by TechTO.org
Discover the untold stories behind the fundraise, founder journey, and more! Learn how Founders got their ideas off the ground, raised money, and even grew their respected organizations into billion-dollar companies. Join the TechTO and various guests as we lead candid conversations with founders, their partners, teams, and those who have supported them along the way.
Language
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Publishing Since
11/20/2020
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February 5, 2026
<p>From Global Exit to the EV Frontier with Ryan OstenHow do you scale a startup to 5,000+ dealerships and then navigate a massive acquisition? In this episode of the Founder Journey, recorded live at Toronto Tech Week (powered by StartWell), we sit down with Ryan Osten, Co-Founder & CEO of Lyteflo and former COO of Gubagoo.Ryan breaks down the grit required to dominate the automotive SaaS space and explains why he’s betting his next chapter on solving the "EV problem" for dealerships. Whether you are a founder looking for scaling tactics or an operator curious about the future of electric mobility, Ryan’s insights on "Carfax for batteries" and post-exit life are essential listening.In this episode, we discuss:- The Gubagoo journey: Scaling to global adoption and the Reynolds and Reynolds acquisition.- The "post-exit" reality: Lessons learned operating within a larger corporate structure.- The EV shift: Why battery health and incentive navigation are the new dealership goldmines.- Founder fundamentals: Sales, fundraising, and maintaining a long-term vision.Thank you to our podcast partners at <a href="www.startwell.co" target="_blank" rel="noopener noreferer">www.startwell.co</a> for their continued support.</p>
January 22, 2026
<p>In this special Toronto Tech Week edition of Founder Journey — powered by StartWell — Alex Norman and Alexandra Reilly of TechTO, sit down with Wayne Pommen, Chief Revenue Officer at Affirm (NASDAQ: AFRM) and former President & CEO of PayBright, to unpack the real story behind building and scaling Canada’s first Buy Now, Pay Later (BNPL) company.Wayne takes us inside PayBright’s evolution from a five-person startup to nearly $1B in annual transaction volume, sharing the unfiltered realities of hyper-growth in fintech. From raising debt to fund a lending business, navigating operational and regulatory complexity, and building teams under pressure, to ultimately selling PayBright to Affirm — this conversation goes far beyond the headlines.We also dive into Wayne’s transition from investor to operator, lessons learned from private equity, and why **team, product, and capital strategy** become existential decisions as companies scale.In this episode, we cover:* How PayBright scaled BNPL in Canada* Building and leading high-performing fintech teams* Managing risk, capital, and operations in lending businesses* Founder lessons from acquisition and hypergrowth* Why Affirm’s consumer-first credit model stands apart**Founder Journey brings you raw, behind-the-scenes conversations with builders who’ve actually been there — no pitches, no polish, just honest insights from founders and operators who’ve scaled.🎧 Built for founders, fintech operators, and startup leaders📍 Recorded during Toronto Tech Week | Powered by StartWell learn more at www.startwell.co</p>
January 8, 2026
<p>In today's episode, we are looking back at a popular conversation from Toronto Tech Week.Ron Spreeuwenberg, an experienced entrepreneur who built, scaled, and successfully exited a company, joined Alex Norman and Alexandra Reilly to share more about his journey from selling firecrackers on the schoolyard to co-founding HiMama, a vertical SaaS company for the childcare space. Ron discusses the deeply personal motivation behind becoming an entrepreneur, his methodical approach to validating his business idea and achieving product-market fit, and the challenges of scaling and maintaining culture in a growing organization. He also offers insights on the decision to exit the business, the importance of focus in a vertical market, and advice for founders.Thank you to our podcast partners at StartWell for helping us make this content possible. You can learn more about their offerings at <a href="www.startwell.co" target="_blank" rel="noopener noreferer">www.startwell.co</a>Subscribe to the Founder Journey series for more episodes like this dropping each month: https://open.spotify.com/show/5ztGmApbvduFqczYRD8IQm</p>
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Michael Hyatt
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Eva Wong
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Eldon Sprickerhoff
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Phillipe Lehoux
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Dan Park
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Simon De Baene
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Marie Chevrier Schwartz
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Emiel Bril
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Alberta Innovates CEO
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Discover the untold stories behind the fundraise, founder journey, and more!
Learn how Founders got their ideas off the ground, raised money, and even grew their respected organizations into billion-dollar companies. Join the TechTO and various guests as we lead candid conversations with founders, their partners, teams, and those who have supported them along the way.
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