The Ledger, every show

“I haven't done a ton in VR because I find it insanely difficult to predict when that market's really going to take off at scale.”

“What I do now, which is, it's not a trick, but I start the work of building the company, like in the second meeting. So instead of sitting back and listening to a pitch and formatted information, it's like, let's map out the organization. Let's think about you…”

“So HubSpot in Boston was famous for not having any titles for the longest time. They're titles externally, because clients care or your executive vice president or whatever, but internally, actually, they refuse to have a structure of titles.”

“And then number two, of course, is Andreessen Horowitz. You're the badass operators who come into venture and say, nobody in venture is a true operator. So we are going to build an operating company to help build startups. And so half or more of the organizati…”

“I'd say I spend half my time telling people what not to do, so they're more efficient at the stuff that actually matters.”

“Dysfunctional boards tend to be reporting boards where there is distrust with the entrepreneur, usually because they don't spend enough time with the company and, or they forgot, they lost the empathy of understanding what the, what journey the company is on a…”

“And did that for about seven years, and then I guess I saw firsthand how the moved, the world of finance moved from hedging risks to arbitraging the shit out of everything.”

“Your core eight to 10 first key hires, especially at the executive level, need to be great. You really just cannot afford to make too many hiring mistakes”

“Deliveroo is the fastest growing startup I've been involved with.”

“The number one reason why seed companies fail is because they hired the wrong co-founders.”

“Your irrational expectations of what you can do in a short amount of time end up costing you the survival of your business.”

“Because some of our best companies, if I look at BitNine, one of the Atlas companies in the That is a phenomenal success story. They almost ran out of money three times”

“The investments that I regret making Are systematically the ones where I didn't spend enough time getting to know the founders. So there's an almost perfect correlation with shit where I wish I hadn't invested, and the fact that I didn't have time to build a r…”

“The difference between being an asshole and being someone who does their job well is you tell them early enough.”

“If you look at Atlas, I probably invested about a hundred million. You know, I think I'm going to end up being three and a half times my money, four times maybe, but it took forever for these numbers to come through.”

“JP Morgan, I think, reported that SMBs in the US have a median working capital of 26 days”

“Excluding nano funds, which aren't tracked, there is something in the region of 1100 or 1200 new funds that have been established in the US over the last 10 or 11 years or so.”

“Well, when I spoke to Will Shue at Deliveroo, there were 20 people in the company. It wasn't as early as what we usually do, but, you know, he had seven term sheets on the table.”

“So one of the great failings for me is when we have to let a founder go, and I hate doing it, and it's only happened twice in my career, and I hope it doesn't happen again.”