The Hard Part with Evan McCann

Solon Angel is the Founder and CEO of a new stealth AI company. He previously founded MindBridge and is an active investor and advisor. Takeaways Why Solon actually didn't want to start MindBridge. His journey at MindBridge and key learnings. Working on AI in 2014 and how different the space looks today. Why founders who have been at their business for 10+ or 20+ years are outliers and not the standard. What he is building now. Importance of self-awareness as a founder. Solon's frustration with the current state of the Canadian tech scene, including regulatory policies and a mindset that needs to shift from a COVID-era mentality to a mindset of building success. The three types of founders are those motivated by money, those with something to prove, and those seeking fame. Success should be celebrated, and jealousy should be replaced with support and inspiration for others. Chapters 00:00 The Genesis Story of MindBridge 08:59 Transitioning Out of MindBridge 16:28 Rethinking Founder Roles and Responsibilities 28:10 The Potential of AI in Construction 31:18 The Importance of Self-Awareness for Founders 34:22 Celebrating Success and Shifting Mindsets 36:58 Moral Clarity in Leadership 44:52 Excitement for New Ventures and Personal Growth 51:31 Never Underestimate Human Ingenuity Keywords MindBridge, startup, accounting, irregularities, financial fraud, AI, machine learning, financial data analysis, financial analysts, compliance professionals, auditors, AI, construction, Canadian tech ecosystem, mindset shift, celebration of success, self-awareness, leadership, moral clarity, tax space, ventures, family, human ingenuity

Renae Farough is the Co-Founder and CEO of Kicker. Kicker is a next-generation copilot designed exclusively for sales professionals and leaders. Their innovative solutions integrate seamlessly with Salesforce and HubSpot CRMs, leveraging real-time third-party data and advanced generative AI to supercharge all stages of your sales process. Or as they like to say, "You sell, Kicker does the rest". Takeaways Salespeople spend more time not selling than selling. Top learning from Michael Hyatt. Impacts of AI on sales. Kicker's co-pilot business model. Finding a technical co-founder and how it went down to the wire. The focus on self-service onboarding. Raising capital while pregnant and as a new mother. Chapters 00:00 The Journey from Sales to Entrepreneurship: Challenges and Inspiration 04:07 Building Kicker: Finding the Right Technical Partner 35:37 Balancing Parenthood and Entrepreneurship: Resilience and Adaptability

Jeff Parks is the CEO of Stack Capital. Stack Capital Group is a publicly listed entity on the TSX that looks for disruptive growth and late-stage businesses primarily in Canada and the US to invest in. Their current portfolio includes exposure to Locus Robotics, SpaceX, Prove Identity, Newfront Insurance, Omio, Hopper, Varo, Bolt Financial and Canva. By investing in Stack Capital Group, investors gain exposure to disruptive pre-IPO companies that are very difficult to access. Additionally, since Stack Capital Group is publicly traded, investors are not locked up for long periods and can allocate holdings to registered accounts. Takeaways Why timing is crucial for going public. Signs such as hiring a CFO, investor relations focus, and revenue growth can indicate a potential IPO. Masterclass into secondaries, what they are, how they work, and how to acquire them from early investors, employees and founders. How to do due diligence and research on private companies. Why folks would get ownership in Stack's diversified portfolios versus taking cash. Dive deeper into Stack's unqiue business model. Chapters 00:00 Key Learnings at Venator 01:01 Genesis of Stack Capital 04:21 Valuing Equity in Private Companies 05:27 Adding Value to Founders 06:57 Due Diligence on Private Companies 07:25 Targeting Companies for the Portfolio 08:45 Red Flags in Private Companies 16:10 Valuations in the Private Market 20:30 Timing of Going Public 23:08 Signs of a Company Going Public 26:29 Reselling Founder/Executive Shares 27:06 Interesting Private Companies 28:41 Analyzing Businesses 31:48 Building Trust 34:33 Raising Capital for Stack 36:52 Dealing with Hard Times 39:30 Opportunities in Growth and Late Stage Assets

Alex Kolicich is a Founding Partner of 8VC. At 8VC, they partner with elite founders to build transformational technologies that create long-term economic and societal value. They are investors who never stopped being engineers, operators, policymakers, philosophers, and entrepreneurs. They are equally fervent realists and optimists, with an irreverence for convention and a reverence for wisdom. 8VC has invested in Flexport, Anduril, Asana, Blend, Deliverr, Ramp, Palantir, OpenGov, Vercel, Waabi and much more. Takeaways Going to UWaterloo and why the co-op program teaches grads to ship code and get things done. The startup culture at Waterloo prepares students for the world of technology and startups. Working at Google. Joining Clarium and Mithril (Peter Thiel's investment firms). Top learnings from working with Peter Thiel and Joe Lonsdale. Learnings from helping scale Palantir. Alex's learning curve in VC and not knowing what a Series A was initially. The founding of 8VC and what makes it unique in the VC space. 8VC's incubation program focuses on areas that require specialized knowledge, gatekeeper connections, and significant capital. Building relationships with industry experts and forward-facing corporations is crucial for success. Idea versus execution. Focus on areas like biotech and defense tech, which require substantial capital to start and scale. Alex's work with C100 and how we can improve Canada's tech ecosystem. Chapters 00:00 The Hardworking Culture and Startup Mentality at the University of Waterloo 06:19 Lessons Learned from Google and Palantir/Clarion: Infrastructure, Resources, and Perseverance 09:01 Building a Successful Company: Aptitude, Perseverance, and Not Giving Up 12:45 From Early Exposure to Venture to Founding 8VC: Being Opportunistic and Optimizing Opportunities 23:42 Incubation at 8VC: Deeply Understanding the Customer and the Space 28:20 Investing in What Should Exist 30:16 Building Relationships with Industry Experts 33:43 The Balance Between Idea and Execution 38:17 The State of the Canadian Tech Ecosystem 43:42 Excitement for AI and Biotech 52:07 Managing Stress and Balancing Life 54:24 Understanding the Impact of Technological Progress Keywords University of Waterloo, engineering, co-op program, startup culture, Google, Palantir, Clarion, small startup environment, infrastructure, resources, fear of failure, building a successful company, aptitude, perseverance, not giving up, venture capital, Mithril Capital, 8VC, value add, first principles thinking, incubation, customer understanding, space disruption, investing, building companies, incubation program, specialized knowledge, gatekeeper connections, capital requirements, Canadian tech ecosystem, Peter Thiel, Joe Lonsdale, Formation 8, Anduril

Christian Levan is Front Row Ventures's Director of Portfolio Support and a VC Analyst Intern at White Star Capital. Takeaways His military experience in Singapore. How he joined Front Row Ventures. The impact FRV has had on the Canadian VC landscape and helping students land roles in the space. Christian's advice for young people breaking into VC. Landing internships at Inovia Capital and White Star Capital. Being a younger team member but still adding value to the firm. Chapters 00:00 Christian's Military Experience and Journey into Venture Capital 07:24 Front Row Ventures: Bridging the Gap for Canadian University Startups 15:57 Choosing the Right Path: Navigating Different Stages and Sectors in VC 28:28 Navigating the Challenges: Being a Young Professional in VC 34:12 Overcoming Hard Times: Resilience and Long-Term Perspective Keywords military, Singapore, conscription, venture capital, FRV, Front Row Ventures, Canadian VC, talent pool, early-stage investing, learning curve, choosing a fund, hard times, perseverance

Elijah Moore is the Co-Founder and CEO of Endor Health. Endor Health is a digital health platform that simplifies care and pharmacy access for people with diabetes. Takeaways The acquisition of CollageHR by People Corporation and learnings. Eli discovered he had diabetes and built a business to help others living with the disease. Why living with diabetes is unique and involves day-to-day management, month-to-month administration, and long-term health considerations. Building a healthcare startup requires a compound startup approach, integrating various aspects of care and services. Nuances to building a healthtech startup and breaking down what a compound startup is. Leveraging pre-existing communities for Endor's growth. Building and earning trust with Endor customers, Eli will jump on calls with customers to do that. Chapters 00:00 Introduction and Genesis Story of CollageHR 08:15 The Acquisition Process and Lessons Learned 18:34 Challenges of Living with Diabetes 20:40 The Burden of Living with Diabetes 25:22 Simplifying Diabetes Management with an All-in-One App 32:37 Building Trust with Customers and the Diabetes Community 34:59 The Compound Startup Approach to Diabetes Care Keywords entrepreneurship, venture, acquisition, diabetes, healthcare, community

Kate Bouchard, CEO and Founder of Loba Wellness, discusses branding, emotional connections with customers, prototyping a physical product, seamless user experience, B2B opportunities in healthcare, raising capital, building a supportive network as a founder, and harnessing authenticity in social media marketing. The podcast covers topics like aesthetics, unboxing experience, fundraising, and the importance of word-of-mouth marketing.

Ezio Bondi and Matt DuPerrouzel are the Founders of arte*. arte* offers innovative, consciously-sourced, fresh and creative salad kits. They keep the environment front-of-mind and support local farms and producers, making every meal both a feel-good and a win-win. Takeaways Bondi Produce started as a family business and has grown to become Ontario's largest food service provider. How Bondi has created the platform to launch arte*. The logistics of delivering perishable produce. The brand arte* focuses on chef-driven salad kits made with locally grown produce. Building relationships with retailers to get more shelf space. How to get feedback from customers in a retailer-driven space. Leveraging social. Bootstrapping arte*. How they create and launch new flavours. Chapters 00:00 The Story of Bondi Produce 02:49 Toronto New Food Co. 05:01 Chef-Driven Salad Kits 07:24 Building Relationships with Retailers 11:42 Leveraging Social Media and Content Creators 12:56 Self-Funding and Continuous Improvement Keywords Bondi Produce, family business, Ontario's largest food service provider, logistics, perishable produce, Toronto New Food Co., value-added solutions, slicing and dicing produce, meal kits, Art, chef-driven salad kits, locally grown produce, relationships with retailers, social media, collaborations, investment, new flavors, support system

Jordan McFarlen is the Managing Director at Conexus Venture Capital. Conexus Venture Capital (CVC) has launched its second $30M VC fund with a $15M first close from its founder, Conexus Credit Union. With Fund II and new leadership, the Regina-based VC firm aims to build on the groundwork laid by its first fund and Conexus-founded incubator Cultivator. Through its latest fund, CVC plans to invest in more early-stage Saskatchewan-based technology startups. Takeaways Jordan starting Cultivator and building a leading accelerator. Great versus good accelerator. Nuances and specific challenges that Saskatchewan founders face. Raising a $30M Fund II. Advantages of having a smaller tech ecosystem like agility, connectivity, a cohesive ecosystem, and the government's support through tax credits and non-dilutive funding. CVC's role in Saskatchewan funding early-stage startups and building relationships with other VCs for future funding rounds. Exciting Sask companies like 7Shifts (backed by Softbank), Coconut Software, Vendasta and more. The exciting next wave of Saskatchewan founders. Chapters 00:00 Joining Conexus and Creating Cultivator 03:22 Attracting Investors and Building Relationships 08:22 Transitioning from Founder to Investor 13:31 The Advantages of Investing in Saskatchewan 18:43 Creating a Flywheel Effect in Saskatchewan 21:19 The Launch of Connect Suspension Capital Fund 24:26 Interesting Companies in Saskatchewan 26:47 The Ambition of the Younger Generation 29:05 Balancing Learning from Others and Staying Authentic 30:55 Dealing with Hard Times 33:45 The Inspiration and Drive Behind Jordan's Work Keywords Saskatchewan, tech ecosystem, Cultivator, Conexus Venture Capital, incubator, challenges, community, mentorship, smaller market, ambition, drive

Taz Singh is the Founder of Guild. Guild is an all-in-one platform for events, presentations, and discussions designed to reduce the burden as communities scale. Takeaways People management is a crucial aspect of software development, and building trust within a team is essential for success. One-on-one meetings focused on annoyances and aspirations can help understand what motivates individuals and build trust within the team. Rotating team leads and prioritizing tasks based on pain versus frequency can foster collaboration and effective decision-making. Existing community platforms have limitations, and there is a need for a comprehensive solution like Guild. Guild is a platform that connects brands with communities and facilitates brand partnerships through a sponsorship marketplace. Communities can form guilds, which are groups of people with a common interest or craft. Guilds can be part of larger networks based on geography or interest, allowing for collaboration and value creation. Government policies that the UK tech space has and what we could potentially implement in Canada. Chapters 00:00 Patterns and Best Practices in Software Development 09:00 The Genesis of Guild and Lessons from Building Communities 14:50 Challenges of Existing Community Platforms 15:29 Building Trust and Collaboration within Teams 26:17 Driving Value from Corporations to Communities through Sponsorship 28:27 The Power of Guilds and Networks in Community Building 32:04 Automating Brand Partnerships with Guild's Sponsorship Marketplace 35:56 Insights from the Tech Scene in London and Canada 44:13 Exciting Developments for Guild in the Future 45:24 Dealing with Hard Times and Maintaining Fearlessness 47:04 The Importance of Contributing to Your Community Keywords consulting, software development, people management, trust, hiring, one-on-one meetings, team leads, pain versus frequency, community, community platforms, events industry, Guild, Guild, sponsorship marketplace, communities, corporations, guilds, networks, automation, brand partnerships