The Hard Part with Evan McCann

Cynthia Arscott is the Founder & CEO of Goldminds. Goldminds is a kids' meditation app that provides research-backed meditations, sleep stories and mindfulness classes. We teach kids how to productively manage stress, regulate emotions and sleep better. With lifelong mental health being formed in early childhood, our mission is simple - give kids the top tools to take care of their emotional & mental health while they are young, so they are set up for success emotionally as they grow up. Takeaways Cynthia's Uber experience and the Uber Toronto mafia. Becoming a founder and the desire to help children. Starting with in-person school programs and evolving into an app. Stories are a powerful tool for engaging children and aiding their development. Building a community and leveraging social media is crucial for marketing. Feedback loops are essential for improving the app experience. Voice and tone in storytelling significantly impact children's engagement. Pricing strategies. Future of Goldminds and AI integration. Chapters 00:00 The Uber Experience and Its Impact 02:52 Transitioning to Entrepreneurship 06:06 Building Goldminds: From School Programs to App 08:54 The Role of Stories in Child Development 12:02 Marketing Strategies and Community Building 15:08 Navigating Challenges and Feedback Loops 17:56 The Importance of Voice and Tone in Storytelling 21:05 Pricing Strategies and Customer Acquisition 24:05 Balancing Personal and Professional Life 27:12 The Future of Goldmine's and AI Integration Keywords Uber, entrepreneurship, Goldminds, mindfulness, children's stories, app development, marketing strategies, personal branding, parenting, AI in storytelling

Ruslan is a Co-Founder of Float. He started the business in 2020 while studying computer science at the University of Waterloo and Business at Wilfrid Laurier University. Previously he worked at Uber ATG as a perception engineer and Shopify as a data scientist. Float is complete business finance for Canadian companies. We offer modern financial services, powerful software and industry-leading support designed for every industry and stage of growth. Our integrated suite of products—including corporate cards, bill pay, expense management and high-yield accounts—gives finance teams everything needed to manage spending and cash flow efficiently, so they can keep pace with the demands of their business. To learn more, visit floatfinancial.com.  Takeaways Reflecting on the past 5+ years of the Float journey The importance of recognizing and appreciating moments in business. Witnessing compounding growth firsthand and why it is a significant factor in business success. Hiring top talent raises the overall standard within the company. Building a strong culture. The evolution of Float's product offering. Understanding customer pain points is key to product development. Discussing Float's customer segments from SMBs to enterprises. Float's increased demand and traction from larger customers. Ruslan's personal growth since starting the company out of school and how he has changed as a leader. Competition awareness should be balanced with customer focus. Thoughts on competition. Why focus on the Canadian market + opportunities + challenges that brings. Thoughts on raising. Streamlining ops for a better customer experience. The impact of product development is more important than the frequency of releases. Chapters 00:00 Reflecting on Five Years of Float 09:22 Building Culture and Hiring 15:16 Evolving Product Offerings 21:42 Understanding Customer Profiles and Market Positioning 29:34 Understanding Competition in the Financial Space 35:36 Thoughtful Approaches to Fundraising 42:43 Personal and Professional Growth Insights Keywords Float, entrepreneurship, product development, company culture, hiring, customer experience, growth, FinTech, SMB, market strategy, financial services, customer experience, competition, fundraising, strategic growth, product development, Canadian market, business innovation, team growth, self-reflection

Scott Langille is the Founder of V2. V2 supports ambitious people who are building the future in Vancouver. Takeaways Scott's upbringing in a small town shaped his entrepreneurial spirit. The role of ambition and how it is influenced. The crucial role that community plays in fostering innovation. Socratica and launching the node Atelier at UBC. Vancouver startup scenes's opportunities and challenges. Building connections between ambitious individuals and accomplished founders is key to success. Diversity in experiences (art, science, tech, etc.) leads to better startup ideas. Creating a culture of builders. V2 aims to create a hub for ambitious individuals. Inspiration can come from various disciplines, not just tech. Navigating exodus - The Brain Drain Dilemma. Chapters 00:00 Scott's Journey: From Small Town to Startup Founder 08:11 The Role of Ambition in Startup Culture 16:31 Building Community: The Power of Socratica and Atelier 20:45 Vancouver's Startup Ecosystem: Opportunities and Challenges 30:19 Navigating Exodus: The Brain Drain Dilemma 34:14 Creating a Culture of Builders: The V2 Vision 45:31 Inspiration and Future Aspirations Keywords Scott Langille, startup culture, ambition, community building, Vancouver, Socratica, Atelier, V2, entrepreneurship, innovation

Kyle Braatz is the Co-Founder and CEO of Fullscript. Fullscript believes in the power of whole-person care and is fully committed to helping all providers deliver it. They help create an ongoing cycle of whole-person care by giving providers a single platform that brings together industry-leading labs, clinically effective supplements, and an intuitive suite of tools to promote adherence and outcomes. We discussed... Kyle's early aspirations shaped his entrepreneurial journey. Building a culture of impact. The concept of "whole person care" The future of healthcare lies in whole-person medicine Sustaining growth over 10+ years Cultural fit over technical skills Aligning and refocusing the whole company and how to do that well Capital efficiency - Kyle breaks down the capital infusion history of the company Why Fullscript story is under-known Kyle and his wife's impact on the Ottawa community and business community Kyle shares a story about when Fullscript almost shutdown The importance of independent thinking as a founder Acquisitions + partnerships and doing them well Building a startup mindset inside a company that has 1000+ people and almost $1B in revenue Launching new products and business lines and how to treat them like startups within the business Chapters 00:00 Kyle's Journey: From Firefighter Aspirations to Entrepreneurship 05:13 Whole Person Care: Redefining Healthcare 10:16 Cultural Integrity: Scaling with Core Values 16:08 Capital Efficiency: Achieving Billion-Dollar Milestones 22:02 Continuous Growth: Learning and Adapting 27:33 Transforming Healthcare: The Future of Whole Person Medicine 34:24 The Importance of Focus: Building a Sustainable Business 40:18 Community Impact: The Role of Philanthropy in Business 46:03 Startup Mindset: Building and Innovating Within Established Businesses Keywords entrepreneurship, healthcare, Fullscript, whole person care, capital efficiency, company culture, growth, Ottawa, acquisitions, leadership, healthcare, whole person medicine, business growth, entrepreneurship, community support, focus, resilience, innovation, technology, philanthropy

Aswinkumar Rajendiran is the Co-Founder of Maple. Maple is an all-in-one revenue management platform that streamlines sales-led and product-led billing workflows and tracks holistic revenue metrics as quickly as deals are signed without weeks of reconciliation. Maple can be leveraged in no-code or low-code mode by enabling quick experimentation-ready basic, credits-based, usage-based or seat-based billing capabilities into your product with just a few lines of code. Takeaways Attending UWaterloo and working on side projects Getting into YC and building his first company Joining Rippling ($13.5B valuation) as the first employee Learnings from Parker Conrad and the unique way Rippling builds product The decision to move back to Canada and launch Maple Why billing is such a problem and headache for companies Billing processes have become increasingly complex in modern businesses Working closely with early customers Maple's product strategy and building a full stack solution for billing Founder-led sales, how to do them well and for how long Raising money Building the right team - focusing on great engineers Chapters 00:00 From Side Projects to Founding a Startup 05:56 Joining Rippling: The First Employee Experience 12:13 Building Maple: Insights from Rippling 18:12 Strategic Selling: Targeting the Right Customers 24:09 The Importance of Founder-Led Sales 30:00 Building the Right Team: Focus on Engineering 35:51 Raising Money: Aligning Vision and Funding Keywords startups, entrepreneurship, Y Combinator, Rippling, Maple, billing solutions, founder journey, product development, go-to-market strategy, team building

Callum Woznow is the Co-founder of Slate. Slate is building the next-generation mobile keyboard. Takeaways Working in different cultures (Singapore and Germany) provides unique insights into startup ecosystems. The keyboard is an underexplored product with massive potential. AI can revolutionize how we interact with keyboards and the purpose of keyboards. Consumer behaviour around keyboards. Lack of innovation in this space from T9 to BlackBerry Keyboards to the launch of the iPhone. Chat about SwiftKey acquired by Microsoft for $250M. Pivot from B2B to B2C. Nuances to different global markets. Monetization strategies differ significantly between iOS and Android. The focus on "prosumer". Why keyboard products need to be perfect from a UX standpoint. Obsession around design and product. Why are keyboards so interesting and available across all apps. Chapters 00:00 Global Perspectives: Insights from Europe and Asia 08:21 Revolutionizing the Keyboard: Innovation and Consumer Behavior 15:03 Navigating the B2B to B2C Pivot: Strategies and Insights 21:12 Building a Keyboard: Challenges and Market Dynamics 26:29 The Balance of Speed and Quality in Startups 31:32 Navigating Remote Work Challenges 38:57 Personal Growth and Professional Excitement Keywords startup, entrepreneurship, global experience, keyboard innovation, B2B, B2C, consumer behavior, technology, AI, market dynamics, keyboard design, user experience, startup challenges, remote work, investment strategies, user feedback, product development, quality assurance, team communication, personal growth

Paul Lee is the CEO & Co-Founder of Patlytics. Patlytics is a state-of-the-art patent intelligence platform powered by a generative AI engine. Their cutting-edge LLMs and advanced techniques are bespoke to intellectual property and drive 80% more efficiency for IP workflows including patent generation, claim charts, infringement detection, classification and more. Patlytics recently announced $4.5M in seed funding led by Gradient, Google's AI-focused venture fund, with participation from 8VC, Joe Montana’s Liquid 2 Ventures, Tribe Capital, Vermilion Ventures, Gaingels, Alumni Ventures, Position Ventures and several undisclosed angel investors including select partners from premier law firms and Datadog President Amit Agarwal. Takeaways Starting his career working at Peter Thiel's Mithril with Alex Kolicich (previous guest), Joe Lonsdale and JD Vance His founder experience and working at Google Working in VC at Global Founders Capital and Tribe Capital Starting Patlytics and why AI is transforming the legal tech landscape How Paul raised $4.5M without a deck Customer discovery process and building an understanding of a new market Understanding IP and patents AI's role in enhancing product value Co-Founder relationships Chapters 00:00 Paul Lee's Journey: From Silicon Valley to Founding Patlytics 09:54 The Shift in Legal Tech: Embracing AI and Innovation 14:54 Understanding Intellectual Property: Challenges and Opportunities 20:00 Building Trust: Assembling a Founding Team 25:01 Raising Capital: Focus on Business Over Decks 30:02 Customer Discovery: Learning from Conversations 35:09 AI's Role in Enhancing Product Value 39:45 Navigating Challenges: Reflections from a Venture-Backed Founder Keywords Paul Lee, Patlytics, venture capital, legal tech, AI, intellectual property, startup journey, customer discovery, founding team, fundraising

Lars Leckie, Managing Director of Aspenwood Ventures, shares his journey from founder to venture capitalist. He discusses the partnership model in venture capital and the critical importance of maintaining a consistent investment strategy. Lars highlights how AI presents new opportunities for enterprise software, while addressing the necessity of capital efficiency. He emphasizes the trend of earlier public offerings for startups and the vital role of empowering founders rather than micromanaging them, alongside effective sales strategies and revenue growth milestones.

Patrick Chung is the Managing General Partner of Xfund. Xfund is an early-stage venture capital firm built to back entrepreneurs who think laterally and experiment across disciplines. They are a pioneering partnership between some of the country’s most successful venture capital firms and some of the world’s best research universities in the United States and abroad. Patrick's bio is fascinating! Bachelor, JD and MBA from Harvard Masters from Oxford McKinsey Founder of ZEFER which hit $100M annual revenue and was acquired Partner at NEA Takeaways Patrick's journey from Harvard, Oxford, McKinsey and into venture. Learnings from being a VC at NEA. The genesis story behind Xfund and its focus. Why founders are like artists. Meeting Sam Altman 20 years ago and investing in his first company Loopt. Cultural shifts are encouraging more graduates to pursue entrepreneurship. University bias often leads to safe career choices and how to change that. Providing term sheets upon graduation provides real choices for potential founders. Talent over industry. The importance of co-founders. Navigating university policies on IP. Chapters 00:00 Patrick Chung's Journey: From Harvard to Venture Capital 03:06 The Empathy of Founders: Insights from the Investor Side 06:04 Identifying Great Founders: The Xfund Approach 08:53 Cultural Shifts in Entrepreneurship: A New Generation of Founders 12:06 Navigating University Bias: The Challenge of Safe Choices 15:11 Creating Real Choices: The Experiment Stake Initiative 18:07 Finding Talent: Where to Discover Future Founders 21:09 Sector Focus: Talent Over Industry 23:56 The Power of Co-Founders: Trust and Collaboration 27:07 Selecting Schools: The Power Law of Startup Success 30:05 Unlocking Entrepreneurial Potential: Tools and Strategies 32:47 Commercialization and IP: Navigating University Policies 36:07 Personal Insights: Dealing with Hard Times Keywords Patrick Chung, Xfund, venture capital, entrepreneurship, founders, university startups, empathy, investment, startup culture, commercialization

Saam Mashhad is the Co-Founder and Chief of Product & Legal Operations at EvenUp. EvenUp uses data and technology to help plaintiffs and attorneys achieve better legal outcomes. EvenUp recently announced a $135M Series D which brings their valuation to over $1B. The round was led by Bain Capital Ventures, with participation from Premji Invest, Lightspeed Venture Partners, Bessemer Venture Partners, SignalFire, and B Capital Group. Takeaways Saam's journey from commercial litigator to co-founding EvenUp. Why the focus on personal injury law. How EvenUp streamlines legal workflows. How to build a product that seamlessly integrates into lawyers' workflow. AI's impact on legal tech. Designing a product that has to be 100% accurate and when to loop in humans on EvenUp's side. Having an ops-heavy product. Balancing market needs with automation. Launching new products. User feedback. How the legal landscape is shifting with AI + tech. Chapters 00:00 From Lawyer to Entrepreneur: The Genesis of EvenUp 06:01 Innovating Legal Workflows: The Role of Technology 12:02 Building a Product Team: The Importance of Diverse Expertise 17:55 Expanding the Product Suite: New Offerings and Features 24:03 Navigating Challenges: Personal and Professional Growth 30:06 Looking Ahead: Future Opportunities and Personal Reflections Keywords EvenUp, personal injury law, legal technology, litigation funding, AI in law, product development, user experience, legal workflows, startup journey, entrepreneurship