The Hard Part with Evan McCann

John Yue is the CEO and Co-Founder of Inference.ai . Inference.ai is a leading Infrastructure as a Service company. Their mission is rooted in the belief that the intelligence of AI is directly proportional to the computational power it harnesses. With the world's largest fleet of GPUs, they empower companies to transform their AI ambitions into reality by providing the computational muscle ne...

Craig D'Cruze is the COO at Inverted Ventures . Takeaways Breaking into venture. Building dealflow and relationships. Starting with some LP investments and moving to direct. Family Office dynamics and their interest in tech. Value add from Inverted's POV. Challenges of raising a fund. The focus on Western Canada. Follow on investments. More liquidity and smaller exits are needed in the eco...

Adam Felesky is the Co-Founder and CEO of Portage . Portage is a global investment platform focused on fintech and financial services. Their team partners with ambitious companies across all stages, providing flexible capital and deliver a global network of investors, commercial partners, advisors and value-creation experts. With deep industry knowledge and entrepreneurial experience, Portage is c...

Vedant Suri is an Investor at General Catalyst . General Catalyst is a venture capital firm that invests in early-stage and growth-stage companies. The firm has offices in the United States and Europe and has been involved in funding and nurturing several high-profile companies. Some notable companies in their portfolio include Airbnb, Stripe, and Snap. Vedant has a really interesting background w...

Lucas Matheson is the Canada Country Director at Coinbase . Takeaways Why Coinbase is excited about the Canadian market. Educating Canadians on crypto and Coinbase Coinbase's offerings including the Coinbase wallet, Coinbase One subscription, Coinbase card, and Coinbase Commerce. The digitization of money and how it creates an interesting transition to crypto and digital assets. The future of...

Matthew Clark is a Media and Technology Executive. Matthew has spent time at Microsoft, Amazon, MasterClass, and Unity in business development. Currently, he is also a Business Development Advisor for Venu Sports (a joint venture between Disney, Fox and Warner Bros. Discovery). Takeaways Breaking into big tech in the US. What does strategic business development actually mean. Negotiating, with a f...

Alyssa Spagnolo is the Growth and Strategy Lead at Banyan Infrastructure . Banyan Infrastructure is on a mission to mobilize capital by modernizing sustainable infrastructure financing. Takeaways Alyssa's founder journey, why it was isolating. Building empathy for founders from the investor side. Joining ScaleUp Ventures and OMERS Ventures Moving and building out the OMERS Ventures office in S...

Zach Zhang is the Co-Founder, Chief Product Officer and President of Clasp . With Clasp, HR and vertical SaaS platforms can offer their customers the ability to buy and manage employee benefits in-product. Takeaways The rise of embedded benefits. The embedded software space with the likes of Stripe and Check. HR unbundling trend. Providing a great product experience. Why health insurance in the US...

Preston Pesek is the Chief Strategy Officer at NatML, previously he was the Co-Founder and CEO of Spacious which was acquired by WeWork. Takeaways Preston's time at SL Green and Fortress Investment Group. Spacious was a capital-light coworking space that activated underutilized restaurant spaces. Spacious had a different supply-side model compared to WeWork. The acquisition of Spacious by WeWo...

Alison Kaizer is the Head of Talent at Golden Ventures . Golden Ventures is a leading seed-stage venture capital fund, based in Toronto and investing across North America. Takeaways Scaling Ritual's hiring and talent process. How to do case studies well in the interview process. How to approach potential hires cold. Questions to ask in interviews. How to run a great interview process. When to...

Pouria Assadipour is the Co-Founder and CTO of Beatdapp . Beatdapp helps music labels and artists track their songs to collect royalties. Beatdapp is a tracking system that authenticates, verifies, and validates media streamed in real-time. It reduces the tracking discrepancies between Digital Service Providers (DSPs) and rights holders, increasing royalty revenue for rights holders while limiting...

Janet Bannister is the Founder & Managing Partner of Staircase Ventures . Takeaways Working at eBay early days. Launching Kijiji in Canada. Getting into VC and joining Real Ventures. How she raised a fund so quickly with Staircase Ventures. Building relationships with LPs. How the venture scene has changed in Canada. Staircase Ventures prioritizes founder support and development, offering CEO...

Priya Monga is the GM & Senior Director of GTM Strategy for Instacart Business . She is responsible for unlocking the growth of Instacart Business, a new emerging segment for Instacart. Lead and manage all go-to-market functions across marketing strategy, partnerships, enterprise sales and customer service. Takeaways Find a job that aligns with your North Star. Getting promotions. Demystifying...

Matt Roberts is a Partner at CMD Capital . CMD Capital is a leading venture capital firm for AI-strong seed-stage startups. They focus on Canadian startups using AI in non-trivial ways, to solve mission-critical problems across B2B and Enterprise sectors. Takeaways The influence of Sir Terry Matthews and Matt's father played a significant role in shaping his entrepreneurial journey. The Canadi...

Jodi Krakower Kessler is a Partner at 3L Capital . 3L is a private equity firm that invests in emerging growth companies. The firm backs innovative founders and management teams across the Commerce, Enterprise Software and Tech-enabled Services landscapes, with a particular emphasis on opportunities where M&A and creative financing strategies can augment strong organic growth. 3L provides mana...

Aleya Velshi and Melissa Donato are the Co-Founders of Alter . Alter is a sauna and ice bath studio in College West, Toronto. Alter's mission is to make hot and cold exposure a more approachable and consistent practice by creating a warm, welcoming, and community-oriented atmosphere and an experience that pays homage to this centuries-old modality. Alter offers flexible drop-in sessions and cl...

Riley Tomasek is the Founder and CEO of Dexa AI . Dexa AI allows you to search podcasts' entire back catalogue. Queries will be matched with summaries and clips from relevant episodes. Your searches are private by default, but you can publicly share your favourite results. Takeaways Early experiences with Indochino. Building a bootstrapped product. Relationship between design and engineering....

Adam McNamara is the Founder and Angel Investor at his family office McNamara Family Investments . Adam previously Co-Founded Select Start Studios (acquired by Shopify), was a VP Product at Shopify, Co-Founded Ramen Ventures and now is a Mentor through CDL. Takeaways Learnings from starting and winding down Ramen Ventures. Why he continues to invest as an angel, focusing on deep tech and supportin...

Tim Lett is an angel investor, entrepreneur, board director, and executive coach at Torlins. Tim founded Axsium Group (acquired by Knightsbridge Human Capital Management) and is an active investor and board member with companies like Top Hat, Alayacare, PartnerStack, CareGuide, WiseDocs and more. Takeaways Workbrain mafia and what made the company and people so special. Starting his own business a...

Solon Angel is the Founder and CEO of a new stealth AI company. He previously founded MindBridge and is an active investor and advisor. Takeaways Why Solon actually didn't want to start MindBridge. His journey at MindBridge and key learnings. Working on AI in 2014 and how different the space looks today. Why founders who have been at their business for 10+ or 20+ years are outliers and not the...

Renae Farough is the Co-Founder and CEO of Kicker . Kicker is a next-generation copilot designed exclusively for sales professionals and leaders. Their innovative solutions integrate seamlessly with Salesforce and HubSpot CRMs, leveraging real-time third-party data and advanced generative AI to supercharge all stages of your sales process. Or as they like to say, "You sell, Kicker does the re...

Jeff Parks is the CEO of Stack Capital . Stack Capital Group is a publicly listed entity on the TSX that looks for disruptive growth and late-stage businesses primarily in Canada and the US to invest in. Their current portfolio includes exposure to Locus Robotics, SpaceX, Prove Identity, Newfront Insurance, Omio, Hopper, Varo, Bolt Financial and Canva. By investing in Stack Capital Group, investor...

Alex Kolicich is a Founding Partner of 8VC. At 8VC, they partner with elite founders to build  transformational technologies that create long-term economic and societal value. They are investors who never stopped being engineers, operators, policymakers, philosophers, and entrepreneurs. They are equally fervent realists and optimists, with an irreverence for convention and a reverence for wisdom....

Christian Levan is Front Row Ventures 's Director of Portfolio Support and a VC Analyst Intern at White Star Capital . Takeaways His military experience in Singapore. How he joined Front Row Ventures. The impact FRV has had on the Canadian VC landscape and helping students land roles in the space. Christian's advice for young people breaking into VC. Landing internships at Inovia Capital a...

Elijah Moore is the Co-Founder and CEO of Endor Health . Endor Health is a digital health platform that simplifies care and pharmacy access for people with diabetes. Takeaways The acquisition of CollageHR by People Corporation and learnings. Eli discovered he had diabetes and built a business to help others living with the disease. Why living with diabetes is unique and involves day-to-day managem...