The Hard Part with Evan McCann

David Gaylord is the Co-Founder and CEO of Bushbalm. Takeaways Growing up in a family business and jumping into e-commerce early Working at Shopify and learnings there Genesis story behind Bushbalm Going full-time with Bushbalm after a few years and over $4M in revenue Why salons/professional channel has been so powerful for the brand Advantages of wholesale from distribution and beyond Effectively using 3PLs How to do retail partnerships well Doing great product launches Limited Edition products Product launches around seasonal demand Black Friday strategies Bootstrapping Cash flow dynamics and how to use them as an advantage Chapters 00:00 The Evolution of a Family Business 05:20 The Birth of Bushbalm 10:44 Navigating Distribution Channels 16:16 Wholesale vs. Direct-to-Consumer 22:30 Leveraging Social Media for Growth 29:45 Timing and Strategy for Seasonal Product Launches 36:05 Cash Flow Management: Lessons from Gymshark 41:30 Looking Ahead: Goals for the Upcoming Year Keywords e-commerce, Shopify, Bushbomb, product-market fit, family business, direct-to-consumer, retail, distribution channels, trade shows, 3PL, retail partnerships, product launches, Black Friday strategies, pricing strategies, bootstrapping, cash flow management, supplier relationships, company culture, business growth, consumer engagement

Mike Gozzo is the Chief Product and Technology Officer (CPTO) at Ada. Mike is also an Operating Advisor at Bessemer Venture Partners. Previously Mike founded Smooch.io which Zendesk acquired. He then worked as SVP of Product at Zendesk. Takeaways Smooch.io was born from a unique incubation experience. The story behind the acquisition by Zendesk for $80M. Cultural alignment was a key factor in choosing Zendesk. Why he left his role at Zendesk to join Ada. After joining Ada why he cut the number of products and narrowed the company's focus. AI is reshaping product development and customer interactions. Flexibility in software design. The importance of delivering high-quality automated resolutions. Product teams should be structured around key metrics. How Ada structures their product and technical teams. Inference and intelligence in AI will become commoditized. Early-stage founders should focus on customer feedback. His work with Bessemer, angel investing and advice for founders. Chapters 00:00 The Genesis of Smooch.io 12:45 Navigating the Acquisition by Zendesk 13:01 Cultural Integration and Reflections Post-Acquisition 18:02 The Decision to Leave Zendesk for Ada 20:27 Impactful Decisions at Ada 22:58 AI's Influence on Product Development 25:45 The Evolution of AI in Customer Service 30:14 Building Effective Product Teams 36:27 The Future of AI Applications 39:49 Insights from Venture Capital and Angel Investing 42:13 Advice for Early-Stage Founders 44:41 Personal Growth and Professional Excitement 47:02 Navigating Challenges as a Founder Keywords Smooch.io, Zendesk, acquisition, startup culture, product management, AI, customer experience, entrepreneurship, Canadian startups, innovation, AI, customer service, product management, venture capital, early-stage startups, founder advice, machine learning, automated resolutions, product teams, investment strategies

Gregory Macdonald is the Founder and CEO of Bathorium. Bathorium was founded on the concept of benefits based on bathing; bath soaks that invigorate, restore and rejuvenate the end user. From day one this Canadian company's mandate is to create a truly memorable bath experience focusing on the bathers' well-being. Takeaways Bathorium was inspired by a transformative bath experience in Italy The company started in local markets Sourcing quality ingredients A feature on Good Morning America propelled their growth Channels, DTC, wholesale and more Thinking behind product offerings Pricing strategies and positioning The importance of brand Buying out his co-founder The second decade of the brand Chapters 00:00 The Genesis of Bathorium 05:01 Sourcing Ingredients and Building a Supply Chain 10:14 Pivotal Moments in Bathorium's Journey 15:26 Navigating Channels and Market Strategies 22:07 The Impact of Pricing and Brand Positioning 28:06 Looking Ahead: The Second Decade of Bathorium 34:38 The Role of Mentorship in Business Keywords Bathorium, entrepreneurship, clean beauty, wellness, product sourcing, market strategy, co-founder dynamics, brand positioning, mentorship, retail partnerships

Xavier Hébert-Couturier is the CEO and Co-Founder of Picketa Systems. Picketa Systems offers real-time plant tissue sampling for growers and agri-businesses to conduct nutrient analyses rapidly and independently. An online platform informs farmers instantly of nutrient deficiencies, enables agronomists to tailor nutrient critical levels and delivers a comprehensive overview of crop needs at the glimpse of a dashboard" Takeaways Genesis story of Picketa How the business model has evolved How real-time nutrient analysis is a gamechanger Building their prototype How Picketa fits into a farmer's typical process Creating a seamless user experience Grassroots marketing and getting in front of farmers The focus on agronomists as their super users Hardware + software integration and how to make it a great product Selecting what crops to focus on early on Industry trends show consolidation and a focus on precision agriculture Platform integrations Chapters 00:00 The Genesis of Picketa Systems 06:27 Business Model Evolution 11:52 Adapting Technology for Diverse Environments 17:23 Hardware and Software Integration 23:23 Navigating Industry Trends 33:06 Ecosystem and Platform Integration Keywords Picketa Systems, agriculture technology, crop analysis, tissue sampling, agronomy, business model, user experience, data utilization, marketing strategies, hardware integration

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