Founder Journey | The Untold Stories of the Founder Journey

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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.

  1. FEB 5

    Founder Journey ft. Ryan Osten

    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 www.startwell.co for their continued support.

    41 min

  2. JAN 22

    Founder Journey ft. Wayne Pommen

    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

    40 min

  3. JAN 8

    Founder Journey ft. Ron Spreeuwenberg

    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 www.startwell.coSubscribe to the Founder Journey series for more episodes like this dropping each month: https://open.spotify.com/show/5ztGmApbvduFqczYRD8IQm

    48 min

  4. JAN 1

    Founder Journey ft. Mark Jaine

    In today's episode, we are going back to Toronto Tech Week, where we hear the story of an entrepreneur who started as a 21-year-old intern at a struggling, debt-ridden Toronto tech company called Intelex in 1999. Mark Jaine, details how he transitioned from selling the company's DOS-based environmental and safety management software—by shipping CDs and walking customers through installation over the phone—to taking on greater responsibility due to a "vacuum" of leadership.Over two decades of "compounding improvement", he led Intelex to cash flow break-even by 2001-2002, achieved 45% year-over-year growth for 14 years, paid off $8 million in debt, and grew the company to 500 employees and roughly $100 million in revenue. Discover the unconventional strategies that drove this growth, including raising product prices from $500 to $50,000, using "brute force sales", and successfully executing a customer-funded development model. Subscribe to the Founder Journey Series for more episodes like this: https://open.spotify.com/show/5ztGmApbvduFqczYRD8IQmThank you to our podcast partners at StartWell. Learn more about how they can support your content initiatives at www.startwell.co

    43 min

  5. 12/17/2025

    Founder Journey ft. Sally Daub

    In today's episode, we're looking back on one of our favourite Toronto Tech Week conversations featuring BorderPass Co-Founder, Sally Daub. Sally, an entrepreneur who has built, successfully scaled, and exited a company and is currently doing work with Border Pass.  She discusses her history of entrepreneurship, including making money by renting buses and photocopying engineering books in college, her career as an Intellectual Property lawyer, and her experience as a founder, including her time at Nortel and ATI.  Sally also shares insights on identifying talent and fostering it, the importance of understanding the law in business, and the challenges of raising capital in the current market, especially in Canada.  ⁠Subscribe to the Founder Journey series⁠ for episodes like this. Thank you to our podcast partners at StartWell for helping us bring this series to life. You can learn more at ⁠www.startwell.co⁠

    54 min

  6. 12/11/2025

    Founder Journey ft. Scott Stevenson

    In today's episode of Founder Journey, host's Alex Norman and Alexandra Reilly are joined by Scott Stevenson, Co-Founder and CEO of Spellbook, the legal AI startup that has captured the attention of investors and builders across North America.Scott opens up about his early entrepreneurial spark, the twists and turns that shaped his founder journey, and the pivotal moments that led to building Spellbook into one of the most-watched companies in the legal tech space. He shares an inside look at their recent fundraise, how the team navigated rapid growth, and what it actually takes to build an AI company that solves real, painful problems—not just flashy ones.Whether you're a seasoned founder or an aspiring builder, Scott leaves you with practical, hard-earned lessons on resilience, product obsession, and why now is the best (and hardest) time to be building in tech.If you’re curious about scaling an AI startup, raising capital in today’s market, or the mindset required to survive the highs and lows of entrepreneurship, this is an episode you won’t want to miss.🎧 Tune in — and get inspired by another one of Canada's biggest startup innovators. Subscribe to the series for more episodes like this

    57 min

  7. 11/26/2025

    Founder Journey ft. Andrew D'Souza

    Today's episode is sponsored by Sage. Learn more about how they can support you at: www.sage.com/ca/intacct On today’s episode of the Founder Journey, the team was joined by Andrew D'Souza (Clearco and Boardy.ai) who shared more on how he helped to build FinTech giant Clearco, and how that ultimately led to his pivot with Boardy.ai and how he's creating one of the most innovative networking tools you’ve ever seen. Andrew has done it all and is sharing all the takeaways for today’s Founders. Subscribe wherever you listen to your podcasts. You can also watch the entire episode on YouTube Thank you to our podcast partners at StartWell. If you're curious to learn more about their studios and offerings, visit www.startwell.co

    1h 8m

  8. 11/19/2025

    Founder Journey ft. Amar Varma (Part Two)

    Today's episode is sponsored by Sage. Learn more about how they can support you at: https://www.sage.com/ca/intacct On today’s part two episode of the Founder Journey, legendary builder spent time with our hosts Alexandra Reilly and Alex Norman to unpack more of his building perspectives. As an entrepreneur who has successfully build multiple businesses, it was important to spend time discussing exactly how he did. The market looks very different today for builder's and Amar shared valuable expertise on exactly what you need to hit it out of the park. Stay subscribed to the series to hear from more of today's biggest names in tech, who share their authentic and unique stories of success, failure and lessons learned, and how they built some of the biggest companies in the country and globally. Subscribe: https://open.spotify.com/show/5ztGmAp...Thank you to our podcast partners StartWell. You can learn more about how they can support your content and business gatherings at https://startwell.co

    1h 23m
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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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