The Hard Part with Evan McCann

Alanna Lopes Souza is the Seed GM at Drive Capital. Drive Capital is a venture capital firm that invests in innovative companies with the potential for significant growth. Founded in 2013 by two former partners at Sequoia Capital, the firm focuses on investing in technology, healthcare, and consumer companies across various stages, from early to growth stage. Drive Capital aims to support entrepreneurs building businesses outside the traditional startup hubs like Silicon Valley, often focusing on the Midwest and other underrepresented regions. Takeaways Alanna's time in investment banking, consulting and joining SSENSE. Her time as Chief of Staff at SSENSE and the world of fashion. Her time at Plum Guide which included a global pandemic. Execution versus strategy. Drive's unqiue thesis and focus. The energy in Toronto's tech scene. Her interest in AI. Chapters 00:00 Alanna's Career Journey 05:09 The Importance of Execution 11:50 The Vibrant Toronto Tech Scene 36:59 Exploring Opportunities in AI and Healthcare Keywords career journey, investment banking, consulting, chief of staff, brand development, fashion industry, Plum Guide, vacation rental, core hosts, Drive Capital, investor, Toronto tech ecosystem, AI, healthcare, value creation, founders, support

Josh Gray, Co-Founder of Artemis, talks about the genesis of Artemis and the importance of data quality for AI. They discuss industries showing traction, co-founder relationships, mistakes, raising capital, and product-market fit. Insights on using Slack Connect, founder-led sales, and creating value with AI. The podcast covers navigating challenges, data quality, AI integration, work-life balance, and tech industry growth.

Tim Lynn is the Co-Founder of Startup TNT and a General Partner at TNT Capital. Startup TNT connects local startups and entrepreneurs with angels, supporters, and other investors. To date, we have invested over $11.5M in 90+ companies across Western Canada. Their goal is to help you build your startup from your hometown, providing the network, community, and capital to make that happen. Their flagship event, The Startup TNT Investment Summit, connects new and experienced angel investors with startups by investing at least $200K (oftentimes more, up to $500K+) in each local winner, and syndicating deals for other companies that catch the investors' eyes! Socials - Instagram, LinkedIn, Twitter, TikTok. Takeaways -How Startup TNT was started. -TNT's use of community as due diligence on investments. -How to build a successful non-profit. -How to engage non-tech HNW folks to invest in startups. -How TNT sticks out and builds trust with founders. -Expansion across Western Canada and beyond and how to scale the experience effectively. -Building a robust community. -Why more folks should be investing in their local startup scene. -TNT's new fund, fundraising, the thesis and more! Chapters 00:00 From Corporate Finance to Startup TNT 03:21 Building a Collaborative and Inclusive Startup Community 08:10 Attracting Investors and Supporting Local Entrepreneurs 12:34 Startup TNT's Unique Approach to Venture Capital 16:33 The Power of Community in Startup Success 27:41 Building a Strong Network of Investors and Connections 30:54 The Importance of Impactful Pitches 33:35 The Success of TNT's Nonprofit Entity 38:58 Future Goals: Expansion, Bridging Investments, and Larger Fund 41:18 Recommended Books: The Outsiders and Lying for Money 44:40 Personal Connections and Support in Challenging Times Keywords startup, community, entrepreneurship, investment, collaboration, startup, TNT, capital, connections, clout, venture capitalists, advisors, community, founders, support, fundraising, pitches, nonprofit, sponsors, government grants, fraud, community building

Antoine Nivard is a Co-Founder and General Partner at Blank Ventures, a $65M inaugural fund, where he invests in seed-stage enterprise and fintech software. Prior to founding Blank, he had the opportunity to help raise funds and establish Inovia Capital in Silicon Valley and was fortunate to partner with founders building companies like LightspeedCommerce (NYSE:LSPD), 1Password, Magical, BenchSci, Momentum, Vital Biosciences, Poka (acquired by IFS), DarwinAI (acquired by Apple), and many more. Takeaways -Early days joining Inovia. -Launching and growing the Inovia office in SF. -Discuss the power law and witnessing it firsthand. -Talent arbitrage when it comes to American tech companies with significant amounts of Canadian employees (ex. Faire). -Discuss Databricks that has two Canadian founders. -Why there has been a lack of company formation in Canada. -Canada needs to focus on building startup mafias, where successful entrepreneurs from companies like Shopify go on to start their own ventures. -Launching and raising capital for Blank Ventures. Chapters 00:00 Background and Joining Inovia 04:30 Experience at Inovia 11:02 Impact of Witnessing the Power Law 15:57 Talent Arbitrage in American Companies 18:38 Lack of Company Formation in Canada 25:30 Building a Startup Mafia in Canada 34:20 Focus on Blank Ventures 48:37 Favorite Book and Excitement for 2024 52:18 Dealing with Hard Times 54:16 Closing Remarks

Tyson Birchall is the Managing Director of Longbow Capital. Longbow Capital is a private equity investment management company based in Calgary, Alberta that invests in the North American energy, power and technology sectors. They invest in innovative companies that are doing things differently; companies that help bring energy to the world in the most efficient, cost effective and environmentally responsible manner. Since being founded in 1997, Longbow has been a long-term strategic partner and an engaged and effective shareholder in over 150 high-growth investments. Takeaways -Tyson's time in investment banking provided valuable skills such as entrepreneurship, thinking on your feet, and client service. -History of Longbow. -Tyson's concept of "The Holy Trinity" when it comes to energy transition investing. -Longbow's unqiue investment thesis when it comes to investing in energy transition and how it differs from other climatetech investors. -What Longbow looks for in the leadership team when investing. -Knowing the right time to sell a business. -Growing AUM as a private equity firm. Chapters 00:00 Introduction 05:02 Investing in the Energy Space: Backing the Right Teams 12:08 Longbow's Approach to Energy Transition 25:50 Knowing When to Sell a Business 32:54 Navigating Hard Times Keywords investment banking, entrepreneurship, energy space, energy transition, management teams, CO2 emissions, AUM, trust, hard times

Craig Follett is the Co-Founder and CEO of Peggy. Peggy is the social marketplace to buy and sell contemporary art. Peggy partners with galleries and artists, to make living with art accessible to all. Finally, you can buy incredible art at a price you can afford, and can later rehome an artwork with a fellow collector if your tastes change. Peggy does good by the artists themselves, who can finally earn artist royalties for all future secondary sales as well - something they miss out on today. This is all made possible using sophisticated and proprietary AI and ML which keeps buyers and sellers protected. Follow Peggy on Instagram! Takeaways Craig's internship at Spin Master inspired his entrepreneurial journey. Universe, Craig's previous venture, was a sharing economy platform that evolved into a ticketing and event management platform and was acquired by Live Nation/Ticketmaster. How Craig learned about the art world by attending Art Basel. Authentication in the art world and how Peggy does it at scale. Parallels between Universe and Peggy. Network effects that drive Peggy. Raising capital. The importance of co-founder relationships. Peggy addresses challenges faced by artists and collectors, such as provenance, catalogue raisonné and collecting royalties. The impacts of AI, VR and other technologies on the art world. Chapters 00:00 Spin Master and the Inspiration for Entrepreneurship 06:13 The Genesis Story of Universe 11:02 The Motivation Behind Starting Peggy 27:35 Lessons Learned from Raising Capital 32:30 The Excitement for AI Advancements 38:25 The Value of Investors with Marketplace Experience 42:05 Join the Art Revolution with Peggy Keywords Spin Master, Universe, acquisition, entrepreneurship, Peggy, art market, art, royalties, AI, authentication, co-founder relationships, network effects, challenges, future

Moien Giashi is a Principal at GreenSky Ventures. GreenSky Capital is one of the top Canadian venture capital firms (according to CVCA 2021, 2022, 2023) with a focus on early-stage Canadian startups in B2B SaaS and deeptech. Takeaways Transitioning from academia to venture. Deep tech investments require strong IP and moat. There is a perception of higher risk and longer wait times for returns in deeptech. Successful commercialization requires a combination of policy changes, university support, education, and funding. Common challenges that academic founders face when scaling their deeptech ventures. Showing ROI and educating LPs on deeptech. Education around venture capital as an asset class is needed to increase interest and understanding. The content strategy of GreenSky aims to educate and support founders. GreenSky's new fund Chapters 00:00 From Academia to the Venture Space 08:13 The Focus on Deep Tech at GreenSky 11:44 The Importance of Intellectual Property in Deep Tech Investments 13:49 The Limited Number of Deep Tech Investors in Canada 22:46 Challenges Faced by Deep Tech Founders 26:13 Attracting Canadian LPs and Institutions to Deep Tech 30:04 The Importance of Education in Venture Capital 30:32 Adding Value to Startups through Expertise and Support 33:28 Sourcing Quality Deals through Referrals and Ecosystem Partnerships 35:52 Educating and Supporting Founders through Content Strategy 38:05 Investment Focus and Check Size of GreenSky 42:49 Supporting a Spouse's Startup Journey 44:27 Dealing with Hard Times: Journaling and Seeking Support 47:28 Rejections in Fundraising: It's Not a Reflection of the Company Keywords academia, venture space, commercialization, research projects, deep tech, intellectual property, IP, deep tech investors, funding, deep tech founders, business skills, deep tech, Canada, ROI, venture capital, education, value add, deal flow, content strategy, fund structure, rejection, support

Rebecca Mazzara is the Founder and CEO of Calita Intimates. Underwear is our most intimate piece of clothing. Calita believes you should have it all. Beautiful, comfortable underwear - made ethically. Use code: EVAN20 for 20% off your Calita order! Takeaways -Being an early hire on the Shopify Plus team -How Rebecca met her first manufacturer and designed her first run of product. -The importance of unit economics. -Building a brand that resonates with customers involves being authentic, relatable, and responsive to their needs. -Being a solo founder and how to find and use advisors. -Why TikTok has been a huge channel for Calita. -Deciding to produce your product in North America or overseas, pros and cons to both. -Bootstrapping versus raising capital. Chapters 00:00 Rebecca's Journey from Shopify to Calita 06:30 Launching Shopify Plus and the Startup Within a Startup 14:43 Making the First Run of Product 34:29 Challenges and Rewards of Being a Solo Founder Keywords Rebecca Mazzara, Calita, Shopify, entrepreneurship, networking, collaboration, brand building, marketing, manufacturing, bootstrapping, raising capital, unit economics

Marley Alles is the Founder of rax. rax is Canada's peer-to-peer wardrobe rental app. You can borrow, lend, sell, and buy clothes all on one platform. You can make and save money on your closet Takeaways -Non-technical founder learning no code low code tools and finding SWEs. -Managing logistics on a local and national level. -Building, scaling and maintaining a marketplace. -Driving repeat usage through the product. -Influencer strategy. -Different pricing models, such as subscriptions, to enhance the user experience. -Launching a new app and driving growth are exciting prospects for the future of Rax. Keywords Marley Alles, Rax, early career, fashion rental, peer-to-peer, marketplace, logistics, demand generation, repeat usage, technical talent, influencer strategy, pricing models

Vaneezeh Siddiqui is an Investor at Thomson Reuters Ventures. Thomson Reuters Ventures is an early-stage corporate venture firm. They invest in companies at the seed and series A stages building in tax, legal, fraud, risk, compliance, insurtech, and fintech. Takeaways -Breaking into VC early in her career through Front Row Ventures and other experiences. -What makes Thomson Reuters Ventures unique with their thesis, average check size and stage. -Building credibility and trust with a founder when you an earlier career VC. -Building relationships internally to make sure a deal gets done. -The VC and tech ecosystem in Toronto versus NYC. -There is a need for more resources and thought leadership in the venture capital industry, especially for those interested in breaking into VC. Chapters 00:00 First Exposure to Venture Capital 07:00 Focus on What You Care About 13:56 Thomson Reuters Ventures: Series A Focus 26:37 Moving Deals Forward 37:30 Investment Focus Areas 45:23 Advice for Aspiring VCs Keywords venture capital, exposure, innovation, entrepreneurship, business, tech, software development, Front Row Ventures, pre-seed, student-led, investing, Ripple Fellowship, founders, investors, relationships, research, industries, venture capital, building rapport, moving deals forward, Toronto vs New York, investment focus areas, supporting aspiring VCs, mentorship, community, resources, thought leadership, personal goals, professional goals, advice