PODCAST · business
Four Insights With Matthew Parker
by Matthew Parker
Four Insights is a show from Matthew Parker — founder & CEO of ModernTax — on AI, markets, and how money actually moves. Operator-level breakdowns of the week's biggest deals, contrarian calls (and the receipts when they land), plus occasional interviews with founders and operators. stretchfour.substack.com
Episodes
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Anthropic Is Suing the Pentagon. OpenAI and Google Are Backing Them.
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…
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Databricks Overtook Snowflake. Here's Why They Should IPO Before SpaceX.
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:...
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AI Is Replacing AND Augmenting Workers. Here's the Data.
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…
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$110 Billion for OpenAI, 4,000 Jobs Gone at Block, and the $1.7 Billion Medicaid Fraud That Business Identity Could Have Caught
SummaryIn 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. KeywordsAI funding, OpenAI, tech layoffs, Medicaid fraud, SpaceX IPO, tech industry insights…
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Nvidia's $68 Billion Quarter, the $109 Million AI Lobbying War, and the Fintech Infrastructure Company You've Never Heard Of
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...
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Stripe Could Buy PayPal for Less Than a Quarter of Its Own Valuation
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...
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The Through Line: Banking, AI Guardrails, and the Re-Plumbing of Payments
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...
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Earnings Week, Agentic Commerce, and the 40,000-Acre Problem
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,...
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AI's Search Disruption, OpenAI's $150B Valuation, and Visa's Antitrust Battle
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...
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8 Essential Strategies for Founders & The Media War Between Tech Titans
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...
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Venture Capital is Back
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...
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The Labor Day to Christmas Fundraising Sprint: Raise Millions in 90 Days
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...
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Flounder Mode: A Critical Look at Paul Graham's Viral Essay
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…
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SAFEs Dominate Pre-Seed, Twitter X's Secret Investors, and Job Market Shifts
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...
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The Bolt Story: Lessons in Startup Resilience and Founder Tactics
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 |...
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Surviving the Startup Shutdown Wave: 71 Failures, 3 Funding Lifelines, and My 10% Rule
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...
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The Unspoken Truths: Tech Giants, Work Culture, and the Power of Words
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…
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The Coaching Revolution and AI's Data Dilemma
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…
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Honoring A Tech Titan, Basketball's Business Evolution, and The Cloud 100 Surges by 25%
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...
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The $48B Fast Fashion King & YouTube's Creator Exodus
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…
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The Creator Economy's Olympic Gold Rush, Real Estate, and More
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…
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The End Of The Day Show: AI's New Kingmaker & YC's Bold Expansion Move
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...
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The End Of The Day Show: OpenAI and The AI Downfall.
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...
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The End of the Day Show: Google Snaps Up Character AI: A Win for Big Tech?
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…
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The End of The Day Show: Fundraising Mastery: Lessons from a $7.5M Seed Round
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....
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The End of The Day Show: Silicon Valley's Latest: Viral AI Launches and Tech Giant Earnings
Hey there, tech enthusiasts! Today's End of The Day Show packed a punch with some eye-opening stories: Brought to you by: * First Meeting — Tracking enterprise AI budgets, spending patterns, and decision-making processes. * OpenPhone —brings your business calls, texts, and contacts into one...
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The End of The Day Show: Humane AI firesale, Big Tech Tumbles, Small Caps Surge, and the Millionaire Next Door
Hey there, tech enthusiasts! Today's End of The Day Show packed a punch with some eye-opening stories: Brought to you by: * First Meeting — Tracking enterprise AI budgets, spending patterns, and decision-making processes. * OpenPhone —brings your business calls, texts, and contacts into one...
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The End of the Day Show: Earnings Preview, AI in Focus, Carvana Turnaround, Enterprise Sales, and Powder Raises $5M
Welcome to this week's tech news roundup, brought to you by Matt Parker's "The End of the Day Show". Let's dive into the biggest stories and insights from the tech world. 🚀 Earnings Season Countdown Big week ahead as we enter earnings season for notable tech companies. Here's what to watch: *...
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The End of the Day Show: Tech Beefs, Streaming Deals, and Another Security Unicorn
Hey there, tech enthusiasts and startup mavens! Welcome to this week's roundup of "The End of the Day Show". We've got a spicy mix of Silicon Valley drama, sports business, and unicorn births. Let's dive in! 1. Silicon Valley Soap Opera: Sacks vs. Conrad The tech world's latest Twitter drama is...
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The End of the Day Show: Billionaires, Political Donations, and Tech Drama
Hey there, tech enthusiasts and startup mavens! Welcome back to "The End of the Day Show" newsletter. Today's episode was a rollercoaster of billion-dollar deals, political intrigue, and some good old-fashioned Silicon Valley drama. Let's dive in! * 📺 YouTube: FourInsights * 📸 Instagram:...
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The End of the Day Show: Quitting, AI Deals, and Legal Tech Disruption
Hey there, Yesterday, I decided to launch a new daily show "The End of the Day Show.” Yesterday's episode was packed with insights on quitting, big tech acquisitions, and the booming legal tech industry. Let's dive in! * 📺 YouTube: FourInsights * 📸 Instagram: @FourInsights * 🌳 LinkTree:...
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Episode 024: AI Licensing, Elon, and IPOs: Unraveling Silicon Valley's Biggest Moves
In today's show, I'll be discussing the latest updates from Silicon Valley last week. We'll delve into how content platforms are planning to monetize through licensing deals, Sequoia's investment in another Elon company, and some insider information on Figma's significant tender offer....
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Episode 023: Is OpenAI a Startup Killer? Shaun Maguire, AI Showdowns, and Top VC Podcasts
In today’s show I discuss the competition between OpenAI and Google in the field of artificial intelligence (AI). I discuss the questions from last week are whether OpenAI is a threat to startups and explores the potential winners and losers in the AI landscape? I also shares insights from an…
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Episode 022: The Private Market Boom, Ramp's AI Spending Report, and Mermaid Chart's Oversubscribed $7.5M Seed Round
In this episode of the Stretch Four podcast, host Matt Parker dives into the latest developments in the tech world, including the booming market for private company shares, the rise of AI spending among businesses, and an exclusive interview with Andrew Firestone, CEO of Mermaid Chart. Throughout...
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Episode 021: How to Build a Billion Dollar Analytics Company (Twice): Lessons from Repeat Founder Colin Zima
The episode is brought to you by ModernTax — Providing comprehensive business data coverage with AI-powered tools. Want more insights from top tech founders like Colin Zima? Check out the full video interview from the Stretch For Podcast now live on our YouTube channel. Here are the show notes…
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Episode 020: Demo Perfection and the Pitfalls of Falling Out of Love With Your Company
The episode is brought to you by ModernTax — Providing comprehensive business data coverage with AI-powered tools. Demo Perfection and the Pitfalls of Falling Out of Love With Your Company" - Insights from Dan Siroker, CEO and Founder of rewind.ai, on building self-serve products and navigating…
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Episode 019: Building an AI Startup from Humble Beginnings: A Founder's Immigration Journey
This week on the podcast I have a very special guest. In this podcast episode, I interviewed Surbhi Rathore, CEO and co-founder of Symbl.AI, a machine learning startup based in San Francisco. [00:00] The episode begins with a discussion on the challenges of being an immigrant founder in the US…
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Bonus Pod: 48 Hour Fast: Insights and Challenges with Vidal Nelson
In this emergency episode, we discuss the 48-Hour Fast I participated in. This was my first time trying a prolonged fast. To get into why I think it is important besides heading towards 36 and not trying to get too much of a dad bod, I brought on a previous guest Vidal Nelson who organized the…
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Episode 018: Running for My Life (My SF Half Marathon Results), Bolt Goes Bust, Fundraising Framework For Founders
Welcome back everyone to another episode of the Stretch Four Podcast, this week’s show I recap my performance at the San Francisco Marathon (my first Half Marathon), where he ran a competitive race with surprisingly good weather. I also discuss new stories about Bolt, which I have written about...
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Episode 017: Building a VC-Backed Telehealth Company with Dan Miller, CEO of Spora Health
Welcome back to the Stretch Four Podcast, Today, I am thrilled to have Dan Miller, the Chief Executive Officer and founder of Spora Health, joining us on the show. Dan has an impressive background as a three-time serial entrepreneur and one of the few Black Americans to successfully raise over $1...
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Episode 016: Not at Vegas Summer League: Urgency in July, Inspiration from Your Kids, and More
Welcome back to the Stretch Four Podcast. This is Episode 16 of the podcast! This week, we're coming to you from San Francisco instead of the NBA Summer League in Vegas. We'll discuss the importance of having urgency, inspired by a recent podcast I listened to with Frank Slootman as a guest and…
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Episode 015: Time Management and Building Relationships with Yoni Rubin (MRGN)
In this episode of the Stretch Four Podcast, I cover a range of topics, including founder insights and the importance of building relationships and understanding the nuances of different geographies. Specifically, I discussed my recent trip to the OnRamp insurance conference in the Midwest (where…
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Episode 014: Mistral AI's $130M seed round, importance of reference customers, and interview with PostHog founder James Hawkins.
Happy Tuesday, Welcome back to another episode of the Stretch For Podcast! Reporting live from Saint Paul, Minnesota, as I am here for a conference. In this week’s episode, I cover a variety of topics, including the recent news about Mistral AI, a company that raised $130 million in seed funding.…
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Episode 013: Tech Week Recaps (SF & LA)
In the latest episode of the Stretch Four Podcast, I shared my experiences at LA Tech Week and SF Tech Week. Over the course of two weeks, I attended a variety of events and met some amazing people in the industry. I highlighted two events in particular: the Stox Times a16z Demo Day for…
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Episode 012: MoonPay Founders Sell Shares, Plaid's Data Collection, and New Business from Laundry with Scott Patterson.
In this episode, Matthew Parker talks about MoonPay's $150M secondary and Plaid's screen-scraping empire. Matt also interviews T. Scott Patterson, Founder & CEO of Tumble, a laundry service serving multi-family properties. Thanks for tuning in to our latest episode with Matt Martin, CEO of...
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Episode 011: Finovate Insights, Plastic Bankruptcy, and Staying Fit as a Parent plus Clockwise Founder/CEO Matt Martin
Welcome back to the Stretch For Podcast, where we talk about the highs and lows of being an early-stage startup founder, as well as fitness, health, and parenting. In this episode, I share my experience at the FinovateSpring conference and discuss the importance of getting your product out to...
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Episode 010: The Newchip Accelerator bankruptcy and Tanvi Surti of Luca.AI discussing E-commerce, AI, and YCombinator.
On this episode of the Stretch Four Podcast, Tanvi Surti, founder of Luca, joins the show to discuss e-commerce, AI, and YCombinator. Before that, I start the show off by discussing the bankruptcy of the Newchip Accelerator with former mentee and founder Yoni Rubin. He shares his experience with...
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Episode 009: Faking it in Silicon Valley, who paid DataDog $65M in one year, and talking wellness with friend and fitness influencer Vidal Nelson
Hey everyone, We are back at it again with episode 008 of the Stretch Four podcast, on this week’s show, I interviewed a good friend who I have known since college. Vidal Nelson, also known as Phewchi on Instagram and to his inner circle is a lifestyle health and wellness expert and influencer.…
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Episode 008: The Journey to Radical Optimism: Insights on Family, Personal Branding, and Future Technology with Kevin Kelly
Hey everyone, In this episode of the Stretch For Podcast, we have a very special guest, Kevin Kelly, the founding editor of Wired Magazine and author of multiple books including "The Inevitable" and "Out of Control". Kevin shares his insights on entrepreneurship, innovation, and the future, as…
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Episode 007: CEO Interview with Ben Lilienthal (Screen Meet) on Building Four Successful Enterprise Startups, Time Billionaire Parenting, Air Movie Recap, and Silicon Valley's Diversity Problem
Ready to take the next step in your hiring journey? You’ve found the global talent but need to onboard them. Deel can help. Our expert teams can guide you to hiring quickly and compliantly in over 150 countries at your fingertips with compliant contracts, top local legal experts, global payroll...
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ABOUT THIS SHOW
Four Insights is a show from Matthew Parker — founder & CEO of ModernTax — on AI, markets, and how money actually moves. Operator-level breakdowns of the week's biggest deals, contrarian calls (and the receipts when they land), plus occasional interviews with founders and operators.
stretchfour.substack.com
HOSTED BY
Matthew Parker
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How many episodes does Four Insights With Matthew Parker have?
Four Insights With Matthew Parker currently has 56 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Four Insights With Matthew Parker about?
Four Insights is a show from Matthew Parker — founder & CEO of ModernTax — on AI, markets, and how money actually moves. Operator-level breakdowns of the week's biggest deals, contrarian calls (and the receipts when they land), plus occasional interviews with founders and operators....
How often does Four Insights With Matthew Parker release new episodes?
Four Insights With Matthew Parker has 56 episodes. Check the episode list to see recent publication dates and frequency.
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You can listen to Four Insights With Matthew Parker on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Four Insights With Matthew Parker?
Four Insights With Matthew Parker is created and hosted by Matthew Parker.
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