The Hard Part with Evan McCann

Farhan Thawar, VP and Head of Engineering at Shopify, shares insights from his journey through Xtreme Labs and the unique culture that thrived there. He discusses Shopify's innovative use of AI, including their pioneering adoption of GitHub Co-Pilot and the transformative 'Delete Code Club' aimed at reducing code for efficiency. Farhan emphasizes the importance of elegance in engineering, fostering collaboration, and maintaining a hacky culture in a large organization, showcasing a vibrant approach to navigating the tech landscape.

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

Oban MacTavish is the Co-Founder and CEO of Spade.Spade is the only transaction data enrichment solution backed by real data. They leverage their vast first-party data network to bring instant clarity and context to every purchase and payment—with precisely matched merchant, category, and geolocation details that empower you to build the next generation of financial technology.Chapters- Oban's First Founder Experience with Hubly- Understanding Merchant Intelligence and Data Quality- Fraud Detection and Prevention Strategies- The Role of Rewards and Consumer Trust- Fintech Tailwinds and Market Opportunities- Building in an Ambiguous Data Landscape- AI's Impact on Fintech and Data Quality- The Value of Data in Modern Business- Understanding Customer Needs and Sales Strategies- The Y Combinator Experience and Early Customer Engagement- Insights on Fundraising and Investor Relationships- Building a Lean Team and Remote Work Dynamics- Navigating the US Market as a Canadian Startup- Identifying Your Strengths and Delegating EffectivelyChapters00:00 The Genesis of Hubly and Founding Experiences02:48 Transitioning to Spade: Lessons Learned06:05 Understanding Merchant Intelligence and Data Quality08:53 Fraud Detection and Prevention Strategies11:57 The Role of Rewards and Consumer Trust15:06 Fintech Tailwinds and Market Opportunities17:56 Building in an Ambiguous Data Landscape20:56 AI's Impact on Fintech and Data Quality24:27 The Value of Data in Modern Business26:22 Understanding Customer Needs and Sales Strategies30:38 The Y Combinator Experience and Early Customer Engagement32:38 Insights on Fundraising and Investor Relationships36:10 Building a Lean Team and Remote Work Dynamics38:36 Navigating the US Market as a Canadian Startup40:57 Identifying Your Strengths and Delegating Effectively44:58 Making Critical Decisions and Self-Care47:55 Coping with Challenges and Seeking SupportKeywordsSpade, fintech, data quality, fraud detection, merchant intelligence, rewards, consumer trust, AI, startup experience, data value, customer engagement, sales strategies, Y Combinator, fundraising, lean teams, remote work, Canadian startups, decision making, self-care

Rob Fraser, Founder and CEO of Outway, dives into the evolution of his sock company and the transformative challenges faced over two years. He shares insights on the balance of personal growth with business resilience and strategic decision-making, particularly in channel expansion. Fraser discusses the exciting impact of AI on consumer goods and the growing Canadian product movement. He also emphasizes the crucial role of innovative sock design in building customer loyalty and the importance of navigating opportunities with agility.