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 12 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
Market risk is the most dangerous VC risk; the market always wins
“I think market risk is the most dangerous risk to underwrite. Even if with the greatest teams, teams can't fight market. Market always wins.”
Enterprise software companies can now reach $10B to $20B valuations
“I don't think so. I think that the word is out. It's become very, very sexy. I think that a number of other great investors are realizing that you can actually build companies worth 10 to twenty billion dollars in the enterprise space.”
$1 trillion of enterprise software market cap is up for grabs
“I think we're in a magical time where the entire enterprise stack, from storage, cloud, networking, through the app tier, CRM, marketing service, etc., I think all of that's up for grabs, driven by a number of really interesting new technologies fueled by clou…”
Enterprise tech was a contrarian VC focus in 2008
“In 2008, they had a strong point of view that enterprise would be one of the largest market opportunities, and this was almost a contrarian point of view back in 2008. Not a lot of people were looking at very closely at enterprise”
VCs should not haggle over valuation for exceptional teams in massive markets
“If it's a team that has shown ability to execute, that has clarity of vision, that has an incredible product or product vision, and can execute in a very, very large market, it's not worth trying to optimize on the edges for valuation.”
Splunk reached a $20B valuation despite early VC doubts about market size
“If you look at a company like Splunk, which is a dominant player in the data space, That was a venture-backed company. That was a company that went public that a lot of people had written off due to questions around market size, and the executive team there is…”
Market timing succeeds by tracking dollar shifts between technology architectures
“And the way I think about it is market timing works in markets where there's dollars shifting from call it one technology stacker or legacy architecture to a new type of architecture. The most recent being cloud. If you can make an argument that cloud is up en…”
Winning enterprise startups must align product design with go-to-market strategy
“What I've learned over time is the best enterprise companies, the winners, are those that marry amazing product design, which is a combination of technology architecture plus product, which translates into UI and UX, and marry those with a great go-to-market d…”
Startups should land $75K enterprise deals and expand them to $5M
“Really, the reason they do that is mid-market customers move faster, but of course, you capture less value, but you can get some velocity and you can get some market signals about product market fit in the mid market. And meanwhile, you're executing on a longe…”
TripActions manages $1B+ in corporate travel, growing 15% to 20% monthly
“They now manage over a billion dollars in corporate travel. They're growing 15 to 20% month over month.”
Series A pre-money valuations grew from $5M-$10M to $20M-$60M
“When I entered the venture market, Series A's were done anywhere between five and ten million dollar pre-money valuation. Now you're seeing them get into 20 to 50 to 60.”
VC feedback loops take five to ten years to evaluate investor judgment
“In the venture capital world, the feedback loop is slow. You can prove that you can win deals, but you, it takes time to really learn whether you're good at winning the right deals. In many cases, it can take five, maybe 10 years to know if your judgment is ri…”