The Hard Part with Evan McCann

Klaudia McDonald is the Co-Founder & COO of Bobo. Bobo’s mission is to make parenting easier, cheaper & more straightforward than ever before. The Bobo platform provides AI-driven support to recreate the 'village' needed for parenting. It reduces the mental load by offering tailored, stage-specific support, making the prospect of having children more appealing & manageable. Takeaways Working at Just Eat Takeaway. Launching international markets. Challenges that parents face. Attracting users to Bobo. Utilizing AI. Leveraging accelerators. Partnerships with influencers and vendors. Building a co-founder relationship with your spouse. Managing ADHD as a founder. Take advice only from individuals who are a few steps ahead of you and align with your values and vision. Chapters 00:00 Working for a Global Organization 03:28 Building a Great Product 04:43 The Birth of Bobo 07:07 Challenges Faced by Parents 09:32 Unique Strategy for Bobo 09:53 Attracting Users and Expanding 11:55 Comprehensive Offering for Parents 13:15 From Conception to Early Childhood 15:47 Utilizing AI for Personalization 17:42 Leveraging Accelerators 19:53 Balancing Co-Founder and Spousal Roles 21:50 Managing ADHD as a Founder 24:46 Embracing Opportunities and Taking Risks 25:57 The Power of Content Curation 27:44 Launching into Different Markets 30:27 Navigating Immigration and Choosing Canada 34:00 Finding Purpose in Challenging Times 36:20 Taking Advice from the Right People 37:09 Journey of an Entrepreneur Keywords Klaudia McDonald, Bobo, Just Eat Takeaway, parenting, support, resources, localized information, curated content, partnerships, influencers, co-founder relationship, ADHD, advice

Mark Mitchell is a General Partner at Weave VC. Takeaways Mark's journey into VC. Living in China for over a decade. Starting with SPVs and launching Weave VC. Co-Founder relationships with Jeff and Marco. Investing in Western Canadian tech. Fundraising as first-time fund managers. Journey of an emerging manager. Recent investments. Chapters 00:00 Mark's Journey into Venture Capital 03:39 Building a Track Record: Angel Syndicates and SPVs 06:35 The Genesis of Weave 09:08 Co-Founder and Partner Relationships 10:50 The Focus and Vision of Weave 16:52 Investing in Western Canada's Tech Ecosystem 19:19 Investor Relations and Fundraising 22:01 Traits of Successful Founders 22:21 Trends in Western Canada's Tech Ecosystem 23:36 Recent Investments: Retreats and Venues, Reds VR 26:41 The Journey of an Emerging Manager 32:04 Recommended Reading: 'Read Write Own' by Chris Dixon 35:11 Mark's Excitement for the Future 37:13 Dealing with Challenges and Finding Balance 37:18 Final Message: Keep Building and Persevering 37:59 Journey of an Entrepreneur Keywords venture capital, startup ecosystem, emerging manager, founder-market-product fit, Canadian tech scene, fund closing, physical outlets, family

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 needed for smarter, more efficient AI. Takeaways Competing with the big three (AWS, Azure and Google) and why there is need for new players. What it takes to build an infrastructure company and what infrastructure as a service (IaaS) means. A deep chat around GPUs, the space, the industry dynamics and challenges with shortages. Discuss why a16z is stockpiling GPUs and giving access to their portcos. The shortage of GPUs is expected to last for 7 to 10 years. We discuss the dynamics of LLMs and inferencing. Advantages of being in the Bay Area with an AI startup. Chapters 00:00 Building a Better Cloud Storage and Infrastructure 04:45 Competing with AWS and Finding the Gap in the Market 07:41 The Long-Term GPU Shortage and the Need for Creative Solutions 11:21 Stability, Flexibility, and Affordability: Key Factors in Attracting Customers 18:36 The Future of the Big Three and the Rise of New Infrastructure Providers 21:04 The Benefits and Challenges of Being in Silicon Valley 25:09 Finding Advisors and Investors with AI and Hardware Expertise 30:33 Now is the Time for Canadian Founders to Start AI Companies 42:17 Journey of an Entrepreneur Keywords AI infrastructure, GPU shortage, inferencing, Silicon Valley, founders, AI boom

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 ecosystem to attract more capital. Chapters 00:00 Breaking into the Venture Space 03:54 Finding Deal Flow and Building Relationships 05:40 Investing as a Family Office 07:50 Strategies for Getting Involved in Tech Investments 08:15 Navigating the Space: Strategy and Execution 11:01 Being a Value-Add Investor 14:18 Pattern Matching in Founders 17:26 The Importance of Geography in Investing 20:07 Follow-On Investments and Fundraising Strategy 22:49 Common Challenges in the Western Canadian Ecosystem 24:42 LP Conversations and the Need for Liquidity 27:13 Dealing with Hard Times and Staying Balanced 29:43 Looking Forward: Goals and Aspirations 35:03 Closing Thoughts: Building a Strong Ecosystem 43:15 Journey of an Entrepreneur Keywords venture capital, relationships, founders, investors, Western Canada, liquidity, exits, family offices, fundraising

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 committed to supporting the leaders who are reshaping financial services. Takeaways Starting Horizons ETF and nuances to the ETF business. The founding story of Portage. Fintech in Canada and Portage's portfolio companies Wealthsimple and KOHO. Secondary funds and liquidity. Regulatory environment in Canada and open banking. Building an investment team globally. Infrastructure and AI are promising areas in the fintech space. Portage's different funds and their relationship with Diagram Ventures. The importance of timing. Chapters 00:00 The ETF Landscape in 2005 and Building a Successful ETF Business 07:47 The Growth of the Fintech Ecosystem in Canada 10:49 The Importance of a Supportive Regulatory Environment for Fintechs 12:01 Timing and Opportunities in the Fintech Market 17:34 Investing in Local Winners and the Role of Incumbents 20:15 Portage Ventures and Diagram: Investing in Going Concerns and Building Companies from Scratch 24:20 Building a Complementary Team and the Importance of Team Dynamics 26:18 The Role of Board Members and Supporting Portfolio Companies 28:25 Liquidity Options for Investors: Secondary Funds and IPOs 30:40 The Regulatory Environment and the Need for Open Banking 32:44 The Future of Fintech and the Importance of Consumer Access 33:30 Qualities of Successful Founders and Building a Clear Vision 34:11 Investing in Infrastructure and AI: Opportunities for Growth and Innovation 38:38 Journey of an Entrepreneur Keywords Adam Felesky, KOHO, Wealthsimple, Horizons ETFs, Portage, ETF landscape, fintech market, challenges, opportunities, infrastructure, AI, complementary team, support, ecosystem

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 working at startups, Goldman Sach's TMT team, BCG and CapitalG. Takeaways Invest in companies with ambitious founders who are domain experts in their respective fields. Focus on both the infrastructure layer and the application layer of technology. Explore spaces like observability, industrial software, vertical AI, and HR software. Consider founder market fit and founder product market fit in investment decisions. Transitioning from consulting to growth-stage investing. Mentorship is valuable in learning the ropes and navigating VC. Be character-consistent and run your own race as an investor. Develop a mix of inbound and outbound deal flow by building sector expertise. Have a prepared mind when evaluating opportunities and understand the market, product needs, and potential risks. Tastemakers are influential individuals in the ecosystem who can provide valuable insights and connections. Great board members are engaged, prepared, and provide steady guidance during crucial moments. The Canadian tech ecosystem has exceptional founders but could benefit from dreaming bigger. Chapters 00:00 Working at Earlier Stage Tech Companies 05:09 The Importance of Founder-Market Fit 07:22 Skills Learned in Investment Banking and Consulting 12:07 Qualities of a Great Board Member 15:04 Dreaming Big in the Canadian Tech Ecosystem 43:58 Journey of an Entrepreneur Keywords investing, ambitious founders, domain experts, infrastructure layer, application layer, observability, industrial software, vertical AI, HR software, founder market fit, founder product market fit, growth stage investing, mentorship, character consistency, deal flow, prepared mind, tastemakers, board work, Canadian tech ecosystem, standing out

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 money. Coinbase Ventures and the investments they have made. Working with government and regulators. Announcement of Stand with Crypto in Canada. Chapters 00:00 Lucas Matheson's Role at Coinbase and the Mission of the Company 04:07 The Role of Technology in Solving Financial Inequality 06:32 Coinbase's Offerings: Retail, Institutional, and Developer Services 10:20 The Transition to Digital Assets and the Future of Money 16:50 Driving Adoption: Easier Use Cases and Access to Digital Assets 20:12 Education and Awareness: Understanding the True Potential of Crypto 23:21 Upcoming Initiatives and Opportunities in the Crypto Space 33:45 Tech Leaders in Canada: Advocating for Change and Productivity 35:53 Journey of an Entrepreneur Keywords Coinbase, Canada, crypto, DeFi, digital assets, education, government, banks, investments, capital gains tax

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 focus on startups interacting with big tech. Engaging with platform companies and things to be aware of. Startups and founders should avoid negotiating term by term and instead focus on the overall value and strategic alignment of the deal. Startups should be thoughtful and careful when engaging with platforms. What decision-makers you should speak with at big tech companies to get deals done. How TV has changed with streaming. How AI makes it cheaper and easier to create good enough quality content, disrupting traditional production methods. How to make exclusive content successful. The future of media + technology. Chapters 00:00 Breaking into the Big American Tech Space 04:39 The Intersection of Media and Technology 07:06 Strategic Business Development and Negotiation Tactics 10:53 The Changing Landscape of Content Creation 28:34 The Significance of Exclusive Content and the Platform Shift 46:38 Journey of an Entrepreneur Keywords strategic partnerships, business development, media and technology, negotiating deals, platform companies, startups, media industry, product market fit, TV, content creation, AI, exclusive content, platform shift, Amazon, Venu, Venu Sports, Microsoft, Netflix, YouTube

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