The Hard Part with Evan McCann

Connor Turland is the Co-Founder and CEO of Ceedar.Ceedar is the last bookkeeper you'll need to hire. It's time to retire the old ways. With Ceedar, you get done-for-you bookkeeping, up-to-date financials and maximized tax deductions, all on a modern platform that integrates well.Takeaways- Early Founder Experiences- When Your Co-Founder is Also Your Spouse- Identifying Gaps in the Bookkeeping Space- The Aesthetics of Software: Beauty Meets Functionality- Integrations: Building a Seamless Experience- Targeting the Right Customer Base- Go-to-Market Strategies: Word of Mouth and Influencers- Leveraging AI for Efficiency- Raising Funds: The Seed Strapping Approach- Pricing Strategies in a Competitive MarketChapters00:00 The Genesis of Sprillow and Early Experiences05:02 Co-Founder Dynamics: Balancing Work and Marriage08:13 Identifying Gaps in the Bookkeeping Space12:06 The Aesthetics of Software: Beauty Meets Functionality13:54 Integrations: Building a Seamless Experience17:51 Targeting the Right Customer Base22:00 Go-to-Market Strategies: Word of Mouth and Influencers24:49 Leveraging AI for Efficiency30:07 Raising Funds: The Seed Strapping Approach31:52 Pricing Strategies in a Competitive Market41:57 Dealing with Hard Times: Grounding PracticesKeywordsSprillow, Ceedar, co-founder dynamics, bookkeeping, AI, software aesthetics, integrations, customer base, go-to-market strategies, pricing strategies

Kurtis McBride is the Co-Founder and CEO of Miovision.Miovision provides cities with modern tools to fix today's traffic problems. They offer solutions that collect multimodal traffic data and uncover actionable insights, helping municipalities get more out of their road network. The result: streets capable of moving more people – safely and efficiently – whether they are in a car, on a bus, on a bike or e-scooter, or walking.Takeaways- Founding Miovision Right Out of UWaterloo- Defining Smart Cities: The Role of Technology- Connected and Autonomous Vehicles and the Future of Transportation- Bridging the Gap: Transitioning to Digital Infrastructure- Challenges of Hardware in Infrastructure Technology- Navigating Large Customer Relationships- R&D and Government Support- The Role of Government in Innovation- Leadership Framework: The Captain, The Monk and The Mist- Shifting Mindsets: From Scarcity to AbundanceChapters00:00 Founding Miovision: The Genesis of Innovation02:00 Defining Smart Cities: The Role of Technology04:41 Connected Vehicles and the Future of Transportation08:41 Bridging the Gap: Transitioning to Digital Infrastructure12:41 Challenges of Hardware in Infrastructure Technology15:21 Navigating Large Customer Relationships19:08 R&D and Government Support: A Critical Discussion23:57 The Role of Government in Innovation29:34 Lessons from 20 Years of Entrepreneurship39:36 Shifting Mindsets: From Scarcity to Abundance43:29 Navigating Hard Times in BusinessKeywordsMiovision, smart cities, connected vehicles, digital infrastructure, transportation technology, hardware challenges, R&D, government support, innovation economy, urban planning, innovation, entrepreneurship, government policy, mindset shift, leadership, business growth, procurement strategy, technology, Canadian economy, resilience

Yegor Sak is the Founder of Windscribe.Windscribe is a leading internet security and privacy company.Their goal is to transform the internet with easy-to-use yet powerful tools, that allow anyone to circumvent censorship, access geographically restricted content, and minimize their exposure to marketers, criminals and surveillance dragnets.Takeaways- Understanding VPNs: Basics and Use Cases- The Global Perspective: VPNs in Authoritarian Regimes- Building a Robust VPN: Technical Challenges and Solutions- Regulatory Landscape: Navigating Laws and Compliance- Dynamic Pricing: Making VPNs Accessible Worldwide- Future Trends: The Evolving Role of VPNs in Privacy- BootstrappingChapters00:00 Understanding VPNs: Basics and Use Cases07:34 The Global Perspective: VPNs in Authoritarian Regimes11:39 Building a Robust VPN: Technical Challenges and Solutions19:01 Regulatory Landscape: Navigating Laws and Compliance22:17 Dynamic Pricing: Making VPNs Accessible Worldwide25:14 Future Trends: The Evolving Role of VPNs in Privacy27:46 Day-to-Day Operations: Running a VPN Company35:31 Overcoming Challenges: Resilience in BusinessKeywordsVPN, privacy, internet security, censorship, technology, online anonymity, regulatory challenges, dynamic pricing, global access, digital freedom

Frédérick Lavoie is the Co-Founder and President of Deck.Deck is the developer infrastructure to access user-permissioned data simply, and at scale. Takeaways- The Genesis of Flinks- Timing and Tailwinds in Business- Lessons from Flinks and the Transition to Deck- The Role of Technology in Modern Startups- The Drive to Start Again: Reflections on Success- Leadership Lessons from Past Experiences- Nuances in Infrastructure Businesses- Understanding Developer Needs- Building Documentation Before Features- Investor Dynamics for Second-Time Founders- The Dynamics of Co-Founder Relationships- Building in Montreal: Opportunities and Challenges- The Role of AI in Product DevelopmentChapters00:00 The Genesis of Flinks03:02 Navigating the FinTech Boom05:57 Timing and Tailwinds in Business09:06 Lessons from Flinks and the Transition to Deck11:54 The Role of Technology in Modern Startups15:08 The Drive to Start Again: Reflections on Success18:58 The Reality of Building Credibility21:58 Leadership Lessons from Past Experiences25:52 Adapting to New Market Dynamics28:07 Key Nuances in Infrastructure Business30:00 Understanding Developer Needs32:54 Building Documentation Before Features33:48 Investor Dynamics for Second-Time Founders37:14 Scaling Challenges and User-Centric Approaches38:52 Navigating Early Customer Conversations41:06 The Dynamics of Co-Founder Relationships45:47 Leadership Styles and Team Dynamics51:27 Building in Montreal: Opportunities and Challenges53:06 The Role of AI in Product Development55:04 Coping with the Ups and Downs of FoundingKeywordsFlinks, FinTech, startup journey, entrepreneurship, technology, business strategy, market timing, lessons learned, Deck, Canadian tech, entrepreneurship, leadership, business strategy, developer tools, investor relations, AI in business, team dynamics, discomfort in growth, infrastructure business, credibility in startups, scaling challenges, user-centric approaches, customer conversations, co-founder relationships, leadership styles, building in Montreal, AI in product development, founder challenges

Eliot Pence is the Founder and General Partner of Tofino Capital.Tofino Capital invests in frontier markets and frontier technologies. Eliot is also the Chief Business Officer of Osmo. Osmo is giving computers a sense of smell. Backed by Lux Capital, Google Ventures, and Two Sigma Ventures. Takeaways- The Evolution of Defense Tech Investing + Dynamism Funds- Anduril's Unique Approach- Why The US is in The Fourth Wave of Defense Tech Investment and Canada is in The First Wave.- Why Canada is Lagging Behind- International Market Strategies for Defense Tech- Investment Landscape in Canadian Defense Tech- The Future of Canadian Defense Spending- Tofino Capital and Frontier Markets- Navigating Government Procurement and Requirements in Defense Tech- Global Trends and Canada's Sovereign CapabilityChapters00:00 Eliot Pence's Journey in Defense Tech03:46 The Evolution of Defense Tech Investment08:55 Anduril's Unique Approach to Defense Tech12:50 International Market Strategies for Defense Tech16:22 Investment Landscape in Canadian Defense Tech19:55 The Future of Canadian Defense Spending23:35 Tofino Capital and Frontier Markets27:03 Navigating Requirements in Defense Tech30:49 Global Trends and Canada's Sovereign Capability39:25 Finding Balance in Hard TimesKeywordsdefense tech, investment, Canada, Anduril, Tofino Capital, international markets, sovereign capability, venture capital, frontier markets, technology innovation

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