The StartWell Podcast

Most adult rec leagues run on the same model: charge as little as possible, pay as little as possible, and hope the gym is unlocked. Connor Renton looked at that model and decided the cheapness was the problem. Renton, 29, is the founder and CEO of Brodie, the Toronto-born adult basketball league now running across 20-plus markets in Canada and the U.S. It started in 2019. He'd just graduated, sig...

Matt Espinoza sold his first software company the same week he graduated university — then did it again, faster. Now, at 23, he runs Clover Labs (AI), a Toronto startup that grew to 65 employees in a year by building AI "growth agents" that mass-produce content, run outbound, and manage ad spend for other companies. In this episode of the StartWell Podcast, Matt breaks down the mechanics most grow...

Stan has helped over 100,000 creators and entrepreneurs earn more than $600M online — and takes $0 in commission on any of it. Vitalii Dodonov, co-founder and CTO of Stan, explains why the team made that call on purpose, and what it's built on top of it since. Vitalii traces his path from arriving in Grand Prairie, Alberta not speaking English, to self-teaching his way into a software career at eB...

Shopify's VP & Head of Engineering Farhan Thawar joins StartWell to unpack Sidekick, why Shopify builds its own tools instead of buying them, and how a 7,000-person hackathon and 1,000 annual interns keep the culture moving.

Venn co-founder Saud Aziz on building Canada's business banking alternative — from a cold email to employee #5, Revolut's Canadian expansion, and raising a $21.5M Series A from a team of 10.

Affirm CRO Wayne Pommen on building and selling PayBright, why credit cards are broken, and what Canada's fintech scene needs to grow up.

Former Anduril executive Eliot Pence left Washington DC to build the defense company Canada never had. Here's why he came back — and what's at stake.

Som Seif has spent two decades disrupting Canadian financial services — first with Claymore, one of Canada's earliest ETF companies, then as co-founder of Wealthsimple, and now as CEO of Purpose Unlimited, a platform spanning asset management, wealth management, SMB lending, and retirement solutions. In this conversation on the StartWell Podcast, he gets candid about the mindset holding Canadians...

Steven Wang, Rhodes Scholar, Harvard-trained lawyer, and CEO of Venture for Canada, joins Qasim Virjee at StartWell to talk about what it really takes to future-proof the next generation of Canadian workers, why the country has an experience gap (not a talent gap), and why buying a small business might be one of the most underrated entrepreneurial moves of our time.

Canada has no shortage of talent - but according to AJ Tibando, we have a mindset problem. As CEO of Shift Canada, AJ is leading a national effort to reshape how young people think about risk, failure, and entrepreneurship. Starting with students as early as grade five, Shift’s programs challenge one of the most deeply ingrained barriers in Canadian culture: the fear of getting it wrong. In this c...

Karim Gillani has had a front-row seat to some of the most important shifts in technology and finance over the past two decades. From early days in mobile payments to leading M&A at companies like Xoom and PayPal, and now as a co-founding General Partner at Luge Capital , his perspective on venture capital is shaped by real operational experience. In this conversation, Karim breaks down how th...

Naseem Saloojee, co-founder of Suma Capital, breaks down one of the most misunderstood opportunities in today’s market: SPACs - and why they may be making a comeback. In this conversation, we explore how founders, investors, and operators can navigate a market where traditional venture funding has slowed, IPO timelines have stretched, and liquidity has become harder to access. Naseem shares how hi...

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.co Ghassan Halazon, Founder and CEO of EMERGE Commerce, joins the StartWell Podcast for a candid conversation about what it really takes to build and operate e-commerce businesses at scale. From his early days leaving Wall Street to launch one of Canada’s biggest daily deals businesses, to building EME...

*Recorded at StartWell, Toronto's campus for corporate meetings & events: https://startwell.co/ Partnerships are no longer a side function - they’re becoming one of the most important growth channels in modern B2B. In this episode of the StartWell Podcast, Chris Lavoie - founder of Partnership Mastermind - breaks down why partnerships are having a resurgence, what most companies get wrong when...

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.co Ben Wise and Darren Chiu are the founders of Captivate - a newsletter and training platform that turns behavioral science into practical tools for persuasion, communication, and change. In this conversation, we dig into the line between ethical persuasion and manipulation, why emotion drives decisio...

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.co Joseph Fung is a 5x founder and CEO with a simple obsession - building places where great people can do their best work. In this conversation, Joseph walks through the real arc of entrepreneurship: bootstrapping companies to the brink, learning how exits actually happen, and why the hardest part isn...

*Recorded at StartWell - Toronto's campus for corporate meetings & events: https://startwell.co Max Tremaine is the cofounder and CEO of Sherpa - the travel infrastructure company helping millions of travellers every week understand what they need to cross borders, apply for eVisas as an add-on inside travel bookings, and validate documents for airlines and travel operators. In this conversati...

In this StartWell Podcast episode, lobbyist Morva Rohani breaks down public policy for founders, the reality of regulation in Canada, and why understanding government priorities can become a competitive advantage.

Goodlawyer CEO Brett Colvin explains why Big Law incentives are broken, how fractional general counsel works, and how scaling companies can modernize legal support with embedded in-house talent.

Collin Stewart has spent the last decade-plus helping founders find customers - but in this conversation, he’s not selling tactics. He’s selling sequence. We talk about Collin’s book, The Terrifying Art of Finding Customers , and why he wrote it in the first place: he didn’t want to regurgitate another “sales development playbook.” Instead, he wanted to name the part founders don’t want to face -...

What if “networking” is broken - and leadership is lonelier than we admit? In this episode, Christine Song (Founder, 529 Society) breaks down why big conference rooms and name tags don’t create real relationships - and why she believes leaders need a third space outside of work to talk honestly, pressure-test decisions, and build trust without politics. Christine shares how a single LinkedIn post...

Nayeema Raza believes that success comes from embracing authentic curiosity rather than chasing algorithms. For this episode of the StartWell Podcast, Nayeema joined us in studio in Toronto to discuss her lens on hosting her own show (Smart Girl, Dumb Questions), and what the modern media landscape looks like from her perspective as a journalist, filmmaker and podcaster.

In this episode , Qasim sits down with Katie Zeppieri, founder and CEO of The Mic Drop Agency , a PR and marketing firm working with venture-backed tech startups, reality TV talent and authors across North America. From her new base in Austin, Katie helps founders and executive teams tell their stories, earn trust, and grow faster. The conversation starts by untangling a common misconception: PR i...

This episode of the StartWell Podcast delves into the complexities of burnout, distinguishing it from acute stress and exploring the impact of chronic stress on mental health. Duncan So shares personal experiences and insights on recognizing the signs of burnout, the role of workplace culture, and the importance of community support in recovery. Innovative approaches to mental well-being and the i...

In this episode of the StartWell Podcast, Ruslan Nikolaev, co-founder of Float , shares the journey of building a fintech startup aimed at revolutionizing financial management for Canadian businesses.  We discuss challenges he faced in the financial landscape, the importance of data in making financial decisions, and the need for localized solutions in Canada.  The conversation also touches on the...