The Ledger, every show

“If you are so focused on just the data of user acquisitions, MRR growth, whatever, especially at the early stages where it's probably only a million or so in revenue, I think you can just buy into hype too easily and make bad decisions that ignore common sense…”

“Where people run into mistakes is where they might try to do the Uber for locksmiths. To me, that's just a terrible market because you just don't use locksmiths very often.”

“At Jackson Square Ventures, the partners here, we've invested in four unicorn companies, and three of them, Equalogic, DocuSign, and Responsys, they all had bridge rounds.”

“I believe the best way to get returns is to have very high conviction investments, very concentrated investments, and I think that's the way to beat the market and stand out.”

“I actually don't believe the same company can own both. Largely because the workflow is just completely different for commodity level and master level.”

“The frequency of any one of those Types of transactions might be fairly low, but when you span every single category and you can literally buy anything, the frequency is, is very high. And OfferUp has done that in peer-to-peer commerce. Thumbtack has done that…”

“DocuSign was a fascinating story because we had led a round, and then shortly after that, some regulations changed, and basically they lost 25% of their revenue overnight.”

“Meerkat is actually one of my favorite examples, which was skyrocketing in terms of usage, but nothing was sustainable about it, and, you know, they got an investment, and it crashed shortly after that”

“And so I have to fall in love with the team first, then with the product and the service, and then the data has to back it up.”

“I don't think there's an opportunity to build a master transcription marketplace because there's just not enough of a difference in quality between what we do as the commodity and what a master could do.”

“Somebody comes into your marketplace and spends a thousand dollars one time, and then they're gone. Or somebody comes in, spends 10 dollars a hundred times with a hundred different providers. That is much more valuable because you've got so much more data and …”

“That's actually an important test I look at for every investment is, hey, do users outgrow the service?”

“If people can switch too easily back and forth, you just don't really have that defensibility yet. And you're not building that boat. You know, I think you really need people to completely move all their behavior to your marketplace, and that's when you can wi…”

“Yeah, it's a big challenge for them. You know, I've certainly heard that Lyft is gaining market share, and that is a big problem for them, that almost, you walk around San Francisco, and every car has two stickers on it, One Uber and one Lyft. And so, it's rea…”

“I think one of the strongest ways is to find some sort of aggregator. So find an aggregator of demand or an aggregator of supply to kind of solve one side of the marketplace for you.”