The Hard Part with Evan McCann

• 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

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 Engagement Strategies

23:00 Startup Advice

25:37 Navigating a Noisy Market

28:11 Bay Area Mentality

30:31 Career Reflections and AI Impact

33:06 Dealing with Hard Times

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

11:39 Leveraging Technology for Progress Tracking

14:02 Feedback from Parents and Therapists

14:47 Pricing and Accessibility Considerations

15:58 Market Size and Potential

17:39 Product Development and Iteration

22:25 Engaging with Families for Feedback

26:14 Addressing Therapist Shortages

27:31 Government Partnerships and Support

28:06 Overcoming Challenges as Founders

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 Scene

29:53 Understanding Manufacturing Relationships

33:00 Designing Collections with Purpose

35:22 The Value of Collaborations

39:42 Complexity in Apparel Collections

43:55 The Investment Landscape in Apparel

48:30 Overcoming Hard Times

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 Understanding Pricing and Unit Economics

24:38 Leveraging AI for Efficiency

32:11 The Future of PropTech

37:23 The Rebranding Journey

41:36 Finding Balance in Entrepreneurship

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 Solution

11:07 Understanding Carbon Markets: The Role of Patch in Sustainability

16:09 Navigating Complexity: Strategies for Chief Sustainability Officers

20:43 Crafting Effective Sustainability Strategies: Insights from Patch

24:21 Strategic Procurement in Carbon Credits

27:49 Navigating Global Projects and Technology Risks

31:28 Understanding the Global Carbon Market Landscape

35:14 Pricing Dynamics and Industry-Specific Strategies

38:58 Future Trends in Carbon Markets and Technology

43:40 Resilience in Entrepreneurship

45:44 Engagement and Community Building

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

2:00 The Genesis of Diagram: A Venture Studio's Origin

05:23 Navigating the Idea Flow: From Concept to Execution

09:49 Criteria for Success: Understanding the Venture Creation Funnel

13:54 Leveraging Competitive Advantage: The Diagram Ecosystem

16:36 Finding the Right Founders: The CEO Search Process

21:14 Funding Dynamics: Balancing Ownership and Attracting Investors

24:37 Team Structure: Blending Operators and Investors

27:18 Navigating the Entrepreneurial Landscape

28:51 Identifying Market Opportunities

31:05 Learning from Experience

36:51 Signals of Success

39:35 Emerging Trends Beyond AI

41:04 Balancing Ideas and Execution

44:15 Transitioning from Hands-On to Hands-Off

46:41 Coping with Challenges in Entrepreneurship

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.

Chapters

00:00 Podcast Introduction

2:00 The Spark of Innovation: A Reddit Post

04:43 Identifying the Gaps in Real Estate Services

11:16 Transforming Home Buying: The Financial Impact

13:23 Overcoming Traditional Barriers in Real Estate

14:46 Expanding Horizons: Geographic Growth and Market Dynamics

16:25 Understanding the Real Estate Commission Structure

20:30 Leveraging Technology for Scalability

23:12 Marketing Strategies in a Noisy Market

25:51 Navigating Market Dynamics and Economic Factors

30:23 Finding Purpose in Hard Times

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 health outcomes.

League has raised $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.

Chapters

00:00 Podcast Introduction

2:00 Getting Shit Done: The Core Philosophy

07:02 Healthcare Challenges: Access and Understanding

13:20 The Agentic Era: AI in Healthcare

19:30 Learning and Adapting: The Key to Success

22:23 Partnerships: Transforming Healthcare Together

26:18 League's Platform Approach: A New Era in Healthcare

31:49 Balancing Family and Business: A Personal Journey

36:18 Perseverance in Hard Times: Lessons Learned

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 Strong Company Culture

28:21 Personal Resilience and Coping Mechanisms

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 Trends in Sustainability

25:52 Metrics and ROI in Sustainability

28:38 Learning and Growth as a Founder

31:26 Team Dynamics and Culture

34:09 The Role of Impact in Business

37:01 Technology in Tracking Projects

39:52 Overcoming Challenges in Entrepreneurship

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

40:06 Engagement and Community Building

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 Roles

33:15 The Hybrid Work Debate: In-Person vs Remote

38:47 Geographic Strategy: Where to Position Sales Reps

44:09 Continuous Learning: The Benefits of Advisory Roles

47:20 Resilience in Sales: Maintaining Drive Through Challenges

52:31 Introduction to the Hard Part Podcast

52:31 Engagement and Community Building

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 Effective Government Policies

11:16 Building Stronger Industry-Government Relationships

13:37 Navigating National Sovereignty in a Global Economy

16:44 The Role of Government Procurement in Innovation

25:10 Navigating Government Contracts and Policy Advocacy

29:23 Capital Investment and Government's Role

32:24 Tax Competitiveness and Brain Drain

34:25 CCI's Mandate to Innovate

36:02 Navigating Federal and Provincial Regulations

38:29 Intellectual Property in the Innovation Economy

42:08 Engagement Between Government and Industry

44:07 Finding Purpose in Challenging Times

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

11:18 Post-Investment Support and Value Addition

14:16 Global Investment Focus and Cultural Insights

16:53 Diverse Applications of Toyota's Expertise

19:44 Robotics and Future Trends

22:38 Corporate Venture Capital Landscape in Canada

25:16 Learning as an Investor

28:07 Fund Structure and Investment Strategy

31:08 Cultural Differences in Business Practices

33:42 Deep Tech and Hardware Investments

36:27 AI Applications and Industry Trends

39:23 Resilience and Optimism in Challenging Times

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 Product Iteration

11:08 Target Market and Software Company Dynamics

13:58 The Future of AI Interaction and User Experience

16:49 Navigating the AI Landscape and Customer Education

19:33 Feature Development and Revenue Opportunities

22:34 Customer Discovery and Feedback Mechanisms

25:05 The Future of Work with Natural Language Interfaces

28:30 Raising Capital and the SF Ecosystem

32:25 The Language User Interface Revolution

37:21 Team Dynamics and Hiring in the AI Era

40:37 The Advantages of Being in Silicon Valley

42:49 Navigating Challenges as a Founder

Derek Bullen is the Founder and Board Director of S.i. Systems.

S.i. Systems is one of the largest Canadian IT staffing and consulting firms that connects organizations with skilled technology professionals.

They specialize in providing contract, permanent, and project-based talent across areas like software development, business analysis, project management, and IT infrastructure.

Chapters

0:00 Introduction

2:45 Founding Principles and Evolution of SI Systems

11:02 Shifts in the Contractor Landscape

13:29 The Art of Matching Talent with Opportunity

18:10 Scaling the Business: Lessons Learned

25:28 Building Relationships and Client Trust

29:02 Leadership Transition and Executive Roles

33:22 Personal Growth and Life After Leadership

39:54 Navigating Hard Times and Resilience

Emily Luk is a member of the Product team at Wealthsimple.

She previously Co-Founded Plenty, which was acquired by Wealthsimple.

Chapters

00:00 Emily's Journey: From Venture, Stripe and Even.

05:44 Cultural Insights from Stripe and Even

08:27 The Birth of Plenty: Identifying Gaps in FinTech

11:17 Navigating FinTech Challenges and Infrastructure

14:17 Unlocking Multi-User Experiences in FinTech

17:11 The Evolution of Consumer FinTech

19:56 Wealthsimple Acquisition: A Seamless Transition

23:01 Building a Comprehensive Product Suite at Wealthsimple

26:00 The Importance of Multi-User Financial Management

28:35 Growth Through Multi-User Engagement

31:41 Resilience in the Face of Challenges

Matthew Lombardi co-founded The Icebreaker with Jeff Waite and Michael Edwards.

The Icebreaker is Canada's defence innovation network, trusted by founders and funders, operators and professionals at DND and the CAF, defence primes, IDEaS, NATO DIANA, and everywhere decisions are made to defend the nation.

Their mission: to make Canada a net exporter of defence technology by 2030.

The Icebreak Links

• The Icebreaker Hackathon on September 20.
• Hundreds of Canadian companies making ‘dual use’ products useful for defence, survey finds - The Globe and Mail

Chapters

00:00 The Genesis of The Icebreaker and Canadian Defence Tech

05:35 Urgency for Change in Defence Strategy

08:09 Cultural Shifts in Defence Innovation

10:54 The Role of Technology in Defence and Civilian Life

13:32 Building a Community in Defence Tech

16:27 Spotlighting Canadian Innovators

19:09 Infrastructure Needs for Defence Innovation

21:52 Procurement and the Future of Defence

24:28 The Arctic: A New Frontier for National Security

27:25 National Pride and the Defence Tech Movement

30:12 Opportunities for New Talent in Defence Tech

Carter Li is the CEO of SWTCH.

SWTCH - https://swtchenergy.com/

Chapters

00:00 Genesis of SWTCH: A Personal Journey

05:35 Challenges of EV Charging in Existing Infrastructure

08:06 Designing Charging Solutions Based on Dwell Time

11:05 Technological Advances in EV Charging

13:49 The Value of EV Infrastructure in Real Estate

16:33 Shifts in the EV Charging Landscape

19:32 Vertical Integration in Charging Solutions

22:27 Innovative Solutions for Grid Overload

25:29 Monetization Strategies in Charging Infrastructure

27:15 The Future of Urban Living and EV Charging

29:55 Scaling Hardware in EV Charging

32:57 The Impact of Autonomous Vehicles on Charging

35:44 Finding Balance in the Entrepreneurial Journey

Simon Hørup Eskildsen is the Co-Founder and CEO of turbopuffer.

turbopuffer is a fast search engine that combines vector and full-text search using object storage, making all your data easily searchable.

Chapters

00:00 Introduction to turbopuffer

06:46 Revolutionizing Search with TurboPuffer

11:45 Technical Innovations Behind TurboPuffer

15:55 Caching Mechanisms and Performance

19:27 Scaling Challenges and Solutions

23:09 Navigating Industry Shifts and Market Dynamics

30:08 Sales Strategies and Founder-Led Growth

35:43 Pricing Models and Customer Relationships

41:25 Staying in Canada vs. Moving to the US

44:59 Coping with Challenges in Entrepreneurship

Stewart Lyons is the CEO of Bird.

Bird is on a mission to provide eco-friendly transportation for everyone.

Chapters

00:00 Stewart Lyons: A Journey Through Entrepreneurship

05:29 Navigating Regulatory Challenges in Canada

08:04 Turning Around Bird Global: Strategies and Insights

11:07 Operating a Global Business from Canada

13:15 Building Trust with Regulators and City Partners

15:52 Operational Complexity: Making Bird Profitable

18:37 Innovations in Scooter Technology

21:11 Seasonal Operations: Adapting to Market Conditions

24:17 Seasonal Workforce and Scalability

25:10 Exploring Diverse Transportation Modes

27:02 Franchising and Business Replication

29:53 Safety Measures in Micro-Mobility

33:46 User Experience and Software Integration

35:24 Subscription Model for Repeat Users

37:25 Micro-Mobility as Last Mile Solution

39:18 Insights on Acquisitions

40:54 Balancing Growth and Profitability

43:24 Motivation and Resilience in Business

Christian Weedbrook is the Founder and CEO of Xanadu.

Xanadu is a Canadian quantum technology company and one of the world's leading photonic quantum hardware providers.

Chapters

00:00 Understanding Quantum Computing

05:51 Infrastructure and Capital Needs for Quantum

08:40 Raising Capital in Quantum Tech

11:58 Government Support and Quantum

14:16 Photonics vs. Other Quantum Approaches

15:55 Talent Acquisition in Quantum

17:45 Global Operations and Foundry Partnerships

19:27 Staying Canadian in a Global Market

21:02 Maintaining Passion and Energy

22:12 Commercialization of Technology

25:09 Interplay Between Quantum and AI

27:06 Future of Quantum Hardware

28:34 Software Development in Quantum

31:18 Building Partnerships and Use Cases

33:10 Quantum Computing for Battery Development

34:31 Applications Across Industries

36:11 Future Predictions for Quantum Computing

37:21 Misconceptions About Quantum

38:46 Coping with Challenges in Business

Dennis Pilarinos is the Founder and CEO of Unblocked.

Unblocked brings all the context about your codebase together, so your team gets expert-level answers, no matter where they’re working.

Chapters

00:00 The Journey of Dennis

09:48 Building Developer Tools: Challenges and Insights

16:59 The Importance of User Experience in Development

24:45 AI's Role in Modern Development

29:58 Attracting Top Talent in Tech

34:19 The Evolution of Vancouver Tech Ecosystem

Mark Doble is the CEO of Alexi.

Alexi is the flexible AI platform trusted by leading law firms to develop proprietary insights, orchestrate high-quality work, and deliver stronger results — in a fully private, firm-controlled environment.

Chapters

00:00 Exploring the Gaps in Legal Tech

05:26 The Evolution of Legal Research Automation

08:00 Understanding AI Hallucinations in Legal Contexts

12:20 The Role of Human Lawyers in an AI-Driven World

15:38 Building a Platform for Law Firms

20:12 Navigating the Challenges of Long-Term Implementations

24:35 The Future of Law Firms in the Age of AI

30:19 Balancing Innovation and Customer Needs

35:11 The Impact of AI on Legal Product Development

39:01 Dealing with Hard Times in Entrepreneurship

Stu Szabo is the Co-Founder and CEO of Beacon.

Beacon is a new solution built to facilitate smooth transitions for immigrants relocating to Canada.

Their Super App simplifies the financial and informational hurdles that newcomers face, offering everything from banking solutions to essential resources, all designed to ease the transition into Canadian life.

Chapters

00:00 The Inspiration Behind MyBeacon

07:14 Transitioning from Investor to CEO

12:36 Rethinking Financial Services

16:28 The Immigrant Experience in Canada

20:41 The Necessity of Immigration for Canada

24:01 Strategic Focus on Nationalities

25:13 Rethinking Financial Services

26:29 Identifying Unique Pain Points

28:21 Innovative Solutions for Bill Payments

30:21 Cultural Differences in Financial Experiences

32:51 Challenges for Newcomers in Canada

37:24 Navigating Complex Financial Landscapes

40:08 The Journey to Launching a Startup

44:09 Overcoming Hard Times in Entrepreneurship

46:47 Introduction and Importance of Following the Podcast

Andrew Ostro is the Co-Founder and CEO of PolicyMe.

PolicyMe's mission is to reinvent insurance for Canadians by merging smart technology with unwavering humanity–driving down costs, simplifying protection, and prioritizing your needs at every step.

Chapters

00:00 The Birth of PolicyMe

05:25 Understanding Life Insurance

08:37 The Buying Process of Life Insurance

11:36 Streamlining Insurance Pricing

14:40 Innovations in Underwriting

17:17 AI and Operational Efficiency

21:18 Types of Life Insurance

25:03 Product Expansion and Strategy

30:46 Navigating the Insurance Landscape

35:34 Marketing and Growth Strategies

43:21 Coping with Challenges as a Founder

Kylan Gibbs is the Co-Founder and CEO of Inworld.

Inworld develops AI products for builders of consumer applications, enabling scaled applications that grow into user needs and organically evolve through experience.

Chapters

00:00 Founding Story of Inworld

05:29 Consumer vs. Enterprise AI Applications

08:33 Bridging the Gap: Prototypes to Production

11:34 Runtime: Scaling Consumer AI Applications

14:20 Experimentation and User Engagement

17:18 The Complexity of AI in Consumer Products

20:11 Personalization in AI Experiences

23:17 The Future of Consumer AI Applications

25:56 Building Robust AI Systems

29:08 Consumer Adoption of AI Tools

31:50 Navigating the AI Landscape

34:38 The Role of Runtime in AI Viability

37:47 The Future of Consumer Apps in the AI Era

40:36 Getting Started with Runtime

43:34 Kylan's Journey and Insights

45:18 Coping with Challenges as a Founder

Mike Peasgood is the Co-Founder and CEO of ENVGO.

ENVGO is a technology company bringing cleantech solutions to the boating industry. At ENVGO, they are making high performance boating clean, efficient, and low maintenance.

They are building a future where hydrofoiling electric watercraft are powered by clean energy, and offer an experience of flight over the water.

Chapters

00:00 Founding Aeryon Labs (acquired by FLIR Systems)

05:32 Building Aerial Robotics: Key Differentiators

08:13 The Birth of ENVGO: Passion for Electric Boating

11:28 Hydrofoils and Performance: Redefining Boating Experience

15:12 Market Use Cases: Early Adopters and Applications

18:49 Electric vs. Combustion: The Noise Factor

22:26 Designing the Future: Aesthetic and Functional Integration

25:47 Manufacturing Challenges: Scaling Production

29:23 Branding and Customization: Creating a Unique Identity

32:55 Navigating Hard Times: The Importance of Teamwork

Daniel Wigdor is the Co-Founder and CEO of AXL.

AXL is a Canadian venture studio transforming world-class research into high-growth companies that shape the future of applied AI.

Led by seasoned tech entrepreneurs and applied AI experts, AXL’s mission is to ensure Canada’s top breakthroughs are built and scaled at home.

By connecting academia with real market demand and full-stack venture creation, AXL helps Canada move from invention to impact, anchoring talent, intellectual property, and long-term economic value within the country.

Daniel is also a Professor in the Department of Computer Science at the University of Toronto. Daniel previously founded and sold Chatham Labs to Facebook and became the founding director of Meta’s Reality Labs in Toronto.

Chapters

00:00 Canada's Innovation Struggles

05:05 The Impact of AI on Innovation

08:20 Bridging the Gap: From Research to Entrepreneurship

12:20 Corporate Perspectives on AI

18:54 The Evolution of AI Applications

22:52 Exploring the Application Space in AI

24:20 Cultural Shifts in Startup Environments

26:19 The Role of Immigrants in Entrepreneurship

26:51 Innovative Approaches to AI in Education

29:58 Leveraging University Networks for Startup Success

31:43 Government Policies and AI Development

34:29 Proposed Changes for AI Policy in Canada

37:24 Investment Structures in Venture Studios

39:21 Navigating Challenges in Startup Founding

40:48 What Makes a Successful Venture Studio?

Zane Hengsperger is the Founder and CEO of Nox Metals.

Nox Metals is the modern factory for fast, low-cost metals.

Chapters

00:00 Inspiration Behind Metal Fabrication

05:42 Current Landscape of Metal Processing

08:20 Sourcing and Quoting in Metal Fabrication

11:08 Geographical Considerations in Metal Supply

13:47 Venture Capital and Manufacturing

16:42 Navigating the Re-Industrialization Movement

19:06 Automation and Operational Efficiency

22:03 Building a Diverse Team for Manufacturing

24:52 Scaling Physical Space in Manufacturing

27:34 Custom Software Solutions in Metal Fabrication

30:13 Understanding Metal Types and Quality

33:11 The Energy of Re-Industrialization

35:54 Thoughts on Roll-Ups in Manufacturing

38:46 Overcoming Challenges in Hard Tech

38:47 Introduction and Importance of Following the Podcast

Andrew McLeod is the Co-Founder and CEO of Certn.

Certn isn’t a background check provider with a tech department; it’s a tech-first leader innovating every part of the background screening process.

Certn is changing background screening globally by offering the easiest-to-use platform, checks in 200+ countries and territories, free 24/7 customer support, and fast and compliant results.

Trusted by 10,000+ clients, Certn helps businesses manage risk, stay compliant, and hire faster—all while delivering candidate experiences that help them stand out.

Chapters

(00:00) Pod Intro

(01:56) Entrepreneurial Roots and Early Ventures

(04:09) The Importance of Transparency in Business

(05:54) Building Strong Co-Founder Relationships

(07:41) Fostering an Entrepreneurial Environment

(09:45) Understanding Customer Needs for Growth

(11:20) The Role of Relationships in Sales

(13:30) Product Expansion and Market Strategy

(15:34) Building a Remote and Global Team

(19:31) Navigating Regulatory Challenges

(22:49) Insights on Canadian Tech and Startups

(30:21) The Impact of AI on Business Operations

(34:17) Lessons Learned from Nearly a Decade of Entrepreneurship

Daniel Eberhard is the Founder and CEO of KOHO.

KOHO is one seamless platform for your money and life. Founded in 2014, they are a forward-thinking fintech company dedicated to financially empowering a generation of Canadians.

With a Mastercard and innovative tools, they provide their users with the ability to earn, spend, borrow, build credit, and budget—all in one convenient app.

Driven by a genuine desire to help people make financial progress, KOHO has touched the lives of over 1.7 million users.

Chapters

(00:00) Intro
(02:23) The Importance of Team Size and Revenue Per Employee (RPE)
(04:38) The Role of AI in Business Efficiency
(08:18) Canada-US Dynamics in Tech and Innovation
(10:33) Cultural Identity and Building a Winning Mindset in Canada
(12:05) The Value of Data vs. Intuition in Product Development
(15:53) Experience vs. Horsepower in Hiring
(19:21) Learning from Mistakes and Public Criticism
(22:39) Hiring Practices and Probation Periods
(25:01) AI Integration and Development at KOHO
(28:47) Learning and Growth
(31:02) Government Spending and Economic Concerns
(35:59) Energy Management and Longevity in Leadership

Boris Wertz is the Founder and General Partner of Version One Ventures.

This is the second time Boris has been on the podcast; this time, we were able to do it in person.

Version One Ventures backs mission-driven founders who are early in new areas such as Ada, Coinbase, Ether.fi, Jobber, Patch, Shippo, Outreach, Uniswap.

Chapters

(2:45) Introduction to Boris Wirtz and Version One Ventures
(5:33) Founder Quality: The Core of Investment Decisions
(10:37) Generational Differences in Founders
(12:54) Exploring Opportunities in India
(14:58) Learning and Building Conviction in New Markets
(19:28) Post-Investment Relationships with Founders
(21:00) Structuring Version One Ventures
(23:34) Reflecting on the Anti-Portfolio
(25:37) Liquidity and Fund Management
(27:47) Fundraising Insights from a Former Founder
(29:41) Shifts in the Venture Landscape
(31:44) Common Pitfalls for Emerging Managers
(33:29) Opportunistic Investment Strategies
(34:41) Investment Stages: Pre-seed to Seed
(36:09) Decision-Making in a Lean Team
(37:33) Exciting Areas of Investment

Peter Hass is the GM at Stelumar.

Stelumar Advanced Manufacturing Inc. (SAMI) is a technology-driven company dedicated to revolutionizing homebuilding in Canada through advanced modular building solutions.

Founded by Peter Gilgan, one of Canada’s leading entrepreneurs and the founder of Mattamy Homes, SAMI combines automation, robotics and AI to produce high-quality prefabricated components at an industrial scale.

With a state-of-the-art facility set to open in the GTA, SAMI aims to address the housing crisis by making homeownership more attainable, accelerating construction timelines and setting a new benchmark for innovation in the industry.

Chapters

00:00 Peter Hass: A Journey Through PropTech

05:46 Understanding Prefab and Modular Construction

09:10 The Advantages of Speed in Construction

12:16 Mid-Rise Buildings: The Sweet Spot for Modular

13:27 Navigating Regulatory Challenges in Construction

17:01 The Impact of Robotics on Manufacturing

18:42 Transforming the Building Industry

19:59 Dispelling Myths About Modular Construction

21:56 Scaling Up: The Future of Manufacturing

23:44 Innovations in Home Building

25:26 The Cost of Housing: Breaking Down the Components

28:08 Customization in Modular Construction

30:03 Pricing Strategies in Modular vs Traditional Construction

31:08 Current Trends in the Real Estate Market

32:45 Policy Changes for Housing Affordability

34:17 The Future of Robotics in Construction

36:12 Lessons from Peter Gilgin

37:27 Finding Balance in Entrepreneurship

Kevin Jia is the Co-Founder of Quoted Tech Computers.

Founded in 2023, Quoted Tech was founded by two tech enthusiasts with a clear vision to change the world of hardware.

Quoted Tech has served over 10,000 customers across the country and is on track to hit $10M in revenue, completely bootstrapped.

Chapters

00:00 The Founding Story of Quoted Tech

06:24 Building Gaming Computers: The Process and Expertise

12:20 The Evolution of Gaming: From Consoles to PCs

17:12 Challenges in the Canadian Market: Sourcing and Accessibility

19:31 Bootstrapping and Scaling: Balancing Growth and Options

20:41 Bootstrapping and Early Challenges

24:07 Building Relationships and Partnerships

26:51 Marketing Strategies and Customer Acquisition

29:54 Customer Retention and Upgrades

31:59 Agility in Product Development

33:41 Navigating Hard Times and Resilience

40:27 Introduction and Importance of Following the Podcast

Philippe-Antoine Lehoux is the CEO of Missive. Missive is a shared inbox & team chat solution used by thousands of businesses worldwide.

Phil discusses his journey in bootstrapping businesses, emphasizing the importance of a customer-first approach, team dynamics, and the impact of AI on productivity. He shares insights on scaling, collaboration, and the email landscape, while also reflecting on his experiences with exits and the challenges of maintaining motivation over the long term.

Chapters

00:00 Bootstrapping: The Foundation of Success

04:54 Customer-First Approach: Building with Feedback

07:13 Team Dynamics: Scaling and Remote Work

09:34 AI in Productivity: Transforming Workflows

12:12 Innovating Email: The MISive Approach

14:50 Collaboration vs. Noise: Finding Balance

17:18 Exiting a Business: Lessons from ConferenceBatch

19:32 Zero to One: Building from Scratch

21:50 Founder Growth: Learning to Delegate

24:21 Scaling Strategies: Inbound Growth and Competitors

26:40 The Email Landscape: Trends and Challenges

29:10 Product Development: Balancing Feedback and Intuition

31:30 Global Reach: Navigating Different Markets

34:14 Sustaining Motivation: The Long Haul

36:16 Pricing Strategy: Balancing Value and Affordability

38:34 Coping with Hard Times: Finding Balance

43:06 Introduction and Importance of Following the Podcast

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My conversation with Chris Samra! Chris is building Waves, camera glasses for Creators, which are launching this week!

We discussed the evolving landscape of content creation, the future of wearable technology, and the importance of user experience in hardware design.

Timestamps

02:40 - The Vision of Invisible Wearables

07:35 - The Future of Content Creation

10:00 - Designing for Comfort and Aesthetics

11:08 - The Evolution of Hardware Development

13:12 - Monetization in the Creator Economy

15:36 - The Role of Technology in Wearables

17:58 - Insights from the Hardware Space

20:08 - The Waterloo Ecosystem and Startup Culture

22:29 - Navigating Challenges in Entrepreneurship

26:28 - Looking Ahead: Plans and Community Engagement

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Jack Newton is the Founder and CEO of Clio.

Clio is the world's leading provider of cloud-based legal technology, providing lawyers with low-barrier, affordable solutions to manage and grow their firms more effectively, more profitably, and with better client experiences.

Their products redefine how lawyers manage their firms by equipping them with the tools they need to run their firms securely from any device, anywhere.

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Chapters

00:00 Introduction + Supporters

02:20 The Journey of Fundraising and Early Challenges

09:12 Core Values and Company Culture at Clio

16:42 The Role of AI in Legal Tech

20:00 Maintaining Agility in a Growing Company

28:58 Reflections on Growth and Future Opportunities

33:20 Building a Thriving Canadian Tech Ecosystem

36:40 Sustaining Energy and Passion Over Time

Keywords

Clio, Jack Newton, legal tech, AI, company culture, fundraising, Canadian tech, startup growth, values, business strategy

Tuner Novak from Banana Capital.

Banana Capital is a Pre-Seed/Seed fund, and Turner also hosts The Peel Pod.

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Timestamps

02:40 - Canadian Roots and Identity

07:36 - The Future of Media and Content Creation

10:10 - The Importance of Distribution in Venture Capital

13:14 - Content Creation and Personal Enjoyment

15:40 - The Evolution of Influencer Investing

18:40 - Building Relationships and Inbound Opportunities

21:21 - Navigating the Investment Landscape

24:06 - The Role of Personal Branding in Venture Capital

29:05 - Understanding Venture Capital Returns

33:54 - Evaluating Founders and Their Potential

38:09 - Identifying Market Opportunities

42:59 - The Importance of Team Dynamics

46:01 - Balancing Work and Family Life

Keywords

Canadian roots, media, venture capital, distribution, content creation, personal branding, investment landscape, founders, market dynamics, work-life balance

James Clift is the Founder and CEO of Durable.

Durable makes owning a business easier than having a job. We’re building the world’s fastest AI website builder and all-in-one business platform, so anyone can launch online in seconds and grow with powerful AI tools.

Over 10 million websites generated. Used by business owners in 100+ countries.

Chapters

02:25 James Clift's Entrepreneurial Journey

05:54 The Vision Behind Durable

07:51 AI's Role in Business Transformation

10:59 Website Functionality and User Experience

15:40 The Future of Business Ownership

17:37 Trends in Business Creation

20:55 Navigating the AI Landscape as a Founder

26:07 Venture-Backed vs. Bootstrapped Businesses

29:37 Lessons Learned as a Founder

33:03 The Future of AI and Business

Keywords

Durable, James Clift, entrepreneurship, AI, website building, business ownership, venture capital, startup trends, user experience, business transformation

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