Written by Andrew Seale

The buzz of building a successful startup can sometimes eclipse the isolation that can come with being at the top. For serial entrepreneur Ben Baldwin, that disconnection from his peers and his team, made it hard to talk about the challenges he faced as a leader.

“It’s very lonely not being able to share what you’re thinking about without worry or consequences,” he says. Baldwin lacked someone to listen and, more importantly, relate to the deeper, more personal challenges many leaders grapple with that get pushed to the side for fear of showing self doubt or waning confidence in certain choices.

What Baldwin needed was a support group. Thinking other founders might feel the same, he connected with a few other entrepreneurs, eight of them, all of them having raised big series A rounds, all of them struggling with the same lack of support for the unique challenges they experienced as leaders.

“We realized we didn’t have anybody to talk to about the toughest stuff,” says Baldwin. But it couldn’t just be a free for all meet-up; the key component was to create a defined protocol for committing to the group and communicating during its three hour sessions. “It’s a very specific, confidential group, a lot of us were trained by YPO (Young Presidents Organization) and we built ours around the model of their forum groups.”

The model worked, allowing founders to share best practices and expedite the pace at which they grew their businesses. It wasn’t long before word got around and more founders approached Baldwin. Worried it would upset the balance and intimate approach that a group of eight could sustain, Baldwin flew in a YPO trainer and started building other groups of founders using the same formula.

The end result was The Founder City Project, a peer-to-peer founders forum.

“Cassels Brock and Blackwell LLP gave me space for free which, without that support would’ve been impossible,” says Baldwin. He made the groups free for female founders to join to help boost diversity, with the city of Toronto providing support for women.

Ben Baldwin - The Founder City Project

It’s only been a year and a half but the concept has grown from the initial eight to 500 founders.

“Something really nuts is happening there’s a very large cohort creating these peer groups, finding friends, learning faster,” says Baldwin. “It’s exploded.”

He’s since expanded the program beyond training founders to launch their own groups to a peer-to-peer leadership training program called Founder City Talent.

The training and forum groups, not unlike the founder forums, focuses on helping entry-level employees develop more effective communication and leadership skills and connect better with managers, while helping managers better engage with employees and cultivate talent amongst their teams.

“It’s answering the question: what do leaders do that draw people in?” says Baldwin. And it’s a critical time to elevate Toronto’s talent pool through peer-to-peer support and interconnectivity.

“Our talent ecosystem has to double by 2020 just to survive, otherwise we’re not going to be able to deliver on our commitments of growth to the venture capitalists,” he says. Founder City Talent helps create a forum to let all levels of talent, from entry level to managers, tap into each others’ skill sets and gain valuable insight.

Baldwin says that the leadership training component has drawn interest much like the initial forums did. Local startups like Shopify, TWG and Tribal Scale participated in the first cohort.

“They signed up not knowing what they were getting into… they’re the heroes that backed this,” says Baldwin. “It’s amazing to watch the amount of support I get with this, people want Founder city to succeed and they’re doing it.”