The Hard Part with Evan McCann

The Friday Show Episode 4 with Xavier Hébert-Couturier, Noah Casarotto Dinning and William Johnson.6:00 - Xavier from Picketa21:00 - Noah from Arvo41:50 - William from Overstory

Kevin Callahan is the Co-Founder and CEO of Uniblock.Uniblock is a fully automated orchestration layer that combines 100s of APIs from 50+ partners into a single unified API.Takeaways- Learnings from Wattpad, Twitter/X and Coinbase- Building in the Crypto Space- Nuances of API Companies- Strategic Partnerships and Platform Decisions- Cultivating Company Culture- Companies Are Often Bought, Not Sold- Building Relationships with Corporate Development Teams- Fundraising Strategies and Processes- Comparing Tech Ecosystems: SF vs. Toronto- Giving Back: Mentorship and EducationChapters00:00 Early Career Insights03:39 Learning from Iconic Companies07:18 Transition to Entrepreneurship10:03 Building in the Crypto Space11:33 Nuances of API Companies13:05 Strategic Partnerships and Platform Decisions15:15 Cultivating Company Culture17:38 The Balance of Transparency20:57 Navigating Acquisition Offers26:32 Building Relationships for Corporate Development29:53 Fundraising Strategies and Processes34:14 Comparing Tech Ecosystems: San Francisco vs. Toronto41:05 Giving Back: Mentorship and Education44:20 Work Ethic and Startup Success46:01 Finding Your Passion in Entrepreneurship48:25 Living Like an Athlete: Resilience in BusinessKeywordsKevin Callahan, product management, entrepreneurship, API, crypto, partnerships, company culture, transparency, acquisition, startup, corporate development, fundraising, tech ecosystems, mentorship, work ethic, entrepreneurship, resilience, startup success, networking, Canadian tech

Farhan Thawar is a VP and Head of Engineering at Shopify.Takeaways- Why Xtreme Labs Was So Special- Why Xtreme Labs Did Almost Zero Interviews- The Role of AI in Engineering- Pair Programming and Collaboration- Story Behind Shopify Being One of The First Companies to Use GitHub Co-Pilot- Why Shopify Uses GitHub Co-Pilot and Cursor- Why Shopify Doesn't Use Jira or Linear- AI and Toil Reduction in Software Engineering- The Evolution of Prompting in Engineering- Why Tobi Has The Best Prompts- Vibe Coding- Shopify's Delete Code Club - Deleting 5M Lines of Code- Maintaining a Hacky Culture in a Large Organization- The Meaning of Elegance in EngineeringChapters00:00 The Genesis of Extreme Labs02:59 Building a Unique Company Culture06:10 Hiring and Retaining Talent08:53 Innovative Perks and Employee Engagement11:53 The Role of AI in Engineering14:50 Pair Programming and Collaboration18:04 Navigating Tools and Technologies21:00 The Future of Engineering with AI26:57 AI and Toil Reduction in Software Engineering29:48 The Evolution of Prompting in Engineering34:23 Shopify's Delete Code Club: A Culture of Efficiency38:08 Maintaining a Hacky Culture in a Large Organization46:39 The Meaning of Elegance in Engineering48:34 Finding Energy in Hard TimesKeywordsXtreme Labs, company culture, hiring, employee engagement, AI in engineering, pair programming, innovative perks, technology tools, Shopify, talent retention, AI, software engineering, toil reduction, prompting, Delete Code Club, hack culture, elegance, entrepreneurship, Shopify

Samuel Witherspoon is the Co-Founder and CEO of ANVIL.ANVIL is a Mission First organization. They work with defence, public safety, law enforcement, and national security organizations to accelerate mission-critical decision making with analytical tools, automations, and game-changing machine learning capabilities.Takeaways- The Genesis of Anvil: From LegalTech to DefenseTech- Navigating the Canadian Procurement Maze- Reforming Canadian Procurement- Capital Needs in DefenseTech- Mastering the Art of Bidding- Working in High Security Environments - Trends in DefenseTech: Data and AI- Simplifying Complexity in Defense Operations- The Importance of Sovereign Defense CapabilitiesChapters00:00 The Genesis of ANVIL: From Legal Tech to Defense05:40 Navigating the Procurement Maze11:32 Reforming Procurement: A Call to Action18:07 Capital Needs in Defense Tech21:59 Mastering the Art of Bidding25:54 Building a Secure Company Culture29:38 Trends in Defense Tech: Data and AI35:31 Simplifying Complexity in Defense Operations43:07 The Importance of Sovereign Defense Capabilities48:34 Finding Strength in Hard TimesKeywordsAnvil, defense tech, procurement, national security, Canada, innovation, startup, military technology, AI, data management

Simon Leroux is the Founder and CEO of Optionality.Optionality is the AI-powered co-pilot designed to help M&A advisors, corporate finance teams, consultants, accountants, and Private Equity investors discover, qualify, and close more deals — faster.Chapters- The Journey of a Repeat Founder- Understanding M&A from a Founder's Perspective- Value Creation: Beyond the Numbers- The Importance of Strategic Planning for Selling- The Role of Advisors in M&A Transactions- Leveraging AI to Enhance M&A Advisory- Shifting Mindsets in the M&A Landscape- Navigating Industry Hesitations with AI- Scaling Advisory Teams in a Changing Market- Leveraging AI for Deal Sourcing and Value Creation- Effective Customer Engagement and Feedback LoopsChapters00:00 The Journey of a Repeat Founder03:06 Understanding M&A from a Founder's Perspective06:03 Value Creation: Beyond the Numbers08:57 The Importance of Strategic Planning for Selling11:49 The Role of Advisors in M&A Transactions14:49 Leveraging AI to Enhance M&A Advisory17:54 Shifting Mindsets in the M&A Landscape27:29 Navigating Industry Hesitations with AI31:02 Scaling Advisory Teams in a Changing Market34:49 Leveraging AI for Deal Sourcing and Value Creation42:04 Effective Customer Engagement and Feedback Loops46:48 Personal Growth and Resilience in EntrepreneurshipKeywordsM&A, entrepreneurship, value creation, business strategy, AI in finance, repeat founders, advisory services, business exit, market trends, strategic planning, AI, advisory, M&A, scaling, customer engagement, value creation, private equity, technology, entrepreneurship, industry trends

Andrew Graham is the Co-Founder and CEO of Borrowell.Trusted by 1 in 10 Canadians, Borrowell provides over 3 million members with comprehensive credit monitoring and personalized insights. Their innovative services, including Credit Builder and rent reporting, help consumers build credit so they can unlock access to a wider range of financial products at more competitive rates.Takeaways- Understanding Credit Scores- Innovating Credit Access- Building Financial Products- Expanding Credit Opportunities- The Importance of Open Banking- Challenges for FinTech in Canada- Partnership Strategies- The Evolution of FinTech in Canada- Scaling Borrowell to Millions- Personalization in Financial Services- Lessons from a Decade of Leadership- Balancing Fun and Seriousness in FinTech- User Engagement StrategiesChapters00:00 The Genesis of Borrowell02:00 Understanding Credit Scores05:14 Innovating Credit Access07:11 Building Financial Products10:51 Expanding Credit Opportunities12:51 The Importance of Open Banking16:06 Challenges for FinTech in Canada19:17 Partnership Strategies22:12 Navigating Consumer Choices23:25 The Evolution of FinTech26:03 Scaling Borrowell29:03 Personalization in Financial Services31:14 Lessons from a Decade of Leadership33:48 Balancing Fun and Seriousness in FinTech37:36 User Engagement Strategies39:14 Coping with Challenges as a FounderKeywordsBorrowell, FinTech, credit scores, open banking, financial products, consumer finance, scaling, partnerships, innovation, leadership

Mike Silagadze is the Founder and CEO of EtherFi.EtherFi is a decentralized non-custodial ETH staking protocol. It is the only staking protocol that allows stakers to retain control of their keys while delegating validator operations to node operators.Takeaways- Building and Exiting Top Hat- Why EdTech is a Challenging Space to Build- From Hedge Fund to EtherFi as a Platform- Understanding Staking and Restaking in Crypto- Simplifying Staking: The EtherFi Solution- Infrastructure Challenges: Navigating TradFi and DeFi- User Experience in DeFi- Global Reach: The Impact of a Borderless Approach- 30% of Latin Americans Have Used Stablecoins- Choosing the Right Jurisdiction for Crypto Businesses- Building Amidst Market Volatility- Insights on Fundraising and Investor Relationships- Future Predictions for DeFi and Mass Adoption- The Impact of DeFi on Traditional Finance- Government Involvement in Crypto: A Double-Edged SwordChapters00:00 Building Top Hat: Lessons from the Journey04:30 Transition to Crypto: The Spark of Interest07:57 From Hedge Fund to EtherFi: The Evolution10:23 Understanding Staking and Restaking in Crypto16:04 Simplifying Staking: The EtherFi Solution17:39 The Future of DeFi: Bridging TradFi and DeFi20:38 Infrastructure Challenges: Navigating TradFi and DeFi22:13 User Experience in DeFi: A New Approach25:42 Global Reach: The Impact of a Borderless Approach26:38 Navigating Global Compliance and User Engagement27:25 The Rise of DeFi in Latin America29:11 Choosing the Right Jurisdiction for Crypto Businesses30:16 Building Amidst Market Volatility32:15 Adoption Trends in Finance: TradFi, FinTech, and DeFi34:30 Insights on Fundraising and Investor Relationships38:32 Motivation Behind Long-Term Business Building40:25 Future Predictions for DeFi and Mass Adoption42:43 The Impact of DeFi on Traditional Finance46:11 Government Involvement in Crypto: A Double-Edged Sword47:57 Overcoming Challenges in EntrepreneurshipKeywordsTop Hat, education technology, crypto, EtherFi, staking, DeFi, TradFi, user experience, financial services, global finance, DeFi, cryptocurrency, compliance, Latin America, fundraising, market volatility, adoption, traditional finance, government involvement, entrepreneurship

Roger Kirkness is the Founder and CEO of Convictional.Convictional is the infrastructure that powers decisions at the world's most ambitious companies. Takeaways- The Value of Y Combinator Programs- Modern Dropship Acquisition and Company Pivot- Ask The Question: What Happens if it Works?- Tobi's AI Memo- AI in the Workplace: Opportunities and Challenges- CEOs Using ChatGPT and Claude to Make Decisions- Bias in Companies- Navigating AI's Future in Organizations- Leadership in the Age of AI- Cross-Functional AI Adoption in Companies- The Impact of AI on Company Structures- Choosing to Build in Waterloo- Remote Work: Strategies for Success- Dogfooding Your Own ProductChapters00:00 The Value of Y Combinator Programs04:12 Founding the Company: Genesis and Growth08:59 Navigating Acquisitions and Market Challenges11:41 Business Operations and Knowledge Management16:14 AI in the Workplace: Opportunities and Challenges21:08 Decision-Making in Startups and Beyond25:59 Navigating AI's Future in Organizations28:19 The Role of Essays in Shaping AI Perspectives30:40 Leadership in the Age of AI33:29 Cross-Functional AI Adoption in Companies37:47 The Impact of AI on Company Structures41:06 Remote Work: Strategies for Success45:14 Dogfooding: Using Your Own Product47:00 Resilience in EntrepreneurshipKeywordsY Combinator, startup programs, business operations, AI in workplace, decision making, entrepreneurship, knowledge management, acquisitions, B2B e-commerce, Convictional, AI, leadership, organizational change, remote work, cross-functional collaboration, dogfooding, entrepreneurship, company structure, management philosophy, technology adoption

Yoseph West is the Co-Founder and CEO of Relay.Relay is the business banking and money management platform that puts small businesses in complete control of their cash flow.To check out open roles at Relay, visit relayfi.com/careers.Takewaways- Why It Takes 10 Years to Build Anything Meaningful - Targeting the US Market- Understanding SMB Needs- Always Be Willing To Jump On a Plane- Why All New Hires Spend Two Weeks on CS- Monetization Strategies- Gathering Customer Feedback- "Minimal Loveable Product"- Why 40% of Customers Log In Daily- Navigating Regulatory Challenges- The Future of Fintech- Cultivating Company CultureChapters00:00 Yoseph's Entrepreneurial Journey02:56 Acquisitions and Learning Experiences06:11 The Genesis of Relay08:50 Targeting the U.S. Market12:00 Understanding SMB Needs15:12 Customer Service Insights17:46 Customer Journey and Onboarding21:08 Monetization Strategies24:00 Gathering Customer Feedback25:25 The Loneliness of Entrepreneurship30:00 Building a Financial Partnership34:59 Navigating Regulatory Challenges40:05 The Future of Fintech45:03 Cultivating Company Culture49:03 Personal Growth and ResilienceKeywordsentrepreneurship, acquisitions, Relay, SMB banking, customer service, monetization, U.S. market, financial technology, startup journey, customer feedback, entrepreneurship, financial partnership, fintech, company culture, regulatory challenges, personal growth, small business, coaching, digital banking, future of finance

Matt Loszak is the Co-Founder and CEO of Aalo Atomics.Aalo builds mass-manufactured nuclear plants that will power anything from a data center to a city. Their mission is to achieve 3¢ / kWh electricity. Their first product will be the Aalo Pod, a 50 MWe power plant purpose-built for data centers. They have raised $35M so far.Chapters- Matt's Founder Journey and Early Interest in Nuclear- Building Humi- How Humi and Ada's Founding are Intertwined- The Convergence of Nuclear and AI- Evolution of Nuclear Technology- Future Energy Demands and Business Models- The Focus on Data Centers- Assembling the Right Team for Nuclear- Understanding Customer Needs and Nuclear Economics- The Future of Decentralized Energy Solutions- Raising Capital for NuclearChapters00:00 Foundations of Innovation: Matt's Journey03:48 Building Humi: Lessons from the Startup World08:29 The Convergence of Nuclear and AI14:10 Evolution of Nuclear Technology18:45 Future Energy Demands and Business Models24:15 Assembling the Right Team for Nuclear Innovation28:19 Understanding Customer Needs and Nuclear Economics35:13 The Future of Decentralized Energy Solutions46:50 Raising Capital for Nuclear Innovations51:21 Navigating Challenges in EntrepreneurshipKeywordsnuclear energy, AI, startups, entrepreneurship, technology, innovation, clean energy, data centers, modular reactors, business strategy, nuclear energy, customer needs, decentralized energy, fundraising, nuclear economics, data centers, energy solutions, entrepreneurship, clean energy, reactor technology