Podcast
The Gregory and Paul Show
Hosted by The Gregory and Paul Show · EN
We break down the latest in tech, AI, and startups live every Thursday at 11:00 AM Pacific and 2:00 PM Eastern on X, LinkedIn, and YouTube.
10episodes
Episodes
Newest firstAll episodes
035 AI Hacking, Market Panic, and AI War Games
Feb 2700:52:46Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →034 Clawdbot MANIA with Alexandra Naomi Perez, COO of Thrad
Feb 1301:02:49Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →033 OMG Saas-pocalypse!
Feb 600:59:10Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →032 Special Guest Ross Simmonds from Foundation Marketing
Jan 3000:56:43Tap to summarizeConnect with Ross Website – https://foundationinc.co/ LinkedIn – / rosssimmonds X (Twitter) – https://x.com/TheCoolestCool Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →031 Will Vibe Coding Make Software Free?
Jan 2301:03:31Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →030 OpenAI Ads, Apple's Gemini Deal & Elon's Dilemma
Jan 1600:57:05Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →029 A16Z 15B fund, AI reality checks, and why Bowie was right
Jan 901:02:41Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →028 Somalia Fraud and Billionaires Taxes in CA
Jan 301:09:59Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →027 With Special Guest Arjun Dev Arora
Dec 2001:00:54Tap to summarizeOn the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is fighting about this week. Connect with Gregory & Paul Gregory Kennedy Website – https://www.vibeyoursaas.com LinkedIn – / gregorykennedy X (Twitter) – / gregorykennedy Paul Website – https://karmic.buzz LinkedIn – / pxue X (Twitter) – / pxue
Transcribe →025 Special Guest Court Lorenzini, Founding CEO of DocuSign
Dec 500:55:55Tap to summarizeOn 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 other founders. The worst came from investors who had never built companies. Founder Nexus was created to solve this gap by connecting venture-backed founders in global peer groups. Understanding Superpowers (30:00) Court explains his Superpower Analysis framework. Myers-Briggs and strength tests do not predict performance. What Happens Next in AI (41:00) LLMs will commoditize. Application-layer companies will become the real winners. Hardware and model providers will fade into the background. T Where Founder Nexus Is Heading (52:00) Chapters are expanding to San Francisco, London, Tokyo, and beyond. Members must be venture-scale founders, have professional funding, and be building toward at least $100M in annual revenue.
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