Jim Canales, President, The Barr Foundation

06/13/23 • 34 min

Experience as a classroom teacher in California set Jim Canales on the path toward his role as president of The Barr Foundation, Canales shares in the latest episode of PNC C-Speak. One of the foundation’s focus areas is education. In 2022, the foundation awarded nearly $140 million to grant recipients.

“The foundation’s mission is to invest in potential,” says Canales, a Boston Business Journal Movement Maker, by awarding grants — in collaboration with businesses — for education and the areas of arts, creativity and climate. “These are challenges that require the engagement of a broad range of sectors to address them effectively. In philanthropy, even with our resources, we need partnership with the business community.”
Listen to the episode to hear more about Canales’ views on diversity among leaders in Boston; the best advice he’s been given — and gives — to others; and his favorite spot in the city. Powered by PNC Bank.Subscribe to C-Speak so you never miss an episode. Click here to listen on Apple Podcasts, Spotify and Stitcher.Download a transcript of the podcast.

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Mike Massaro, CEO, Flywire

Flywire CEO Mike Massaro does not take credit for building the once-struggling tech startup into a global, publicly traded company. The credit goes to the company’s “flymates,” aka employees, Massaro shares in the latest episode of PNC C-Speak.

Massaro, who once considered himself unprepared for the job and thought he’d be “the shortest-tenured CEO in the history of tech CEOs,” was the recipient of the 2019 Ernst & Young Entrepreneur of the Year Award in financial services.
During Flywire’s early days, Massaro says, the company’s culture was unearthed but not defined. Now it’s part of the organization’s core values. So are diversity, equity and inclusion. Massaro credits Flywire’s Chief People Officer Gary Cunningham with making him realize “if you can solve for equity and inclusion, you will inherently become more diverse.” These days, Massaro considers Flywire to be a “uniquely diverse company.”
Listen to the episode to hear more about how Massaro worked toward building a great culture at Flywire; the best advice he has been given; his outlook on Boston business; and what makes him laugh these days. Powered by PNC Bank.Subscribe to C-Speak so you never miss an episode. Click here to listen on Apple Podcasts, Spotify and Stitcher.Download a transcript of the podcast.

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Tom O’Brien, CEO, HYM Investment Group

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Tom O’Brien’s early-career stint as a campaign worker for presidential candidate and governor Michael Dukakis didn’t pay much – he remembers not being able to make car payments – but was nevertheless a rewarding, “transformative experience,” he said in this episode of PNC C-Speak. O’Brien, co-founder, managing partner and CEO of HYM Investment Group, believes others can benefit from work in the public sector.

“I would encourage people to think about politics and government, particularly at an early stage of their career,” O’Brien said.

Over the years, O’Brien has assembled a diverse team at HYM Investment Group consisting of people with varied life experiences and perspectives. “What we care mostly about is honesty” and kindness, he said. Whatever skills someone might need can be taught, “but we can’t teach you to be a good team member. You need to bring that to our organization.”

Listen to the episode to hear more about:

O’Brien’s wife of 30-plus years, Trisha, who’s taught him to be “present in the moment,” a better listener and more empathetic.
His concerns about affordable housing and the need to “fix the Boston public school system.
What gives him the most joy.

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Download a transcript of the podcast.