The Ledger

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why aren't all 138 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 36 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Prediction Open · timeframe Sep 2031
Stebbings predicts Meta's stock price would rise if Mark Zuckerberg departed
“If Zuck expired, Meta's stock price would increase.”
Harry Stebbings Sep 5, 2026 ▶ 59:02 How to Build Your Own Data Center & Why Every Startup Should Do It
Prediction Not checkable as stated
Stebbings: Sam Altman and Dario Amodei will successfully lobby for AI restrictions
“I just think Sam Altman is someone who I would never, ever bet against, and I think he's the best politician in the world, and I think when he says something, he says it with intent, and when he says we should give five percent away to the administration, he's…”
Harry Stebbings Aug 2, 2026 ▶ 19:23 Arena CEO: There Will be a $100BN US Open-Source Model & Data is a Trillion Dollar Market
Prediction Not checkable as stated
Sub-$100M boutique seed funds will be the worst-performing VC category
“I think one of the worst performing groups in terms of venture in this vintage will actually be the small boutique seed funds, which is what every single LP that you speak to today, Matt, wants. Every LP. This is the funniest thing. Every LP wants San Francisc…”
Harry Stebbings Jul 27, 2026 ▶ 37:43 Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
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 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 Not checkable as stated
Stebbings: Cursor could lose half its revenue this year to Claude Code
“I think there's a chance that Cursor loses half of their revenue this year with the cannibalization of them by claw code.”
Harry Stebbings Feb 9, 2026 ▶ 11:26 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Tech leaders face unprecedented demonization by 2026 over AI job losses
“I think another prediction of mine for 2026 is I think we're going to see like the demonization of tech and tech leaders like never before, as you see the first real instantiation of job losses and job displacement in, in large parts of the economy, like in lo…”
Harry Stebbings Jan 16, 2026 ▶ 34:54 20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman
Prediction Open · timeframe Sep 2026
Stebbings: AI agents will replace junior marketers and SDRs within 12 months
“Most 25, twenty-six-year-old marketing managers or SDRs, I'm sorry to say it, they're not brilliant. They do not love the craft. They are not better than a phenomenal agent will be in the next 12 months. They will be replaced.”
Harry Stebbings Sep 1, 2025 ▶ 25:53 Cohere Founder, Nick Frosst: How To Compete with OpenAI & Anthropic, and Sam Altman’s AI Disservice · 20VC with Harry Stebbings
Prediction Held up
David protein bars will hit $100M revenue in first year
“And then with David, he's raised eighty-five million dollars from Green Oaks, Peter Atiyah, Andrew Huberman, and in their first year alone, they're gonna do a hundred million dollars in revenue.”
Harry Stebbings Aug 8, 2025 ▶ 0:42 20VC: The $BN Greenoaks Backed Protein Bar | Hitting $100M Revenues in David's First Year: Lessons & Mistakes | $0 to $600M: The Untold RXBAR Story | Product-Market-Fit, Pricing, Branding: What Every Founder Gets Wrong Today with Peter Rahal
Prediction Not checkable as stated
Stebbings: Multi-stage mega-funds will dominate venture capital over next decade
“I think multi-stage win The next 10 years.”
Harry Stebbings May 8, 2025 ▶ 11:46 Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2030
Stebbings: Venture investors will not make money from LLMs
“I don't think any venture investors are going to make money from LLMs.”
Harry Stebbings Apr 18, 2025 ▶ 23:02 20VC: Foundation Models: Who Wins & Who Loses | How Economies and Labour Markets Need to Change in a World of AI | China vs the US in an AI Race: What You Need to Know | Rich Socher, Founder @ You.com
Prediction Open · timeframe Apr 2028
Stebbings: Safe Superintelligence is guaranteed to cover its liquidation preference
“With a LickPref, there is zero chance this does not get bought for at least LickPref.”
Harry Stebbings Apr 17, 2025 ▶ 1:11:56 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Most IPO-eligible companies will refrain from going public within five years
“I do not think in five years the majority of companies that could go public will go public. I think being public will be an unfortunate consequence of scale.”
Harry Stebbings Mar 26, 2025 ▶ 18:42 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Prediction Held up
Stebbings: 2021 Venture Vintage Will Show Poor Returns Amid Inflated Valuations
“I'm pretty worried for venture as an asset class. I think 21 will be some pretty bad numbers and a really shitty vintage, and I think people are artificially keeping numbers high, and I don't think LPs have quite the understanding of how bad it is.”
Harry Stebbings Dec 6, 2024 ▶ 49:49 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Most 2020-2021 vintage VC funds will fail to return 1x
“I don't think many of the 20, 21 vintage funds will return one X.”
Harry Stebbings Oct 25, 2024 ▶ 38:01 Mark Goldberg: Why Politics is Rife & Decision-Making is Broken in Large VCs | E1219 · 20VC with Harry Stebbings
Prediction Open · timeframe Sep 2029
Stebbings: Multi-stage entry prices will cut seed fund returns in half
“I actually think that they've come in with such efficiency that actually they've made it so much harder for the existing pure seed players. They've increased price. They've increased supply. I think you will see returns significantly denigrate. We all saw five…”
Harry Stebbings Sep 6, 2024 ▶ 13:42 Nicholas Chirls: Why Big VCs Ruin Startups, VC is a Ponzi Scheme Today & Most VCs are Bankers |E1198 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Capital gains tax hikes will destroy UK venture capital
“We're going to see cap gains go up incredibly, and everyone's going to leave. And that will be the end of UK venture P hedge funds. It will be disastrous.”
Harry Stebbings Aug 12, 2024 ▶ 1:06:37 Shaun Maguire: Why Iran is the World's Greatest Evil & Trump is the Only Hope for Peace | E1189 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: AI Will Cause The Complete Destruction Of Outbound Sales
“I think AI will actually destroy outbound in many cases, because it will just create infinite supply of messages, or infinite supply of whatever channel that is, and so I think you actually see the complete removal of it.”
Harry Stebbings Apr 24, 2024 ▶ 44:50 Rujul Zaparde: Why Hiring Inexperienced People is Better | E1144 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Software VCs will get burned investing in hard tech
“Having software investors invest in hard tech is a very different game. It is like you wouldn't have your sales team Write code. And it's the same thing. It's a very different mindset. So I think a lot of people will get burnt there”
Harry Stebbings Mar 20, 2024 ▶ 55:55 Jean-Michel Lemieux: Three Product Decisions Every Team Needs to Make | E1129 · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2028
Gap Between TVPI and DPI Will Be Largest in Venture History
“The chasm between TVPI and DPI will be the biggest in venture history.”
Harry Stebbings Oct 20, 2023 ▶ 10:50 20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open
Prediction Not checkable as stated
99% of Money Invested in AI Startups Will Go to Zero
“However, 99% of the money invested into AI startups today will go to zero.”
Harry Stebbings Oct 20, 2023 ▶ 23:24 20VC: NEW FORMAT: Harry Stebbings on Why Seed Pricing is as High as Ever, Why Series A is the Best Place to Invest Today, Why Growth Founders Need to Reshape Expectations, Why M&A Windows Remain Shut and When Will IPO Windows Crack Open
Prediction Didn’t hold up
Stebbings: Threads will stall at 5M DAU while Twitter grows
“I would say threads does not work. Maybe it teases along at five million DAU with hardcore small numbers. And I would say Twitter has modest growth to Two 75, 300 with election spikes.”
Harry Stebbings Aug 16, 2023 ▶ 1:03:47 Brian Balfour: Startup Growth Secrets from HubSpot; Distribution Stratagies; Impact of AI | E1049 · 20VC with Harry Stebbings
Prediction Open · timeframe May 2028
Stebbings: $2 billion venture funds will fail to hit 3x returns
“Trust me, you ain't shooting three X on that two billion dollar fund.”
Harry Stebbings May 22, 2023 ▶ 1:01:32 Nico Wittenborn: Consumer Subscription Apps; Using Evolutionary Biology to Invest; Solo GP's | E1017 · 20VC with Harry Stebbings
Prediction Didn’t hold up
Stebbings: 97% of Capital Invested in Uber Will Not Return 1x
“97% of the money that's gone into Uber will not return one X, just given the quantum of money.”
Harry Stebbings Jan 24, 2023 ▶ 12:00 The Ultimate Guide for Building a Two-Sided Marketplace | a16z's Jeff Jordan · 20VC with Harry Stebbings
Prediction Didn’t hold up
Harry Stebbings predicts traditional VC round ownership will drop to 7.5%
“The days where they could take 15% are gone. It will be a new generation where they take seven and a half percent. Bluntly, alongside people like me and you taking seven and a half percent.”
Harry Stebbings Mar 1, 2022 ▶ 15:34 How I Built a Twitter Audience of 500K+ in 18 Months | Sahil Bloom Full Interview · 20VC with Harry Stebbings
Prediction Held up
Harry Stebbings predicts the quick commerce market will become a graveyard
“I don't think it's going to be like a As many winners as you think it is, I think it's going to be a bit of a graveyard.”
Harry Stebbings Oct 25, 2021 ▶ 32:53 20VC: Deliveroo Founder Will Shu on The IPO This Year, The Rise of Quick Commerce and The Fierce Competition with Uber Eats
Prediction Not checkable as stated
Stebbings: AI data infrastructure companies have a pathway to $300B valuations
“There is a pathway to 203 hundred billion in the data requirements that will be needed.”
Harry Stebbings Aug 29, 2026 ▶ 11:40 Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
Prediction Open · timeframe Aug 2031
Stebbings Predicts Largest AI Data Providers Will Reach $200B
“I think your largest data providers will be two hundred billion dollar companies.”
Harry Stebbings Aug 27, 2026 ▶ 20:14 Anthropic's $30T Assumption & OpenAI Confirms IPO | Why Customer Service & Robotics are Overinflated
Prediction Not checkable as stated
Stebbings: Mega venture platforms will achieve venture returns via massive outcomes
“I think with the outcome expansion that we've seen, cursor at sixty billion trillion dollar companies in a matter of years with OpenAI and Anthropic, you will see Venture returns with mega platform sizes.”
Harry Stebbings Aug 7, 2026 ▶ 37:45 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Prediction Open · timeframe Aug 2031
Stebbings: OpenAI and Anthropic Will Reach $1 Trillion to $2 Trillion Valuations
“Both will be trillion dollar plus, potentially close to two trillion.”
Harry Stebbings Aug 7, 2026 ▶ 1:03:43 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Prediction Not checkable as stated
Stebbings: Fireworks can become a $500 billion company
“If so, fireworks, honestly, It can be a five hundred billion dollar company.”
Harry Stebbings Jul 20, 2026 ▶ 1:08 The Open-Source AI Reality | How Token Costs Will Fall 10X & Usage Will Explode 100X | Lin Qiao
Prediction Not checkable as stated
Stebbings: Consumers will grant full control to AI agents within five years
“I think people will get incredibly comfortable handing over the keys in the same way that we got incredibly comfortable putting our credit cards online using Apple Pay, finding our husband or wife online. And I think that will be de facto in five years.”
Harry Stebbings Jul 6, 2026 ▶ 19:09 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2029
Revolut Will Outvalue Robinhood in Its Next Funding Round
“It's our fintech provider, Revolut, which has stolen the show, and I think on the next round will be considerably more valuable than Robinhood.”
Harry Stebbings Jun 27, 2026 ▶ 43:59 How We Got Fred Wilson, Benchmark and Index to Invest $94M | Why Robinhood's Strategy is Wrong · 20VC with Harry Stebbings
Prediction Open · timeframe Jun 2029
Stebbings: Cognition and Factory will thrive due to model independence
“I respectfully disagree, and that's why I actually think both Cognition and Factory will do very well, because they're model independent”
Harry Stebbings Jun 6, 2026 ▶ 37:17 Inside Legora's Tech Stack: Why Token Maxing is Failing Enterprise Startups | Legora CTO · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Enterprise AI buying frenzy will last only 18 to 24 months
“I think you have to be unwaveringly aggressive now on BD and sales, because I think you have an 18 to 24 month period where CIOs, CISOs are like, hey, we have to have it, we have to have a message for it. That won't last forever.”
Harry Stebbings Apr 11, 2026 ▶ 29:57 ElevenLabs: Building an AI Sales Machine & Why We Set a 20x Sales Quota · 20VC with Harry Stebbings
Prediction Open · timeframe Oct 2026
Stebbings: OpenAI will IPO in October 2026 at $1.5 trillion valuation
“I'm going to say October and I'm going to say it's going to go out at 1.5 trillion.”
Harry Stebbings Mar 5, 2026 ▶ 31:04 Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings
Prediction Open · timeframe Feb 2029
Stebbings: IT consultants will out-earn foundation models in short-term revenue
“I think they will be more revenue generative than the foundation model companies in the next two to three years, as they often are in early stages of kind of cycles.”
Harry Stebbings Feb 12, 2026 ▶ 7:53 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Prediction Open · timeframe Dec 2026
Stebbings: Most knowledge workers will use 24/7 background AI inference by 2026
“I think one thing that we're going to see in 2026 that no one's talking about is 24 seven inference that everyone is going to have inference running all the time, not just on input into chat GPT, but consistently for the majority of people, especially in knowl…”
Harry Stebbings Jan 16, 2026 ▶ 32:14 20Product: Is the Design Phase Dead in a World of AI | Has Claude Code Crushed Anthropic Already | What Roles of a PM Are Less and More Important with AI | How the Best Product Leaders Tell Stories with Noam Lovinsky, CPO @ Superhuman
Prediction Not checkable as stated
Stebbings: Legacy incumbents face a 10-20 year decline from slow AI adoption
“We will be on a 10 to 20 year decline of incumbents who are unable and unwilling to adopt new tools because of data, because of permissioning, because of internal buying processes.”
Harry Stebbings Dec 1, 2025 ▶ 18:27 Turing CEO Jonathan Siddharth: Who Wins in Data Labelling & Why 99% of Knowledge Work Will Disappear · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: VC Winners Will Be Mega-Platforms or Specialized Boutiques
“To me, I think it's like a specialization in leadership that's kind of correlated to actually the winners and losers in venture in the next 10 years, and I think the winners are Walmart, which is your mega platforms, it's your Thrive, it's your Lightspeed, it'…”
Harry Stebbings Nov 13, 2025 ▶ 4:59 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Prediction Held up
Stebbings: Anthropic Projects Reaching $70B in ARR by 2028
“Anthropic projects seventy billion in ARR by 2028.”
Harry Stebbings Nov 13, 2025 ▶ 13:36 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Top mega-fund partners will make over $1B in distributions
“Well, I think if you are one of the top one to three carry participants in one of the large mega platforms, be it Andreessen, be it Thrive, be it GC, I would argue that you will have more than that in distributions in the next few decades.”
Harry Stebbings Oct 23, 2025 ▶ 4:47 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Prediction Held up
Stebbings: OpenAI will top $800B valuation driven by new products
“I'll take the contrarian on you there and say that because of GPT-V and because of Kodak's being two very significant breakthroughs, they'll have enough, plus Johnny Ive coming out with something, a first product, the three combined will be enough to get enoug…”
Harry Stebbings Jul 31, 2025 ▶ 1:19:30 Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Heavy AI equity dilution will damage venture returns
“That's partly why this wave I think will be highly damaging to venture returns because the employee stock based comp dilution is going to be so significant and so much more significant than in prior generations of venture.”
Harry Stebbings Jul 10, 2025 ▶ 18:59 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Prediction Held up
Stebbings: Revolut will likely reach a $100B to $150B valuation
“I think everyone is realizing now that Revolut will quite likely be at least a hundred billion dollar company and likely a hundred and fifty billion.”
Harry Stebbings Jun 5, 2025 ▶ 28:21 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Prediction Open · timeframe May 2030
Stebbings: OpenAI Will Reach a $1.5T to $2T Valuation
“I am so sure that open AI is going to be a one and a half to two trillion dollar company right now.”
Harry Stebbings May 15, 2025 ▶ 49:20 OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
Prediction Not checkable as stated
Stebbings: Stripe's value and internet GDP will soar via AI entrepreneurs
“I think Stripe will be massively more valuable. In a world that we now enter, because I think there will be so many people who are enabled to create stores, entrepreneurial endeavors, and will inevitably use the default of Stripe as their payments mechanism th…”
Harry Stebbings Mar 14, 2025 ▶ 37:02 20Product: How to Design and Build Products in a World of Agents | Why AI Will Kill Many SaaS Products | What Products Will Thrive and Die in a World of 100M Developers with Matt Biilmann, Co-Founder and CEO @ Netlify
Prediction Open · timeframe Jun 2028
Stebbings predicts Stripe will remain private for another four years
“I think Stripe will still be private in four years time.”
Harry Stebbings Jun 3, 2024 ▶ 52:23 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
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