The Hard Part with Evan McCann

This episode explores how AI is transforming hiring practices, emphasizing real-time testing, new roles, and the importance of human intuition in recruitment. Guests Ali and Andrew share insights on leveraging AI for better matchmaking, feedback loops, and building effective, nimble teams.Alison is the Partner, Talent at Golden VenturesAndrew is the Founder of BoardyChapters00:00 Introduction and Focus on Broken Hiring Practices01:11 Traditional Success Metrics in Hiring Are Changing01:57 Real-Time Testing and Practical Skills Over Past Experience02:44 Shift from Filling Roles to Strategic Matchmaking03:55 New Roles Emerge: AI Adoption Experts and Prompt Engineers05:48 The Evolving Role of People Management in AI Era07:20 The Value of Curiosity and Openness to Change08:50 Technical Skills and Building with Latest Tools10:22 Accessing Talent Beyond Traditional Platforms12:02 Deep Conversations and Motivations in Hiring14:04 Using AI for Better Candidate Matchmaking17:01 The Power of Personal Connections and Fit17:23 Feedback Loops and Continuous Improvement in Hiring21:20 AI as a Central Team Member and Meeting Facilitator23:48 Scaling Talent Acquisition with AI and Data29:45 Building Long-Term Relationships and Trust with AI33:18 The Human Element in AI-Driven Conversations37:07 Future of Audio and Speech in AI Interactions42:44 Trust, Accountability, and Outcomes in AI Recruitment47:37 Balancing AI and Human Judgment in Hiring52:17 Personal Relationships and Work Dynamics54:13 Closing Remarks and Key Takeaways

Max Cunningham is the Founder and CEO of Sesh Products.Sesh Products provides modern nicotine alternatives that aim to support in reducing and controlling cravings.Chapters00:00 The Journey Begins: From Vaping to Sesh02:46 Cultural Insights: The Swedish Influence on Nicotine Products05:42 Navigating Regulations: Launching in Canada vs. the U.S.08:08 Market Dynamics: The Shift from Smoking to Pouches11:02 Branding and Positioning: Creating a Modern Nicotine Experience13:42 Investment Insights: Partnering with 8VC16:33 Consumer Feedback: Iterating in a Regulated Market19:10 The Rise of Pouches: Trends and Accessibility22:02 Health Perspectives: The Benefits of Nicotine Pouches24:18 Building Trust: Ethics and Responsibility in Marketing26:58 Future Outlook: Scaling and Global Expansion

Ian MacKinnon is the Co-Founder of Stingray Security.Real-time protection from online scams, phishing, and fake websites.Ian previously Co-Founded Later.comChapters00:00 The Evolution of AI-Driven Phishing03:57 Consumer and Corporate Perspectives on Phishing08:17 The Role of Technology in Phishing Attacks11:58 Identifying and Preventing Scams16:28 The Future of Phishing and AI Tools21:27 Building Trust in a Digital World27:03 Mobile Vulnerabilities and Phishing Risks29:37 Deepfakes and Voice Cloning in Phishing34:34 The Ongoing Battle Against Phishing

Robert Farlow is the Co-Founder and CEO of Plato.Training Environments for Browser AgentsChapters00:00 The Genesis of Browser Agents02:38 Building Universal Agents05:25 Training Models and Learning Mechanisms08:02 The Future of Browsers and Agents10:39 Trust and Error Management in Automation13:39 Synthetic Data and Edge Cases16:15 Complexity in Multi-Step Tasks18:53 Navigating the AI Landscape21:39 The Data Wars and Business Incentives24:07 The Evolution of User Interfaces26:36 Building in San Francisco28:57 The Role of AI in Team Dynamics31:45 Resilience in Entrepreneurship

Brent Lane is the CEO of BigGeo.BigGeo is transforming how the world works with geospatial data. With innovative technology and industry-leading speed, they empower organizations to visualize, interact with, and unlock the full potential of location-based insights—at any scale.Chapters00:00 Understanding Geospatial Data02:45 The Importance of Location-Based Context05:37 Infrastructure Challenges in Geospatial Data08:09 The Future of Spatial Analytics11:03 Monetization of Geospatial Data13:53 Building a Unified Data Platform16:42 The Role of AI in Geospatial Data19:29 Navigating Sovereign Data and Cloud Solutions22:14 Team Dynamics in a Tech-Driven World25:02 Finding Balance in Business and Life

Ignacio Tartavull is the CEO of Pinkbot.Pinkbot builds robots that make last-mile delivery faster, cheaper and greener.Chapters00:00 Intro1:45 From Education to Neuroscience: The Journey Begins02:33 The Shift to Autonomous Driving: A New Challenge05:34 Navigating City Regulations: The Toronto Experience08:13 Logistics of Robot Deliveries: How It Works10:46 Real-World Challenges: Interacting with the Environment13:51 Financial Aspects: Cost-Effectiveness of Delivery Robots16:31 Business Model: Partnering with Restaurants19:23 The Future of Autonomous Vehicles: A Long Road Ahead22:13 The Future of Delivery Platforms23:34 Weather Challenges in Delivery24:39 Enterprise Partnerships and Their Impact27:26 Insights from Being a Courier32:19 The Future of Delivery Beyond Food34:01 Regulatory Considerations for Delivery Robots35:38 Urban vs. Suburban Delivery Dynamics38:06 Building a Robotics Company40:26 Designing for the Future of Transportation41:20 Overcoming Challenges in Business

Ben Vinegar is the Co-Founder of Modem.Modem is your auto-triage Product Manager.Modem turns scattered feedback – from users, teammates, and software – into actionable, living issues. Save time, reduce bottlenecks, and ship faster.Chapters00:00 Intro1:45 The Future of Developer Tools05:35 The Changing Role of Software Engineers15:04 Open Source in the Age of AI19:02 Stickiness of Developer Tools20:34 The Evolution of Developer Tools27:58 Hiring in the Modern Tech Landscape31:24 The Toronto Tech Scene vs. San Francisco38:20 Resilience in Entrepreneurship

Justin Sky is the CEO and Co-Founder of Rose Rocket.Rose Rocket is a SaaS-based Transportation Management System (TMS) specializing in workflow automation for Enterprise and SMB transport companies.Chapters00:00 Intro1:40 Acquisitions and Strategic Fit02:18 Leveraging AI and LLMs in Business04:41 Replatforming for Future Growth07:44 The Surge of New Players in Transportation Tech10:58 Understanding the Transportation Industry13:42 The Future of Autonomous Trucks15:32 Industry Dynamics and Consolidation Trends17:59 Advice for Founders in Traditional Industries21:23 Hiring for Culture and Values24:39 The Evolution of Y Combinator27:14 Refilling the Founder’s Tank30:42 Navigating the Toronto Ecosystem33:02 Strategic Fundraising Insights35:03 Building a Diverse and Effective Board37:16 The Toronto Tech Scene: Growth and Challenges40:15 Lessons from the Journey of Entrepreneurship

Elan Lee is the CEO of Exploding Kittens.Chapters00:00 Intro1:40 Designing Engaging Games02:49 The Importance of Player Feedback05:28 Accessibility and Player Experience08:22 The Golden Age of Tabletop Games11:25 Kickstarter Success Strategies13:54 Building and Sustaining Community16:53 Quality Control in Physical Games19:25 Expansions and Game Evolution21:38 Retail Dynamics in Tabletop Games23:26 Balancing Creativity and Business26:13 Persistence in Game Development28:20 Team Structure and Internal Operations28:47 Understanding Customer Needs31:12 Designing for Social Interaction32:21 Innovation vs. Remakes in Gaming34:21 The Testing and Refinement Process37:19 Balancing Rigour with Timelines38:59 Recognizing Joy in Gameplay39:55 Coping with Hard Times

Ahmed Nimale is the Co-Founder and CEO of KYD Labs.Chapters00:00 Intro1:40 The Journey into Live Entertainment02:56 Understanding the Ticketing Landscape05:35 The Role of Venues and Ticketing Platforms08:20 Marketing Challenges in Live Events11:28 Financial Dynamics of Live Entertainment14:17 The Future of Ticket Pricing17:01 The Impact of Resale Markets20:13 The Role of AI and Technology in Live Events22:57 Direct Artist-Fan Relationships25:18 The Evolution of Music Financing28:24 The Future of Live Event Production31:17 The Intersection of Crypto and Live Events34:03 Artist Engagement and Fan Loyalty37:01 Navigating the Music Industry's Financial Landscape39:48 Finding Balance as a Founder