Zachary Bookman

“I think is, is the earlier, the better.”

“I grew up, you know, I had a difficult home life. My mother was severe alcoholic and parents got divorced after kind of years of home war zone.”

“They're raising, Databricks is raising most of that to deliver secondary to employees, including to deal with some tax issues, and I know that's what Stripe did, and Josh, I think, is doing most of these.”

“I pitched Peter Thiel, and I was so green, and I'd just gotten back from Afghanistan, and I literally would go to work in slacks and leather shoes, like a business lawyer-looking type person, and the Founders Fund guys, at least in those days, did not respect …”

“I'm not less committed now. I'm honestly able to drop back and scan the field and throw passes in a way that I wasn't before. You, it's actually a decent way to encourage the entrepreneur to play small ball. For somebody who grew up without a lot, you know, mo…”

“The short answer is yes. Basically all the time. I don't know how I kept going because I felt for years like I destroyed my career. I'd made the worst set of decisions.”

“I took out 49% of my vested equity.”

“So, look, I think that can continue, but no, I don't see how these companies don't go public. I'm sorry, they've raised a ton of money At some point, people need liquidity, and that's gonna come, so I don't know whether it's in 25, 26, or 27. If I'm guessing, …”

“We were, we actually came out of the gate selling about a year in, but we were selling 5000 dollar software, 10,000 dollar software, transparency reporting. It was kind of a political sale. Governments would buy it to show off the data in their 3040 year old E…”

“I scheduled a two-hour board meeting, and the board was opening up, a lot of give and take, big discussion going on, some important issue, so I decided to let it run, and at, you know, maybe it was 10 a.m. To 12 p.m. At 12 p.m., Mark literally just pulls his c…”

“I've changed my mind on up and comers. I spent a lot of time hiring, been there, done that. And I've grown a little tired of it. And I all, I see the value of promoting from within. I see the value of hiring people that are geniuses and want to work like all t…”

“I was probably in the twenties, if I remember correctly, and I was burning cash like a drunken sailor.”

“Snap judgments are very valuable. A lot of people tell you gotta be thoughtful, you gotta be balanced, and look, you do, especially when, as the organization gets larger, but you gotta listen to your stomach and your gut. I often advise our execs or others, wh…”