Advertise on podcast: Founder Journey | The Untold Stories of the Founder Journey

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.

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

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

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

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

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

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

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

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 episode of the Founder Journey, legendary builder turned investor joined the show to discuss both sides of the coin. In a live studio session with TechTO, Mantle Founder Amar Varma, offered great insights for today's builder's which included, how you need to thinking globally from day one, his perspective as a builder and investor plus everything else today's founder's need to know from someone who has built and exited multiple companies. 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

On today’s episode of the Founder Journey, we hear the authentic Founder story behind LumiQ - a leading educational podcast platform that has redefined the way people learn. Michael Kravshik, Co-Founder and Board Member of LumiQ joined Alex Norman and Alexandra Reilly to share more on building, finding the right team to support your mission and everything today's entrepreneurs need to know. 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. We drop new episodes all month long. 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

On today’s episode of the Founder Journey, we discuss a very inspiring entrepreneurial journey and share the ultimate playbook for today's builders. In a live studio session with TechTO during Toronto Tech Week, Michael Hyatt, the legendary builder, investor, former Dragon on CBC's Next Gen Den and current inspiring tech figure, joined Alexandra Reilly and guest host Marsha Druker to hone in on the Founder Journey. From a very personal beginning into the world of building, all the way to lending his voice and guidance to the next generation of builder's, Hyatt gets very candid on the entire process from start to finish. 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. We drop new episodes all month long. 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

Today's episode is sponsored by Sage. Learn more about how they can support you at: https://www.sage.com/en-ca/ On today’s episode of the Founder Journey, we dive in on all things FinTech, Founder mental health and how to make an impact in a very regulated space. In a live studio session (at StartWell) with TechTO during Toronto Tech Week, COO and Co-Founder of Canadian FinTech powerhouse, Borrowell, Eva Wong, got candid about her unlikely journey into the tech world, balancing motherhood and entrepreneurship, embracing the world of AI and how today's Founder's can truly iterate their ideas in a big way. 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. We drop new episodes all month long. 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

In today's newest episode of the Founder Journey, our hosts Alex Norman and Alexandra Reilly of TechTO sat down with Founder of eSentire, Eldon Sprickerhoff. Eldon, most notably remembered for his breakthrough cybersecurity company eSentire, got candid with the team to share his thoughts on scaling from idea to billion dollar business, how AI has changed the game for builders today, what founders should curious about when starting to build, and how he is now continuing to support the ecosystem as a mentor. Don't forget to like and subscribe wherever you listen to your podcasts, and keep up with us each month for more unique Founder stories. Thank you to our podcast partners StartWell Today's episode is sponsored by Sage Visit Sage Intacct Financial Management Platform and take control of your growth.

In today's newest episode of the Founder Journey, our hosts Alex Norman and Alexandra Reilly of TechTO sat down with CEO of Missive, Phillipe Lehoux. Phil, shared his interesting approach to building a business, how they bootstrapped successfully, advice for today's builders, and how to maintain authenticity as your business and team grows. Don't forget to like and subscribe wherever you listen to your podcasts, and keep up with us each month for more unique Founder stories.

In today's newest episode of the Founder Journey, our hosts Alex Norman and Alexandra Reilly of TechTO sat down with CEO of Clutch, Dan Park. Dan, who has had an extensive career building and launching businesses in Canada, shared how he helped grow Uber Eats Canada, the strategy behind disrupting the car selling market, and how you as a builder can also achieve big things in Canadian Tech. Don't forget to like and subscribe wherever you listen to your podcasts, and keep up with us each month for more unique Founder stories.