My guest today is Court Lorenzini, the co-founder of DocuSign and a true serial entrepreneur. This conversation was absolutely packed with insights, and I’m so excited to share it with you all. Court’s journey, from his early days in engineering to building DocuSign into the powerhouse it is today, is truly inspiring. We delved into everything from the challenges of finding product-market fit to the lessons he learned from both his successes and failures. Trust me, you won’t want to miss this one! So grab a coffee, settle in, and get ready to learn from a true legend in the startup world.
- Guest: Court Lorenzini | Founder of Docusign & Founder Nexux
- Host: Nataraj | Senior PM at Azure, Creator of Startup Project & Angel Investor
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Key Takeaways from this Episode:
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Court’s background and early entrepreneurial ventures
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The genesis and growth of DocuSign, including key partnerships and the secrets to its market dominance
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Court’s exit strategy from DocuSign and the impressive return on investment
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Lessons learned from a spectacular failure (Metabright) and Court’s approach to evaluating new opportunities
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The vision and purpose of Founder Nexus, Court’s latest venture supporting the next generation of founders
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Court’s investment strategies and observations on the current investment climate
Detailed Timestamps and Topics:
Below you’ll find a detailed breakdown of the conversation, allowing you to jump to specific topics that pique your interest.
Early Years & Entrepreneurial Spirit:
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(0:01:246 – 0:35:234): Introduction and welcome to Court Lorenzini.
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(0:40:246 – 1:16:782): Court’s background – Engineering career and early entrepreneurial ventures.
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(1:50:102 – 2:05:838): Cisco’s impact on fostering successful entrepreneurs.
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(2:05:838 – 3:30:004): Court’s early company-building approach and his five-year exit strategy.
The DocuSign Story:
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(3:34:004 – 5:06:042): The birth of DocuSign: Original idea, IP acquisition, and the name’s origin.
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(5:06:042 – 6:35:318): DocuSign’s journey to product-market fit – a slow grind and long-term vision.
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(6:35:318 – 9:46:848): Key early customers: Microsoft and the National Association of Realtors – the power of strategic partnerships and inbound vs. outbound sales.
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(9:46:848 – 11:22:828): DocuSign’s continued market dominance and the competitive landscape.
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(11:22:828 – 14:07:594): The core reasons for DocuSign’s success: human preference for consistency and robust APIs.
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(14:51:042 – 16:02:894): Court’s exit from DocuSign and the remarkable ROI.
Beyond DocuSign: Failures, Lessons, and New Ventures:
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(16:10:026 – 17:12:088): Court’s subsequent ventures, including a successful renewable energy company and Metabright.
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(17:12:088 – 20:46:198): Analyzing Metabright’s failure and the valuable lessons learned.
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(20:46:198 – 23:48:586): Court’s methodology for evaluating new opportunities – validating and actively trying to kill ideas.
Founder Nexus: Supporting the Next Generation:
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(23:48:586 – 25:01:294): Introducing Founder Nexus – a unique approach to supporting founders.
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(25:01:294 – 27:25:304): The vision and purpose of Founder Nexus: increasing the odds of success for venture-scale founders.
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(27:25:304 – 28:15:446): The mathematical model of startup success and how Founder Nexus aims to improve each variable.
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(28:15:446 – 29:27:704): Comparing Founder Nexus to communities like Hampton and Offline, and the importance of curation.
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(29:27:704 – 31:18:678): Founder Nexus’s unique community-building approach: focusing on lived experience and ongoing learning.
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(31:18:678 – 33:26:323): The structure and format of Founder Nexus events.
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(33:26:323 – 35:07:126): Traction and future plans for Founder Nexus: expansion beyond Seattle and global reach.
Investments & Insights:
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(35:07:126 – 37:08:072): Court’s approach to investing in venture funds – focusing on early-stage and non-traditional funds.
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(37:08:072 – 37:45:686): Observations on the outperformance of women-run funds.
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(37:45:686 – 40:36:635): Thoughts on valuations and the current investment climate.
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(40:41:270 – 42:06:304): Court’s personal investment strategies.
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(42:17:110 – 43:56:438): The surge in bio and energy companies in Seattle during the Obama administration.
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(44:07:934 – 46:20:299): The impact of Court’s three master’s degrees on his career.
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(46:36:566 – 48:25:076): Current reading and listening – books and podcasts influencing Court’s thinking.