There are fewer than 400 public tech companies worth over $10 billion. DocuSign is one of them — but its success wasn’t driven by flashy tech or perfect timing. In this episode, DocuSign founder Court Lorenzini breaks down the non-obvious decisions that actually bent the curve: • Why pricing and packaging mattered more than product features • How competing with FedEx and fax machines shaped DocuSign’s business model • The legal roadblock that almost stopped adoption — and the unconventional solution • Why focus beats scale in the early days • The real reason most venture-scale companies fail (hint: it’s the founders) We also dive into Founder Nexus — Tom’s answer to repeat founder failure modes — and why shared experience, not advice, is the real unlock for building enduring companies. This is a masterclass in decision-making, positioning, and surviving the brutal realities of venture-scale entrepreneurship. Timestamps: 00:00 – Why DocuSign Matters 05:20 – The Decision That Bent the Curve 11:00 – Competing With Fax & FedEx 17:40 – The Legal Problem That Almost Killed Adoption 24:30 – The Microsoft Moment 29:10 – Why Real Estate Was the Beachhead 35:45 – Why Most Startups Actually Fail 41:50 – The Success Equation 48:30 – Founder Nexus & Shared Scar Tissue 54:40 – The Contrarian Take on Education & AI Find Court Lorenzini online at: LinkedIn: https://www.linkedin.com/in/court-lorenzini-333447/ Twitter: https://x.com/FounderNexus FounderNexus: https://foundernexus.com This episode is sponsored by EmergeOne, fractional CFOs for venture backed tech startups from Seed to Series B. Get in touch at https://emergeone.co.uk/contact-us/ or join the CFO team at https://emergeone.co.uk/join-the-cfo-team/ Sign up for EmergeOne’s weekly newsletter, Off Balance at https://off-balance.beehiiv.com/subscribe Hosted by Simplecast, an AdsWizz company. See https://pcm.adswizz.com for information about our collection and use of personal data for advertising.