The Hard Part with Evan McCann

Paige Cey is the Co-Founder and Co-CEO of Benny. Benny is a new take on energy drinks. Takeaways The idea for Benny emerged from a shared love for adaptogens. The adaptogen trend and tailwind. Where the name Benny came from. The brand targets a millennial and Gen Z audience. In-person events. Building community for Benny. Social media strategy. Wholesale distribution. Flavor decisions. Relationships with co-packers. US expansion plans. Co-founder relationships. Thoughts on pricing. Hints at future products. Chapters 00:00 The Genesis of Benny: A Startup Journey 02:54 Crafting the Product: From Idea to Reality 06:11 Branding and Community: Building Friends with Benny 09:06 Navigating Production: The Co-Packer Experience 12:06 Marketing Strategies: In-Person Events and Community Engagement 15:11 Wholesale vs. E-Commerce: Balancing Distribution Channels 18:10 Flavor Decisions: Crafting Unique Taste Experiences 20:46 Customer Relationships: Engaging with Benny Drinkers 24:19 Innovative Beverage Launch and Consumer Engagement 26:46 Understanding Adaptogens and Their Benefits 30:04 Social Media Strategy and Community Building 32:12 The Importance of Authenticity in Brand Storytelling 36:09 Plans for U.S. Expansion 39:16 Co-Founder Dynamics and Relationship Building 41:42 Personal and Professional Growth 44:07 Mindset and Resilience in Entrepreneurship Keywords Benny, startup, adaptogens, yerba mate, branding, community, e-commerce, wholesale, flavors, marketing, Beverage industry, energy drinks, pricing strategy, adaptogens, retail strategy, social media marketing, community building, U.S. expansion, funding, co-founder relationships, entrepreneurship

Yuri Sagalov, Managing Partner of Wayfinder Ventures, shares his journey from Russia to the U.S. and how it shaped his entrepreneurial spirit. He discusses the evolution of Y Combinator and the glamour of being a founder compared to an investor. Yuri reflects on his angel investing successes and highlights 'velocity' as a crucial predictor of startup success. He also explains Wayfinder's unique approach to supporting founders and the growing accessibility of angel investing, revealing his contrarian views in the venture capital landscape.

Gennady Pekhimenko is the CEO and Co-Founder of CentML. Gennady is also an Associate Professor at the University of Toronto and a Faculty Member at Vector Institute. Takeaways Genesis of CentML - from academia to industry Commercializing university research Tailwinds behind AI and market opportunities Three Pillars of AI - models, data and hardware Enterprise adoption of AI - trends and insights The future of AI models - commoditization vs. innovation Raising $30M+ from Gradient Ventures, Radical Ventures, Deloitte Ventures, Nvidia, Thomson Reuters Ventures and more Attracting talent - competitive AI job market The UofT AI talent pool with Geoff Hinton, Raquel Urtasun, Aidan Gomez and many more What the federal government should do with the $2.4B in AI funding Why compute in Canada is critical to our AI success The role of Vector Institute Personal growth as a CEO and constantly learning Chapters 00:00 The Genesis of CentML: A Journey Through Academia and Industry 04:31 Commercializing University Research: The Builder Mindset 07:47 The Tailwinds of AI: Market Opportunities and Challenges 11:01 Three Pillars of AI: Models, Data, and Hardware 15:19 Enterprise Adoption of AI: Trends and Insights 18:37 The Future of AI Models: Commoditization vs. Innovation 21:46 Building a Flexible and Scalable AI Business 25:35 Attracting Talent: Competing in the AI Job Market 29:06 The Power of Networking: The Toronto AI Ecosystem 32:11 Government Initiatives: Building AI Infrastructure in Canada 37:42 AI Adoption in Enterprises: A Gradual Shift 40:57 Personal Growth: The Journey of a Startup CEO Keywords CentML, AI, machine learning, commercialization, university research, enterprise adoption, AI infrastructure, talent acquisition, Toronto AI ecosystem, government initiatives

In this chat, Olivia Steedman, Executive Managing Director of Teachers' Venture Growth, shares her journey from civil engineering to shaping late-stage venture investments in tech. She discusses the pivotal role of AI in sectors like fintech and health tech, highlighting emerging trends. Olivia explains the importance of a global investment strategy and the collaboration within her diverse team across key markets. Her insights on investment criteria and recent deals offer a fascinating look at building better businesses for the future.

Brook Papau is the Co-Founder and CEO of Orennia. Orennia is your all-in-one platform for accurate data, predictive analytics and actionable insights across the energy transition. Make more efficient capital-allocation decisions and maximize returns across the solar, wind, storage, power, RNG, CCUS, clean fuels and hydrogen sectors. The technology that powers Orennia’s platform delivers an unparalleled experience, distilling information into actionable insights to give you a competitive edge. Takeaways The evolution of RS Energy as a business and exiting for $1B Lessons from a decade at RS Energy Orennia genesis story The $2.5 trillion opportunity with renewables Ground truths in renewables which can be a polarizing subject Regional dynamics for energy (ie. wind versus solar) Orennia's AI strategy Building a strong culture Product differentiation and building a new category Dive deep into sales and thoughts on product Raising capital Chapters 00:00 The RS Energy Journey 03:25 Lessons from a Decade at RS Energy 08:13 Successful Business Model Shifts 11:16 Genesis of a New Venture 16:05 The $2.5 Trillion Renewable Opportunity 19:31 Ground Truths in Renewables 22:37 Regional Dynamics of Energy Sources 25:29 Product Differentiation in Energy Data 27:40 Leveraging AI for Data Solutions 30:30 Navigating Capital Raising Challenges 33:18 Sales and Product Integration 35:01 Building a Collaborative Culture 39:00 Personal and Professional Excitements 40:12 Coping with Challenges as a Founder Keywords RS Energy, energy transition, technology company, renewable energy, capital raising, AI in energy, business model shift, Calgary tech ecosystem, data analytics, founder mindset

Neil Grunberg is the Co-Founder and Managing Partner of Storytime Capital. Storytime Capital is a VC focused on early-stage (Pre-Seed & Seed) investments. They primarily focus on technology solving the Future of Work. Previously Neil was a Co-Founder at AlayaCare (~$300M raised) and was at Workbrain and part of the "Workbrain Mafia". Takeaways What made Workbrain so special and Neil's experience there. Genesis story of AlayaCare. What made AlayaCare's culture so strong and leading with empathy. Building and maintaining Co-Founder relationships. Fundraising insights (AlayaCare raised close to $300M) Checking your ego and Neil's experience working on product, strategy, corp dev, etc. How a founder's role changes throughout the life of a company. How to build a strong corp dev function. Why start a VC firm and what it is like having perspective as an operator, founder and now investor. Why the future of work thesis. Major shift in software solutions. Chapters 00:00 The Workbrain Experience 06:20 The Genesis of AlayaCare 10:39 Co-Founder Relationships and Empathy 14:33 Fundraising Insights 17:06 Evolving Roles in Startups 23:38 Corporate Development Lessons 29:23 Building a Community as an Investor 34:27 Future of Work Thesis 38:21 The Shift in Software Solutions 41:03 The Investor's Perspective 45:29 Personal and Professional Excitement 48:09 Handling Hard Times Keywords Workbrain, AlayaCare, co-founder relationships, fundraising, corporate development, future of work, software solutions, investor insights, community building, resilience

Jung Lee is the Head of Corporate Innovation Studio at Pioneer Square Labs. Jung's career has taken her across: Launching digital and mobile payments at Visa Launching Alexa Canada at Amazon Head of Partner Strategic Initiatives at AWSGlobal Head of Partnerships & Strategy at Wing. Wing is an Alphabet company focused on autonomous drone delivery We discussed Navigating the move from Canada to the US Lessons from Amazon and Alphabet - structure and innovation Launching new technologies in existing companies Business Development - keys to success AI in corporates - understanding and application. Working with corporates as a startup. Framework for idea validation. Finding the right corporate partners as a venture studio. Chapters 00:00 Navigating the Move: From Canada to the US 02:28 The Canadian Mindset: Risk-Taking and Exploration 04:49 Lessons from Amazon: Structure and Innovation 10:07 Launching New Technologies: The Wing Experience 14:15 Business Development: Keys to Success 19:15 Joining Pioneer Square Labs: A New Chapter 24:03 AI in Corporates: Understanding and Application 28:29 Models of Engagement: Working with Corporates 32:59 Framework for Idea Validation: A Unique Approach 36:31 Finding the Right Corporate Partners 40:55 Challenges in Venture Studios: What Goes Wrong? Keywords Canada, US, startups, business development, Amazon, AI, venture studios, corporate partnerships, innovation, entrepreneurship

Vincent Xue is the Co-Founder of Ivey Venture Capital Club and has done internships at Headline, Contrary, Global Founders Capital, Front Row Ventures, Portage and Julian Capital. Takeaways Why the early interest in VC compared to other classmates. How he landed his initial internships at top funds and tactics he used. His thoughts on networking and being scrappy. Creating the Ivy Venture Capital Club and making VC more accessible on campus. The importance of developing a personal brand through writing. He views venture as a young person's game, leveraging energy and enthusiasm. Building genuine relationships. Learning venture hands-on is critical fo success. Building community. The concept of "Talent Vortexes" Chapters 00:00 The Spark of Interest in Venture Capital 03:11 Navigating Early Career Opportunities 08:55 Building a Venture Capital Community 14:40 The Path to Venture Capital 20:45 Understanding the People Aspect of Venture 26:15 The Art of Writing in Venture 32:24 Curating Talent Vortexes 35:33 Personal Growth and Reflection Keywords venture capital, internships, networking, writing, talent, community, education, startups, personal development, early career

Christal Wang is the Co-Founder and CEO of Shimmer. Shimmer ADHD Coaching is the #1 coaching service for adults with ADHD, made for and by people with ADHD. You meet with an expert ADHD coach each week to set goals, learn skills, upgrade your routines, and stay accountable to real, sustainable change. Takeaways Chris's consulting background and foundational skills. Shimmer originated from her MBA and MPH at Berkeley and her dropping out! Going through YC. Pivoting in YC and learnings. Her ADHD diagnosis led to a new focus for Shimmer. The focus on ADHD coaching. Coaching complements medication, addressing skills and goals. Vetting coaches and the expanding market. Regulatory hurdles and navigating that. Building in SF. How she found her co-founder and built that relationship. Chapters 00:00 The Genesis of Shimmer 03:39 Navigating Pivots and Challenges 06:51 Understanding ADHD and Its Impact 09:24 The Coaching Landscape for ADHD 13:04 Vetting Coaches: Ensuring Quality 16:46 Sales Strategies and Market Dynamics 19:32 The Future of ADHD Coaching 21:40 Market Size and Neurodiversity 23:05 Measuring Success at Shimmer 24:20 Team Composition and Culture Building 25:33 Navigating Partnerships and Sales Channels 26:40 Regulatory Landscape for Coaching 28:31 Fundraising Insights and Strategies 31:05 Building a Network in the US 33:32 Co-Founder Dynamics and Relationships 36:01 Personal Growth and Learning 38:46 Coping with Challenges and Hard Times Keywords Shimmer, ADHD, coaching, mental health, entrepreneurship, pivots, fundraising, neurodiversity, consulting, healthcare

Lindy Drope, a Founding GTM team member at Lindy, shares her journey from Canada to San Francisco, including her experience navigating the O-1 visa process. She discusses the evolution of go-to-market strategies, emphasizing the shift from traditional methods to leveraging platforms like TikTok and Twitter. Lindy highlights how AI agents can dramatically enhance productivity and scalability for professionals. Her insights on balancing creativity with data-driven decisions offer a fresh perspective on modern tech challenges.