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.

clear all ✕

why aren't all 9 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

Insight
David Cross: Founders should send pitch decks upfront instead of teasing calls
“For me personally, is an element is like, you send me the deck as the pre-read opening versus get on a call, right, is I say, be proactive. If you really have something that good, and you'll send me the deck right up front, and it's that good, I'm going to wan…”
David Cross Dec 10, 2024 ▶ 16:21 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: Seed VCs and founders should pursue fast $20M-$50M exits over unicorns
“I think there's a ton of opportunities that you think about of smaller companies, that 20 to fifty million dollar is that some people call it the aqua hire, but right, it's like a founder can come in, your founders can come in, in 18 months, take a couple mill…”
David Cross Dec 10, 2024 ▶ 20:21 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Assertion Supported
Cross: No evidence yet of adversaries using AI for complex attacks
“We haven't seen really any, I say evidence, right? Or of cases that are occurring now where that they're using AI to do very complex or compound attacks and surveys. We haven't seen that yet.”
David Cross Dec 10, 2024 ▶ 5:14 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Prediction Held up
Cross: Adversaries will eventually use AI to find zero-days in code
“Is that saying that we're going to use AI to find zero days in source code? We just haven't seen quite the evidence of yet, but we should still be very suspect that it will occur in the future.”
David Cross Dec 10, 2024 ▶ 6:02 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Assertion Supported
Cross: Ransomware is shifting from encryption to data extortion
“Ransomware now is not going so much after encrypting everything. It's more of a great grab the data, breach, pull it out, and then hold it for extortion, right?”
David Cross Dec 10, 2024 ▶ 7:25 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: Founders often get trapped keeping early executives who cannot scale
“You may hire someone at the very start when five people, they're the chief marketing officer, but now you're 200 people. Are they really still ready to be the chief marketing officer for that next stage? And it's hard sometimes as founders, it's hard as early,…”
David Cross Dec 10, 2024 ▶ 15:13 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: Founders who hide data and claim secrecy have zero chance
“If there's no data, red flag, right? Is if you'd say, oh, it's secret. Oh, we're behind the scenes. We know what we're doing, right? Red flag, right? If you can't be open and transparent, open in the kimono, no chance.”
David Cross Dec 10, 2024 ▶ 18:31 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Prediction Held up
Cross: AI-powered targeted spear phishing is occurring and will increase
“AI, is they're collecting data and public and public information to do very targeted spear phishing, right? And email and things like that. And that is occurring. And it's, or we say that it's very clear that AI is helping those attackers in those cases. So I …”
David Cross Dec 10, 2024 ▶ 5:40 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: New venture investors should assume they will lose their capital
“The first, the best piece of advice I think is, I think the best piece of advice I got is that I, when I started from the very beginning, as soon as you get in venture capital, assume you're always going to lose. And it's going to Las Vegas. You put the money …”
David Cross Dec 10, 2024 ▶ 22:39 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
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