YouSaid · the spoken record

Zac Bookman

lines on the record: 81
first: 2024-12-06
most recent: 2024-12-06
sittings or episodes: 1
sources: podcast

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“I'm talking about the fundraise innovation fund, which is democratizing venture capital as a public venture fund. For example, most of the AI revolution is being built and funded in the private markets. Companies like OpenAI, Anthropic, Databricks, these are incredible multi-billion dollar companies, but they're inaccessible to 99% of investors until they go public. Well, those days are finally over. Visit fundrise.com forward slash 20 VC to check out the Fundraise Innovation Fund's impressive 150 million dollar portfolio for yourself. Carefully consider the investment material before investing, including objectives, risks, charges and expenses. This and other information can be found in the Innovation Funds Prospectus at fundraise.com forward slash innovation. This is a paid sponsorship. As always, I serve”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
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2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Before we leave you today Today, I want to talk about The financial stack found Grace knows that nearly 40% of startups fail because they run out of cash, so they built a banking experience that takes every dollar further. It's such a difference from traditional banking options that leave your cash sitting idle while chipping away at it with fees to help you protect your cash and extend your runway. Brecks combine the best things about checking, treasury and FDIC insurance in one powerhouse account. You can send and receive money worldwide at lightning speed. You can get 20x the standard FDIC protection through program banks and you can earn industry leading yield from your first dollar while still being able to access your funds anytime. Brexit is a top choice for startups. In fact, hey, it's used by one in every three startups in the US. Just check them out now, Braxt.com, forward slash startups. And talking about building trust, Atio is the next generation of CRN setting up”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“The feeling is completely mutual. I'm a fan, but honored to be a friend too. And I'm really excited to be with you, Harry. And this is a lot of fun.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't want to be paternalistic, but my colleague Tiago, who one of our key leaders here, he said, look, people think they're happier sitting at home and they're not. And they end up quitting like a week later. They say, no, no, I love working from home. And then they go quit. Why? Because they're disconnected. They're not part of it. They're not with people. It's not natural just to sit in a room and like crank all day without collaborating and whiteboarding and talking. So I'm very excited about the track we're on. And I've had to literally stand up in front of the company and say I was dead wrong. I'm sorry. I'm going to own it, but this is the direction we're going. I wish remote virtual and distributed on all of my competitors.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a special element too. It's something we didn't talk about the work for work from work stuff, but I made a mistake on that. I went remote, virtual, and distributed in 2020. I'd been getting the crap beat out of me. Well, we were in Redwood City and struggling to hire and struggling to compete. And things started to break before COVID. And COVID hit, I go, you know, move home with your folks or go to the beach, keep your salary. We're a remote virtual and distributed and company fanned out. Catherine beat on me, by the way. She said, the companies that get back to the office first are going to win. What are you doing? And I was like, oh, come on. There's been innovation in the world. You don't know what you're talking about. And the reality is I was dead wrong. We're getting back into the office. The collaboration, the productivity, like it's not even close. And it's very painful getting back into the office. And you know what is worse than that? It's not getting back in the office. It's the disaffection. It's the”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I was talking with my friend David Peterson. I was in New York late last week, and I caught up with David. And you know, Ryan, I think probably pretty well. And David said his dad was a computer scientist, a programmer while we were growing up. And his dad retired early and has been retired probably for like 20 years. And we were talking about people who don't and don't stop. And he said, you know what? I think some of these people who are cranking in their 80s actually have a higher quality of life. I said, tell me about that. He said, like, I went to on some trip with Nelson Pelts from Tryon and this guy's like still with it and he's still cranking and like people want to talk to him. He's like, there's something about the like stimulation, the relevance, the like being in it. He's like, it's not just a need and it's not just vanity. He's like, I think they might have a higher quality of life than if you just buzzed off and like tutor around in a golf cart.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“You have. I can't even keep up with your content. I mean, it's insane how much you put out. And it's not because you cut it through waves from Sunday. It's because you're literally you are at it all the time and you've been doing this Harry now what? Eight or 10 years?”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Maelstrom, like I'm still in the living daily and hourly and like working like most of the weekends and nights and just like cranking to make this thing go to the next level. It sounds kind of sick, but yeah, it's a total treadmill. We're on it until we're not. I take my job super seriously and there's many hundreds of employees who are depending on me to do that as opposed to like buzz off and play golf in Ireland or something. And so, you know, while I'm here, I'm completely mission obsessed and I want to deliver for our customers, employees, and shareholders.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Know what's funny? Yes, on the one hand, and the other thing is, and you often ask guests, like, you know, does money make you happy? It's helped a lot. And I don't mean that to sound trite. And I hope this doesn't sound super pompous. But like, I grew up. I never felt safe. I never felt safe. I didn't feel safe at home. I mowed lawns from the age of eight. I collect $20 bills and count them and go, you know, literally deposit them and like been pinching pennies in one way or another for like most of my life. There's a sense of security that's come from some of this that like I often will walk around and just try to tell myself like you're okay. Like it's safe. Yeah, I don't know. That's that I feel different than I did five or ten years ago. And it's a no, it's not going to produce happiness. I still need to probably go to the Hoffman process and visit Eselin and do all the things that your other guests do. I need to get on some of those.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, for sure. I grew up, I have a difficult home life. My mother was severe alcoholic and parents got divorced after kind of years of home war zone. I think there's probably something like this in a lot of entrepreneurs. You would have more experience in it than me talking to so many entrepreneurs as you do. But there's the, you know, wanting to prove that I'm good enough or I'm worthy that kind of is part of the drive in some of these companies. This is not just a mercenary activity. This is mission plus that personal pursuit of...”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I thought you were going to ask more about the struggles like this super pain. And we did touch on some of those, but I thought you were going to get a little more personal with me about how I grew up or my mother or this kind of stuff. And I've listened to so many of your episodes and her about some of your background. So I'm not begging you to do that. I'm just kind of being, I was a little prepared to get like vulnerable and have a cry out with you.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, fair. And he's going on that and Databricks and others. And yeah, I mean, I'm in the fun. And so it's exciting and nerve-wracking. And I mostly just want to watch and admire what they're doing.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“You stroke the check. You know this better than probably most Harry or anybody. Certainly, I mean, but when you stroke the check or when you're writing your own money, it's different. I'm writing a check with real money at $150 billion valuation. So I find the investing game fascinating because.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“tend to not invest against Elon. And if I sat down with him and talked with him and said, are you like, is this real and are you all in? And I think he clearly is. I think that's probably a perfectly good investment. I think it's similar to the open AI investment. I was at an event and Mary Meeker was there and I talked with her and I said, man, what around that open AI? I said, would you do it at 150? And she said, to be clear, I'm not in the round. But yeah, I would do that. No question. I said, tell me about it. And she said, look, I don't remember exactly, but she said, 60% chance that company crushes it and becomes, you know, a world-changing trillion dollar company. 20% chance it goes sideways and you get the prep stack back or you get 80, 80 cents on the dollar. And then, yeah, 10, 20% chance it's a big goose egg. And she's like, that's a nice bet.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I would understand a company like Workday. Look, I'm an enterprise software. I sell ERP software. We're almost like a verticalized workday where I'm going with this, Harry, is like to run like a Microsoft. It would take me a lot of time to even understand their business. They have so many business lines and so many discourses of revenue. I think what Satya has done there is like, it's kind of incredible because I don't have a clear understanding of that business and how it works and how I would, what growth levers I would pull and how to carry it on.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I've changed my mind on up-and-comers. I spent a lot of time hiring, been there, done that. I've grown a little tired of it. And I see the value of promoting from within. I see the value of hiring people that are geniuses and want to work like all the time and grow their careers and learn and have kind of the growth mindset versus the, hey, here's how I did it at my prior companies. And hey, look, I'm an exec and I've got a playbook. I'm excited about growing and learning and promoting from within and like hiring like fresh talent that wants to get after it versus the been there, done that.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Look, I think they have to. I'm a little surprised this has gone on the way it's gone on. Databricks supposedly raising the largest private round ever, I think. I guess that's really the point you're making. But my read is and what motivated me a little bit is, look, at some point you've got to deliver the money back to investors. They're raising, Databricks is raising most of that to deliver secondary to employees, including to deal with some tax issues. I know that's what Stripe did. And Josh, I think, is doing most of these. 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. That's going to come. I don't know whether it's in 25, 26, or 27. If I'm guessing it's probably 26, I think the markets opened up and all these companies end up going public.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“If we hadn't sold the company, what would life look and feel like if we were pursuing IPO? I still feel convicted that we made a great decision.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Everyone tells you that it's a life changer and you want to pick the right partner and you got to be in the right zone and all of that. And it's washing over me. Like I've changed my life materially. I've changed it materially. I wanted to go. I think I told you I wanted to go on that trip in November. Like, nope, not happening. We have a five-month-old baby and we're not dragging the baby around the globe. So yeah, my life has changed dramatically. And like I'm just coming to accept the new reality that I don't think I really understood. And a lot of learning is like that. It's got to be experiential because at least for me, you know, people just tell it to you. It doesn't really sink in.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Snap judgments are very valuable. A lot of people tell you you got to be thoughtful, you got to be balanced. You do, especially as the organization gets larger, but you've got to listen to your stomach and your gut. I often advise our execs or others when they've got a big decision, whether it's personnel or something else, go sit in the woods, go sit on the hill, look at the ocean. And what is your body telling you? It usually is telling you an answer and you got to listen to it. And sometimes it's telling you that really fast, like when you meet somebody or when you walk out of a meeting, you know”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“He's tough. He's out to ensure governance and investor interests. And I learned a lot from that. But it was not, I had a warm, loving relationship with John, with Catherine. With Mark is a lot of business. He took his role seriously. So it was a, I wouldn't say it was transactional. And I'll give you an example. 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. at, you know, maybe it was 10 a.m. to 12 p.m. At 12 p.m., Mark literally just holds his chair out, gets up, grabs his briefcase, walks out, slams the door, leaves the building, and we see him drive off. And everyone is just like, what just happened? And I text him afterward. And he was like, you told me the board meeting ended at noon. And it was like a pretty stark message of like manage the board meeting. Stay on time. Run it tight. Be in control. These were the type of, I wouldn't call them evuncular.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“There are two to come to mind. One, I pitched Peter, Teal. I was so green and I just gotten back from Afghanistan and I literally would go to work in slacks and leather shoes like a business lawyer looking type person. The Founders Fund guys, at least in those days, did not respect people who wore button-down shirts. Literally, I got laughed at. That hurt. Number two, I had a few meetings with Mike Moritz. I was very excited. I think that would have been great investors. I was on maybe the third or fourth meeting went to kind of partner level meeting. And I thought this was going to be the one. And I walked in. I could just see something on his face. And I go through my spiel, but I'm like, something's not right. And I just knew he just decided against it. And he was like, what have I done scheduling this meeting? And he walked me out and shook my hand without looking me in the eyes and then just literally turned and walked off. And that brought out very bad feelings in me.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Small checks into a few just to kind of support friends or investors in OpenGov. And that to me was overweighting on privates and just unnecessary. Making less investments is probably a good New Year's resolution.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I put in some money markets and tried to catch my breath mostly. Paid down my mortgage and got back to work. Just stick it in the indexes and go do something else. Extremely hard to beat the market over the very long term.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh, I think there's loads of these. And a lot of entrepreneurs lose. They either didn't have the kind of morals and the anchor weights or they lose it in the intense pursuit of success. Look, I think it's a really hard business. And I'm an LP in some of these funds and I'm waiting for distributions. And to me, multiple uninvested capital and distributions on paid-ins seem like a lot more important than, quote, IRR based on other funds marking things up to impress their LPs. I can tell you post-transaction I'm getting hit up to invest in lots of companies or funds. And it's like maybe I shouldn't be so overweighted on privates.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Oh man, I started writing bigger checks thinking, of course I'm a genius, that the checks I wrote in 13, 15, 17, you know, fantastic companies, flock safety and attapar and qualia and flexport and other things. And it's like, oh, look, I'm good. And then I like write bigger checks into earlier stage companies. And they go absolutely nowhere. Even some frauds, just straight up frauds where it's like, wait, you said the numbers were this. They weren't that. You just lied about it.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I think overall the venture asset, and I don't have all the numbers, you might, but I think the venture asset Where's the money? How many years has to go by? People think these companies take like five, seven, nine, ten years. Not true. Not true. They take like 15 to 20. That means your venture fund takes 15 to 20 years to distribute the money. Typically, unless you're selling kind of secondary stuff, in which case you're probably taking a discount. I think the asset class, you have a very, very tough job. It's hard to be a first class venture investor in terms of returns. I think the last few years have probably been pretty bad. And there were a lot of people that were like, I'm the best investor in the world. And yours truly made lots of stupid investments, like really stupid investments. What was your most cheap?”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Manage my adrenaline. The deal ended up happening in February, and Alex Taylor, the chairman, CEO of Cox, came out and we announced it to the employees. I was so amped up, exhausted at the same time, very excited, felt like I was making a good decision, but like I wasn't present, if you will. Do you know what I mean? Like I wasn't like living the moments. And in terms of the signing, it was literally just execution. The number of deliverables and the number of variables and even at the end, the amount of people that have to be aligned and the squirrely things that happen, it just became like tunnel vision execution mode. I spend a fair amount of the year literally processing and digesting and trying to reset because, you know what I mean? Like we're amped up for the next chapter, but like we got to turn the page.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so it was really wild. I spent probably the better part of six months on this. It was exhausting and nerve-wracking. In December of last year, I started breaking down. I was like breaking. I got sick three times in December. I got hand foot and mouth disease. I didn't even have a child. I got some Victorian era virus. I'm like breaking out and things. And this is in the middle of the price negotiation. I remember Chambers saying, Zach, sometimes you got to play hurt. And I'm like propped up talking about big numbers while I have 130 fever. That went on. We're supposed to close in January. I had like a baby moon or a pre-moon booked in Hawaii. I went on the trip. The deal got pushed by a month. And this is at a point where it's pushing and you're wondering if it's actually going to happen. These things do break. And I'm in Hawaii. I am on the phone like two-thirds of the time. The rest of the time I'm literally like in the gym like trying to make.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, of course. I'm starting a family, and there's all different levels. So keeping grounded, it's one of the reasons I love our company. You find the end market boring as hell. We find it fascinating. We're proud of what we do”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure, that sounds right. I think it depends on what kind of crowd you run with and what you care about and your values and other things. I mean, if you, you know, if you want like a two-bedroom in the suburbs, fine. If you want the flat and mayfair overlooking the park, you know, and you get caught up in it, there's always more. There's always something better or different crowd.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Now, look, people aren't entitled to their views, and that is like a common view. And I get the view. I just think I disagree at this point. 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. It's actually a decent way to encourage the entrepreneur to play smallball. For somebody who grew up without a lot, you know, mowing lawns to go be able to make like X millions or tens of millions. It's like as soon as you get to a certain stage, there's a natural tendency potentially, you're like encouraging the person to grip tight when actually what the VC wants more than anybody is for the person to go long and go really, really big.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Know there's an old scroll Silicon Valley mentality on like keep the founder poor don't give them secondary I had a board member who said I wanted to sell I think like 400 grand to like I mean I was in my like mid 30s I'm trying to like paint my house and like get something set up I got the if you're selling I'm selling And I'm like, that's pretty harsh. Like, I don't have much. And you do. And that's a weird speech you just gave me”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Look, these companies, the investors at growth stage kind of maturity end up owning like 80% of the company, 75 to 85% of the company. And management and employees and founders own the remainder. So my family safe. I'm in good position. I can tell you it has changed my anxiety levels. Those who knew me, I would come in some days tweaking and like grouchy and like very fearful because 98% of my net worth is locked up in the company. The last five or ten percent of that anxiety is gone. Like I can sleep most nights. I don't wake up at 4 a.m. at like a pit in my stomach and like, you know, like, oh, I'm dead. Like we're dead. That mostly has gone away, but I'm still kind of obsessed. And that was the deal. Cox doesn't want to buy a company and not be in bed with the founder. And this was not just sell it to Oracle, cash out, and buzz off after 12 months. This was a different type of deal.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Pool to continue to attract great talent and compensate people. And we have defined liquidity at years three, four, and five. So essentially it's a put right. You can sell a third at year three, two-thirds at year four, and three-thirds at year five. And Cox has a call right in the out years so that if they want, they could eventually obtain 100% ownership of the company. I'm in very deep on the company.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, when we did the price negotiation, we were probably 110, 115, something like that. Very quickly, we've surpassed 150, you know, near 15x at the time and we're burning it down now is an interesting deal in that I left a majority of my stake in the company. I'll tell you about this. It's a supposedly common-ish structure in kind of telecom and media. And I think it's a little innovative in your classic kind of software or tech ecosystem. I basically as management went into business with the Cox organization with a new investor. All the existing investors were swept out and cashed out at the 1.8 valuation. The board was shrunk from eight to four. It's me plus the Cox team. Employees vested equity was cashed out. So it was essentially a large secondary for employees. But all equity plans remain in place. We got a large RSU.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Want this. I call the board meeting the next day, and they say, What do you want to do, Zach? I said, I'm a no. And they were like, whoa, really? And I said, yeah, shall we end the meeting? And then they were like, you know, this is pretty serious valuation. A lot of deals aren't getting done right now. And this is a good IRR and I said, look, we've talked about going to become a multi-multi-billion dollar company. We set up a hole. We hired Wochtel. We set up a whole process. We spent like five months working on the deal. We got the board aligned and we did price negotiation. We did a management incentive plan. And we put together what I think at the time was the third or fourth largest private software transaction of the last few years.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“We sold the company in February for $1.8 billion to Cox Enterprises. This is a large family business in Georgia. They own the largest private cable company in the United States. They own the largest automotive company outside of the car manufacturers. And they're diversifying their 125-year-old family business. They understand growth durability. They understand customer acquisition costs. They understand regulated businesses. They understand services. I call them last August. I guess it's almost a year and a quarter ago now. And I said, hey, you've been rubbing my thigh and whispering in my neck. If you'd like to put a term sheet down for $2 billion, I think this board would take it seriously. They produced a term sheet for 1.5. I rode my bike home that night and I got really nervous. And I said, I might have made a big mistake here. I don't want to sell the company for 1.5. And yet I think this board is probably tired. They've been in for a long time. They might.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“No, no, no, no. Even the M&A, the reason I executed the transaction we did earlier this year was I looked out and said we could get ready for an IPO in a couple years, maybe less. And then what happens? We could raise a bunch of money, but to truly live the destiny of this company, we're going to want to buy other companies. So you could do secondary offerings and it just starts, but then you're like, you're on the quarterly game. And I'm like a long-term owner with very deep pockets that's super mission aligned. This is how we're going to build the biggest company that's going to live its mission. No, probably not is the short answer. So if I had to pick one investor, definitely be partner specific. I would go for kind of name brand as good an investor as I could get based on the returns of that investor. But I'd have a very serious chat and say, I'm running the company. Are you comfortable with that?”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm serious. If I was going to do something again, I'm enamored by the bootstrap idea. You reduce a lot of conflicts. You own way more of it.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“The CEO needs to explain the direction, sure, gather input, but boy, there are times, Harry, where Mark would be like, I've seen this 10 times, you got to go right. And Lonsdale or somebody else would be like, nope, I've seen it 10 times. You got to go left. And I'd walk out and I'd be like, what do I do? These are both like people I look up to. And it was through this process I said form your own opinion, become a real leader and a CEO, use your independent judgment. You've got more facts than they do. Make the call.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I think a lot of experienced CEOs really understand this, and a lot of founders and folks that are new to it, which is where I was for many years, I didn't understand the board is for governance. The board is for governance. They're to make sure that there's no fraud. And it's a real company, primarily to hire and fire the CEO. They represent the stockholders in the sales process that is fundraising, which goes both ways. A hot company is being sold to by investors. It's easy to get confused and think, oh, these are my, just my mentors and coaches and friends. And like, we're in this together and we're partners. One thing I learned from Mark and even Joe in the later years is like, we have natural conflicts. My job is to grow the share price. I need to, A, to deliver on the mission and win for our employees and customers, but I need to win for our stockholders. That's my principal job. When you go into the board meeting, you're the chairperson. Whether you think that or you have that actual title, the CEO needs to run that meeting.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“I would move faster, I'd be more decisive. If I knew now what I didn't know then, I'd probably have saved three years. And I would move at a tempo that is a different tempo than I was moving for the first five years. It's removing people that aren't working, product decisions, the sales machine, the enablement machine, the hiring machine, enterprise software rewards intensity and focus. You know, they amp it up article from Slootman and his book. It just feels spot on. It's not one philosophy. It feels like it's kind of like the way these companies are supposed to work.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“It's a huge time suck. It's definitely not fun to get said no to, but that's fine. I sell every day and that's no big deal. It's just, it doesn't actually create that much value. A lot of people talk, oh, I raised this much, hundreds of millions or these valuations. It's literally irrelevant. You will be judged and weighed by your exit and by the liquidity that you can provide to people. And so there's these tremendous roller coasters that go on between the time you take the money in and the time you got to give it back. And I think a lot of people lose sight of that. You overcapitalize the company. I mean, it's just more you got to, that's a higher pref stack and it's more dangerous for the common stock, which is management and employees. So I just found it was kind of like not a great deal in many respects. And the tighter we got, the better we did. So we started to get to cash flow positive and EBITDA positive. And it was like, great. Like, let's keep this going. I don't want to return to those days.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Honestly, it got harder all along the way. The easiest rounds were early. You know, Joe had come out of Palantir, tremendous network and credibility. So I'd say the first few rounds kind of came easy. That was a blessing and a curse. It was a curse because we overspent. Like one of the many mistakes I made was to overspend on sales and marketing before we had the product. And you probably see this in some of your companies. It's very dangerous if we didn't have some of these unfair advantages. We would have been dead pretty early, like in 2014 or 15. As we got further along, I think we got more attractive in terms of raising money, but I also got way less interested in raising money. Like I wanted to literally stop raising money for the past five years”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“The short answer is yes 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 came back from Afghanistan in the summer of 2012. I was like, wow, I used to be somebody. You know, I was a lawyer and I was in foreign policy and I was doing things. And now I'm like in this like dank three-bedroom apartment style office, hiring and firing and making like a total mess out of everything. And I was like, what have I done? But it's a burn the boats kind of thing. I've already made the mess. So why don't we keep going?”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, there's been many. And the CEO has to give the energy. It's one of the hardest parts of the job. It's literally how much do you have to give? And you drag yourself out of bed. How do you give to your employees, your teammates, your customers, and just give your energy?”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“The earlier, the better. You've got to manage to keep the cart on the tracks. That requires management and requires leadership. Creating new products is part of the magic and pulling the trigger on bold bets, whether that's a new product direction for the company. And sometimes people are crying in the streets like, no, I thought we were a budgeting company. Well, we still are a budgeting company, but we're becoming a permitting company as well. It's amazing the internal resistance you'll get, but you got to bake it into the DNA and the culture of the company. Again, that's just like leadership and execution. And some people get left behind. It's all for service of the company and the customers and the mission.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source
“We get an inbound. If you gave me an inbound from the central office of the UK, we're not responding. And our sellers, they can't prospect outside the ICP segmentation. And so having real discipline and knowing the only thing you have is time. You have 40, 60, 80, 100 hours a week. That's it. So how much ROI can you deliver on every hour of your time? It goes up if you shrink the TAM and the shrink the PMF segmentation.”
2024-12-06 · The Twenty Minute VC · 20VC: From Unsexy Startup to $1.8BN Acquisition | Why VCs and Founders are Fundamentally Misaligned | Why Valuations and Fundraising are BS | Lessons from Josh Kushner and Marc Andreesen | Zac Bookman, OpenGov · IDENTIFIED FROM THE TRANSCRIPT · source