyone else who’s running a business,” said Sciarra. “The five percent that’s different is that we’re in a business that’s a passion point. It’s very emotional. When we do well, we get to jump up and down and do high fives; when we do poorly, we get yelled at from the local community rink.”

He acknowledged that work-life balance doesn’t really exist in his world. “If you love what you do, you don’t think of it as work,” he said of the early mornings and late nights. Even on Monday’s Family Day, Sciarra caught a 67’s game with his wife, who embraces the sporty lifestyle. They did manage to go out for dinner afterward. “My kids are at games all the time,” he added. “They grew up around the field and on the ice.”

When the Redblacks celebrated their 2016 Grey Cup win in Toronto, where the championship game was held, Sciarra’s then-nine-year-old son came away with a minor injury. He was playing football with the sons of former quarterback Henry Burris when a tackle left him with a cut that needed a couple of stitches to his ear. He now has a scar that tells a story from that special day in sports history. “That’s kind of cool,” said Sciarra.

Sciarra described the latest plans to revitalize and modernize Lansdowne as “transformational” for the sports teams that use the aging facilities. “It’s a struggle to put on world-class events. We have all sorts of issues. It’s not a good thing when you’re talking about an arena, and when it rains outside, it rains inside. That’s not what we want.”

Adrian Sciarra, president of the Ottawa Redblacks and Ottawa 67’s, in a fireside chat with Jon Hindo, far left, and Erin Ritchie, both from The Ottawa Business Club. Photo by Caroline Phillips

Guest speaker Jennifer Stewart (centre), founder and CEO of Syntax Strategic, was joined by a couple of members of her team, Sophia Wojdak, left, and Mackenzie Houston at The Ottawa Business Club networking and professional development event held at Venue Twenty Two at The Westin Ottawa on Tuesday, Feb. 17, 2026

From left, guest speaker Will Aiello shares a laugh with Reza Mashkoori, manager of corporate sponsorships at Christie Lake Kids and president of Crossfit NCR, and Billy Donovan, a volunteer organizer with The Ottawa Business Club, during the networking portion of the event. Photo by Caroline Phillips

Conrad Dickinson, president and founder of The Ottawa Business Club, welcomed roughly 100 attendees to Venue Twenty Two at The Westin Ottawa hotel prior to the fireside chat with Ottawa’s Will Aiello, Jennifer Stewart and Adrian Sciarra. Photo by Caroline Phillips

Attendees mingled during the cocktail reception portion of The Ottawa Business Club’s latest gathering, held at Venue Twenty Two at The Westin hotel. Photo by Caroline Phillips

From left, Deborah Lehmann (The Ottawa Cancer Foundation), Jesika Arseneau (Forge & Haven), Yasser Ghazi (RBC), Tammie Trellert (business development professional), Michelle Crogie (PLEO — Family Peer Support) and Reza Mashkoori (Christie Lake Kids, CrossFit NCR) at The Ottawa Business Club’s latest networking and professional development event, held at Venue Twenty Two at The Westin Ottawa. Photo by Caroline Phillips

Attendees, including The Ottawa Business Club’s founder and president, Conrad Dickinson, mingled during the cocktail reception portion of The Ottawa Business Club’s latest gathering, held at Venue Twenty Two at The Westin hotel. Photo by Caroline Phillips

From left, Talia Zaidi and Erin Ritchie are part of the volunteer team that organizes The Ottawa Business Club’s networking and professional development events. Photo by Caroline Phillips

Organizers and attendees of The Ottawa Business Club’s networking and professional development event at Venue Twenty Two, The Westin Ottawa, listen from the audience. Photo by Caroline Phillips

From left, Michael Kouts and Billy Donovan are part of the volunteer team that organizes The Ottawa Business Club’s networking and professional development events. Photo by Caroline Phillips

From left, Josh Raganold (Welch LLP), James Baker (Keynote Search) and Reza Mashkoori (Christie Lake Kids, Crossfit NCR) at The Ottawa Business Club networking and professional development event held at Venue Twenty Two at The Westin Ottawa on Tuesday, Feb. 17, 2026. Photo by Caroline Phillips

Attendees mingled during the cocktail reception portion of The Ottawa Business Club’s latest gathering, held at Venue Twenty Two at The Westin Ottawa. Photo by Caroline Phillips

From left, co-organizer Ian Alexander, event sponsor Muthana Mohamed (Whitestone Law) and co-organizer Jon Hindo at The Ottawa Business Club networking and professional development event held at Venue Twenty Two at The Westin Ottawa on Tuesday, Feb. 17, 2026. Photo by Caroline Phillips

Shravana Ramgoolam and Ahmet Kapici from the Carlington Community Health Centre, which was a charity partner of The Ottawa Business Club’s networking and professional development event held at Venue Twenty Two at The Westin hotel on Tuesday, Feb. 17, 2026. Photo by Caroline Phillips

From left, Natalie Benson, director of fundraising and communications at Christie Lake Kids, in conversation with public servant Kawal Pirwani and Emily Chen (OXARO) at The Ottawa Business Club networking and professional development event held at Venue Twenty Two at The Westin Ottawa on Tuesday, Feb. 17, 2026. Photo by Caroline Phillips

Realtor Fady Khudair and Sylvie Beaudry (Ottawa Birth and Wellness Centre) at The Ottawa Business Club networking and professional development event held at Venue Twenty Two at The Westin hotel on Tuesday, Feb. 17, 2026. Photo by Caroline Phillips

From left, The Ottawa Business Club’s Jon Hindo, Lauren Parkes (CAA North & East Ontario), James Baker (Keynote Search) and Conrad Dickinson, president and founder of The Ottawa Business Club, at their networking and professional development event held at The Westin Ottawa on Tuesday, Feb. 17, 2026. Photo by Caroline Phillips

Attendees mingled during the cocktail reception portion of The Ottawa Business Club’s latest gathering, held at Venue Twenty Two at The Westin hotel. Photo by Caroline Phillips

From left, Ryan Kaitola (Bell Media), Reza Mashkoori (Christie Lake Kids, CrossFit NCR), CTV Your Morning Ottawa co-host Will Aiello and Billy Donovan, co-organizers of The Ottawa Business Club’s networking and professional development event held at The Westin Ottawa. Photo by Caroline Phillips

Drew Yenson and his fiancée Sara Werblinski were helping out at The Ottawa Business Club’s latest gathering, held at Venue Twenty Two at The Westin hotel. Photo by Caroline Phillips

From left, Dr. Mario Bassi, Ben Lidzbarski (RBC Dominion Securities) and Rob Murphy (CIBC Wood Gundy) at The Ottawa Business Club’s latest gathering, held at Venue Twenty Two at The Westin Ottawa. Photo by Caroline Phillips

From left, The Ottawa Business Club’s founder and president, Conrad Dickinson, with the event’s guest speakers: Will Aiello, Adrian Sciarra and Jennifer Stewart — three leaders in their respective fields. Photo by Caroline Phillips

This article is made possible through sponsorship from Star Motors, WCPD, Syntax Strategic, Marilyn Wilson Dream Properties, ExecHealth, Infinity Convention Centre, Altis Recruitment, Bell Canada, First Avenue Investment Counsel, RBC, Welch LLP, Brazeau Seller Law.

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