Matthew Parker

Stretch Four Podcast

Business EN ↓ 56 episodes

The Stretch Four Podcast is hosted by Matthew Parker and covers topics across his world of venture-backed startup building, performance and health, family life, and living in San Francisco. He is joined by occasional guests and high performers who share their knowledge on company building their lifestyle hacks. New episodes released every Monday at 8 AM PST. stretchfour.substack.com

Author

Matthew Parker

Category

Business

Podcast website

stretchfour.substack.com

Latest episode

Mar 10, 2026

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Episodes

Anthropic Is Suing the Pentagon. OpenAI and Google Are Backing Them. 10.03.2026

Happy Tuesday. Little bit of a hiatus — a lot happening with the companies I'm running. Sometimes content takes a back seat. But today, that's not the case. This might be the biggest single news day in a while. The news cycle is insane right now in tech, especially as it pertains to first, second, and third order effects for founders. Let's get into it. Anthropic Sued the Pentagon — And Their Comp...

Databricks Overtook Snowflake. Here's Why They Should IPO Before SpaceX. 04.03.2026

Databricks has overtaken Snowflake in quarterly revenue — and Matt argues they should IPO before SpaceX does. Anduril raises $4 billion at $60 billion amid the US-Israel war with Iran. And Claude crashed under "unprecedented demand" as 700K users pledge to quit ChatGPT. In today's episode: Databricks vs. Snowflake deep dive: Tunguz revenue crossover data, the public-vs-private dynamic, and the cas...

AI Is Replacing AND Augmenting Workers. Here's the Data. 03.03.2026

Happy Monday. Three stories that tie together more than you’d think. 1Naval Ravikant: Software Engineering Isn’t Dead — It’s More Leveraged Than Ever X Post On Artificial Intelligence (Youtube) Naval dropped a post over the weekend that became the clearest articulation I’ve seen of what AI actually means for knowledge workers. Not the hype version. Not the doom version. The real version. His argum...

$110 Billion for OpenAI, 4,000 Jobs Gone at Block, and the $1.7 Billion Medicaid Fraud That Business Identity Could Have Caught 28.02.2026

Summary In this episode, Matt Parker discusses the latest in tech funding, AI advancements, layoffs, and fraud detection, providing insights into the rapidly evolving tech landscape and its implications. Keywords AI funding, OpenAI, tech layoffs, Medicaid fraud, SpaceX IPO, tech industry insights Key Topics OpenAI's massive funding round and valuation Impact of layoffs in the tech industry Medicai...

Nvidia's $68 Billion Quarter, the $109 Million AI Lobbying War, and the Fintech Infrastructure Company You've Never Heard Of 27.02.2026

Four Insights — Episode 004 | Show Notes Episode Title: Nvidia's $68 Billion Quarter, the AI Lobbying War, and the Fintech Infrastructure Company You've Never Heard Of Host: Matt Parker — Founder & CEO, ModernTax | 3x Founder Date: February 28, 2026 Runtime: ~15 minutes [0:00] Introduction & Show Overview Matt introduces the show, his background as a three-time founder and CEO of ModernTax, and pr...

Stripe Could Buy PayPal for Less Than a Quarter of Its Own Valuation 25.02.2026

Stripe x PayPal, Workday's AI Pivot, and the J-Mail Story | Four Insights 003 Description: Day 3 of the daily show. Workday funds the AI pivot but the market doesn't care. Stripe ($159B) circles PayPal ($43B) in what could be the biggest fintech M&A deal ever. And two engineers built what the DOJ said was impossible. TIMESTAMPS: 0:00 — Intro: Day 3, the Legacy Infrastructure Thread 1:30 — Workday:...

The Through Line: Banking, AI Guardrails, and the Re-Plumbing of Payments 25.02.2026

Today I've got three things: FIS earnings, Anthropic (of course) and the Pentagon, and why stablecoins are a B2B story. I also teased out my prediction for who will become the "SBF of AI" at then end .Tomorrow I will dig into Stripe at $160B potentially acquiring PayPal. Happy Tuesday. FIS Q4 Earnings (0:00–5:00) Theme: AI as Banking Infrastructure * FIS reported $2.7B in Q4 2025 revenue * 78% rec...

Earnings Week, Agentic Commerce, and the 40,000-Acre Problem 23.02.2026

Welcome to the Four Insights weekly data breakdown. Each week I’m tracking the companies, trends, and signals that matter across the ecosystems I operate in — fintech infrastructure, merchant services, lending, and AI. This is Week 9 of 2026. Let’s get into it. Big Earnings Week: FIS, Workday, Nvidia, and CoreWeave Four companies reporting this week that I’m watching closely, each for different re...

AI's Search Disruption, OpenAI's $150B Valuation, and Visa's Antitrust Battle 25.09.2024

Hey, Four Insights community, Matt Parker here, and I have missed sharing content. Let's dive into the latest developments shaking up Silicon Valley and beyond. This memo is presented by Flippa . Looking for your next big opportunity in the digital space? Check out this quickly growing fitness KDP business on Flippa: * 52 books in the fitness market * TTM revenue: $409.9K * Monthly profit: $22,264...

8 Essential Strategies for Founders & The Media War Between Tech Titans 11.09.2024

Happy Tuesday. In today's show and essay, I talk about the state of fundraising and the growing media war between All-In and Y-combinator. For more: How To Raise Millions For Your Startup in 60 Days | Youtube | Instagram In this episode, I discuss the current state of fundraising and share key strategies for founders looking to raise capital. He highlights the challenges in the current fundraising...

Venture Capital is Back 06.09.2024

episode of the End of the Day Show with Matt Parker discusses the return of venture capital funding and the focus on a specific type of founder. It also highlights two interesting fund announcements: Better Tomorrow Ventures and Slauson and Co. The episode provides insights into fundraising strategies and the importance of building a network. It concludes with a mention of the supporting sponsor,...

The Labor Day to Christmas Fundraising Sprint: Raise Millions in 90 Days 05.09.2024

Happy Wednesday. In today's show and essay, I talk about the Labor Day to Christmas sprint that exists in startups and venture capital. For more: How To Raise Millions For Your Startup in 60 Days | Youtube | Instagram The Flippa Advantage Sponsored by Flippa While you're sprinting towards your fundraising goals, don't forget about alternative paths to success. Flippa, the #1 platform to buy and se...

Flounder Mode: A Critical Look at Paul Graham's Viral Essay 03.09.2024

Happy Tuesday. In today's show, I share my thoughts on the newest meme in technology and entrepreneurship: Founder Mode. For more: How To Raise Millions For Your Startup in 60 Days | Youtube Hey! I hope you enjoyed your extended Labor Day weekend. I spent mine in the Pacific Northwest and thinking about Paul Graham's Founder Mode essay . While I agree with several points, especially for the best f...

SAFEs Dominate Pre-Seed, Twitter X's Secret Investors, and Job Market Shifts 23.08.2024

Happy Friday. In today's show, we dive into Carta’s new report on pre-seed funding in 2024, Twitter/X is forced to reveal their investors. For more: How To Raise Millions For Your Startup in 60 Days | Youtube EOD Show 019 - Detailed Podcast Show Notes Host: Matt Parker Episode Overview In this episode, Matt Parker dives into the latest trends in pre-seed funding, reveals the surprising list of Twi...

The Bolt Story: Lessons in Startup Resilience and Founder Tactics 22.08.2024

Happy Thursday! In today's deep dive, we unpacked the fascinating saga of Bolt and its founder, Ryan Breslow. This story is a masterclass in startup resilience, founder and investor tactics, and the high-stakes game of venture capital. For more: How To Raise Millions For Your Startup in 60 Days | Youtube Episode Throughout the show, we hear from our sponsors: * Quickbooks - Save 30% on Quickbooks...

Surviving the Startup Shutdown Wave: 71 Failures, 3 Funding Lifelines, and My 10% Rule 21.08.2024

Happy Tuesday! In today's show, I share Carta’s report and startup shutdowns, three funding sources founders can apply for right now, and my rule on how much of your round you should spend. For more: My Course Is Live: How To Raise Millions For Your Startup in 60 Days | Tech Billionaires' Twitter WAR Shocks Silicon Valley | Youtube In this episode, I discuss several topics related to startups and...

The Unspoken Truths: Tech Giants, Work Culture, and the Power of Words 15.08.2024

Happy Thursday! In today's show, I give commentary on Eric Schmidt’s latest comments and Michael Rubin’s comments on black culture. For more: The Founder's Fundraising Blueprint: From Cold Email to $1M in 60 Days | The $48B Fast Fashion King | Youtube Summary In this episode, Matt Parker discusses controversial statements made by two billionaires, Eric Schmidt and Michael Rubin. Schmidt, the forme...

The Coaching Revolution and AI's Data Dilemma 14.08.2024

End of the Day Show - Episode 14 Show Notes Date: August 14, 2024 (Wednesday) Host: Matt Parker Location: San Francisco Episode Summary In this episode, Matt Parker discusses two key stories shaping the tech landscape: the rise of coaching in Silicon Valley and the debate surrounding AI companies' use of Wikipedia data. Key Topics 1. The Coaching Phenomenon in Silicon Valley. Coaches become influe...

Honoring A Tech Titan, Basketball's Business Evolution, and The Cloud 100 Surges by 25% 13.08.2024

Happy Tuesday! In today's show, we honor a legend who succumbed to her two-year battle with cancer, I discuss the NBA’s future post-KD-LeBron-Steph, and The Cloud 100 2024 is worth $820 billion in market value. For more: The Founder's Fundraising Blueprint: From Cold Email to $1M in 60 Days | The $48B Fast Fashion King | Youtube Summary In this episode, Matt Parker discusses three main topics. Fir...

The $48B Fast Fashion King & YouTube's Creator Exodus 09.08.2024

Happy Friday! In today's show, we're diving into some fascinating developments that go far beyond the sports arena. From China's new e-commerce billionaire to the mass exodus of car YouTubers, there's a lot to unpack. For more: The Founder's Fundraising Blueprint: From Cold Email to $1M in 60 Days | Yesterday’s Show On The Olympics | Youtube Matt Parker 00:00 - 00:30: Introduction and show overvie...

The Creator Economy's Olympic Gold Rush, Real Estate, and More 09.08.2024

Happy Thursday. In today's show, I share some insights on what is happening at the Olympics and it does not just include the sports, millions are being earned by creators. Was anybody else on the edge of their seat with the ending of the USA vs Serbia Men’s Basketball game today? What a performance by Stephen Curry “30” For more: Top 10 Black-Led VC Funds Guide | My premium subscription to investo...

The End Of The Day Show: AI's New Kingmaker & YC's Bold Expansion Move 07.08.2024

Happy Wednesday. Matt Parker here, bringing you the hottest tech and VC news straight from the heart of Silicon Valley. Today's newsletter is packed with game-changing insights you won't want to miss, especially if you are a founder. For more: Top 10 Black-Led VC Funds Guide | My premium subscription to investor lists, course access | Youtube 🔥 Top Stories: Turing's Incredible Pivot: From Dev Sho...

The End Of The Day Show: OpenAI and The AI Downfall. 06.08.2024

Happy Tuesday. In today's show, we dive into the latest upheaval in Silicon Valley. OpenAI, the AI powerhouse behind ChatGPT, is facing a significant brain drain as three more executives, including co-founder John Schulman, head for the exit. Adding fuel to the fire, Elon Musk is renewing his lawsuit against the company he helped create. For more: Top 10 Black-Led VC Funds Guide | My premium subsc...

The End of the Day Show: Google Snaps Up Character AI: A Win for Big Tech? 02.08.2024

Happy Friday! Today’s show is a special one as we had some big news during our recording. Another heavily funded AI company is getting acquired by big tech. This time it is Character.ai and their founders heading back to Google. For more: Top 10 Black-Led VC Funds Guide | My premium subscription to investor lists, course access | Youtube Brought to you by: * First Meeting — Tracking enterprise AI...

The End of The Day Show: Fundraising Mastery: Lessons from a $7.5M Seed Round 01.08.2024

Hey there! I'm Matt Parker and welcome to the latest edition of The End of the Day Show and accompanying newsletter. Four days a week, I break down the hottest stories in tech, startups, and venture capital, providing insights you won't find anywhere else with my commentary, scoops, and stories. From AI breakthroughs to fundraising strategies, we've got you covered. For more: Top 10 Black-Led VC F...

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