What-if
Gilbert: Webvan would have beaten Instacart if it had modern capital
“If there was the capital available to those startups, then the way there is today, then perhaps I wouldn't be ordering from Instacart yesterday. I'd be ordering from web van because they would have been able to stay the course because at scale, that business m…”
Insight
Gilbert: Early-stage venture is hedged speculation, not actual investing
“I don't really think early stage investing is investing. I think it's hedged speculation, and the hedge is partnering with the very best entrepreneur you possibly can find after years and years of relationship building and going into interesting markets where …”
Opinion
Gilbert: Masayoshi Son realized private late-stage startups genuinely wanted billions
“That was a brilliant insight at the time that these people really do want billions of dollars while they're still private, and there's effective ways to deploy that.”
Assertion Not checkable as stated
Gilbert: Top young developers are building Web3 apps, not mobile apps
“The big thing to pay attention to, at least in my opinion, and why I've started really focusing on it as an investment area is every time David and I are interacting with someone in the acquired community who's a builder of some sort, or they're a passionate, …”
Insight
Gilbert: Venture fund scaling follows a four-minute mile dynamic
“It is taken as the canonical wisdom that you couldn't possibly do this strategy, and then when someone does, all other strategies feel really tenuous and obsolete quickly.”
Insight
Gilbert: The internet only rewards massive scale or niche specialization
“There were only two strategies that worked in media and journalism over the last 10 years because of the internet and social media.
There's get huge, like the New York Times and the Washington Post, or there's niche down.
But if you are caught in the middle wh…”
Insight
Gilbert: Mid-sized venture firms decline slowly because downsizing feels unnatural
“If you aren't able to actually go compete with the New York Timeses, the Sequoias, you can't raise that much capital, you can't hire that caliber of partner, whatever it is, it's really hard to downsize and pick a lane when you kind of look around and you're l…”
Insight
Gilbert: Incubate and co-found companies when late-stage venture capital becomes overheated
“If all companies out there are raising money at crazy valuations, and it's crazy competitive to just put commodity capital in, okay, start companies. Play the other side. Be a co-founder.”
Insight
Gilbert: Startup investing is no longer venture capital, just capital
“So I think my one liner on what is it today is it's no longer venture capital. It's just capital. And by that I mean, with very few exceptions, you look at maybe incubation, maybe like true pre-seed, There are public market investors and very wealthy individua…”
Disclosure
Gilbert: I refuse to lead early-stage deals at $100 million valuations
“I would never lead a deal at that. Because even if I go put in three million dollars, I'm going to own three percent of this thing. God willing, it goes well. I basically end up owning the de minimis amount by the time they go public.”
Insight
Gilbert: Low-view YouTube talks by executives contain insights the press misses
“And the other fun hack is there's these criminally Under viewed YouTube videos, which is executives whose names you know and executives whose name you don't know giving industry talks at conferences, and these end up on YouTube because they're giving out publi…”
Assertion Not checkable as stated
Gilbert: Early venture capital had no stages, just $2 million checks
“There was no real notion of early stage venture capital versus late stage venture capital. There was venture capital, and that meant writing a two-ish million dollar check, and hopefully that was enough to get the company profitable so that it could go public.”
Assertion Not checkable as stated
Gilbert: The Acquired podcast has an audience of 160,000 people
“And then, of course, we have acquired, which is a 160,000 person megaphone, which then we can preach to once there is something we want to talk about.”
Disclosure
Gilbert: Acquired began to investigate why large acquisitions succeed
“When I pitched him on the concept for Acquired of, like, hey, you're investing in companies, I'm starting companies, like, it'd be nice to understand When they get acquired for like a lot of money, and those go really well, why?”
