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 VCsHow to decide between being an operator vs. an investorThe 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 importance of personal brand buildingWhat success has looked like inside portfolio companies like Mid-Day SquaresHow to effectively test and bring a CPG product to marketWhy delayed gratification is still the ultimate advantage in businessWhat separates great founders from everyone else

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 mentality that made him successful - but also nearly destroyed himHow easy it is to lose yourself in constant achievementWhat finally made him walk away from the life he builtHis learnings from a career in tech and VCHow ambitious people can build a great career without burning themselves out

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 founders, how she evaluates “slope over snapshot,” and why the best VCs act as invited guests rather than helicopter investors. She also reflects on risk-taking, the immigrant mindset, and why being in San Francisco compounds serendipity.We also cover:Why “AI-native” beats “AI-wrapper” startupsHow to find (and stress-test) the right co-founderPractical advice for breaking into VC without a traditional backgroundThe hardest parts of conviction, patience, and playing the long game

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's product decisions- A few massive lessons learned at DeepMind that every founder should steal- Why Applied AI is where the real value livesIf you lead, build, or invest or in AI, Rae's journey and insights shared will likely be of great value to you.

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 helped rescue from bankruptcy.We also cover:How to build “luck surface area”Pulling back the curtains on the venture capital industryThe secrets to wealth and happiness And how to navigate your 20s with clarity and ambition

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 revolutionize computing with solar-powered, orbit-based data centers that could redefine energy efficiency and scalability for AI. Key Takeaways: 1. Be bold: The biggest opportunities often lie in “zero-billion dollar markets”—industries that barely exist today but have massive potential, like computing in space. These untapped frontiers, often adjacent to big markets, are where transformative breakthroughs and category-defining companies are born. 2. Falling Launch Costs Are a Game-Changer: Rockets like Starship will make getting mass into orbit 100x cheaper, unlocking opportunities like space-based data centers and other frontier innovations. 3. First-Principles Thinking Wins: LumenOrbit tackles challenges by reducing them to their core engineering problems—like designing lightweight, cost-effective radiators capable of dissipating heat in the vacuum of space, a fundamental hurdle for high-energy applications. 4. New Industries Offer Rapid Expertise: In emerging fields like AI and space tech, focused effort can make you an expert in months. Aspiring entrepreneurs and new grads should target fast-growing industries with room for newcomers.

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, building his own robotics startup after an impressive summer at Y Combinator as a new venture partner at PioneerFund. At Bucket Robotics, Matt is transforming how manufacturing detects defects by leveraging cutting-edge robotics and computer vision. Instead of relying on slow, manual quality assurance processes, Bucket Robotics uses synthetic data and advanced AI to inspect complex 3D parts with unmatched precision. What started as a simple idea during Y Combinator—building smarter vision systems—has evolved into a solution that’s helping manufacturers save time, improve accuracy, and optimize QA in numerous manufacturing processes. Here are some key takeaways from our conversation with Matt: 1. Kindness and Intellectual Humility as Leadership Traits: Matt attributes much of his success to being kind, listening well, and staying curious. These qualities have helped him build strong relationships, foster trust, and navigate the uncertainties of entrepreneurship with resilience and optimism. 2. Adaptability and Problem-Solving in Robotics: Matt’s experience at Argo AI highlights the unpredictable challenges in robotics, like adapting self-driving systems to environmental oddities (e.g., iguanas falling on sensors). Success in robotics stems from robust problem-solving frameworks, continuous learning, and assembling a team capable of adapting to real-world complexities. 3. Iterative Learning and Building: The inception of Bucket Robotics showcases the power of starting with broad ideas, engaging with customers, and iterating rapidly to solve specific pain points like defect detection. This iterative approach helped refine the company’s vision and product-market fit, underscoring the value of feedback-driven development. 4. The Power of Community and Curiosity: Matt emphasizes the importance of surrounding yourself with supportive, curious, and knowledgeable people. Meaningful collaboration and asking thoughtful questions are key to both personal and professional growth.

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, so we'll be highlighting one key takeaway from her interview through this clip.

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-driving strategies, and asks radically transparent questions. In this episode, we dive into Kyle’s approach to scaling startups, hiring and training teams, and using AI in sales—packed with advice for anyone aiming to lead in revenue and tech.

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 lesson: you don’t need to have everything figured out from the start. Just take the leap, surround yourself with people who support your vision, and adapt as you go.Here are some key takeaways from our conversation:Start Before You're Ready: When CBC’s Dragon’s Den came calling, Mave and Chez hadn’t even fully launched yet. Instead of hesitating, they seized the opportunity and turned it into an incredible moment of exposure for their brand. Sometimes, the best opportunities come when you least expect them.Resilience and Pivots Are Critical: Dani and Victoria quickly learned that success isn’t a straight path. From running events to launching a product in the middle of a pandemic, they mastered the art of pivoting fast and turning challenges into triumphs.Focus on What Matters: While many might aim for a broad market, these founders honed in on creating a high-quality, ergonomic slipper tailored specifically for women—prioritizing both style and support. Knowing your audience and serving them well is key to growth.Strong Partnerships Make All the Difference: Co-founder relationships aren’t easy, but the bond between these two founders is incredible. They credit their success to their mutual trust, open communication, and the emotional intelligence to clear any misunderstandings before they become an issue.

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 conversation: Experiment in your 20s: Conor emphasizes that your 20s are a time for exploration. Whether it's working in a new city, trying out a different industry, or starting your own company, the more experiences you collect, the better you understand what you truly want to do. Flip the disadvantage into an advantage: Applying to McKinsey Toronto was tough, so Conor looked globally, landing a position at McKinsey Budapest. His lesson—when you're at a disadvantage, find a way to change the game, making your weakness a strength. The power of failure: Conor shared how many of his startups didn’t work out, but those failures were crucial for his growth. He believes in learning from setbacks, keeping your ego in check, and embracing failure as part of the entrepreneurial process. Start with what you can give, not what you can get: Whether it’s building relationships or seeking opportunities, Conor’s advice is to always think about what value you can offer before asking for something in return. It’s a principle that’s shaped his career success.

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 powerful reminder that what seems like a challenge today can become your greatest source of motivation. Key Takeaways from Our Conversation: Follow What Excites You: Akshay’s core advice for students and early-career professionals is to pursue what excites you. Whether it was his childhood fascination with cars or his drive to solve real-world problems through robotics, he believes that letting your curiosity and excitement guide your career decisions is crucial. It keeps you energized and fuels success, even in the face of challenges. Build Independence: At Tesla, Akshay learned one of his most valuable lessons: how to “figure things out.” With minimal guidance, he developed a problem-solving mindset that he now applies to building his own company. This mindset is essential for any aspiring entrepreneur—embrace challenges, learn on the go, and build your independence. Surround Yourself with the Right People: Akshay was deeply influenced by the engineers, entrepreneurs, and creators around him—people passionate about building. His advice to young professionals is to seek out environments that push you to grow. Surround yourself with people who inspire you, challenge you, and share your drive. The right community can accelerate your journey and open doors you never knew existed. Iterate Toward Product-Market Fit: Akshay shared insights into Saphira AI’s ongoing journey to find product-market fit. He emphasized the importance of staying open to change, continuously refining your product, and turning uncertainty into “execution risk”—a challenge that can be solved through iteration and improvement.

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 cutting-edge companies like Joyent and ID Partner Systems. Here are a few key takeaways from the conversation: Bottom-Up Sales: Many of Rod's early successes in business development, such as landing big clients like Walmart and Visa, came from identifying passionate internal advocates within those companies who believed in the product. A key strategy was empowering developers to use the product and demonstrate its value to their bosses, which helped the product essentially sell itself and eliminated the need for long sales cycles. Ecosystems > Product:  Rod highlighted the importance of building ecosystems around a product where users and contributors play a role in its growth. NPM’s success was built on its strong community involvement, ease of contribution, and the ability for others to participate in the system’s evolution.  VC Funding Advice:  Rod advises delaying VC funding for as long as possible, advocating for building up customer traction and revenue streams before seeking outside investment. This provides better negotiating power and helps avoid giving away too much equity early on. He also suggests understanding the venture capitalist’s business structure and practicing pitches and refining answers to potential objections before approaching serious investors. Entrepreneurial Environment:  Rod believes in fostering environments that encourage entrepreneurship. He noted that in places like San Francisco, optimism and encouragement are critical cultural traits that help entrepreneurs succeed, and Canada could benefit from adopting this mindset more widely. 

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 anyone starting their career, whether it’s startups or the corporate world. Check out the episode through the link in our bio.Here are a couple of takeaways from the conversation: 1. Embrace Uncertainty: Don’t feel pressured to have a clear career path from the start. Sometimes, what you perceive as the ultimate goal may not turn out to be what you expected - Sascha thought he had found his dream job at 28, but it ended up being far from the truth. So allow your interests to evolve, remain adaptable and be open to exploring new directions. 2. Do Hard Things Early in Your Career: Sasha's experiences—from navigating cultural and ethical dilemmas in Japan to thriving in the competitive environment at HBS—helped him develop thick skin and resilience. These qualities became essential as he faced the inevitable challenges of building startups. 3. Conviction - When the majority opposes your viewpoint, it’s crucial to trust your instincts. If you have strong conviction, dive in, commit fully, and make it happen. Sascha experienced this firsthand with his defence contracting company, Phacil. Despite venture capitalists’ hesitation to invest in defence tech or government contracting, Sascha’s unwavering belief in his vision led him to scale Phacil into a highly profitable company with $150M in ARR and over 1,000 employees. 4. It is a Great Time to Be Alive - Sascha believes we are living in the most exciting time in human history. The rapid growth and opportunities across industries are unprecedented. Embrace these possibilities and pursue whatever interests you—you’re only limited by your imagination.

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 go into tech - being able to accurately describe the product you want is a skill, and that skill is developed by writing code. A number of coders end up being excellent writers because they learn clarity of thought. 2. Without work experience, it is hard to generate startup ideas outside the scope of a student. Your ideas are often “tarpit ideas” - startup ideas that seem appealing but have been tried by many founders before with little success. It doesn’t take a decade of work experience either, it took Andrew four co-op experiences to find his idea. 3. You don’t need to work at a tech company. Working at a company where you gain experience and understand areas of the business that can be automated can lead to a strong idea. Andrew has seen people develop very successful startups after working in and out of tech. 4. On building an AI startup - If a product is built merely to compensate for a deficiency in an AI model, it likely will not have long-term viability as a business. He believes that a successful solution integrates AI as part of a broader system, not just as an isolated component. What truly makes a product endure is when it becomes the workflow mechanism for a specific type of job, serving not only as a tool but also as the central hub where information is stored—a system of records. This integration into the workflow is what sustains its relevance and value. 5. When angel investing and evaluating teams to back, a strong indicator of a good investment is leaving a meeting with a sense of having learned something new. If you walk away feeling smarter, with a deeper understanding of a particular aspect of the tech industry—or even the world—that’s a very promising sign.

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 and Peleton. Kate shares her story about how a passion for design led her to a career in tech, a product launch that generated $2M in revenue within 6 minutes of release, and the importance of seeking discomfort early on in your career.

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 lessons to build and scale successful ventures. Vino also shares valuable advice like not overthinking everything as a lifelong commitment, and having a bias toward taking action. 

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 roles out of school. Listen in as Roy shares what made him so successful as a BDR, his secret formula for cold email and outreach, and how he grew BizDev Labs to several reputable clients without even having a website.  

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 deal with Michelle Romanow.

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 Dragon’s Den.  Listen in as Cameron shares his experience as a solo founder of a drone company, his passion for endurance sports like marathons and Ironman’s, and all the ups and downs he's had in his journey so far.

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 story all the way from getting kicked out of the house in grade 11, owning his first restaurant at 21, to founding Pita Pit and turning it into a global success. Chapters: 1:00 - Childhood and Early Years 3:00 - Nelson's First Restaurant 9:00 - Kingston Restaurant Market 13:00 - First Customer 15:00 - Franchising and Expansion 20:00 - First Competitor 25:00 - Work Hours 28:00 - Pita Pit Adversity and Financial Trouble 31:00 - New Venture: Light Caster Brewery 34:00 - International Franchising 36:00 - Fraud Pita Pit in Korea 38:00 - What makes a good Franchisee? 41:00 - Partners and Ownership 44:00 - Restaurant Industry Finances 48:00 - Advice to Aspiring Entrepreneurs 53:00 - When the switch flipped to become an Entrepreneur 55:00 - Career Paths out of University 58:00 - Competition 1:00:00 - Fear of Failure and Perseverance 1:02:00 - Family Owned Business's 1:05:00 - Selling Pita Pit 1:08:00 - Nelson's New Venture 1:14:00 - Nelson's First Jobs 1:15:00 - Being the Boss 1:16:00 - Final Takeaways and Advice

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 deal. It was at this moment that he noticed there was an opportunity in the market to help people find and book fishing trips quicker and easier.  Listen in as Jonathan shares his journey building a company in an area he’s been passionate about his whole life, his involvement with Techstars, and all the learnings he's had along the way.

Trent is the founder of SAXX, a men's comfort underwear brand. Trent started his journey as a student-athlete at the University of Nevada-Las Vegas and soon after completed his MBA at Ivey Business School. It was at Ivey where Trent had the vision for SAXX to which he pitched for the Ivey New Venture Project. The rest is history as SAXX has gone on to become a multimillion-dollar company. But Trent didn't stop there, he then went on to found three other successful companies in the wellness space.  Listen in as Trent shares his founding story, his experience building multiple ventures, and the advice he has for young people to start compounding experiences, relationships, and knowledge.

Nikita Kopotun is the Co-founder and President of Juniper which provides custom merchandising solutions for the world’s largest online creators. Nikita started Juniper in 2016 and bootstrapped the company to over $150M+ in revenue. In this episode, Nikita opens up about his journey from being an engineering student at Queen's, his experience with Cansbridge Fellowship living and working in China which changed his whole worldview and perspective on what to do after school, building companies and failing, and the trials and triumphs of launching Juniper. He also offers some great advice to students and entrepreneurs about not waiting for the perfect moment and the importance of learning by doing. I'm lucky to have caught Nikita fresh off travelling the world for the last year and a half, so listen in on his takeaways from this experience and life lessons that have enriched his personal and professional life.

Brandon Afari is the Co-founder and CEO of chargeFUZE - a provider of portable chargers for rent to consumers at static locations. Brandon shares his journey from earning a Bachelor's in accounting and a Master's in taxation from USC, his experience working at Deloitte where he learned the importance of understanding accounting principles when starting any business, and his decision to leave and pursue his venture.

Luke de Haas is the Co-founder and CEO of Mosea - a mobile payments platform with a focus on group payments, bill splitting, and organizing events. Luke shares his story from starting the company right out of university, dealing with the hardships of a start-up, persevering in the face of wanting to quit, and all the rewarding experiences and important lessons he learned along the way.

Chris is the Co-founder and President of Convictional - the #1 modern dropshiping platform for retailers and suppliers. Convictional is backed by Y-combinator and was one of the top 10 startups from Y-Combinator W19 demo day. Chris shares his story from being a Queen's student studying commerce, his experience with on-campus recruiting, working for Shopify, attending the Y-Combinator startup school, and his founding story. Chris provides some extraordinary advice for aspiring entrepreneurs and students trying to answer the question of "What's next?".

Connor is the youngest person in the world to complete an Ironman Triathalon on six continents and will soon be the first person in the world to complete an Ironman on all seven continents. To make this happen, Connor is taking on Antarctica in less than a month. Listen to Connor's incredible Ironman journey and his inspiring message to "dare to dream". Follow Connor's Journey to Antarctica at the following links: Instagram: https://www.instagram.com/connor.emeny/?utm_source=ig_web_button_share_sheet&igshid=OGQ5ZDc2ODk2ZA== LinkedIn: https://www.linkedin.com/in/connoremeny/ Fundraising Link: https://www.gofundme.com/f/chasing-antarctica-documentary?member=29927805&sharetype=teams&utm_campaign=p_na+share-sheet&utm_medium=copy_link&utm_source=customer Website: https://www.chasingantarctica.com/

Preston shares the story behind Chubbies (nine-figure Acq in 2021) and his personal journey from Stanford, followed by "working for the man", to finding his calling in the entrepreneurial world. Preston leaves us with inspiring thoughts for those contemplating life post-university and the entrepreneurial path. Continue following Preston here: https://www.linkedin.com/in/prestonr/