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 and Focus on Broken Hiring Practices

01:11 Traditional Success Metrics in Hiring Are Changing

01:57 Real-Time Testing and Practical Skills Over Past Experience

02:44 Shift from Filling Roles to Strategic Matchmaking

03:55 New Roles Emerge: AI Adoption Experts and Prompt Engineers

05:48 The Evolving Role of People Management in AI Era

07:20 The Value of Curiosity and Openness to Change

08:50 Technical Skills and Building with Latest Tools

10:22 Accessing Talent Beyond Traditional Platforms

12:02 Deep Conversations and Motivations in Hiring

14:04 Using AI for Better Candidate Matchmaking

17:01 The Power of Personal Connections and Fit

17:23 Feedback Loops and Continuous Improvement in Hiring

21:20 AI as a Central Team Member and Meeting Facilitator

23:48 Scaling Talent Acquisition with AI and Data

29:45 Building Long-Term Relationships and Trust with AI

33:18 The Human Element in AI-Driven Conversations

37:07 Future of Audio and Speech in AI Interactions

42:44 Trust, Accountability, and Outcomes in AI Recruitment

47:37 Balancing AI and Human Judgment in Hiring

52:17 Personal Relationships and Work Dynamics

54:13 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.

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 to Pouches

11:02 Branding and Positioning: Creating a Modern Nicotine Experience

13:42 Investment Insights: Partnering with 8VC

16:33 Consumer Feedback: Iterating in a Regulated Market

19:10 The Rise of Pouches: Trends and Accessibility

22:02 Health Perspectives: The Benefits of Nicotine Pouches

24:18 Building Trust: Ethics and Responsibility in Marketing

26:58 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.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 Building Trust in a Digital World

27:03 Mobile Vulnerabilities and Phishing Risks

29:37 Deepfakes and Voice Cloning in Phishing

34:34 The Ongoing Battle Against Phishing

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 Landscape

21:39 The Data Wars and Business Incentives

24:07 The Evolution of User Interfaces

26:36 Building in San Francisco

28:57 The Role of AI in Team Dynamics

31:45 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.

Chapters

00:00 Understanding Geospatial Data

02:45 The Importance of Location-Based Context

05:37 Infrastructure Challenges in Geospatial Data

08:09 The Future of Spatial Analytics

11:03 Monetization of Geospatial Data

13:53 Building a Unified Data Platform

16:42 The Role of AI in Geospatial Data

19:29 Navigating Sovereign Data and Cloud Solutions

22:14 Team Dynamics in a Tech-Driven World

25:02 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.

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: Interacting with the Environment

13:51 Financial Aspects: Cost-Effectiveness of Delivery Robots

16:31 Business Model: Partnering with Restaurants

19:23 The Future of Autonomous Vehicles: A Long Road Ahead

22:13 The Future of Delivery Platforms

23:34 Weather Challenges in Delivery

24:39 Enterprise Partnerships and Their Impact

27:26 Insights from Being a Courier

32:19 The Future of Delivery Beyond Food

34:01 Regulatory Considerations for Delivery Robots

35:38 Urban vs. Suburban Delivery Dynamics

38:06 Building a Robotics Company

40:26 Designing for the Future of Transportation

41:20 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.

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 Developer Tools

20:34 The Evolution of Developer Tools

27:58 Hiring in the Modern Tech Landscape

31:24 The Toronto Tech Scene vs. San Francisco

38:20 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.

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 Understanding the Transportation Industry

13:42 The Future of Autonomous Trucks

15:32 Industry Dynamics and Consolidation Trends

17:59 Advice for Founders in Traditional Industries

21:23 Hiring for Culture and Values

24:39 The Evolution of Y Combinator

27:14 Refilling the Founder’s Tank

30:42 Navigating the Toronto Ecosystem

33:02 Strategic Fundraising Insights

35:03 Building a Diverse and Effective Board

37:16 The Toronto Tech Scene: Growth and Challenges

40:15 Lessons from the Journey of Entrepreneurship

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 Tabletop Games

23:26 Balancing Creativity and Business

26:13 Persistence in Game Development

28:20 Team Structure and Internal Operations

28:47 Understanding Customer Needs

31:12 Designing for Social Interaction

32:21 Innovation vs. Remakes in Gaming

34:21 The Testing and Refinement Process

37:19 Balancing Rigour with Timelines

38:59 Recognizing Joy in Gameplay

39:55 Coping with Hard Times

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 Technology in Live Events

22:57 Direct Artist-Fan Relationships

25:18 The Evolution of Music Financing

28:24 The Future of Live Event Production

31:17 The Intersection of Crypto and Live Events

34:03 Artist Engagement and Fan Loyalty

37:01 Navigating the Music Industry's Financial Landscape

39:48 Finding Balance as a Founder