The Hard Part with Evan McCann

Ben Rollert is the Co-Founder and CEO of Composer. Composer is an automated trading platform that allows you to build a portfolio of hedge fund-like strategies. Takeaways Ben's first founder experience with Intervaliq. Learnings from building Breather (raised $100M+). The importance of a solid business model cannot be overstated. Keeping a small team with Composer. Founder-led companies versus professional management. Understanding board dynamics. Doing market research to validate startup ideas. Using user feedback effectively. Why the team is based in Canada but can't operate here. The gap that Robinhood and Wealthsimple aren't focused on. Building products for prosumers. Building an AI product to empower users versus using AI for auto-trading. Chapters 00:00 Founding Experiences and Lessons Learned 09:03 The Breather Experience: Insights and Missteps 14:59 The Genesis of Composer: From Idea to Execution 25:06 Market Opportunities and Target Audience 32:00 Navigating Regulations and Business Models 39:04 Future Aspirations and the Role of AI Keywords founder experiences, Breather, Composer, market opportunities, regulations, business model, AI in trading, startup lessons, venture capital, trading software

Ori Eldarov is the Co-Founder & CEO of OffDeal. OffDeal is an AI-native investment bank for small businesses. They offer small business owners a hassle-free way to sell their company for the highest price to the best possible buyer. They leverage years of Wall Street experience and their custom-built proprietary AI technology to ensure your business attracts the highest number of buyers so that you can realize the full value of your life's work. OffDeal also offers buy-side services that assist buyers with proprietary deal origination (typically add-ons) and comprehensive market mapping/market research services to support due diligence or portfolio value creation. Takeaways His journey from i-banking at RBC to HBS to founding OffDeal. GenAI sparked Ori's interest in applying it to finance. His YC experience and learnings. Streamlining business transactions using technology. Marketplace challenges in SMB transactions. AI and human touch: The OffDeal Model. Building trust in a fragmented industry. Trends in SMB acquisitions: opportunities and challenges. Timing the market: when to sell a business. Scaling through founder-led sales. OPEX versus CAPEX. How OffDeal is focused on scale in a traditionally boutique space. Chapters 00:00 From Banking to Entrepreneurship: A Journey Begins 05:52 The Birth of OffDeal: Innovating Investment Banking 10:08 Marketplace Challenges in SMB Transactions 14:24 AI and Human Touch: The OffDeal Model 18:10 Building Trust in a Fragmented Industry 22:31 Trends in SMB Acquisitions: Opportunities and Challenges 27:58 Timing the Market: When to Sell a Business 30:37 Scaling Through Founder-Led Sales 33:12 Establishing Trust: The Key to Success 36:40 Creating Jobs and Delivering Value Keywords entrepreneurship, investment banking, OffDeal, AI, small business, marketplace, trust, M&A, trends, business sales

Asanka Jayasuriya is a Partner and CTO at 8VC. 8VC is a venture capital firm that invests in early-stage and growth-stage tech companies. It was co-founded in 2015 by Joe Lonsdale, who is also a co-founder of Palantir. The firm is headquartered in Austin. Takeaways Asanka's early days at UofT. The benefits of internships. Launching and building the Amazon Toronto office. The "Glass Ceiling" in Canadian tech Canada needs more successful tech companies to retain talent. Choosing and moving to Austin over SF or NYC. Meeting Joe Lonsdale while playing pickleball. Adapting to new trends in software development. Being a great engineering leader. How AI tools are impacting software development. How startups should structure their architecture early days, a focus on simplicity. Hiring early-stage SWEs and what to look for. Balancing speed versus quality early days. The true value of a 10x engineer lies in team amplification. How to hire a 10X engineer. How software purchasing criteria have evolved post-2021. Software perspective when building deeptech companies. Diving into 8VC's Build Program! AI tools will transform product development in the next decade. Chapters 00:00 Early Days at the U of T 05:32 Navigating the Glass Ceiling in Canadian Tech 11:11 Choosing Austin: A New Chapter 17:11 Adapting to New Trends in Software Development 22:42 Common Mistakes in Scaling Tech Teams 28:33 Evaluating Ideas and Milestones 34:03 Identifying Top Engineering Talent 40:09 The Future of AI Tools in Engineering Keywords career transition, software engineering, Amazon, Canadian tech, CTO, venture capital, hiring mistakes, tech leadership, AI in software, Austin tech scene, hiring process, venture studio, deep tech, engineering leadership, software purchasing, AI tools, mentorship, personal growth, CTO insights, investment strategies

Charlie Iscoe is the Co-Founder of CommonShares. CommonShares is a business succession platform that enables retiring owners to get fair value for their business while ensuring that their employees and communities are cared for. They facilitate fair and efficient exits for retiring owners, recruit, train and support succession leadership as required, and transition the business to employee ownership over time. They believe that business succession can be a win-win outcome for owners, workers, and communities. Takeaways Charlie transitioned from banking to entrepreneurship. Sunday Farms his first venture. Travelling around the world helped Charlie gain clarity on his entrepreneurial aspirations. CommonShares aims to address the succession planning crisis among small business owners. The "Silver Tsunami". Over 90% of small business owners lack a succession plan, creating a significant opportunity. Employee-owned companies tend to outperform their peers in various metrics. CommonShares' model. Financing and structuring deals. Post-acquisition support and operations. Common Shares is positioned to become the buyer of choice for businesses transitioning to employee ownership. Creating a "Win-Win-Win" model. Chapters 00:00 From Banking to Entrepreneurship 04:16 The Birth of Sunday Farms 10:22 Identifying the Silver Tsunami 18:17 CommonShares: A New Business Model 26:46 Financing and Structuring Deals 30:54 Post-Acquisition Support and Operations 39:00 Collaborations and Future Opportunities Keywords entrepreneurship, employee ownership, business succession, private equity, small business, investment, CommonShares, Sunday Farms, financial model, community impact

Landseer Enga, Co-founder of Revyl and former Uber innovator, dives into the transformative world of observability. He shares how Revyl emerged from a successful internal project at Uber, aiming to disrupt the market dominated by giants like DataDog and Splunk. Landseer emphasizes the crucial role of end-to-end testing in software quality and the strategic importance of lean teams in early-stage startups. He also discusses the evolving landscape of enterprise software with AI, and the advantages of in-person sales in a competitive tech environment.

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