The Hard Part with Evan McCann

Sylvia Ng is the CEO of ReturnBear, a platform for circular e-commerce logistics. With over 18 years of experience in technology, Sylvia noticed a gap in the e-commerce industry, where retail returns were costly and difficult for merchants. Now, Sylvia is on a mission to make retail returns accessible for everyone, and better for the planet. Sylvia has worked at eBay and Google, and most recently was General Manager at Shopify where she worked on products to help early-stage e-commerce merchants grow their businesses. In conjunction with her current role, Sylvia is also the founder of Amidira, a Toronto-based startup helping cancer patients with lifestyle content.  ReturnBear is a returns platform powering Canada’s first end-to-end reverse logistics network. Founded in October 2021 with a mission to make returns convenient for consumers, profitable for brands, and better for the planet. Brands using ReturnBear can offer self-serve returns to their customers, along with convenient drop-off options for immediate refunds. They can count on ReturnBear to gain visibility into returns across sales channels, save on return shipping costs, and get products back into forward supply faster. Takeaways Sylvia's time at UWaterloo during the dotcom bubble, working at iconic companies like Google and Shopify. Product management roles can vary across companies and industries, with different focuses on engineering, design, or data-driven approaches. A new concept to me "micro-forward fulfillment". How merchants should be thinking about returns from a tech stack, logistics and consumer experience. The environmental and time-consuming process of returns and how ReturnBear fixes that. Expanding drop-off locations and implementing micro-forward fulfillment can improve the convenience and profitability of the return process. Geographic expansion is driven by matching supply and demand and opening hubs in strategic locations. Chapters 00:00 University Experience and Tech Industry 02:05 Diverse Work Experience 03:40 Working at Google 07:36 Product Role at 500px 09:20 Understanding Product Management 11:48 Product Line at Shopify 13:19 Inspiration for ReturnBear 15:56 Challenges of the Return Process 18:32 Drop-off Locations and Convenience 24:13 Improving Profitability for Merchants 29:49 Logistics Challenges and Solutions 34:07 Transition from GM to CEO 36:10 Team Composition and Culture 38:20 Micro-Forward Fulfillment 43:25 Geographic Expansion 45:19 Favorite Book and Excitement for 2024 47:39 Dealing with Hard Times 47:56 Coping with Depression and Self-Doubt 49:06 Finding Inspiration and Perspective 49:39 Connecting Consumers and Brands 49:54 Opportunities at ReturnBear

Andrew Kim is the CEO and Co-Founder of SHARE. SHARE is a real estate investment company that streamlines the end-to-end process of buying and managing high-return single-family rental homes on behalf of investors in the US, Canada, and abroad. They make investing in and owning real estate as easy as stocks by enabling investors to reap the benefits of real estate ownership without the burden of full-time landlord duties. Takeaways Share aims to make the US single-family rental market more accessible to retail investors by providing institutional-grade asset management. His early ventures Joyus and Kingmaker. Andrew's time at Loblaw Digital from the early days to scaling to hundreds of people. The impact of higher interest rates on real estate. Venture-backed versus bootstrapped. Keeping a small and lean team. Chapters 00:00 Early Ventures: Joyus and Kingmaker 04:00 Joining Loblaw Digital 07:18 Leaving Loblaw Digital and Starting Share 11:23 The US Single-Family Rental Market 16:00 Scaling the Business and Team Composition 21:05 Impact of Interest Rates on Strategy 23:16 Competition and Future Growth 25:18 Motivation and Drive as a Founder 26:13 Team Composition and Lean Operations 28:44 Venture vs. Bootstrap and Maintaining a High-Performing Team 32:15 The Startup Scene in Toronto 34:13 Conversations with VCs and Investors 35:57 Investing in Share vs. Physical Real Estate 39:51 Dealing with Hard Times and Personal Solace 39:58 Final Thoughts and Taking Action

Maxime Courchesne, a VC Investment Manager at Investissement Québec, discusses the thriving tech ecosystem in Montreal and Quebec. He highlights IQ's focus on investing in Quebec ventures with international potential and the challenges faced by local startups. Max shares insights on maintaining an edge as an investor, dealing with hard times, and the diverse VC ecosystem in Quebec.

Akash Vaswani is a General Partner at Velocity Fund. Velocity Fund is a pre-seed fund spun out of the University of Waterloo to invest in world-changing companies at the earliest stage. Waterloo grads have started companies like Databricks, Instacart, Faire, Substack, PagerDuty, Top Hat, ApplyBoard, D2L, Avidbots, BufferBox (acquired by Google), Kik, North (Formerly Thalmic Labs, Acquired by Google), Pebble (Acquired by Fitbit), Float, Vidyard and MUCH more. Takeaways What makes UWaterloo founders so strong, co-op, professors own their IP, success breeds success and more. Why the co-op program is so legendary and drives so much impact. What Velocity Incubator is and why Velocity Fund spun out. Why UWaterloo is the fourth largest feeder school to Y Combinator after Stanford, Berkley and MIT. Velocity companies have raised $4.2B with a net equity value of $26B. Where should founders build? Canada or the US? Chapters 00:00 Akash's Experience at the University of Waterloo and Introduction to Velocity 04:06 The Power of Velocity and University of Waterloo in Unlocking Entrepreneurial Opportunities 09:42 The Impact of the Co-op Program at the University of Waterloo 13:36 The Role of Velocity in Supporting Startups 18:05 Akash's Journey as a Founder and Investor 21:29 The Thesis and Approach of Alicorn Ventures 29:39 The US-Canada Debate and the Importance of Building in the Right Location 44:42 The Future of the University of Waterloo and Velocity 51:52 Connecting Canadian Entrepreneurs 52:15 Addressing Scarcity Mindset and Funding

Lewis Wynne-Jones is the VP Product at ThinkData Works. ThinkData Works unlocks the value of external data to grow your business. Connect seamlessly to any source, drive critical insights, and deliver data while retaining visibility and control. Flexible data connections, an intuitive catalogue interface, and a suite of enrichment tools securely deliver data where it needs to be — inside or outside your organization. Takeaways Being employee #1 at ThinkData. Understanding the goals and outcomes of using data is crucial for effective data management. The shift from a consulting model to a SaaS product requires careful planning and consideration of the market dynamics. How to think about data from a startup and large company perspective. Data tools and platforms play a significant role in the data management space, but it's important to remain agnostic and adaptable to different technologies. AI is a powerful tool for operationalizing data, but it's important to have a pragmatic view and focus on solving real problems. Building products that are designed for humans and telling a whole story with data are key to delivering value to customers. Chapters 00:00 The Genesis of Think Data 03:35 Being the First Employee 06:48 Personal Journey at Think Data 13:33 Shift from Consulting Model to SaaS Product 17:18 Shift from External Data to Internal Data 22:06 Impact of Tools and Platforms on Think Data 26:01 The Hype Cycle of AI 29:46 Thinking About Data for Founders and Large Companies 35:19 Making Decisions with Data 39:26 Building and Leading Product 43:47 Dealing with Hard Times 46:25 Data or Data? 48:32 Changing Metrics and Models in Venture Capital 49:32 The Rise of Bootstrapping 50:08 The Importance of Happy Paying Customers 50:52 Reflections and Appreciation

Amodini Chhabra is an Investor at Compass Digital Ventures. Compass Digital Ventures is the Corporate Venture Capital (CVC) arm of Compass Group. They invest in Seed and Series A startups at the intersection of food, retail, and hospitality technology. Their area of interest include frontline employee experience, automation, sustainability tech, restaurant management, convenience economy, omnichannel retail, AI & ML. Compass Group is one of the largest contract food service companies in the world employing over 500,000 people. Takeaways Transitioning from a design background to venture capital. CDV's unique Pilot, Invest, Scale process for working with early-stage companies. How to launch, build and create a successful CVC platform. Unique challenges for the food service industry. Challenges of CVC include balancing strategic objectives with financial returns and maintaining alignment with the parent company's goals. Why AI and fintech are interesting areas for Amo right now. Chapters 00:00 Transition from Design to Venture Capital 02:24 Experience at Boston Consulting Group Ventures 06:19 Joining Compass Digital Labs 09:13 Compass Digital Labs and Compass Digital Ventures 12:01 The Process of Working with Startups 14:28 Strategies for Corporate Venture Capital Success 17:55 Investment Stage and Co-Investment 20:50 Defining the Thesis and Focus Areas 23:45 Deal Flow and Finding Founders 27:36 Unique Challenges in the Food Service Space 31:11 Internal Relationships and Strategic Value 34:29 Incubating In-House Solutions 37:41 Areas of Interest: FinTech, AI, and Procurement 43:52 Favorite Books: 'The Inner Game of Tennis' and 'The Palace of Illusions' 45:45 Excitement for the Future: Driving Innovation and Finding Balance 47:03 Dealing with Hard Times: Mindfulness and Supportive Circle

Rachel Wong is the Co-Founder of Monday Girl. Monday Girl is the first private members club focused on supporting and connecting next-generation women leaders. Monday Girl offers: A powerful network of like-minded professionals who can offer guidance, support, and valuable connections Resources, programming, and mentorship opportunities that can help you grow and develop as a leader in your respective field Digital and IRL gatherings where members can build genuine connections that can last a lifetime Email concierge@mondaygirl.ca to learn more Follow Monday Girl on Instagram Takeaways Learnings from being one of the earliest Uber Eats Canada team members. The genesis story of Monday Girl, a community and mentorship platform for women, and the pain points it addresses. Going from a side hustle with Monday Girl to fulltime. Networking can be redefined to be more inclusive and less transactional. The importance of brand and redefining networking to make it more inclusive and less transactional. Insights on scaling the community, monetization through sponsorship and membership, and creating successful meetups. Chapters 00:00 Early Days at Uber Eats Canada 02:10 Genesis Story of Monday Girl 05:41 Building Community and Gathering Feedback 06:11 Scaling the Community 08:20 Brand and Networking 11:08 Different Mediums and Channels 16:05 Redefining Networking 20:01 Mentorship at Monday Girl 22:45 Transitioning to Full-Time 25:41 Scaling the Community 28:00 Monetization and Sponsorship 30:27 Creating Successful Meetups 33:09 Future Focus for Monday Girl 38:00 Favorite Book and Dealing with Hard Times 41:35 Excitement for the Year Ahead My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Alex McIsaac is the Founder and General Partner of Northside Ventures. Northside Ventures is a pre-seed and seed-stage venture capital firm backing exceptional Canadian founders in the US and Canada with unique insights derived from past experiences that serve as a competitive advantage in their next venture. They invest in a founder’s first round of external capital, often at the point of company inception and ideation. Their typical cheques are $100K-500K. They believe in a generalist approach to early-stage investing, prioritizing categories that can potentially transform our world's future greatly. Core investment categories include artificial intelligence, B2B SaaS, fintech and cleantech. Takeaways Operational experience is valuable for venture capitalists, as it provides credibility and a deeper understanding of the challenges faced by founders. Learnings from being a founder at NRStor (acquired by Blackstone) and an investor at BDC and Global Founders Capital. The best founders often have experience working at scaled ventures and have solved hard problems, giving them a competitive advantage in their next venture. How Alex defines an exceptional founder and what characteristics they have. Outbound sourcing and dealflow strategies Alex uses. Raising a first-time fund as an emerging manager and solo GP. Canadian founders are often more conservative and capital-efficient compared to their American counterparts, but the gap is narrowing as the ecosystem matures. Northside Ventures aims to back exceptional Canadian founders at the earliest stage and believes in the potential for Canada to produce more unicorns in the coming years. Chapters 00:00 Early Career Moves and Venture Capital 02:24 Founding NRStor and Building a Business 05:30 Transitioning from Venture Associate to Founder 08:07 Joining Global Founders Capital and Gaining Autonomy 10:05 The Importance of Founders in Investment Thesis 13:53 Evaluating Founders and Their Experience 16:57 Differences Between American and Canadian Founders 20:04 Genesis of Northside Ventures 22:20 Considerations for Fund Size and LPs 25:38 Value Add and Supporting Founders 29:39 Sourcing Deal Flow and Identifying Opportunities 36:00 Investments and the Future of Northside Ventures My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Cory Janssen is the Managing Director of AltaML Fund I LP and the Co-Founder and Co-CEO of AltaML. Previously, Cory co-founded Investopedia, a financial education site that provided content and tools to help educate individual investors. From its founding in 1999, Investopedia became one of the most popular financial sites on the web and was sold to Forbes Media in 2007. Cory is also a director at VerticalScope Inc., and sits on several private company advisory boards. Connect with Cory on LinkedIn. AltaML is a leading artificial intelligence (AI)-powered solutions developer. Working with organizations that want to use AI to leverage their data to develop solutions that drive tangible business results, AltaML empowers partners to create operational efficiency, reduce risks and generate new sources of revenue. Through a deep understanding of organizational pain points and challenges, AltaML’s solutions encompass the entire machine learning (ML) life cycle, from evaluating potential use cases and determining feasibility to piloting solutions, putting code into production, and ensuring model evolution. Takeaways Investopedia was founded accidentally during the dot-com bubble and became the web's biggest investor education website. Successful AI adoption requires understanding business workflows, data, and creating a program rather than individual projects. Large language models (LLMs) have the potential to revolutionize various industries and change how software is built. How Rich Sutton with reinforcement learning (UAlberta) and Geoff Hinton with deep learning (UToronto) created the underpinnings for the AI industry. Why Canada is not great at commercialization and how we can change that/adapt to it. Talent in the AI industry can come from various sources, and it's important to have a mix of domain expertise and technical skills. Canada needs to change its mindset and become a player in the AI industry to fully capitalize on its potential. Having a circle of people to lean on, such as peer-to-peer groups, is crucial for getting through hard times as an entrepreneur. Chapters 00:00 The Origin of Investopedia 02:22 The Acquisition by Forbes 06:07 Life After Investopedia 08:14 The Birth of AltML 11:50 The Venture Studio Model 23:49 Common Mistakes in AI Adoption 28:20 Focus on Large Language Models (LLMs) 33:30 Talent and Learning in the AI Industry 39:07 Keeping AI Talent in Canada 44:01 Capitalism and Entrepreneurship 44:41 Excitement for Clean Tech and Bursting of the AI Hype 45:31 Dealing with Hard Times 46:40 Reflections on Running the Podcast 49:40 The Importance of Asking for Help My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns! 

Steve Davis is the CEO of Operto. Operto is the world’s leading property automation and IoT operating system for vacation rentals, hotels, and serviced apartments is revolutionizing guest stays and hospitality management. Through technology that connects teams, guests, managers and smart devices; Operto addresses common friction points to provide fully seamless and personalized stays - creating greater efficiency, guest satisfaction and more revenue. Takeaways Marketing has evolved from a mass-market, spray-and-pray approach to a more targeted and consultative strategy, focusing on becoming a trusted advisor and thought leader. Successful salespeople now need to adapt to longer sales cycles and the fact that buyers are more informed than ever before, requiring a consultative and value-driven approach. Having experience as both an investor and founder can provide unique perspectives and insights that can make someone a better leader and decision-maker. Acquisitions can be a faster and more efficient way to grow a business, but it's important to carefully consider the integration process and cultural fit. Building a strong company culture is crucial for attracting and retaining top talent, and it requires creating an environment where people can do their best work and feel empowered. Operto solves the problem of managing short-term rentals by providing automation and tools that streamline operations and enhance the guest experience. Operto takes an open-source approach, working with various hardware and software platforms to provide flexibility and compatibility for their customers. Personal growth as a CEO can be achieved through continuous learning, seeking advice from mentors and peers, and taking time for self-reflection and self-care. Chapters 00:00 Evolution of Marketing 03:03 Consultative Sales Approach 05:37 Insights from Investor and Founder Roles 09:23 Joining Aperto as CEO 12:28 Problem Solved by Operto 17:51 Open Source Approach 19:42 Acquisitions vs. Building Internally 23:38 B2B and B2C Dynamics 26:53 Building a Strong Company Culture 30:42 Maintaining an Edge as a CEO 34:20 Favorite Books and Personal Growth 47:08 Excitement for 2024 48:43 Continuous Learning and Growth 50:45 Seeking Great People for Hyper Growth My podcast supporter! ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fasken's Emerging Tech and Venture Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada. Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns!