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Stretch Four Podcast

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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, second, and third order effects for founders. Let's get into it.Anthropic Sued the Pentagon — And Their Competitors Are Standing Behind ThemThe Anthropic-Pentagon story just escalated to a new level. Anthropic filed two federal lawsuits yesterday — one in Northern California, one in DC — alleging the supply-chain risk designation violates their First Amendment rights and exceeds the scope of law. They’re seeking a temporary restraining order to keep working with military partners while this plays out.The massive development: 30+ OpenAI and Google DeepMind employees filed an amicus brief supporting Anthropic. Among the signatories — Jeff Dean, Google’s chief scientist and the leader of the Gemini AI program.The brief is blunt: the government’s designation was “an improper and arbitrary use of power that has serious ramifications for our industry.” The Pentagon could have simply cancelled the contract and hired another AI company. Instead, they weaponized a national security label to punish a private company. Even Sam Altman, who literally took the $200 million Pentagon deal that Anthropic lost, called this “very bad for our industry.”Here’s the thing I want to say to founders. This actually affects early-stage startups. Your political ties, your political positions are really, really important in how your product is commercially used. I work in an industry where things are regulated. We have a large government agency — the SBA — that oversees how our commercial partners provide services. It’s better to be on the side of the political institution because that gives you the benefit of the doubt when you bring services to market.Church and state are very integrated in business right now. Your political affiliation, your religious affiliation — all of it is part of how you’re judged as a builder. That’s just reality. I grew up on the principle that church and state are things you stay away from in business. That’s over.Anthropic has been the lone soldier among the big companies that hasn’t bowed down to Trump. Everyone else went MAGA in the past 18 months. Dario has been outspoken — he’s not from that ilk. He’s not giving money, not showing up at events. And now there are real ramifications. The supply-chain risk designation is going to cause a trickle-down effect. It’s going to slow the business in the short term.And here’s the part nobody wants to say: competitors will support Anthropic in court while taking the opportunity in the market. OpenAI already took the $200 million contract. Google will probably lean into whatever the military needs. The industry is standing behind Anthropic because this shouldn’t be happening, but the reality is that business moves on.Anthropic isn’t going anywhere. But this will probably go into litigation for a while.Oracle Reports Tonight — And the Pressure Is RealOracle’s reporting after the bell today, and their AI cloud numbers will tell us a lot about whether this infrastructure buildout is real or hype.I’ve been reading a book on Dario Amodei, and the biggest thing to understand about the AI story is that these companies are built around access to compute. The more data centers, the more compute, the more power — the better. That’s how it works. That’s the reality of why these companies are building out massive infrastructure.But Larry Ellison is under pressure. Oracle has more than $100 billion in debt and massive layoffs as they push ahead with this transformation. Expected numbers: $16.9 billion in revenue, cloud up 43% to $8.9 billion. That cloud number represents a historic shift. Oracle used to be an on-prem database company. Now cloud is more than half the business. There’s a learning lesson here for every startup: you have to always be reinventing yourself, especially in the AI-first market. What you were a year ago may not be what you are today.The capex numbers are staggering: $50 billion expected this year. Q3 alone, $14 billion, up 139%. And their Stargate initiative with OpenAI appears to be scaling back. The Information has reporting on why OpenAI walked away from the Stargate expansion in Albany.Oracle’s stock tells the story of the market’s uncertainty. Down 54% over six months. Flat over the past year. Up 125% over five years. The AI bet is massive, but the market is nervous about whether $300 billion in commitments upfront is justified for something we don’t know the full scale of yet.Mira Murati Hit Back — A Gigawatt of Nvidia and a Comeback StoryMira Murati is back in the news. And this time, it’s a good story.The background: she’s 37, ex-CTO at OpenAI, previously at Tesla. She founded Thinking Machines Lab, raised $2 billion out the gate at a $12 billion valuation — no

Mar 10, 202624 min

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:Databricks vs. Snowflake deep dive: Tunguz revenue crossover data, the public-vs-private dynamic, and the case for being the first IPO of 2026Anduril's $4B raise: war context, Trae Stephens shoutout, and the irony of Anthropic being banned while their tools are used at warClaude demand surge: the outage, ChatGPT exodus numbers (295% uninstalls, 775% one-stars, 700K cancellation pledges), and why the product speaks for itselfA personal note on Americans stuck in Dubai and the human cost of what's happeningSound bites: "It's kind of weird to see private companies get so big they're trolling public companies." "The people are speaking." "I've voted with my pocketbook."Sources: Tomasz Tunguz (Theory Ventures), Bloomberg, Reuters, TechCrunch, CNBC, Sensor TowerTomorrow: SpaceX confidential IPO (timing TBD — Elon's the master marketer)Host: Matt Parker | Newsletter: stretchfour.substack.com | Presented by ModernTax (moderntax.io) Get full access to Four Insights at stretchfour.substack.com/subscribe

Mar 4, 202615 min

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 EverX PostOn 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 argument: software engineers are now among the most leveraged people on earth. Not because they write code — AI writes code. Because they think in code. They understand what’s happening underneath. And all abstractions are leaky.I’ve lived this. As a non-technical founder who’s been building with Claude Code and these tools, the bottleneck is exactly what Naval describes: understanding what’s happening underneath the platforms, writing the correct specs, knowing when the AI got something wrong. A strong software engineer isn’t just writing code anymore — they’re writing product specs that AI tools can actually execute on. And they’re catching the bugs, the suboptimal architecture, the leaky abstractions that every AI-built product ships with.Naval draws a distinction that matters enormously: codified knowledge versus tacit knowledge. Codified is what you learn from textbooks. Tacit is what you learn from experience. AI replicates the first. It cannot replicate the second.Companies are still hiring software engineers because even if 90% of your code is written by an AI agent, the people prompting those agents and creating those specs have a massive advantage if they’re strong engineers. At the worst, software engineers become the people who fix the problems AI agents create. That’s not replacement. That’s leverage.The uncomfortable punchline: “There is no demand for average.” But the set of things you can be best at is infinite. “Become the best in the world at what you do. Keep redefining what you do until this is true.”I see this every day at ModernTax. We build voice agents handling codified, repeatable workflows with government services. But we also have a human component — enrolled agents doing the work. The AI tools help those experienced agents do their jobs better. The more trained and experienced an agent is, the better they perform with the technology. AI amplifies expertise. It doesn’t replace it.Claude Hit #1 on the App Store — And Nobody Expected What Happened NextI woke up Monday morning and everybody was talking about Claude. It’s down, it’s back up, but look at these numbers.The free app rankings tell the whole story: Claude is #1. ChatGPT is #2. Google Gemini is #3. AI has completely taken over the top of the App Store. When you see these three at the top of a global ranking, you understand the sheer scale of what’s happening. This isn’t Silicon Valley in an echo chamber. This is global adoption.Anthropic went from #42 in the App Store in January to #1 over the weekend. Not purely product — the Super Bowl commercials helped, but the real catalyst was the Pentagon standoff.Here’s what happened. Anthropic has a $200 million contract with the Department of War. The Pentagon demanded unrestricted use of Claude’s AI models, including for surveillance and autonomous weapons. Dario Amodei, Anthropic’s CEO, said no. The political fallout was immediate: Trump called Anthropic “radical left,” Defense Secretary Hegseth designated them a “supply chain risk to national security,” and OpenAI jumped in to replace Anthropic on the deal.And then the opposite of what the administration expected happened. #CancelChatGPT went viral. Claude’s downloads surged. The attempt to punish Anthropic turned into the best marketing campaign they never paid for.There’s a political parallel here that I can’t stop thinking about. Remember 2016? The more liberal and progressive media attacked Trump, called him names, said he was a bad candidate — and it helped his popularity. There’s a correlation with this. The more this administration targets Claude, the more publicity and public support Anthropic gets. The Streisand effect in real time.My position: I use Claude constantly. It’s one of the best model companies. When you think about Coworking, Claude Code, all these tools — they’re phenomenal and everyone’s using them. Nobody is going to stop. And this weekend proved it.The Dallas Fed: AI Is Replacing AND Augmenting Workers — But I Think Companies Are Getting It WrongThe Dallas Fed put out a paper that does something most AI hot takes don’t: it looks at real data. Real wages. Real employment numbers. Not doom and gloom — economics.The findings confirm what Naval said, but with numbers. US employment is up 2.5% since ChatGPT launched. But in the top 10% of AI-exposed sectors, employment is down 1%. Computer systems design is down 5%.The decline is hitting young workers hardest — under 25 specifically. Not because of layoffs. Because of a collapsed job-finding rate. Companies just aren’t hiring entry-level in these fields.But wages in those sam

Mar 3, 202616 min

$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 insightsKey TopicsOpenAI's massive funding round and valuationImpact of layoffs in the tech industryMedicaid fraud detection using data analyticsSpaceX's confidential IPO plansThe role of AI in business productivity and fraud preventionGuest NametitlesOpenAI's $110 Billion Funding Round: What It Means for TechThe Future of AI: Insights from the Latest Funding and InnovationsSound Bites"Relevancy is lasting shorter and shorter""AI is making companies more productive and reducing staff""$1.7 billion in Medicaid payments went to fraud networks"Chapters00:00 Intro and Market Sentiment: Tech in a Year of Rapid Change01:16 OpenAI's Record-Breaking $110 Billion Funding Round07:27 Block's Massive Layoffs and Stock Surge10:42 Medicaid Fraud Report by Middesk: Insights and Implications13:38 Upcoming SpaceX IPO and Market Outlook15:11 Closing Remarks and Future Content* Email: [email protected]* LinkedIn: Matt Parker* X: @mattaparker: https://x.com/mattaparkerYoutube: https://www.youtube.com/@FourInsightsSubscribe if you haven’t. Share this with someone who needs the operator lens on what’s happening. I’m Matt Parker. This is Four Insights. See you Monday. Get full access to Four Insights at stretchfour.substack.com/subscribe

Feb 28, 202616 min

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 NotesEpisode Title: Nvidia's $68 Billion Quarter, the AI Lobbying War, and the Fintech Infrastructure Company You've Never Heard OfHost: Matt Parker — Founder & CEO, ModernTax | 3x FounderDate: February 28, 2026Runtime: ~15 minutes[0:00] Introduction & Show Overview Matt introduces the show, his background as a three-time founder and CEO of ModernTax, and previews the three segments: Nvidia earnings, AI policy and lobbying, and a deep dive on Column.[1:30] Segment 1 — Nvidia's $68 Billion Quarter & China Chip Standoff Nvidia posted $68.1B in Q4 revenue, up 73% YoY. They received a US license to export H200 chips to China, but the CFO confirmed zero chips have been sold. CoreWeave's $67B in backlogged bookings signals a supply chain bottleneck. Square's 4,000 layoffs and 24% stock jump illustrate AI's displacement of knowledge work. Matt discusses the shift from "is AI real" to "who controls the supply chain" and connects it to infrastructure geopolitics.[7:30] Advisory CTA Matt invites listeners and readers who are building or allocating in AI infrastructure to compare notes on supply chain risk. Reply with "NVIDIA" or email [email protected].[8:00] Segment 2 — The $109 Million AI Lobbying War Tech and AI companies spent $109M on lobbying in 2025—a record. Meta led at $26M+, Nvidia increased 7x to $4.9M. The $100M Leading the Future super PAC (a16z, Greg Brockman, Ron Conway, Joe Lonsdale, Perplexity) is targeting 2026 midterm candidates. David Sacks serves as White House AI czar. Matt connects this to his public policy background and recommends The Wolves of K Street. He argues that regulatory frameworks are competitive moats in regulated industries.[11:00] Premium CTA Matt previews an upcoming premium breakdown on AI regulatory frameworks, key players, and implications for founders and investors. Reply with "PREMIUM" for early access.[11:30] Segment 3 — Column: The Most Important Fintech Company You've Never Heard Of Alex Conrad at Upstarts Media profiled Column—William Hockey's (Plaid co-founder) fintech infrastructure company. Key numbers: $200M revenue, $100M free cash flow, 110 employees, zero VC, ~$6B estimated valuation. Powers Bilt, Brex, Ramp, Mercury, Wise, and Plaid. Controls ~40% of Bay Area tech money movement. Matt discusses Hockey's second act, the personal details revealed in the profile, and how Column fits into the broader fintech infrastructure thesis and the "financial Cold War" between the US and China.[14:30] Close Sponsorship mention and sign-off. Matt invites operators, engineers, and companies building in AI infrastructure, fintech, or developer tools to connect at [email protected].* Email: [email protected]* LinkedIn: Matt Parker* X: @mattaparker Get full access to Four Insights at stretchfour.substack.com/subscribe

Feb 27, 202614 min

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 003Description: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: AI Revenue Hits $400M, Market Still Punishing 5:30 — PayPal: $1.75T in Transactions, 82% Off Its Peak 9:00 — Stripe's Play: $159B Buying $43B 11:00 — Reducto & J-Mail: Parsing What the DOJ Couldn't 14:00 — Closing: What Would You Do With PayPal?SOURCES & CREDITS:Workday earnings: App Economy Insights / How They Make Money (Substack)Bloomberg: Stripe Considers PayPal Acquisition (Feb 24, 2026)Sheel Mohnot (@pitdesi) — Better Tomorrow VenturesThe Verge: AI PDF parsing / ReductoReducto (reducto.ai) — YC 2024J-Mail projectFIS earnings: ModernTax Daily Beat (Feb 24, 2026)SUBSCRIBE: https://stretchfour.substack.com ModernTax Daily Beat: https://moderntax.substack.com Website: https://moderntax.io🔗 Follow AlongYouTubeLinkedInX (Four Insights)X (Matt Parker) Get full access to Four Insights at stretchfour.substack.com/subscribe

Feb 25, 202618 min

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 Earnings (0:00–5:00)Theme: AI as Banking Infrastructure* FIS reported $2.7B in Q4 2025 revenue* 78% recurring revenue, serves 14 of top 25 US banks* Predicting 4X AI spend in 2026, targeting 8X industry AI adoption vs. 2023* New AI transaction platform launched* Stock flat — which for a legacy company in this market is actually fine* Bridge to payments: Stripe letter (and so did Checkout.com) dropped today — $160B valuation (up from $92B). Stripe potentially acquiring PayPal will be talked about tomorrow. PayPal down 37% in past year, with a new CEO starting March 1.“If you’re a public company, it just behooves you to speak about AI in some capacity. But it’s very interesting for these companies where they tend to adopt new technology slower.”AI Guardrails & National Security (5:00–12:00)Theme: Who Sets the Rules When AI Is Strategic Infrastructure?* Dario Amodei (Anthropic CEO) in active conversations with Pentagon about model access* This mirrors what’s happening at consumer level — many sites blocking Claude/MCP agents for various reasons. But in this case Anthropic is setting boundaries on where it will go with and the Pentagon is pushing back on the AI guardrails.* The repeating question: who governs when AI becomes strategic infrastructure?* My IRS parallel: government services + AI = massive policy questions* People using Claude/GPT for taxes with minimal regulation* Anthropic’s political positioning vs. current administration creating friction* Supply chain risk in AI becoming a policy issue* Anthropic + IBM / COBOL teaser — we will do a deeper dive on this likely on the ModernTax channel“It’s not a surprise that Anthropic is going through this and not OpenAI because Anthropic has been outspoken against the current administration.”Stablecoins as B2B Payment Infrastructure (12:00–18:00)Theme: Stablecoins Aren’t a Crypto Story — They’re a Payments Infrastructure Story* Continuing from yesterday’s Citrini report breakdown* Your personal experience: paying 2.5% on payment processing fees, looking for alternatives* The real opportunity is B2B, not consumer: settlements, marketplaces, creator payouts, remittances, cross-border* Hour-long conversation with risk manager at major payment processor — cross-border payments, programmable payouts, platform distribution* $1.75 trillion in annual payroll taxes — what happens when AI reshapes where that revenue comes from?“Every time you process a payment and you’re paying 2.5%, if you’re a business owner, it has to hurt your soul.”The Through Line & Predictions (18:00–20:00)Theme: Connecting the Dots* The through line: banking margins are being compressed from every direction — AI agents, stablecoins, new entrants* Enterprise agents are coming, but adoption outside Silicon Valley is much slower* Compliance perimeter expands as infrastructure moves off traditional rails* “Who’s going to be the SBF of AI?” — legal repercussions are coming* Mentor quote: “Every day I’m trying to make investments I won’t be embarrassed of in a year”* Teaser: Founders who get product into enterprise hands before vendor procurement catches up are winning right nowFour Insights is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.📚 Resources & Links* ModernTax* Clearfirm🔗 Follow Along* YouTube* LinkedIn* X (Four Insights)* X (Matt Parker) Get full access to Four Insights at stretchfour.substack.com/subscribe

Feb 25, 202620 min

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, Nvidia, and CoreWeaveFour companies reporting this week that I’m watching closely, each for different reasons.FIS reports Q4 earnings tomorrow. FIS has been a pretty flat stock, but that’s not why I care about them. They provide a window into what’s happening with U.S. merchants — transaction volumes, payment trends, and the health of the businesses we serve through both ModernTax and Clearfirm. Their report is less about the stock price and more about the signal it sends about where merchant activity is heading.Workday is in trouble — or at least, the market thinks so. Down 7% today, down 38% year-to-date. This isn’t just a Workday story. It’s the broader question of what happens to SaaS companies when AI starts eating into their value propositions. Workday sits in HR tech, which is a space we touch through ModernTax’s service lines. The question I keep coming back to: if AI agents can handle the workflows these platforms were built to manage, what exactly are customers paying for? We’ll get into their numbers when they drop.Nvidia reports this week too. The stock has been flat year-to-date, which is notable given the 1,200% run over the past five years and 46% gain over the trailing twelve months. The questions are starting to pile up around the sustainability of the AI infrastructure buildout — which connects directly to the last topic I’ll get to. When Nvidia reports, I’m less interested in the headline number and more interested in what they say about customer concentration and forward demand.CoreWeave also announces this week. Same theme — who’s taking on the capital risk for this massive AI infrastructure buildout, and who’s on the hook for delivering the compute? Their numbers will tell us a lot about whether the buildout is accelerating or hitting friction.The Viral Post: Citrini’s 2028 Global Intelligence Crisis ReportIf you were on X this weekend, you probably saw it. Citrini Research dropped a research piece that’s already at 6.1 million views, 399 reposts, and climbing. Every major tech beat writer is covering it. They described it as “a scenario, not a prediction” — and said dismissing it outright “requires the kind of intellectual laziness that tends to get expensive.”I’m not going to summarize the whole thing — you can read it on their Substack — but the parts that caught my attention are directly relevant to what we do.The agentic commerce thesis is real. The report breaks down a comparison that I think about constantly: traditional payment rails versus agentic stablecoin transactions. Here’s the math:In the traditional model, a $100 purchase costs the merchant roughly $2.50 in fees. The issuing bank takes 1.7–2%, the network takes about 15 basis points, and the acquiring bank takes 3–5 bips. The merchant receives $97.50.In the agentic stablecoin model, that same $100 gets routed by an agent via USDC on Solana or an L2. Total cost: one cent flat. The merchant receives $99.99 — with instant settlement.This is the part that should make anyone in payments pay attention. We use Stripe for both of our businesses, and I’m always looking for ways to avoid those 2.5–3% fees. ACH helps, but it’s slow. Stablecoin rails solve for both cost and speed simultaneously.The broader implication: this isn’t just about SaaS companies getting disrupted. This is about Amex, Stripe, Visa — companies that make their money in that 2–3% merchant fee layer — facing a fundamentally different cost structure. If agents are routing transactions and optimizing for the cheapest rail in real time, the entire payment stack gets repriced.On Citrini themselves: I hadn’t heard of them much before this, but they’re now the #1 finance publication on Substack. They’re charging $125/month for their research, with a bundle at $2,000/month. That’s a serious content business built on the back of deep research and strong distribution. Worth studying as a model.The 40,000-Acre Problem: AI’s Physical ConstraintsThis is the story that got me thinking differently this week.The Guardian ran a piece on U.S. farmers rejecting multimillion-dollar data center bids for their land. The headline number: there’s a projected 40,000-acre deficit for data center development globally over the next five years, according to a September 2025 report from JLL. That’s double the roughly 20,000 acres currently in use.We think about AI as this purely digital, online thing. But when you break it down to first principles, the entire AI buildout runs on three physical inputs: land, power, and water. And all three require financing and permitting — which is exactly the world I live in.I own some rural property back where I grew up. This article actually has me doing math on w

Feb 23, 202610 min

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 business on Flippa:* 52 books in the fitness market* TTM revenue: $409.9K* Monthly profit: $22,264* 68% profit marginVisit Flippa.com for more exciting business opportunities like this and others!AI Reshaping SearchOne of the most intriguing stories this week comes from a report by The Information dating back to September 19th. It highlights how AI tools are displacing traditional web searches, which could have a drastic impact on how startups market their companies in the future. To even understand why AI chatbots have become so important is simply to realize that Google/Alphabet generated $48.5 billion in revenue on search in Q2 2024. This is their core business that pays for everything else, and ChatGPT and Perplexity-like apps are chipping away at this even if it is minuscule it has the potential to be a massive opportunity. Key findings:* 25% of respondents are using traditional search engines less due to generative AI* 40% reported using search engines 0-25% less* Top AI displacers: ChatGPT (76%), Perplexity (37%), Google's Gemini (36%)As a founder and content creator, I'm particularly interested in how this shift affects our ability to find credible information and reach our target audiences. This will be an ongoing development and I expect to see more and more innovation from all players including Google, who will likely stop at no costs to defend their search dominance at all costs.OpenAI's Record-Breaking Funding RoundSam Altman and OpenAI are making waves again with a potential $6.5 billion funding round, valuing the company at a staggering $150 billion. This would make OpenAI the second most valuable private company globally, behind only ByteDance (TikTok's parent company).The big question on everyone's mind, or at least mine: Will Sam Altman finally become a stakeholder in OpenAI? It's unusual for a CEO of such a valuable company to not have equity, especially in Silicon Valley where founder ownership is the norm. It feels so weird that Altman is not a shareholder with the tablestakes rising by the month. Sure Sam lives in a $30M home in Russian Hill, has a weekend ranch in Napa, and seemingly has a mult-million dollar car collection alone, but something is simply unsettling about him not being on the cap table.Visa Faces Antitrust LawsuitThe Justice Department is suing Visa, alleging monopolistic practices in the payment processing industry. With Visa controlling about 60% of debit card transactions in the US, this case could have far-reaching implications for the fintech sector.Key allegations:* Visa punishes customers for using competing services* The company coerces fintech firms to work exclusively with themAs someone who's been in the fintech world for seven years, I find this case fascinating. Visa's profitability per employee is astronomical, outperforming even its closest competitors. This lawsuit could potentially open up the market for new players in the payment processing space.These are just a few highlights. Listen to the rest of the episode for more insights on how these developments could impact startups and the tech ecosystem at large.This newsletter is also brought to you by Diginius.Whether you're looking to optimize your PPC campaigns or need help finding the right marketing agency, Diginius has you covered. Their platform offers powerful tools for digital marketing automation and analytics.For Four Insights listeners and readers, get a special 14-day free trial of Diginius. That's all for this edition! Don't forget to check out the latest episode of Four Insights on YouTube, where we dive deeper into these topics and more.Stay curious, Matt Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Sep 25, 202418 min

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 | InstagramIn 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 market, such as increased selectivity from investors and longer fundraising cycles. I also provide eight strategies for founders, including preparing for a long fundraising cycle, casting a wide net, and creating urgency and momentum. In the second part of the episode, I talk about a growing rift between Paul Graham and David Sacks, two prominent figures in the venture capital world. He explores the drama and tensions between them, highlighting their different perspectives and successes.Sponsored by FlippaWhile you're sprinting towards your fundraising goals, don't forget about alternative paths to success. Flippa, the #1 platform to buy and sell online businesses, offers opportunities for both buyers and sellers in the tech ecosystem. Whether you're looking to acquire a promising startup or considering an exit strategy, Flippa provides a marketplace to explore your options.Takeaways* The current fundraising market is more challenging, with increased selectivity from investors and longer fundraising cycles.* Founders should prepare for a long fundraising cycle and optimize for a 60 to 90-day process.* Casting a wide net and creating urgency and momentum are important strategies for fundraising success.* Protecting the pitch and materials, being persistent with follow-ups, and considering alternative funding sources are also key strategies.There is a growing rift between Paul Graham and David Sacks, with tensions and differing perspectives in the venture capital world.Chapters00:00 Introduction and Overview02:21 The Current State of Fundraising08:48 Key Strategies for Fundraising Success15:22 The Drama and Tensions in the Venture Capital World21:10 The Rift Between Paul Graham and David SacksBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.* Thanks for reading! If you find this valuable, please share it with your network. Check out the YouTube channel | Leave us a rating on Apple Podcasts | Follow me on Twitter Get full access to Four Insights at stretchfour.substack.com/subscribe

Sep 11, 202422 min

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 strategies and the importance of building a network. It concludes with a mention of the supporting sponsor, Flippa.venture capital, funding, founders, online businesses, valuation, fundraising, network, whales, Slauson and Co, Better Tomorrow Ventures, FlippatakeawaysVenture capital funding is back, with a surge in funding announcements and a focus on a specific type of founder.Online businesses have value beyond their content, and it's important to understand the analytics and potential for monetization.Fundraising requires building a network and targeting key investors, with warm introductions leading to higher conversion rates.Finding 'whales' or big checkwriters is crucial for fundraising success.Two interesting fund announcements: Wishoff Ventures and Slauson and Co.Flippa is a valuable platform for buying and selling online businesses, offering business valuations and other services.Chapters00:00 The Return of Venture Capital Funding01:00 The Focus on a Specific Type of Founder02:29 Agree: A Unique Business Model for E-Signature Services07:00 Fundraising Strategies: Insights from Nicole Wischoff14:54 Slauson and Co: A Venture Fund with a Friends and Family Program Get full access to Four Insights at stretchfour.substack.com/subscribe

Sep 6, 202417 min

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 | InstagramThe Flippa AdvantageSponsored by FlippaWhile you're sprinting towards your fundraising goals, don't forget about alternative paths to success. Flippa, the #1 platform to buy and sell online businesses, offers opportunities for both buyers and sellers in the tech ecosystem. Whether you're looking to acquire a promising startup or considering an exit strategy, Flippa provides a marketplace to explore your options.While we were enjoying those last summer vibes this weekend, I was thinking about the intense fundraising season that's about to kick off, or well if you are reading this now it already has. As Alexis Ohanian tweeted on Tuesday:"It's officially the time of year when everyone (else) starts pushing - before the holiday slowdown - so take advantage of it."🕒 Timestamps: 0:00 - Introduction 1:30 - The Current Fundraising Landscape 3:45 - Why This Sprint Matters 7:15 - Tips for a Successful Fundraising Sprint 12:30 - The Flippa Advantage (Sponsor Segment) 14:00 - Final Thoughts and Q&AThinking of selling your business? There is only one way to sell an online business and that is with our friends at FlippaFinal ThoughtsRemember, this sprint isn't just about securing funding – it's about positioning your startup for long-term success. Stay focused, be persistent, and don't be afraid to pivot if necessary.Good luck with your fundraising efforts! If you want to dive deeper into fundraising strategies, I do a webinar each Wednesday and Thursday focused on fundraising tactics. Tonight I will be sharing a list of 66 investors actively seeking deals right now.Join me here on Wednesdays.Join me here on Thursdays. This one is private so you will need to email me for the code at [email protected] are your thoughts on this fundraising sprint? Let me know in the comments! Get full access to Four Insights at stretchfour.substack.com/subscribe

Sep 5, 202413 min

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 | YoutubeHey! 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 founders, I think we need to take a step back.Not all founders are Steve Jobs, not all managers are John Sculley, and not all companies are Apple. Some companies may be better off in manager mode, or some kind of tweaner focus where you are not the founder that takes themselves so seriously! If you read it too, I'd love to hear your thoughts.Today's episode and memo dive into Paul Graham's viral Founder Mode essay. Let's unpack its key points, examine its implications for startup culture, and discuss why it might not be the universal solution it's being presented as.Was this forwarded to you?The Essence of Founder ModePaul Graham's essay on Founder Mode has taken Silicon Valley by storm. Here are a few key points:* Contrast between founder-led and manager-led companies* Critique of professional managers and MBAs* Examples like Steve Jobs and Brian Chesky as great leadersGraham argues that founders often feel gaslit when told to run companies like managers. He suggests that "Founder Mode" - a more hands-on, visionary approach - leads to better outcomes. The Risks of Over-Indexing on Founder ModeWhile there's merit to Graham's arguments, I believe we need to be cautious about applying these principles universally:* Not all founders are visionaries: Early-stage startups often need solid operational skills more than grand visions.* Success stories of manager-led companies: Look at Uber under Dara Khosrowshahi or Microsoft under Satya Nadella.* The danger of emulation: Young founders of small startups shouldn't try to lead like Steve Jobs or Brian Chesky prematurely. I think this is where the cultish brand of PG and his essays can do a lot of damage. How can you optimize for founder mode when you are in survival mode as many founders are until they reach a certain revenue or fundraising round that validates and de-risks their business?What Matters for Early-Stage StartupsIf you're running an early-stage startup, here's what I think you should focus on instead of worrying about "Founder Mode" (PG is in no way saying these things do not matter and he has likely written essays about many of these topics before)* Cash Management: Keep enough cash in the bank to reach your next milestone.* Product-Market Fit: Or in YC speak, “Make Something People Want” and understand and solve real problems for your customers. This is a priority over any type of founder-mode strategy for leading a team* Customer Service: Talk to customers, handle support tickets, learn, and iterate. If founders are doing this they will set an example and the best leaders lead by example not with overly aggressive micro-managing. If you are really in the weeds you can answer some support tickets and make a couple hundred cold calls a week.* Team Building: Hire slow, fire fast, and build a strong core team. Founder mode is more for when you have built out a team at scale, the example PG uses references Steve Jobs and his 100-person retreat.* Remember, even the most successful founders didn't start in "Founder Mode" - they grew into it as their companies scaled. The TakeawayWhile Paul Graham's essay offers valuable insights, don't get caught up in trying to emulate the management styles of billion-dollar company CEOs. Focus on what matters most for your stage of growth, and let your leadership style evolve naturally as your company grows.As I said in the episode:"In all in all, think founder mode's a great thing. It went viral, it got a lot of traction, but don't over-index on trying to do founder mode. You'll end up in flounder mode and you won't be successful with your company."What do you think about Founder Mode? Hit reply and let me know your thoughts!Enjoy Four Insights? Tell them to sign up. I'll send them next Monday's memo. Hit the link below to share:Thanks for reading Four Insights! This post is public so feel free to share it.Other News* Are you a founder raising venture capital right now? Check out my all-new Scorecard and get your score for free.* Less than two weeks until my Fundraising Course starts. Enroll now!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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.* Thanks for reading! If you find this valuable, please share it with your network. Check out the YouTube channel | Leave us a rating on Apple Podcasts | Follow me on Twi

Sep 3, 202416 min

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 | YoutubeEOD Show 019 - Detailed Podcast Show NotesHost: Matt ParkerEpisode OverviewIn this episode, Matt Parker dives into the latest trends in pre-seed funding, reveals the surprising list of Twitter X acquisition backers, and discusses recent economic data affecting the startup ecosystem.Key Topics1. The State of Pre-Seed Funding in 2024 (Carta)* SAFEs dominate early-stage funding:* 90% of rounds under $1 million use SAFEs* Preferred for rounds under $3 million* SAFE characteristics:* 85% are post-money SAFEs* 57% have only a valuation cap* 35% have both a valuation cap and a discount* 7% offer only a discount* Valuation trends:* Median valuation cap for $1 million raise: $10 million post-money* $500K raises see valuation caps around $7-8 million* Changes in check sizes:* Small checks under $25K are becoming scarcer* Larger checks taking a bigger slice of investments* Discount rates:* A median discount of 20% when present* Convertible notes:* Interest rates increased to 7.8% in Q2 2024 (up from 6.8% in Q2 2023)2. Twitter X Acquisition Backers Revealed* High-profile investors include:* Andreessen Horowitz* Sequoia Capital* Fidelity* Larry Ellison* Prince Alwaleed Bin Talal of Saudi Arabia* Binance (cryptocurrency exchange)* Sean "Diddy" Combs* Matt's insights:* Demonstrates the complex web of relationships in major tech deals* Importance of building a diverse investor list for fundraising3. Economic News and Job Market Shifts* Labor Department revision:* 818,000 fewer jobs were added in the year ending March than previously reported* Suggests cooling the job market* Impact on startup ecosystem:* Challenging job market for tech workers* Shift from abundant opportunities to more network-based hiring* Insider connections are becoming more crucial for job seekers4. Startup Funding Highlight: Lettuce* San Francisco-based automated tax and accounting system* Raised $15 million in Series A funding from Zeev Ventures* Targets businesses of one, helping with tax and accounting automation* Indicates continued investor interest in fintech and automation startupsCall to Action* Check out Matt's new fundraising course on Maven* Free webinar every Thursday related to fundraising strategies* Subscribe to the End of Day Show on YouTube and podcast platforms* Follow For Insights media platform for more startup and tech newsClosing ThoughtsMatt emphasizes the changing landscape of startup funding and job markets, encouraging founders to stay informed and adapt their strategies accordingly.* 📺 YouTube: FourInsights* 📸 Instagram: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerStay curious,Matt ParkerThe End of Day Show is hosted by Matt Parker and airs four times a week on YouTube and Substack. Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 23, 202417 min

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 | Youtube EpisodeThroughout the show, we hear from our sponsors:* Quickbooks - Save 30% on Quickbooks for 6 months* Apollo.io - AI-powered sales intelligence platform* ZoomInfo - Comprehensive database of business information for prospectingIn this episode, I discusses the story of Ryan Breslow and his company Bolt. I exploring the learning points for founders from the negotiating tactics and PR strategies used by Breslow, as well as the risks and benefits of aggressive deals. I also talk about founder compensation and incentives, highlighting Breslow's requests for a return bonus, back pay, and the option to sell 10% of his shares. We touch on the topic of managing multiple ventures as a founder and the importance of media coverage for startups. Overall, the episode provides valuable insights for founders and entrepreneurs.Takeaways* Negotiating tactics and PR strategies can be effective in raising funds and maintaining a strong presence in the startup ecosystem.* Aggressive deals, such as pay to play provisions, can help founders maintain control and ownership of their companies.* Founder compensation and incentives should be carefully considered, taking into account the company's financial situation and past actions.* Managing multiple ventures as a founder requires balancing commitments and leveraging one's personal brand.* Media coverage is crucial for startups to gain visibility and tell their story.Sound Bites* "Bolt is up to allegedly raise an additional $450 million." * "Pay to play provisions require current investors to participate in the current round." * "Ryan Breslow is asking for a return bonus of $2 million."Chapters00:00 Introduction and Background00:59 The Story of Ryan Breslow and Bolt04:41 Aggressive Deals: Pay to Play Provisions08:25 Founder Compensation and Incentives10:45 Managing Multiple Ventures as a Founder15:31 The Importance of Media Coverage for Startups18:55 Sponsor Message19:27 Conclusion and Key LessonsCheck the show notes for today's key takeaways and timestamps. Please review us on Apple Podcasts or Spotify to support our content. Until next time, keep striving for success!* 📺 YouTube: FourInsights* 📸 Instagram: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerStay curious,Matt Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 22, 202420 min

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 WAR Shocks Silicon Valley | YoutubeIn this episode, I discuss several topics related to startups and fundraising. I highlight the increasing number of venture-backed startups that are shutting down and share some strategies for startup founders. I then mention three opportunities for funding, including Berkeley's Skydeck program, the AI grant, and Y Combinator. I also talk about the importance of maximizing online media presence as a founder and introduce Flippa, a platform for buying and selling digital businesses. Takeaways* The number of venture-backed startups shutting down is increasing, making it a difficult time for many founders.* There are several opportunities for funding, including Berkeley's Skydeck program, the AI grant, and Y Combinator.* Maximizing online media presence is crucial for founders and platforms like Flippa can help in valuing and selling digital businesses.* To make a startup more attractive to investors in a tough market, founders should focus on growth benchmarks, market potential, and building relationships.Titles* Maximizing Online Media Presence as a Founder* Flippa: Valuing and Selling Digital BusinessesSound Bites* "Venture shutdowns are increasing, making it a difficult time for many founders."* "Funding opportunities: Berkeley Skydeck, AI grant, and Y Combinator."ChaptersIntroduction and OverviewIncreasing Number of Venture-Backed Startups Shutting DownOpportunities for Funding: Berkeley Skydeck, AI Grant, and Y CombinatorMaximizing Online Media Presence as a FounderFlippa: Valuing and Selling Digital BusinessesMaking a Startup Attractive to Investors in a Tough MarketConclusionBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love. Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 21, 202415 min

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 | YoutubeSummaryIn this episode, Matt Parker discusses controversial statements made by two billionaires, Eric Schmidt and Michael Rubin. Schmidt, the former CEO of Google, sparked controversy when he claimed that most companies like Google have a culture where people aren't working hard and work-life balance has become a priority. Parker believes that this is how many wealthy people in Silicon Valley think. Rubin, the founder and CEO of Fanatics, made statements about black culture and the dissension within it. Both Schmidt and Rubin quickly retracted their statements after receiving backlash.TakeawaysMany wealthy people in Silicon Valley believe that most companies have a culture where people aren't working hard and work-life balance is prioritized.Controversial statements made by powerful individuals often get retracted quickly due to backlash.There is dissension within black culture, particularly in the entertainment and sports industries.Open and honest discussions about work culture and societal issues are important, even if they are uncomfortable.Building relationships with influential individuals is crucial for people of color to access economic opportunities.Sound Bites"Most companies like Google have a culture where people aren't working that hard and work-life balance has become a very large part of the conversation.""Work from home won't be around in 2025. If you're a company, you're not gonna hire people that can't come into your office."Chapters00:00 Introduction and Overview02:18 Controversial Statements on Work Culture in Silicon Valley06:10 The End of Work from Home07:54 Dissension within Black Culture10:07 Powerful Individuals and Their Views12:00 Building Relationships for Economic Opportunities13:06 ConclusionBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.How would you rate today's show?👍🏾or 👎🏾Was this forwarded to you?Four Insights is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Check out the YouTube channel | Leave us a rating on Apple Podcasts | Follow me on Twitter Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 15, 202414 min

The Coaching Revolution and AI's Data Dilemma

End of the Day Show - Episode 14 Show NotesDate: August 14, 2024 (Wednesday) Host: Matt Parker Location: San FranciscoEpisode SummaryIn 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 Topics1. The Coaching Phenomenon in Silicon Valley. Coaches become influential in how companies are built and founders operate. Coaching as a replacement for traditional therapy2. AI Companies and Wikipedia Data (AI-cyclopedia). AI companies using Wikipedia as a primary data source for training. Debate over the use of public data for commercial AI development. Wikipedia's response: developing an enterprise product for AI companies. Comparison to Reddit's $60 million deal with Google for data access. Discussion on the future of AI training data sources. Mention of the debate between using synthetic data vs. internet data for model trainingResources MentionedNew York Times article on Silicon Valley coachingJerry Colangelo's book "Reboot""The Trillion Dollar Coach" book about Bill CampbellBill Walsh's book "The Score Takes Care of Itself"TLDR.tech newsletterSherwood News article on "AI-cyclopedia"Subscribe to the show on YouTubeLeave a review on Apple Podcasts or SpotifyCheck out the accompanying Substack newsletter for additional information and linksNext EpisodeTune in tomorrow for the next episode of the End of the Day Show!The End of the Day Show is brought to you by Four Insights. For more in-depth analysis and daily tech updates, visit fourinsights.comBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.How would you rate this week's memo?👍🏾or 👎🏾Was this forwarded to you?Four Insights is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Check out the YouTube channel | Leave us a rating on Apple Podcasts | Follow me on Twitter Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 14, 202414 min

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 $48B Fast Fashion King | YoutubeSummaryIn this episode, Matt Parker discusses three main topics. First, he commemorates the passing of Susan Wojcicki, the former CEO of YouTube, and highlights her career guidance and mentorship as her key contributions. Second, he talks about the business of basketball and the evolution of the game, particularly in terms of individualism and branding. Lastly, he discusses the Cloud 100 report, which showcases the top 100 cloud companies in Silicon Valley and highlights the dominance of AI companies and the rapid scaling of these companies.KeywordsSusan Wojcicki, YouTube, Silicon Valley, basketball, NBA, business, Cloud 100, AI, scalingTakeawaysSusan Wojcicki was a highly influential leader in Silicon Valley, known for her leadership at YouTube and her emphasis on career guidance and mentorship.The business of basketball has evolved over the years, becoming more individualistic and focused on branding. The future of the NBA and its importance in 20 years is a topic of debate.The Cloud 100 report highlights the rapid growth and dominance of AI companies in Silicon Valley, with a record valuation of $820 billion for the top 100 cloud companies.Companies in the cloud industry are scaling faster than ever, reaching $100 million in annual recurring revenue in about 7.8 years.The trends in Silicon Valley and the cloud industry show the rapid evolution and change in the tech landscape.TitlesThe Evolution of Basketball: Individualism and BrandingThe Cloud 100: Rapid Growth and Dominance of AI CompaniesSound Bites"Susan Wojcicki valued time over money.""Susan Wojcicki left a great legacy in Silicon Valley.""The business of basketball has become more individualistic and focused on branding."Chapters00:00 Remembering Susan Wojcicki: A Legacy of Leadership07:20 The Changing Landscape of the NBA12:02 The Rapid Growth of Cloud CompaniesBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.These three stories, while distinct, point to a common thread: the increasing importance of individual impact, whether it's in leadership, personal branding, or rapid company scaling. As we navigate this new landscape, it's crucial to consider how these trends will shape the future of business, technology, and entertainment.Four Insights is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.How would you rate this week's show?👍 or 👎Was this forwarded to you?Four Insights is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Check out the YouTube channel | Leave us a rating on Apple Podcasts | Follow me on Twitter Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 13, 202416 min

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 Days | Yesterday’s Show On The Olympics | YoutubeMatt Parker00:00 - 00:30: Introduction and show overview00:30 - 02:28: China's new richest person - Colin Huang and e-commerce trends02:28 - 04:48: YouTube car creators leaving their channels, private equity acquisitions04:48 - 07:12: Discussion on Elon Musk, Tesla, and X.ai07:12 - 09:27: Sam Lessin's essay on "price of intent" in digital advertising09:27 - 11:45: Analysis of attention economy and targeted advertising11:45 - 14:05: Venture capital trends and recession fears, advice for founders14:05 - End: Closing remarks, promotion of ebook and upcoming courseBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.How would you rate this week's memo?👍 or 👎Four Insights is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.Check out the YouTube channel | Leave us a rating on Apple Podcasts | Follow me on Twitter/X Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 9, 202416 min

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 performance by Stephen Curry “30” For more: Top 10 Black-Led VC Funds Guide | My premium subscription to investor lists, course access | YoutubeBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.Let's break it down:* BiggerPockets' Big Break: The real estate education platform just landed a major private equity investment. What does this mean for niche content platforms? We're seeing a shift towards more specialized, community-driven content – and investors are taking notice. Source: Exclusive: BiggerPockets nets majority investment from TCG (Fortune)* Olympics Go Social: The 2024 Olympics are proving that social media is the new primetime. With 80% of viewers aged 14-45 tuning in via social platforms, we're witnessing a revolution in sports coverage. Athletes are becoming content creators, giving us unprecedented behind-the-scenes access. Source: The Paris Olympics Is Minting New Creators (The Information)* Opal's $60M Series B: This hardware startup, backed by top creators and OpenAI, is set to revolutionize content creation. As a creator myself, I'm excited to see how AI will streamline the content production process. Source: OpenAI Makes a $60 Million Hardware Startup Bet (The Information)* Founder Alert: If you're looking to raise venture capital in the next 6-12 months, I've got something special for you. I'm launching an immersive program to help founders master the pitch and navigate the VC landscape. Check out stretch4.co to book a 15-minute slot with me and learn more. Source: The Founder's Fundraising Blueprint: From Cold Email to $1M in 60 DaysRemember, in today's digital age, every company is becoming a tech company, and every individual has the potential to be a creator. Stay curious, keep innovating, and don't forget to tune in to our daily updates!* 📺 YouTube: FourInsights* 📸 Instagram: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerCatch you tomorrow,Matt Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 9, 202416 min

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 subscription to investor lists, course access | Youtube🔥 Top Stories:Turing's Incredible Pivot: From Dev Shop to AI Powerhouse I once thought Turing was “just another dev shop” back when I used their service in 2019. Well, they've pulled off one of the most impressive pivots I've seen. They're now one of the secret weapons behind ChatGPT's success and many other foundational model companies.Here's the scoop:* Originally provided software engineers to startups* Now supplying critical coding data to OpenAI, Anthropic, and other AI giants* This pivot has made them a major player in the AI revolutionKey Takeaway: Sometimes, your most valuable asset isn't what you think it is. Turing found gold in their data, not just their talent pool.Source: Inside the company that gathers ‘human data’ for every major AI company (Semafor)Y Combinator Triples Down: New Fall Batch Announced! YC is shaking things up again. They're launching a fall batch, potentially funding up to 300 startups a year. Here's what you need to know:* Applications due: August 27th* The program starts: on September 29th* Offering: $500,000 investment + $1M in credits* Bonus: Access to dedicated GPU clustersKey Takeaway: The competition for early-stage funding is heating up. YC's move signals a bullish outlook on AI startups.Source: YC Fall 2024 batch applications due by 8/27 (Company website)💡 Founder's Corner: Turning Failure into FuelSpeaking of pivots, I've shared a personal story in today’s show that I am still working through being comfortable talking about. Recently, I had to tell investors that we are not going to make and become what we thought we would at the beginning of the year. Tough pill to swallow, right I am still working through it personally, financially, and professionally. But here's the silver lining:* Each failure is a learning experience* Investors value founders who've been through the wringer* Your network grows with each attempt* You gain invaluable insider knowledgeRemember, many successful founders had multiple failures before their big break. Stay persistent!🚀 Exclusive Offers for EOD Subscribers:* Free Guide: "Cold Email Your Way to Millions" - My step-by-step playbook for landing VC meetings. [Download Here]* Limited Time Offer: Book a 15-minute call with me to discuss your fundraising strategy. Only 5 slots are available this week! [Book Now]* New Course Alert: I'm launching a comprehensive fundraising course at stretch4.co. Early bird discount for newsletter subscribers! [Get on the Waitlist]📺 Don't Miss Our Latest YouTube Video!We break down Turing's pivot and YC's expansion in detail. Plus, there's a secret tip at the end for nailing your YC application! [Watch Now]That's all for today! If you found this valuable, please share it with a friend who might benefit. Let's grow this community together!Do questions or topics you want covered? Hit reply and let me know!Keep hustling,Matt Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 7, 202416 min

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 lawsuit against the company he helped create. For more: Top 10 Black-Led VC Funds Guide | My premium subscription to investor lists, course access | YoutubeBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.The OpenAI Exodus: A Sign of Things to Come?OpenAI, the current darling of the AI world and all of technology right now, is facing turbulent times. The company that brought us ChatGPT, the fastest-growing app in the history of consumer technology is now grappling with a series of high-profile departures. Three executives, including co-founder John Schulman, have left the company, well Greg Brockman say his leave is only temporary. The most alarming part of this for OpenAI and Sam Altman is that, Schulman is heading to Anthropic, OpenAI's main competitor, in a move that has raised eyebrows across the industry.This exodus comes on the heels of last year's dramatic firing and rehiring of Altman, the earlier departure this year of Ilya Sutskever adding to the sense of instability surrounding the company. Meanwhile, Elon Musk, an original co-founder of OpenAI, has renewed his lawsuit against the company, further complicating matters.These developments raise critical questions about OpenAI's future. Has the company peaked? With increasing competition from tech giants like Meta and emerging players like Anthropic, can OpenAI maintain its position at the forefront of AI innovation?Market Turbulence: The Ripple Effect on StartupsThe recent sell-off in public markets, led by Warren Buffett's Berkshire Hathaway offloading $50 billion in Apple stock, has sent shockwaves through the tech industry. This downturn is not just affecting public companies; it's casting a long shadow over the startup ecosystem, particularly the so-called "unicorns" - private companies valued at over $1 billion.The golden age of unicorns, which peaked in 2021 with over 2000 such companies, seems to be waning. In the past three years, only three of these companies have gone public, creating a bottleneck of highly valued private companies with limited options for liquidity.This situation poses a significant challenge for startups at all stages. Without clear paths to liquidity or IPO, many unicorns are facing tough choices: pursue down rounds, seek acquihires, or potentially wind down operations. For earlier-stage startups, this environment makes it increasingly difficult to project optimistic growth trajectories and secure funding.Silver Linings: Innovation in Challenging TimesDespite the gloomy outlook, pockets of innovation and success stories continue to emerge. Take Savvy Wealth, for instance. This fintech startup, led by a three-time founder, recently secured a $26 million Series A2 round. Their success in raising capital in a challenging market, especially in the fintech sector, demonstrates that there's still an appetite for innovative ideas and strong teams.Savvy Wealth's AI-powered platform aims to streamline wealth management, addressing pain points in an industry ripe for disruption. Their success highlights a key lesson for startups in these turbulent times: focus on solving real problems with innovative technology, and funding can still be secured.Upcoming: Exclusive Fundraising ImmersiveWe're excited to announce a new comprehensive fundraising immersive specifically designed for venture-backed founders. Stay tuned for more details on how this program can help you:* Meet with founders who have done it and raised $10M or more for their startups* Get real-time feedback on running your fundraising process* Access real-time lists of investors who are actively investing year-round.Start August 15 (use code: NEWSLETTER30 at checkout for a discount)Sign up for the Raising Venture Capital Immersive waitlistThat's all for today, insiders. Have a great Tuesday and we will see you here tomorrow.* 📺 YouTube: FourInsights* 📸 Instagram: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerStay curious,Matt Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 6, 202415 min

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 to investor lists, course access | YoutubeBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.1. Google Snaps Up Character AI: A Win for Big TechGoogle's making moves in the AI space, and their latest play involves Character AI, the chatbot maker that's been turning heads. Here's the scoop:* Google's paying a licensing fee for Character AI's tech* They're bringing the co-founders back into the Google fold* Many of Character AI's researchers are joining Google tooThe deal values Character AI at 2.5x its Series A valuation from 2023. But here's the million-dollar question: Is this a win for VCs, or just another big tech acqui-hire?The InformationTechcrunch2. Eric Schmidt's $140M Startup DramaEx-Google CEO Eric Schmidt is no stranger to headlines, but his latest venture is raising eyebrows for all the wrong reasons. Here's the tea:* Schmidt invested $140M in a startup incubator led by Michelle Ritter* The venture is now crumbling amidst personal and professional drama* It's a cautionary tale about mixing business with pleasure in Silicon ValleyThis story is a stark reminder that in the startup world, it's not just about your product – it's about who you know and how you navigate complex relationships.The Information3. Amazon's AI Power Play with AdeptNot to be outdone by Google, Amazon's making moves too. They've scooped up Adept AI in a deal that mirrors the Character AI acquisition. It's becoming clear: the AI talent war is heating up, and big tech is pulling out all the stops.The VergeWhat's Next?I'm thrilled to announce our upcoming Venture Capital Bootcamp! If you're a founder looking to navigate the complex world of VC funding, this is for you. We'll cover everything from crafting killer pitches to understanding term sheets.Sign up for the Raising Venture Capital Immersive waitlistAlso, check out these free resources:* VCs for Kamala: A curated list of active VCs supporting diverse founders* Cold Email Ebook: Master the art of outreach for capital raisingThat's all for this week, insiders. Have a great weekend.Cheers, Matt Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 2, 202421 min

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. From AI breakthroughs to fundraising strategies, we've got you covered. For more: Top 10 Black-Led VC Funds Guide | My premium subscription to investor lists, course access | YoutubeBrought 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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.Interview Highlight: Andrew Firestone, CEO of Mermaid ChartAndrew Firestone recently led Mermaid Chart, an AI-powered visual collaboration tool, to a $7.5M seed round. Here are some key takeaways:* The Power of Open Source: Mermaid Chart leveraged its 65,000 GitHub stars and 4 million users to attract investor interest. Lesson: Traction speaks volumes.* AI as a Differentiator: By integrating AI into its core product, Mermaid Chart positioned itself uniquely in the market. Lesson: Identify your tech edge.* Fundraising Process:* 300 meetings over several months* 50 meetings per week during peak periods* Importance of refining your pitch with each meeting* Location Matters: Andrew moved from NYC to San Francisco, citing it as crucial for tech career growth and fundraising opportunities.* Working with Tech Giants: Insights on collaborating with Sid Sijbrandij (GitLab CEO) through OpenCore Ventures.Why This Matters for Our Upcoming CourseAndrew's experience underscores many of the principles we'll be covering in our fundraising course:* The importance of traction and unique value propositions* Strategies for efficient fundraising processes* Leveraging industry connections and location advantagesComing Soon: Comprehensive Fundraising CourseStay tuned for the launch of our fundraising course, where we'll dive deeper into:* Crafting the perfect pitch* Building and leveraging networks* Understanding investor psychology* Negotiating terms and closing dealsAre you ready to supercharge your fundraising efforts? Reply to this email with your biggest fundraising challenge, and we might address it in our upcoming course!Here's to your funding success,Matt Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 1, 202434 min

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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.* A brief overview of today's key stories: Friend.com's launch and Microsoft's earningsFriend.com: A Masterclass in Viral Product Launches* Avi Schiffman's background and previous viral projects* Breakdown of the Friend.com launch strategy* Analysis of the $1.8 million domain investment* The product: An AI-powered wearable "friend"* Social media impact and potential pre-order successMicrosoft's AI Earnings: Big Numbers in a Competitive Landscape* Azure AI services' $5 billion run rate and 900% YoY growth* GitHub and Co-Pilot's impressive performance* AI's impact on developer tools and enterprise adoption* Market reaction and implications for the AI industry* Looking Ahead* Upcoming earnings reports from Meta and Amazon* The evolving landscape of AI product adoption in enterprises* Closing Thoughts* Synthesis of Friend.com's viral strategy and Microsoft's AI growth* Implications for startups and established tech companies* Catch the full episode on our YouTube channel or listen on your favorite podcast platforms like Apple or Spotify!* 📺 YouTube: FourInsights* 📸 Instagram: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerStay curious,Matt Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 31, 202413 min

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 delightful app that works anywhere.* Webflow — Design and develop at the same time.—Run reliable, impactful experiments* Navan — the leading travel and expense platform that employees love.* 🔍 Humane's Hard Times: Remember that AI pin everyone was buzzing about? Well, Humane might be looking for a buyer. We dive into what went wrong and what it means for hardware AI startups. (The Information)* 💼 Rillet's $13.5M Bet on AI Accounting: Can AI automate away all our accounting woes? We break down the opportunities and challenges in this space. (A16z Report)* 📈 The Russell 2000 Rebellion: Small caps are having their moment! We explore why investors are flocking to these smaller companies and what it could mean for startup founders.* 💰 America's Millionaire Club: 1 in 15 Americans are millionaires? We unpack the latest UBS wealth report and what it means for the future of wealth creation.Plus, don't miss our insights on Nvidia's projected $105 billion revenue for 2024 and what it says about the AI hype cycle.Catch the full episode on our YouTube channel or listen on your favorite podcast platforms like Apple or Spotify!* 📺 YouTube: FourInsights* 📸 Instagram: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerStay curious, Matt Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 30, 202418 min

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 CountdownBig week ahead as we enter earnings season for notable tech companies. Here's what to watch:* Tuesday: SoFi, AMD, Microsoft, PayPal, Pinterest* Wednesday: Arm, Meta, Carvana* Thursday: Amazon, Apple, Intel, CoinbaseWhy it matters: Earnings calls provide crucial insights into company performance and industry trends. They're especially important for startups to understand market dynamics and potential opportunities.💡 AI in Focus* Will AI continue to dominate earnings call discussions?* OpenAI just announced its search product* Keep an eye on how companies like Microsoft, Meta, and Amazon discuss their AI initiativesThank you for reading Four Insights. This post is public so feel free to share it.📊 Carvana's Comeback Story* Carvana stock is up 173% this year alone* 219% increase in the last six months* A reminder of the unpredictable nature of the stock market🗓️ 2025 Budget Planning for U.S. Enterprises* Shared services typically make decisions from July to October* Business units decide from September to November* Critical for startups to align their sales strategies with these cycles💼 Spotlight: Powder's $5M Funding Round* Building AI agents for precise document analysis in wealth management* Founded by ex-Addepar talent* Backed by Y Combinator and other notable investors🔮 Looking AheadStay ahead in tech and startups with companies and ventures I support:• ModernTax: Revolutionizing tax services with API access and automated analysis• FirstMeeting: AI-driven pitch optimization for founders and sales teams• Fundraising Course: Accelerated 60-day program to raise capital efficientlyWhether you're raising funds, optimizing operations, or seeking insights, I am involved in these ventures. Stay tuned for more insights and analysis in our next edition!Thank you for reading Four Insights. This post is public so feel free to share it. Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 26, 202413 min

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. ConradThe tech world's latest Twitter drama is heating up faster than an overclocked CPU. David Sacks (PayPal mafia, Yammer founder) and Parker Conrad (Zenefits, Rippling founder) are at it again, with Paul Graham joining the fray. It's like a soap opera, but with more stock options and fewer evil twins (we think).Speaking of drama, want to avoid it in your web design process?Try Webflow! Create stunning, professional websites without writing a single line of code. From sleek landing pages to complex e-commerce sites, Webflow has you covered. Start building your drama-free website today!2. NBA Scores Big with AmazonThe NBA just slam-dunked a massive deal with Amazon, potentially benching TNT. What does this mean for Charles Barkley's retirement plans? Will we still get Kenny and Shaq at least?3. OneStream's IPO: Making It Rain in the Public MarketsOneStream just went public, and Bill Gurley has thoughts. Lots of them. Is this the beginning of the end of the IPO drought? Or just a drop in the bucket? Either way, it's got VCs talking faster than an auctioneer on espresso.Speaking of financials...Is your startup's bookkeeping giving you more headaches than a Series A negotiation? QuickBooks to the rescue! From tracking expenses to managing payroll, QuickBooks makes it easy to keep your finances in check. Try it free for 30 days and see why it's the MVP of successful entrepreneurs everywhere!4. ChainGuard: The New Security Unicorn on the BlockMove over, AI. There's a new buzzword in town: Security. ChainGuard just raised a cool $140M, joining the unicorn club faster than you can say "firewall". With investors like Redpoint, Lightspeed, and Sequoia on board, this security startup is more protected than Fort Knox.Food for Thought* In the Sacks vs. Conrad drama, whose side are you on? Or are you just here for the popcorn?* Will Amazon's NBA deal change how you watch basketball? Or are you sticking to illegal streams (we won't tell)?* If you had $140M to invest in a startup, what would it be? Wrong answers only.That's all for this week's roundup! Remember, in the world of tech and startups, the only constant is change... and maybe VC Twitter drama.Until next time, keep innovating, keep disrupting, and maybe consider updating your LinkedIn profile. You never know when you might become the next tech Twitter sensation!Cheers, Matt ParkerP.S. Don't forget to check out my free ebook on venture fundraising. Who knows? You might be the next unicorn we cover! Get the ebook here.Connect with Matt:* 📺 YouTube: FourInsights* 📸 Instagram: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: Matthew Parker Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 26, 202417 min

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: @FourInsights* 🌳 LinkTree: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerDon't miss out on daily insights, tech news, and startup wisdom. Follow, subscribe, and join the conversation!The Billionaire's Playbook: Brad Jacobs' Latest MoveEver wondered how to make a few billion dollars? Well, Brad Jacobs wrote the book on it, and now he's putting his money where his mouth is.* Jacobs launched two private placements, leveraging up to $5 billion in spending capital.* His company's stock skyrocketed 56% in a single day, reaching $123 per share.* Oh, and did we mention he's bringing Jared Kushner along for the ride?Speaking of websites that skyrocket... 🚀Ready to launch your billion-dollar idea? Start with a website that looks like a million bucks! Webflow makes it easy to create stunning, professional websites without writing a single line of code. From sleek landing pages to complex e-commerce sites, Webflow has you covered. Get started today and who knows? Your startup might be our next billion-dollar story!Kamala Harris: The Fundraising PhenomenonWhile we're on the topic of raising capital, let's talk about Kamala Harris's record-breaking week:* She shattered fundraising records in her first 24 hours as a presidential candidate.* Silicon Valley VCs are reportedly shifting alliances faster than you can say "IPO."* Even Elon Musk is distancing himself from certain political donations.This fundraising frenzy is giving us whiplash! Speaking of which...Is your startup's finances giving you a headache? QuickBooks can help! From tracking expenses to managing payroll, QuickBooks makes it easy to keep your finances in check. Whether you're raising millions like Kamala or bootstrapping your way to success, QuickBooks scales with your business. Try it free for 30 days and see why it's the choice of successful entrepreneurs everywhere!Silicon Valley Drama: The Tea is Hot!Hold onto your hoodies, folks, because the Valley is serving up some piping hot drama:* Parker Conrad (of Zenefits and Rippling fame) took a public swipe at David Sacks on Twitter.* The spicy tweet? "Coups are this man's best for thee." Ouch!* This beef dates back to the Zenefits days when Sacks allegedly orchestrated Conrad's ousting.Remember, in the startup world, today's rival might be tomorrow's co-founder. Always build those bridges... preferably with a killer website from Webflow! 😉OpenAI's Billion-Dollar Burn RateIn "blowing money fast" news:* OpenAI is reportedly burning through $5 billion a year. Yes, a billion with a 'B'.* But don't worry, they're also raking in about $287 million in monthly revenue.* At this rate, they might need to raise more funds by late 2024 or early 2025.Imagine trying to keep track of those expenses without QuickBooks. Nightmare fuel, right?Vanta's Victory LapLast but not least, Vanta just secured a cool $150 million in funding:* Led by Sequoia (yes, the same Sequoia that's been on a funding spree lately).* Vanta is known for its SOC 2 compliance reports, crucial for startups selling to enterprise clients.* This raises questions about Vanta's next big product move. What do you think it could be?Food for ThoughtAs we wrap up another eventful day in tech, here are some questions to ponder:* If you wrote a book titled "How to Make a Few Billion Dollars," what would be your chapter one?* How do you think the influx of political money will impact the tech industry in the coming year?* With companies like OpenAI burning through cash at astronomical rates, is the AI boom sustainable?That's all for today's roundup! Remember, in the world of tech and startups, fortune favors the bold... and those with great accounting software. 😉Until next time, keep innovating, keep disrupting, and maybe consider updating your website!Cheers, MattP.S. Don't forget to check out my free ebook on venture fundraising. Who knows? You might be the next billion-dollar story we cover! Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 25, 20248 min

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: mattaparker* 🐦 X (Twitter): @mattaparker* 🎵 TikTok: @mattaparkerDon't miss out on daily insights, tech news, and startup wisdom. Follow, subscribe, and join the conversation!The Art of Quitting: Lessons from Politics and Startups"Quitting is a very, very interesting subject right now," and boy, isn't that the truth? We kicked off the show discussing Joe Biden's decision to step down and how it relates to the startup world.Key takeaways:* Quitting can often be harder than starting or executing* Timing is everything, in politics and business* For startups, knowing when to quit can be crucial for founders, investors, and employeesAs a founder myself, I shared some personal reflections on the challenges of knowing when to "land the plane" - whether that means an exit, shutdown, or pivoting to a new model.The Wiz Saga: A $23 Billion "Almost" Deal?Remember Wiz? The security company that I first learned about at an event put on by Morgan Stanley in 2022 where all the rave was their innovative onboarding process with the Fortune 500 investment bank? Well, they're back in the news, and it's a doozy. They allegedly turned down a $23 billion offer from Google.* Rumors swirled about a potential $23 billion acquisition by Google* The deal appears to have been strategically "leaked" by Wiz* This move positions Wiz for a potential high-value funding round or IPOWe dissected how companies like Wiz, Figma, and Plaid have used acquisition talks to boost their valuations and leverage in the market. It's a fascinating peek into the chess game of high-stakes tech deals.Harvey AI: The Legal Tech Disruptor Raising Eyebrows (and Funds)Last but not least, we dove into the world of legal tech, focusing on the controversial darling, Harvey AI.* Harvey AI just raised $100 million at a $1.5 billion valuation* They've tripled their ARR since December, implying a $30 million run rate* The legal industry's skepticism vs. VC enthusiasm creates an interesting dynamicWe compared Harvey's journey to other legal tech players like Casetext (acquired for $650 million) and Clio (recently raised $900 million at a $3 billion valuation).Food for ThoughtAs we navigate this ever-changing tech landscape, here are some questions to ponder:* In your experience, what are the signs that it's time to quit or pivot a project?* How do you think strategic "leaks" like Wiz's affect the tech ecosystem?* Are you bullish on AI's potential to disrupt traditional industries like law? Why or why not?That's all for today's roundup! Remember, in the world of tech and startups, the only constant is change. Stay curious, stay adaptable, and never stop learning.Until next time, Matt ParkerP.S. If you found this valuable, don't forget to share it with your network and subscribe to "The End of the Day Show" for daily insights on tech, VC, and more! Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 25, 202412 min

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. Additionally, I'll share insights on how startup founders should approach these topics.Don't forget to subscribe to our podcast on your favorite platform, Apple, Spotify, or YouTube so you never miss an episode. Whether you're an entrepreneur, investor, or tech enthusiast, we're here to deliver the insights you need to stay ahead in this rapidly evolving industry. Join us for our next episode as we continue our exploration of Silicon Valley and the world of tech entrepreneurship.Affiliates & Sponsors* Apollo* Notion* ModernTaxSummaryIn this episode of the Stretch Four Podcast, host Matt Parker discusses several topics in the tech industry. He delves into the complex relationship between publishers and AI companies, highlighting the caution urged by Jessica Lessin, editor and owner of The Information in her piece in the Atlantic, about licensing data to AI companies. Parker also explores rumors about the next move of Ilya Sutskever, former chief scientist at OpenAI, and the power he holds in the AI industry. He discusses the increasing amount of money that Sequoia Capital is investing in Elon Musk's companies and the growing IPO pipeline. Parker concludes by emphasizing the importance of understanding the changing dynamics of the tech industry and staying up to date with venture funding and IPO trends.Takeaways* Publishers should exercise caution when licensing data to AI companies, as it may impact their business model and relationship with customers. * Ilya Sutskever's next move in the AI industry holds significant power and influence. * Sequoia Capital's increasing investment in Elon Musk's companies reflects the shifting priorities in the tech industry. * The IPO pipeline is growing, with more companies expected to go public in the coming months. * Founders need to stay informed about venture funding and IPO trends to navigate the evolving tech landscape.Chapters00:00 The Impact of AI Companies on Publishers10:08 Ilya Sutskever's Next Move: A Silicon Valley Sensation15:32 Elon Musk's Influence on the Market 34:18 The Growing IPO Pipeline: Opportunities and ChallengesSourceshttps://www.theatlantic.com/technology/archive/2024/05/fatal-flaw-publishers-making-openai-deals/678477/https://substack.com/home/post/p-145146031?source=queuehttps://www.theinformation.com/org-charts/figmahttps://www.theinformation.com/articles/figma-shareholders-to-sell-up-to-900-million-of-stock-at-deep-discount-to-adobe-price Get full access to Four Insights at stretchfour.substack.com/subscribe

Jun 4, 202445 min

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 Axios event in San Francisco, highlighting the importance of content creation and media in the venture capital community. The episode concludes with a discussion on the significance of podcasts and content for founders in the tech industry.Apple PodcastsSpotifyPartners* Webflow, the all-in-one platform for creating stunning websites without coding.* QuickBooks Online, the leading accounting software for small businesses.Show Notes04:18 - Shaun McGuire: Discussion of the controversial Sequoia Capital partner known for his pro-Israel stance on social media. Matt analyzes McGuire's influence and the interplay between tech and politics in Silicon Valley, referencing an article from The Information.13:29 - OpenAI vs Google: Framing the AI competition between OpenAI and Google as a rap battle. Referencing an article by Brad Stone about the high stakes and costs involved. Discusses the departure of OpenAI co-founder Ilya Sutskever.22:52 - Is OpenAI a Startup Killer?: Matt ponders whether OpenAI's rapid advancements pose an existential threat to AI startups, disecting a clip from a recent Sam Altman interview. Looks at the challenges facing startups like Hume.ai in light of OpenAI's new voice AI product. Considers if the AI landscape is becoming a battlefield where only tech giants can thrive.34:24 - Axios Event Reflections: Sharing insights from attending an Axios event in San Francisco. Discusses the growing importance of podcasts and content creation for VCs and founders, referencing David Sacks and his influence through the All-In podcast. Emphasizes the need for founders to create meaningful content and cut through the noise.39:31 - Wrap-up: Matt concludes the episode, thanks the sponsors, and provides links to the Stretch Four newsletter, podcast, and his company ModernTax. Invites listeners to reach out with any questions.Sources & LinksSilicon Valley Is Search For Its Piece of the AI Action (Bloomberg)How A Sequoia Partner Became Silicon Valleys Pro Israel Political Warrior (The Information) Get full access to Four Insights at stretchfour.substack.com/subscribe

May 21, 202440 min

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 the show, we hear from our sponsors:* Quickbooks - Save 30% on Quickbooks for 6 months* Apollo.io - AI-powered sales intelligence platform* ZoomInfo - Comprehensive database of business information for prospectingIn the main interview segment, Andrew Firestone shares his journey leading Mermaid Chart, an open-source project turned venture-backed startup in the diagramming and visual collaboration space. Under his leadership, Mermaid Chart has seen impressive growth and recently raised a $7.5 million seed round.To learn more about Andrew Firestone and MermaidChart, check out:* Andrew Firestone's LinkedIn* MermaidChart Website* MermaidChart BlogStretch Four Podcast Show Notes00:06 - Introduction and overview of the show00:51 - Sponsor message from QuickBooks01:22 - Tech News: Growing markets for shares of hot startups like SpaceX and Stripe06:52 - Ramp's Q1 2024 Business Spending Benchmark Report on AI spending11:46 - Sponsor message from Apollo.io12:35 - Introduction to the main interview with Andrew Firestone, CEO of Mermaid Chart14:47 - Andrew's background and journey to becoming CEO of Mermaid Chart19:32 - Differences between starting a company from scratch vs. joining an incubated company22:40 - Working with Sid Sijbradij, the founder and CEO of GitLab (NASDAQ: GTLB), and the venture studio model26:37 - Mermaid Chart's traction, adoption, and the impact of the open-source project29:32 - Mermaid Chart's AI-first approach and competitive advantage31:56 - The process of raising a $7.5 million seed round and the role of the CEO35:51 - Tactics and strategies for running an efficient fundraising process38:49 - The advantages of being based in San Francisco for a tech startup41:46 - Parting notes on Mermaid Chart and how to learn more about the company42:16 - Sponsor message from ZoomInfo42:43 - Conclusion and call-to-action for listenersBefore we end, thanks to our sponsors. QuickBooks, the ultimate financial management tool for businesses, offers 30% off the first six months at QuickBooks.ZoomInfo, with its comprehensive business database, enhances your prospecting. Start your free trial at Zoom Info.Apollo, a sales and marketing intelligence platform, provides lead generation, email automation, and analytics. Get a free subscription at Apollo.Check the show notes for today's key takeaways and timestamps. Please review us on Apple Podcasts or Spotify to support our content. Until next time, keep striving for success!Sources:Tensions Rise in Silicon Valley Over Sales of Start-Up Stocks (New York Times)How Investment Banks Are Helping Canva, Stripe, Figma Stay Private (The Information)AI spending grew 293% last year. Here's how companies are using AI to stay ahead (Ramp) Get full access to Four Insights at stretchfour.substack.com/subscribe

May 14, 202443 min

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 with timestamps:Episode 21 - How to Build a Billion-Dollar Analytics Company (Twice): Lessons from Repeat Founder Colin Zima (Omni)[0:00:00] - Introduction and background on Colin's career path from finance to Google to founding companies[0:09:34] - Colin discusses his transition from finance to tech starting at Google[0:11:54] - He talks about the benefits of smaller startups over large companies like Google[0:16:05] - Colin explains the benefits of building a company with a core team from previous exits[0:23:56] - He discusses product development at Omni and knowing when they had a "good enough" product[0:27:10] - Colin provides tips for founders doing early demos and sales focus on customer pain points[0:31:16] - He shares his perspective on fundraising as a repeat founder with a large exit[0:35:11] - The podcast discusses the state of the BI market and building multi-product companies[0:39:19] - Colin talks about the changing dynamics of b2b SaaS valuations and building for the long-term[0:45:17] - He provides his thoughts on generative AI and product integration[0:50:07] - Colin shares his view on the state of San Francisco and what he's passionate about in the cityListen now on Apple, Spotify, and YouTube.Mentions- Omni.co - Learn more about Colin's new company building the next generation analytics platformLooker - The $2.6 billion acquisition by Google where Colin was employee #40 Where to find Colin Zima* Colin Zima on X* Colin Zima on LinkedinWhere to find our host* Matt Parker on X* Matt’s newsletter on Substack* Matt Parker on Linkedin* Matt Parker on TikTokSponsors:* ModernTax Get full access to Four Insights at stretchfour.substack.com/subscribe

Feb 6, 202454 min

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 the challenges of being a founder.Outline* Introduction to episode and guest, Dan Siroker* Dan's background - started at Google and became director of analytics for Barack Obama's 2008 campaign* How that experience led to the founding of Optimizely, a product that makes A/B testing easy for anyone* Lessons learned from Y Combinator - the importance of building something people want and empathizing with customers* Dan's experience with burnout and falling out of love with his business at Optimizely* The impact of minimizing decisions and wearing the same black V-neck T-shirt every day* Dan's move to Denver and the differences between living there and Silicon Valley* Dan's current venture, Rewind AI, and the importance of storytelling and lowering friction in product demosListen now on Apple, Spotify, and YouTube.Where to find Dan Siroker* Dan Siroker on X* Dan Siroker on LinkedinWhere to find Matt Parker:* Matt Parker on X* Matt’s newsletter on Substack* Matt Parker on LinkedinSponsors:* ModernTax Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 24, 20231h 3m

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 and navigating the visa process.[05:00] Surbhi shares her journey of moving from India to Seattle and participating in the Techstars accelerator program. She talks about the value of being part of a small cohort and the importance of storytelling for a startup.[15:00] The conversation then shifts to the evolution of AI and how Symbl AI is building products that go beyond the traditional bot experience. Surbhi emphasizes the need to connect with the audience and adapt the storytelling as the company grows and the market changes.[19:00] Surbhi discusses the importance of understanding the enterprise market and working on use cases that solve real problems for businesses.[36:47] The episode ends with Surbhi sharing her contact information and inviting listeners to sign up for the private beta of their product, Nebula.There are a few links mentioned in the text:* * Linkedin* Link to the Stretch Four Media substack* http://substack.com/subscribe Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 16, 202337 min

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 fast as a community challenge. Vidal shares his motivation for doing the fast, his preparation process, and the challenges he faced during fasting as he has gone up to 96 hours. We also talk about the potential benefits and risks of fasting, and how to do it safely, we are not doctors and this is not medical advice so listen at your own risk and do your own research. I’ve listed the resources Vidal has used to take a data-driven and scientific approach to his practice.Topics Covered* Vidal's motivation for doing a 48-hour Fast challenge with his community — the idea, the contributors, and how to learn more about fasting and general health and wellness tips for higher performers, parents, and professionals.* The preparation process for the fast — how I did and how he executes it* Challenges faced during the fast — when do the breakdowns tend to happen* Potential benefits and risks of fasting* How to do a fast safely* Goals people typically have versus the scientific benefitsKey Takeaways* Fasting can have potential health benefits such as weight loss, improved blood sugar control, and lower inflammation* It is important to consult with a healthcare professional before starting a fast, particularly if you have any underlying health conditions* Proper preparation is crucial for a successful fast, including staying hydrated and consuming enough electrolytes* The mental challenges of fasting can be just as difficult as the physical ones, and it is important to have a support system in placeShow Notes[0:02:18] Matthew welcomes Vidal Nelson back to the show to discuss the 48 hour fast and asks what motivated Vidal to challenge people on social media try an extended fast.[0:05:52] Vidal explains how he fell into fasting accidentally and has been doing it for 6 years. He talks about preparation, electrolytes, and supplements needed for a fast.[0:11:27] Vidal discusses the challenges of fasting like low energy, dehydration, and hunger hormones. He emphasizes the importance of preparation.[0:15:30] They discuss the potential health benefits of fasting like weight loss, improved blood sugar control, and reduced inflammation.[0:23:21] Vidal talks about breaking the fast and easing back into eating with bone broth, probiotics, and fermented foods. He stresses taking it slow after a fast.[0:28:39] They cover the risks of fasting for certain groups like diabetics and pregnant women. [0:38:36] They discuss reasonable durations for fasting and the benefits of 72-hour fasts.[0:47:15] Matthew shares his experience breaking his fast without proper preparation and what he learned from participating.[0:55:40] Vidal gives an in-depth explanation of insulin resistance and how fasting can improve insulin sensitivity.[1:01:29] They wrap up by discussing the mental clarity benefits of fasting and limiting food decisions.[1:04:10] Vidal recommends supplements from Muscle Feast and Fitness from F45 Kings Grant in Virginia Beach.Resources on Fasting:The Warrior Diet: Switch on Your Biological Powerhouse For High Energy, Explosive Strength, and a Leaner, Harder BodyVidal’s LinksTraining FacilityMuscle FeastHappy Caps Get full access to Four Insights at stretchfour.substack.com/subscribe

Aug 14, 20231h 6m

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 multiple times in the newsletter in issue 13, issue 24, and issue 44 is reportedly being sued by previous investors due to alleged misinformation on their financials during their Series D round of funding. Additionally, I talk about the challenges of fundraising for venture-backed startup founders in the current market.I also share my personal journey with running and how it has become part of his life during the pandemic and I dive a bit deeper into my approach to training and preparing for races, including his focus on improving his average pace, preparing his body, and post-run recovery.Overall, the episode provides insight into the challenges and opportunities facing both founders and runners in today's world. Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 26, 202328 min

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 million in venture capital funds. Dan lives in Oakland and is a Howard alumnus, and his time in Silicon Valley dates back to 2011.The interview covers a range of topics related to entrepreneurship and venture capital, including Miller's experience raising venture capital for Spore Health and the challenges and biases he faced as a Black founder. Miller also discusses the importance of building relationships with investors and communicating with them regularly, even when things are going well. The episode provides valuable insights for early-stage founders looking to raise capital and build successful businesses.Spora Health MembershipsSpora Health For EmployersThis episode is brought to you by ModernTax.ModernTax is a business-to-business insights platform that leverages real-time tax data to help financial institutions make better decisions about individual and small business customers throughout the year. With extensive coverage across seven million US-based businesses and millions of consumers, ModernTax helps you stay compliant and utilize alternative data sets to save time, and money, and increase performance.As a subscriber to the Stretch Four newsletter, we wanted to let you know that ModernTax 2.0 has already launched! Our updated platform includes even more features to help you streamline your workflow and gain insights into your customers.By partnering with ModernTax, you'll have access to our cutting-edge technology and real-time tax data, giving you a competitive edge in the industry. We are also excited to announce that we will be adding a self-serve option shortly so that you can get started with ModernTax even faster.Join now through the link below as we are only onboarding a limited number of new partners. If you are interested in learning more about ModernTax 2.0, complete the form.Show Notes* Introduction (00:08)* The guest is Dan Miller, CEO and Founder of Spora Health* Spora Health is a unique platform for healthcare and lifestyle management for people of color* Dan is a three-time founder and Howard alumni* Dan's expertise is designing and building products for specific demographics* Spora Health has raised venture capital from 13 Ventures out of LA* Spora Health is building a B2B business and working directly with employers to offer Spora Health as a service to their employees* Interview (01:34)* Dan Miller's experience raising venture capital for Spora Health* Dan recognized the lack of attention and focus on addressing inequities and disparities, specifically race-based* Dan knew he needed help to realize his vision* Dan recognized that he needed to raise venture capital to be competitive in the marketplace and realize his vision* Dan's experience of raising venture capital was that it was easier to get meetings, but it was still challenging to find the right partners to bring on board* Dan recognizes the importance of being discerning with his time and sussing out whether a conversation with potential investors will go anywhere* Dan recognizes that the fundraising process is riddled with bias and that it's critical for early-stage founders to be thoughtful about the folks they accept money from* Dan recommends slowing down and thinking about the skill set of the folks being brought on board and how they view the business generally, how excited they are about it, and how they can help when things inevitably slow down* Dan emphasizes the importance of building integrity toward communication with investors and building value as it relates to integrity and communication with investors* Dan recommends over-communicating with investors in the earlier stages of the business and quarterly updates as the business progresses* Dan urges founding members to try to build a personal relationship with their investors, understand their values, what motivates them, and what excites them about the business so that conversations about support can be more educated Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 19, 202341 min

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 how I am using July to set a high focus to keep my team motivated, as well as the realities of remote work as a CEO.We'll also dive into the life of being a founder and how it relates to fatherhood inspired by Draymond Green of all people, and share some insights from other podcasts and LinkedIn posts that got me thinking about fatherhood versus work as the wifey and I move into the third trimester.Don't miss out on this all-encompassing life of being a founder and what that entails.* The episode features a discussion on the importance of maintaining urgency and intensity to keep people focused on their goals.* Matt talks about his podcast and what it is and how it takes an inside baseball approach to the venture capital industry from a founder's perspective.* The episode includes a segment on fatherhood and parenting, including insights from NBA player Draymond Green and a LinkedIn post by Jordan Nichols.* The importance of having a support system in place to execute the founder's vision is emphasized.* The challenges of remote work and the need for hard conversations in an engineering-focused company are discussed.Links and References* my LinkTree Account* My Threads Account* Stretch Four Podcast* Start With Why* Jordan Nichol’s LinkedIn post* No Priors Ep. 23 | With Snowflake's CEO Frank SlootmanSponsors* ModernTax Get full access to Four Insights at stretchfour.substack.com/subscribe

Jul 11, 202324 min

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 I met our guest Yoni Rubin in the wild), and also where I learned about the critical importance of relationships in specific industries and geographies. Tune in for this and more on the Stretch Four Podcast, available on Apple Podcasts and Spotify. Don't forget to leave us a review if you enjoy the show!* 2:14 — I shared my insights on being ruthless with your time, particularly as it relates to attending events, conferences, and other work-related things. I provided a four-step framework for approaching events, including assessing every possible interaction ahead of time, having a team that can help with deep outreach, prioritizing 100 meetings, and doing a deep debrief after the event.* 11:13 — I also recommended the book 4000 Weeks: Time Management for Mortals for founders and business people looking to be more efficient with their time.* 16:19 — Finally, I shared my takeaway from attending the OnRamp insurance conference in the Midwest, highlighting the importance of relationships and the differences in communication and interaction in the midwest compared to Silicon Valley.* 23:39 — Finally, I welcomed back Yoni Rubin, founder of MRGN, as a guest to discuss his experience and insights on entrepreneurship and his company.Links:* Yoni Rubin, founder of MRGN* OnRamp insurance conference* 4000 Weeks: Time Management for Mortals Follows:* http://twitter.com/mattaparker* https://www.instagram.com/mattaparker/* https://www.linkedin.com/in/matthewaparker31/* https://substack.com/@stretchfournba* https://www.tiktok.com/@mattaparkerGuests* https://www.linkedin.com/in/yonirubin/* https://twitter.com/yrubinucfFollow the pod:* Apple Podcasts * Spotify Podcasts * Youtube Get full access to Four Insights at stretchfour.substack.com/subscribe

Jun 27, 202348 min

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. I share my thoughts on why it's a smart move to raise a large amount of capital and take dilution upfront, especially in the AI and machine learning space. The pedigree of Mistral AI's founders, who come from Google DeepMind and Facebook's meta teams, is a major factor in attracting investors.I also talk about the importance of having solid reference customers and the impact it can have on a startup's success. I share my struggles with reference customers and how not having them can be detrimental to a business. It's crucial to have social proof to close new deals, and prospects tend to talk to other prospects, so having reference customers is a must.Additionally, I discuss an upcoming panel I'm hosting on embedded insurance at the Onramp conference in Minnesota. I'm excited to be leading this panel and sharing my insights on this topic with the audience.Thanks for tuning in to another episode of the Stretch For Podcast! Don't forget to subscribe and leave a comment on Apple or Spotify, and check out the show notes for more details on the topics covered in this episode.Show notes* [04:53] Mistral AI raised $130 million in their seed round and we discuss why taking that dilution is a good move for them. I also share a story from my business where being active led to great results.* [08:50] I talk about hosting a panel on embedded insurance at the OnRamp Conference in Minnesota and share some of the things I'll be discussing.* [10:11] I share my progress with intermittent fasting using the Zero app and how I'm setting it up.* [10:51] I discuss bringing back an executive assistant to take away some of my workloads.* [11:17] I share a personal milestone of celebrating my two-year anniversary with my wife at the Indian Springs Resort in Calistoga.* [12:03] I interview James Hawkins, the founder, and CEO of PostHog, an open-source product analytics company that came out of YC a few batches ago. James talks about growth hacking on Hacker News, dealing with his daughter having cancer, raising consecutive rounds of funding, and more.Links to everything mentioned in the episode can be found in the show notes. Don't forget to like, subscribe, and comment on Apple or Spotify, and check out the Stretch For YouTube channel for even more content. Links:* Mistral AI * Lattice CEO* Never Lose a Customer Again book* OnRamp Conference* PostHog* Stretch Four YouTube (Subscribe Now)* Apple (Write a review)* Spotify Get full access to Four Insights at stretchfour.substack.com/subscribe

Jun 20, 20231h 8m

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 generative AI companies and a snowflake event for early-stage startups. I also attended events hosted by Culture House and Mantis VC, among others, and shared insights into the industries and people I encountered, including b2b enterprise, content creation, and data infrastructure.As always, please like, subscribe, and comment on all of our channels across Apple Music, Spotify, and Substack. Thank you for tuning in to the Stretch Four Podcast!Matt recaps my experiences at both the San Francisco and Los Angeles Tech Weeks.[00:09]Matt attended several events during the SF Tech Week, including the Stonks x a16z Demo Day for generative AI companies, and a BTV event featuring a panel with two founders from the BTV portfolio. Matt also attended a Snowflake event geared toward early-stage startup[03:48]In LA, Matt attended the Culture House event, which is primarily focused on a diverse group of tech, content, and media professionals that gather at events like SXSW, The Essence Festival, and now Tech Week. He also highlights an event he attended hosted by Mantis VC, the venture capital arm of The Chainsmokers family office.[06:16]Matt notes that the LA tech scene is very focused on content creation, media, and gaming, whereas the San Francisco tech scene is more focused on enterprise and AI.[09:38]Matt also discusses the importance of self-care and mental health in the tech industry, noting that burnout is real and that it's important for companies to prioritize their employees' well-being.[12:05]As always, listeners are encouraged to like, subscribe, and provide feedback on all of the podcast's channels across Apple Music, Spotify, and Substack.Links:* Stretch Four YouTube (Subscribe Now)* Apple (Write a review)* Spotify* CultureHouse* Stonks* Tech Week Get full access to Four Insights at stretchfour.substack.com/subscribe

Jun 15, 202320 min

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 Clockwise, now available on Youtube. And make sure to head over to our new YouTube channel to check out the video version of this episode and clips from previous episodes. We appreciate your support and can't wait to bring you more exciting content in the future!I enjoyed discussing MoonPay's $150M secondary and Plaid's screen-scraping empire this week. If you enjoyed the episode, don't forget to like, subscribe, comment, and leave reviews on Apple or Spotify.Show Notes* I attended three events in San Francisco's tech week — and plan to attend two in LA later this week. The SF recap got cut but I will be sure to recap both SF and LA with a special guest.* T. Scott Patterson, CEO of Tumble, talks about how he built his company through the pandemic.* The Information reported that MoonPay's co-founder and his team cashed out substantially on a big round in 2021, and the deal is already been devalued by large investors.* Plaid, a screen-scraping company, is valued at $13 billion, and it has 8,000 FinTech apps using the platform today. Plaid has laid the foundation for many companies to scrape financial data.* Plaid's screen scraping has made open banking a real thing, but it has also paid the price for screen scraping.* Plaid has partnerships with 45 financial institutions and is used by one in three US bank account holders.* Mark Zuckerberg's Memorial Day fitness challenge is also discussed.Links:* Stretch Four YouTube (Subscribe Now)* Apple (Write a review)* Spotify* The Information Article on MoonPay* Plaid* Tumble* Chris Bosh's former waterfront Miami Beach mansion* ModernTax* The Bloomberg article on Plaid Get full access to Four Insights at stretchfour.substack.com/subscribe

Jun 6, 20231h 1m

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 market. I also talk about the bankruptcy of Plastiq, a B2B payments business, and the challenges of serving small business owners.In addition, we have a guest interview with Matt Martin, co-founder and CEO of Clockwise. Clockwise is a productivity app that helps you make time and get your calendar organized. We discuss their innovative new scheduling software and their recent launch of a Clockwise AI feature. We also talk about Matt's experience as a parent to daughters and his journey in raising over $50 million in venture funding for his business from top VCs.Finally, I share my own fitness journey and discuss the benefits of running as a parent. Don't forget to follow and review our podcast and provide feedback to help us improve. Thank you for listening!Founder Learnings (02:38 - 13:15)* Shares experience at Finovate conference and importance of getting the product to market* Discusses struggles of working with customers in stealth mode* Talks about the bankruptcy of B2B payments company, Plastiq, and the struggles of serving the small business market* Emphasizes the importance of revenue in payments businesses and moving upmarket* Offers personal insight on running and fitness as a fatherKids Corner (13:16 - 16:22)* Discusses an interesting substack related to being a parent and staying in shape* Talks about his own personal training for an upcoming half marathonInterview with Matt Martin, co-founder and CEO of Clockwise (16:23 - 31:10)* (16:23) Introduction of Matt Martin, co-founder and CEO of Clockwise* (16:58) Discussion about Clockwise and its productivity app* (20:02) Matt's life in San Francisco as a parent and CEO* (22:42) Discussion on the development of the Clockwise AI feature* (25:43) The benefits of using Clockwise for scheduling* (27:53) The future of Clockwise and its plans for expansion* (29:44) Matt's advice for early-stage startup foundersOutro (31:11 - 32:00)* Thanks, listeners for tuning in and teasing upcoming episodes, church announcements, and travel schedule* Encourages listeners to leave a review and subscribe to the podcastPodcast Links* Apple* Spotify* YouTubeShow Links* Finovate* Plastiq* New Fatherhood Substack* David Goggins* Clockwise Get full access to Four Insights at stretchfour.substack.com/subscribe

May 30, 20231h 5m

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 the program.I then interview Tanvi who shares her journey from big tech to entrepreneurship, including her experience building pricing algorithms at Uber. She also explains how Luca is helping retailers optimize their pricing strategies using AI and shares her insights on the future of AI. Tune in to learn more about the power of AI to solve real problems and how to succeed as an early-stage founder.LinksLuca Podcast Links* Apple* SpotifyCheck out the episode on Apple and Spotify.Summary* 0:10 Intro to the show. * Welcome back to the Stretch Four Podcast.* The Newchip accelerator is bankrupt.* Presenting at the Finovate Spring Conference in San Francisco.* 3:17 Yoni Rubin’s experience with the new chip accelerator. * Jani's experience with Newchip accelerator.* How Yoni got involved with the program.* Mentorship experience as a mentor, bleak and best case scenario.* Offering equity to mentors.* 7:47 Where things went wrong with the recruitment process. * Pay-to-play model vs pay to play model.* Shrink wrap agreements.* Getting back to them about the equity and fees.* Researching the price point.* 12:11 How did you get into the space? * Accelerators can be scrupulous. They want to cover their ass.* The company went bankrupt.* Accelerator took a legal document and mixed it into their handbook.* Pricing and fees.* A compelling story for founders.* 18:26 Introducing Tanvi Certi and How we met? * The first time they met and what it was like.* The rollercoaster journey.* Getting out of his comfort zone in 2022.* The early stages of the journey.* Luca is an AI-based pricing copilot for large retailers.* Pricing is a multi-dimensional chess game.* 24:47 How did you get into this space?* Early days of uber pool and building the product.* How he landed at uber.* Why uber was losing copious amounts of money.* How luca came about.* 30:46 The retail side of the house. * How retailers think about these types of offerings.* My John Elliot example of flash sales.* Behind the scenes of pricing and marketing.* 34:18 The revolution of AI. * AI is happening in real-time.* How the AI revolution has happened.* The power of AI to solve real problems.* Why Luca is an AI company.* 37:51 AI for the service of human time and decisions. * AI is a decision-making brain that simplifies the human experience.* Y combinator experience.* Skepticism before applying to YC.* Recommendation for the YC application process.* Getting the first customer from zero to one.* Building a playbook for acquiring customers.* 44:49 Selling to the enterprise early. * Selling to the enterprise early.* Friction from the current way of growing the business.* The money-back guarantee.* The old-school face-to-face way of working during the pandemic* 50:13 In-person work vs. remote work. * A strong believer in in-person work.* How to take care of yourself as a founder.* The importance of a strong support system.* Fundraising for the first time.* Investing in the future of the company.* Being excited in every call.Looking forward to being back with more interviews next week. Get full access to Four Insights at stretchfour.substack.com/subscribe

May 24, 20231h 1m

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. We discussed his takes on nutrition including his five-year journey with intermittent fasting, his fitness regimen, and his wellness hacks on being and even being in better shape than he ever was as a division college football player at James Madison University. Vidal is a high performer and I felt he was a great guest on the show who I plan to invite back as a regular.Show Outline* (4:22) I recap an article The End of Faking It in Silicon Valley (New York Times) and how it impacts how founders have to approach the new market for venture capital and how founder ethics sometimes share friction when it relates to venture capital expectations.* (11:39) I tell more about the viral story of Datadog’s $65M/year customer mystery solved (Pragmatic Engineer)* (18:05) I interviewed lifestyle, health, and wellness expert, and most-recently influencer Vidal Nelson. We talked for a bit about his diet, nutrition regimen, and more.* (25:09) Becoming an influencer in the past three months securing his first gym and ambassador relationship with a local gym as well as how he secured an ambassador relationship with Musclefeast.* (31:16) On being a black man and demystifying health and wellness in terms of how our ancestors ate and lived at scale and the main things he trying to instill in his daughters.LinksMusclefeastVidal Nelson’s InstagramF45 Virginia BeachPodcast Links* Apple * SpotifySponsorsModernTax is a business intelligence platform built on top of tax information to help financial institutions make better decisions. Get full access to Four Insights at stretchfour.substack.com/subscribe

May 16, 202341 min

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 well as his wildly viral concept of "1000 True Fans".He also drops some parenting advice related to his latest book Excellent Advice For Living and shares some insights on how he built his personal brand.Kevin's thought-provoking conversation will leave you inspired to strive towards becoming the only one in something and to invent and define your own version of success. So sit back, relax, and enjoy the show!Here are some of the main topics discussed with their timestamps:* 04:37 - Kevin Kelly's advice on having more children and building family rituals* 08:23 - The importance of intergenerational knowledge sharing and preserving cultural heritage* 11:41 - The benefits of striving to be the only one in something, rather than just the best* 17:50 - How Kevin Kelly designed his personal brand and built collaborative influencers around his work* 20:39 - Kevin Kelly's brand of radical optimism and why he remains optimistic about the futurePodcast Links* Apple (leave reviews and ratings)* SpotifySponsors Deel, a hiring platform that helps companies onboard global talent quickly and compliantly ModernTax is a business intelligence platform built on top of tax information to help financial institutions make better decisions. Get full access to Four Insights at stretchfour.substack.com/subscribe

May 9, 202344 min

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 solutions, and more. And that’s just the beginning. It’s time you got your hands on our free international compliance handbook.Hey Everyone,Welcome back to the Stretch Four Podcast! We're excited to bring you another power-packed episode, featuring an interview with the amazing Ben Lilienthal, CEO and Founder of ScreenMeet, as well as some other hot topics that have been on our minds lately.We're thrilled to announce that we'll be returning to our weekly podcast schedule as we move into the spring and summer months, so be sure to tune in every week for more exciting conversations with some of the most innovative and successful entrepreneurs in the world.We love hearing from our listeners, so please don't hesitate to like, share, and send any feedback, questions, or more directly to me at [email protected]. And if you're enjoying the podcast, we'd be so grateful if you could leave us a review, share it with your friends and colleagues, and help us spread the word.Thank you for listening, and stay tuned for more great episodes of the Stretch Four Podcast!Show notes(4:35) I discuss a chart produced by India in Pixels by Ashris that breaks down the median household income by ethnicity. I explain why I believe this is a call for startups from African-American and Hispanic founders, and why I think people should be focusing on the real emergency in Silicon Valley.(10:52) I talk about how I went to see the new Air Movie with my wife and how it provided me with the inspiration to start running for my upcoming half marathon in July.(15:18) I introduce a new segment called Kid's Corner, where I discuss my thoughts on the "Time Billionaire" concept by Graham Duncan. This idea was brought to my attention by Sahil Bloom's tweet and blog post, and it really got me thinking.(22:15) I interviewed Ben Lilienthal, the CEO and Founder of ScreenMeet. He spoke about his experience of getting fired, running out of money, and building four successful B2B enterprise companies. He also shared his insights on parenting, which I found to be quite interesting.(36:40) How ScreenMeet differentiates itself and he got lucky for its first large enterprise deal and now with 5% of the Fortune 500 customers.(56:19) Thanks to our sponsors and church announcements:* Deel* ModernTax* Check out the Stretch Four Insights Newsletter* 2023 Finnovate Spring ConferenceLinks* Median Household Income in the United States by Ethnic Group* Air* Shoe Dog: A Memoir By the Creator of Nike* The Tim Ferriss Show Transcripts: Graham Duncan (#362) (Tim Ferris Podcast)* The Time Billionaire: A Concept That Changed My Life (Sahil Bloom Newsletter)* Four Thousand Weeks Management For Mortals* Guest Interview Contact: Screenmeet.com to learn more reach out to [email protected] Links* Deel Handbook* ModernTax NewsletterPodcast Links* Apple (leave reviews and ratings)* Spotify Get full access to Four Insights at stretchfour.substack.com/subscribe

Apr 27, 202358 min