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On the show
From 10 epsHost
Recent guests
Recent episodes
Alison Kaizer and Andrew D'Souza
Mar 30, 2026
54m 56s
Max Cunningham from Sesh
Jan 21, 2026
29m 25s
Ian MacKinnon from Stingray Security
Jan 14, 2026
38m 17s
Robert Farlow from Plato
Dec 11, 2025
32m 36s
Brent Lane from BigGeo
Nov 25, 2025
35m 23s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 3/30/26 | Alison Kaizer and Andrew D'Souza✨ | AI in hiringrecruitment practices+4 | Alison KaizerAndrew D'Souza | Golden VenturesBoardy | — | AIhiring+5 | — | 54m 56s | |
| 1/21/26 | Max Cunningham from Sesh✨ | nicotine alternativesmarket dynamics+4 | Max Cunningham | nicotine pouchesvaping+2 | CanadaU.S. | nicotinecravings+7 | — | 29m 25s | |
| 1/14/26 | Ian MacKinnon from Stingray Security✨ | phishingonline scams+4 | Ian MacKinnon | Stingray SecurityLater.com | — | phishingscams+5 | — | 38m 17s | |
| 12/11/25 | Robert Farlow from Plato✨ | Browser AgentsAI and Automation+3 | Robert Farlow | Plato | — | Browser AgentsAI+5 | — | 32m 36s | |
| 11/25/25 | Brent Lane from BigGeo✨ | Geospatial DataLocation-Based Insights+5 | Brent Lane | BigGeoAI+1 | geospatial data | geospatial datalocation-based insights+6 | — | 35m 23s | |
| 11/21/25 | Ignacio Tartavull from Pinkbot✨ | autonomous deliveryrobotics+4 | Ignacio Tartavull | Pinkbot | Toronto | last-mile deliverydelivery robots+5 | — | 43m 26s | |
| 11/10/25 | Ben Vinegar from Modem✨ | Developer ToolsSoftware Engineering+4 | Ben Vinegar | Modem | TorontoSan Francisco | Modemauto-triage+6 | — | 40m 52s | |
| 10/29/25 | Justin Sky from Rose Rocket✨ | Transportation Management SystemsAI in Business+5 | Justin Sky | Rose RocketY Combinator | Toronto | Transportation Management Systemworkflow automation+5 | — | 46m 33s | |
| 10/27/25 | Elan Lee from Exploding Kittens✨ | game designplayer feedback+5 | Elan Lee | Exploding Kittens | — | Exploding Kittensgame design+8 | — | 43m 40s | |
| 10/22/25 | Ahmed Nimale from KYD Labs✨ | live entertainmentticketing landscape+5 | Ahmed Nimale | KYD Labs | — | live eventsticket pricing+5 | — | 43m 08s | |
Want analysis for the episodes below?Free for Pro Submit a request, we'll have your selected episodes analyzed within an hour. Free, at no cost to you, for Pro users. | |||||||||
| 10/21/25 | Doug Roseborough | Doug Roseborough spent his career at multiple leading technology companies including 30 plus years at Oracle.Chapters00:00 Intro1:40 Early Days at Oracle02:56 Oracle's Secret Sauce05:16 Transition to the Bay Area08:15 Rolling Out Pricing Models10:31 Cultural Insights at Oracle13:05 Leadership and Team Dynamics15:35 Operations at Oracle17:59 Effective Meetings20:38 Customer Engagement Strategies23:00 Startup Advice25:37 Navigating a Noisy Market28:11 Bay Area Mentality30:31 Career Reflections and AI Impact33:06 Dealing with Hard Times | — | ||||||
| 10/17/25 | Tamer Shahin and Jerry Chen from Hiro | 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.Chapters00:00 Intro1:40 Inspiration Behind Hero02:55 Understanding Therapy for Children with Disabilities06:19 Gamifying Physiotherapy: The Solution08:25 Accessibility and Convenience in Physiotherapy11:39 Leveraging Technology for Progress Tracking14:02 Feedback from Parents and Therapists14:47 Pricing and Accessibility Considerations15:58 Market Size and Potential17:39 Product Development and Iteration22:25 Engaging with Families for Feedback26:14 Addressing Therapist Shortages27:31 Government Partnerships and Support28:06 Overcoming Challenges as Founders | — | ||||||
| 10/14/25 | Cameron Conn from Champlain | Cameron Conn is the CEO of Champlain.Cameron previously Co-Founded OneComply (acquired by GeoComply).Chapters00:00 Intro1:40 Cameron's Journey Through Industries07:51 Transitioning to Retail and Learning the Ropes12:14 Positioning and Pricing Strategies in Apparel19:11 Navigating Wholesale and Direct-to-Consumer Channels26:25 Navigating Industry Challenges27:36 The Vancouver Apparel Scene29:53 Understanding Manufacturing Relationships33:00 Designing Collections with Purpose35:22 The Value of Collaborations39:42 Complexity in Apparel Collections43:55 The Investment Landscape in Apparel48:30 Overcoming Hard Times | — | ||||||
| 10/8/25 | Robert Saunders from Ownright | 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. Chapters00:00 Intro1:40 The Genesis of Ownright07:14 Navigating Regulatory Challenges13:14 Financial Hurdles in Real Estate Transactions17:28 Growth Strategies and Market Expansion20:50 Understanding Pricing and Unit Economics24:38 Leveraging AI for Efficiency32:11 The Future of PropTech37:23 The Rebranding Journey41:36 Finding Balance in Entrepreneurship | — | ||||||
| 10/6/25 | Brennan Spellacy from Patch | 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.Chapters0:00 Intro1:40 The Evolution of Sonder: From Flatbook to Hospitality Innovator06:41 Transitioning to Patch: The Journey to Founding a Climate Solution11:07 Understanding Carbon Markets: The Role of Patch in Sustainability16:09 Navigating Complexity: Strategies for Chief Sustainability Officers20:43 Crafting Effective Sustainability Strategies: Insights from Patch24:21 Strategic Procurement in Carbon Credits27:49 Navigating Global Projects and Technology Risks31:28 Understanding the Global Carbon Market Landscape35:14 Pricing Dynamics and Industry-Specific Strategies38:58 Future Trends in Carbon Markets and Technology43:40 Resilience in Entrepreneurship45:44 Engagement and Community Building | — | ||||||
| 10/1/25 | Francois Lafortune from Diagram Ventures | 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.Chapters00:00 Introduction2:00 The Genesis of Diagram: A Venture Studio's Origin05:23 Navigating the Idea Flow: From Concept to Execution09:49 Criteria for Success: Understanding the Venture Creation Funnel13:54 Leveraging Competitive Advantage: The Diagram Ecosystem16:36 Finding the Right Founders: The CEO Search Process21:14 Funding Dynamics: Balancing Ownership and Attracting Investors24:37 Team Structure: Blending Operators and Investors27:18 Navigating the Entrepreneurial Landscape28:51 Identifying Market Opportunities31:05 Learning from Experience36:51 Signals of Success39:35 Emerging Trends Beyond AI41:04 Balancing Ideas and Execution44:15 Transitioning from Hands-On to Hands-Off46:41 Coping with Challenges in Entrepreneurship | — | ||||||
| 9/29/25 | Rishard Rameez from Zown | 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. Chapters00:00 Podcast Introduction2:00 The Spark of Innovation: A Reddit Post04:43 Identifying the Gaps in Real Estate Services11:16 Transforming Home Buying: The Financial Impact13:23 Overcoming Traditional Barriers in Real Estate14:46 Expanding Horizons: Geographic Growth and Market Dynamics16:25 Understanding the Real Estate Commission Structure20:30 Leveraging Technology for Scalability23:12 Marketing Strategies in a Noisy Market25:51 Navigating Market Dynamics and Economic Factors30:23 Finding Purpose in Hard Times | — | ||||||
| 9/26/25 | Michael Serbinis from League | 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.Chapters00:00 Podcast Introduction2:00 Getting Shit Done: The Core Philosophy07:02 Healthcare Challenges: Access and Understanding13:20 The Agentic Era: AI in Healthcare19:30 Learning and Adapting: The Key to Success22:23 Partnerships: Transforming Healthcare Together26:18 League's Platform Approach: A New Era in Healthcare31:49 Balancing Family and Business: A Personal Journey36:18 Perseverance in Hard Times: Lessons Learned | — | ||||||
| 9/25/25 | Nicholas Chepesiuk from Qualifacts | Nicholas Chepesiuk is the VP of Innovation at Qualifacts.Nicholas was the Founder & CEO of OnCall Health, which was acquired by Qualifacts in 2022.Chapters00:00 Podcast Introduction2:00 Foundational Experiences in Early Roles07:21 Telehealth Surge: Impact of the Pandemic12:53 Post-Acquisition Insights and Growth Strategies18:06 Trends and Opportunities in Healthcare23:19 Building a Strong Company Culture28:21 Personal Resilience and Coping Mechanisms | — | ||||||
| 9/19/25 | Derrick Emsley from tentree and veritree | Derrick Emsley is the Co-Founder of tentree and veritree.Chapters00:00 Podcast Introduction2:00 The Genesis of Tentree05:04 Lessons Learned in Entrepreneurship07:36 Transitioning to Veritree09:07 Navigating the Climate Tech Landscape12:07 Project Selection and Impact14:52 Building Partnerships and Verification17:37 The Importance of Trees20:24 Consumer Behavior and Local Impact23:12 Trends in Sustainability25:52 Metrics and ROI in Sustainability28:38 Learning and Growth as a Founder31:26 Team Dynamics and Culture34:09 The Role of Impact in Business37:01 Technology in Tracking Projects39:52 Overcoming Challenges in Entrepreneurship | — | ||||||
| 9/17/25 | Chloe Liang from Cocasa | 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.Chapters00:00 Podcast Introduction2:00 From Banking to Founding: Chloe's Journey10:31 Identifying the Problem: Cocasa's Mission21:08 Understanding the Cocasa Model35:25 Navigating Challenges as a Founder40:06 Engagement and Community Building | — | ||||||
| 9/15/25 | Kyle Norton from Owner | Kyle Norton is the Chief Revenue Officer at Owner.Chapters0:00 Podcast Intro2:00 Evaluating Companies: The Key Factors07:38 Building a Revenue Team: Initial Steps and Strategies11:39 Quality Over Quantity: The Importance of Revenue Quality15:49 AI in Sales: Internal and External Impacts20:42 Navigating the Changing Landscape of Outbound Sales26:58 Hiring for Success: Qualities in Sales Roles33:15 The Hybrid Work Debate: In-Person vs Remote38:47 Geographic Strategy: Where to Position Sales Reps44:09 Continuous Learning: The Benefits of Advisory Roles47:20 Resilience in Sales: Maintaining Drive Through Challenges52:31 Introduction to the Hard Part Podcast52:31 Engagement and Community Building | — | ||||||
| 9/10/25 | Benjamin Bergen from Council of Canadian Innovators | 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.Chapters00:00 Podcast Introduction2:45 Reflecting on a Decade of CCI's Impact05:32 Understanding the Shifts in Innovation Policy08:10 The Importance of Effective Government Policies11:16 Building Stronger Industry-Government Relationships13:37 Navigating National Sovereignty in a Global Economy16:44 The Role of Government Procurement in Innovation25:10 Navigating Government Contracts and Policy Advocacy29:23 Capital Investment and Government's Role32:24 Tax Competitiveness and Brain Drain34:25 CCI's Mandate to Innovate36:02 Navigating Federal and Provincial Regulations38:29 Intellectual Property in the Innovation Economy42:08 Engagement Between Government and Industry44:07 Finding Purpose in Challenging Times | — | ||||||
| 9/8/25 | Nicole LeBlanc from Woven Capital | 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. Chapters00:00 Podcast Introduction 2:45 Introduction to Woven Capital05:38 Investment Strategy and Structure08:13 Exciting Technologies and Market Trends11:18 Post-Investment Support and Value Addition14:16 Global Investment Focus and Cultural Insights16:53 Diverse Applications of Toyota's Expertise19:44 Robotics and Future Trends22:38 Corporate Venture Capital Landscape in Canada25:16 Learning as an Investor28:07 Fund Structure and Investment Strategy31:08 Cultural Differences in Business Practices33:42 Deep Tech and Hardware Investments36:27 AI Applications and Industry Trends39:23 Resilience and Optimism in Challenging Times | — | ||||||
| 9/5/25 | Anthony Azrak and Jai Mansukhani from OpenSesame | 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.Chapters0:00 Introduction2:45 Introduction to Speedrun and OpenSesame's Experience05:30 Identifying the AI Gap and OpenSesame's Focus08:20 Customer Use Cases and Product Iteration11:08 Target Market and Software Company Dynamics13:58 The Future of AI Interaction and User Experience16:49 Navigating the AI Landscape and Customer Education19:33 Feature Development and Revenue Opportunities22:34 Customer Discovery and Feedback Mechanisms25:05 The Future of Work with Natural Language Interfaces28:30 Raising Capital and the SF Ecosystem32:25 The Language User Interface Revolution37:21 Team Dynamics and Hiring in the AI Era40:37 The Advantages of Being in Silicon Valley42:49 Navigating Challenges as a Founder | — | ||||||
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