Rory O'Driscoll
383 statements across 71 episodes · 97 bullish · 136 bearish · 4 people on the record · first statement Nov 28, 2016 by Rory O'Driscoll · said 63 times in 26 episodes since 2017 · across every show →
On the record as a speaker too: Rory O'Driscoll's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by Harry Stebbings (60), Mark Suster (2), Matt Murphy (1)
tap a year for its mentions
2026 23 mentions in 8 episodes 3 per episode
- Aaron Levie: Everyone is Wrong; We'll Have More Developers in 5 Years · 20VC with Harry Stebbings
- Harvey CEO Winston Weinberg: How to Make Mega Deals | Lessons from Rabois, Halligan & Grady · 20VC with Harry Stebbings
- Will Open-Source Threaten Anthropic's Business & Do Margins Matter in a World of AI | Matt Murphy
- a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
- The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
- Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
- The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings
- Insights from Coatue's Growth Investor Lucas Swisher · 20VC with Harry Stebbings
- every mention in 2026, scene by scene →
2025 29 mentions in 12 episodes 2 per episode
- Benchmark's GP, Everett Randle on Why Mega Funds Will Not Produce Good Returns · 20VC with Harry Stebbings
- BVP Partner, Byron Deeter: The Future of Venture - Why Chanel vs Walmart is BS · 20VC with Harry Stebbings
- Bucky Moore @ Lightspeed Venture Partners: Why You Cannot Do VC If You Do Not Do Pre-Seed · 20VC with Harry Stebbings
- Turing CEO Jonathan Siddharth: Who Wins in Data Labelling & Why 99% of Knowledge Work Will Disappear · 20VC with Harry Stebbings
- 20VC: Why 90% of Founders Build Startups Wrong | Why AI Growth Rates are Sustainable & Remote Work is BS and the AI Talent War | Competing with Brett Taylor and Sierra: Who Wins the Customer Service War with Jesse Zhang, Decagon
- 20Product: How AI Changes Product Design | Does the Design Phase Become Irrelevant in a World of Vibe Coding | The Five Pillars of Truly Great Product Design with Carl Rivera, Chief Design Officer at Shopify
- General Catalyst CEO, Hemant Taneja: Lessons Scaling GC to $40BN in AUM · 20VC with Harry Stebbings
- Miles Dieffenbach: Inside Carnegie Mellon’s $4BN Endowment & The Math Behind DPI, TVPI, Illiquidity · 20VC with Harry Stebbings
- 4 more episodes that year, every mention in 2025 →
2020 2 mentions in 1 episode
2017 9 mentions in 5 episodes 2 per episode
- 20VC: What Does It Take To Gain A Late Stage Cheque Today? The Fundamental Mistakes CEOs Make In The Scaling Process & The Importance Of Building The Next S Curve For Founders with Jules Maltz, General Partner @ IVP
- 20VC: The Power Of A Concentrated Seed Portfolio, Why Operational Value Add Models At Seed Do Not Make Sense & Why We Will See A Shakeout Of Growth Stage Investors with Roger Ehrenberg, Founder & Managing Partner @ IA Ventures
- 20VC: The Radical Changes In Public Market Expectations, The Right Way To Assess Valuation & What It Means To Be A Disciplined & Diligent Investor with Randy Glein, Partner @ DFJ Growth
- 20VC: SaaStr's Jason Lemkin on The 3 Things You Want From Your LPs, Why Most VCs Do Not Add Value & Why The Best VCs Know How To Package Startups For The Next Round
- 20VC: DFJ's Josh Stein on Why VCs Must Adapt To Their Founders, The Major Transition Points For Aaron Levie @ Box & Why SaaS Startups Are Growing At A Rate Never Seen Before
- every mention in 2017, scene by scene →
Everything said about Rory O'Driscoll, oldest first
Nov 28, 2016
Nov 28, 2016
Nov 28, 2016
O'Driscoll: Boards should only intervene when a CEO makes a fatal error
“The only time you take preemptive action, and this is the CEO not listening, I'll come back to the board separately, you take preemptive action when it's a fatal error. What I tell my CEOs is, are you making a mistake or a fatal error? If you're making a mista…”
Nov 28, 2016 negative
Nov 28, 2016 negative
Nov 28, 2016
Apr 20, 2020
Great board members focus on granular work and difficult budgets
“The things that really matter are people who turn up, roll up their sleeves, have a point of view, will do the detail work, actually read spreadsheets. And be thoughtful and be one step ahead of the game on things that are harder that people don't like to do, …”
Apr 17, 2025 bearish
Apr 17, 2025 positive
Apr 17, 2025 negative
Apr 17, 2025 neutral
O'Driscoll: Enterprise customers must replace payroll providers facing criminal liability
“If you're relying on them to manage your payroll, to move money on your behalf, you possibly can provide them having some kind of civil liability. But if it trends over into criminal liability, you probably have to find a new payroll provider, right?”
Apr 17, 2025 neutral
O'Driscoll: Scale's portfolio companies bypass VC preferences in acqui-hires
“When I'm on the other side of the table and my late stage companies are trying to buy early stage companies, I do exactly the same thing. I don't give a shit about Jason and his bloody preference. I want to hire those five great engineers. Let's just give them…”
Apr 17, 2025 positive
O'Driscoll: 15-year holding periods yield 8x to 10x venture fund returns
“If you compound at 30, 40% gross, not for eight years, but for 15 years, because you don't give a damn about giving the LPs money back early, you're just going to compound the thing to make money, then you end up with an eight or 10 X fund.”
Apr 17, 2025
Apr 17, 2025
Apr 17, 2025 bearish
O'Driscoll: Capital flows to venture will fall if major IPOs stay delayed
“If on the other hand, if those keep pushing out, then at some point it becomes really hard to have all this money in private illiquid assets when you have pressures on your endowment and all that. And then at that point you would see the money go down.”
Apr 17, 2025
Apr 17, 2025 neutral
O'Driscoll: Venture capital returns will become increasingly bimodal
“Yes, by definition. I think, and for two reasons, and we'll talk about it. One is, each individual deal has more risk in it. And then on top of that, the whole, it's a totally separate thing, the holding periods have elongated, right?”
Apr 17, 2025 bullish
Apr 17, 2025 negative
O'Driscoll: Portfolio construction matters because consecutive bad funds hurt brand-name VCs
“I think it always matters. You know, your people actually lose money as distinct from thinking about losing money, and particularly when they lose money, two funds in a row, even a brand name firm can hit a bump, right?”
Apr 17, 2025 bullish
Apr 17, 2025
O'Driscoll: Tech and investing expertise is not transferable to politics
“I think what it shows is just because you really understand one domain, investing or technology, it doesn't automatically make you understand a totally different domain politics, and I think you're just saying, look, It turns out YQ is not transferable, and yo…”
Apr 17, 2025
Apr 17, 2025 negative
O'Driscoll: Late-stage startups staying private is a massive public policy failure
“And it's a massive public policy failure because what's happened here is this. It is more attractive for companies to stay private and access capital from GPs who are paid two and 20 plus to make those investments than it is for those same companies to go publ…”
Apr 17, 2025
O'Driscoll: Lost a deal by refusing founder equity refresh concessions
“Yeah, I've lost a deal to not doing that, and you're right, I'm going to be sympathetic to the investor now. I've lost a deal to not doing that, because again, it sticks back to my comment, I tend to be perhaps stuck in the, we, it's not war, stuck in the mud …”
Apr 17, 2025 positive
O'Driscoll: Megafunds with forgiving LPs should pursue late-stage investing over seed
“If you have access to capital that's large and forgiving, which is what these mega funds have, then you should play the big balls game. Cause you're exactly right. You don't do it. You have to do less work. If it works great, you make out the same as Jason who…”
Apr 24, 2025 negative
O'Driscoll: AI roll-up models are flawed due to customer misalignment and churn
“I think it's a crappy model. Just for contrast. You really, the bet you're taking is you buy a set of customers that weren't picked by you because they are suited for your product. They were picked by some mom and pop founder as being the 10 best, the 10 custo…”
Apr 24, 2025 positive
O'Driscoll: AI startups achieve immediate hyper-growth unlike traditional SaaS companies
“The SaaS trajectory is lock in, and Jason knows it so well, trouble, trouble, double, double, and that steady thing. The weird thing now is once you lock in, as you say, in 90 days, you go from maybe, to be fair, a year, six months, a year, you go from this co…”
Apr 24, 2025
Apr 24, 2025
Apr 24, 2025 positive
Rory O'Driscoll: Previous SaaS Era Was Golden Age of Predictable Growth
“That's why those 10 years of SaaS was such a good business, because it was predictable, because the input of sales and marketing to the output of revenue was predictable because the revenue was sticky. In retrospect, it was the golden years of just apply capit…”
Apr 24, 2025 negative
Apr 24, 2025
Apr 24, 2025
Apr 24, 2025 neutral
Apr 24, 2025
O'Driscoll: Spinning out allows VCs to ditch poor past track records
“The other wonderful thing about starting a new firm right now that no one will ever say, not only do you ditch your colleagues track record, you also ditch your own, right? You literally go there and go, I was at mega firm from 2016 to 2024. I did some deals. …”
Apr 24, 2025 negative
O'Driscoll: Missing 5X–10X deals in a firm's sweet spot is far worse than missing outliers
“I'm far more worried about missing a five or like a five or a 10 X deal that was in the scale sweet spot of, you know, one to ten million in revenue, series A or B enterprise software. When you miss that, or even worse, when you turn it down, that's when you h…”
May 1, 2025 bearish
O'Driscoll: Every software startup will face an existential crisis before IPO
“My number one fear is That the technology life cycle to obsolescence is now shorter than the holding period of privately held software companies, which means every company at least one time before it gets to go public will have an existential reinvent itself s…”
May 1, 2025
May 1, 2025 negative
May 1, 2025 negative
May 1, 2025 negative
May 1, 2025 negative
O'Driscoll: Series A investors are paying Series A prices for seed risk
“The problem with Series B is if you get it wrong, you end up effectively paying Series B prices for Series A risk. And it's exactly correct now at the A. You're paying Series A prices for seed risk. But the whole point of having to be good at this job is being…”
May 1, 2025 neutral
May 1, 2025 negative
O'Driscoll: Selling known winning portfolio companies escalates investment risk
“What you end up doing, it always amazes me when I end up selling the company that I know really well, where I've been on the board, I have a pretty good sense of what it's doing and I'm six years in, to reinvest at a slightly higher revenue multiple in a compa…”
May 1, 2025 bullish
May 1, 2025 negative
May 8, 2025 positive
O'Driscoll: Doubling late-stage winners beats grinding early ARR growth
“That double from there. So, so much easier than grunting it out from a million to five million in ARR. Jason, because you did it as a CEO to ten million in ARR. Then the shitty year where you only go to 16. Then you re-accelerate a little. Oh my God. And now y…”
May 8, 2025
May 8, 2025 neutral
May 8, 2025 bearish
May 8, 2025 negative
May 8, 2025 negative
May 8, 2025 positive
O'Driscoll: Generative AI doubles customer service automated resolution rates
“In the sense that, you know, we talked to people who said, and I had an investment in this space pre-Gen AI, right, where the resolution rate was roughly 30, 35%. In other words, one in three calls got solved. We did a bunch of references around this space and…”
May 8, 2025
O'Driscoll: Number two market players should accept acquisition offers under squeeze
“Eventually, when you're the number two and you get the heavy squeeze from the adjacent acquirer, it often makes sense to fold because, you know, because otherwise they might buy the number one and then you're done.”
May 8, 2025 positive
May 8, 2025 negative
O'Driscoll: Mega-funds treat Seed and Series A deals as loss leaders
“And the seed and even the series A is a loss leading product. It's like milk at the grocery store. Come on in, buy your cheap milk, but we're going to upsell you all the strawberries you can buy, baby, right? You know, wait till you see the series C and D, rig…”
May 8, 2025 neutral
O'Driscoll: Private equity structurally beats venture capital except for massive outliers
“Almost everything about PE is better in terms of making money than what we do. And the only thing we have in our favor is that every once in a while, maybe once every five years, you find yourself with a 10% ownership in a thing that's already worth billions o…”
May 8, 2025 bearish
O'Driscoll: Klarna's AI adoption will not deliver step-function profit growth
“Take Klarna as the public example. I mean, they talked boldly and they probably did save those people, right? But I think in the end you'll discover it'll have roughly the same profits as other lenders. It'll be marginally more efficient. It won't be a step fu…”
May 8, 2025 bearish
O'Driscoll: Only 200 of 1,000 current unicorns will IPO
“Honestly, I didn't even notice because it's going to be one of five, 600 of these that's going to have to happen. You know, there's somewhere between 800 and a thousand unicorns and a couple of hundred of them are going to get public and the rest of them are g…”
May 15, 2025 bearish
O'Driscoll: Convicted Founders Face a Huge Barrier to Raising Venture Capital
“Once you pass the convicted criminal stage, the bar goes way up and fairly or unfairly, you can argue your toss. You can argue it's brilliant or not, but I think once you've been sentenced to 25 years by a jury of your, you know, a judge and a judge guilty by …”
May 15, 2025 neutral
May 15, 2025 negative
May 15, 2025 neutral
O'Driscoll: Fast Two-Day Deal Timelines Disadvantage Unprepared VCs
“If it's Monday and you're hearing it for the first time and you got to write Wednesday, you're just way behind. Because even if you crank and write the term sheet, You're also going to be up against someone who's met them before in the last round and is ready …”
May 22, 2025 neutral
O'Driscoll: Mega venture funds must win the top 5-6 power-law deals
“What it means is that the bigger your fund, the more imperative it is you have to be in those six deals, which explains why capital is so easy to raise for those companies. It all makes sense. It was great analysis. I'm not sure it points to everybody can do g…”
May 22, 2025 neutral
May 22, 2025 neutral
O'Driscoll: Late-stage ratchets make peak private valuations an illusion
“You didn't, and an interesting lesson for the founder, you didn't raise money at twenty five billion. You thought you raised money at twenty five billion. But in fact, if you go public at 12, you raised money at 12 and you just didn't know it.”
May 22, 2025 positive
May 22, 2025
O'Driscoll: Core AI features will commodify within 3 to 5 years
“You got to pick your wedge AI entry point for that two or three years where there's kind of magic AI premium, but you got to operate on the assumption that three, five years from now, the core thing you do is going to be commodified. And what you got to do is …”
May 22, 2025 negative
O'Driscoll: Death of IPOs severely harms venture capital allocation
“The death of IPOs is just bad news all around for capital allocation, because now as a GP, you're sitting there going, I want to hold this thing forever. My LP would probably like to get some liquidity. If it was public, I'd distribute, and I'd keep mine. They…”
May 22, 2025 bullish
May 22, 2025 bullish
May 22, 2025 bullish
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…”
May 22, 2025 bullish
O'Driscoll: Large software companies will make numerous small AI acquisitions
“There'll be a whole ton of these over the next, you know, two to three years as these large software companies, you know, Listen to Jason telling them they're screwed on this podcast and decide, I don't want to be screwed. I want to be a contender, right? And …”
May 22, 2025
O'Driscoll: Investors should sell late-stage private stock 80% of the time
“Private late stage companies in 2025 are just the same asset class as IPOs in 95 to 2005. The same analysis applies. Most of the companies barely beat their IPO price a year later or ever again, and a small number of companies compound and do amazing, right? S…”
May 22, 2025
O'Driscoll: AI startups face inevitable churn without mutual success metrics
“Step one on all these deals and every AI deal is do you, the vendor, and you, the customer, have a mutually agreed figure of merit on what success looks like that you can both track? If not, at some point, you're going to churn.”
May 29, 2025 neutral
O'Driscoll: Evaluate equity dilution using offer acceptance and attrition rates
“Whenever I'm on a board on a comp committee and we start talking about, oh my God, the dilution is too high or too low. What I always say, I want to see two other pieces of data. I want to see attrition. Are we losing people? And I want to see close rate on of…”
May 29, 2025 neutral
Jun 5, 2025 positive
O'Driscoll: Non-generational Series A investments can still generate meaningful returns
“The overextrapolation of the only three deals make money, so therefore everything else at series A is burning money is just, I mean, it's true in that you prefer to be in Google, but it's not the only way to make money.”
Jun 5, 2025 bearish
O'Driscoll: Value accretion will shift from Salesforce to AI execution tools
“I think, as I've always said, I think Salesforce instances will be there at scale long after I'm dead, but the value accretion will all go to the technology that's helping me do my job, not the technology that's count keeping score on how well my job's been do…”
Jun 5, 2025
Jun 5, 2025 positive
Jun 5, 2025 bearish
O'Driscoll: AI systems of work will displace legacy systems of record
“I think in front of every system of record, there's going to be some system of work that does it, and it'll sit on top of the system of record for now, and if it does a good job, it will gradually displace, make irrelevant, or replace the system of record if t…”
Jun 5, 2025 negative
Jun 5, 2025 positive
Rory O'Driscoll: Price clears all markets for tech IPOs
“Something a friend of mine used to say years ago, and it's always struck me, it's just so true, price clears all markets. In other words, if you're, you know, you can get deal, it's, what we're seeing it now is, you can't get your deal done at 25, which is the…”
Jun 12, 2025 bearish
O'Driscoll: Only top 10-20% of unicorns can execute tender offers
“It's only that last 10 or 20% who have, quote, IPO potential who could get a tender done. And what that says, therefore, is for most, I mean, so the consideration, the equity compensation for a lot of these companies is notional and not accessible, right?”
Jun 12, 2025 neutral
Jun 12, 2025 bearish
Rory O'Driscoll: Late-stage investing will prove harder over decade than 2021
“I also think there's probably been a little bit of a fake signal in 21 because even your okay ones got highly valued. So you probably think it's easier. Late stage looked a lot easier in 21 than it probably will look across a decade.”
Jun 12, 2025
O'Driscoll: Initial startup growth quartile does not predict VC returns
“Very little correlation between great outcomes being top quartile or second quartile. In other words, they're almost as likely, they're growing quickly, but not astonishingly quickly, has just about the same probability of giving you a great outcome as the hyp…”
Jun 12, 2025 neutral
Jun 12, 2025 positive
O'Driscoll: AI software expands market size by capturing labor dollars
“I think AI is the new, new thing, and to some extent, from a economic perspective, the cursor dollars in software development or any other of these things aren't directly taking away from the SAS dollars. I think it's time expansion”
Jun 12, 2025 bullish
O'Driscoll: Stripe will succeed in its IPO regardless of listing structure
“The very biggest, when Stripe finally goes public, they can do whatever they want. They can do a direct listing and not raise any primary capital. They could do the Google type option, and no matter what, it'll all be fine.”
Jun 12, 2025 neutral
O'Driscoll: Only 20% of current unicorns will reach an IPO
“My gut would be, it's roughly, 20% will be good enough to get public in the end, 20% will totally, maybe 25 on each site, just for arbitrariness sake, and then 50% in the middle are meaningful enough to be valuable, but not so meaningful that they'll get publi…”
Jun 19, 2025 bullish
O'Driscoll: Tech companies with $200M to $500M ARR are preparing IPOs
“I think it's much more true for the whole flotilla of companies in that 200 to four or 500 range who have been trying to figure out where to go and can now see some kind of exit. For those folks, everyone is dusting off their plans.”
Jun 19, 2025 negative
O'Driscoll: Scale passed on Gusto after underestimating the founder and market
“I think I underestimated both the founder and the openness of the market to switch and I'll say something else, the willingness of investors to pay up quickly for that, such that it got outside my price range very quickly, right? Stuff happens, you know, and y…”
Jun 19, 2025
Jun 26, 2025 bearish
Jun 26, 2025 bearish
Jun 26, 2025 bearish
Jul 3, 2025
Jul 3, 2025 bearish
O'Driscoll: Private equity will not rescue subscale SaaS companies
“I don't think it's a, hey, every two hundred million dollar so-so infrastructure company with 16% growth is going to get hoovered up at 5.7 times. I think it's much more a thematic. I think this can be relevant in AI. They have a newer product that's growing m…”
Jul 3, 2025 negative
O'Driscoll: VC board members who leave their firm are practically useless
“Cause I'm realistic enough to say that even if I, you know, if you have a venture board member who is an amazing board member, but can no longer speak to the money. Because there's no longer at the vent, at that venture firm, then to a rounding error, they're …”
Jul 3, 2025 bullish
Jul 3, 2025 bullish
O'Driscoll: Subscale SaaS roll-ups will accelerate once sellers accept price drops
“I think you're gonna see a lot of it, right? I think that, you know, you had mentioned, is it Visma, which is the company that's going public in the UK, and we'll come back to that, but the aha prior to that is it's a roll-up of, you know, hundreds, literally …”
Jul 3, 2025 positive
O'Driscoll: Fewer IPO winners stay private longer, yielding $2B+ returns for early VCs
“At the macro level, what's happening here is the fewer, bigger winners, comma, and it's what I always say to people, it's fewer, comma, bigger, comma, winners, right? You're seeing less winners, there's less IPOs, but because they've grown so much longer, they…”
Jul 3, 2025 bearish
Jul 3, 2025 bearish
O'Driscoll: Startup exit valuations will not keep expanding exponentially over the next decade
“I don't think you accept, I don't think just because the outcome here is thirty billion and it used to be one billion, the outcome, you know, 10 years from now is nine hundred billion. I just don't think the math works like that. I think there's been a step fu…”
Jul 10, 2025 negative
Jul 10, 2025 bearish
O'Driscoll: Non-AI tech workers will be phased out within four years
“Two, three, four years from now, you know, you, you're not going to have people who say I'm too busy to use AI. They're going to be long since God, right? You're going to have people who've been automated away, and then you're going to have people who be, who …”
Jul 10, 2025 bearish
Jul 10, 2025 negative
O'Driscoll: Venture capital cannot fit into liquid target-date retail funds
“One thing we know about venture is you can't target your return date, right? If you could, it would be easier. So it's a hard asset to fit into a liquid Individual portfolio, and I think they'll try. I think it'll be hard.”
Jul 10, 2025 neutral
O'Driscoll: Retail PE expansion will add roughly 20% more capital
“This is a category. This is a trend that's going to happen. You know, I don't think it's going to be the same wall of money as, you know, sovereigns or pension funds. It's just another source of capital, another pick a number, 20% more.”
Jul 17, 2025 bearish
Jul 17, 2025 positive
O'Driscoll: Frontier AI training knowledge is spreading beyond elite labs
“And what the aha for me is this with committed clear leadership, which for all his faults, the UN provides and a couple of billion dollars worth of GPU, which see prior comment, the next level down people know how to do this too. The knowledge is disseminating…”
Jul 17, 2025 negative
Jul 17, 2025 bearish
Jul 17, 2025 bearish
O'Driscoll: AI labs will stop releasing open-source models due to economics
“If you're in the quadrant of patriotic and greedy, which let's be frank, most of that quote people are, you ain't going to be releasing any open source models right now, because it's a Value destroyer from an economics perspective. And you are, you have the wh…”
Jul 17, 2025
Jul 17, 2025
O'Driscoll: Post-trial retention will determine enterprise AI success over 24 months
“One of the key tells in the next 24 months on all of these enterprise AI companies is going to be the percentage of people that stick After they've gone through the innovation cycle, after they've gone through that, we got to try AI, and then they'll ask himse…”
Jul 17, 2025 bullish
Jul 24, 2025 neutral
Jul 24, 2025
Jul 24, 2025 negative
Jul 24, 2025 positive
Jul 31, 2025
Aug 7, 2025 bullish
Aug 7, 2025 negative
O'Driscoll: Opportunity funds fail without $20B portfolio mega-winners
“Unless you end up with one of the very few companies that are not just amazing, but are super amazing, where they can be a twenty billion dollar outcome, your ability to deploy lots of capital relative to your early stage fund is actually much smaller than you…”
Aug 7, 2025 bearish
O'Driscoll: Founders Will Ask VCs to Waive Missed Stock-Price Targets
“My prediction is, and again, I'm often disagreed with on this on comp committees, because I've done some of these where I've tried to make them on tangible targets. What will happen when you do the stock price ones is if the company is doing really well, but t…”
Aug 14, 2025
O'Driscoll: Winners in crowded software markets are founders who ship AI fastest
“Which one of them will get the prize? I tell you, it always comes down to the founder who gets it the most, gets it the quickest, and just puts everyone in the room and says, no one's leaving till we're shipping an LLM-enabled version of this, and we're going …”
Aug 14, 2025 bearish
O'Driscoll: The one-person billion-dollar startup is a metaphor, not reality
“If you do, if you're running a company with a billion dollars in revenue, you're probably making some money. You got to file the tax. Maybe you can outsource everything, but you end up just, yeah, someone's got to meet the accountant. Someone's got to review t…”
Aug 14, 2025 neutral
Aug 14, 2025 bearish
O'Driscoll: AI has entered a 10-to-15-year period of incremental progress
“And then you settle into 10 or 15 years of incrementally making it better until you plateau, right? And from a zero to one perspective, that's not as interesting. But we're now in the grind it out, make it better, build a business stage of life, which I think …”
Aug 21, 2025 neutral
O'Driscoll: Enterprise automation requires high ROI across large headcount volumes
“And my learnings have been, it's not enough to be ROI efficient. There's also so many, there's only so many things you can get your head around as the CFO, Or the chief of operations in a year. So you have to have a quantum. You have to be able to not just hav…”
Aug 21, 2025
O'Driscoll: Stated intentions are meaningless when faced with massive payouts
“One of my rules is this. What people say they'll do when faced with a large amount of money is meaningless and bears no relevance either way to what they'll actually do. Predicting who wants to sell their company based on what they say in the abstract is a was…”
Aug 21, 2025 neutral
O'Driscoll: Extended private market stays mathematically guarantee $100B+ VC outcomes
“In a power law world, the longer you let things cook in the private markets, the bigger one or two of the outcomes will be, and things have been cooking in the private market for, I mean, yes, I think SpaceX is almost 20 years old, they've been cooking a long …”
Aug 21, 2025 bearish
O'Driscoll: 33% chance AI demand slows and multiples compress within 24 months
“I can contemplate at least a one in three chance that sometime in the next 12, maybe 24 months, that demand slows down just enough that people penciling stuff out to the sky suddenly realize maybe it will taper down. And at that point, a lot of these multiples…”
Aug 21, 2025
O'Driscoll: Modern tech companies are 15-year marathons requiring private liquidity
“It made sense where it was a four or five year sprint in the mid nineties and you would go public at fifty million in revenue. I don't think it's realistic to have that attitude in a world where you can be 1215 years. So I think this evolution, you know, to al…”
Aug 21, 2025 negative
Aug 21, 2025
O'Driscoll: Standard Series A and B venture loss rates are 30%
“You know, your typical venture loss rate, you know, your 30% of your deals don't work out, and that's kind of where we play A's and B's. It's probably 50% plus in seed. So, you know, and I remember in 2001 and two, the loss rate spiked to 60.”
Aug 21, 2025 bullish
O'Driscoll: Broad venture capital returns depend on more $5B outcomes
“For the venture business to work for us all, you're going to have to see more of these five billion dollar market cap outcomes. Yeah, as you say, the hinge helps. The owners of this world start to take place, and I think it will.”
Aug 21, 2025
O'Driscoll: Secondary liquidity does not reduce output for passionate employees
“I think money brings out what people really are, because it stops you having to do things you don't want to do. So the people who love their work are going to work just as hard or harder, because they'll be able to throw money at all the other little problems …”
Aug 21, 2025 bearish
Aug 28, 2025 neutral
Aug 28, 2025 bullish
Sep 4, 2025 bearish
O'Driscoll: $4T AI infrastructure investment requires impossible $800B annual profit
“Four, let's do four billion dollars. You want a 20% return on equity. You gotta be generating eight hundred billion of profit a year. That's a lot of profit when, you know, Facebook met, all these guys make a couple hundred billion a year, right? So you've got…”
Sep 4, 2025 positive
Sep 4, 2025 negative
Sep 4, 2025 positive
Sep 4, 2025
Sep 11, 2025 negative
O'Driscoll: AI reverse acqui-hires are regulatory shams leaving dead target companies
“We actually, in both of those cases, that's a pure pretense to get the government off of us, right? Everyone knows both of these companies are toast because in the case of Scale AI, in theory, Meta owns 50% of it, and in theory, their business is selling to ev…”
Sep 11, 2025
O'Driscoll: Scale VP Verifies Bank Balances Directly Before Wiring Funds
“About 15 years back, we instituted the very obvious check the cash balance before you wire test. Because another firm had wired money on the basis of a certain balance sheet. And it sounds really obvious, but they will lie to. So every time we do that, now we …”
Sep 11, 2025
Sep 11, 2025 bullish
O'Driscoll: Customer support is the number one application-level AI use case
“Other than coding, which is the InfraPlay, at the app level, I think customer support, customer success is the number one use case for AI, because it's just so obvious. You have lots of people answering phone calls, answering emails. You can do it all with AI.…”
Sep 11, 2025
O'Driscoll: Every venture investment comes down to three sequential questions
“My mental model is always, we say this internally, is there a category that can support a big winner? Are these guys going to be one of the winners in the category? And are you getting paid for the risk? You could argue that's the kind of sequence of questions…”
Sep 18, 2025 negative
Sep 18, 2025 positive
Sep 18, 2025 neutral
O'Driscoll: AI providers must continuously increase CapEx to win
“Which goes to explain the urgency around CapEx for these companies, because their belief, and so far it's been correct, is that the only way to quote, if you're competing with Cloud Code, all you know is the only way to outperform is more reinforcement learnin…”
Sep 18, 2025 negative
Sep 18, 2025 bearish
O'Driscoll: Pricing houses is harder than cars because margins lie in local nuance
“It's easier to price a car than a house, right? The nuance you have to get right I would wonder, prove me wrong. You can get within seven, eight, nine percent pretty accurately on comps, but it's the little shit that when you walk around the house, oh, they ha…”
Sep 25, 2025 positive
Sep 25, 2025 bullish
Sep 25, 2025
Sep 25, 2025 bullish
O'Driscoll: Startups achieving 'triple, triple, double, double' still get funded
“I think that whole meme is a little overdone, right? The whole, oh, three, three, two, two, double, it's not good enough... And I think that if you really have clarity on that kind of traction, especially at any, you know, and some reasonable scale, right? I t…”
Sep 25, 2025
O'Driscoll: Focus on 18-24 month follow-on rounds, not 5-year returns
“It's far more useful to say to yourself, what does this, cause you don't have visibility on five years, except at a macro level. But what you can say is what's this company going to do in 18 to 24 months? And do I believe it can raise a follow on round at a st…”
Sep 25, 2025 neutral
Sep 25, 2025 negative
Sep 25, 2025 bearish
Sep 25, 2025 neutral
Sep 25, 2025
O'Driscoll: Startups shouldn't delay IPOs just to reach peak private valuations
“I don't think you should stay private just to earn your way back into twenty billion dollars. I think you can go public and then I think it will boil down to, you know, you might go public and either the stock gets converted or as we've discussed, the preferen…”
Sep 25, 2025 neutral
Rory O'Driscoll: Notion would price at $4B-$8B in an IPO today
“A 30% grower, I mean, Netscope and Navan, and well, Netscope has priced already, you know, it's seven, eight, nine times NTM, so something like that, four or five billion, maybe more if they afford growth rate is a little better, or if I'm underestimating the …”
Oct 2, 2025 bullish
O'Driscoll: Fivetran acquiring dbt is a smart combo that reaches IPO scale
“And that's why I think this deal felt to me from a distance, like I'm not the infrastructure guy at scale, but it felt to me from a distance like that's a damn smart, obvious combo. You know, that'll be a good, that, that will get critical mass. I mean, you wo…”
Oct 2, 2025 neutral
O'Driscoll: VCs must merge unicorns to clear 30-year IPO backlog
“But at a zoom out level, this is the kind of thing that simply has to happen over and over again In everyone's venture portfolio because we have six, 700 unicorns. We've processed five, 15 out the IPO gate year to date, so 20 for the year. That implies we got …”
Oct 2, 2025 positive
O'Driscoll: 8% of an IPO-bound company beats 20% of a non-public startup
“Yeah, 20% of something that's not going public is not nearly as interesting as 20, as eight percent of something that is going public, right? And if you believe that it's not a continuum of value, you know, a sliding scale of value, but rather it's a, it's lik…”
Oct 2, 2025 positive
Oct 2, 2025 positive
O'Driscoll: Corporate political neutrality is proven strategy after political activism failed
“There's a distinction subtle between bringing politics to work and not having that, which I think has been validated as the correct strategy. And I think that's almost, I won't say fully a given now, but I think that would be a pretty consensus because everyon…”
Oct 2, 2025 positive
Oct 2, 2025 bearish
Oct 2, 2025 negative
Oct 2, 2025 bearish
O'Driscoll: Meta's AI bet will mirror VR flop, not Instagram success
“If there was a Calci bet, and maybe I should check it that, you know, some version of this AI strategy will not produce meaningful revenue despite a twenty billion dollar burn and will look more like meta VR and less like Instagram and WhatsApp, two of the mos…”
Oct 2, 2025 negative
O'Driscoll: AI startups risk constantly losing product-market fit as models evolve
“Product market fit When you locked into it in SaaS land, you just didn't unlock for 10 years. Whereas here, you can lock in and out of product market fate as the models change, as things, approaches become, and you look back on the product a year ago and you g…”
Oct 9, 2025
Oct 9, 2025
Oct 9, 2025 negative
O'Driscoll: Asking founders if they'd sell for $500M is meaningless
“I think it's a stupid question on its face, on, on multiple dimensions. Let me give you just two ways in which it's a stupid question. The first thing is, and I said this before, people's opinion on what they'll do if they're offered five hundred million dolla…”
Oct 9, 2025 positive
O'Driscoll: Founders in competitive markets should accept aggressive funding offers
“Pragmatically in this market, I think you err on the side. If you have something that's working, And you, even if you don't know where you're going to put the money, if it's on attractive terms, you probably err on the side of taking it. Because if it, if you'…”
Oct 9, 2025 neutral
Oct 9, 2025 negative
O'Driscoll: Professional CEOs cannot replace founders to find product-market fit
“If on the other hand, you don't have product market fit, the founder's not working out and you think you're going to hire someone to get the product market fit, you're deluding yourself. Don't spend a second because it's just too hard and too unlikely. You kno…”
Oct 9, 2025 neutral
O'Driscoll: University endowment VC stake sell-offs will tail off
“So I think for those guys, it's not going to be the new normal in the sense of you're not going to be doing this because it's not going to persist for a long time because by definition, if you're selling a lot of venture assets, you're probably not going to bu…”
Oct 16, 2025 neutral
O'Driscoll: Compressed Timelines Force Choice Between Uncertainty or $2B Valuations
“The time period from we haven't launched yet to, oh my God, it's so obvious has, as Jason said, compressed to the point where it's just, you know, That sweet spot is vanishingly small, and therefore you're left with the choice of do you invest into acute uncer…”
Oct 16, 2025 neutral
O'Driscoll: Target ARR for Tech IPOs Has Doubled to $400M
“We've moved from a world where an exit is two hundred million in ARR to a world where an exit is four hundred million in ARR at an IPO, right? So you're just doing your thing here, but way over there. At the finish line has receded another two or three years, …”
Oct 16, 2025 bearish
O'Driscoll: AI Expansion Will Be Constrained by Economic Returns
“So if anything's going to constrain this, it's going to be economics. And my big picture model here is, you know, you've got the technical trends and then you've got, you know, the economic trends. And the real, the question is, Will it get the return? I mean,…”
Oct 16, 2025 neutral
Oct 23, 2025 negative
Oct 23, 2025 bearish
O'Driscoll: Extrapolating Short-Term Growth Breaks Standard SaaS Investment Models
“If you take these growth rates and extrapolate them for the next four or five years, you could be catastrophic with your mental model of SAS. You know, slight deacceleration every year. You could be catastrophically wrong on growth.”
Oct 23, 2025 bearish
O'Driscoll: Current VC market is as tough as it has ever been
“It was a great time in 2010 1015. It was tough in 21. Frankly, it feels tough today, as tough as it's ever been, because the good news is stuff is working, but there's a lot of variance, a huge amount of capital, and it feels a tough, you're way out there on t…”
Oct 23, 2025
Oct 30, 2025 neutral
O'Driscoll: AI and delayed IPOs are the biggest recent VC shifts
“The two biggest changes of the last three to five years have been the advent of what's happening in AI and the transformation of the late stage and IPO marketplace to this ultra, ultra late stage where companies are way beyond the IPO threshold and still priva…”
Oct 30, 2025 neutral
Oct 30, 2025 bullish
Nov 6, 2025
Nov 6, 2025
Nov 6, 2025
O'Driscoll: Large VC Funds Are Expanding Into Revenue Series A and B
“Given the fund size, all the large firms that were, you know, typically C to A are doing all those deals. So the competition set has stiffened, right? You're up against tougher, better firms, and you've got to bring up your A game, right?”
Nov 6, 2025 neutral
O'Driscoll: Mature 30%-growth SaaS companies are valued at 6-7x NTM revenue
“Your operating assumption should be that for mature companies, SaaS transaction type, whatever, right? It's not just SaaS. It can also be non-recurring revenue companies with decent margin profile and 30% growth. We are back to six to seven times NTM, right?”
Nov 6, 2025
O'Driscoll: True VC IPO returns are best measured 18 months post-IPO
“When we used to track exits every year, which we do, we used to track as of IPO, and then we used to call it the locked in value, 18 months later. And our mental model was that when you want to figure out how much money people actually made, look at the market…”
Nov 6, 2025 neutral
O'Driscoll: Sports leagues, not political administrations, will drive prediction market regulation
“Just to make a prediction and which is in theme in keeping with the idea here. I predict that any re-regulation won't happen because of any new administration. I think the real challenge to sports betting like this will actually be the leagues themselves wrest…”
Nov 6, 2025 negative
O'Driscoll: Navan's IPO Proves Bill Gurley's Pricing Critique Is Wrong
“Actually, this actually shows that sometimes Bill Gurley is wrong because his idea is that these IPO share allocations are called free money. You get your IPO. It always goes up and the leaving value on the table. This is an example of an IPO where, you know, …”
Nov 6, 2025 bullish
Rory O'Driscoll: Enterprise software over next decade will shift to agentic AI
“I do at least feel now since ChatGPT that the direction of architectural direction in enterprise B to B for the next 10 years Is pretty much obvious in a given, you know, it's some form of agentic software. I hate that word. It conveys a lot, but some form of …”
Nov 6, 2025 bullish
Nov 6, 2025 bearish
Nov 6, 2025
Nov 13, 2025 bullish
Nov 13, 2025 negative
O'Driscoll: Sharing Startup Data Serially With Select VCs Is a Mistake
“Conversely, if I was on the board of a company where the founder said, hey, I'm meeting with Joe at mega firm. They ask, can we share some data? They're not, you know, they just want to get a sense of it. I would shut that down and I would say, you share with …”
Nov 13, 2025 negative
Nov 13, 2025 neutral
O'Driscoll: Enterprise Defensibility Only Emerges at Scale Post-Consolidation
“The defensibility theorem emerges at scale, right? In other words, if you, I do believe what's true in most enterprise businesses, once you become the anointed winner, once a market coalesces and there's two or three people at that point in time, you know, It'…”
Nov 27, 2025 negative
Nov 27, 2025 neutral
Dec 4, 2025 bullish
O'Driscoll: Wealthfront Will Become a Compounding Machine Like Charles Schwab
“Over the next 10 or 15 years, that generation is going to get rich. They're going to get rich with Wealthfront. They're going to keep their money there. And it's going to be a compounding machine, just like Charlie Schwab was a compounding machine”
Dec 4, 2025 positive
O'Driscoll: Invest in Front-End Apps Over Infrastructure in Risky Categories
“I'll say Lovable. And I'll tell you why. I think Superbase is benefiting by the trend of vibe coding. And Lovable is a bet fundamentally. It's in the front end monetizing on vibe coding. One of two things happens. Either vibe coding is a category or it's not. …”
Dec 4, 2025 positive
Dec 4, 2025 neutral
Dec 4, 2025
O'Driscoll: Public Tech and AI Companies Structurally Suppress Hiring
“But the interesting thing, when I lifted those three categories, the one thing they all have in common is they all don't need people. The big companies can't have people because they gotta be efficient. The model companies don't need people because they just n…”
Dec 4, 2025 neutral
Dec 11, 2025 negative
Dec 11, 2025 neutral
Dec 11, 2025 neutral
Dec 11, 2025
O'Driscoll: AI market rankings established by 2027 will determine 10-year trajectories
“This is one of those moments in time where how you end up ranking by the end of 26, 27 probably, I think, will determine the trajectory for 10 years, and I think the variance, the high fluctuations we're seeing now will steady out.”
Dec 11, 2025
Dec 11, 2025
O'Driscoll: Founders must verify base models cannot easily replicate AI apps
“One of the non-negotiable disciplines before you do it is you should go and try and use the core models to do the same thing. And you should try and build a functional version of that as simply as you can. And if you can get even vaguely close to it, you need …”
Dec 11, 2025
O'Driscoll: Product-market fit in AI is a moving target requiring instant adaptation
“Product market fit is a rolling feast at the moment. And it's a moving target. Which is why if you look at all your good apps companies, one of the things you see is when the new model comes out, they're on it that afternoon. You know, it's pizzas and late at …”
Dec 18, 2025 bullish
O'Driscoll: Founders Fund's SpaceX deal will return $50B–$100B
“There's no doubt in a world where one investment might return 50 to a hundred Billion dollars. Everyone else has to feel just a teeny tiny tad irrelevant compared to that return for founders fund and good on them. It's a 20 year compounder at 50% plus or minus…”
Dec 22, 2025
Dec 22, 2025 bullish
Jan 8, 2026 neutral
O'Driscoll: Young founders are the most ruthless judges of young talent
“The scariest judge of young talent is young talent, right? And I think one of the really interesting things is, I mean, you talk to any of your founders who are 25, they're marked to market on their team and on other people. They know because that's, you know,…”
Jan 8, 2026 bearish
Jan 8, 2026 positive
Jan 8, 2026 bearish
O'Driscoll: Skeptical the Market Can Support Ten Separate AI Research Labs
“It will be interesting to see, can the world support 10? Research labs coming up with 10 different variants of AI, all of which have to build either commercial or consumer businesses. I think on aggregate I'm fairly skeptical, but it's less a quality of, I mea…”
Jan 8, 2026 neutral
O'Driscoll: The employee quit rate is the best metric for labor weakness
“One of the real tells on unemployment is quitting rate. People don't quit their job when they know they won't get another job. And if you look at the quit rate, That's a really good tell that, oh my God, I know where I am is good, and I ain't leaving, right?”
Jan 22, 2026 positive
O'Driscoll: Non-AI SaaS Startups Growing 75%+ at $50M ARR Are Fine
“Like, I think the truth is, if you're going 75 to a hundred percent, you're fine. Stop. You know, like, this idea, like, because if you're going, look, if you're going a hundred percent at 50, you're going to be at a hundred, then your growth decays to 80, you…”
Jan 22, 2026 neutral
Jan 22, 2026 neutral
Jan 22, 2026 neutral
Jan 29, 2026 negative
O'Driscoll: AI startups fighting hyper-funded competitors must differentiate or exit
“If your customers are getting value from your AI agent that they can't get anywhere else, and you can make that value clear. Then you can charge enough to pay for your tokens, and yay you. If you're not getting, if you're not giving value, or if you're locked …”
Jan 29, 2026 negative
Jan 29, 2026 bullish
O'Driscoll: Wealthfront will compound out long term, but lacks short-term liquidity
“I think they will compound out. I actually like the company and have a mental note here to go check on it and see the valuation and maybe buy some, but you, Jason is right. It, it's not going to be a liquidity event in the short term because there's, it's not …”
Jan 29, 2026 positive
Jan 29, 2026 neutral
O'Driscoll: Venture capital has split into two distinct asset classes
“I think venture is actually two asset classes. It's the traditional early stage venture that's existed for 2030 years, and this new late and later stage venture asset class that used to be called small cap growth, and is now it is now privately held.”
Jan 29, 2026 bullish
Jan 29, 2026 bearish
Jan 29, 2026 neutral
O'Driscoll: $3B market cap is the effective cutoff for tech IPO liquidity
“The objective fact is, Three billion plus or minus appears to be the point at which you're, you know, it's easy to go public and it gets a lot easier the more you go up from there, right? Maybe three is a cutoff, right? And when you do something at two and the…”
Jan 29, 2026 bullish
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…”
Jan 29, 2026 neutral
Jan 29, 2026 bearish
O'Driscoll: Excess capital will erode venture capital returns
“I don't think in either case they benefit from excess capital because I do believe that, you know, Martin Biggs, I've said it before, there's no investing business so good that excess capital won't ruin it, right? And I do think that excess capital will make t…”
Jan 29, 2026 bearish
O'Driscoll: Nearly all 2020–2021 venture investments will yield 1x or less
“Because if you think everything in 20, 21 was either priced wrong and makes a one X or early and just totally wrong and makes, you know, less than one X, let's just say, right? Other than a few companies that were the early precursors of AI”
Feb 5, 2026
Feb 5, 2026 bearish
Feb 12, 2026 neutral
O'Driscoll: Median public SaaS growth held at 30% via IPO replacement
“It was 30% for about a decade and a half, but when you went into it, that's because anyone who goes, to your point, Jason, when you go below 10, you get the red card, you're sent off, you're told, you know, you go off. P.E. Land, but they were dropping another…”
Feb 12, 2026 bearish
Feb 19, 2026 bullish
Feb 19, 2026 bullish
Feb 19, 2026 positive
O'Driscoll: AI disruption requires founder knowledge over generic executive skills
“What you don't need in this kind of situation is generic business skills. What you need is massively specific knowledge and skills and courage to make the changes that you know you have to make. And that is where a founder's advantage.”
Feb 19, 2026 bullish
Feb 19, 2026 neutral
O'Driscoll: 80% of accounting software value is independent of AI
“I believe the next generation of accounting software companies, we've looked at them. They're super interesting. They're adding AI, but fundamentally, 80% of the value in an accounting software package is independent of AI. It's just, it's debits and credits a…”
Feb 26, 2026 neutral
Feb 26, 2026 bullish
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…”
Feb 26, 2026 negative
Feb 26, 2026 bearish
O'Driscoll: Rapid AI labor disruption will trigger a short-term recession
“If the disruption happens extraordinarily quickly, And people don't have time to adjust. Then in the short term, you will have some element of structural dislocation that will result in some form of, definitely some form of recession GDP slowdown if those folk…”
Feb 26, 2026 negative
Mar 5, 2026 neutral
Mar 5, 2026 negative
Mar 5, 2026 negative
O'Driscoll: Software code alone will no longer provide a competitive moat
“Software alone will not be a competitive advantage. So there will still be extremely large demand for software, and there as a result of that will be very big software companies, but they will have to do something more than, hey, I wrote a bit of code for this…”
Mar 5, 2026 bullish
Mar 12, 2026 bullish
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.”
Mar 12, 2026 bullish
Mar 12, 2026 neutral
O'Driscoll: US tech companies employ 3.2M people, including 800K developers
“Entire tech industry, excluding tech people employed in non-tech companies. Technology, NAIC classification, 51 tech companies, 3.2000000 people in the United States, of whom roughly 800,000 are software developers, right?”
Mar 12, 2026 neutral
O'Driscoll: AI capex overinvestment is guaranteed by tech giants' game theory
“By definition, if six or seven people articulate that that's the game they're playing and only six or seven people matter in this discussion, then it is almost Tautological to say we're going to over invest because that's what game theory says until such time …”
Mar 12, 2026 negative
Mar 12, 2026 bearish
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…”
Mar 19, 2026 positive
O'Driscoll: $20B contract solidifies Anduril as a primary defense supplier
“They're basically saying, look, We've gone from trying you out in a lot of different areas to saying, okay, dammit, you're the dominant provider of this layer, so why don't we just systematize the contract? It kind of picks them as, it picks them as the clear …”
Mar 19, 2026 bullish
O'Driscoll: Intuit will remain durable against AI over the next five years
“In my lesson, I think Intuit has pretty durability over the next five years, because I think the thing they automate, which is accounting and tax, has some AI impact, but it's not infinitely large, and I think they can adapt to it.”
Mar 19, 2026 negative
O'Driscoll: VCs investing to meet deployment quotas should halve fund sizes
“If you find your logic being reduced to, I've got to get rid of this much money this month, and this entrepreneur is amazing, so I'm not sure about the opportunity, and I don't like the price, but have a goal. If that's your logic, let me give you some advice.…”
Mar 19, 2026 neutral
Mar 19, 2026 bullish
O'Driscoll: Wheeled robots beat humanoid legged robots for industrial automation
“They, you know, the humanoid robotics that we all see, they have these legs, they consume a lot of battery life, they're pretty unstable, and most of the time in factory work or logistics, warehouse work, you don't want someone using, you don't need legs, you …”
Mar 19, 2026 neutral
Mar 19, 2026
O'Driscoll: Boards with functional trust always keep CEOs until successors are found
“You know, we've all been on boards where we've had to do CEO transitions, and no matter what's going on underneath the surface, right, provided you have good relations and you have a reasonable level of trust, you always go for the leave the person in place, f…”
Mar 19, 2026 bearish
O'Driscoll: Adobe faces major AI disruption risk over the next five years
“So I think the disruption risk on those guys versus Intuit is a lot higher. Five years from now, there will be some disruption into, but we'll still be moving money around. We'll still be producing quarterly accounts, and I tell you, we'll still be paying taxe…”
Mar 19, 2026 negative
Mar 26, 2026
Mar 26, 2026 neutral
Mar 26, 2026
O'Driscoll: Series A returns derive from the initial check, not follow-ons
“For that kind of Series A game, the Series A is not, for us, especially for a firm that just has, you know, checks for A's and B's and of this size, it's not an option value on putting a ton of money in later. Most of your value is made on that first check.”
Apr 9, 2026 bullish
O'Driscoll: Mercor will survive its security breach and rebuild customer trust
“And my guess is the likely outcome is You lose a fair amount of revenue. You lose a fair amount of time. You're going to have to spend a ton of money to bolster your defenses, but if you do the right thing, you'll be able to earn your way back slowly and over …”
Apr 9, 2026 neutral
O'Driscoll: Board members are useless without product knowledge and competitive honesty
“You're not a useful board member unless A, you understand what the company does and how it compares to the direct competitors, ideally with hands-on experience of the products. And then B, you find a way without being a jerk, To keep the company honest about w…”
Apr 9, 2026 bearish
O'Driscoll: OpenRouter will not reach $10B valuation without multi-product expansion
“So, do I think OpenRoto will get to ten billion in value on just what they do today? No. And if they just keep doing what they're doing today, no more than the inference guys, no more than the labeling guys, when things slow down, all these businesses will get…”
Apr 9, 2026 bullish
Apr 16, 2026 neutral
Apr 16, 2026 bullish
Apr 16, 2026 bearish
Apr 16, 2026 neutral
Rory O'Driscoll: Scale passed on early Anthropic deal over pricing and doomerism
“What I realized is if I'd met them at the sea, which I didn't, because it was outside our price bracket, but if I'd met them, I would have done exactly what you did, Jess, and I would have listened to the doom warnings, and I said, that's all silly and wrong, …”
Apr 16, 2026 bullish
Apr 16, 2026 neutral
Apr 16, 2026 bearish
O'Driscoll: Cursor loses money despite generating $4M per employee
“Cursor does four million per employee. Salesforce does 700 per 700,000 per employee. Oh, Cursor must be more efficient. Well, it turns out Salesforce has 30% operating margins and Cursor's losing a lot of money. Why? Because they spend a whole ton on tokens, r…”
Apr 16, 2026 bearish
Apr 16, 2026 bearish
Apr 23, 2026
Apr 23, 2026 bullish
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…”
Apr 23, 2026 bullish
Apr 23, 2026 bearish
O'Driscoll: VC price expectations block AI M&A, but valuations will correct
“The biggest rate limiting factor is not their unwillingness to do it, but the prices at which the venture crowd think we're going to get for them has made it hard to make those transactions. It's been my experience that if that's the case, in the end, things t…”
Apr 23, 2026 neutral
Apr 23, 2026 bearish
Apr 23, 2026 bullish
Apr 30, 2026 negative
O'Driscoll: US sports leagues are antitrust-exempt oligopolies with zero accountability
“Europe, the alleged socialist capital of the world, has a far more performance oriented sports culture than America, where it's a nasty little oligopoly. I mean, the NFL and all the American things have been constructed partly because they're the only three bu…”
Apr 30, 2026
Apr 30, 2026 bullish
Apr 30, 2026 bullish
Apr 30, 2026 negative
Apr 30, 2026 neutral
O'Driscoll invests $500 in retail VC product for Anthropic and SpaceX exposure
“I felt this morning, I put the literally the lowest amount possible in the VC product, so I am now an individual investor in Anthropix, SpaceX, and OpenAI, and even as we speak, I'm adding the logos to our website, right?”
May 7, 2026 neutral
May 7, 2026 bullish
May 7, 2026 positive
May 7, 2026 negative
May 7, 2026 bullish
O'Driscoll: Sierra's LLM token spend is likely under 10% of its revenue
“And my guess is their LLM spend is sub-ten percent of revenues. In other words, LLMs are not the dominant portion of the value they deliver. It's the LLM plus the software, plus the whole thing, plus all the domain specific knowledge.”
May 7, 2026 bearish
O'Driscoll: Meta's $150B AI CapEx to boost ad revenue is a mistake
“They've been using this justification For the LLM spend as being, it'll optimize our existing business, and I've always felt that's bullshit, because if it takes a hundred fifty billion in capex to give a 10% lift on a two hundred billion dollar business, it's…”
May 7, 2026 bearish
May 7, 2026 positive
May 7, 2026 bullish
May 14, 2026 neutral
May 21, 2026 bearish
May 21, 2026 negative
May 21, 2026 bearish
O'Driscoll: Passed on seed GPU capacity deal fearing CapEx boom cycle
“I did, to answer the question, Jason, logically, I chickened out. I didn't want to be that marginal capacity three years into the deal, three years into the CapEx boom, but there's a little part of me thinking, Rory, that might be a dumb decision.”
May 21, 2026 neutral
May 21, 2026 neutral
O'Driscoll: Salesforce's $300M Anthropic spend is 4% of developer payroll
“Salesforce spends 5.8 billion dollars a year on engineers, right? It's, so it's roughly four percent of the spend. If you want it per head, they have twenty-k developers out of their total 83 k heads, so it's 15 k per head per year, which is 1.2 k per head per…”
May 21, 2026 neutral
May 28, 2026 neutral
Jun 4, 2026 negative
O'Driscoll: Unpaid Failure Is Statistically the Most Common Startup Outcome
“I had my own startup. It didn't work out. I look back and I worked, you know, seven by 24 for three years and made no money. That sucked. Right. And that's as a reminder, that's the mode of experience in the correct sense of statistics. That's the most single …”
Jun 4, 2026 bearish
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 …”
Jun 4, 2026
Jun 4, 2026 bearish
Jun 4, 2026 neutral
Jun 4, 2026 positive
Rory O'Driscoll: Tech workers will stay employed, but at lower compensation
“The truth is this, people will get jobs. They mightn't get the high step. I mean, it sucks, but the people repurpose from, maybe you won't get another job that pays 400 grand and allows you to work from home three years a week. I think you will get a job, righ…”
Jun 4, 2026
Rory O'Driscoll: Extreme work hours increase output but degrade decision-making judgment
“I find when you're working really intensely and you're stressed and you're kind of caught up in something, the good news is you put in an extra 10 hours of effort. The bad news is you lost your judgment in doing it.”
Jun 4, 2026 negative
Jun 4, 2026 negative
Jun 11, 2026 bullish
Jun 11, 2026 bullish
Jun 11, 2026
O'Driscoll: Larger VC fund sizes require proportionately larger exit valuations
“Fund size dictates the level that, the amount of market cap it takes. It's a Josh Koppelman thing from ages ago, you know, the Venture Arrogance Index, whatever, right? The bigger the fund, the bigger the deal it has to be to make it work.”
Jun 11, 2026
Jun 11, 2026 bullish
Jun 18, 2026 positive
Jun 25, 2026 bearish
O'Driscoll: IT consulting and systems integration are prime targets for AI disruption
“The core business they're in that, you know, 99%, 90% of their revenue is other consulting, and there are few markets more primed for disruption by AI than consulting in general, because it's wide-collar work. It's very, it's already been outsourced. That's wh…”
Jun 25, 2026 negative
O'Driscoll: Anything outsourced to offshore BPO will be replaced by AI
“When you think about what work AI will replace, you know, white collar work, you can say BPO is a good proxy for that because anything a company is willing to outsource to India, they're probably willing to outsource to AI, right?”
Jul 2, 2026 bearish
O'Driscoll: Protecting AI Frontier Models Harms Economy by Raising Intelligence Costs
“Because what you're saying is keep up the price of AI as an input to the rest of the economy by protecting, protecting these foundation models pricing structure so that they can get a trillion dollars in revenue. And the loser, as always is the case with trade…”
Jul 2, 2026 neutral
Jul 2, 2026 negative
Jul 2, 2026 bullish
Jul 2, 2026 bearish
Jul 2, 2026 negative
O'Driscoll: Anthropic Settled Book Copyright Lawsuit Over IP Scraping
“All the foundation models, including Anthropic, were trained on other people's IP. To the point where Antropic recently settled litigation with a whole bunch of copyright holders on books because they had, quote, unquote, unfairly, to use Dario's word, applied…”
Jul 2, 2026 positive
O'Driscoll: Initial startup growth rate only modestly correlates with long-term success
“There is a correlation, but it's modest between initial growth rate and overall outcomes and companies that have grown slowly at the start have been huge at the end. Procore was a slow grower and then became a huge outcome.”
Jul 9, 2026 bearish
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…”
Jul 9, 2026
O'Driscoll: Optimal employee equity timing precedes secondary tender offers
“The whole trick for employees, just like it is for VCs, is to join something that isn't doing a tender offer today, get a healthy grant, and join a company that within a year or two, when you've vested 50, 60% of your thing, starts doing tender offers.”
Jul 9, 2026
Jul 9, 2026 neutral
Jul 9, 2026 negative
Jul 9, 2026 negative
Jul 16, 2026 bearish
O'Driscoll: AI memory chip supercycle will outlast normal cycles before correcting
“I think it'll last a little longer than the typical cycle, but in the end it'll, I mean, at some point it does correct. You're not going to have the memory makers Earning 70%, not net margins, not gross margins, net margins forever.”
Jul 16, 2026 negative
Jul 16, 2026 positive
O'Driscoll: Active CIOs will implement model tiering to control AI spend
“When the pressure on spend is out there, the sentence you said that really resonated with me is every company is going to have an internal tiering. They might all buy it from OpenAI or Anthropic, but every company with a CIO who's half awake It's going to have…”
Jul 16, 2026
O'Driscoll: Modern capital-intensive tech startups get far better terms than historical biotech
“At least a good portion of this technology is now doing capital intensive deals again, and they're doing it on terms that are way more favorable to the entrepreneur than you had seen in the past, and they're doing that for one reason. They have the money, and …”
Jul 23, 2026 neutral
O'Driscoll: Heavy Structure and Excessive Debt Are Worse Than Two-Tranche Rounds
“And I will say they're silly, but they're not horrific. I mean, if you look at that versus other alternatives, like, you know, taking a high price but with a ton of structure, real structure, that's a worse mistake. If you look at it, you know, not raising mon…”
Jul 23, 2026 bearish
O'Driscoll: AI inference providers will become significantly more CapEx-intensive
“If I'm buying data center compute and then effectively selling data center compute with hosted LLM, at some point I'm going to want to own my own data center assets to have more control of my destiny, which means vertically integrating downwards, which also me…”
Jul 23, 2026
Jul 23, 2026 bullish
Jul 23, 2026 negative
Jul 23, 2026
O'Driscoll: OpenAI and Anthropic training data spend exceeds non-Cursor AI app revenues
“There's probably more money being spent on training data for the foundation models, you know, the Mercosurge and that, than pretty much any app company outside of Cursor. In fact, probably the sum of all the apps companies outside of Cursor, right, you know, a…”
Jul 23, 2026 bullish
Jul 23, 2026
O'Driscoll: AI infrastructure spend hits $900B while AI apps struggle past $50B
“Zooming out a million miles, you know, my mental model is, I divide the AI world up into three buckets. It's the making AI, the infrastructure layer, right? And you're right, the spend there is eight, nine hundred billion dollars a year. Then there's the two f…”
Jul 29, 2026 positive
Aug 5, 2026 bearish
Aug 5, 2026 bearish
Aug 7, 2026 bullish
Aug 27, 2026 bearish
O'Driscoll: Defense tech venture returns will suffer from market consolidation
“I think an area where, despite it being amazing for America and important for the world, I think the venture returns of the March might be tough will be defense, not because we don't need all these products, but because I think there's an element of that busin…”
Aug 27, 2026 neutral
Sep 3, 2026 bearish
O'Driscoll: Enterprise buyers like JPMorgan will not 10x software purchase budgets
“One would be, oh, and the world spent 10 times, they continue to buy software at the same price, and they spend 10 times more on software, right? If you believe in that, you believe in the tooth fairy, right? And there will be some increase in that, but it's n…”
Sep 10, 2026 neutral
O'Driscoll: Economic value will replace AGI questions and benchmarks
“We'll know what works because people will use it because people are rational and economic actors, right? And all these questions on AGI and benchmarks will be replaced by the question, is this model the one that makes me the most, you know, that generates the …”
Sep 10, 2026 negative
Sep 10, 2026 positive
O'Driscoll: Holding competing late-stage AI stakes creates no real conflict
“It totally makes sense to be In OpenAI and Antropic at two hundred billion pre each time, you get limited information rights, retroactive information only, and you know, you're just on the cap table, and it's no different than being in two public companies.”