My guest today is Dave Yuan. Dave is the Founder and Partner of Tidemark Capital, which he started in 2021 after 15 years as a General Partner at Technology Crossover Ventures. Dave has been investing in vertical market software as long as anyone I know and he currently sits on the board of two VMS businesses, Toast and Karbon. He is the perfect guest to deliver a primer on VMS, which is exactly what we do in this episode. Please enjoy my conversation with Dave Yuan. The Vertical SaaS Knowledge Project - Tidemark Capital Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here.  ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:57) - (First question) - Vertical Market Software (VMS) offers unique business models and customer benefits (00:04:02) - Industry-specific software serving SMBs with tailored functionality (00:06:53) - Assess market based on TAM, competition, and growth dynamics (00:10:00) - Trust as a nuanced factor in evaluating market opportunities (00:11:59) - Leverage account-based marketing and local network effects for VMS solutions (00:14:22) - Vertical solutions offer tailored value and quick results for specific industries (00:16:21) - Disrupting legacy control points through integration and surrounding functionality (00:19:07) - Building demand is crucial for small merchants (00:21:31) - VMS entrepreneurs need operational experience and multi-product mindset (00:23:13) - Investors need to adapt to the specific growth stage and market dynamics (00:25:22) - Gross retention is driven by control points, individual-based retention, and distribution (00:29:43) - Multi-product vertical SaaS: Integrated solutions for efficiency and value (00:32:33) - Diverse offerings to serve merchants' needs in a multi-product approach (00:34:07) - FareHarbor's unique strategy led to success in the tour industry (00:38:43) - LA-based company revolutionized commercial casting with a free software tool (00:40:03) - Opportunities remain in VMS, with greenfield areas and specific markets (00:45:12) - Key valuation considerations for VMS businesses (00:47:27) - Time horizon is crucial for investing in VMS businesses (00:48:04) - Businesses worth studying in this category (00:51:12) - The kindest thing anyone has ever done for him