The Gregory and Paul Show

On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Guest Links Court Lorenzini - Founding CEO of DocuSign Website – https://nexusfounders.com/ LinkedIn: – https://www.linkedin.com/in/court-lorenzini-333447/ Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – https://www.linkedin.com/in/gregorykennedy/ X (Twitter) – https://twitter.com/gregorykennedy Paul Website – https://karmic.buzz LinkedIn – https://www.linkedin.com/in/pxue/ X (Twitter) – https://twitter.com/pxue =================================================== ️ Episode 025 – How DocuSign Was Really Built, with Court Lorenzini This episode goes deep into the origin story of DocuSign, how court cases and real estate distribution unlocked product market fit, why founders must be adaptable, the flaw in most hiring frameworks, and where AI cycles are headed. Court also breaks down why the best startup advice comes from founders, not investors, and why the future of education may return to apprenticeships. Highlights ☕ Opening Banter and Housekeeping (0:00) Gregory and Paul kick off late but caffeinated, talk about YouTube growth, the Spotify upload delay, and why five listeners still count as momentum. ️ Court’s Founder Origin Story (2:00) Court grew up inside the earliest days of Silicon Valley. His father invented the commercial process for growing silicon and helped launch the Band of Angels. The legends of the Valley were just family friends. From age fourteen, Court carried notebooks filled with observations about leadership, products, and decision making. He reviewed them twice a year for two decades. Those notebooks became the foundation for his founder career. ️ How DocuSign Really Started (7:00) DocuSign began when Court partnered with Tom Gonzer, who had acquired leftover IP from a failed company. The assets included the DocuSign name and a patent for internet-based signatures. Court bought the assets, Tom quit his job, and they built the original business plan together. ⚖️ The Legal Breakthrough That Changed Everything (11:00) Enterprise buyers loved the idea. Their chief legal officers refused to approve it. Court hired a judge, a jury, and attorneys to retry a real document-fraud case as if it were executed with DocuSign. The judge ruled not only that the signature was defensible, but that it produced more evidence than ink signatures. That opinion became their proof. Microsoft Enters the Chat (15:00) Microsoft discovered DocuSign organically through internal .NET demos. Their deputy CLO called Court directly and asked to become a customer. In 2003 that endorsement was seismic. Legal officers at other enterprises finally relaxed. The Realtor Distribution Superpower (16:50) The National Association of Realtors embedded DocuSign into its transaction software. Three million realtors used it. Every homebuyer used it. Every homebuyer also had a day job. The product jumped from real estate into every major industry. This was the product market fit moment. Zero to One Lessons for Founders (22:00) Court says the early stage requires creativity and adaptability. There is no playbook. Founders must search for signals and adjust quickly when evidence changes. Bullheaded conviction without signal usually ends in failure. ️ How He Would Build DocuSign Today (24:00) Modern infrastructure would reduce DocuSign’s original costs by orders of magnitude. AWS replaces physical data centers. LLMs provide reasoning. Teams of three can now build what once required thirty. Founder Nexus and the Power of Lived Experience (27:30) Court shares the biggest lesson of his career. The best advice he ever received came from o... Chapters (00:00:00) - The Gregory & Paul Show(00:01:15) - Courten Lorenzini on Nexus and His Impact(00:02:31) - How I Started Being a Founder: The Very Beginning(00:07:34) - Inventing DocuSign: From Early Startup to Enterprise(00:14:12) - Real Estate Agents on Microsoft's DocuSign Deal(00:18:50) - What was the first moment that the company found product market fit?(00:20:12) - Ideas for the 0 to 1 Snap(00:22:42) - How to Win with Conviction and Adaptability(00:24:01) - What Would DocuSign Do Different in 2003?(00:26:37) - What Lessons Did You Learn From Starting a Startup?(00:30:12) - Finding and Identifying One's Superpower(00:33:11) - The Secret to Realizing Your Superpowers(00:36:23) - Understanding the Dark Side of Superpower(00:38:03) - What's Your Secret to Success?(00:40:51) - Will the AI Hype Cycle Continue?(00:44:01) - On the Future of Crypto Coins(00:45:14) - All About Crypto(00:46:36) - Immigration and the Future of Jobs(00:50:56) - In the Elevator With Founder Nexus(00:52:20) - How Do Founders Get Involved at Founder Nexus?(00:55:08) - Any final words or stuff you'd like to close with or leave with our audience