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 Ventures Andrew is the Founder of Boardy Chapters 00:00 Introduction...

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. Chapters 00:00 The Journey Begins: From Vaping to Sesh 02:46 Cultural Insights: The Swedish Influence on Nicotine Products 05:42 Navigating Regulations: Launching in Canada vs. the U.S. 08:08 Market Dynamics: The Shift from Smoking t...

Ian MacKinnon is the Co-Founder of Stingray Security . Real-time protection from online scams, phishing, and fake websites. Ian previously Co-Founded Later.com Chapters 00:00 The Evolution of AI-Driven Phishing 03:57 Consumer and Corporate Perspectives on Phishing 08:17 The Role of Technology in Phishing Attacks 11:58 Identifying and Preventing Scams 16:28 The Future of Phishing and AI Tools 21:27...

Robert Farlow is the Co-Founder and CEO of Plato . Training Environments for Browser Agents Chapters 00:00 The Genesis of Browser Agents 02:38 Building Universal Agents 05:25 Training Models and Learning Mechanisms 08:02 The Future of Browsers and Agents 10:39 Trust and Error Management in Automation 13:39 Synthetic Data and Edge Cases 16:15 Complexity in Multi-Step Tasks 18:53 Navigating the AI L...

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. Chapters 00:00 Understanding Geospatial Data 02:45 The Importance of Location-Based Context 05:37 Infrastructure Challe...

Ignacio Tartavull is the CEO of Pinkbot . Pinkbot builds robots that make last-mile delivery faster, cheaper and greener. Chapters 00:00 Intro 1:45 From Education to Neuroscience: The Journey Begins 02:33 The Shift to Autonomous Driving: A New Challenge 05:34 Navigating City Regulations: The Toronto Experience 08:13 Logistics of Robot Deliveries: How It Works 10:46 Real-World Challenges: Interacti...

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. Chapters 00:00 Intro 1:45 The Future of Developer Tools 05:35 The Changing Role of Software Engineers 15:04 Open Source in the Age of AI 19:02 Stickiness of Develope...

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. Chapters 00:00 Intro 1:40 Acquisitions and Strategic Fit 02:18 Leveraging AI and LLMs in Business 04:41 Replatforming for Future Growth 07:44 The Surge of New Players in Transportation Tech 10:58 Und...

Elan Lee is the CEO of Exploding Kittens . Chapters 00:00 Intro 1:40 Designing Engaging Games 02:49 The Importance of Player Feedback 05:28 Accessibility and Player Experience 08:22 The Golden Age of Tabletop Games 11:25 Kickstarter Success Strategies 13:54 Building and Sustaining Community 16:53 Quality Control in Physical Games 19:25 Expansions and Game Evolution 21:38 Retail Dynamics in Tableto...

Ahmed Nimale is the Co-Founder and CEO of KYD Labs . Chapters 00:00 Intro 1:40 The Journey into Live Entertainment 02:56 Understanding the Ticketing Landscape 05:35 The Role of Venues and Ticketing Platforms 08:20 Marketing Challenges in Live Events 11:28 Financial Dynamics of Live Entertainment 14:17 The Future of Ticket Pricing 17:01 The Impact of Resale Markets 20:13 The Role of AI and Technolo...

Doug Roseborough spent his career at multiple leading technology companies including 30 plus years at Oracle. Chapters 00:00 Intro 1:40 Early Days at Oracle 02:56 Oracle's Secret Sauce 05:16 Transition to the Bay Area 08:15 Rolling Out Pricing Models 10:31 Cultural Insights at Oracle 13:05 Leadership and Team Dynamics 15:35 Operations at Oracle 17:59 Effective Meetings 20:38 Customer Engagemen...

Tamer Shahin and Jerry Chen are the Co-Founders of Hiro . Hiro improves child health by turning physiotherapy into fun, interactive, movement-based games designed for kids of all abilities. Chapters 00:00 Intro 1:40 Inspiration Behind Hero 02:55 Understanding Therapy for Children with Disabilities 06:19 Gamifying Physiotherapy: The Solution 08:25 Accessibility and Convenience in Physiotherapy 11:3...

Cameron Conn is the CEO of Champlain . Cameron previously Co-Founded OneComply (acquired by GeoComply). Chapters 00:00 Intro 1:40 Cameron's Journey Through Industries 07:51 Transitioning to Retail and Learning the Ropes 12:14 Positioning and Pricing Strategies in Apparel 19:11 Navigating Wholesale and Direct-to-Consumer Channels 26:25 Navigating Industry Challenges 27:36 The Vancouver Apparel...

Robert Saunders is the Co-Founder and CEO of Ownright . Ownright simplifies real estate transactions with the perfect combination of expert legal guidance, a client-first approach, and efficient technology. Chapters 00:00 Intro 1:40 The Genesis of Ownright 07:14 Navigating Regulatory Challenges 13:14 Financial Hurdles in Real Estate Transactions 17:28 Growth Strategies and Market Expansion 20:50 U...

Brennan Spellacy is the Co-Founder and CEO of Patch . Patch combines technology and carbon markets expertise to help companies build and execute their carbon credit strategies from end to end, channelling capital into critical climate solutions. Chapters 0:00 Intro 1:40 The Evolution of Sonder: From Flatbook to Hospitality Innovator 06:41 Transitioning to Patch: The Journey to Founding a Climate S...

Francois Lafortune is the Co-Founder and CEO of Diagram Ventures . Francois is also a Managing Partner at Sagard and Chairman of the Board at Nesto . Diagram is a venture launchpad building the next generation of global companies based in Canada. They develop and incubate our own ideas, and find exceptional entrepreneurs and technologists to build companies with us. Chapters 00:00 Introduction 2:0...

Rishard Rameez is the Co-Founder and CEO of Zown . Zown is a buyer-first real estate platform operating in both Canada and the U.S., built to reward and empower people to reach their homeownership dreams faster. Through their model, buyers receive up to $25,000 toward their home purchase — funded through the commission Zown earns. There’s no repayment, and buyers keep full ownership from day one....

Michael Serbinis is the Founder and CEO of League . Founded in 2014, League is the leading healthcare consumer experience platform, reaching more than 40 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve heal...

Nicholas Chepesiuk is the VP of Innovation at Qualifacts . Nicholas was the Founder & CEO of OnCall Health, which was acquired by Qualifacts in 2022. Chapters 00:00 Podcast Introduction 2:00 Foundational Experiences in Early Roles 07:21 Telehealth Surge: Impact of the Pandemic 12:53 Post-Acquisition Insights and Growth Strategies 18:06 Trends and Opportunities in Healthcare 23:19 Building a St...

Derrick Emsley is the Co-Founder of tentree and veritree . Chapters 00:00 Podcast Introduction 2:00 The Genesis of Tentree 05:04 Lessons Learned in Entrepreneurship 07:36 Transitioning to Veritree 09:07 Navigating the Climate Tech Landscape 12:07 Project Selection and Impact 14:52 Building Partnerships and Verification 17:37 The Importance of Trees 20:24 Consumer Behavior and Local Impact 23:12 Tr...

Chloe Liang is the Co-Founder of Cocasa . Cocasa is revolutionizing travel and property ownership by allowing members to buy equity in luxurious holiday homes from €39,000/10% share. Chapters 00:00 Podcast Introduction 2:00 From Banking to Founding: Chloe's Journey 10:31 Identifying the Problem: Cocasa's Mission 21:08 Understanding the Cocasa Model 35:25 Navigating Challenges as a Founder...

Kyle Norton is the Chief Revenue Officer at Owner . Chapters 0:00 Podcast Intro 2:00 Evaluating Companies: The Key Factors 07:38 Building a Revenue Team: Initial Steps and Strategies 11:39 Quality Over Quantity: The Importance of Revenue Quality 15:49 AI in Sales: Internal and External Impacts 20:42 Navigating the Changing Landscape of Outbound Sales 26:58 Hiring for Success: Qualities in Sales Ro...

Benjamin Bergen is the President at Council of Canadian Innovators (CCI) . CCI is a member-based organization reshaping how governments across Canada think about innovation policy and supporting homegrown scale-ups to drive prosperity. Chapters 00:00 Podcast Introduction 2:45 Reflecting on a Decade of CCI's Impact 05:32 Understanding the Shifts in Innovation Policy 08:10 The Importance of Effe...

Nicole LeBlanc is a Partner at Woven Capital . Woven Capital is the $800M investment arm of Toyota Motor Corporation. Their aim is to broaden the group’s global reach and accelerate innovation by investing in exceptional growth-stage ventures. Chapters 00:00 Podcast Introduction 2:45 Introduction to Woven Capital 05:38 Investment Strategy and Structure 08:13 Exciting Technologies and Market Trends...

Anthony Azrak and Jai Mansukhani are the Co-Founders of OpenSesame . OpenSesame is building Cell, an embedded AI agent layer that lets users explore, understand, and take action inside any SaaS product using natural language. Chapters 0:00 Introduction 2:45 Introduction to Speedrun and OpenSesame's Experience 05:30 Identifying the AI Gap and OpenSesame's Focus 08:20 Customer Use Cases and...