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
