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

Chapters

• (00:00:00) - Getting Out of the Clutter
• (00:00:20) - Back from Vacation With Gregory and Paul
• (00:01:51) - The Fight for AI Safety
• (00:02:28) - How To Write a Good Show Notes With AI
• (00:05:19) - Claude Apparently Hacked Mexico
• (00:09:43) - Was Cybersecurity More Advanced Than Ever?
• (00:10:44) - The Sub-Stack Memo
• (00:16:21) - Citadel Investment Firm Rejects the AI Doomsday Narrative
• (00:21:45) - WSJD Live: Do You Know What's Happening In the
• (00:24:19) - Jack Dorsey: Block Needs to Let Go of 4,000
• (00:27:49) - Jack Dorsey's Layoffs and SaaS Sales
• (00:30:54) - Perplexity Computer: The Future of Digital Working?
• (00:35:42) - Robot-based AI: The Challenges
• (00:38:19) - Elon Musk on His Meme
• (00:39:45) - This Hardware AI Model Can Speed Up Your Chat
• (00:43:53) - AI Decides to Use Nuclear Weapons in 95% of War Games
• (00:48:08) - Producer Claude: Hacking entire country
• (00:49:31) - Two More Events Announced for Tech Founders
• (00:52:30) - A Taste of Broadway

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

Chapters

• (00:00:00) - Cloudbot: The AI Startup to Watch
• (00:01:30) - In the Elevator With Tech Guys
• (00:02:40) - Openclaw: Setting Up a Mac Mini
• (00:06:07) - Claudebot: Setting up a social network
• (00:07:42) - Claudebot: Does the term still exist?
• (00:08:54) - Robot on Reddit
• (00:09:47) - Claudebot: What does it do?
• (00:14:43) - Codbot integration into my Cloud
• (00:20:48) - How to Start a Cloud Bot in the US
• (00:25:01) - Zapier's Security
• (00:27:14) - A16Z Has Already Offered Reddit's Creator A Billion Dollars
• (00:31:54) - AI Cloudbot: Too Many Steps to Join
• (00:36:06) - Automation vs. AI in Marketing
• (00:41:36) - Advertisers: More Data Does Not Make It More Effective
• (00:43:33) - "This article is hyperbolic," says Grok
• (00:46:15) - The SaaS Apocalypse
• (00:50:04) - Real Estate Agents vs Travel Agents: Which Is Better?
• (00:51:16) - Will AI Hurt the Job Market?
• (00:57:15) - Will the AI Disrupt the Old Industry?
• (01:01:30) - Startup Pitch Competition and Mixer in San Francisco

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

Chapters

• (00:00:01) - SaaS Stocks Get Crushed
• (00:03:54) - SaaS Apocalypse: AI Is Killing SaaS
• (00:05:55) - The Threats From Above and Below
• (00:11:18) - SaaS Stocks Rerated
• (00:14:32) - Will Software Companies Replace Their Subscriptions?
• (00:16:04) - Reasons for the SaaS Apocalypse
• (00:16:58) - AI Boom and How Real Is It?
• (00:19:32) - Trump on 3-D Printer Regulation
• (00:24:26) - Robots and the revolution in AI
• (00:27:00) - The AI Assistant's Bigger Picture
• (00:30:54) - Is AI Stupid for the Average Person?
• (00:32:07) - Cloudbot: An AI Trading Bot
• (00:36:11) - Claudebot: An LLM in a Loop
• (00:39:30) - Claudebot: The First Assistant
• (00:40:12) - Claude the Bot Creates a Reddit Social Network
• (00:45:47) - Adam Levine: AI Is Already Everywhere
• (00:51:16) - Will AI Fragile the Internet?
• (00:52:35) - Three Nerds With Glasses
• (00:55:48) - A Pitch Competition for Startups

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

Chapters

• (00:00:01) - Ross Simmons On The Gregory & Paul Show
• (00:00:58) - Ross Simmons on How He Started His Content Marketing
• (00:02:23) - Ross Simmons: On Diversifying His Career
• (00:06:03) - How Brandon Simmons Started a Marketing Agency in Canada
• (00:10:25) - In the Elevator With Hustle and Grind
• (00:16:03) - Have You Got a Personality in Your Office?
• (00:16:35) - Geo-Topics in the World
• (00:17:08) - SEO for Electricians: The New Era
• (00:22:25) - How to Manage Content Marketing in a Startup
• (00:24:58) - How to Get Your Content Out There
• (00:27:35) - Will We See More Fake AI Video Content in 2021?
• (00:33:22) - Are We Ready for AI-generated Ads?
• (00:37:47) - Is AI Influencers Bad For You?
• (00:41:15) - The Most Overrated Thing in Marketing
• (00:46:51) - Will YouTube Go Mainstream?
• (00:47:52) - What Marketing Tactics Do You Think Are No longer Effective?
• (00:49:41) - Are Infographics Coming Back on LinkedIn?
• (00:51:16) - Ross: How to Get Educated in Marketing
• (00:53:51) - The #1 Worst Mistake Startup Founders Make
• (00:56:17) - Fooled by the Internet

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

Chapters

• (00:00:01) - Gregory and Paul
• (00:01:02) - The Llama Lounge in San Francisco
• (00:02:08) - This AI Startup Event Has Big Companies Invited
• (00:04:31) - Machine Learning and the Circuit Board
• (00:10:07) - OpenCode vs. Cursor: Can AI Compete With Dev
• (00:14:18) - Vibe Coding in the AI Revolution
• (00:16:01) - Can Software Cost Zero in the Future?
• (00:22:25) - Intel CEO: There's Demand for Next-Gen Chips
• (00:25:52) - Vizient Create
• (00:27:24) - How to make a viral video
• (00:29:18) - TikTok to Create an American Joint Venture
• (00:33:06) - Sam Altman Melts Down With Sequoia's Business
• (00:34:14) - Amazon's Rufus AI Shopping Tool
• (00:39:35) - The New X Algorithm
• (00:44:02) - Twitter's New Year's Eve Stable
• (00:48:00) - Alex Jones on the Algorithms
• (00:48:33) - Silicon Valley: Valuation and Return of Money
• (00:54:34) - Is AI Valuation Too High for Figma?
• (00:58:48) - Will AI Impact Uber's Bottom Line?
• (01:03:14) - Dr. Oz

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

Chapters

• (00:00:01) - The Fight for Autism
• (00:00:09) - How We're Doing on YouTube & Spotify
• (00:01:03) - OpenAI Announcement: Chat to Me $8 a Month
• (00:07:20) - Will Chat Lead to Adult Content?
• (00:13:45) - AI Ads for the Super Bowl
• (00:16:41) - Apple Partners with Google in AI
• (00:21:55) - What Holds Back the AI Headset?
• (00:26:05) - Apple's Siri partnership with Google
• (00:27:06) - Google's Personal Intelligence Rollout
• (00:29:12) - Google's Universal Commerce Protocol Announcement
• (00:34:59) - How to Sign Up to e-commerce sites with a single login
• (00:37:08) - Tesla's Five Year Stock Chart
• (00:37:28) - Tesla Merger: Do I Still Buy the Stock?
• (00:44:21) - On Twitter's Algorithms
• (00:47:40) - The Metaverse Layoffs
• (00:52:31) - I Buy the Narrative About Argentina
• (00:54:15) - How to Orchestrate Agents in a Real-Time CRM

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

Chapters

• (00:00:01) - The Dark Knight
• (00:00:07) - The Gregory & Paul Show
• (00:04:19) - A 16Z Fund Raising $15 Million
• (00:09:33) - Venture Capital's Return on Capital
• (00:11:02) - A16Z: The VCs' Focus on Winners
• (00:14:20) - Marc Andreessen on The Open Web and Venture Capital
• (00:19:39) - The Founder CEO Is Like Napoleon
• (00:24:10) - Buffett on Microsoft's Early-Stage Investments
• (00:25:13) - WSJD Live: The AI Adoption 2026
• (00:30:48) - The Need for Open-Source Coding
• (00:36:42) - Can Grammarly Replace Writing?
• (00:41:25) - Will AI Replace Human Communication?
• (00:45:36) - How Much Context Matters in a Message
• (00:46:34) - California exit tax debate
• (00:47:00) - California Tech Workers Are Moving to Utah
• (00:51:28) - California's high fire risk
• (00:54:17) - If You Want to Leave California, Do Your Own Research
• (00:57:20) - David Bowie
• (00:57:46) - David Bowie: The Internet Will Be Autonomous
• (01:02:32) - A Taste of Psych

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

Chapters

• (00:00:00) - Happy New Year!
• (00:00:09) - Gregory & Paul: Moving Is Terrible
• (00:03:23) - Winds whistling in the condo
• (00:04:03) - I Got Brutally Sick On A Holiday Trip
• (00:05:45) - Somali Daycare Fraud
• (00:09:21) - Will financial fraud continue in the US?
• (00:15:51) - Daycares on the Frauds
• (00:19:33) - Citizen Journalism and the Rise of Collectivism
• (00:22:59) - Should Chinese AI Companies Move to the US?
• (00:28:42) - American companies diversify their operations in China
• (00:36:47) - Billionaire Tax on Tech billionaires
• (00:38:20) - California's Billionaire Tax
• (00:44:11) - Will Austin Replace San Francisco as the Tech Capital?
• (00:51:41) - Boston vs. Austin on Non-Compete
• (00:53:27) - Tyler Cowen on Texas Stock Exchange
• (00:59:16) - Peter Walker: If High-Tech Talent Move to Austin,
• (01:03:41) - Top Tech Executives on Austin's Fight for Tech Talent
• (01:07:14) - Applications are open for the Startup Meetup in San Francisco

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

Chapters

• (00:00:01) - Gregory & Paul
• (00:02:20) - Tim Ferriss on Starting a Startup
• (00:05:29) - Leading a startup's venture capital journey
• (00:09:27) - What Kind of Founder Traits Do You Look For?
• (00:16:24) - Expo and the St. Francis Foundation
• (00:18:57) - What Kind of Tech Startups Are You Excited About?
• (00:21:04) - Elon Musk's Plan to Build a Data Center in Space
• (00:24:36) - WSJD Live: Early Stage Startup Funding
• (00:27:56) - How to Raise Capital in 2021
• (00:29:20) - The Deck vs. the Presentation
• (00:33:01) - The 3-Slide Teaser and 10-
• (00:34:13) - Cold Outreach vs Warm Intro: What's The Difference?
• (00:36:42) - In the Elevator With AI
• (00:38:25) - How Much Traction Does a Startup Need to Get Funded?
• (00:41:23) - Do You Need an LLC or a C Corp?
• (00:42:30) - Lovable's Expansion Into the Ecosystem
• (00:48:10) - Lovable: The Amateur Platform
• (00:49:24) - Self-Driving Trucks Reject Teamsters Demand
• (00:51:24) - Will Self-Driving Trucks Replace The Driver?
• (00:55:11) - The OpenAI Race to IPO in 2026
• (00:59:39) - The Inside Baseball Meme

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

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

===================================================

️ Episode 024 – How to Scale from Zero to a Million in ARR as a Solo Founder

Gregory and Paul walk through how they both went from solo freelancers to running real businesses. Paul explains how AI nuked his MVP dev agency and pushed him into Reddit marketing just as Google started boosting threads. Gregory breaks down how Vibe Your SaaS went from two experimental clients to a full portfolio by treating services like a product and never stopping the pipeline work. They compare work styles, talk honestly about pricing, churn, and boundaries.

Canadian Thanksgiving, Rice Stuffing, and Vibes (0:00)
They open with Canadian Thanksgiving timing, discuss Asian Canadian families doing rice-stuffed turkey, and why rice plus mushrooms beats bread as stuffing. It sets the relaxed tone before they switch into business mode.

From Layoffs to Freelance Life on Black Friday (1:38)
Gregory explains why this episode is for people who were just laid off or want out of corporate. The theme is simple: how to go from zero to one million in revenue by turning your skill into a freelance agency.

‍ When AI Crashed MVP Dev Pricing (3:17)
Paul tells the story of running a dev agency as GPT 3.5 landed. MVP projects that used to pay one hundred thousand dropped to fifty thousand, then ten thousand, as founders realized they could vibe code an early product instead of hiring a full team.

Pivoting Into Reddit and AEO While Demand Spiked (8:53)
As Google started boosting Reddit in search and more non-Reddit users used it for product research, Paul saw a new opportunity. He had already gone viral with several posts and knew how to write long-form threads that both rank in Google and pull real traffic.

First Clients, Spec Work, and Low Pricing (13:08)
Paul shares exactly how he closed his first Reddit clients. He posted case studies, wrote sample threads on spec, showed screenshots of rankings, and priced the first retainers at around five hundred dollars a month so that saying yes felt easy.

Raising Prices and Managing Ten Clients at Once (17:52)
Once demand picked up, he pushed retainers toward one thousand to one thousand five hundred per month and ended up with about ten clients paying six to seven thousand total. It was enough to live on but a lot of work, which forced him to confront his capacity and start raising prices again.

Two Different Ways to Run the Week (26:10)
Gregory and Paul compare operating styles. Gregory lives by a structured calendar with specific days for calls, content, and in-person meetings, and even blocks Fridays as founder time. Paul works from a short daily list of two or three must-do tasks and accepts that everything else is chaos.

Productized Services vs One-Off Projects (32:04)
They explain why repeatable work beats one-time projects if you want a real business. Design sprints, websites, and random one-offs churn fast. Content, social, and ongoing go-to-market support can be packaged as a monthly service that compounds over time.

Pricing Bands and the Path to One Million (36:40)
Together, they map out the math. Most healthy retainers sit between one thousand and eight thousand a month, where hiring a contractor is still cheaper than a full-time hire. With productized services and clean delivery, twenty to thirty clients at those levels get you to a million in annual revenue.

Low Ticket Churn, High Ticket Calm, and Letting Go (...

Chapters

• (00:00:01) - Asian Canadians Talk About Canadian Thanksgiving
• (00:01:35) - Black Friday: How to Start a Business
• (00:02:28) - How to Have Your Own Software Development Agency
• (00:06:27) - How to Integrate Development into Your Marketing Business
• (00:07:25) - Pushing the Shift into Marketing
• (00:08:48) - How to get your Reddit post indexed in Google
• (00:12:14) - How to get your content on Reddit
• (00:16:03) - How to start a business on the Internet
• (00:20:18) - How to get a startup to close with low pricing
• (00:21:10) - 8 Steps to Finding a Job
• (00:22:40) - How to sustain yourself with low-paying work
• (00:24:22) - How to Balance Marketing and Sales
• (00:26:28) - How to Manage Your Time on Reddit
• (00:29:48) - How To Stay Organized At Work
• (00:31:34) - How to Scale Your Business From Start to Finish
• (00:37:30) - How Do You Productize Your Services?
• (00:39:08) - Tim Ferriss: From Ultra-Custom to Templated
• (00:45:01) - Can You Do a Million-Dollar Contractor Business?
• (00:52:18) - How to Scale Your Business: Brand and Trust
• (00:54:33) - Vibers: A Community Product, Founder First
• (00:56:31) - VIBM VC Founder Mixer: AWS as a Sponsor
• (00:59:32) - Stripe Bans My Account For Joking
• (01:01:18) - Dancing with the Pope

This episode covers Gregory’s near-breakup with X, how the algorithm quietly fixed itself, Skillprint’s mind-mapping technology, the link between games and cognition, why self-awareness might be the whole point of life, the rise of performance psychology in esports, and the internet’s obsession with Bill Ackman’s pickup line.

Gregory’s Algorithm Detox Story (0:00)
Gregory opens with a confession. During the election era, he stayed on X the way a smoker stays on Marlboros. Everyone else quit. He kept scrolling through the MAGA slop feed until Nikita joined and saved the platform and brought tech back into the timeline. Paul reacts with pure disbelief that he once hosted an X workshop nobody attended.

Meet Chethan: Neuroscience Meets Gameplay (2:04)
The guys introduce Chethan Ramachandran, CEO and cofounder of Skillprint. He blends AI, neuroscience, and gameplay to measure the mind through micro interactions. Gregory gives him the full G&P Show intro. Chethan jokes that he wants Gregory to introduce him everywhere from now on.

Growing Up In Silicon Valley Before Silicon Valley Was Silicon Valley (3:41)
Chethan tells the wild origin story. Cherry orchards. Danger’s Sidekick. Andy Rubin was predicting the app store years before the iPhone existed. A high school with a nuclear shelter, Woz used to prank call world leaders. Pure early SV lore.

Machine Learning Before Machine Learning Had A Name (8:05)
Chethan describes being pulled out of investment banking by a UBS exec who wanted to apply early ML techniques to security. This leads to a first startup acquisition. Then, a second startup applying algorithms to games. Eventually, Unity buys the company. Games become the perfect medium for psychological measurement.

Why Games Reveal Who You Are Better Than Surveys (13:22)
Skillprint uses decades of neuroscience to understand people through the way they play. Gameplay patterns reveal mood, cognitive habits, and personality traits with surprising accuracy. Focus, flexibility, task switching, creativity, and even stress responses show up in the tiny choices a player makes. Gregory and Paul are stunned that something as simple as a timer in a game can tell you more about a person than a traditional personality test.

The Philosophy: Self Awareness As The Point Of Life (31:31)
The conversation drifts into a deeper lane. Chethan talks about consciousness, plasticity, and how the mind and the brain shape each other. Paul brings in his infinite games framework and makes the case that change is built into human behavior. Chethan expands on why mood shifts quickly, cognition evolves over seasons, and personality moves slowly over time. Gregory adds a story from a neuroscience conference in Aspen about consciousness being a fundamental part of the universe, not just a biological glitch.

Skillprint Today: Esports Partnerships And Real World Impact (47:02)
Skillprint now powers cognitive profiling and mood mapping across esports leagues, wellness apps, training platforms, colleges, and clinics. Developers can embed the SDK to understand their users, personalize experiences, and deliver better emotional outcomes. Esports companies love the performance layer. Health orgs use it to understand behavioral patterns. It is a next-generation training system.

The Big Question: Do People Change? (51:40)
Chethan says people absolutely change, just on different timelines. Mood shifts fast. Cognitive patterns evolve over longer cycles. Personality moves slowly but does move. Habit ties those layers together, play helps surface what is happening, and awareness is what makes any of it stick.

Meme of the Week: “May I Meet You” (57:28)
Bill Ackman accidentally posts dating advice. The internet detonates. Founders test the line in cold outreach. Gregory imagines using it...

Chapters

• (00:00:00) - "I Quit X After the Election"
• (00:01:31) - Gregg & Paul: Memes & Startup Talk
• (00:03:25) - How I Started a Startup in Silicon Valley
• (00:07:37) - Andrew Rubin on Machine Learning and the Early Mobile
• (00:12:18) - How Social Media Can Tell You How to Play
• (00:17:34) - Does Bingo Make You More Active?
• (00:23:17) - Inflation and the psychology of games
• (00:24:17) - In Infinite Games: The Transference of Mind
• (00:29:05) - On Plasticity and Regenerative Theory
• (00:30:04) - Understanding the mind and the brain
• (00:32:08) - Paul Feist on Consciousness
• (00:37:51) - Understanding the Mind Through Playing Games
• (00:43:01) - Mind Games: The Trail Making Task
• (00:47:09) - Mysterious Brands on Partnering with Esports Companies
• (00:51:17) - How to Win with Self-Help?
• (00:53:42) - How Should Companies Monitor Behavior Change?
• (00:57:00) - We're Out Of Time
• (00:57:10) - Meaning of the Meme for the Week
• (00:57:32) - Twitter went bonkers with this pickup line from billionaire Bill Ackman
• (01:00:46) - What Is The Challenge of Commuting In San Francisco?
• (01:01:59) - What's the Rent in Toronto?

Guest Links

Charlie Light – X Ghostwriting Expert
X (Twitter) – / chasedownleads
X (Twitter) – / cokedupoptions
X (Twitter) – / huntercoldcalls
LinkedIn: – / charlielight

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

️ Episode 021 – The Future of AI Advertising with Thrad CEO Andrea Tortella

On this episode of the Gregory and Paul Show, the duo welcomes Andrea Tortella, CEO and co-founder of Thrad, an AI-native ad platform redefining marketing inside LLMs and chatbots. Together they break down how chat-based advertising works, why OpenAI’s upcoming ad network could be bigger than Google’s, and what it means for brands and agencies everywhere.

Episode Highlights

️ From London to San Francisco (0:00)
Andrea joins live from San Francisco after relocating from London. The crew talks city vibes, early SaaS days in Soma, and why SF still pulls tech founders back.

Introducing Andrea Tortella and Thrad (3:00)
Andrea shares how Thrad enables brands to advertise inside chat experiences — reaching users as they engage with AI apps. His background includes Perplexity AI, the Aspen Institute, and UCL.

The OpenAI Ad Network Is Coming (6:00)
Andrea predicts OpenAI will soon launch the largest ad business in history, democratizing reach for niche advertisers through conversational prompts instead of keywords.

How AI Advertising Works (8:50)
Ads appear as sponsored chat messages within the LLM interface — native, contextual, and conversational. The goal: ads so good they add value, not distraction.

⚙️ Creative Automation with AI (13:45)
Thrad auto-generates ad copy based on user context and brand parameters in real time. Advertisers can preview and approve AI-generated creatives before launch.

A New Era for Brand Voices (17:00)
Gregory and Andrea discuss how brands can build personality-driven AI personas to chat directly with customers. Luxury brands and challenger brands alike can finally scale 1:1 conversations.

Measuring Success: Beyond Clicks (20:00)
Thrad experiments with new metrics like Cost Per Turn and Attention Shift, measuring conversation quality instead of clicks — a leap beyond CPM and CPC models.

The End of the Click Economy (25:00)
As users move from blue links to chat, traditional metrics lose power. Andrea explains how conversational engagement will become the new marketing currency.

Attention Shift: The Real Metric (27:30)
Thrad tracks topic change before and after ads — proof of genuine influence. Gregory compares it to the golden age of magazine advertising, now reborn inside chatbots.

️ Building at the Speed of Thought (22:00)
Thrad claims the world’s fastest campaign setup: from idea to live ad in seconds. Gregory calls it “vibe marketing for AI.”

Advertising in the Age of AI (33:00)
Andrea and the hosts discuss how chat-based engagement will reshape storytelling, brand education, and customer relationships.

Data Centers in Space (39:00)
The crew dives into Google’s new plan to build solar-powered data centers in orbit. Paul jokes about the GPUs melting. Gregory says it’s classic “moonshot Google.”

Tim Draper Calls OpenAI the AOL of AI (44:00)
Tim Draper echoes Gregory’s long-held view that OpenAI is the AOL or Yahoo of this era — massive, early, but destined to fragment.

Cluey’s Pivot to Note-Taking (47:00)
Gregory and Paul dissect the Cluey controversy: from edgy “cheating app” to serious note-taker. Andrea argues it’s a micro-pivot; Gregory says brand trust is the real issue.

Icon.com Becomes a Creative Agency (55:00)
Another AI startup pivots to human-led creative. The group debates whether AI ad builders can ever outperform real marketers.

Stripe Startup Data (58:00)
US startups are pulling ahead — even without AI. Gregory and Paul debate whether this means AI is less revolutionary than hype suggests.

Meme of the Week (1:01:00)
Gregory debuts two new memes:...

Chapters

• (00:00:00) - How to Start a Business in San Francisco
• (00:01:04) - Live Stream: The Oscars
• (00:01:35) - Greg & Paul: Take Us on the, on the Go
• (00:03:08) - How We Met Andrew Tortella
• (00:04:19) - Andrea Tortella on AI-based Advertising
• (00:05:07) - Bill Gates on OpenAI Ad
• (00:08:45) - OpenAI on Advertising in Chat
• (00:13:50) - How Advertising Is Being Automated by AI
• (00:15:55) - Will There Be a Native Advertising Agency for the Future?
• (00:19:58) - How Advertising on AI is Being Sold
• (00:23:13) - The New Channel: Measurement, Attribution, Money
• (00:25:03) - How to monetize the AI world
• (00:27:24) - Focus on the Attention Shift
• (00:30:19) - Quantifying the Attention Shift
• (00:33:58) - Incentivization of the LLM
• (00:35:54) - OpenAI's Attention Shifting Strategy
• (00:39:06) - Technical Difficulty with Data Centers in Outer Space
• (00:39:31) - Google Will Be Launching Data Centers in Space
• (00:44:24) - Tim Draper: OpenAI Is the AOL of AI
• (00:46:27) - OpenAI Announces 1 Million Customers Working With the AI
• (00:47:13) - Clulee's Pivot to a Note-Taking App
• (00:50:26) - On The Cluley Pivot
• (00:54:59) - Is Icon Turning Into a UGC Creative Agency?
• (00:58:14) - US startups are scaling faster than their peers
• (00:59:36) - US Startup Growth, Non-AI
• (01:01:35) - Socialist Helicopter Evacuation From
• (01:03:24) - A Day in the Life of AI

• (00:00:02) - Back in Toronto after San Francisco
• (00:00:31) - Gregory & Paul: Halloween Special
• (00:03:36) - How To Make A Meme Costume
• (00:06:35) - Amazon's AI Layoffs
• (00:12:10) - Employment Over Hiring: The scapegoat
• (00:16:32) - The Future of AI in Law
• (00:22:35) - This AI SEO Tracking Tool Got Rid of Profound
• (00:26:50) - Nvidia Hits $5 Trillion in Market Cap
• (00:30:53) - Does Mark Zuckerberg Have Any Control Over His Company?
• (00:36:38) - In the Elevator With Tech Founders
• (00:36:51) - He Doesn't Like AI Notetakers
• (00:40:49) - Are We Okay With AI Taking Jobs?
• (00:41:45) - Is He Okay with Neo, the Home Robot?
• (00:45:42) - Ali's 1.2.2 Face Replacing
• (00:49:39) - Brexit and the future of tech
• (00:49:54) - OpenAI to Roll Out Chat-based Ad Network
• (00:54:05) - Is OpenAI the Yahoo of AI?
• (00:56:48) - TikTok Meme: Quoted a Billion-Dollar
• (00:58:07) - Jason Stokes on Apple's CEO
• (00:59:58) - My Pro-Challenging Education Meme

On The Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week.

This week, the duo dives into the great AWS outage, OpenAI’s new browser (and its censorship controversy), and Chamath’s “distribution is king” post. Plus: Reddit vs. Perplexity, 100 ex-bankers training AI, the real cause of the hiring slowdown, and the pain of throwing a San Francisco event during TechCrunch week.

️ Episode 019 – Highlights

Spotify, Shorts, and Growth Everywhere (0:00)
The show is now live on Spotify and Apple Podcasts. Gregory and Paul celebrate passing ten thousand YouTube views and talk about how consistency beats perfection.

Dreamcast Bar Champion (4:10)
Gregory tells the story of beating everyone at a San Francisco bar on Sega Dreamcast while dating his future wife. Paul calls it the ultimate win for tech nerds.

☁️ AWS Outage (5:44)
A massive AWS failure takes down Beehiv, Reddit, and half the internet. Elon jokes on X, and Gregory shares how his newsletter stopped mid-send. Paul imagines Amazon engineers being pulled off their yachts to fix servers.

Chamath on AI Distribution (10:21)
The hosts unpack Chamath Palihapitiya’s viral post on distribution power in the AI era and how Google Gemini is quietly gaining share from OpenAI in enterprise.

Vibe Tools Slowdown (17:04)
Cursor, Replit, and Lovable are losing users fast. Paul says Cursor strikes the right balance for builders. Gregory sticks with ChatGPT because it just works.

OpenAI Atlas Browser (21:18)
OpenAI’s new browser launches to mixed reactions. Gregory questions built-in censorship and raises concerns about free speech in AI tools. Paul argues adults should decide what they can access online.

Reddit vs Perplexity (35:32)
Reddit proves that Perplexity scraped private data and files suit. Gregory calls it an open-and-shut case of data theft. Paul compares it to Google’s early link-sharing battles but notes Perplexity lacks Google’s goodwill.

OpenAI Hires 100 Bankers (41:14)
OpenAI recruits Wall Street talent to train a finance model. Gregory doubts it will replace bankers. Paul sees AI reshaping pay scales rather than eliminating jobs outright.

Jobs, Rates, and AI Myths (43:47)
Gregory argues that the slowdown in hiring is more about interest rates than automation. Paul says entry-level developers and copywriters are feeling the shift first.

The Market Always Corrects (51:42)
Gregory compares the current tech reset to 2001 and 2008. He predicts a decade of retraining, new small businesses, and fewer recruiters per developer.

Meme of the Week (55:27)
An AI meme sums up the moment: chatbots sound confident even when they are completely wrong. Both hosts admit they argue with their AI daily.

️ The San Francisco Mixer (57:22)
Gregory recounts a streak of cancelled venues before landing a Latin Fusion restaurant near Moscone. Over 300 RSVPs, 100 investors, and 200 founders are expected.

☕ Blue Bottle and the SF Mindset (1:03:05)
Paul finally gets to try Blue Bottle coffee. Gregory ends the episode by declaring that San Francisco is not just a city but a state of mind.

Chapters

• (00:00:00) - "Are we live?"
• (00:00:06) - The Gregory & Paul Show
• (00:03:31) - Netflix Star Defends His Video Game Gains
• (00:05:42) - AWS Outage Meme: Elon Takes Shots at AWS
• (00:07:21) - Amazon's AWS Is Down
• (00:10:21) - Distribution in the Age of AI
• (00:11:41) - OpenAI vs. Gemini for Enterprise: Which Is Best?
• (00:15:16) - OpenAI vs. Meta: Can
• (00:20:13) - ChatGPT vs. Cursor: The All-In-
• (00:21:15) - OpenAI's new AI Browser
• (00:25:49) - Ben Evans on OpenAI's New Browser
• (00:29:58) - ChatGPT: Adding a Layer of Protection
• (00:35:15) - Back to the Data
• (00:35:27) - Perplexity vs Reddit: Who's Right?
• (00:40:54) - How To Win at Indie Film
• (00:41:09) - Will AI Take Your Job?
• (00:46:54) - Interest Rates and Job Loss
• (00:53:17) - Too many people went into tech jobs
• (00:55:24) - Amino the AI Meme
• (00:57:22) - What Happened To My TechCrunch Event?
• (01:01:22) - Tim Ferriss to Perform in San Francisco

This episode hits Apple CEO rumors, OpenAI’s app marketplace, the rise of spec-driven development, deepfake ethics, and the grind behind creating viral content. Plus: Mark Cuban’s AI challenge, Sora’s cultural shockwave, and Gregory’s chaotic SF event planning.

️ Episode 018 – Highlights

Tim Apple and the End of an Era (0:00)

Gregory calls in from WeWork and dives into rumors that Tim Cook may step down. The hosts debate his legacy: operational genius or creative slowdown? Paul argues Apple’s never been “behind” on AI—just perfectly timed for mainstream waves.

OpenAI Dev Day and the App Store for AI (11:01)

OpenAI launches a full app marketplace with Figma, Expedia, Spotify, and Booking.com integrations. Paul loves the vision of chat as the new browser. Gregory calls it a “command-line nightmare” no normal user wants. Cue live demo of AI playlist-making chaos.

AI Playlist Fails and Command-Line UX (14:00)

Gregory tests ChatGPT + Spotify to build a Halloween playlist and album art. The results: vibes good, UX terrible. Paul argues voice input could save the experience; Gregory says Steve Jobs would hate this UI.

Spec-Driven Development (22:46)

Paul introduces “spec-driven development,” a shift away from code as truth toward AI-generated plans and human language specs. Gregory compares it to moving from assembly to modern languages—a new layer of abstraction for vibe coding at scale.

The YouTube Growth Curve (35:17)

Gregory shows The Gregory and Paul Show’s analytics jump—from three views to 3,400+ after daily shorts. Lesson: everything looks like a waste of time until it’s not. Volume + consistency = breakthrough.

Deepfakes and the Post-Truth Internet (39:45)

Mark Cuban dares fans to make deepfakes of him. Gregory recalls Sam Altman’s take: “we have to learn to live w...

This episode welcomes designer Stanley from Be Curious Studio to riff with Gregory and Paul on OpenAI’s Sora launch, the rise of AI “slop tools,” fraud fallout in startup land, Claude’s coding edge, Gemini 3.0, and why everyone is suddenly building “AI friends.” Plus: Reddit stock drama, Canva outages, and the meme of the week.

️ Episode 017 – Highlights

Gregory’s Empty House + Steve Jobs Vibes (0:07)
Gregory streams from an empty apartment, channeling the iconic “bed and lamp” Steve Jobs photo. The crew riffs on startup aesthetics and whether Mad Men or Silicon Valley culture won.

Guest Intro: Stanley, Creative Director (4:52)
Stanley shares his work blending brand, product, and sensory design—and why raw, unpolished conversations matter more than staged media.

OpenAI’s Sora: TikTok or Gimmick? (10:46)
Sora lets you generate deepfake-style videos of yourself in any scenario. Gregory finds it technically stunning but gimmicky, Paul sees massive remix potential, and Stanley warns it’ll be defined by creators—or flooded with garbage.

OpenAI’s $150B Valuation (27:13)
Now worth more than SpaceX, OpenAI’s valuation climb sparks debate. Jensen Huang even called it a “$10T company.” Employees mostly hold onto stock—betting on the upside.

⚖️ Fraud Watch: The Frank Scandal (28:26)
Founder Charlie Javice goes to prison for selling fake users to JPMorgan. Gregory highlights the engineer who refused to participate—avoiding jail by standing his ground. Lesson: saying no can save your career.

‍ Claude Sonnet 4.5 (33:00)
Anthropic doubles down on coding. Paul calls Claude the best developer model, Stanley compares prompt precision to communication mastery, and Gregory explains why he still defaults to ChatGPT.

Token Pricing = AOL Minutes? (39:00)
The team compares AI tokens to 1990s “internet minutes.” Painful now, but destined to disappear as costs fall.

Reddit Stock Dips 14% (47:45)
MAUs drop and reporters panic over ChatGPT citation data. Paul says it’s a healthy correction after a 113% run-up. Gregory bought the dip.

ChatGPT Checkout (49:42)
OpenAI experiments with shopping inside ChatGPT. Gregory sees it as proof of real monetization pathways—ads, shopping, fintech. Paul raises the Apple tax question.

AI Friends & Bully Bots (53:12)
AI companions flood the market. The “Friend” device flops in New York. Gregory imagines a bully AI that bosses you around. Stanley wants a tax AI. Paul just wants no extra friends.

Canva Goes Down Gracefully (59:37)
Canva’s outage status page earns praise for its clean UX—Gregory compares it to Twitter’s fail whale.

Meme of the Week (1:00:51)
E-commerce “ignore previous instructions” prompt injection memes, plus Gregory’s viral take on $30k baby naming consultants (“meet Taco Bell Gordas™”).

This episode covers the finalized TikTok divestiture to a U.S. consortium, OpenAI quietly building adtech infrastructure, Cloudflare’s birthday product blitz, Figma’s leap into vibe-coded design, Facebook’s awkward AI image generator, Amigo’s uncanny AI avatars, and the MIT/HBR report on “work slop.”

️ Episode 016 – Highlights

Fall Vibes & Tech Bro Podcasts (0:08)
Gregory and Paul catch up on weather in Toronto and Seattle, joke about turning the stream into a real podcast, and why Sunday gym pods just hit different.

TikTok Divested: MAGA Bros Buyout (2:05)
The U.S. consortium deal closes—Oracle, A16Z, and Silver Lake take control. Data moves to Oracle servers, and the U.S. gains leverage over the algorithm. Debate: at $14B, is TikTok massively undervalued compared to Reddit, X, and Snap?

OpenAI Builds Ad Infrastructure (9:00)
A job posting sparks rumors of an OpenAI ad network, but the hosts unpack what’s really happening: building in-house systems to buy ads and scale user acquisition. Gregory sees platform risk, Paul wonders if this means GPT adoption has plateaued.

Cloudflare’s Birthday Product Drop (16:00)
Cloudflare launches DIY vibe coding infrastructure—essentially “make your own Lovable.” Gregory compares it to Ning (build-your-own social networks circa 2008). The duo asks: are we in the “third wave” of the hype cycle?

Figma’s Vibe Design Tool (32:00)
Figma unveils AI-generated signup flows. Clean code, better than Lovable, but templatized. The hosts discuss the rebundling of product/design/dev roles and why generalists are winning—until specialization inevitably returns.

️ Facebook’s Awkward AI Slop (38:00)
Meta drops a cartoony AI image generator. Paul thinks it’s useless, Gregory argues Gen Z doesn’t care about polish—they just want to make stuff. Cue a nostalgia rabbit hole: what will people be nostalgic for in 20 years?

‍ Amigo AI: Real-Time Avatars (48:21)
An app that replaces your face and voice in live calls, indistinguishable from reality. The crew warns: deepfake-era misinformation is here. Blockchain or account provenance may be the only way to authenticate reality.

Work Slop & Enterprise AI Failures (55:00)
MIT + HBR report: 95% of enterprise AI pilots show no ROI. Gregory and Paul argue it’s not AI’s fault—it’s bureaucracy. Startups thrive because big orgs can’t escape compliance, approvals, and incentives that reward “garbage first drafts.”

This episode covers Larry Ellison’s TikTok takeover, why Salesforce and Microsoft are struggling with AI adoption, Google Cloud’s unexpected AI windfall, the ongoing “will Meta glasses ever matter?” debate, Reddit’s data deals with OpenAI and Google, and the wild ride of OpenDoor as the newest meme stock.

️ Episode 015 – Highlights

Sunny Days & Ice Cream Regrets (0:08)
Gregory and Paul kick off with sunny weather updates from Seattle and Toronto, debating whether daily ice cream is a vibe or a problem.

Larry Ellison Buys TikTok (3:00)
Oracle, A16Z, and Silver Lake scoop up TikTok’s U.S. entity. Data moves to Oracle servers. Gregory calls it the “most logical solution” to the CCP spying fears.

Big Tech vs. Startups in AI (11:00)
Salesforce Agentforce and Microsoft Copilot struggle with adoption, while AI startups like Cursor and Lovable scale revenue at record speed. The hosts argue: is this finally startups’ time to shine?

☁️ Google’s Cloud Cash Cow (23:00)
AI startups are burning so much compute that Google Cloud is booming, even as its consumer AI products lag.

️ Meta Glasses Flop Again (28:04)
A live demo crash makes Zuckerberg’s new smart glasses look weak. Gregory and Paul riff on why no one markets AR glasses for cycling, golf, or sports.

Reddit’s $200M AI Data Deals (43:30)
Halfway through major licensing with Google and OpenAI, Reddit leans into “Reddit Answers” while providing training data. Paul argues Reddit may be the last high-quality text dataset standing.

OpenDoor: Meme Stock 2.0 (49:04)
A Toronto analyst pumps OpenDoor from 50 cents to $10. Gregory calls it “GameStop for real estate.” Meme stocks as the new investor relations strategy?

Meme of the Week: Fed Rate Cut Day (59:57)
The Dumb Money guy celebrates Jerome Powell’s pivot. Meme stocks meet macro memes.

This episode covers Tucker Carlson’s tense interview with Sam Altman, Oracle’s $300B cloud deal with OpenAI, Apple’s thin new iPhone and AirPods with live translation, the largest npm hack in history, and why Perplexity is backing away from AI ads. The guys finish with a dive into Cluey’s viral marketing engine and an update on their upcoming TechCrunch Disrupt mixer.

️ Episode 014 – Highlights

Tucker vs. Sam Altman (0:07)
Tucker Carlson presses OpenAI’s CEO on tough topics, from employee scandals to AI risks. Gregory and Paul debate whether CEOs can survive this level of scrutiny in today’s media environment.

☁️ Oracle’s $300B AI Cloud Bet (9:41)
Oracle lands OpenAI as a customer. Larry Ellison re-enters the spotlight as Oracle’s stock spikes, showing why a “neutral cloud” alternative matters.

The Thinnest iPhone + AirPods Translate (15:24)
Apple drops a thinner iPhone 17 Pro in pumpkin spice orange—and AirPods that can live-translate languages. Cool or meh?

⚠️ npm’s Supply Chain Hack (20:47)
A phishing attack compromises millions of packages. Paul explains how one maintainer’s mistake created mayhem across the software world. Gregory wonders why attackers aren’t better at monetizing hacks.

Perplexity Pauses AI Ads (33:42)
Once seen as the future of search monetization, Perplexity walks away from LLM-based ads. Gregory argues AI ads are still “Google Adwords x10”—the only question is who will scale them.

Cluey as a Meme Stock for AI Tools (42:14)
The viral note-taking app has mediocre product reviews but world-class marketing. Paul breaks down their UGC machine. Gregory compares it to Tesla and luxury branding.

SF Founder + Investor Mixer at Disrupt (57:03)
Gregory’s October 28th mixer hits capacity, with investors, founders, and Stifel as marquee sponsor. Waitlist now open.

On this episode, Gregory and Paul dive into the return of the X algorithm, Apple’s surprising Gemini partnership, Google’s antitrust win, Atlassian’s $610M browser bet, Waymo expanding to Seattle, Stripe’s stablecoin rails, and the controversial new “AI Key.” They wrap with details on their founder + investor mixer at TechCrunch Disrupt SF.

️ Episode 013 – Highlights

The Algorithm Is Back (0:00)
X restores the engagement magic. Nikita’s “How to get rich on X” thread sparks debate. Gregory shares how a viral tweet brought him back from the brink of switching to Threads.

Apple + Google = Gemini Siri? (8:42)
Breaking news: Apple tests Gemini for Siri, leaving OpenAI out in the cold. The crew debates whether Siri can ever be rebooted—or if the brand is already dead.

Google’s Antitrust Win (13:54)
The DOJ lawsuit fizzles. No Chrome divestiture, no Android breakup. Google pays $425M instead of $31B—and adds $100B+ in market cap. Gregory rants on why the open web basically runs on Google.

Atlassian Buys a Browser (25:06)
Why did Atlassian drop $610M on Arc? Paul explains the dev cult around Arc’s side-tab UX. Gregory wonders if this is about Jira integration—or just investor exits.

Waymo Expands to Seattle (29:52)
Gregory recalls his mind-blowing first ride in San Francisco. Paul promises to film his first Waymo trip. They debate whether self-driving cars will ultimately eliminate driver’s licenses.

Stripe’s Stablecoin Rails (33:27)
Stablecoins might be the killer blockchain use case. Gregory lays out why Circle, Stripe, and private stablecoin issuers matter more than Fedcoin. Paul sees a fix for Canada’s broken payment rails.

The AI Key: Rootkit or Revolution? (41:44)
A USB-C dongle promises to turn your phone into a true AI assistant with system-level access. Gregory’s first thought: “Is this nation-state spyware?” Paul breaks down why Apple’s APIs force this hacky hardware approach.

SF Founder + Investor Mixer (51:42)
The October 28th TechCrunch Disrupt mixer hits 99/100 registrations. Fireside chats, networking, and maybe live demos. Drinks are on Paul.

Investment advisory services are offered through Twin Peaks Wealth Advisors, a registered investment advisor. The information presented in this article is for general informational and illustrative purposes only and does not constitute personalized investment advice. All opinions expressed are current as of the date of publication and are subject to change. Any references to market or economic conditions are based on information believed to be reliable but are not guaranteed to be accurate or complete. Past performance is not a guarantee of future results.

Additional Disclaimer for Small Exits & Angel Investing and Preparing for Acquisition:
Private placements are for eligible investors. Access to certain venture funds may be available at minimums as mentioned, but this is subject to manager terms. Such investments are illiquid, speculative, and may result in loss of principal.

On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week.

On this episode, Gregory and Paul welcome Tushar Kumar, private wealth advisor and co-founder of Twin Peaks Wealth Advisors. Tushar shares his founder journey, lessons from scaling to $500M AUM, and practical advice for tech professionals navigating equity compensation, IPOs, and acquisitions. The crew also dives (delves) into the hotly debated MIT report claiming 95% of enterprise AI pilots fail, and explores whether AI is creating efficiency—or killing jobs.

️ Episode 012 – Highlights

☕ Cold Brew & Espresso Kicks (0:00)
Gregory and Paul set the Friday vibe, catching up from Brooklyn and talking coffee rituals.

Guest Intro: Tushar Kumar (0:35)
Private wealth advisor and co-founder of Twin Peaks Wealth Advisors, helping tech founders and employees navigate equity, taxes, and wealth strategy.

From Cold Calls to $500M AUM (3:00)
Tushar recounts his entrepreneurial journey—launching during the 2009 financial crisis, cold-calling Cisco engineers, and the grind of building a wealth practice from scratch.

Founders & Concentrated Equity (9:00)
What to do when your net worth is tied up in your startup stock. Tushar breaks down strategies for every stage—from early exercising ISOs to navigating tender offers and IPOs.

Estate Planning & CPA Partnerships (11:30)
The underrated essentials: why every founder needs an estate plan and a sharp CPA long before an exit.

The Biggest Myth in Tech Wealth (14:30)
Tushar debunks the idea that you can “wait until after the exit” to plan. He explains why proactive planning saves millions in taxes and stress.

Quitting Big Tech to Launch a Startup (18:00)
Advice for employees at Google, Meta, or Microsoft who want to take the leap: building guardrails, saving runway, and investing for cash flow.

Small Exits & Angel Investing (22:30)
How to balance reinvesting in your next startup versus diversifying, and why angel bets should be capped at 1–2% of your liquid net worth.

Preparing for Acquisition (31:00)
Five steps every founder should take before selling: option exercise plans, defining “enough,” hiring CPAs, estate docs, and mapping post-exit wealth goals.

MIT Report: 95% of AI Pilots Fail (35:00)
The panel unpacks why AI pilots flop—unwillingness to adopt, fear of job loss, and lack of change management—and whether AI is really displacing jobs.

AI, Jobs & The Future of Work (39:00)
From robots in eldercare to vibe coding at hackathons, the crew debates whether AI is a job killer or the next great productivity unlock.

️ AI Agents & Security Patches (50:00)
Paul explains how parallel AI agents can orchestrate tasks like patching vulnerabilities—radically boosting efficiency in software development.

Meme of the Week (53:40)
“New Jobs...

On this episode, Gregory and Paul welcome Charlie “In the Arena” Freeman, AI systems architect and founder of Razroo and Makebind. The crew dives into AI-generated code for non-technical founders, what AI is actually good at (and what it isn’t), the rise of synthetic data, and a few very Black Mirror topics like AI Barbie and Meta’s push toward superintelligence.

️ Episode 011 – Highlights

☕ Coffee, Cold Brew & “Best Sister” Mugs (0:00)
The hosts kick things off with Friday vibes, coffee rituals, and a quick re-intro to the show.

Guest Intro: Charlie Freeman (2:10)
Charlie “In the Arena” Freeman joins the show. Founder of Razroo and Makebind, he builds AI systems that bridge non-technical founders to production-grade software.

️ Makebind & Razrew: Building Without Developers (5:00)
Charlie explains how Makebind turns natural language tickets into tested, production-ready code—giving startups a way to launch without paying $10–15k/month for devs.

Synthetic Data & Quality Assurance (17:45)
The group unpacks how synthetic data accelerates AI coding pipelines, ensures reliability, and explains why “100% quality” is the real differentiator for non-technical teams.

What AI Is Actually Good At (22:40)
Using a Stanford study as a jumping-off point, the crew debates AI’s strengths (image gen, x-rays, content) vs. its weaknesses (self-driving, customer support, therapy).

Self-Driving Cars & Human Tradeoffs (26:00)
From snowy Vermont roads to trolley-problem scenarios, the hosts question whether AI can ever make “right” tradeoffs—or if human oversight will always be required.

‍ AI Barbie: Creepy or Genius? (42:50)
Mattel launches an AI-powered Barbie with OpenAI integration. The panel debates whether conversational dolls are the future of toys—or a straight-up Black Mirror episode.

️ Meta, AGI & the Superintelligence Rift (48:45)
Meta hires Alexander Wang to lead its superintelligence group, clashing with Yann LeCun’s skepticism about AGI. The crew wonders if it’s real strategy—or just a talent block move.

Worldcoin, Iris Scans & The Social AI Race (58:00)
Could OpenAI’s rumored “social network” rival Facebook? The hosts look at Worldcoin’s iris-scan ID push and what it means for trust, privacy, and the future of social platforms.

On this episode, Gregory dials in from LA, Paul unpacks the rise of “vibe marketing,” and the duo debates Elon’s feud with Sam Altman, Perplexity’s Chrome bid, and whether AI CapEx spending is holding up the entire world economy.

️ Episode 010 – Highlights

Live from LA & Show Reintros (0:00)
Gregory checks in from his LA hotel and the hosts reintroduce themselves for new listeners. Gregory reflects on 20 years in Silicon Valley startups, while Paul shares his journey from software engineer to marketer.

⚡ Vibe Marketing & Automation (1:20)
The hosts define “vibe marketing” as more than automation—it’s how brand, message, and connection differentiate you in an AI-saturated world. They argue that how you do things now matters more than what you do.

The New Marketing Playbook (4:50)
With AI tools making execution easy, anyone can scrape leads and send 1,000 emails. The real moat? Your voice, your vibe, and your ability to stand out in the noise.

Elon vs. Sam Altman: App Store Beef (5:30)
Elon lashes out at Apple’s deal with OpenAI, accusing them of antitrust moves. Sam fires back with a “skill issue” tweet. The hosts debate who’s right, whether X is fair, and if Elon’s strategy shows he’s worried.

X, Android Dream Teams & Product Chaos (10:00)
Elon assembles an “Android dream team” despite years of bashing the platform. Gregory and Paul question X’s product strategy after rollbacks on X Chat and failing to launch breakthrough features.

Perplexity Wants to Buy Chrome?! (12:30)
Perplexity shocks the industry by publicly bidding for Chrome. The duo debate whether it’s genius marketing, an Amazon-backed play, or just PR theater.

️ AI Browsers vs. Agents (14:30)
Are AI-powered browsers a fad? Paul argues they’re transient—AI agents and MCP servers will replace them. Gregory pushes back, noting legacy web demand could keep browsers relevant longer.

️ MCP Servers: APIs on Steroids (28:00)
The hosts geek out on MCP servers, calling them “powerups” for AI. They explain how they differ from APIs, why they’ll reshape software, and how branded MCP experiences could become the next layer of trust.

AI CapEx Spending = The New Stimulus (32:00)
Balaji’s chart sparks a debate: AI infrastructure spending just surpassed consumer spending as a driver of GDP. Is this sustainable? The duo compare it to China’s infrastructure boom and America’s stimulus hangover.

Capitalism, Socialism & Regulation (40:00)
From FDA rules to federal AI policy, Gregory and Paul debate free markets vs. centralized planning. Are AI regulations premature—or a necessary national security move?

AI Psychosis & Model Restrictions (50:00)
The hosts discuss AI-induced “psychosis,” mental health risks, and whether restricting models like GPT-5 helps or hurts.

Tech Jobs, Salaries & The Next Wave (56:00)
Post-COVID salaries are crashing. Developers resist adjusting, but downturns often birth the next billion-dollar startups. Gregory and Paul predict a new wave of AI-native giants will emerge from this cycle.

Closing Take (59:30)
Recessions prune the ecosystem, but they also unlock the biggest opportunities. The duo argues this is the best time to start building.

Chapters

• (00:00:01) - Greg and Paul
• (00:00:41) - Vibe Marketing
• (00:05:22) - Elon Musk, His Beef With Sam Altman and More
• (00:06:10) - Apple vs Elon Musk: Who's Right?
• (00:09:19) - Elon Musk Is assembling the Android Dream Team
• (00:12:25) - Top Tech Comment: No AI Browser
• (00:14:53) - Pexile: Who Will Buy the Company?
• (00:19:34) - Web 2.8: The AI Agent
• (00:24:37) - Will MCP Servers Be Branded?
• (00:28:22) - MCP Servers: What Is An MCP Server?
• (00:32:23) - AI Capex Spending vs Consumer Spending
• (00:39:00) - Private vs Public Spending on Infrastructure
• (00:41:16) - What Is Socialism vs. Capitalism?
• (00:46:08) - Can We Regulate AI?
• (00:51:52) - WSJD Live: Do We Need More Tech Workers?
• (00:59:45) - Boskoe

On this episode, Gregory and Paul geek out live from the Coinbase Code NYC hackathon, diving deep into GPT-5's tool-calling revolution, the wild future of AI wearables and autonomous agents, and a conspiracy-fueled theory on why America's AI infrastructure buildout might be a secret weapon in the next autonomous war. Plus: Paul's vegan glow-up, the death of browser-based internet, and why nerds need better marketers for their dystopian demos.

️ Episode 009 – Highlights

Live from Coinbase Code NYC Hackathon (0:00)
Paul reports from the sold-out 200-person hackathon in Brooklyn, where he's judging apps for his customer Flora's MCP server marketplace. Highlights include a crypto-incentivized tutoring app for kids and a creative vs. viable category showdown.

GPT-5: Tool-Calling Takes Over (5:45)
The duo dissects GPT-5's shift toward engineering and tool integration, competing with MCP servers, and why it's moving beyond raw intelligence to autonomous capabilities. Gregory praises its coding superpowers for vibe coders like him.

Backwards Compatibility Blues (15:20)
Gregory and Paul unpack the backlash over lost GPT conversations, personality changes, and why OpenAI might be prioritizing AGI vision over user experience—despite the hype not living up to expectations.

The End of Browsers and Rise of Agents (25:30)
From HTTP alternatives to autonomous agents replacing web interactions, they explore how AI could make computers obsolete. Paul floats the idea of a local, vault-like personal AI on your phone for privacy and power.

AI Wearables: Creepy or Convenient? (35:10)
Amazon's acquisition of "B" wearable sparks talk on always-on AI companions. They critique corny demos (Black Mirror vibes), debate form factors (glasses, watches, robot dogs), and why the phone might still reign supreme.

️ Conspiracy Corner: AI for Autonomous Wars (45:55)
Paul spins a wild theory that America's massive AI infrastructure spend (2% of GDP) is secretly prepping for drone-dominated conflicts against China—because computational power and energy could decide who wins the next war.

Paul's Vegan Era (55:40)
Amid food truck announcements, Paul shares his return to veganism for health reasons (high cholesterol) and why he's now the most annoying bike-riding, plant-based evangelist at the hackathon.

Upcoming Events

Stay tuned for more hackathon winners and Paul's social media updates from the event.

Chapters

• (00:00:01) - Paul Talking To Greg
• (00:00:06) - Coinbase Code NYC
• (00:03:19) - Incentives for Students to Go to School
• (00:05:19) - Back to Work: Tech Hackathon
• (00:08:25) - GPT 5 vs. MCP: Should They Compete?
• (00:13:42) - Don't Need a Computer Science Degree to Get a Job
• (00:20:01) - Talking to an AI With 5 GPT
• (00:25:14) - People Try Vegan Food For A Week
• (00:26:50) - How GPT5 Will Affect the Internet
• (00:32:53) - AI glasses: corny
• (00:36:59) - Personal Agents for Apple's Future
• (00:40:06) - GPT5: The Marketing
• (00:42:58) - Trump on AI Infrastructure
• (00:48:10) - Why Is the US Building a Massive AI Infrastructure?
• (00:53:42) - Happy Holidays!

On this episode, Gregory wraps his Seattle SaaS takeover, Paul dreams of deepfake-proof memes, and the duo digs into the ripple effects of GPT-5, the Figma IPO boom, and the fate of AI tools pivoting to services. Plus: sovereign AI, voice cloning V3s, and Zuckerberg’s AI moonshot memo.

️ Episode 008 – Highlights

️ Seattle, AI House, and Event Takeovers (0:00)
Gregory recaps his solo talk at Seattle Tech Week’s AI House with 550 RSVPs, standing-room only. The waterfront venue, backed by Paul Allen’s foundation, wowed attendees and even convinced him to move his co-working space there.

Toronto & SF: New Tour Stops (4:40)
Next up: Toronto on Oct 6 (Elevate pre-event) and a founders + VC mixer at TechCrunch Disrupt in San Francisco. Gregory teases speakers from Bain and Strata Capital and says the SF event is already stacked.

GPT-5 Rumors Are Real (9:07)
GPT-5 is officially on the way this August. Sam Altman confirmed it, but no date yet. The hosts debate whether it’ll upgrade AI products—or kill them. Paul predicts wrappers vanish, and Gregory sees a future of model specialization, not a “one LLM to rule them all.”

Claude vs. GPT vs. Cursor (12:55)
Cursor teases a move to GPT-5. With a 1M token context window, entire codebases can now fit in one prompt, making memory workarounds obsolete. Foundational model wars heat up.

Sovereign AI & Global Language Wars (17:00)
The rise of nation-backed models sparks a debate: Will English dominate AI training, or will Chinese and dense-language models gain an edge?

Figma IPO Goes Parabolic (19:17)
Figma IPOs at $33, peaks at $200, and closes at $115—hitting a $60B valuation. Gregory explains why this unlocks fresh LP cash for startups. Also, Figma CEO Dylan Field is a Thiel Fellow dropout. Vindication?

Teal Fellowship & The College Bubble (24:43)
The hosts dive into the post-secondary education crash and how Teal’s anti-college bet is aging well. Paul argues that overpriced degrees should be illegal. Gregory compares degrees to ads with no ROI.

️ Eleven Labs V3 Alpha: Voice Gets Weird (30:20)
The latest text-to-speech model mimics laughter, hiccups, and multilingual tone. Paul calls it the most human-like AI voice yet. The Netherlands passes a law making your voice and likeness legally protected IP.

From SaaS to Service: Icon's Pivot (33:40)
Icon.com raised money to build an AI ad generator. Now they’re pivoting to a creative agency. Paul says it’s proof that most AI tools just don’t work well unless you already know what you’re doing.

Launch Videos Are the New PR (36:00)
Forget TechCrunch. The new norm? Founder-made launch videos on X. Paul praises CaseFlood’s clean demo and the fall of Cluey-style ragebait.

Zuckerberg’s AI Memo: A Pattern Emerges (38:00)
Ow Malik compares Zuck’s latest AI memo to past turning points—mobile, VR, and now personal intelligence. Paul calls it classic Zuckerberg: a long-term bet others won't make.

Apple, Meta & the Race to AI Hardware (43:10)
Gregory thinks Meta's problem is hardware delivery. Paul says Apple is playing smart—waiting and learning. OpenAI x Jony Ive's AI wearable might finally get it right, succeeding where Humane and Rabbit failed.

The iPhone Disruptor? (50:30)
Can a new AI device go mainstream? The hosts think it must complement phones before it replaces them. Subsidized distribution via carriers could be key, just like early iPhones.

Passive AI Agents: The Real Dream (56:30)
Gregory wants an agent who books his flights without being told. The future? AI that listens, learns, and acts quietly in the background—like a personal OS.

Meme of the Week: Sydney Sweeney Breaks SaaS Twitter (58:00)
Sydney...

Chapters

• (00:00:02) - Gregory and Paul: Time to Talk Podcasts
• (00:02:12) - Seattle Tech Week: The AI House talk
• (00:05:48) - Tim Ferriss to Attend TechCrunch Disrupt Toronto
• (00:09:03) - OpenAI GPT5 Launch in August
• (00:16:05) - Will English be the dominant language in AI?
• (00:19:20) - IPOs are back in Silicon Valley
• (00:23:31) - Peter Thiel's Thiel Fellowship
• (00:29:57) - The Old Fellows Program
• (00:30:14) - AI at CES 2017: Speech to Speech
• (00:32:51) - AI Ad Maker: Should You Fire Your Creative Team?
• (00:35:51) - Caseflood's Fun Launch Video
• (00:37:06) - Giga Ohm on Facebook's New AI Memo
• (00:41:40) - Zuckerberg on His New 2025 Plan
• (00:43:34) - How Facebook Can Dominate the Metaverse
• (00:48:02) - Will the AI-enabled Headset Replace the Smartphone?
• (00:50:44) - OpenAI: Will It Disrupt the Phone Market?
• (00:56:05) - AI Agents for the Passive User
• (00:58:19) - The New Nike Ad

On this episode, Gregory and Paul ride a wave of summer vibes and dive headfirst into the return of tech events, the sneaky debut of GPT-5, the unraveling of Twitter (X), and the rise of AI wearables. Plus: a genetic engineering breakthrough, Elon’s AI Vine mystery, and the meme queen of SaaS—Sydney Sweeney.

️ Episode 007 – Highlights

Summer Break & Portland Hipsters (0:00)
Paul returns from a nostalgic trip to Portland, where the 90s never died—and neither did VHS. Gregory reminisces about hipster culture and overpriced cassette tapes.

Events Are Back, Baby (2:41)
From Toronto Tech Week to Climate Week Seattle, in-person is booming again. Gregory previews his sold-out Seattle Tech Week talk (+240-person waitlist) and announces a Toronto stop at Elevate in October.

Mixing with VCs at Disrupt (6:50)
An exclusive founder–VC mixer is planned for TechCrunch Disrupt. Gorgian teases a TBA headline speaker and invites early-stage startups to DM for access.

GPT-5 Leaks Through Microsoft (9:23)
The next-generation model quietly drops into Microsoft Copilot before a public release. Paul speculates OpenAI’s rollout is hampered by ironclad Microsoft contracts and mounting pressure to monetize via travel and commerce.

✍️ ChatGPT's Writing Problem (12:28)
Gregory and Paul rant about the declining quality of GPT’s writing output and how OpenAI seems to be chasing Google Search dominance over useful tooling.

Platform Fatigue: X Edition (25:00)
Gregory admits he’s finally done with X (Twitter), as engagement plummets and content tilts toward TikTok-style slop. He’s officially pivoting to LinkedIn.

Where the Internet’s Headed (33:06)
The hosts explore alt-platforms like Threads, Farcaster, and Reddit, and why none have nailed it yet. Gregory experiments with Reddit as a personal publishing platform.

AI-Powered Wearables: Amazon Buys B (44:40)
Amazon’s acquisition of voice-first wearable “B” hints at Alexa’s next evolution: an always-on mood-detecting AI. Creepy? Maybe. Useful? Definitely.

️ Smart Glasses That Don't Suck (54:19)
Meta's Ray-Bans and other AR glasses are inching toward mainstream viability, especially for business use cases like translation and trade shows. Gorgian floats the idea of an anti-wearable device blocker.

Genetic Engineering Kills Malaria (20:08)
A bioengineered mosquito breakthrough could save 1% of Africa’s GDP by wiping out malaria. Paul embraces the pro-genetic future.

Vine Returns? (23:18)
Elon Musk hints at resurrecting Vine with AI. But what does that actually mean? Avatars? Grog content? Nobody knows.

Meme of the Week: Sydney Sweeney SaaS Edition (58:00)
Sydney Sweeney breaks SaaS Twitter with a wave of fake job memes—from working at Intel to founding a unicorn. Best one? Intel’s new CPO.

RIP Reality Icons (59:05)
Tributes to reality TV pioneer Ozzy Osbourne and tech-infamous wrestler Hulk Hogan, who played a key role in the downfall of Gawker.

Upcoming Events

Jul 28 – Seattle Tech Week: How to Market Your AI or SaaS Startup
https://lu.ma/uzp1qlf4

Oct 6 – Toronto (Elevate Pre-Event): From 0 to $1M in ARR
https://lu.ma/toronto-zero-to-one

Chapters

• (00:00:01) - The Guardian Paul Show
• (00:01:17) - Portland Is As Weird As You Think
• (00:02:43) - AI Marketing: Events are Back
• (00:04:49) - One More Event For TechCrunch Disrupt
• (00:07:59) - In the Elevator With San Francisco
• (00:09:22) - OpenAI's GPT5 Leaked,
• (00:16:27) - Chat GP: Can They Win at Search?
• (00:20:01) - Genetic Engineering to Reduce Malaria
• (00:23:15) - Elon Says He'll Bring Back Vine
• (00:26:09) - X.com vs. LinkedIn: The Future of Social Media
• (00:31:50) - X. Chat: The ghost of Blue Sky
• (00:35:10) - On The X and Discord
• (00:38:06) - Ideas for the Week: Do More on Reddit
• (00:39:23) - How To Escape Reddit Noob Jail
• (00:44:40) - B1, the Company That Was Acquired by Amazon
• (00:50:30) - Adam Levine: I Think AI Is Entirely Pre-Dest
• (00:54:04) - Wearable Goods
• (00:58:23) - The Future of Love Is On Camera
• (00:58:47) - Ozzy Os
• (01:00:21) - Hulk Hogan Dead

On this episode, we welcome AI-savvy marketer Nathan Binford straight from the jungles of Mexico. The crew dives into the dark arts of digital marketing, the real cost of Google ads, and why most marketers are platform experts but strategy novices. Plus: the rise of backdoor AI acquisitions, ChatGPT’s agent wars, and the Jumbotron affair that broke the internet.

️ Episode 006 – Highlights

Jungle Livestream (0:00)
Paul and Gregory welcome guest Nathan Benford, an AI marketer beaming in via Starlink from south of Cancún.

Platform Purgatory (2:34)
Nathan breaks down why marketers who over-optimise for platforms like Google and Meta are missing bigger opportunities—and how algorithm shifts can wreck strategy overnight.

Message vs. Channel (4:26)
Gregory gets nostalgic for Ogilvy-style messaging. Have we lost the plot by obsessing over pipes and forgetting what we’re piping?

Rising Ad Costs (6:01)
Clicks are more expensive, targeting is vaguer, and Google’s metrics are... deceptive? It’s a marketer’s minefield out there.

Scrappy Marketers Win (13:09)
In a world of rising costs and tightening margins, being clever matters more than budget. Nathan makes the case for pirate marketing.

️ Cold Outreach & Reddit Hacks (21:16)
Nathan shares fresh tactics—from reviving dormant email lists to warm-channel retargeting and why Reddit might be the new frontier for growth.

Bring Your Own Data (22:45)
How to use zero and first-party data to cut platform costs by 90%. Bonus: a clever hack using old domains + Seamless.AI + Bullseye for full-funnel targeting.

Backdoor AI Acquisitions (30:46)
Gregory and Paul unpack the “acqui-hire + license” trend taking over the AI space—from Inflection to Adept to Windsurf—and what it says about deal speed, antitrust, and market heat.

️ B2B vs. B2C: The Great Debate (47:54)
Why consumer startups are almost impossible without a celebrity, millions in funding, or both. Plus: the underappreciated goldmine of B2B.

GPT Agents vs. MCP (54:12)
ChatGPT rolls out agent infrastructure—without adopting the MCP protocol. Paul predicts the rise of platform-specific agent ecosystems. Claude goes open, OpenAI doubles down on proprietary.

Meme of the Week (56:51)
The viral “Jumbotron Affair” leaves no one unscathed. A friend knew. Twitter knew. Even the intern knew. Link: https://x.com/anuibi/status/1945785577158164954

IRL Is Back (1:00:03)
Workshops, tech talks, and events are in full swing. Gregory plugs a sold-out Seattle Tech Week talk and a fresh Toronto date with Paul during Elevate.

Jul 19, Bellevue – Every Marketing Channel Sucks
https://www.venturemechanics.com/events

Jul 28, Seattle – How to Market Your AI or SaaS Startup (Seattle Tech Week)
https://lu.ma/uzp1qlf4

Oct 6, Toronto – From 0 to $1M in ARR (Elevate Pre-Event)
https://lu.ma/toronto-zero-to-one

Chapters

• (00:00:01) - Hello, How Do We Know You?
• (00:01:23) - Alexa enthusiast Nathan Binford on The Gregory Paul Show
• (00:01:59) - Most Marketing Experts Are Platform Experts
• (00:09:44) - Living in the Wild West
• (00:13:14) - Cost going up in the marketing industry
• (00:15:11) - Marketing Costs Will Go Up
• (00:21:35) - Beyond Facebook: Medium, LinkedIn, and More
• (00:27:34) - How to Use LinkedIn as a Branding Tool
• (00:30:11) - Backdoor Acquisitions in the AI Space
• (00:35:09) - The Hype Cycle of AI
• (00:38:14) - Anticipation of a Bigger Google
• (00:44:23) - How Marketing Became More commoditized
• (00:44:35) - Reddit: Do Startups Need Marketing Support?
• (00:47:53) - Mixed Views on B2B vs. Consumer
• (00:54:05) - ChatGPT: OpenAI's AI Agent
• (00:56:47) - Cringe Meme of the Week
• (00:59:46) - Oh My God
• (00:59:58) - How to Market Your Events
• (01:00:42) - A Taste of Elevate Toronto

On this episode, Paul beams in from a sunny Ontario patio to debate whether NVIDIA’s $4 T valuation signals peak-AI, dissect Apple’s stealth diffusion-model leak and its on-device future, unpack the wild story of an engineer juggling 30 YC jobs, and mine growth lessons from a Redditor who launched 39 startups before striking gold. Plus Google’s new “Forums” search tab, a flurry of IRL tech events, and the Sam-Altman-in-sunglasses meme of the week.

️Episode 005 – Highlights

Backyard Broadcast (0:00)
Paul kicks things off from his parents’ sun-soaked patio in Dunnville, Ontario—new set, same Friday-noon livestream energy.

️ Peak-AI Bubble Debate (4:38)
NVIDIA soars to $4T and Meta waves $200M pay packages at devs like NBA superstars. The crew spar over “shovel sellers” vs. “new electricity” and what a real bubble looks like.

Sohom “Over-Employed” Saga (12:54)
YC founders reveal an engineer juggling ~30 full-time gigs. Proof that hustle culture meets due diligence gaps. Reference checks, folks! link: https://techcrunch.com/2025/07/03/who-is-soham-parekh-the-serial-moonlighter-silicon-valley-startups-cant-stop-hiring

Apple’s Diffusion LLM Leak (19:17)
Cupertino quietly converts Qwen into an on-device diffusion model, hinting at privacy-first photo & AR wizardry, and a fresh AI strategy. Link: https://9to5mac.com/2025/07/04/apple-just-released-a-weirdly-interesting-coding-language-model/

39 Startups → 1 Win (29:14)
A Reddit indie-hacker shows charging before building beats freemium; “Minimum Sellable Product” becomes the new MVP. Link: https://www.reddit.com/r/indiehackers/comments/1lsidt7/i_launched_39_startups_until_one_made_me_millions/

Google’s AI Search Shake-Up (43:17)
AI answers reuse 10% of links, and a new “Forums” tab (Reddit, Quora, etc.) pushes community posts over corporate blogs, SEO playbook rewritten. Link: https://www.reddit.com/r/digital_marketing/comments/1ltspco/we_cracked_ai_mode_what_seos_need_to_know_to_stay/

Meme of the Week (54:17)
Sam Altman’s ultra-reflective shades inspire “Johnny-Ive eyewear” memes—perfect comic relief. Link: https://x.com/I_Am_GKennedy/status/1943102186499748141

IRL Events Are Back (55:42)
Seattle climate-tech night, Bellevue marketing talk, sold-out Seattle Tech Week, and an invite-only SaaS/AI mixer at TC Disrupt prove offline touchpoints still convert.

Vibe Your SaaS West Coast Tour:
Jul 16, Seattle - How to Monetize Your Climate Startup (Climate Week)
https://lu.ma/s01u1s6g

Jul 19, Bellevue - Every Marketing Channel Sucks
https://www.venturemechanics.com/events/venture-saturday-7192025

Jul 28, Seattle - How to Market Your AI or SaaS Startup (Seattle Tech Week)
https://lu.ma/uzp1qlf4

Oct 28, San Francisco - Vibe Your SaaS VC/Founder Mixer (TC Disrupt)
https://lu.ma/cs8tebvz?utm_source=vibeyoursaas.beehiiv.com&utm_medium=referral&utm_campaign=unlocking-reddit-marketing-secrets

Chapters

• (00:00:01) - Back outside with the dogs
• (00:00:12) - The New In Startup, AI SaaS, and More
• (00:01:35) - Apple News, AI Search, and More
• (00:02:30) - Canada Fourth of July Fireworks
• (00:04:36) - Is this the Peak of the AI Boom?
• (00:09:36) - Zuckerberg: AI Is In a Bubble
• (00:12:43) - A startup founder calls out a worker who works at 3 to 4
• (00:17:53) - Y Combinator's Gary Tan on The Hacking
• (00:19:17) - Apple Leaks a Local Learning Model
• (00:26:20) - Augmented-Reality Glasses: Future of AI
• (00:29:08) - Ideas for Starting a Startup With a Free Trial
• (00:33:16) - MVP: The MSP Minimum Sellable Product
• (00:39:56) - How to say no to a customer
• (00:43:15) - AI Marketing Hacking: The Future of Community Search
• (00:51:44) - How to Survive the AI Search Challenge
• (00:54:17) - Meme of the Week: Johnny Ives's Glasses
• (00:55:37) - Speech plugs: How to monetize your SaaS startup
• (00:57:04) - Interested in attending TechCrunch Disrupt 2018? Here!

On this episode, we chat with Chetan Nandakumar, a UC Berkeley–trained technologist and entrepreneur specializing in AI and decentralized systems, with a background in computer vision research and leadership roles at Modista, Gensyn, and now is the CEO and founder of Fluora, a monetized MCP marketplace.

️ Episode 004 – Highlights

0:00 — WTF is an MCP Server?
We kick things off with Chetan Nandakumar, who breaks down why MCP servers are becoming the HTTP of AI—and how they let agents plug into your data, tools, and workflows. More: https://www.monetizedmcp.org/

2:45 — Monetizing the Agentic Internet
Chetan explains how Flora’s MonetizeMCP enables AI servers to charge for services, much like Stripe does for agents. Smart contracts meet server-to-server commerce. More: https://www.fluora.ai/

7:00 — Every Business Needs an MCP Server Now
Just like websites were mandatory in the ‘90s, businesses in 2025 will need MCP endpoints to serve AI agents. Welcome to the B2A (Business-to-Agent) era.

14:00 — Agents That Hire Agents
We imagine a world where your AI agent doesn’t just book travel—it hires other agents to launch your startup or run experiments for your business goals.

19:00 — Identity, Payments & Trust Layers
From zero-knowledge proofs to creepy iris scans, we explore how humans, bots, and businesses will authenticate and transact in an agent-dominated web.

25:00 — B2B vs B2C Use Cases
SQL is dead? Not quite. Chetan shares how agents change both internal ops and customer-facing tools—if you stop giving them tasks and start giving them goals.

35:00 — How Agents Will Change Marketing Forever
No more selling with billboards and influencers. Agents don’t care. They just want the best product. The new game is product quality + clean APIs.

42:00 — The AI Film Revolution
We nerd out on tools like Higgsfield and Runway, and what’s holding back full-length AI movies (spoiler: character consistency still sucks).

48:00 — Meme of the Week: Peter Thiel Deepfake
Greg shows off his terrifyingly good Peter Thiel AI deepfake and what it took to get the voice, pauses, and tone just right. Link: https://x.com/I_Am_GKennedy/status/19...

56:00 — Final Take: The Internet Is Changing Fast
MCP servers, monetization layers, digital ID—this episode lays out how AI agents will transform not just apps, but the internet itself.

Chapters

• (00:00:00) - The Gregory and Paul Show
• (00:00:51) - Guest: Chayton Nanda Kumar
• (00:01:30) - How To Build a Decentralized Machine Learning Network
• (00:02:24) - What MCP Servers Are
• (00:04:16) - MCP: The Default Way for Agents to Interact with their
• (00:07:46) - Monetize MCP: What's It All About?
• (00:12:41) - The Future of Agents Is Connecting With Businesses
• (00:17:35) - Will MCP Eliminate the Need for SQL?
• (00:19:52) - AI Agents: The Marketing Future
• (00:22:20) - AI and Marketing: The Future of Money
• (00:27:15) - Facebook's 'Multi-Person' Chat
• (00:29:40) - Reddit to Use World ID to Verify Users
• (00:36:28) - Do we Need Domain Names?
• (00:37:54) - Google X Allegedly Stole Apple's Smart Earbuds
• (00:42:01) - 9 Brutal Truths About Starting a Business
• (00:44:32) - Pushing the Right Narrative
• (00:48:28) - AI Marketing first stuff
• (00:48:45) - AI First Marketing: The Intellectual Challenge
• (00:51:36) - AI Genetically Made Videos
• (00:56:07) - How AI Filmmaking Is Developing
• (00:57:23) - Meme of the Week

We stream live on X and LinkedIn at Noon Pacific every Friday, then straight on to YouTube.

About Our Guest Imran Patel

Imran Patel is the founder of Syft Data, a Los Angeles startup that takes the guesswork out of B2B marketing by enabling teams with people-level intent signals from website traffic. Prior to Syft, he spent eight years at Snap Inc., rising to Head of Engineering — Growth, where he led engagement, retention, and analytics platform teams. Earlier, Imran 6 years at AWS in the Bellevue, WA, and Seattle, supporting services such as CloudFront and Route 53 at Amazon. He holds a Ph.D. in Computer Science from UC Santa Barbara and is an inventor on multiple CDN-routing patents.

️ Episode 003 – Highlights

2:30 AI-First Marketing with Imran – Imran Patel explains how low-code, “vibe-coded” tools are revolutionizing the way marketers approach lead magnets. We also unpack tactics for catching high-intent ChatGPT traffic. Check out SyftData: http://syftdata.com/

20:15 Future of Work Debate – A Stanford survey says workers only want the boring stuff automated; VCs disagree. Sparks fly as we predict which roles actually disappear. See the report: https://x.com/RubenHssd/status/1934968317627998534

✂️
35:10 Big-Tech Reality Check – Amazon’s Andy Jassy claims AI will trim payrolls, but who really feels the squeeze? We track the ripple effects across global talent pools. Link to news: https://www.news.com.au/finance/work/leaders/amazon-staff-fire-up-after-ceo-andy-jassy-drops-artificial-intelligence-bombshell/news-story/9ed3e6a0098e2bcaea12f4b8c9569e68

50:45 Build-in-Public Backlash – Revenue transparency builds hype until copycats strike. We draw the line between smart sharing and oversharing. Here is the Reddit thread: https://www.reddit.com/r/SaaS/comments/1levhf2/building_in_public_isnt_a_good_idea_heres_my/

1:00:30 Meme & Reddit Corner – Stable-coin Baywatch pics and pre-revolution Tehran beach memes cap the show. Come doom-scroll with us. Memes upon memes: https://x.com/I_Am_GKennedy/status/1935162728576074111

Chapters

• (00:00:01) - The Haunted Mansion
• (00:00:07) - Fooled by Tech: Greg and Paul
• (00:00:36) - Interviewing Sift Data's Imran Patel
• (00:02:28) - AI and Marketing: The Future of Lead Generation
• (00:08:08) - Lead Magnet: White Coded Software
• (00:11:16) - SaaS Lead Generation: Where to Start?
• (00:17:13) - Are You Ready for AI Agents on Slack?
• (00:19:37) - "The Future of Work With AI?"
• (00:26:41) - How Stupid Is Silicon Valley's Investment
• (00:33:49) - Alex Jassy: AI Will Shrink Amazon's Workforce
• (00:40:46) - Will the Outsourcing of Software Hurt Emerging Economies?
• (00:46:18) - Will AI Replace the Translation Jobs?
• (00:50:10) - Podent Podcast
• (00:50:34) - Building In Public Isn't A Good Idea
• (00:53:24) - Peter Thiel on Building Public:
• (00:59:55) - New Money: 'It Just Seems Very New'
• (01:00:35) - Meme of the Week

We stream live on X and LinkedIn at Noon Pacific every Friday, then straight on to YouTube.

About Our Guest Arjun Dev Arora

Arjun Dev Arora is an early-stage tech investor and managing partner at Format One in San Francisco. He built and sold ad-tech pioneer ReTargeter, served as a Partner at 500 Startups, and was Entrepreneur-in-Residence at Expa. Arjun’s early checks have gone into Flexport, Notion, Virta Health, Branch, Firefly Aerospace, Calm, Tonal, Pipe, Grove Collaborative—plus exits like Teachable, Truebill, and Starship. He also backs next-gen funds—Streamlined Ventures, The House Fund, Susa Ventures, Caffeinated Capital, Rocketship VC, and more. Beyond venture, he chaired a $100 million healthcare foundation, now sits on the SFJAZZ board, and has been honored by the White House and the UN for values-driven leadership.

️ Episode 002 – Highlights

Apple’s “Illusion of Thinking” Paper
The trio debates Apple’s claim that LLMs “quit” on complex tasks—are they spotlighting a real weakness or just masking Siri FOMO? Consciousness ≠ computation is the consensus.

Meta × Scale AI Megadeal
A 49% buy-in nets Zuck elite talent and a priceless data moat. Panel verdict: bold talent grab and Wall-Street flex to stay in the foundation-model race.

️ YC’s Summer 2025 AI Wish-List
14 RFS prompts, 13 of them “AI-for-X.” Favorites: voice inbox, healthcare ops, residential security. Proof we’ve entered the AI Everything era.

️ WWDC25 & the Glass UI
Shiny translucent widgets wow designers, but Gregory argues Apple feels more corporate cosplay than cutting-edge. His one-slide fix: stop looking extractive, start looking innovative.

️ From Zero to One Screenshot
Reddit indie dev lands first premium signup for a screenshot-organizer SaaS—reminder that success is persistence over a perfect launch.

✉️ 15 Cold Emails a Day
A controversial Reddit post sparks a masterclass on outreach: hyper-personalize, get warm intros, and ignore the haters.

DM Deal-Flow
Paul closes a paying customer entirely via X DMs; Arjun explains why most pitches die in his inbox.

Meme of the Week
AI-generated spoof swaps Jony Ive & Sam Altman for Zuck and Alexandr Wang—complete with broccoli-cut hair and pearl earrings. Perfect send-off.

Chapters

• (00:00:00) - Facebook Live Chat
• (00:08:08) - Live Stream: Talking To Arjun
• (00:10:16) - The Zoom Experience
• (00:10:43) - Shedding Unread Books On Twitter
• (00:14:30) - Sahil's book is good,
• (00:17:16) - Toronto and Marin County, California
• (00:19:37) - A Week in the Life
• (00:20:29) - The New In Startup, SaaS, and More
• (00:21:04) - Interviewing Arjun Dev Arora
• (00:22:59) - Apple's 'The Illusion of Thinking' Paper
• (00:30:22) - Apple's Report on AI and Consciousness
• (00:32:28) - Apple Take on Meta's AI Merger
• (00:35:40) - Meta's Search for Scale
• (00:39:25) - Zuckerberg: Bringing AI Best Friends to Everyone
• (00:43:37) - Beyond YC's Summer 2025
• (00:47:41) - In the Elevator With AI
• (00:49:34) - AI Agents: The Future of Collaboration
• (00:52:05) - Personal Finance, Residential Security
• (00:55:09) - Apple's 'Over Polished' Marketing
• (01:00:06) - Apple's 'classic' brands
• (01:03:39) - Apple's '101 Slide'
• (01:04:08) - How to market your SaaS on Reddit
• (01:08:05) - Google Photos: A Living History of Your Computer
• (01:08:55) - The Secret to Success Is Simple Daily HABITS
• (01:11:43) - How to Cold DM
• (01:16:18) - Are Reddit DMS Full of Junk?
• (01:17:53) - Me of the Week: This One

Broadcasting every Friday at Noon, Gregory and Paul break down the latest in startups, SaaS, AI, and whatever the internet is arguing about that week. Expect smart takes, dumb takes, a few hot ones, and more than a few memes. The show streams live on X and LinkedIn.

️ Episode 001 – Highlights

Messaging Mayhem
The episode opens with a rant about the newly launched X Chat and its unusable desktop experience. Gregory and Paul share frustrations over managing conversations across Slack, Discord, and other tools.

‍ Slack Overload & Co-Working Culture
Gregory reflects on being part of 35 different Slack workspaces, while also reporting from a climate-focused co-working space in Seattle. The discussion compares startup incubators, bohemian founder vibes, and polished VC hangouts.

AI Is the New Code
They explore AI development tools like Cursor and Claude, and the shift toward prompt engineering as the new layer of abstraction in software development.

MVPs Are Out, MSPs Are In
Challenging startup orthodoxy, the duo argues that MVPs are outdated. Instead, they propose building only after someone commits to buy, coining the term MSP (Most Sellable Product).

SaaS GTM Tactics
A Reddit thread sparks discussion on improving SaaS revenue through better sales tactics: listening before demoing, pricing flexibility, onboarding support, and the dangers of free-tier users.

Marketing Rules Everything
Looking at companies like Asana and Salesforce spending up to 78% of revenue on marketing, Gregory and Paul emphasize that even the best products need full-on media strategies to win attention.

♟️ Meme of the Week
A viral Magnus Carlsen clip leads to a humorous reflection on startup math: “50% of $10M beats 1% of $250M.” The episode wraps with laughs, and plans to bring guests onto future shows.

Chapters

• (00:00:01) - "This Is Fun!"
• (00:00:14) - Slack vs. XChat: The New Chat is Stupid
• (00:04:29) - What is a Co-Working Space in Seattle?
• (00:07:46) - Neurodyne News of the Week: Cloudflare's
• (00:13:54) - Cursor 1.0
• (00:18:17) - Six Areas Where Live Coding Is Impacting the Business
• (00:26:04) - In the Elevator With Freebies
• (00:28:53) - Anthropic vs. Google AI: The Fight for the Future
• (00:36:05) - Will Content Companies Pay for Access?
• (00:39:24) - Revenue. On Reddit,
• (00:40:10) - Crazy Marketing Spending by Companies
• (00:42:58) - There's No Free Channel
• (00:46:13) - How We Helped This SaaS Company Go From 80,
• (00:49:25) - Onboarding from a SaaS to a Website
• (00:53:04) - AI First Marketing Idea
• (00:54:27) - Vibe Tech Trend Graph
• (00:54:54) - meme of the week: Magnus the Chess Master Sashes the Table
• (00:57:34) - OING Live Stream
• (00:58:17) - Hello, how are you?