The Venture Podcast

At 23, James Flynn became one of the youngest partners in Sequoia Capital's history and has spent the last two years investing on the growth team. James goes into: What actually impresses top-tier VCs How to decide between being an operator vs. an investor The AI opportunities he believes are larger than most people think

Mike Fata co-founded Manitoba Harvest Hemp Foods in 1998 and helped lead the company through its $419M sale to Tilray. Today he spends his time investing in, advising, and mentoring the next generation of entrepreneurs. We tend to interview a lot of people in tech, so it was refreshing to hear a different perspective from someone in the CPG space. Mike goes into: His mindset shift on the importanc...

After 15 years of running at full speed, Scott Barker recently sold everything he owns to travel the world. We’ve had a lot of founders on the show, but very few are willing to talk openly about the cost of chasing big goals for long periods of time. Scott is the co-founder of GTMfund, an early-stage venture firm backed by 350+ top GTM leaders. In this conversation, Scott talks candidly about: The...

Elaine Dai is a Partner at Alt Capital , a new venture firm founded by Jack Altman that backs ambitious founders in AI and enterprise software. In this episode, we dive into Elaine’s journey from Harvard to Microsoft, Norwest, and now Alt, where she helps lead a $275M second fund focused on AI-native companies and category-defining startups. Elaine shares what it takes to recognize outlier founder...

From repairing semi trucks in Alberta, Canada to shaping breakthrough research at Google DeepMind , and now closing a $10 million raise for his applied-AI startup Maneva - Rae's journey is a master-class in turning technical insight and passion into business impact. In our latest (and most technical) episode of The Venture Podcast, we unpack: - How hands-on engineering roots still guide Rae&#3...

Eric Jorgenson is the bestselling author of The Almanack of Naval Ravikant and CEO of Scribe Media. In this episode, we dive deep into agency, accountability, and the mindset behind doing truly original work. Eric shares the viral story behind how he turned a single tweet into a life-changing book project, what it really means to be “high agency,” and how he unexpectedly became CEO of a company he...

In this episode we sit down with Michael Perry , founder of Kit (acquired by Shopify) and current CEO of Maple. Michael shares the truth about his 20-year entrepreneurial journey—from selling cars and living on food stamps to building products used by millions. We dive deep into his early hustle, the pain behind building startups, and the importance of authenticity.

Robbie Bent is the CEO and co-founder of Othership—a venture that reimagines wellness with guided sauna and ice bath experiences. His story offers thoughtful insights on product design, building and scaling a brick-and-mortar business, and creating spaces that foster meaningful relationships. We’re excited to share his perspective with you—enjoy the conversation.

200 VCs wanted to get into Lumen Orbit (YC S24)'s seed round! Over the holidays, James Moffat and I had the pleasure of sitting down with Lumen's Co-Founder and CEO, Philip Johnston. Drawing on his experience as a former Harvard University class president, McKinsey & Company consultant, and entrepreneur with a successful exit, Philip is now turning his focus to the stars. His mission? To revol...

Iguanas falling out of trees onto self-driving cars? For Matt Puchalski, this wasn’t just an odd occurrence—it was a real challenge he and the team at Argo faced when these frozen reptiles disrupted the sensors on expensive autonomous vehicles. On this episode of The Venture Podcast, James and Bryce sit down with Matt Puchalski, the co-founder of Bucket Robotics. Today, Matt is in San Francisco, b...

The largest venture capital raise ever by a Black woman in Canada. A former CIO and Global executive, of BMO and TD.  The founder of a Cybersecurity company winning contracts with countries across the globe.  These are not different people, this is Claudette McGowan, this week's guest on the Venture Podcast. Her message in this clip from our interview is powerful enough to warrant a focused share,...

Kyle Norton is the CRO of Owner, one of Forbes's "Next Billion-Dollar Startups" for 2024. As a limited partner at GTMfund and Stage 2 Capital and with over 15 years of experience leading sales teams at places like Shopify and League Inc., Kyle brings a wealth of insights to the table. He also hosts The Revenue Leadership Podcast, where he interviews top sales leaders, dives deep into growth-drivin...

In episode 20 of The Venture Podcast we had the pleasure of sitting down with Dani and Victoria, co-founders of Mave and Chez—the revolutionary slipper brand that is transforming comfort and style for women. From launching their first business out of college to creating a company that’s reshaping the slipper industry, Dani and Victoria's story is a masterclass in starting a business. Their biggest...

At just 23, Conor has already built and sold his own AI startup, Cycle, and has an incredible amount of insight to offer from his journey this far. In just a few short years, Conor has packed in experiences that many people don’t reach in a lifetime, and his insights prove that ambition, grit, and a willingness to fail can fast-track your journey to success. Here are some key takeaways from our co...

In this episode of the Venture Podcast, we sit down with Akshay Chalana, founder of Saphira AI and a member of Y Combinator’s Summer 2024 batch. Akshay’s journey—from overcoming a childhood speech impediment to working at Tesla, Facebook, Apple, and Citadel and now leading his own AI startup—offers profound insights into finding your path in tech, entrepreneurship, and life. His story is a powerfu...

In this episode of The Venture Podcast , we had the privilege of sitting down with Rod Boothby, in Salesforce Park. Rod’s journey shows the significance of lifelong learning—from selling baseball hats at Queen’s University, including one worn by Elon Musk during his time there, to co-founding one of the most widely used software tools in the world—NPM (node package manager), to his leadership at c...

We sat down with the man who has built the largest and most successful boat rental marketplace in the world: Sascha Mornell. Sascha’s story is extraordinary. From Berkeley to Japan, Harvard Business School, the NBA, and leading three multi-hundred million to billion-dollar startups, including taking one public. In this conversation, we dive into Sascha’s life and explore valuable lessons for anyon...

Andrew Miklas , a current visiting group partner at Y Combinator and co-founder of PagerDuty . Andrew shared his journey to product-market fit with PagerDuty, starting a venture fund with an old Waterloo friend, and his time both as a batch member and visting group partner at YC. Here are a couple pieces of advice he has for aspiring founders: 1. Learning how to code is still vital if you want to...

Kate Wallace is the Co-Founder and head of product at Tally Labs - a Web3 media company that is changing the future of storytelling (Check out their new mobile App @Avenue). Before starting the company, Kate attended The Parsons School of Design, was accepted to several well-known fellowships such as Next 36, NYC Media Lab, and Kleiner Perkins, and worked as a product manager at Better Mortgage an...

Vino is a Forbes 30 Under 30 honoree, a former Facebook employee from the early 2010s, and an accomplished entrepreneur with three exits. In this episode, we discuss Vino’s life journey, including how he dropped out of university after his second year to work full-time at Facebook. We break down the insights he gained at Facebook in the direct-to-consumer space and explore how he applied these les...

Roy Itzhaki is the founder of BizDev Labs - an outbound BDR agency trusted by over 70 high-growth startups. BizDev Labs helps B2B SaaS companies develop their go-to-market strategies and has generated over $1 million in profit annually. Before he started BizDev Labs, he was an Olympic-class windsurfer, graduated from the Smith School of Business at Queens, and was a top performer in various BDR ro...

Daniel Mazour and Michael Spivak are the co-founders of Coldture - Canada’s first and only proudly Canadian cold plunge tub. Michael and Daniel both come from immigrant families and share how the values of accountability, perseverance, and risk tolerance contributed to creating a category-defining brand in the Canadian market. The two have previously appeared on Dragons’ Den where they inked a dea...

Cameron Rowe is the founder and CEO of Hover - Canada's first publicly available drone delivery service on the Toronto Islands. Cameron received a Master's from the Smith School of Business and has since had a ton of experience in the entrepreneurial world between starting many businesses and working with various entrepreneurial communities such as Techstars, Next36, FreshFounders, and Dra...

Nelson Lang is the Founder of Pita Pit, a quick-service restaurant with over 600 locations worldwide. Nelson founded the company in his late twenties and built it into the massive franchise restaurant brand it is today before selling the company to Foodtastic in 2021. With no intention of retiring, Nelson bought Lightcaster Brewery and is now the managing partner. Listen in as Nelson shares his st...

Jonathan is the Founder of Captain Experiences, an online platform that connects adventure-seeking people to tour guides, primarily for fishing and hunting trips. Jonathan was a business student at the University of Georgia and worked various investment banking roles in the energy sector when one day, he was tasked with booking a celebratory fishing trip for his team after completing a successful...