The Ledger
Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.
why aren't all 77 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 2 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
Rajaram: B2B software switching costs will drop to zero within two years
“I think switching costs is less going to go to essentially zero because over the next one or two years, ability to port data, your data as a business or consumer from any ecosystem to another ecosystem is going to be very easy.”
Rajaram: The public market software selloff due to AI is 100% overreaction
“I think this is 100% overreaction because not all software companies are created equal, and we can talk about what the differences are.”
Rajaram: AI will enable pixel-by-pixel cloning of software products
“And then people are going to be able to replicate almost pixel by pixel. The experience you have with one product in a different products, you'll have clones popping up left, right, and center and data portability is going to be easy in that case.”
Rajaram: Scale is no longer a competitive moat for pure software companies
“Software earlier was a scale game where because you had produced a lot of software, it was cheaper for you to produce a lot of the guess what? Now everybody can produce software as cheaply as anybody else.”
Rajaram: Systems of record must commoditize complementary AI products
“And I think that's the way that a net suite or a sales for the system record needs to operate. They have to commoditize a compliment. They can't just wait around for other people to build on top of them.”
Rajaram: Most bolt-on AI products are thin wrappers over OpenAI or Anthropic
“Most bolt on players are not doing it. They're simply using a GPT or anthropic model. And they're basically just adding a thin layer. You have to rebuild the entire experience end to end.”
Rajaram: Long software roadmaps are rendered obsolete every six months by AI
“Model capabilities are improving every six months because if you have too long a product roadmap, you're going around your program and the model comes and just blows it out of the water. So you've got to really understand what the capabilities are of each new …”
Rajaram: Fintech businesses moving money possess strong and defensible moats
“If you're moving money, you're generally in a good place. So anything touches money, We feel there's a very strong moat there, a much more defensible.”
Rajaram: Data and workflow are the only reliable non-fintech software moats
“Data and workflow moats are the two things you're really hanging your hat on as a software investor, because if you're not doing FinTech and then I think it early stage is too hard to know what a distribution moat is unless they have some hack and these hacks …”
Rajaram: AI replaces labor via BPO cuts, attrition, and finally direct layoffs
“The first thing that's happening is businesses are outsourcing to third party BPOs, many of them in India, Philippines, et cetera. That spend is the easiest to cut because now you can offer the same service, higher quality, faster, and 20, 30% cheaper. The sec…”
Rajaram: High-valuation, low-growth startups will become zombies and sell to PE
“A bunch of them are going to become zombie companies, And they're going to try to add AI features as a last resort, not succeed and be sold to PE.”
Rajaram: Seat pricing fails when AI executes work instead of providing access
“Now, the big challenge is seed based pricing, which you alluded to, is it breaks when the product's core value is not about access, but it's about something doing the work on your behalf. So at that point, charging per user doesn't make sense because user isn'…”
Rajaram: Jasper's ARR shot from $1M to $100M before falling to $40M
“I think we saw in the first way of AI, we saw many chat GPT, like there was a company called Jasper, not to pick on them, but they went from one to 40, and then they came back from 40 to 10 or something like, or maybe one to a hundred and a hundred to 40 withi…”
Rajaram: Moritz's Instacart investment was the top VC bet ever
“I think the best venture capital, I, someone asked me what's the best venture capital bets. I talk about a paradoxical one. I think it's Mike Moritz betting on Instacart. Why? Because he lost three hundred and seventy million on web van less than a decade ago.…”
Rajaram: Benchmark made money on WeWork by investing early
“Even in V work benchmark made money. Genchmark made money at WeWork because they invested early enough.”
Rajaram: You cannot build a Series A fund at $300M–$400M valuations
“Maybe you can do a couple of deals like that, but I don't think you can build a series A fund doing deals at three or four hundred million. Because it's not going to be enough ownership. These, some of these are going to fail, et cetera. But most deals, I thin…”
Rajaram: Startups must avoid competing directly on Google's primary roadmap
“If you're a startup, which is directly in Google's roadmap, like directly, you should not be building it because Google is very good when something is directly in order. They're like a tank. It will just roll over you even slowly, slowly, but it doesn't matter…”
Rajaram: Marathon will not invest in frontier AI labs at billion-dollar valuations
“Not possible. I don't think with our fund it's possible. I think the ownership is just literally the first round for these companies is, like you said, a billion dollars. So I think it's just too high a, the risk reward is just not worth it.”
Rajaram: Mega funds use $15M Series A checks as options
“They've basically gone and they deploy fifteen million dollar checks almost as an option and a lead lead generation for the next run. And the strategy is obviously to have an index at the A of every single good A company and then double down on the ones that t…”
Rajaram: Partner departures leave mega fund startups orphaned
“We see many examples actually in mega funds of partners leaving the fund and the companies orphaned within the mega fund because their partner has left. And now they don't have a single person to advocate for them in any way, shape or form, and they're adrift.”
Rajaram: Pure remote work fails for early-stage startups
“I used to think pure remote would scale for early stage companies if you have the right culture, but I don't think that anymore. I think you've got to be in person at least a few days a week.”
Rajaram ranks Page, Zuckerberg, Dorsey, and Xu as top CEOs
“I would say the best technical CEO, Larry Page, the best growth-centric CEO, Mark Zuckerberg, The best design-centric CEO, Jack Dorsey, and the best physical world operational CEO, the most likely to be Jeff Bezos next, Tony Xu.”
Rajaram has backed more dropouts recently than in the previous 15 years
“I've actually invested in more dropouts as an angel now over the last few months than I have invested in in, in, in, by the rest of the last 15 years I've been investing.”
Rajaram: Software companies must own the full stack and go multi-product
“You cannot be a single product company. Critical products, you've got to really own full stack. It's harder otherwise to be a ten-plus-million-dollar company.”
Rajaram: No amount of distribution will save a company without remarkable products
“So I think I ultimately, my core investing thesis is that if there is not remarkable product, all the go-to marketing distribution in the world will not save you.”
Rajaram: Mark Zuckerberg is the greatest distribution genius in the world
“Mark, I think is Mark Zuckerberg is probably the best. I would say distribution genius in the world.”
Rajaram: Tech companies cannot survive long-term as single-product businesses
“You have to have, you cannot be a single product company. You've got to make sure, and most importantly, your product number two needs to emanate very naturally. It can't be like this completely separate product. It has to be very adjacent product number one.”
Rajaram: Companies must separate profit-generating products from retentive products
“Companies need to be very clear which are the profit pool products and which are the retentive products. If you confuse the two, your teams don't know and they're built for the wrong outcomes.”
Rajaram: State licenses make Coinbase irreplaceable for crypto custody
“Coinbase, when I'm on the board, is a great example. They have MTLs, money transmission licenses, state by state. There is with the Fini, CN, all of those things. It makes it impossible for a company to use anybody else than Coinbase to custody their crypto be…”
Rajaram: AI cannot replicate DoorDash's liquidity and marketplace density
“AI can vibe code the ability to access restaurants, but it can't vibe code liquidity, courier density, reputation history, all of those things. So marketplace density is a network effect, which is structural.”
Rajaram: Software companies need four of eight possible moats to stay defensible
“Any one of these modes is not enough. But what you want to do is you want to take a company and score it across them. Maybe you assign one point to each mode they have. And I think anything four or more, you're pretty damn secure. But if you have a two or thre…”
Rajaram: Atlassian possesses at least three core software defensibility moats
“Atlassian has, you could argue they have proprietary data. Now they need to use that data to build products. They have unique proprietary data on all the code out there because it's being checked in. There's a lot of stuff they have, which they need to use for…”
Rajaram: Monday.com has a much weaker defensibility score than Atlassian
“Monday probably has a score of one, I think. They have a workflow mode. I'm not sure if they have the other modes. So you're right. Monday, in theory, has a much weaker score, I guess, than Atlassian on this.”
Rajaram: Shopify will not build a competing product to Klaviyo
“I don't think Shopify will build it. Shopify is an investor, and Shopify, I think, has decided, at least in my opinion, that this is, Shopify has these things called missions, and I think they've decided this is not part of their mission to build this product.…”
Rajaram: Mid-sized VC funds can return $10B vertical SaaS winners
“If you're a 203 104 hundred million dollar fund, you can absolutely create a ten billion dollar company. Because remember, one of the big changes is that vertical SaaS does take over labor.”
Rajaram: Intercom's Fin and Podium reached $100M+ ARR from AI products
“Fin great example podium, another great example, both of them with the new products have gone to a hundred plus million in a couple of years.”
Rajaram: Seat-based pricing will not die due to enterprise predictability needs
“Seat pricing doesn't die. You know why? If you look at Chad GPT Enterprise is priced based on based on seats, because seats provide predictability for enterprise buyers But they don't drive expansion revenue by themselves.”
Rajaram: Smaller venture funds lose by copying $10B mega-funds
“Somebody with a ten billion dollar fund is playing a fundamentally different game than somebody with a four hundred million dollar fund and if you try to play the same game there, you're going to lose.”
Rajaram: Uber expanded margins continuously by altering driver pay economics
“Uber, I have to say, I don't know how, if they have raised price or not, but I know that they have basically changed the economics of how much they pay drivers over time so that their margins have just expanded continuously. And they've also raised prices in d…”
Rajaram: Zuckerberg refused to anonymize Facebook in Japan and won
“I remember when Facebook had to go into Japan, Japanese cultural norms were that all the Japanese social networks back then were incognito. You couldn't, for some reason, maybe saving face or something. You could not share your real name or your photo. So ever…”
Rajaram: Faire seed investment generated a 100x to 200x return
“I, for example, I invested in the seed round affair at Back in the, this is about eight, nine years ago, twenty million, which is very expensive received on that. It was the highest price YC deal at that point. I think it's been a hundred or 200 X for me.”
Rajaram: Series B and growth valuations destroy venture returns
“Now I think the B, I think B plus that's when strides price starts destroying returns. I think by then you got real revenue, real traction. You got to, you can pick a generally good company and still get crushed.”
Rajaram: Most early-stage venture firms focus on MOIC instead of IRR
“One of the things I think most early stage firms get wrong is they just focus on Moik. They don't focus on IRR.”
Rajaram: Passed on Quince at $100M valuation before $10B raise
“Quince recently raised a ten billion. I saw Quince four years ago when it was at a hundred million valuation. And I was like a D to C company. D to C companies are kind of on the downswing. How, how good can this company be? What do you know, so I literally ju…”
Rajaram: Mega fund investors will continue spinning out into smaller funds
“I think we are going to see a more spin out. I do think there is a limit, but I do think you're going to see the, you're going to see these mega funds train again, more waves of investors. And these investors are going to realize that being a mid-level partner…”
Rajaram achieved a 500x to 1,000x return on his Figma angel investment
“Five of, between 500 and a thousand X at the time of IPO, but it has sadly gone down since then.”