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Prediction Open · timeframe Jul 2031
Curative Headcount Will Shrink In Short Term Due To AI
“We're about 650 people now. In five years we'll probably be bigger. In the short term I think we're going to be quite a bit smaller.”
Fred Turner Jul 18, 2026 ▶ 1:02:03 We Built Our Own Salesforce in Months. Here's Why We're Cancelling the $600K Contract | Curative CEO
Prediction Open · timeframe Jul 2031
Lemkin: Adobe's Marketo is in terminal decay and heading to zero revenue
“It is going to zero. It is, but it is one of the slowest decays you can get, right? Because moving off a marketing automation system in the enterprise is very slow, but it is without question going to zero. There are no net new logos and everyone hates it.”
Jason Lemkin Jul 16, 2026 ▶ 1:19:37 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2029
Arora: Companies will cut G&A headcount by half within three years
“My rule of thumb is that in the next three years, we'll probably have half the people in GNA type activities in companies. Things like marketing, things like finance, things like HR, because there's a lot of process management there, and a lot of process manag…”
Nikesh Arora Jun 22, 2026 ▶ 13:32 Nikesh Arora on the Frontier Model Problem: Breadth vs Depth | The Future of Token Costs · 20VC with Harry Stebbings
Prediction Open · timeframe Jan 2027
Calacanis: Software QA departments will be destroyed by 2027 due to AI
“I think what will happen going into 2027 is an engineering QA departments will get destroyed because you'll be like, I got six QA engineers.”
Jason Lemkin Jun 4, 2026 ▶ 44:39 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2031
Rory O'Driscoll: AI Will Not Boost GDP Productivity Growth Above 2%
“Or where I stand, the statistic, the average over the last 200 years has been two percent. It'll stay at two percent.”
Rory O'Driscoll Jun 4, 2026 ▶ 59:48 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
Assertion Open · timeframe Jun 2036
Stebbings: Menlo to make $10B carry on Anthropic, Founders Fund more on SpaceX
“Menlo will make ten billion dollars in carry Spot will too, plus Founders Fund will make more than that from SpaceX.”
Harry Stebbings Jun 4, 2026 ▶ 1:25:09 Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
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
Prediction Open · timeframe Jun 2027
AI Models Will Clone End-to-End SaaS Apps Within 12 Months
“Those capabilities are going to exist in the models in the next 12 months.”
Brendan Foody Jun 1, 2026 ▶ 36:57 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
Assertion Open
Meta Offered an AI Candidate $20 Million Per Year in Cash
“There was someone I was hiring the other day, and he had an offer for twenty million dollars in cash per year from TBD, and like that's the kind of stuff we run into on a regular basis.”
Brendan Foody Jun 1, 2026 ▶ 1:03:48 Mercor CEO: Why Application Layer Companies Have No Moat & The Cost of Hiring AI Researchers · 20VC with Harry Stebbings
Prediction Open · timeframe May 2031
Josh Browder: Anthropic will reach $1 trillion in revenue
“I think Anthropic will get to a trillion in revenue.”
Josh Browder May 18, 2026 ▶ 1:29:57 Turning Peter Thiel's $100K into $10M Angel Portfolio & Why VCs Can Be Sharks | Josh Browder · 20VC with Harry Stebbings
Prediction Open · timeframe May 2027
Lemkin: Traditional marketing automation software obsolete within one year
“I don't think in a year we're going to need any traditional marketing automation software. It's too dated. It doesn't work for agents marketing.”
Jason Lemkin May 14, 2026 ▶ 35:09 Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2027
Adam Foroughi: AppLovin Employees Who Avoid AI Technology Will Be Fired
“If you avoid utilizing these technologies, you're not, and you're gonna get fired, and that's life, and so we demand that the people who are at the company are adopting these technologies rapidly to create more output, but we don't shy away from different diff…”
Adam Foroughi Apr 27, 2026 ▶ 1:06:35 AppLovin CEO: Why Founders Shouldn't Angel Invest & Why the Best Don't Need Mentorship · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2031
Levie: There will be more lawyers in 5 years than today
“There are going to be more lawyers in the next five years than we have today.”
Aaron Levie Apr 20, 2026 ▶ 0:40 Aaron Levie: Everyone is Wrong; We'll Have More Developers in 5 Years · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2031
Levie: Box will have more software engineers in five years
“We will.”
Aaron Levie Apr 20, 2026 ▶ 5:23 Aaron Levie: Everyone is Wrong; We'll Have More Developers in 5 Years · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2031
Rory O'Driscoll: AI will not displace 50% of white-collar workers
“I don't think we're going to unemployed, 50% of white collar workers. I think it's madness. I think it has some legitimate dangers in cyber security and bioterrorism, but they're manageable.”
Rory O'Driscoll Apr 16, 2026 ▶ 11:52 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2031
Lemkin: VCs backing late-stage AI startups below Anthropic face zero exits
“So many folks sub-anthropic are going to get their arses burned because they'll end up in the dead zone. They'll have great companies without great IPOs and zero M and A opportunities.”
Jason Lemkin Mar 26, 2026 ▶ 1:08:49 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
Prediction Open · timeframe Dec 2027
Lemkin: Junior role elimination will spread to sales by 2027
“This is my big worry for 20, 27 is it happens. It's going to be true in sales. It's already true in support.”
Jason Lemkin Mar 12, 2026 ▶ 32:38 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2031
O'Driscoll: AI will not drive overall US unemployment above 10%
“Over the, again, I want to be over the medium term, the technology takes longer to diffuse than we in Silicon Valley allow, and people are more adaptable. So over the medium, I'm not, I don't see any kind of 10% plus tech of an unemployment.”
Rory O'Driscoll Mar 12, 2026 ▶ 38:04 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2029
Zinman: Monday.com has hit bottom and will grow from here
“And if you ask me today how I feel great because as I told you, we hit the bottom or maybe close to the bottom. And from here we can only grow and focus on execution.”
Eran Zinman Mar 2, 2026 ▶ 59:22 Monday.com CEO on Is SaaS Dead: Will Everything Be Vibe Coded | Eran Zinman · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2031
Jerry Murdock: AI disruption will cause tech private equity firms to fail
“And so they'll be stories like that. I don't know about Bravo or anybody else, but they'll definitely be PE firms that end up like Forsman Little.”
Jerry Murdock Feb 28, 2026 ▶ 32:22 The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2029
Lemkin: Shopify and Monday will be killed by vertical AI startups
“So they're going to get killed by the startup that does it. They're going to get killed. Killed.”
Jason Lemkin Feb 26, 2026 ▶ 16:39 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2030
Stebbings: AI and Waymo could displace 30-40M workers in four years
“If we want to add in Waymo and what it'll do for self-driving within a four year period, Gosh, I think you could see 30 to forty million people.”
Harry Stebbings Feb 26, 2026 ▶ 43:20 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2027
Lemkin: A major tech leader will lay off 50% of staff in one day within 12 months
“I said, one of the leaders in the next 12 months is going to do an Elon Musk and just cut half their team in one day. They're going to lay off half the entire company.”
Jason Lemkin Feb 26, 2026 ▶ 48:30 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2031
Emberikos: AI automation will create more software builders in five years
“Yeah. And I, you know, sometimes we change what terms mean, right? Like the term computer now refers to something else, but now we have the term software engineer. And so I definitely think we'll have many more builders.”
Alexander Emberikos Feb 21, 2026 ▶ 3:42 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2031
Emberikos: AI will not eliminate enterprise sales and marketing teams
“But going back to the sales and marketing thing, like, I don't think that goes away because I think that's as, like I said, I think that's just gotten harder as the markets, any given market gets more competitive with more software out there.”
Alexander Emberikos Feb 21, 2026 ▶ 16:53 OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
Assertion Open
Lemkin: Chamath Palihapitiya has been sued by all his former partners
“Chamath, all his ex-partners have sued him. Mamoon sued them. The Grok guys he sued.”
Jason Lemkin Feb 19, 2026 ▶ 1:15:46 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2027
Siemiatkowski: SaaS revenue multiples could decline to 1x-2x price-to-sales
“But if you look at utilities, normal companies that are more utility, They may trade at one to two. So I, from that perspective, you would argue there is still some unfortunate potential to come down even further. Is it going to be, look at Chegg in the US, ri…”
Sebastian Siemiatkowski Feb 16, 2026 ▶ 3:44 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2029
Stebbings: 20VC will not invest in per-seat software pricing models
“If they sell per seat, we're not doing it. We need to replace jobs. Like labor displacement is what we're investing into. And that's the only way that we can actually return the amount of money that we need to now to make funds worth it.”
Harry Stebbings Feb 16, 2026 ▶ 19:06 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2036
Cohen: Form-based software like Salesforce will be obsolete within 10 years
“I think I called out Salesforce back then, as I cannot imagine people using something like this in the next 10 years. I think AI accelerates this.”
Ariel Cohen Feb 7, 2026 ▶ 16:44 20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen
Prediction Open · timeframe Feb 2031
Cohen: Navan will ultimately capture the entire corporate travel market
“And I think as the, as long as we will service our customers and our users, the business will continue to gain share. We're going to take the entire market. I really believe in it.”
Ariel Cohen Feb 7, 2026 ▶ 36:38 20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen
Prediction Open · timeframe Nov 2026
Lemkin: Tesla is months away from allowing owners to profit off robotaxis
“As soon as this really works, and maybe it's only single digit months away, he has millions of people who could be paid more than their lease price to allow the car into the fleet. And when he said this a decade ago, it sounded effing insane. He said that your…”
Jason Lemkin Feb 5, 2026 ▶ 1:16:35 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
Prediction Open · timeframe Feb 2029
Zeev will not change deployment pace for LP vintage preferences
“I'm going to do my thing, and if it works for them, fine, and if not, they can opt themselves out, and some of them have, and it's fine. Good people opted out, and it's fine. I'm not going to do things differently.”
Oren Zeev Feb 2, 2026 ▶ 28:54 Oren Zeev: Why AI Growth Expectations Are BS & Won't Last? Why GPs Shouldn't Tell LPs Their Strategy
Prediction Open · timeframe Jan 2029
O'Driscoll: Google Search ad dollars will shift to OpenAI
“Their cash cow, which kicks off 200 and forty-odd billion a year of revenue, which is the ads business, Isn't the best product on the market anymore, and some of those dollars will go to open AI, and because it's better real estate.”
Rory O'Driscoll Jan 22, 2026 ▶ 52:01 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
Prediction Open · timeframe Jan 2031
Weinberg: AI won't replace junior lawyers, law firms will do more work
“I don't think so. I think we'll just get more work.”
Winston Weinberg Jan 19, 2026 ▶ 40:08 Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2026
Lemkin: SpaceX, Canva, Databricks, and Anthropic will IPO in 2026
“I think we see four IPOs backloaded next year. SpaceX goes out first. Canva comes out of nowhere second. Databricks does it in the back half of the year because it's just time. Anthropic does it at the end of the year. OpenAI probably should have gone first, b…”
Jason Lemkin Dec 22, 2025 ▶ 0:00 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2026
Calacanis: Standalone marketing software will disappear by 2026
“In 2026 26, there will be no such thing as marketing software that got Klaviyo public. Marketing sales support have already converged to one agent.”
Jason Lemkin Dec 18, 2025 ▶ 36:01 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2030
Rory O'Driscoll: Anthropic will reach profitability and IPO while OpenAI faces overcommitment
“I think the difference between Anthropix and OpenAI is, OpenAI has more ambition, perhaps, but it's more likely to just get caught In the middle with commitments it can't meet. Whereas I think Entropic is very sensibly and boringly converging on profitability,…”
Rory O'Driscoll Dec 18, 2025 ▶ 1:20:31 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
Assertion Open · timeframe Dec 2030
Lemkin: Drift Is Completely Dead After Being Banned by Salesforce
“They kicked Drift off five months ago. Drift will never come back. It is dead. It is completely dead.”
Jason Lemkin Dec 4, 2025 ▶ 16:58 Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
Prediction Open · timeframe Nov 2028
Jason Lemkin: Most B2B software unicorns will fail transitioning to AI
“This is why I think most of our unicorns will fail. Because you've got to be as good or better than Owen to make this transition. Most of them are going to fail. When I look at so many of these B to B unicorns, they just, it's so hard to do both.”
Jason Lemkin Nov 27, 2025 ▶ 52:14 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2027
Jason Lemkin: Generative Engine Optimization AI software is snake oil
“I view the pro what there is a category of snake oil AI of which geo is one of them. Okay. And I'll tell you why it's snake oil. And it's gonna die in 26 or 27.”
Jason Lemkin Nov 27, 2025 ▶ 1:09:21 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Assertion Open · timeframe Nov 2026
Tunguz: Nvidia revenue concentration is 10x worse than Lucent during dot-com bubble
“So Nvidia, two customers for Nvidia represent more than 40% of revenues. Four percent represent more than 50% of revenues. I went back and looked at the dot-com era, the networking companies. NVIDIA is 10 times more concentrated in terms of revenue than Lucent…”
Tomasz Tunguz Nov 20, 2025 ▶ 43:27 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
Prediction Open · timeframe Nov 2030
Randle: CoreWeave and AI cloud providers will eventually crash 70%
“I think at some point, like they'll probably, you know, Corweave and all these things will probably go down like 70%.”
Everett Randle Nov 10, 2025 ▶ 1:17:57 Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
Assertion Open
Stebbings: Mercor hit $500M revenue run rate in 17 months
“Now this company has gone to five hundred million in revenue, faster than anyone else, I believe, in history. I think it was 17 months.”
Harry Stebbings Oct 30, 2025 ▶ 26:43 OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2030
Calacanis: VCs will lose money on 80% of B2B AI investments
“VCs are gonna lose, like, 80% of their investments in AI B to B because they're ignoring these issues, and so be it.”
Jason Lemkin Oct 23, 2025 ▶ 31:45 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Assertion Open · timeframe Oct 2026
Calacanis: AI companies built models by stealing all my copyrighted content
“Just like in the beginning to get these off the ground, we had to trample copyrights and destroy everyone's IP rights. All of my IP is stolen. Everything I've written, all my videos were taken without my consent.”
Jason Lemkin Oct 23, 2025 ▶ 1:17:07 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2030
Bouaziz predicts Deel will win its legal disputes with competitors
“I feel pretty confident that the same way we've been winning in the marketplace will win in the court of laws.”
Alex Bouaziz Oct 20, 2025 ▶ 0:00 Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2030
Lloyd: Open-Source Models Will Not Win at the AI Frontier
“I don't think open either, if I'm being honest. The reason I don't think open, like, is that it's just so damn expensive to build these things, and so what's the economic incentive?”
Zach Lloyd Oct 17, 2025 ▶ 40:38 20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp
Assertion Open · timeframe Sep 2026
Ross: Chinese AI models cost 10x more to run than US open-source
“The cost to run the OSS model is about one-tenth that of the Chinese models.”
Jonathan Ross Sep 29, 2025 ▶ 30:11 Groq Founder, Jonathan Ross: OpenAI & Anthropic Will Build Their Own Chips & Will NVIDIA Hit $10TRN · 20VC with Harry Stebbings
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