The Venture Podcast

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.