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Dated predictions on 44 shows and their status, on one timeline. Left of today: already assessed. Green held up, red didn't hold up, amber partly. Right: still open; when a dot's date hits, the ledger checks it again against the public record.

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Everyone Jason Lemkin (127)Chamath Palihapitiya (119)Rory O'Driscoll (115)Jason Calacanis (78)David Sacks (69)David Friedberg (63)Harry Stebbings (47)David Senra (45)Brad Gerstner (43)Alex Kantrowitz (38)John Coogan (37)Shaan Puri (36)
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Next up (41)

13 days left 2026-09-26
20VC Prediction Open · timeframe Sep 2026
O'Driscoll: Markets won't sustain a $400B valuation bump from Musk's fab announcement
“I am significantly more skeptical That six months from now, people are going to attribute another 400 billion of value to a statement that I'm going to build a fab.”
Rory O'Driscoll Mar 26, 2026 ▶ 17:37 Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
47 days left 2026-10-30
20VC Prediction Open · timeframe Oct 2026
O'Driscoll: Analysts will soon press Benioff on Salesforce AI agent API calls
“And I'm willing to bet in a quarter or two, someone's going to be asking Benioff for how many calls to your agent, your headless API did you get?”
Rory O'Driscoll Apr 30, 2026 ▶ 12:41 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
76 days left 2026-11-28
20VC Prediction Open · timeframe Nov 2026
O'Driscoll: Anthropic Will Pass OpenAI in Scale and Profitability Shortly
“Within a couple of quarters, Anthropic will be visibly and obviously ahead. Profitable, growing more quickly, and bigger.”
Rory O'Driscoll May 28, 2026 ▶ 0:14 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
O'Driscoll: Anthropic will likely IPO in 2026, but Stripe will not
“I think Stripe, least likely, take it off the table. My gut would be Antropic gets it done.”
Rory O'Driscoll Dec 22, 2025 ▶ 1:02:17 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
O'Driscoll: OpenAI will not surpass an $800B valuation by late 2026
“Under. I'll tell you what I'm doing mentally. I'm just, I mean, there's no logic. I'm just looking at the step ups in the rounds as you'd expect are getting smaller, right? You know, you get two or five X and then you have, you go from 80 to one 50, which is a…”
Rory O'Driscoll Jul 31, 2025 ▶ 1:19:00 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
O'Driscoll: AI capex overinvestment cycle will not correct in 2026
“Until that happens. We're going to over invest. And I don't think it's happening in 20, 26.”
Rory O'Driscoll Mar 12, 2026 ▶ 23:24 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
O'Driscoll: Anthropic will target a public market debut in Q4
“So my assumption is these guys are going to go public, as we said, October Q-IV time period if they can.”
Rory O'Driscoll Apr 23, 2026 ▶ 47:13 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
O'Driscoll: Anthropic still has over 50% chance of IPOing this year
“I mean, statistically, more than 50%, yes, because in a world where this doesn't get solved for four or five months, there's so many other problems that our heads are gonna hurt, right? So you have to say, if a problem, in a world where it does get solved, the…”
Rory O'Driscoll Jun 18, 2026 ▶ 38:10 Anthropic's Fable Banned by US Government | Wix & Adobe Hit All-Time Lows | Mistral Raising at $20BN · 20VC with Harry Stebbings
215 days left 2027-04-16
20VC Prediction Open · timeframe Apr 2027
O'Driscoll: Tech giants won't cut AI spending in 2026, keeping Nvidia sold out
“No one's going to blink on their investments for twenty-twenty-six. You actually know the next four quarters of NVIDIA announcement. You know the next four quarters of every one of the infrastructure, which is every single thing we can make. If you can count t…”
Rory O'Driscoll Apr 16, 2026 ▶ 53:38 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
237 days left 2027-05-08
20VC Prediction Open · timeframe May 2027
O'Driscoll: AI will not cause mass unemployment within 12 to 24 months
“I don't buy the mass unemployment in 12, 24 months.”
Rory O'Driscoll May 8, 2025 ▶ 32:21 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
237 days left 2027-05-08
20VC Prediction Open · timeframe May 2027
O'Driscoll: AI markets will consolidate into 3-4 dominant players
“I think that what a successful set of products at AI starts to gel over the next couple of years, and the people who are in the lead at that point in time get a similar ten-year run to, you know, the ten-year runs you and I both benefited from in SaaS, Jason, …”
Rory O'Driscoll May 8, 2025 ▶ 1:07:17 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
264 days left 2027-06-04
20VC Prediction Open · timeframe Jun 2027
O'Driscoll: Current frontier AI models will be 5x-10x cheaper in a year
“The frontier models aren't getting cheaper. I want to be clear on that. They're getting actually slightly more expensive, but the model that is frontier today will in a year be five to 10 X cheaper because it won't be the frontier model anymore.”
Rory O'Driscoll Jun 4, 2026 ▶ 35:01 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
292 days left 2027-07-02
20VC Prediction Open · timeframe Jul 2027
O'Driscoll: Kalshi will not reach $100B valuation within 12 months
“I doubt it.”
Rory O'Driscoll Jul 2, 2026 ▶ 39:57 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
412 days left 2027-10-30
20VC Prediction Open · timeframe Oct 2027
O'Driscoll: OpenAI will reach a $1 trillion valuation in two years
“On the current trajectory, maybe all I can answer is on the current trajectory and without the euphoria Jason mentioned, it's probably two years because, you know, you do get some attenuation of growth at scale and, you know, at the current thing that, I mean,…”
Rory O'Driscoll Oct 30, 2025 ▶ 13:15 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
426 days left 2027-11-13
20VC Prediction Open · timeframe Nov 2027
O'Driscoll: Palantir and AI CapEx Will Face a Major Correction Within Two Years
“I think, Michael, it's very hard to imagine a company trading north of a 110, 120 times revenues like Palantir, growing at 50 or 60% last quarter. Great. Amazing quarter. Kicking off cash. It's very hard not to imagine the next two years that doesn't have a si…”
Rory O'Driscoll Nov 13, 2025 ▶ 12:50 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
474 days left 2027-12-31
20VC Prediction Open · timeframe Dec 2027
O'Driscoll: Rising memory chip costs will drive up iPhone prices next year
“I think that you're going to see some impact of that right down to the price of your iPhone next year.”
Rory O'Driscoll May 7, 2026 ▶ 40:50 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
503 days left 2028-01-29
20VC Prediction Open · timeframe Jan 2028
O'Driscoll: AI CapEx spend won't pull back in the next 12-24 months
“So I think it's highly unlikely that you know, this is not going to be the year when people get terrified and say, I'm not going to do it. At some point, I think they will, because I think we probably are over-investing at some level, but right now, people are…”
Rory O'Driscoll Jan 29, 2026 ▶ 35:16 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
524 days left 2028-02-19
20VC Prediction Open · timeframe Feb 2028
O'Driscoll: Enterprise AI spending will surge for two years before retrenchment
“My gut would be people will overbet, overinvest, and you will have a retrenchment period, you know, two plus years from now, but I think right now you're just looking at two years where, you know, just as the hyperscaler said two years ago, we're going to do t…”
Rory O'Driscoll Feb 19, 2026 ▶ 15:45 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
679 days left 2028-07-23
20VC Prediction Open · timeframe Jul 2028
O'Driscoll: DRAM Memory Pricing Will Suffer Brutal Collapse in 1-2 Years
“And when that, the big aha for me is when that Pricing breaks. It'll be brutal to the downside, but maybe that's a year, two years from now.”
Rory O'Driscoll Jul 23, 2026 ▶ 1:24:03 Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
995 days left 2029-06-04
20VC Prediction Open · timeframe Jun 2029
Rory O'Driscoll: AI will not cause mass white-collar unemployment in 3 years
“And we've grown to accept that, that, you know, we're all here in the Valley with a plan. To automate white collar work such that there's going to be mass unemployment, according to these folks who are totally wrong, in my opinion, in three years, and all the …”
Rory O'Driscoll Jun 4, 2026 ▶ 1:36:49 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
1205 days left 2029-12-31
20VC Prediction Open · timeframe Dec 2029
O'Driscoll: The 2020s will produce two trillion-dollar startup outcomes
“I think you're going to have one trillion dollar outcome from the last decade and two, it looks like from this decade, if it all happens according to plan.”
Rory O'Driscoll Jun 11, 2026 ▶ 13:11 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
1206 days left 2030-01-01
20VC Prediction Open · timeframe Jan 2030
O'Driscoll: Starlink Will Drive Most of SpaceX's Value by 2030
“I think Starlink will be the vast portion of the value. The value, I don't think data centers in space will be a meaningful percentage of revenue.”
Rory O'Driscoll May 28, 2026 ▶ 55:39 OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
1347 days left 2030-05-22
20VC Prediction Open · timeframe May 2030
O'Driscoll: Only 2 or 3 foundational AI model providers will survive
“I don't buy the commodification argument. There's going to be two or three of them. I don't think there's going to be 10”
Rory O'Driscoll May 22, 2025 ▶ 1:14:35 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
1354 days left 2030-05-29
20VC Prediction Open · timeframe May 2030
O'Driscoll: OpenAI's hardware effort will fizzle within three to five years
“And then my predict, my guess is statistically the likely outcome just based on the priors of the other companies in the space is three, five years later, it turns into a fizzle. It was, it wasn't product. It didn't pan out”
Rory O'Driscoll May 29, 2025 ▶ 47:39 OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
1410 days left 2030-07-24
20VC Prediction Open · timeframe Jul 2030
O'Driscoll: Half of all seed funds will shut down within five years
“The answer is less. Half of everybody's gonna die.”
Rory O'Driscoll Jul 24, 2025 ▶ 1:11:48 How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
1431 days left 2030-08-14
20VC Prediction Open · timeframe Aug 2030
O'Driscoll: Palantir Market Cap Will Not Reach $2 Trillion in Five Years
“I just think compounding to two trillion from here is pretty damn hard. So I'm a no.”
Rory O'Driscoll Aug 14, 2025 ▶ 1:29:13 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
1438 days left 2030-08-21
20VC Prediction Open · timeframe Aug 2030
O'Driscoll: AI debt models require three to five years of CapEx growth
“All this depends on three to five more years of continued AI CapEx expansion. If that's the case, everything works, and if that's not the case, all bets are off.”
Rory O'Driscoll Aug 21, 2025 ▶ 1:00:27 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
1620 days left 2031-02-19
20VC Prediction Open · timeframe Feb 2031
O'Driscoll: SaaS companies ignoring AI will see multiples fall to 4x-5x
“If you don't get on top of this soon, That 10 X revenues is going to go on a five and four and where the other seven percent growth was are. Fast forward five years, there's really only one or two stories. They get on top of this, they get a third market share…”
Rory O'Driscoll Feb 19, 2026 ▶ 36:08 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
1725 days left 2031-06-04
20VC Prediction Open · timeframe Jun 2031
O'Driscoll: AI vendors will standardly sell software to law firms in 5 years
“Fast forward five years, to be clear, I think there will be AI-focused service providers, two law firms, they'll buy the product and the drama will be out of the deal.”
Rory O'Driscoll Jun 4, 2026 ▶ 1:08:01 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
1739 days left 2031-06-18
20VC Prediction Open · timeframe Jun 2031
O'Driscoll: AI frontier market will consolidate into 2-3 US players
“Fast forward five years, you know, unless the U.S. Is ludicrously obnoxious in its sovereignty acts, it should be a small oligopoly like Cloud of two to three players in the U.S. With some kind of affiliations in Europe, and that is the likely structure of the…”
Rory O'Driscoll Jun 18, 2026 ▶ 45:08 Anthropic's Fable Banned by US Government | Wix & Adobe Hit All-Time Lows | Mistral Raising at $20BN · 20VC with Harry Stebbings
1760 days left 2031-07-09
20VC Prediction Open · timeframe Jul 2031
O'Driscoll: AI Will Not Replace 50% of White-Collar Jobs in 5 Years
“I mean, look, in five years' time, if Dario is correct, and 50% of white-collar jobs have been replaced by AI, which I don't believe for a second, Then you damn right. There's going to be political. Political controversy. And if you think five percent is going…”
Rory O'Driscoll Jul 9, 2026 ▶ 12:38 Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
1831 days left 2031-09-18
20VC Prediction Open · timeframe Sep 2031
O'Driscoll: Oracle will not collect $300B from OpenAI in 5-6 years
“Do I think the full last three hundred billion dollars will be wired in five or six years? No. I very much doubt it.”
Rory O'Driscoll Sep 18, 2025 ▶ 34:03 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
2078 days left 2032-05-22
20VC Prediction Open · timeframe May 2032
O'Driscoll: Four or more venture exits will top $65B in 5-7 years
“If there's not four exits, Above sixty five billion in the next five or seven years, then the people who bought Stripe, SpaceX, Databricks, OpenAI and Antropic are screwed. So I don't think they're screwed. So I think there's going to be, this trend is going t…”
Rory O'Driscoll May 22, 2025 ▶ 31:41 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
2211 days left 2032-10-02
20VC Prediction Open · timeframe Oct 2032
O'Driscoll: OpenAI must hit $200B-$300B revenue or AI market faces severe crash
“One of two things is going to happen in the next five or seven years, right? Either A, you know, you are going to see pretty profound productivity changes. You're going to see companies like OpenAI literally being two to three hundred billion dollars in revenu…”
Rory O'Driscoll Oct 2, 2025 ▶ 29:06 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
2301 days left 2032-12-31
SAASTR Prediction Open · timeframe Dec 2032
O'Driscoll: OpenAI and Anthropic Revenues Won't Match AI CapEx Until 2031-2032
“The stunning thing is it takes until 2031 or 2032 before The revenue from those two companies surpasses the total capex.”
Rory O'Driscoll Jul 15, 2026 ▶ 6:56 Software Isn't Dead. It's Gotten Harder with Scale Venture Partners' Rory O'Driscoll
3250 days left 2035-08-07
20VC Prediction Open · timeframe Aug 2035
Rory O'Driscoll: AI App Revenue Will Reach $300B–$400B in 10 Years
“If you fast forward 10 years, that 25, thirty billion of apps, wherever, and you could easily be three, four hundred billion dollars.”
Rory O'Driscoll Aug 7, 2025 ▶ 59:03 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
3453 days left 2036-02-26
20VC Prediction Open · timeframe Feb 2036
O'Driscoll: Only AI-led applications will grow over the next decade
“I think intelligence-led applications are the only applications that are going to sell And grow quickly over the next 10 years. Non-intelligent-led applications will at best be flat to mild growth if they're not obviously disrupted by intelligence, and at wors…”
Rory O'Driscoll Feb 26, 2026 ▶ 17:07 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
3496 days left 2036-04-09
20VC Prediction Open · timeframe Apr 2036
Rory O'Driscoll: Supabase Will Become a Legacy Database Within 10 Years
“Over the next five years, that will mean adding complexity, adding functionality. And in 10 years time, someone, and it won't be me at that point, will be saying, oh, my God, those legacy Superbase products, they're almost as bad as MongoDB, and there'll be a …”
Rory O'Driscoll Apr 9, 2026 ▶ 1:08:19 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
3510 days left 2036-04-23
20VC Prediction Open · timeframe Apr 2036
O'Driscoll: Cursor Deal Will Be Private M&A Peak for Next Decade
“I think this will stand as the high watermark of private M&A for a decade.”
Rory O'Driscoll Apr 23, 2026 ▶ 24:00 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
3510 days left 2036-04-23
20VC Prediction Open · timeframe Apr 2036
O'Driscoll: Core payroll SaaS will survive and compound over next decade
“These are entire businesses that, you know, might have some impact at the margin in terms of agentic efficiency, but this core business will be there in five, 10 years' time. It'll compound because payroll is not, not everything is, I mean, it's, we're actuall…”
Rory O'Driscoll Apr 23, 2026 ▶ 1:13:28 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
6812 days left 2045-05-08
20VC Prediction Open · timeframe May 2045
O'Driscoll: GDP and productivity growth will remain at 2% for 20 years
“I think GDP growth and productivity growth has been roughly two percent since the dawn of the industrial revolution. And I'm willing to lean into the fact that it'll be two percent for the next 20 years.”
Rory O'Driscoll May 8, 2025 ▶ 37:38 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings

Due for another look (1)

20VC Prediction Open · timeframe Dec 2025
Rory O'Driscoll: OpenAI will publicly accuse Microsoft of antitrust in 2025
“Accused, by the way, is a wonderfully vague word. Will they file a lawsuit and prevail? Maybe not, but will Sam throw words out? Yeah. That two and a half x on a yes, I'd take that chance.”
Rory O'Driscoll Jun 26, 2025 ▶ 1:07:55 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings

Closed calls (53) the full record →

20VC Prediction Didn’t hold up
O'Driscoll: Customer support applications will not require or use frontier AI models
“Customer support will not be using frontier models.”
Rory O'Driscoll Aug 5, 2026 ▶ 36:19 Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
20VC Prediction Didn’t hold up
O'Driscoll: Software valuations will never reach 20x revenue multiples again
“Give me 30% growth, give me profits, give me a story that's got some future in it, and I'll get you back to five times. I'll never give you 20 times again. I won't fall for that one this time.”
Rory O'Driscoll May 14, 2026 ▶ 46:14 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: AI labs will throttle subscriptions and hike prices for compute
“You're going to see some compute rationally, people are going to start allocating tokens to the highest, effectively the highest bidder. You're going to see a lot of throttling, like, you're going to see these plans, like, that's why they shot Sora. You're goi…”
Rory O'Driscoll Apr 16, 2026 ▶ 54:11 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Oracle will lay off 20k to 30k employees over AI capex strain
“The only person that's even struggling slightly to cover their nut is Oracle, right? Because they had the weakest balance sheet and the least compelling use case, which is why at some point they're going to throw 20 or 30,000 people over the side to make the P…”
Rory O'Driscoll Mar 12, 2026 ▶ 23:30 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
O'Driscoll: OpenAI Will Capture All Ad-Buying Value Natively Without Ad-Tech
“So I think for the paid ads, all the value that's going to be captured is going to be captured by OpenAI, and there's not going to be a optimization engine.”
Rory O'Driscoll Jan 22, 2026 ▶ 57:40 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: US fintechs will use anti-China messaging against foreign rivals
“Competitors are going to be the people who use it first. Because if I was an all-American fintech company, I'd have my all-American flag out there and say, these guys are a bunch of commies. They have commies looking at your data. We're, you know, our stuff is…”
Rory O'Driscoll Dec 11, 2025 ▶ 1:24:14 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
20VC Prediction Held up
Rory O'Driscoll: ChatGPT will succeed without destroying Google Search
“The likely outcome for me is ChatGP continues to build this compelling consumer product, can command differentiated market, while at the same time Google search does not quote unquote go to zero.”
Rory O'Driscoll Nov 27, 2025 ▶ 30:30 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: AI platforms like ChatGPT will inevitably launch advertising
“I'm sure the other shoe to drop at some point is advertising. So it all makes sense because it's the only way it's one of only two ways to monetize the free users. So it's going to happen.”
Rory O'Driscoll Oct 2, 2025 ▶ 58:05 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: VC Market Will Not Return to $100 Million Funding Caps
“Yeah, I think it's maybe not as pronounced as now, but it ain't going back to everything with A's, B's and C's and nothing be more than a hundred million dollar raise.”
Rory O'Driscoll Aug 14, 2025 ▶ 1:18:18 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: FTC will investigate Big Tech's 'empty husk' deals
“So the FTC is not going to let this happen without poking around.”
Rory O'Driscoll Jul 17, 2025 ▶ 20:59 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: xAI will fail to displace ChatGPT's dominant consumer mindshare
“The market's already been taken and maybe it gets some share of it, but I don't think, yeah, I don't think you can build as big a thing. I don't think you can build, I don't think you can displace ChatGPT at scale in the minds of the consumer, which is 80, 90%…”
Rory O'Driscoll Jul 17, 2025 ▶ 1:09:50 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
O'Driscoll: AGI's arrival will be defined by Microsoft and OpenAI litigation
“My comment is we're going to hit AGI when Microsoft and OpenAI litigate what OpenAGI is.”
Rory O'Driscoll Jun 19, 2025 ▶ 42:53 Chime IPO: Are IPOs Hotter Than Ever? · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Major AI labs will inevitably acquire an AI coding app
“If they don't do if they don't do Winsurf now, the line of other coding apps outside the OpenAI office is going to go around the frickin' block. And at some point, someone's gonna buy something.”
Rory O'Driscoll Apr 24, 2025 ▶ 7:50 How LP Deployment to Venture Will Change in 2025 & Are Endowment Funds in Trouble? · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Figma will IPO soon rather than stay private
“My guess is it totally makes sense for them to get a great IPO under their belt. In a way that, and not do the strike thing of stay private for another three or four years.”
Rory O'Driscoll Jun 12, 2025 ▶ 11:48 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
O'Driscoll: Normal years won't yield over 5 exits above $10B
“Really there's not going to be more than four or five, ten billion dollar plus outcomes a year.”
Rory O'Driscoll Jun 4, 2026 ▶ 10:50 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Major cybersecurity incumbents will aggressively acquire agentic AI security startups
“So I think there'll be a ton of fast acquisitions as agent security solutions emerge, you know, and people will be doing, if they're smart, and I think those two companies are extraordinarily smart, they'll be doing acquisitions long before it's quote certain …”
Rory O'Driscoll Apr 2, 2026 ▶ 26:08 OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Meta will lay off employees to fund Nvidia hardware purchases
“And that depreciation is going to start hitting, and they're going to be firing people because they need to give it to Jensen.”
Rory O'Driscoll Mar 19, 2026 ▶ 15:53 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
20VC Prediction Partly held up
O'Driscoll: Anthropic and SpaceX's next funding rounds will be IPOs
“You've got to believe that the next round for this, Antropic, and SpaceX are all public offerings.”
Rory O'Driscoll Mar 5, 2026 ▶ 26:30 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Adobe Acquired SEMrush to Launch an Answer Engine Optimization Product
“SEMrush, which is the king of search engine optimization for Google, got acquired recently by Adobe, and I think that acquisition only makes sense if their plan is as quickly as is humanly possible to introduce an answer engine optimization product, because th…”
Rory O'Driscoll Jan 22, 2026 ▶ 58:11 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
O'Driscoll: Anthropic's $10B raise will likely be its last before IPO
“I think it probably will be the last one before the IPO.”
Rory O'Driscoll Jan 15, 2026 ▶ 1:49 Anthropic’s $10B Raise | a16z’s $15B Fund: Is the Middle Dead in VC? | How OpenAI Could Go to Zero? · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: OpenAI and Anthropic can become $500B-$1T companies without AGI
“I think both of these companies can be plus or minus, you know, half a trillion to trillion dollar companies.”
Rory O'Driscoll Aug 14, 2025 ▶ 13:08 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Benchmark will hire replacement partners and remain successful
“Benchmark will be fine. So let's start with that. They'll find two other people to fill those slots and they'll be fine because they've been fine for 30 years.”
Rory O'Driscoll Jul 31, 2025 ▶ 2:20 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Slack restricting customer data access will fail over the medium term
“I don't know if you can get away forever in a horizontal app like Salesforce with a channel like Slack denying access, the denying the customer access to their own content over the medium term. I don't think it stands.”
Rory O'Driscoll Jun 26, 2025 ▶ 1:04:10 Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
20VC Prediction Held up
O'Driscoll: Chime will expand into offering loans and cross-sell products
“They're going to add, you know, loans, which they don't really do a lot of today and all the other cross sell stuff that every financial services company does at scale.”
Rory O'Driscoll May 22, 2025 ▶ 3:56 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
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