The Hard Part with Evan McCann

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 SF Jumping into the operator seat at Banyan The Canadian network in SF and what she likes about the tech scene there. Her interest in renewable energy. Chapters 00:00 Alyssa's Journey as a Founder 05:40 Transition to Venture Capital 10:08 Joining Banyan and Focus on Climate Technology 13:35 Becoming an Operator and the Importance of Founder Experience 22:44 Differences Between Canadian and US Startup Ecosystems 30:50 Creating Connection Points for Canadians in the US 35:45 Personal and Professional Excitement 37:54 Dealing with Hard Times 38:01 Journey of an Entrepreneur Keywords founder, venture capital, operator, renewable energy, empathy, specialization, technology, startup ecosystem, thinking big, talent, climate change

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 USA is ripe for disruption. Strong co-founder relationships. GTM strategies for embedded startups. Building partnerships. Chapters 00:00 Zach's Journey to Becoming a Founder 04:56 The Rise of Embedded Benefits 08:14 The Role of Product Managers in a Growing Team 11:16 HR Unbundling and the Potential of Clasp 15:27 Building Trust and Relationships in the Startup World 41:27 Journey of an Entrepreneur Keywords embedded benefits, HR unbundling, insurance industry, product experience, co-founder relationships, trust, hard times, Stripe, benefits, embedded

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 WeWork, which was Adam Neumann's last acquisition. How a successful exit has changed Preston's views on building. How his new venture runs successfully on remote work. Why Preston chose to move to Vancouver from NYC. His interest in AI. Chapters 00:00 From Traditional Employment to Startup: The Journey in Real Estate 05:10 Building Spacious: Insights from Real Estate Finance and Capital Markets 09:47 The Acquisition of Spacious: Lessons Learned 12:34 The WeWork Model and the Demand for Remote Work 15:45 Inspiration and Acquisition 24:45 The Move to Vancouver and Current Work 24:55 Navigating Risks as a CEO and Decision to Move to Canada 26:18 Canada: A Hub for Engineering Talent 26:44 The Disruptive Power of AI 30:41 Building Community in Remote Teams 42:27 Strategies for Dealing with Hard Times as a Founder 46:06 Journey of an Entrepreneur Keywords Preston Pesek, Spacious, real estate, coworking, WeWork, acquisition, remote work, office market, remote work, Spacious, Vancouver, engineering talent, AI, disruption, balance, stress

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 hire someone to oversee your talent and hiring. How to think about compensation. How to think about titles and when to give them out. Chapters 00:00 Joining Ritual in the Early Stages of the Tech Industry 07:02 Scaling the Interview Process to 500+ Employees 11:00 The Unique Path to Golden Ventures 13:23 Key Considerations for Early Stage Companies 16:58 Asking the Right Questions in the Interview Process 20:33 Building a High-Performing Team in a Startup 23:40 Standing Out in the Candidate Outreach Process 27:02 The Importance of Relationship Building in Hiring 29:26 Setting Up for Long-Term Success with Titles 31:15 Building a Network of Trusted Advisors for Hiring Decisions 35:30 Timing and Considerations for Hiring Someone to Oversee Talent 37:48 Aligning Expectations and Culture for the Right Fit 44:39 The Value of Community in Startup Land 45:24 Journey of an Entrepreneur Keywords Golden Ventures, hiring, talent, early-stage startups, cultural fit, case studies, interview process, ATS, Talent Wall, compensation, advisors

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 legal exposure, expensive audit costs, and lawsuits for DSPs. Takeaways How Beatdapp determines if a listen is human. Music industry breakdown. Importance of streaming in the music business. Breakdown revenue sources for streams and artists. Importance of data and AI in the industry. How to build a great engineering team. How to find a technical co-founder. How to hire early engineers for a startup. Chapters 00:00 The Genesis Story of Beatdapp 04:10 The Problem of Fake Streams in the Music Industry 07:53 The Importance of Streams in the Music Business 10:42 Focus and Market Fit for Beatdapp 13:14 The Impact of Generative AI on the Music Industry 17:28 Challenges with Generative AI in Music Creation 22:20 Interfacing with Other Parts of the Business 24:03 Building a Strong Team Culture at Beatdapp 25:53 Qualities of a Great CTO 28:49 Geography and Talent Acquisition 30:51 Attracting Great Engineers to Startups 34:42 Finding and Convincing a Technical Co-founder 36:26 Current Reading and Excitement for the Future 38:48 Dealing with Hard Times as a Founder 39:38 Journey of an Entrepreneur Keywords fake streams, music industry, Beatdapp, revenue, CTO, engineering team, AI, data, streams importance, team culture, startups, entrepreneurship

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 coaching, peer groups, access to health coaches, family statements, and personal financial advisors. Staircase shares carry with portfolio founders to foster a sense of teamwork. Important qualities in founders she backs. Burn rate and PMF. Chapters 00:00 From eBay to Silicon Valley 07:12 Launching Kijiji in Canada 12:30 Transitioning into Venture Capital 25:15 Investing in Seed Stage and Founder Development 32:11 The Role of a Board Member 36:01 Raising a Fund and Building LP Relationships 42:30 Common Missteps After Closing a Seed Round 45:52 Dealing with Hard Times and Persevering 49:39 Journey of an Entrepreneur Keywords Janet Bannister, Staircase Ventures, eBay, Kijiji, venture capital, Canadian venture landscape, founder support, founder development platform, shared carry, founders, growth mindset, talent acquisition, execution speed, relationships, fundraising, burn rate, product-market fit, long-term success

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 the Chief of Staff role. What made leaders at Facebook so great. Working with Fidji Simo at Facebook and Instacart. Launching a startup within a scaling and public company. Zoom out and think about the bigger vision to gain support for new initiatives. Set micro milestones to motivate the team and pivot quickly if needed. Build a network and find a community for support and learning. Embrace imposter syndrome as a sign of being in the right rooms. Chapters 00:00 From Ivy League to Facebook 05:22 Living Abroad and Working with Different Cultures 07:49 The Chief of Staff Role 12:47 Balancing Vision and Detail 22:46 Launching a Startup within a Scaling Company 25:49 Validating Insights and Building the Bigger Vision 28:22 Setting Micro Milestones for Success 30:59 Hiring the Right Team and Dealing with Imposter Syndrome 33:55 The Power of Networking and Learning from Others 39:53 Being Obsessed with Your Strengths and Making Dreams Tangible Keywords career journey, Ivy League, Facebook, living abroad, chief of staff, Instacart, North Star, product role, leadership, vision, operational excellence, communication, influencing without authority, strategic projects, launching a startup, scaling, public company, building new business units, validating insights, zooming out, setting milestones, resourcing effectively, hiring the right team, imposter syndrome, networking, learning, strengths, Fidji Simo

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 Canadian market lacks early-stage lead checks. Finding the first customer and iterating with them is challenging for Canadian entrepreneurs, as they often have to look to the US market for customer adoption. Why Canadian companies don't buy from Canadian startups. The lack of pension money in Canadian venture and Matt's Substack piece that caused a stir. Where the value is in AI. Tactical advice in raising a venture fund. Matt's interest in Canadian tech and venture history. Chapters 00:00 The Influence of Mentors and Role Models 06:44 Taking Ownership and Problem Solving 09:09 The Lack of Early-Stage Lead Checks in the Canadian Market 12:42 Challenges in Finding the First Customer and Iterating 15:07 The Need for a Cultural Shift and More Anchor Tenants in the Canadian Market 27:39 The Influence of Pension Plans on Investment Decisions 29:20 The Role of AI in the Market 33:13 Qualities of Successful Founders 35:42 Addressing Challenges in the Canadian Economy 39:31 Navigating the Process of Raising a Fund 47:49 The Importance of Understanding the History of the Ecosystem 50:17 Collaboration and Support within the Industry Keywords entrepreneurship, venture capital, early-stage, lead checks, Canadian market, customer adoption, investment, Canadian venture capital, pension plans, AI, founders, Canadian economy, raising a fund, history of the ecosystem, collaboration

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 management teams with the capital, perspective, and relationships needed to become category leaders. The firm is based in Los Angeles and New York City. Takeaways Lessons from competitive hockey. Investment banking prepping your for investing. The importance of operating experience. 3L Capital combines the analytical rigour of private equity with the opportunism of venture capital. The balance between growth and profitability. Peer learning among portfolio companies. Tech-enabled vertical roll-ups. Successful M&A at the growth stage requires strong strategic rationale, financial synergies, and the right partners. The focus on NYC and LA and not SF. Their most recent investment Metropolis which raised $1.7B. Chapters 00:00 Competitive Hockey and Investing Lessons 03:46 Strategic Thinking and Listening to Operators 05:09 3L Capital: Combining Private Equity Rigor with Venture Capital Opportunism 07:28 Finding the Balance: Growth vs. Profitability 12:08 The Power of Peer Learning Among Portfolio Companies 22:18 Successful M&A at the Growth Stage: Strategic Rationale and Financial Synergies 24:53 New York and LA: Venture Markets Outside of Silicon Valley Keywords competitive hockey, investing lessons, investment banking, operating experience, strategic thinking, listening to operators, growth versus profitability, peer learning, Canadian tech scene, Metropolis

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 classes. Takeaways Starting a business with close friends and how to make it work. Research needed before launching a physical space. Designing a space to be welcoming and engaging. Building a team that creates a top-notch experience for guests. Structuring scheduling and blend of drop-in and classes. Balance between newcomers and regulars and designing an experience that works for everyone. Expansion is considered based on factors such as product-market fit, replicability, and scalability. Pricing is determined by sustainability, comparable experiences, and the needs and preferences of their guests. Chapters 00:00 Starting a Business with Close Friends 08:12 Research and Due Diligence 09:38 Designing a Comfortable and Approachable Space 22:44 Building a Welcoming and Diverse Team 26:49 Structured Classes and Flexible Drop-In Sessions 27:42 Creating a Unique and Approachable Wellness Experience 34:03 Building a Supportive Community through Events and Collaborations 34:33 Strategies for Expansion and Growth 40:24 Pricing: Balancing Sustainability and Guest Preferences Keywords friends, business, hot and cold therapy, sauna, ice bath, convenience, community, research, self-funded, design, comfort, routine, team, classes, drop-in sessions, cultural origins, personalized experience, wellness, experience, classes, advanced, beginner-friendly, options, flexibility, community, events, workshops, expansion, pricing