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 23 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 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
Sim: 2024 IPOs require cashflow breakeven, 30% growth, and Rule of 40
“If you're gonna go public, I think you've gotta be cashflow breakeven. I think you have to have, you know, 30% plus growth, which is probably what high growth is right now. You've gotta be moving towards a rule of 40 or 50 with slanted more towards growth than…”
Sim: Boldstart pushes down seed round sizes to test founders
“I'll lead you around now if you want three, but not at six. So they come back to us, you know, a few days later and like, you know what? How about four? And the reason I do that Harry is because I want to test them. I want to test them to make sure that they a…”
Sim: Optimal Modern Seed Venture Funds Must Be $150M to $250M
“I think a fund size between one 52 50 for doing this in a highly concentrated position with ownership and doing it in a way that allows you to write bigger checks after the discovery round to help a classic round, you know, raise a little more of an extension …”
Sim: Seed and pre-seed investors take less risk over time
“And then the pre-seed category was created because seed, seed investors weren't taking as much risk. And now the pre-seed investors aren't taking as much risk, which is why I'm saying let's do inception investing.”
Ed Sim: Incubating companies is unscalable unless it is a firm's sole focus
“And by the way, this is not incubating a company. That's not a scalable model. And that's, unless that's all you do.”
Ed Sim: Startups raising $3M-$4M should avoid SAFE notes for priced rounds
“If you're doing a classic round of you're raising three to four million, I like to tell the founder that, hey, you should probably not do a series of safe notes here because you never really know what you own, especially in conversion. You want to actually do …”
Enterprise software markets repeat and rebuild identical tools every 10-15 years
“So that's what happens in enterprise. It's the same shit getting rebuilt every 10 or 15 years in a different way with a different pitch.”
Seed startups relying on analyst reports for market sizing are uninvestable
“If you have an analyst report to kind of show us, then it's probably not worth investing in, you know, at the seed stage.”
Developers increasingly drive enterprise software purchasing decisions bottom-up
“I think developers are increasingly wielding more and more power in the enterprise these days, and it's one of those things where they're, you know, coding or develop, or using a new technology, they'll download it, or they'll try a free version, then they'll …”
Sim: Having 36 months of cash runway does not mean you have a business
“Just because you have 24 or 36 months of cash doesn't mean you have a business.”
Sim: Early VCs need valuation discipline to succeed on $300M to $500M exits
“Cause if early guys will do well, as long as they're not paying 50 to 75 Brie for some of these inception rounds, you know, if they exit a three to 500, but you need more of those to return a fund. So it changes the dynamics of everything where ownership matte…”
Sim: Two-thirds of startup bridge rounds yield positive outcomes
“I'd say probably two thirds work out more positively than negatively, but the ones that work out can be outliers.”
Sim: A startup's exit TAM matters far more than its initial TAM
“It's not the TAM you start with. It's a TAM you exit with.”
Sim: Founders must deliver 10x value narrowly before expanding their platform vision
“You've got to be able to zoom in on the end user, zoom in on how you make their life 10 times better with your product and how you can uniquely solve that problem. So you sell the product, but then you can market the vision to us.”
Sim: Investors should challenge founders during good times and support them during bad
“When things are going really, really well, that's when you challenge the foundries even more. And when things are shitty, that's where you kind of pick them off from the ground and maybe kind of cheer them on a little bit. So I call that my three CH is cheer, …”
Sim: Enterprise AI adoption requires dedicated AI security
“I think that there's no AI in the enterprise without AI security. And I think that's a completely new category now.”
Sim: Inception rounds split into discovery, classic, and Megatron jumbo tiers
“The point is the three rounds are, there's a discovery round, which my opinion is less than two million. So it's usually like maybe a first time founder exploring a new market. It would graduate to the next round, which would be a classic. And a classic round,…”
Sim: Repeat founders avoid pre-seed rounds to prevent extra equity dilution
“A lot of times founders who are second and third time founders don't want to even be called to have a pre-seed round because it presupposes you need a seed round. And what does that mean to you, Harry? It means that if you have a pre-seed round and you have a …”
Sim: Startups solving hard technical problems appear slow before hitting rapid growth
“Some of the hardest problems to solve will take longer and it'll look like your slowest plotting company to start with. But in the long run, to your point, these things are the ones that can actually go, you know, hit the J curve pretty quickly.”
Startups taking on incumbents must build baseline table-stakes features first
“No matter how, how, how big of a vision you have, you still need at least the table stakes of, you know, check box of four things that they may need before they even believe in your vision. So it takes longer.”
Ed Sim: Underwrite tech startups assuming 10x to 14x forward multiples
“So you've got to build your business and your investment strategy and your ownership strategy around looking at a world where we get 10 to 14 for the best companies forward next year's numbers.”
Enterprise founders achieve repeatable success easier than consumer entrepreneurs
“And in consumer, I think it's harder to be a repeat consumer entrepreneur, right? Because you typically start an app, you know, let's say, and launch that thing, and then you try to start another one, but you can't bring that same customer base over. You've go…”
Modern SaaS scales via marketing and inside sales, not field reps
“Instead of building a huge regional direct sales force, you know, Today you may bring on a marketing person to be a lead generation machine, right? And then you have built an inside sales force to kind of, you know, follow up on those leads, and then you bring…”