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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 (33)

5 days left 2026-09-18
20VC Prediction Open · timeframe Sep 2026
Lemkin Predicts Adobe Share Price Will Drop At Least 10%
“I'm betting down at least 10%.”
Jason Lemkin Sep 18, 2025 ▶ 1:27:14 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
53 days left 2026-11-05
20VC 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
109 days left 2026-12-31
SAASTR Prediction Open · timeframe Dec 2026
Lemkin: VC Dollars in 2026 Will Surpass 2021 Peak
“And again, I think 26 will be even bigger. So we'll surpass the dollars of 21.”
Jason Lemkin Jan 2, 2026 ▶ 16:06 AI + B2B in 2026: Find the Tailwinds or Get Left Behind | Jason Lemkin
109 days left 2026-12-31
SAASTR Prediction Open · timeframe Dec 2026
Lemkin: Sales Commission Rates Will Halve by End of 2026
“I actually think what's going to happen because of attribution is commissions are going to have by the end of next year. Because this is how the math is going to work. You're going to get credit for the It's not just PLG. You're going to get credit for Kyle's …”
Jason Lemkin May 28, 2025 ▶ 25:50 AI, Sales + GTM in 2026: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton
109 days left 2026-12-31
20VC 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
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
Lemkin: Three of today's top six B2B stocks will retain 2026 leadership
“My Pekumumusukus, Pekumumusukus, Palantir, Cloudflare, Mongo, Shopify, CrowdStrike, Snowflake, I'll bet you 10 grand, three of them are in the top six of this cohort at the end of next year.”
Jason Lemkin Dec 22, 2025 ▶ 40:01 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
Lemkin: Custom chip competition will not threaten Nvidia's dominance in 2026
“You're a fool to invest against Nvidia for 2026. And I think you are arguably a fool to invest into Amazon in 20, 26 for a simple reason. Just a simple, I didn't say 20, 27 or 20, 28. It is not enough time for all this competition to come online. It is not eno…”
Jason Lemkin Dec 22, 2025 ▶ 57:00 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
Lemkin: Amazon stock will underperform Big Tech peers in 2026
“Amazon stocks only up two percent this year, if, and I think they're gonna, they will be the underperformer next year, for the same, there's just not enough time”
Jason Lemkin Dec 22, 2025 ▶ 57:56 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
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
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
Lemkin: Anthropic and Databricks will IPO in late 2026
“I think Anthropic and Databricks have an incentive to IPO, as best I understand it. They have an incentive. As Rory said, times are great. And so I think it'll be the, unless, unless, unless the market crashes for some reason, I think they're going to do it wh…”
Jason Lemkin Dec 11, 2025 ▶ 13:20 SpaceX Valued at $800BN & Harvey Raises $160M at an $8BN Price & Netflix Acquires Warner Brothers · 20VC with Harry Stebbings
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
Lemkin: Linda Yaccarino will remain CEO of X through 2026
“But I say she's here through the end of 2026.”
Jason Lemkin Jul 10, 2025 ▶ 1:07:32 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
Lemkin: Slack will achieve Notion-like ARPU growth from AI in 2026
“I suspect as the year goes on, we're gonna see the same thing at Slack, because most folks haven't used it, we're on it. The AI version of Slack for certain use cases is so much better. I don't love that they're not just charging another four bucks a month, bu…”
Jason Lemkin Mar 26, 2026 ▶ 58:33 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
109 days left 2026-12-31
20VC Prediction Open · timeframe Dec 2026
Lemkin: SpaceX market valuation will triple in 2026 driven by retail investors
“I'm going to take this bet that it's going to trade up three X, In twenty-twenty-six, just based on GameStoppers driving it up.”
Jason Lemkin May 21, 2026 ▶ 59:14 Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
110 days left 2027-01-01
20VC 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
166 days left 2027-02-26
20VC 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
230 days left 2027-05-01
20VC Prediction Open · timeframe May 2027
Lemkin: AI will replace half of sales and customer success teams
“Half of these sales teams will be gone in two years. Half of these sales and customer success teams will be gone in two years because they're mediocre. They'll be gone. They're all going to be laid off.”
Jason Lemkin May 1, 2025 ▶ 1:26:41 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
236 days left 2027-05-07
20VC Prediction Open · timeframe May 2027
Lemkin: HubSpot's AI agent strategy will prove if classic SaaS can re-accelerate
“I believe over the next 12 months, this strategy, if it's real, should lead to genuine re-acceleration at HubSpot. Otherwise, it's, there's no hope for this class, these classic categories”
Jason Lemkin May 7, 2026 ▶ 50:50 Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
243 days left 2027-05-14
20VC 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
271 days left 2027-06-11
SAASTR Prediction Open · timeframe Jun 2027
Lemkin: A $100B Startup Acquisition Will Occur in the Next 12 Months
“I bet there'll be a hundred billion dollar startup acquired in the next 12 months.”
Jason Lemkin Jun 11, 2026 ▶ 14:26 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
290 days left 2027-06-30
20VC Prediction Open · timeframe Jun 2027
Lemkin: OpenAI's IPO will be delayed until mid-2027 as Altman secures alternative financing
“I think that's a good idea. I think Sam will come up with so much alternative financing. It'll slip into mid 27, but I think that's the straw man today would be my guess. Like that's the plan, but there'll be so much, so many other sources of maybe the governm…”
Jason Lemkin Nov 20, 2025 ▶ 1:23:33 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
298 days left 2027-07-08
SAASTR Prediction Open · timeframe Jul 2027
SpaceX, Anthropic, and OpenAI IPOs will exceed all past tech IPOs combined
“We're going to see three trillion dollar plus IPOs over the coming months. It's never happened before. The value of SpaceX plus Anthropic plus OpenAI will be more than all the other tech IPOs combined ever.”
Jason Lemkin Jul 8, 2026 ▶ 45:45 Agents Didn't Kill Sales. They Just Exposed It with SaaStrAI CEO and Founder Jason Lemkin
342 days left 2027-08-21
20VC Prediction Open · timeframe Aug 2027
Lemkin: Rippling will not go public for at least two more years
“Rippling needs another two years is my guess in the oven to get to that.”
Jason Lemkin Aug 21, 2025 ▶ 1:33:04 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
384 days left 2027-10-02
20VC Prediction Open · timeframe Oct 2027
Lemkin: Future GPU data centers will match city-sized power output with few humans
“So it will only be a couple years where the cities of the future don't even have humans in them. The S the next New York will all be GPUs and like 20 people managing an entire city, a New York city of data of GPUs.”
Jason Lemkin Oct 2, 2025 ▶ 45:44 Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
474 days left 2027-12-31
20VC Prediction Open · timeframe Dec 2027
Lemkin: Open Evidence will raise at $30B-$40B valuation next year
“Open Evidence will probably do a round at 30 or 40 next year. I'm actually going to suggest that Thrive is very smart. And they've probably done the math and this is the right insertion point for them. And they believe in it. And someone else is going to do it…”
Jason Lemkin Jan 29, 2026 ▶ 43:44 Anthropic Inference Costs Skyrocket |TikTok Deal Closes |The IPO Market:Wealthfront & EquipmentShare · 20VC with Harry Stebbings
474 days left 2027-12-31
20VC 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
531 days left 2028-02-26
20VC Prediction Open · timeframe Feb 2028
Lemkin: AI agents will stop requiring custom setup within two years
“Every agent, here's the problem today, and this will change in the next two years. It is not true today. Every agent is essentially custom, ok? Every agent needs to be trained. Every agent needs to be onboarded. If you want it to be great, ok? Every agent need…”
Jason Lemkin Feb 26, 2026 ▶ 14:57 Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
840 days left 2028-12-31
20VC Prediction Open · timeframe Dec 2028
Lemkin: Half of YC founders staying will transform San Francisco by 2028
“Half are going to stay and Gary's going to do this for a decade. That alone will be transform transformational to SF by, I don't know, 20, 28.”
Jason Lemkin Jan 4, 2024 ▶ 1:04:41 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
1038 days left 2029-07-17
20VC Prediction Open · timeframe Jul 2029
Lemkin: 100% of S&P 500 companies with cash will buy Bitcoin
“I think a hundred percent of S&P companies are going to buy Bitcoin over the next 48 months. A hundred percent. I think it's going to become part of the standard treasury function in the CFO's office that has cash. It's going to be part of cash management and …”
Jason Lemkin Jul 17, 2025 ▶ 1:18:32 Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
1570 days left 2030-12-31
20VC Prediction Open · timeframe Dec 2030
Lemkin: 100% chance the US venture market hits $500B by 2030
“A hundred percent chance. So maybe more than a hundred.”
Jason Lemkin Nov 20, 2025 ▶ 53:42 Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
1570 days left 2030-12-31
20VC Prediction Open · timeframe Dec 2030
Jason Lemkin predicts OpenAI will reach $100B in ad revenue
“I like this as a goal for 2030 because it's clear what people should be doing... And so I think because it is achievable, it will be achieved. I actually think it will be achieved.”
Jason Lemkin Apr 16, 2026 ▶ 49:59 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
1802 days left 2031-08-20
20VC Prediction Open · timeframe Aug 2031
Lemkin: >51% chance OpenRouter drives 20-30% of Stripe's revenue in 5 years
“I think it'll be like the scale acquisition. It will be the start of something that gets bigger, whether this brand exists or whether even this product exists five years. I don't even think this product will exist in five years, but I think it will be, I think…”
Jason Lemkin Aug 20, 2026 ▶ 26:03 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
2379 days left 2033-03-19
20VC Prediction Open · timeframe Mar 2033
Lemkin: Nvidia will reach $10 trillion cumulative bookings in 5-7 years
“I think there's a high degree of confidence that most of the roads lead back to Nvidia reaching 10 trillion of cumulative, cumulative bookings over the next five to seven years.”
Jason Lemkin Mar 19, 2026 ▶ 9:14 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
3482 days left 2036-03-26
20VC Prediction Open · timeframe Mar 2036
Lemkin: Odds Google builds a long-term Figma competitor approach zero
“I think the odds that they desire, decide to build a Figma competitor from this for a decade approach zero.”
Jason Lemkin Mar 26, 2026 ▶ 43:43 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

Due for another look (2)

20VC Prediction Open · timeframe Dec 2025
Lemkin Bets Opendoor Stock Will Hit $24 by Year-End
“I'm going 20, I'm going 24. I don't know what the bet is exactly, but I got 24.”
Jason Lemkin Sep 18, 2025 ▶ 1:24:11 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
20VC Prediction Open · timeframe Dec 2025
Lemkin: Shaun Maguire will leave Sequoia Capital in 2025
“I'll take the bet that he leaves this year.”
Jason Lemkin Jul 10, 2025 ▶ 1:00:14 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings

Closed calls (60+) the full record →

20VC Prediction Held up
Calacanis: SpaceX will go public at a valuation of $1T or more
“Tesla had to IPO. Now it was a different time. It really barely had any revenue, but same guy running them. It IPO'd at 1.7 billion, which seemed very expensive. 1.7 billion. The sister company will IPO at 1.7 trillion or one trillion.”
Jason Lemkin Dec 18, 2025 ▶ 9:46 Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: AI will enable 20-to-40-person teams to build billion-dollar companies
“If you allow for some outsourcing agencies resources that come and go, I think we will see a bunch of 20, 30, 40 person, billion dollar companies because a core of engineers, a bunch of AIs making, and people are going to be like, you know what, dude, not, I d…”
Jason Lemkin Aug 14, 2025 ▶ 1:22:03 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: Elon Musk or xAI Will Sue Apple
“He's incensed, and he's got a lot of money in XAI. I mean, he has, he's the richest man in the world, but he doesn't have unlimited capital, so I think it happens.”
Jason Lemkin Aug 14, 2025 ▶ 1:33:24 Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
20VC Prediction Partly held up
Lemkin: B2B software vendors will bundle AI for free in SMB plans
“Next generation AI for B to B, as you approach true SMB, it's more and more going to be base and included with a limited upsell opportunity.”
Jason Lemkin Jun 12, 2025 ▶ 1:02:49 Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
SAASTR Prediction Held up
Lemkin: Anthropic Will Reach $50B in Revenue in Four Years
“Anthropics revenue is like nothing we've ever seen. Okay. It'll be at fifty billion in less than four years or four years plus or minus.”
Jason Lemkin Jun 11, 2026 ▶ 27:35 $4 Trillion in IPOs, $100B in M&A, and Why B2B Spend is Booming
SAASTR Prediction Held up
Customers Will Pay Higher Prices for Canva as It Becomes Agentic
“Now people are going to start paying more for Canva as Canva gets more gentic with two point O.”
Jason Lemkin Jul 10, 2026 ▶ 22:58 $0 to $700M ARR in 16 Months. Inside Higgsfield's AI Growth with Alex Mashrabov, co-founder and CEO
20VC Prediction Held up
Lemkin: OpenAI, Anthropic, and xAI will rush IPOs due to capital pressure
“What all three of those say to me is there's no matter, there's subtle pressure around access to capital. Like they've all got to have an IPO strategy sooner than they'd hoped because Data center, because XAI needs capital, because Anthropic is even worried ab…”
Jason Lemkin Feb 5, 2026 ▶ 7:36 The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
20VC Prediction Partly held up
Lemkin: Elon Musk Will Not Settle With OpenAI and Will Win
“They ain't going to settle for that. He's going to go to trial and he's going to win.”
Jason Lemkin Jan 22, 2026 ▶ 32:46 Elon Musk vs Sam Altman | The Implosion of Thinking Machines | Can VC Survive Public Pricing? · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: Replit and Lovable will surpass $250M combined ARR
“I would say over, over two 50, but barely.”
Jason Lemkin Oct 9, 2025 ▶ 1:29:34 OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
20VC Prediction Partly held up
Lemkin: Tech companies will absorb $400M per IPO when markets recover
“When the engine revolves, we will absorb four hundred million again per IPO.”
Jason Lemkin Aug 11, 2023 ▶ 58:35 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
20VC Prediction Partly held up
Lemkin: Menlo Ventures will 10x to 15x its investment in Chime
“They said they did the Series B, right? So they did the Series B at 203 hundred. Maybe we can figure it out on the fly. They're going to, this will be a nine. There'll be some dilution. They'll 10 or 15 X their money, right? That'll be a fun returner or more t…”
Jason Lemkin Jun 5, 2025 ▶ 23:36 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
Lemkin: Venture funding and valuations will never return to 2021 peaks
“For founders, you have to understand that will never lead to a return of 2021. Never.”
Jason Lemkin Jan 13, 2023 ▶ 53:11 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
Lemkin: Employees joining a $1B unicorn in 2023 will make nothing
“If as an employee, if you join a company with, in, in 2023 with a valuation over a billion as an employee, you're gonna make nothing. It doesn't matter what it sells for, you're gonna make nothing.”
Jason Lemkin Jan 13, 2023 ▶ 22:52 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
Lemkin: First founder-VC pitch meetings will never happen in person again
“Like the first meetings will never happen in person again, right? Even if you're in San Francisco, you're all in San Francisco, they'll never happen.”
Jason Lemkin Nov 30, 2022 ▶ 1:00:51 Jason Lemkin: Cold Email Tips; Why Only 15% of Founders Listen to their VCs | 20VC #954 · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: OneStream will IPO at $500M revenue growing 34%
“I mean, the new, the next one's one stream, right? They're gonna IPO at five hundred million in revenue, growing 30 some odd percent, 34%.”
Jason Lemkin Jul 24, 2024 ▶ 20:57 Jason Lemkin: Crowdstrike, WTF Happens From Here? Wiz Rejects Google’s $23BN Acquisition Offer|E1181 · 20VC with Harry Stebbings
20VC Prediction Didn’t hold up
Lemkin: SpaceX IPO will be a dud and will not trade up
“I think the IPO nominally will be a dud. I don't think it will trade up dramatically.”
Jason Lemkin Jun 11, 2026 ▶ 6:45 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: A $100 billion startup exit will happen within a year
“The big exits will solve it, right? The whizzes and the, I mean, we thought whizz was big. Now we have cursor. Now I'm going to win the bet of a hundred billion dollar exit in the next year.”
Jason Lemkin Apr 30, 2026 ▶ 1:05:12 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: Elon Musk will force underwriters to meet SpaceX target IPO valuation
“I think Elon, what Elon said Publicly on X, it ain't going to be two trillion. Maybe he'll change his mind. He said two trillion was too high. So whatever his number is, I think he's going to get it on IPO day. He's going to will it into existence. The underwr…”
Jason Lemkin Apr 9, 2026 ▶ 35:54 OpenAI Buys TBPN & Their Management Team Reboot | Mercor Hack & Why Now is the Time for Cyber · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: US government will block Anthropic indefinitely regardless of court rulings
“The government's going to say you're either going to agree to this or we're going to freeze you out of the US economy. And it doesn't matter what a court says. Because they'll come up with another justification. There'll be another one. There'll be a different…”
Jason Lemkin Mar 12, 2026 ▶ 5:55 Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
20VC Prediction Partly held up
Lemkin: Replit V4 will autonomously build software features overnight
“I know on the next release of Replit, not only does it happen because they've built their own set of guard roles, but the agents do it at night. So in the next release of Replit, when you log in the next day, it will have built three to four features for you o…”
Jason Lemkin Feb 19, 2026 ▶ 1:02:48 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: Fortune 500 will actively replace human employees with AI by year-end
“By the end of this year, that, that train is going to be so far out of the station that, that these growth numbers will be jaw dropping because we will decide enterprises will the fortune 500 or global 2000 will decide we are replacing humans with AI.”
Jason Lemkin Feb 19, 2026 ▶ 15:03 Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
SAASTR Prediction Didn’t hold up
Lemkin: Most SDRs and qualifying BDRs will be eliminated by 2026
“And I really think most SDRs will die next year, but the meat, and I know we throw around these terms differently. The BDR that sort of smarmily qualifies you that that's going to die. Like we just, there's no need for that with these tools.”
Jason Lemkin Dec 10, 2025 ▶ 28:59 How to Use AI to Hyper-Customize Go-To-Market at Scale with SaaStr's CEO and Chief AI Officer
20VC Prediction Partly held up
Lemkin: 2026 will mark the end of entry-level sales jobs
“There'll be, this is the year where we will see the end of so many entry-level sales jobs. We still need AEs. We still need people knocking on doors. We do not need two-year-old kids sending emails. Those jobs will disappear.”
Jason Lemkin Jan 8, 2026 ▶ 1:18:01 Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
20VC Prediction Held up
Lemkin: 2026 will see one or two trillion-dollar tech IPOs
“The idea that we will have a trillion dollar IPO next year, maybe two, we might have two trillion dollar IPOs”
Jason Lemkin Dec 22, 2025 ▶ 30:28 Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
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