| $7T | “seven trillion dollars” | Lessin: Asking for $7 trillion is the act of a religious leader | Sam Lessin | Feb 16, 2024 | — |
| $5T | “five trillion dollars” | Gil: Automating 10% of Services Payroll Recreates the Entire SaaS Market | Elad Gil | Jun 21, 2024 | — |
| $4T | “four trillion dollars” | AI market faces correction because infrastructure capex far outpaces enterprise use | Dave Morin | Aug 21, 2026 | — |
| $3T | “three trillion dollars” | Dave Morin: Big Five Tech Platforms Accrued Over $3T Recently | Dave Morin | Dec 22, 2023 | Supported |
| $1.5T | “a half trillion dollars” | SpaceX reached a $2.5 trillion valuation as of June 2026 | Jessica Lessin | Jun 19, 2026 | Supported |
| $1.5T | “half a trillion dollars” | Sam Lessin: ChatGPT Is Useful But Not Worth Half a Trillion Dollars | Sam Lessin | Sep 19, 2025 | — |
| $1.5T | “half a trillion dollars” | Lessin: Blackstone has only had one fund over 3x in 40 years | Sam Lessin | May 24, 2024 | Supported |
| $1T | “a trillion dollars” | Lessin: OpenAI and Anthropic will soon seek trillion-dollar valuations | Jessica Lessin | May 22, 2026 | — |
| $1T | “one trillion dollars” | Dave Morin: Nvidia faces one trillion dollars in chip demand over next year | Dave Morin | Mar 20, 2026 | — |
| $1T | “a trillion dollars” | Landesberg: 2025 will be most expensive wildfire year, topping $1 trillion | Stuart Landesberg | Oct 31, 2025 | Partly held up |
| $1T | “a trillion dollars” | Lessin: OpenAI pushes 'Apple is doomed' narrative to raise $1 trillion | Jessica Lessin | Sep 12, 2025 | — |
| $1T | “a trillion dollars” | Dave Morin: The Apple App Store did $1 trillion in business in 2022 | Dave Morin | Sep 13, 2024 | Supported |
| $1T | “a trillion dollars” | Lessin: The AI Wave Will Sink $1 Trillion to Create $300 Billion | Sam Lessin | Jun 21, 2024 | — |
| $1T | “a trillion dollars” | Yakovenko: Stablecoins will reach $1T in near-future crypto growth mode | Anatoly Yakovenko | Jul 11, 2025 | Open |
| $1T | “one trillion dollars” | Morin: US markets erased $1 trillion taking DeepSeek's claims at face value | Dave Morin | Jan 31, 2025 | — |
| $300B | “three hundred billion dollars” | Lessin: The AI Wave Will Sink $1 Trillion to Create $300 Billion | Sam Lessin | Jun 21, 2024 | — |
| $300B | “three hundred billion dollars” | Ben Lerer: Seed venture shares nothing with mega-round AI investing | Ben Lerer | Apr 18, 2025 | — |
| $270B | “two hundred seventy billion dollars” | Sam Lessin: Google Added $270B in Market Cap Post-Antitrust Decision | Sam Lessin | Sep 6, 2025 | Supported |
| $100B | “a hundred billion dollars” | Lessin: Meta's AI Infrastructure Is an Aircraft Carrier, Not a Miata | Sam Lessin | Jul 31, 2026 | — |
| $100B | “a hundred billion dollars” | Lessin: Markets ignore one-time outages, caring only about systemic risks | Sam Lessin | Oct 24, 2025 | — |
| $100B | “a hundred billion dollars” | Sam Lessin: YouTube's Hype tipping is driven by junior PMs seeking promotion | Sam Lessin | Sep 20, 2024 | — |
| $100B | “a hundred billion dollars” | Sam Lessin: Public markets reward tech giants for burning billions on AI | Sam Lessin | Jul 5, 2024 | — |
| $100B | “a hundred billion dollars” | Lessin: Native mobile startups capped out at around $100B, led by Uber | Sam Lessin | Jun 21, 2024 | — |
| $100B | “a hundred billion dollars” | Jessica Lessin: OpenAI is probably not worth $100 billion | Jessica Lessin | Apr 5, 2024 | — |
| $100B | “a hundred billion dollars” | Ben Lerer: Startups burning tens of billions rarely deliver strong VC returns | Ben Lerer | Apr 18, 2025 | — |
| $100B | “a hundred billion dollars” | Sam Lessin: Big Tech burning $100B on AI is worth it for downside protection | Sam Lessin | Mar 22, 2024 | — |
| $60B | “sixty billion dollars” | There is no scenario where Cursor is worth $60 billion | Sam Lessin | Apr 24, 2026 | — |
| $60B | “sixty billion dollars” | Levie: FTC scrutiny is hyper-targeted at just four or five Big Tech firms | Aaron Levie | Dec 6, 2024 | — |
| $60B | “sixty billion dollars” | Brit Morin: Mobile created companies like Uber, but no trillion-dollar companies | Brit Morin | Oct 11, 2024 | Supported |
| $50B | “fifty billion dollars” | Brit Morin: Google stock dropped 25%, shedding $150B in one day | Brit Morin | May 9, 2025 | Supported |
| $31B | “thirty-one billion dollars” | Lessin: ByteDance Q3 2023 Revenue Rose 43% to $31 Billion | Jessica Lessin | Mar 8, 2024 | — |
| $30B | “thirty billion dollars” | Lessin: Greg Brockman's OpenAI stake is worth about $30 billion | Jessica Lessin | May 8, 2026 | Supported |
| $30B | “thirty billion dollars” | Levie: FTC scrutiny is hyper-targeted at just four or five Big Tech firms | Aaron Levie | Dec 6, 2024 | — |
| $23B | “twenty-three billion dollars” | Jessica Lessin: Google is highly unlikely to acquire Wiz for $23B | Jessica Lessin | Jul 19, 2024 | Partly held up |
| $11B | “Eleven billion dollars” | Lessin: An $11 billion OpenAI loss is irrelevant to Microsoft | Sam Lessin | Dec 27, 2024 | — |
| $10B | “ten billion dollars” | Lessin: The Information broke that Amazon may invest $10B in OpenAI | Jessica Lessin | Dec 19, 2025 | Supported |
| $10B | “ten billion dollars” | Lessin: Elon Musk's true genius is brokering massive capital into tech | Sam Lessin | Sep 26, 2025 | — |
| $10B | “ten billion dollars” | Morin: Eras Tour generated at least $10B for host city economies | Brit Morin | Dec 13, 2024 | Partly supported |
| $10B | “ten billion dollars” | Brit Morin: Nike gained 9% post-SKIMS announcement; SKIMS valued at $4B | Brit Morin | Feb 21, 2025 | Partly supported |
| $10B | “ten billion dollars” | Lessin: Microsoft Is Developing Cheaper In-House AI to Avoid OpenAI Costs | Jessica Lessin | Sep 29, 2023 | Supported |
| $8B | “eight billion dollars” | Lessin: The New York Times' power far exceeds its financial weight | Sam Lessin | Sep 26, 2025 | — |
| $5B | “five billion dollars” | Lessin: Some leading AI companies are losing $5 billion annually | Jessica Lessin | Dec 6, 2024 | Supported |
| $4B | “four billion dollars” | Brit Morin: Nike gained 9% post-SKIMS announcement; SKIMS valued at $4B | Brit Morin | Feb 21, 2025 | Partly supported |
| $3B | “three billion dollars” | Jessica Lessin: OpenAI raised $3B from retail investors in latest round | Jessica Lessin | Apr 3, 2026 | Supported |
| $3B | “three billion dollars” | Marc Benioff acquired Intercom (Fin AI) for approximately $3 billion | Sam Lessin | Jun 19, 2026 | Partly supported |
| $2B | “two billion dollars” | Brit Morin claims Pepsi recently acquired soda startup Poppi for $2 billion | Brit Morin | Mar 21, 2025 | Supported |
| $2B | “two billion dollars” | Brit Morin: Selena Gomez's Rare Beauty Is Valued at $2 Billion | Brit Morin | Mar 29, 2024 | Supported |
| $1.5B | “half a billion dollars” | Aoun: Forward burned $500M and investors immediately offered next checks | Adrian Aoun | Nov 22, 2024 | — |
| $1.5B | “a half billion dollars” | Morin: Top 9 VC firms spent $27.5B on AI rounds in past year | Brit Morin | Jun 20, 2025 | — |
| $1.5B | “half a billion dollars” | Lessin: Meme coin Jelly Jelly hit $200M market cap on $500M volume | Sam Lessin | Feb 7, 2025 | Not publicly verifiable |
| $1.5B | “half a billion dollars” | Dave Morin: Reddit and Truth Social have comparable market caps despite revenue disparity | Dave Morin | Mar 29, 2024 | Partly supported |
| $1.2B | “1.2 billion dollars” | Morin: Jeff Bezos's wedding injected $1.2 billion into Venice's economy | Brit Morin | Jul 4, 2025 | Contradicted |
| $1B | “a billion dollars” | Sam Lessin: Jony Ive's brand makes his OpenAI acquisition effectively free | Sam Lessin | Jul 17, 2026 | — |
| $1B | “a billion dollars” | Jessica Lessin: OpenAI Generates $1 Billion Annually Selling AI Model Access | Jessica Lessin | Jul 26, 2024 | Supported |
| $1B | “a billion dollars” | Sam Lessin: Owning a $10M Business Is Easier Than a $1B Exit | Sam Lessin | Jun 7, 2024 | — |
| $1B | “a billion dollars” | Jessica Lessin: Humane will not sell for $1 billion | Jessica Lessin | May 24, 2024 | Held up |
| $1B | “a billion dollars” | Sam Lessin says individual AI researchers are receiving billion-dollar compensation packages | Sam Lessin | Aug 1, 2025 | — |
| $1B | “a billion dollars” | Lessin: Coatue launches $1B permanent capital fund with a $50K minimum | Jessica Lessin | May 9, 2025 | Supported |
| $1B | “a billion dollars” | Morin: Hailey Bieber's Rhode sold to e.l.f. Cosmetics for $1B | Brit Morin | May 30, 2025 | Supported |
| $1B | “a billion dollars” | Sam Lessin: Children's entertainer Blippi is worth around a billion dollars | Sam Lessin | Mar 22, 2024 | — |
| $1B | “a billion dollars” | Sam Lessin: Loom sold for about $1 billion | Sam Lessin | Dec 8, 2023 | Partly supported |
| $1B | “a billion dollars” | Lessin: Founders Have the Right to Vet Who VCs Make Money For | Sam Lessin | Oct 13, 2023 | — |
| $1B | “a billion dollars” | Jessica Lessin: Databricks is acquiring MosaicML for over $1 billion | Jessica Lessin | Jun 30, 2023 | Supported |
| $500M | “five hundred million dollars” | Sam Lessin: A $500 million venture fund is the exact wrong size | Sam Lessin | Oct 4, 2024 | — |
| $200M | “two hundred million dollars” | Lessin: Meme coin Jelly Jelly hit $200M market cap on $500M volume | Sam Lessin | Feb 7, 2025 | Not publicly verifiable |
| $100M | “a hundred million dollars” | Benchmark's Vishria: Foundation model companies making $100M revenue will fail | Jessica Lessin | May 2, 2025 | — |
| $100M | “a hundred million dollars” | Sam Lessin: LIV Golf's massive spending brilliantly extorted the PGA Tour | Sam Lessin | Aug 11, 2023 | — |
| $77M | “seventy seven million dollars” | Jessica Lessin: The Washington Post Lost 50% of Its Audience | Jessica Lessin | Jun 7, 2024 | Partly supported |
| $70M | “seventy million dollars” | Sam Lessin: BuzzFeed doubled its market cap to $70 million | Sam Lessin | May 17, 2024 | — |
| $60M | “sixty million dollars” | Brit Morin: OpenAI invested $60M into Opal Camera | Brit Morin | Aug 9, 2024 | Partly supported |
| $60M | “sixty million dollars” | Lessin: Slow Ventures closed a $60M creator fund backed by MIT. | Sam Lessin | Feb 14, 2025 | — |
| $50M | “fifty million dollars” | Lessin: Paramount bought The Free Press for $150M, naming Weiss CBS editor-in-chief | Jessica Lessin | Oct 10, 2025 | Supported |
| $50M | “fifty million dollars” | Sam Lessin: BuzzFeed trades at 33 cents with a $50M market cap | Sam Lessin | Sep 22, 2023 | Supported |
| $40M | “Forty million dollars” | Morgan Beller: A failing NFX portfolio company is sitting on $40M cash | Morgan Beller | Apr 18, 2025 | — |
| $34M | “Thirty four million dollars” | Perplexity AI generated $34 million in revenue in 2024 | Jessica Lessin | Aug 15, 2025 | Supported |
| $33M | “thirty-three million dollars” | Sam Lessin: BuzzFeed's valuation is $33 million | Sam Lessin | Dec 19, 2025 | Supported |
| $32M | “thirty-two million dollars” | Brit Morin: AI companies are spending $332 million on Super Bowl ads | Brit Morin | Feb 7, 2025 | Contradicted |
| $20M | “Twenty million dollars” | Jessica Lessin: TikTok Pays Microsoft $20M a Month for Azure OpenAI | Jessica Lessin | Aug 2, 2024 | Supported |
| $20M | “twenty million dollars” | Lessin: AI wealth will pump $20M+ SV homes while $1M homes fall | Sam Lessin | Jun 13, 2025 | — |
| $10M | “ten million dollars” | Lessin: Trial revealed Altman paid Brockman $10M from family office | Jessica Lessin | May 8, 2026 | Partly supported |
| $10M | “ten million dollars” | Sam Lessin: Owning a $10M Business Is Easier Than a $1B Exit | Sam Lessin | Jun 7, 2024 | — |
| $10M | “ten million dollars” | Sam Lessin says retaining employees with compensation fails beyond $10 million | Sam Lessin | Aug 1, 2025 | — |
| $8M | “eight million dollars” | Lessin plans to buy a $25k satirical AI billboard on Highway 101 | Sam Lessin | Feb 7, 2025 | — |
| $5M | “five million dollars” | Morin: Social app Yope raised $5M at a $50M valuation | Brit Morin | Feb 28, 2025 | Partly supported |
| $3M | “three million dollars” | Lessin: AI seed investing is a fool's errand | Sam Lessin | Dec 27, 2024 | — |
| $3M | “three million dollars” | Lessin: Seed-stage AI investing is a fool's errand for venture capitalists | Sam Lessin | Jun 14, 2024 | — |
| $3M | “three million dollars” | Dave Morin: Reddit and Truth Social have comparable market caps despite revenue disparity | Dave Morin | Mar 29, 2024 | Partly supported |
| $2M | “two million dollars” | Sam Lessin: AI Has Destroyed Seed-Stage Startup Diligence | Sam Lessin | Aug 8, 2025 | — |
| $2M | “two million dollars” | Khosla: Automatically funding anyone leaving Google DeepMind is a bad strategy | Vinod Khosla | Dec 27, 2024 | — |
| $2M | “two million dollars” | Dave Morin: AI built an app in weeks that previously cost $1M-$2M | Dave Morin | Oct 11, 2024 | — |
| $2M | “two million dollars” | Khosla: Blindly funding Google DeepMind spinouts with $2M seed checks is bad | Vinod Khosla | Jun 14, 2024 | — |
| $2M | “two million dollars” | Morin: Protein bar maker David is on trajectory toward $100M revenue | Brit Morin | May 30, 2025 | — |
| $1.5M | “a half million dollars” | Sam Lessin: Founders will increasingly pitch rounds aimed at immediate profitability | Sam Lessin | Nov 17, 2023 | — |
| $1M | “a million dollars” | Lessin: Over 50 Substack Writers Make More Than $1M Annually | Jessica Lessin | Jun 6, 2025 | — |
| $1M | “a million dollars” | Sam Lessin wagers $1M that no human sets foot on Mars by 2040 | Sam Lessin | Mar 14, 2025 | Open |
| $1K | “a thousand dollars” | Sam Lessin: I spend roughly $1,000 a month on OpenAI APIs | Sam Lessin | Aug 22, 2025 | — |
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