The Hard Part with Evan McCann

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

Aidan Vaandering is the Co-Founder of Reserv Labs. Reserv is the yerba mate based focus + productivity drink made for the modern consumer. Takeaways Aidan's sales skills from Shopify and how they help as a founder. The branding and positioning of Reserv in a crowded market. Nuances with Red Bull, Monster and other energy products. Understanding customer rituals and where Reserv fits in. How new rituals can drive product adoption. Starting with DTC and how you can scale to $100M+ in revenue on DTC alone. Reserv's subscription model. Figuring out taste and ingredients for Reserv. "Scrappy Marketing". Vancouver's often-overlooked CPG scene, is full of numerous success stories. Chapters 00:00 From Sales to Startup: A Founder's Journey 03:03 The Genesis of Reserv Labs 08:45 Branding and Positioning in a Crowded Market 11:48 Understanding Customer Interaction and Rituals 15:42 Direct-to-Consumer Strategy and Subscription Model 20:30 Ingredient Selection and Product Taste 30:35 Market Expansion and Customer Density 33:58 Marketing Strategies: The Scrappy Approach 39:55 Networking in Vancouver's CPG Scene 40:03 Personal and Professional Excitement Ahead 44:05 Balancing Life as an Entrepreneur Keywords entrepreneurship, branding, direct-to-consumer, product development, marketing strategies, customer interaction, subscription model, Vancouver CPG, sales experience, startup journey

Ben Rollert is the Co-Founder and CEO of Composer. Composer is an automated trading platform that allows you to build a portfolio of hedge fund-like strategies. Takeaways Ben's first founder experience with Intervaliq. Learnings from building Breather (raised $100M+). The importance of a solid business model cannot be overstated. Keeping a small team with Composer. Founder-led companies versus professional management. Understanding board dynamics. Doing market research to validate startup ideas. Using user feedback effectively. Why the team is based in Canada but can't operate here. The gap that Robinhood and Wealthsimple aren't focused on. Building products for prosumers. Building an AI product to empower users versus using AI for auto-trading. Chapters 00:00 Founding Experiences and Lessons Learned 09:03 The Breather Experience: Insights and Missteps 14:59 The Genesis of Composer: From Idea to Execution 25:06 Market Opportunities and Target Audience 32:00 Navigating Regulations and Business Models 39:04 Future Aspirations and the Role of AI Keywords founder experiences, Breather, Composer, market opportunities, regulations, business model, AI in trading, startup lessons, venture capital, trading software

Ori Eldarov is the Co-Founder & CEO of OffDeal. OffDeal is an AI-native investment bank for small businesses. They offer small business owners a hassle-free way to sell their company for the highest price to the best possible buyer. They leverage years of Wall Street experience and their custom-built proprietary AI technology to ensure your business attracts the highest number of buyers so that you can realize the full value of your life's work. OffDeal also offers buy-side services that assist buyers with proprietary deal origination (typically add-ons) and comprehensive market mapping/market research services to support due diligence or portfolio value creation. Takeaways His journey from i-banking at RBC to HBS to founding OffDeal. GenAI sparked Ori's interest in applying it to finance. His YC experience and learnings. Streamlining business transactions using technology. Marketplace challenges in SMB transactions. AI and human touch: The OffDeal Model. Building trust in a fragmented industry. Trends in SMB acquisitions: opportunities and challenges. Timing the market: when to sell a business. Scaling through founder-led sales. OPEX versus CAPEX. How OffDeal is focused on scale in a traditionally boutique space. Chapters 00:00 From Banking to Entrepreneurship: A Journey Begins 05:52 The Birth of OffDeal: Innovating Investment Banking 10:08 Marketplace Challenges in SMB Transactions 14:24 AI and Human Touch: The OffDeal Model 18:10 Building Trust in a Fragmented Industry 22:31 Trends in SMB Acquisitions: Opportunities and Challenges 27:58 Timing the Market: When to Sell a Business 30:37 Scaling Through Founder-Led Sales 33:12 Establishing Trust: The Key to Success 36:40 Creating Jobs and Delivering Value Keywords entrepreneurship, investment banking, OffDeal, AI, small business, marketplace, trust, M&A, trends, business sales

Asanka Jayasuriya is a Partner and CTO at 8VC. 8VC is a venture capital firm that invests in early-stage and growth-stage tech companies. It was co-founded in 2015 by Joe Lonsdale, who is also a co-founder of Palantir. The firm is headquartered in Austin. Takeaways Asanka's early days at UofT. The benefits of internships. Launching and building the Amazon Toronto office. The "Glass Ceiling" in Canadian tech Canada needs more successful tech companies to retain talent. Choosing and moving to Austin over SF or NYC. Meeting Joe Lonsdale while playing pickleball. Adapting to new trends in software development. Being a great engineering leader. How AI tools are impacting software development. How startups should structure their architecture early days, a focus on simplicity. Hiring early-stage SWEs and what to look for. Balancing speed versus quality early days. The true value of a 10x engineer lies in team amplification. How to hire a 10X engineer. How software purchasing criteria have evolved post-2021. Software perspective when building deeptech companies. Diving into 8VC's Build Program! AI tools will transform product development in the next decade. Chapters 00:00 Early Days at the U of T 05:32 Navigating the Glass Ceiling in Canadian Tech 11:11 Choosing Austin: A New Chapter 17:11 Adapting to New Trends in Software Development 22:42 Common Mistakes in Scaling Tech Teams 28:33 Evaluating Ideas and Milestones 34:03 Identifying Top Engineering Talent 40:09 The Future of AI Tools in Engineering Keywords career transition, software engineering, Amazon, Canadian tech, CTO, venture capital, hiring mistakes, tech leadership, AI in software, Austin tech scene, hiring process, venture studio, deep tech, engineering leadership, software purchasing, AI tools, mentorship, personal growth, CTO insights, investment strategies

Charlie Iscoe is the Co-Founder of CommonShares. CommonShares is a business succession platform that enables retiring owners to get fair value for their business while ensuring that their employees and communities are cared for. They facilitate fair and efficient exits for retiring owners, recruit, train and support succession leadership as required, and transition the business to employee ownership over time. They believe that business succession can be a win-win outcome for owners, workers, and communities. Takeaways Charlie transitioned from banking to entrepreneurship. Sunday Farms his first venture. Travelling around the world helped Charlie gain clarity on his entrepreneurial aspirations. CommonShares aims to address the succession planning crisis among small business owners. The "Silver Tsunami". Over 90% of small business owners lack a succession plan, creating a significant opportunity. Employee-owned companies tend to outperform their peers in various metrics. CommonShares' model. Financing and structuring deals. Post-acquisition support and operations. Common Shares is positioned to become the buyer of choice for businesses transitioning to employee ownership. Creating a "Win-Win-Win" model. Chapters 00:00 From Banking to Entrepreneurship 04:16 The Birth of Sunday Farms 10:22 Identifying the Silver Tsunami 18:17 CommonShares: A New Business Model 26:46 Financing and Structuring Deals 30:54 Post-Acquisition Support and Operations 39:00 Collaborations and Future Opportunities Keywords entrepreneurship, employee ownership, business succession, private equity, small business, investment, CommonShares, Sunday Farms, financial model, community impact

Landseer Enga, Co-founder of Revyl and former Uber innovator, dives into the transformative world of observability. He shares how Revyl emerged from a successful internal project at Uber, aiming to disrupt the market dominated by giants like DataDog and Splunk. Landseer emphasizes the crucial role of end-to-end testing in software quality and the strategic importance of lean teams in early-stage startups. He also discusses the evolving landscape of enterprise software with AI, and the advantages of in-person sales in a competitive tech environment.