The Hard Part with Evan McCann

Daniel Eberhard, Founder and CEO of KOHO, a fintech company dedicated to empowering Canadians, shares insights on team dynamics and the impact of AI on business efficiency. He discusses the balance between data and intuition in product development while encouraging a lean staffing approach to boost productivity. Eberhard also dives into the challenges of Canada’s tech identity compared to the US and reflects on the importance of cultural resilience amidst an evolving economic landscape. His humorous anecdotes add a delightful touch to this engaging conversation.

Boris Wertz is the Founder and General Partner of Version One Ventures.This is the second time Boris has been on the podcast; this time, we were able to do it in person.Version One Ventures backs mission-driven founders who are early in new areas such as Ada, Coinbase, Ether.fi, Jobber, Patch, Shippo, Outreach, Uniswap. Chapters(2:45) Introduction to Boris Wirtz and Version One Ventures(5:33) Founder Quality: The Core of Investment Decisions(10:37) Generational Differences in Founders(12:54) Exploring Opportunities in India(14:58) Learning and Building Conviction in New Markets(19:28) Post-Investment Relationships with Founders(21:00) Structuring Version One Ventures(23:34) Reflecting on the Anti-Portfolio(25:37) Liquidity and Fund Management(27:47) Fundraising Insights from a Former Founder(29:41) Shifts in the Venture Landscape(31:44) Common Pitfalls for Emerging Managers(33:29) Opportunistic Investment Strategies(34:41) Investment Stages: Pre-seed to Seed(36:09) Decision-Making in a Lean Team(37:33) Exciting Areas of Investment

Peter Hass is the GM at Stelumar.Stelumar Advanced Manufacturing Inc. (SAMI) is a technology-driven company dedicated to revolutionizing homebuilding in Canada through advanced modular building solutions. Founded by Peter Gilgan, one of Canada’s leading entrepreneurs and the founder of Mattamy Homes, SAMI combines automation, robotics and AI to produce high-quality prefabricated components at an industrial scale. With a state-of-the-art facility set to open in the GTA, SAMI aims to address the housing crisis by making homeownership more attainable, accelerating construction timelines and setting a new benchmark for innovation in the industry.Chapters00:00 Peter Hass: A Journey Through PropTech05:46 Understanding Prefab and Modular Construction09:10 The Advantages of Speed in Construction12:16 Mid-Rise Buildings: The Sweet Spot for Modular13:27 Navigating Regulatory Challenges in Construction17:01 The Impact of Robotics on Manufacturing18:42 Transforming the Building Industry19:59 Dispelling Myths About Modular Construction21:56 Scaling Up: The Future of Manufacturing23:44 Innovations in Home Building25:26 The Cost of Housing: Breaking Down the Components28:08 Customization in Modular Construction30:03 Pricing Strategies in Modular vs Traditional Construction31:08 Current Trends in the Real Estate Market32:45 Policy Changes for Housing Affordability34:17 The Future of Robotics in Construction36:12 Lessons from Peter Gilgin37:27 Finding Balance in Entrepreneurship

Kevin Jia is the Co-Founder of Quoted Tech Computers.Founded in 2023, Quoted Tech was founded by two tech enthusiasts with a clear vision to change the world of hardware.Quoted Tech has served over 10,000 customers across the country and is on track to hit $10M in revenue, completely bootstrapped.Chapters00:00 The Founding Story of Quoted Tech06:24 Building Gaming Computers: The Process and Expertise12:20 The Evolution of Gaming: From Consoles to PCs17:12 Challenges in the Canadian Market: Sourcing and Accessibility19:31 Bootstrapping and Scaling: Balancing Growth and Options20:41 Bootstrapping and Early Challenges24:07 Building Relationships and Partnerships26:51 Marketing Strategies and Customer Acquisition29:54 Customer Retention and Upgrades31:59 Agility in Product Development33:41 Navigating Hard Times and Resilience40:27 Introduction and Importance of Following the Podcast

Philippe-Antoine Lehoux, CEO of Missive, shares insights from his journey of bootstrapping multiple businesses with a customer-first philosophy. He emphasizes the importance of effective team dynamics and the role of AI in enhancing productivity. Philippe discusses innovative approaches to email management, explaining how Missive prioritizes meaningful conversations over clutter. He also reflects on scaling challenges and the balance between user experience for novices and experts, along with strategies for sustaining motivation in the long haul.

Chris Samra, founder of Waves and innovator in wearable technology, shares his vision for camera glasses designed specifically for content creators. He discusses the seamless integration of stylish design and user experience in wearable tech. The conversation dives into the evolving landscape of content creation, emphasizing the role of AR and monetization strategies. Samra also explores the challenges entrepreneurs face and highlights the significance of community engagement in overcoming obstacles. Exciting insights on navigating the startup culture are also revealed!

Jack Newton, Founder and CEO of Clio, discusses his journey in transforming legal technology. He shares the challenges of fundraising during a financial crisis and highlights the importance of perseverance. Newton delves into Clio's core values, emphasizing employee autonomy and a strong company culture. He explores how AI is reshaping the legal landscape, boosting productivity for lawyers, and discusses strategies for scaling while maintaining innovation. Lastly, he reflects on his 17-year commitment to building a lasting legacy in the legal tech space.

Tuner Novak from Banana Capital.Banana Capital is a Pre-Seed/Seed fund, and Turner also hosts The Peel Pod.SupportersFloatBloom SR&ED VanHackTimestamps02:40 - Canadian Roots and Identity07:36 - The Future of Media and Content Creation10:10 - The Importance of Distribution in Venture Capital13:14 - Content Creation and Personal Enjoyment15:40 - The Evolution of Influencer Investing18:40 - Building Relationships and Inbound Opportunities21:21 - Navigating the Investment Landscape24:06 - The Role of Personal Branding in Venture Capital29:05 - Understanding Venture Capital Returns33:54 - Evaluating Founders and Their Potential38:09 - Identifying Market Opportunities42:59 - The Importance of Team Dynamics46:01 - Balancing Work and Family LifeKeywordsCanadian roots, media, venture capital, distribution, content creation, personal branding, investment landscape, founders, market dynamics, work-life balance

James Clift is the Founder and CEO of Durable.Durable makes owning a business easier than having a job. We’re building the world’s fastest AI website builder and all-in-one business platform, so anyone can launch online in seconds and grow with powerful AI tools.Over 10 million websites generated. Used by business owners in 100+ countries.Chapters02:25 James Clift's Entrepreneurial Journey05:54 The Vision Behind Durable07:51 AI's Role in Business Transformation10:59 Website Functionality and User Experience15:40 The Future of Business Ownership17:37 Trends in Business Creation20:55 Navigating the AI Landscape as a Founder26:07 Venture-Backed vs. Bootstrapped Businesses29:37 Lessons Learned as a Founder33:03 The Future of AI and BusinessKeywordsDurable, James Clift, entrepreneurship, AI, website building, business ownership, venture capital, startup trends, user experience, business transformationSupportersFloatBloom SR&ED VanHack

Dylan Itzikowitz is a Principal at South Park Commons.South Park Commons is a community of technologists and builders dedicated to helping each other explore, learn, and figure out what's next—or as they call it, go from -1 to 0. They believe great ideas very rarely come about in isolation. The SPC Fund invests in companies that emerge from their members' explorations, ensuring the community's longevity and supporting the next stage of their founders' journeys.Takeaways- The Brain Drain Debate: Canadians in the U.S. - Commonalities Among Founders- Venture Investing Insights from Expa and SPC- The -1 to 0 Concept at SPC- Identifying Exceptional Talent- Mindset Differences Across Ecosystems (Toronto, SF, London, NYC)- The Evolution of Community Post-COVID - Building Authentic Connections - The Role of AI Tools in Startups - Attracting Talent to South Park Commons - Supporting Founders: The SPC Approach - Scaling Communities: Quality Over Quantity - Maintaining an Edge in Venture Capital - Current Trends in Founding Companies - The NYC Tech Ecosystem Chapters02:41 - Exploring Global Tech Ecosystems 07:13 - The Brain Drain Debate: Canadians in the U.S. 09:08 - Commonalities Among Founders: The Canadian Connection 10:00 - Venture Investing Insights: A Unique Approach 11:23 - Identifying Exceptional Talent: What We Look For 15:25 - Mindset Differences Across Ecosystems 18:02 - The Evolution of Community Post-COVID 20:38 - Building Authentic Connections 22:49 - The Role of AI Tools in Startups 24:02 - Attracting Talent to South Park Commons 25:59 - Supporting Founders: The SPC Approach 27:44 - Scaling Communities: Quality Over Quantity 30:07 - Maintaining an Edge in Venture Capital 32:36 - Current Trends in Founding Companies 34:41 - The New York Tech Ecosystem 36:46 - Key Learnings in Venture Capital 39:36 - The Role of Mentorship in Growth 41:21 - Coping with Hard Times: A Personal Approach KeywordsCanadian talent, venture capital, brain drain, community building, networking, AI tools, startup trends, New York tech, mentorship