The Hard Part with Evan McCann

Oban MacTavish is the Co-Founder and CEO of Spade.Spade is the only transaction data enrichment solution backed by real data. They leverage their vast first-party data network to bring instant clarity and context to every purchase and payment—with precisely matched merchant, category, and geolocation details that empower you to build the next generation of financial technology.Chapters- Oban's First Founder Experience with Hubly- Understanding Merchant Intelligence and Data Quality- Fraud Detection and Prevention Strategies- The Role of Rewards and Consumer Trust- Fintech Tailwinds and Market Opportunities- Building in an Ambiguous Data Landscape- AI's Impact on Fintech and Data Quality- The Value of Data in Modern Business- Understanding Customer Needs and Sales Strategies- The Y Combinator Experience and Early Customer Engagement- Insights on Fundraising and Investor Relationships- Building a Lean Team and Remote Work Dynamics- Navigating the US Market as a Canadian Startup- Identifying Your Strengths and Delegating EffectivelyChapters00:00 The Genesis of Hubly and Founding Experiences02:48 Transitioning to Spade: Lessons Learned06:05 Understanding Merchant Intelligence and Data Quality08:53 Fraud Detection and Prevention Strategies11:57 The Role of Rewards and Consumer Trust15:06 Fintech Tailwinds and Market Opportunities17:56 Building in an Ambiguous Data Landscape20:56 AI's Impact on Fintech and Data Quality24:27 The Value of Data in Modern Business26:22 Understanding Customer Needs and Sales Strategies30:38 The Y Combinator Experience and Early Customer Engagement32:38 Insights on Fundraising and Investor Relationships36:10 Building a Lean Team and Remote Work Dynamics38:36 Navigating the US Market as a Canadian Startup40:57 Identifying Your Strengths and Delegating Effectively44:58 Making Critical Decisions and Self-Care47:55 Coping with Challenges and Seeking SupportKeywordsSpade, fintech, data quality, fraud detection, merchant intelligence, rewards, consumer trust, AI, startup experience, data value, customer engagement, sales strategies, Y Combinator, fundraising, lean teams, remote work, Canadian startups, decision making, self-care

Rob Fraser, Founder and CEO of Outway, dives into the evolution of his sock company and the transformative challenges faced over two years. He shares insights on the balance of personal growth with business resilience and strategic decision-making, particularly in channel expansion. Fraser discusses the exciting impact of AI on consumer goods and the growing Canadian product movement. He also emphasizes the crucial role of innovative sock design in building customer loyalty and the importance of navigating opportunities with agility.

The Friday Show Episode 3!2:26 - Burhan from Rondah AI17:46 - Ruslan from Float48:51 - Jake from Pilgrim1:11:00 - Fahd from Roach Capital + Studio 5351:26:10 - Vedant from Opennote

Sheetal Jaitly is the CEO of TribalScale.TribalScale builds digital products and transform businesses. They help the world’s largest enterprises and best entrepreneurs identify strategic opportunities to build, design, and release cutting-edge technology solutions to benefit their customers.Takeaways- Xtreme Labs Experience and Mafia- Navigating Digital Transformation and AI- Building a Successful Service Business- Zero to One: Finding Product-Market Fit- Hiring for Success: Traits to Look For- Empathy and Curiosity in Networking- The Miami Tech Boom- Navigating Client Relationships in an AI World- AI's Impact on Enterprise Leadership- Investing in the Future: Insights from G CapitalChapters00:00 The Xtreme Labs Experience06:07 The Birth of Tribal Scale11:25 Navigating Digital Transformation and AI16:10 Building a Successful Service Business19:47 Zero to One: Finding Product-Market Fit21:46 Hiring for Success: Traits to Look For25:38 Empathy and Curiosity in Networking28:12 The Miami Tech Boom31:41 Navigating Client Relationships in an AI World35:25 AI's Impact on Enterprise Leadership38:00 Investing in the Future: Insights from G Capital40:47 Personal Growth Through Hard TimesKeywordsXtreme Labs, Tribal Scale, digital transformation, AI, service business, entrepreneurship, product-market fit, hiring, startup culture, innovation, networking, empathy, Miami tech, AI, client relationships, investing, resilience, entrepreneurship, thought leadership, startup culture

Aydin Mirzaee is the Co-Founder and CEO of Fellow.Fellow.app is an all-in-one AI meeting assistant designed for remote and hybrid teams, offering transcription, summaries, and action item tracking. It streamlines meetings with collaborative agendas and integrations, helping teams work smarter and faster.Takeaways- Being the First Canadian on Facebook- The Story of Bok - Aydin's First Venture- Lessons from Fluidware and Acquisition by SurveyMonkey- Lessons and Learnings on Pivoting- Co-Founding Dynamics: Building Strong Relationships- Navigating Competition: Evolving with the Market- Building a Holistic Meeting Platform- Transforming a Scaling Company: The Pivot- Embracing AI: A Cultural Shift- User Experience: Balancing Simplicity and Engagement- The Ottawa Tech SceneChapters00:00 The Facebook Journey: A Canadian Perspective02:58 Entrepreneurial Pivots: The Story of Bach05:51 Lessons from Fluidware and Acquisitions09:59 The Genesis of Fellow: Returning to Entrepreneurship17:01 Co-Founding Dynamics: Building Strong Relationships20:06 Navigating Competition: Evolving with the Market24:02 Building a Holistic Meeting Platform26:25 Transforming a Company: The Pivot31:12 Embracing AI: A Cultural Shift35:14 User Experience: Balancing Simplicity and Engagement39:05 The Ottawa Tech Scene: A Thriving Community41:02 Adapting to Change: Learning and Growth46:19 Coping with Challenges: The Importance of SleepKeywordsFacebook, entrepreneurship, pivots, acquisitions, Fellow, Fluidware, competition, co-founders, AI, business strategy, AI, meeting platform, company transformation, user experience, Ottawa tech, coaching, business challenges, sleep, productivity, innovation

Jonathan Shaanan is the Managing Director of Circle K Ventures.Established in 2020, Circle K Ventures invests in startup companies that are developing and deploying solutions that enhance the experience in our stores while providing team members with the tools and resources that free them up to focus on our guests.Takeaways- From Banking to Venture Capital: A Journey- The Birth of Circle K Ventures- Navigating Corporate Venture Capital (CVC)- Strategic vs. Financial Returns in CVC- Innovations Shaping Retail: Technology and Trends- Global Perspectives: Investing Beyond Borders- Post-Investment Value: Building Relationships- Due Diligence in a Real-World Context- Launching and Testing Technology In-Store- The Future of Corporate Venture Capital in CanadaChapters00:00 From Banking to Venture Capital: A Journey02:46 The Birth of Circle K Ventures06:05 Navigating Corporate Venture Capital08:52 Strategic vs. Financial Returns in Venture11:47 Innovations Shaping Retail: Technology and Trends18:01 Global Perspectives: Investing Beyond Borders24:00 Post-Investment Value: Building Relationships30:02 Due Diligence in a Real-World Context34:04 The Future of Corporate Venture Capital in CanadaKeywordsventure capital, corporate venture, Circle K Ventures, investment strategy, fintech, retail technology, startup ecosystem, innovation, entrepreneurship, investment banking

Eldon Sprickerhoff is the Founder of eSentire.eSentire is the Authority in Managed Detection and Response, protecting the critical data and applications of 2000+ organizations in 80+ countries, representing 35 industries from known and unknown cyber threats.Eldon is also an author of Committed: Startup Survival Tips and Uncommon Sense for First-Time Tech Founders and a Strategic Advisor at Caledon Ventures.Takeaways- Starting eSentire during the Dot-Com Bubble- Lessons from 20 Years of Business Growth- Navigating Fundraising Challenges- Scaling Teams and Managing Growth- Understanding People Dynamics in Startups- How to Properly Filter Advice and Mentors- Revenue Milestones and Business Evolution- Building a Sales Team for Success- The Evolution of Sales Messaging- Navigating Growth and Change- Advising the Next Generation of Cybersecurity Startups- The Journey of Writing a Book- The State of Canadian TechChapters00:00 The Genesis of eSentire03:31 Lessons from 20 Years of Business Growth12:26 Navigating Fundraising Challenges14:39 Scaling Teams and Managing Growth17:57 Understanding People Dynamics in Startups21:11 Valuable Advice and Mentorship Experiences24:03 Revenue Milestones and Business Evolution27:24 Building a Sales Team for Success29:50 The Evolution of Sales Messaging31:12 Navigating Growth and Change34:46 Advising the Next Generation of Cybersecurity Startups39:33 The Journey of Writing a Book42:42 The State of Canadian Tech50:51 Personal and Professional Reflections55:29 Coping with Challenges and StressKeywordseSentire, entrepreneurship, business growth, fundraising, team scaling, startup advice, mentorship, revenue milestones, sales strategies, founder experiences, sales messaging, business growth, cybersecurity startups, writing a book, Canadian tech, personal development, entrepreneurship, stress management, startup journey, mentorship

The Friday Show Episode 2!12:10 - Arsham from Ribbon25:30 - Sean from Bold Bar37:30 - Xander Chin50:00 - Antonio from Trails and Bagelhacks

Hassan Ismail is the Co-Founder and CEO of West Tek.West Tek is building the next generation of data and software infrastructure to seamlessly connect traditionally disconnected human systems.Takeaways- The Genesis of a Defense Tech Startup- Autonomous versus Human Systems- Navigating the Conservative Defense Industry- Where Canada Is Investing in Defense- The Human Element in Warfare- What Future Warfare Looks Like- The Taboo of Defense Technology- Data Integration and Future ProspectsChapters00:00 The Genesis of a Defense Tech Startup10:55 Navigating the Conservative Defense Industry20:54 The Human Element in Warfare28:02 The Taboo of Defense Technology34:00 Data Integration and Future ProspectsKeywordsdefense tech, startup, autonomous systems, soldier systems, Canada, innovation, military technology, human element, data integration, manufacturing

Richard Waines is an Investor at DCVC Bio.DCVC Bio invests in early-stage, deep-tech life science companies that are leveraging computational approaches, including AI and automation, to transform existing technologies and accelerate the development of new ones. Chapters/Takeaways03:19 → Journey into Biotech Investing11:53 → DCVC Bio's Focus and Investment Strategy16:19 → Exploring Platform Therapeutics in Biotech20:15 → Nuances of Biotech Investing vs. Other Industries23:11 → Managing Science Risk in Biotech Investments27:58 → Key Personnel Changes During Company Growth30:24 → Geographical Considerations in Biotech Investments34:30 → The Passion for Science vs. Business in Biotech36:08 → The Role of an Associate in Venture Capital41:17 → The Impact of AI on Biotech Investments