#87 DocuSign Founder on Building $16B Company | Court Lorenzini

Guest: Court Lorenzini | Founder of DocuSign & FounderNexus Host: Nataraj | Senior PM at Azure, Creator of Startup Project & Angel Investor Subscribe to Startup Project Newsletter for valuable founder insights: https://startupproject.substack.com/ Join Nataraj in conversation with Court Lorenzini, co-founder of DocuSign and serial entrepreneur, as they delve into the world of startups. Court shares his incredible journey, from early engineering roles to leading DocuSign to its multi-billion dollar company. **Timestamps & Topics:** * **00:01:246 - 00:35:234:** Introduction and welcome to Court Lorenzini. * **00:40:246 - 01:16:782:** Court's background – Engineering career and early entrepreneurial ventures. * **01:50:102 - 02:05:838:** Discussion about Cisco's impact on fostering successful entrepreneurs. * **02:05:838 - 03:30:4:** Court's entrepreneurial journey: Early days of building companies and his approach to exiting around year five. * **03:34:004 - 05:06.042:** The genesis of DocuSign: Original idea, acquisition of IP, and the name's origin. * **05:06.042 - 06:35.318:** DocuSign's journey to product-market fit – a slow grind and long-term vision. * **06:35.318 - 09:46.848:** Key early customers: Microsoft and the National Association of Realtors – how these partnerships propelled DocuSign's growth and the importance of inbound vs outbound sales. * **09:46.848 - 11:22.828:** DocuSign's continued market dominance – exploring the reasons behind its success and the competitive landscape. * **11:22.828 - 14:07.594:** The core reasons for DocuSign's success: human preference for consistency and robust APIs for data integration. * **14:51.042 - 16:02.894:** Court's exit strategy from DocuSign and the incredible return on investment. * **16:10.026 - 17:12.088:** Court's ambition and his subsequent ventures, including a successful renewable energy company and a spectacular failure (Metabright). * **17:12.088 - 20:46.198:** Detailed analysis of Metabright’s failure and the lessons learned. * **20:46.198 - 23:48.586:** Court’s methodology for evaluating new opportunities – validating the idea and actively trying to kill it. * **23:48.586 - 25:01.294:** Introduction to Founder Nexus – a unique approach to supporting the next generation of founders. * **25:01.294 - 27:25.304:** The vision and purpose of Founder Nexus: increasing the odds of success for venture-scale founders. * **27:25.304 - 28:15.446:** The mathematical model of startup success and how Founder Nexus aims to improve each variable. * **28:15.446 - 29:27.704:** Comparison with similar communities like Hampton and Offline, and the importance of community curation. * **29:27.704 - 31:18.678:** Founder Nexus's unique approach to community building – focusing on lived experience and ongoing learning. * **31:18.678 - 33:26.323:** The structure and format of Founder Nexus events – short forums and rotating groups. * **33:26.323 - 35:07.126:** Traction and future plans for Founder Nexus – expansion beyond Seattle and the goal of global reach. * **35:07.126 - 37:08.072:** Court’s approach to investing in venture funds – focusing on early-stage, and often non-traditional funds. * **37:08.072 - 37:45.686:** Observations on the outperformance of women-run funds. * **37:45.686 - 40:36.635:** Thoughts on valuations and the current investment climate – focusing on early-stage deals and late-stage pre-IPO opportunities. * **40:41.27 - 42:06.304:** Court's personal investment strategies – both early-stage and late-stage pre-IPO investments. * **42:17.11 - 43:56.438:** Discussion about the surge in bio and energy companies in Seattle during the Obama administration. * **44:07.934 - 46:20.299:** Court’s decision to pursue three master's degrees and their impact on his career. * **46:36.566 - 48:25.076:** Current reading and listening – books and podcasts influencing Court's thinking.