The Ledger, every show

“I actually disagree with Fred. I think if CAC and LTV is a focus on a series A deck, I essentially just want to throw the deck out.”

“The vast majority of VCs are mediocre. That's why the asset class generally is poor, and the top funds generally perform quite well.”

“I think the dot-com crash in many ways informed my point of view that more capital is usually not the solution to problems.”

“It's very easy these days to Scale a brand from zero to fifty million by using hyper-targeting on Facebook. It's very hard to take a brand from fifty million to five hundred million in an enduring way, and to create billions in equity value.”

“CAC doesn't gradually go from 20 to 25 to 30. It goes from 21 day to 80 the next, and I think in many cases where you've created a online category leader, the best solution really is to sell it to a offline previous category leader that's looking to maintain t…”

“I look at Chewy's as what Wright looks like, not Bonobo's, right?”

“I think there's the best way to beat Amazon is with heart. I think Amazon doesn't create the emotional connection with a brand that, say, a Chewy's did, or a Zappos did.”

“You can't hire professional managers to really change the focus of a business. My biggest lesson was when you have an incredibly important strategic initiative, the CEO needs to clear everything off their plate and make it happen.”

“Every single Series B that our portfolio companies raise, the question raised is, what's Amazon going to do?”

“You know, my last three core investments still haven't been announced, largely out of fear of competition, both from Amazon.”

“I also have a deep affinity for companies that target middle America versus companies that are focused on the one percent.”

“If there's a unique characteristic across the most successful portfolio companies we have, it's high repeat and a lack of dependence upon paid acquisition for a significant piece of your revenue.”

“The problem with coding bootcamps is it's a one-time purchase. It's not repeated. Customers often search for it in Google, and even if you have the best product, it's hard to make that readily apparent in the consumer's minds.”

“Everything you say to an entrepreneur you work with has to have intent. You can't let your stress, what's in your head, or your mood impact them.”

“So I was lucky enough to be on the board of Zulily. It went zero to a billion in revenue in five years.”

“Physical product companies might be a quarter of what we do.”

“When we looked at it, we saw that almost 30% of millennials attended a music festival in the past 12 months compared to half of that in 2014.”