The Hard Part with Evan McCann

Jean-Michel Lemieux has an incredible profile. Former VP of Engineering at Atlassian Former CTO at Shopify Founder of DevDegree at Shopify Restaurant owner of Arlo in Ottawa Author of an upcoming book "Build Right Side" Founder of SeaPeopleTakeaways- Early Ottawa tech scene.- Moving to Australia to work for the iconic company Atlassian.- Building trust when leading a new team.- Being a product expert as a CTO is key.- Moving back to Ottawa and joining Shopify.- Scaling Shopify's engineering team from 50 to 3,000.- Work with Founders as an executive like Tobi at Shopify and Mike and Scott at Atlassian.- JML's take on Founder Mode.- Background behind DevDegree.- JML's take on effective communication as a leader.- A strong opinion on technology tools is essential as a CTO.- Launching and starting Arlo one of Canada's top 100 restaurants.- Similarities behind starting a restaurant and tech.- Building a boat and JML's plan to tackle a massive sailing trip.- Power of writing and his book.- SeaPeople, one of his latest ventures.Chapters00:00 The Early Ottawa Tech Scene02:23 Career Trajectory and the Move to Atlassian05:15 Lessons from Atlassian08:03 Transition to Shopify10:50 Scaling Teams at Shopify15:44 Working with Founders18:58 The Concept of Founder Mode21:24 DevDegree: Bridging Education and Industry24:25 Traits of a Modern CTO26:33 Optimizing Technology Teams for Speed and Efficiency27:43 The Intersection of Food and Technology: Starting a Restaurant29:42 Navigating Life After Shopify: A Personal Journey31:36 Exploring the Seas: Building a Boat and Community34:07 Finding Product-Market Fit: Lessons from Entrepreneurship37:20 Writing as a Passion Project: Insights from Building a Book39:04 Embracing a Growth Mindset in Business and Life41:10 The Sneaker Phenomenon: Unexpected Lessons from Shopify47:22 Looking Ahead: Personal and Professional AspirationsKeywordsOttawa tech scene, Atlassian, Shopify, tech leadership, founder relationships, scaling teams, DevDegree, modern CTO, technology, CTO, product design, entrepreneurship, restaurant, growth mindset, Canada, sailing, community, product-market fit

Ian Burgess is the President and CTO of Validere Technologies.Validere is an Emissions Management Software Platform that enables customers to integrate their operational and field measurement data for regulatory reporting and corporate emissions initiatives.Over 50 of North America’s leading energy companies rely on Validere’s technology and multidisciplinary experts to understand their emissions and navigate an increasingly complex environment with clarity and ease.Takeaways- Ian's background in physics.- The journey to product-market fit took longer than expected.- YC significantly influenced Ian's entrepreneurial perspective.- Emissions reporting.- Re-architecting the product for scaling.- Proximity to clients enhances business development efforts.- Energy companies face challenges when adopting new technologies.- High-touch service for happy clients.- Gen AI adds complexity to data management.- Ian's thoughts on raising.- Reflections on 10 years of building Validere.- It's hard to hire someone who is strong where you're weak.- Success is the time average of your successes and failures.- Early days of Pioneer Fund and angel investing.Chapters00:00 From Physics to Tech: Ian's Journey05:04 Lessons in Product Market Fit13:35 Re-architecting for Success19:19 Navigating Sales in the Energy Sector25:51 Adapting to GenAI and Client Needs32:39 The Importance of a Diverse Investor Base38:17 Reflections on a Decade of Entrepreneurship45:46 The Shift to Audiobooks and Learning51:21 Finding Balance in Hard TimesKeywordstech startup, emissions reporting, product market fit, Y Combinator, energy sector, measurement science, software development, client relations, generative AI, business strategy, Generative AI, team composition, investor base, CTO, entrepreneurship, change management, Pioneer Fund, audiobooks, personal growth, work-life balance

Vitaly Pecherskiy is the CEO and Co-Founder ofStackAdapt.StackAdapt is a digital advertising platform specializing in native, display, video, connected TV, audio, in-game, and DOOH advertising.Takeaways - Vitaly's time at AdParlour, Hussein Fazal's (Super.com Co-Founder) first company.- Bootstrapping StackAdapt early days.- Capital efficiency has been a core principle for StackAdapt's growth.- Maintaining a startup culture even as the company scales.- PMF is an ongoing evolution, not a one-time achievement.- Thoughts around decision-making.- The impacts of AI on advertising.- Motivation and competition drive Vitaly and his co-founders.- Co-Founder relationships.- How leadership roles change.- Find focus amidst rapid growth within the business.- The desire to build StackAdapt into a household name.Chapters00:00 The Genesis of StackAdapt03:51 Evolution of the Advertising Industry05:49 Bootstrapping and Capital Efficiency11:42 Scaling Leadership and Company Culture17:52 Maintaining Startup Energy in Growth20:19 Customer Evolution and Product Market Fit22:31 The Impact of AI on Advertising25:12 Shifts in Decision Making and Growth28:34 Personal Motivation and Competitive Spirit30:51 Adapting Leadership Roles Over Time34:09 Trends in the Advertising Space37:56 Focus Amidst Growth41:44 Building a Household Name43:35 Quickfire Round: Insights and ReflectionsKeywordsStackAdapt, advertising industry, capital efficiency, company culture, AI in advertising, product market fit, leadership, growth strategies, motivation, decision making

Kevin Michael is the Co-Founder & CEO ofTempo Labs.Build beautiful UIs 10X faster with AI - Tempo generates and edits high-quality react code directly in your codebase so you can ship UIs in minutes.Takeaways- Working at Chamath's Social Capital.- Customer obsession is crucial for product development.- AI will enable teams to focus on unique intellectual property.- Benefits of YC for Tempo.- Selling to startups.- Effective product launches (Product Hunt, etc.)- Investing in content for PLG.- Dogfooding Tempo.- Selling to developers.- AI pricing strategies.- WOM is vital in a noisy AI market.- Building in a noisy AI space.- In-person versus remote.- Intentionally choosing to build in Toronto.Chapters00:00 The Impact of Social Capital Fellowship05:15 Navigating Product Development at Perpetua09:29 Transitioning from Perpetua to Entrepreneurship11:10 The Genesis of Tempo Labs14:25 Identifying the Ideal Customer for Tempo17:05 The Future of Engineering Teams with AI19:04 The Value of Y Combinator21:31 Selling to Startups: Opportunities and Challenges24:07 Strategies for a Successful Product Launch24:36 Investing in Content for Product-Led Growth25:17 Dogfooding: Building Products for Yourself27:25 Challenges of Selling to Developers30:21 Innovative Pricing Strategies in AI32:21 Filtering Through the Noise in AI33:37 Building a Strong Hiring Culture39:03 Choosing Toronto: A Strategic Decision42:03 The Importance of Networking for Fundraising44:08 Personal and Professional Excitement46:07 Navigating Hard Times in BusinessKeywordsSocial Capital, startups, product development, entrepreneurship, AI, Y Combinator, Tempo Labs, engineering teams, product-led growth, customer collaboration, Product-Led Growth, Content Marketing, Dogfooding, Developer Tools, AI Pricing Strategies, Hiring Culture, Toronto Startups, Fundraising, Networking, Startup Challenges

Ben Cox is the Co-Founder & CEO of Page.Page uses advanced technology & AI to make it effortless for companies to gain real-time and personalized insight into government activities that can impact their business.Takeaways- Working at Shopify for over 10 years and moving from a junior role to a Director level.- Why lobbying was interesting to Ben.- Understanding the lobbying process.- Who are Page's customers?- Why AI is the unlock with information capture and analysis.- Understanding government dynamics.- AI can help cut through media biases and provide primary sources of information.- Global perspectives in government.- Staying ahead in the AI landscape.- Finding PMF early days.- Majority of the Page team worked together at Shopify and the benefits behind high trust.Chapters00:00 The Shopify Experience: A Journey of Growth04:21 Personal Growth and Career Progression06:45 The Genesis of Page: From Idea to Reality10:18 Understanding the Lobbying Process12:14 Customer Insights and Needs14:12 Navigating Government Dynamics19:31 Global Perspectives in Governance23:24 AI's Role in Information Consumption26:59 Finding Product-Market Fit29:08 Staying Ahead in the AI Landscape31:33 Building a High-Trust Team33:45 Personal and Professional Excitement37:50 Dealing with Hard TimesKeywordsShopify, Page, entrepreneurship, AI, lobbying, career growth, governance, product-market fit, team dynamics, personal development

Michelle Kwok, an Investor at Draper Associates and co-founder of FLIK, shares her journey from aspiring doctor to entrepreneur. She discusses the importance of community building for female founders and the lessons learned in scaling and monetizing a platform. Michelle delves into the emotional complexities of acquisition and her personal identity shift post-FLIK. She also highlights her MBA experience and her insights on venture capital, emphasizing founder empathy and exploring the vibrant NYC tech scene.

Amrita Gurney is a Fractional CMO. Amrita supports Seed to Series B stage startups as a fractional marketing leader. She has been a marketing leader at Audiobooks.com, CrowdRiff, Float and many more. Takeaways - Building challenger brands. - What makes a successful challenger brand. - Most founders don't know how to hire marketers. - Developing a deep customer understanding. - What Brand truly means. - Brand Strategy. - Building awareness for startups. - Alignment between the CEO and marketing. - Marketing requires a different mindset beyond just driving leads. - Cutting through noise is a significant challenge for marketers. - Creative content messaging standards are rising. - Video content remains underutilized in B2B marketing. - Founder-led marketing. -Scaling the marketing function + team. - Amrita's fractional work. Chapters 00:00 The Journey of a Marketer 06:32 Choosing the Right Companies to Work With 13:08 Foundational Marketing for Early-Stage Startups 19:43 Misconceptions About Brand 27:11 The Power of Founders in Marketing 34:02 Adapting to New Marketing Platforms 40:08 Finding the Right Marketing Fit Keywords marketing, challenger brands, startup marketing, brand strategy, B2B, B2C, marketing mistakes, early-stage startups, brand building, leadership alignment, marketing strategies, brand building, fractional marketing, content creation, B2B marketing, founder influence, marketing leadership, adapting to change, effective communication, industry trends.

Brendan Baker, a Partner at Rackhouse Venture Capital and former engineer, dives into his unexpected journey from engineering to venture capital. He shares insights on the evolution of fundraising, emphasizing the importance of narrative and networking. Discussion includes the rise of systematic funds and the transformative impact of AI on industries like supply chain. Brendan also highlights strategies for founders navigating a competitive landscape and the vital role of strong leadership in driving innovation.

Ben Gigone is the Co-Founder and CTO of Chexy. Chexy is the first tenant-facing payments platform that allows renters to earn rewards & build credit on rent, all while bringing rent payments into the 21st century. Takeaways - Growing up in an entrepreneurial family. - Genesis story behind Chexy. - Focusing on tenant needs to drive early customer adoption. - Building credit through rent payments. - Challenges behind building a fintech company in Canada. - User feedback and how to use it well. - Helping customers transition from renting to homeownership. - Hiring early team members at a startup. - Being a great early-stage CTO. Chapters 00:00 From Aerospace to Entrepreneurship 05:02 The Genesis of Chexy 11:15 Balancing Tenant and Landlord Needs 17:02 Unlocking Credit Through Rent Payments 28:26 Scaling the Tech Team 39:15 Personal and Professional Excitement Keywords entrepreneurship, Chexy, fintech, rent payments, credit building, startup journey, technology, rewards, tenant needs, landlord solutions

Sam Pillar is the Co-Founder and CEO of Jobber. Jobber is the easiest-to-use business management platform for home service businesses. Landscapers, maid services, and companies in dozens of other industries use Jobber to keep track of customers, schedule jobs, get paid, and more. Takeaways - Jobber began at Remedy Cafe in Edmonton with Forrest and Sam. - Early days of Jobber driving around to see and talk with customers. - Scaling the company and the product. - Staying close to customers has been critical for Jobber, especially as they scale. - Company culture and scaling it, building values and mission. - Hiring an executive leadership team (ELT). - Raising Jobber's first round from Boris at Version One Ventures. - Why the home services industry offers new entrepreneurs and young people many opportunities. - How Jobber is using AI to enhance customer support and streamline operations. - Every time the company doubles in size, new challenges arise. - Personal growth as the CEO. - Shifting trends with more young people interested in home services and how Jobber fits in. Chapters 00:00 The Genesis of Jobber 03:38 Scaling and Customer Engagement 09:49 Disseminating Company Culture 10:18 Hiring and Building a Leadership Team 18:07 Opportunities in Home Services 23:06 Product Development and Customer Needs 30:56 AI Applications in Jobber 35:07 Navigating Growth Challenges 39:27 Personal Growth as a CEO 44:08 Trends in Entrepreneurship 48:31 Looking Ahead: Personal and Professional Goals 50:25 Dealing with Hard Times Keywords Jobber, entrepreneurship, small business, software development, company culture, AI, home services, leadership, growth challenges, customer engagement