YouSaid · the spoken record

Dan Siroker

lines on the record: 87
first: 2024-05-15
most recent: 2024-05-15
sittings or episodes: 1
sources: podcast

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“It would be millions of users, active users daily. One of our biggest advantages today is that we're weird. People look at our product and why would I capture everything I say in here? Like, what's the purpose of that? And it would go from being weird to being accepted. It'll be like airplane Wi-Fi. You're like, wow, that's weird. And then it's like, oh, it's not fast enough. It's a societal change around the conception of what we do, the benefits of capturing what we say, what we hear, what we see, and using it to augment human intelligence with artificial intelligence, not replace human intelligence, augment human intelligence. To me, that would be success in 10 years is that our product is taken for granted. And it's people thinking about today and saying, wait a minute, back then, you know, you mean in 2023, when you wanted to remember something, you took out a rectangle that you chopped down from a tree called paper. You had a stick with ink at the end of it, and you scribble things down. And that's how you remembered. That was the thing you thought was the best idea to remember. And that people would laugh at that concept. That would be success.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“It is likely to have quite a bit of headland regulatory wise and certainly, you know, the bill is passed, so they've got a year to sell it. And, you know, the rumors are now that, you know, Donald Trump's going to come in and make the key part of his platform that he's going to unban it, which might actually work for him. So a lot of this posturing and a lot of government intervention here, maybe more around trying to appease what it takes to get re-elected than it is actually making good policy. So I don't know.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Here's a good analogy. We could look at AI today the same way that before SpaceX people looked at the space shuttle. Like, hey, we have the space shuttle, then we retired it, and now we just stopped going out of space. And it wasn't until SpaceX came around and new technology was built and entrepreneurs like Elon Musk push frontiers that things get better. And that could very well be true. You know, who knows? I hope not. I hope we have a thousand flowers bloom and a lot of startups. And I hope a lot of new innovation, but people like to cling to their pearls, you know, like technology changes hard. And certainly when it can impact your job, I don't think it's a 0% chance that the doomers win.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't know. I mean, governments have control. They can do things to you, and all it takes is one or two bad policies here and there. We are not that far off from regulatory capture around AI models that the unfortunate challenge is the doomers are on the same side as the regulatory capture. And there's a lot of money at stake. So, you know, doomers plus regulatory capture. I could see creating a world in which a lot of AI innovation is stalled. And you add to that that in order to do a lot of foundation model AI innovation, you need to spend a lot of money. So if it were true that it was as simple as, you know, for example, the internet where you didn't need a lot of money to start an internet company, you could ride off of the distribution the internet was naturally giving you by having more people joining the internet. You could just, you know, back in 1996, even 2000, you could just put up a website if it was any good, it would grow. And if it wasn't, it wouldn't. That's not so true today of AI. You need a lot of capital. You need hopefully the government get out of your way. It's very possible like kids grow up in a world where we look back at today as kind of like the renaissance.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Approach to technology innovation that is cynical. You know, I think there's a time when I started optimizing 2010. Where was cool to be a founder? Like even in San Francisco, it was cool to be a founder. And then I think, you know, after the bus, the Google bus protests and, you know, it was actually, I think the movie Silk or social network that actually propelled a lot of people. That brought in a lot of sort of entrepreneurs. But, you know, you had a period of time where like being a technologist was cool, building something was cool. And I think that was good for society. That was good for entrepreneurs. And that's not always true. There's some countries where that's certainly not true today. In the United States in particular, you see what just happened in Florida, banning lab-grown meat. There's a counter movement against technology and against optimism that I think could be really dangerous. And we could go into the dark ages. That's happened once at least once in the history of society.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“What worries me most about the world I grew up in and today, frankly, is doomerism. It is cynics around technology. It's people who see, who are clinging to a past that cannot and will never exist, and sort of”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure. No, I definitely value and appreciate that. And it also creates a certain level of focus in my life that I didn't have before. You know, I have a purpose, a meaning, and in a way that like you kind of miss if you don't have, and you don't see the other thing I love about, you know, this is a very techie answer, but I love watching how they learn and how they grow, imagining the parallels to AI and AGI and seeing and understanding intelligence and what it means to be human from first principles to witness to see a human being learn and observe the world in a world when AI and technology can do the same today is also incredibly lucky and fascinating to be able to do both and become an expert at learning both at the same time has been really fun.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I'm not ruling that out. I certainly think now is not the time given all the other things on my plate. And I'm just loving and enjoying. When kids are at this age, like, I didn't appreciate how nice it is that they just want the most valuable thing to them, the thing they love more than anything.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“It's just a lot. So that's what makes it hard. I think now in hindsight, one was not so hard. Three is three kids too hard.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Especially the early days, there's just these tiny little human beings who you have to feed and care for who are never stopping. You have this window of time before they start walking where it trains you. And I think that's probably why humans have evolved to walk later is to just be too much. And I've also this theory, humans in general and probably kids in particular have learned to nap and sleep just to give parents a break because otherwise the parents would just throw the kids away. It's just too much if you don't have them napping every so often. And it's also just, it's physically hard. It's emotionally hard. And then combine that with a startup, which is mentally hard. By the end of the day, you're just drained. And I'll be honest, like, I've cut out basically, I don't spend much time with friends. I have basically no hobbies. I'm reminded of this Rick Rubin quote. He's like, I have no technical skills. It's like that. But for my life, like all I do is spend time with my kids, my wife, and work. And I'm happier than I've ever been in my life. So it makes you create a level of focus that, you know, and of course, it's different with one kid versus three. Three kids was.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“It is going to be harder than anything you've ever done before. Set expectations incredibly low. If you're going to do this well and focus on what you care about, you're going to have to cut out a lot of the things in your life that you think are important to you, but you'll realize very quickly once you cut them out or not.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Sam Altman or Elod Gill, two folks who have been very helpful to me who don't launder on our board and probably don't need to or want to be, they're two fantastic people who have always had pressian advice and sort of deep intuition for the market and have both been honest and candid. That's the other thing that you often, I need a board member as somebody who doesn't shy away from saying the hard truth that you need to hear to try to save your ego. So especially a lot of, very much appreciate that in the past.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I probably should have. I kind of regret not doing it. I think I was maybe too much pride and ego that I didn't need it. YC has a lot of gifts to keep on giving, even if you're a second time founder, like work at a startup, like office hours. So I am very impressed with Gary's reinvention of YC recently. So I probably, you know, I regret it. I probably should have done it again.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“If I had to give you any advice, just focus on the problem. Care enough about the problem that in the way you talk about your product and your launch, the problem is very clear. That's a big mistake, I think sometimes founders make is they do this big fancy launch and by the end of it, people are scratching their head. What problem is this whole thing? How does this help my life?”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“To, I guess, down on myself and maybe too ego driven to see it had to be my idea. But I think both of those are things I said no to or said no to that I should have said yes.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“At optimizedly we said no to areas that ended up being huge successful companies. Product analytics is a good example. I tried to buy amplitude when there were four people. In fact, they were about to raise their, I remember were sitting at, I think, at Chipotle and Soma with Spencer. And to this day, I'm so impressed with it. I was offering him insane amounts of money, life-changing for him. It was four people. And they took the term sheet from benchmark and said, that is one where in that moment I should have just said, okay, we're going to crush them and do product analytics. I think too much of my ego is associated with that. I should have been more zuck-like and just said, okay, they didn't accept our offer. Let's go just beat with them. We already had the distribution. We had the market, you know, and we could have been amplitude or more and amplitude is now big public company. Another example is segment, another area where it was adjacent to what we're doing. We tried to acquire them. There were later stages then. They said no. They ended up being successful. So we had these sort of adjacent ideas that were actually really compelling that we saw early enough. And funnily enough, both of those companies, I thought, oh, it's too late. Amplitude's got this huge lead, you know. And so I was too.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“It's like opening a commitment that you have to keep feeding. So, again, it goes back to saying no, being decisive, choosing what you think is the most important. The main thing is the main thing should say the main thing. What are the key features that users actually care about? What will they actually use?”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“This is one of the things that I think the CEO really needs to lead on because it's very hard for anyone else, the company, to say no, especially when it comes to customer says, I have this problem and you have an engineer who says I know how to solve it, and then you end up with a product that solves a customer problem by itself, that's not that bad. You know, that's good that you have engineers who are empathetic and listening to customers, but that times 100 features, you end up with a bloated product that isn't really focused. I do think as a founder, you're able to take in and understand and sort of into it the market, the customers, investors. Ideally, you have a good enough understanding of the technology to understand the effort necessary to build things, not just the effort to build it up front, but the effort to maintain it. So you have to know that everything you build, I have this saying around building features that no good deed goes unpunished. I think I have to, I've never seen a situation where we'll ship a little feature and we're done. It's always like, oh, shoot, and there's this edge case we didn't think about. And oh, this other person wants to do this other thing.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, I think every problem can expand over time. So I don't think it should be so much the problem big enough or small enough. In some ways, actually, you kind of want to choose founders who are excited about smaller problems because it tells you that they're not just falling in love with what they saw.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“It's not that they're sort of wed to this ideological idea. So I think that's the filter you should use. It shouldn't be is it app layer or foundation layer? It shouldn't be first time or second time founder. It's this font founder obsessed with a problem in the world? Is a problem real? Are there other people have that problem? And do I have confidence that this founder will persevere to try to solve that problem and maybe have some of the skills necessary to use technology to do that? Not, oh, cool. It's like Mistral is the latest greatness. Those things are ephemeral. I would focus on problem obsessed founders.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I think the most important thing to do if you're an investor today is find founders who are obsessed with problems, not solutions. Many founders, especially X crypto founders, tend to think of AI as the solution to all the problems in the world. And they're actually technology in search of a problem. I learned this anti-pattern at Google, actually. I started my career there as an associate product manager. And Google is notorious for building products that are technology in search of problems. Google Wave, Google Buzz, Google Glass, like all of these products were basically some smart engineer or technologist starting the sentence with, wouldn't it be cool if dot, dot, dot? So if the startup you're evaluating or the technology you're considering began with the origin of wouldn't it be cool if dot dot dot? And the cool isn't problem. The cool is technology in search of a problem, then I think that's a very strong anti-pattern. I would focus, and that's the only companies I really invest in today, are companies that deeply care about the problem. And it just so happens that maybe AI or technology can solve it.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I probably gave him some answer that I felt was true, but if I had really listened to that question, I think I could have done a much better job of staying in love with the business. Because I think what he found basically, and maybe this is just his track record, is the companies he's taken public, they're all founders who have just been perseverant, who can keep it up, who stay in love with a business five, 10, 20, 30 years into it. And I think I mistook that question as, oh, that was an interesting question. I thought it was maybe he was trying to flatter me. He's like, oh, he wants, but it was really actually trying to understand what motivates me, what drives me. And that's something I definitely learned with limitless. You know, I will be at Limitless is my life's work. I'm going to be doing this even if we failed. I'd be proud to have done the kind of problems we're trying to solve. That was probably the most memorable meeting.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“It was probably the first meeting I had with Peter Fenton in 2013. I think it was mostly the most memorable. The first reason it was memorable is because he came in with this entire contraption around his knee. He could barely walk. And the reason was he had just been helicopter skiing and he like broke his knee or something. We still showed up to the meeting. He then, by the way, he thinks a similar kind of dynamic with me where he has to sort of proves the world other things. Anyway, he winded up to learn how to fly helicopter after that because he wanted to conquer the thing that had broken his knee. Anyway, the reason I remember it, because I remember so vividly the very first question he asked me, which at the moment I had no idea why he's asking or why it matters. And now with hindsight, I totally get it. The very first question he asked me was, Dan, what's going to get you excited to be at this business in five years? And this is 2013. In 2018, exactly five years later, it was exactly when I started to feel trapped, resentful, disengaged, going through emotions. And he exactly astutely figured, asked, and pointed out.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm gonna add you to my investor update list and I will look forward to just for the Ataboy or a good job or here is how I can help you sold me.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“No, I don't. Actually, I think more likely, I mean, I have some of the world's best investors, and now I've come to accept that they're busy. I'll send an investor update. We have on my investor update list. We have maybe 300, 200 people. And, you know, I'll get on a good email, maybe 20 responses, or like, you know, something, or if I ask them to do something. But most people, they're just one of many companies. So you just got to recognize that like even great investors, you're just one of many”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“And that's your employees. And so if you want to do best for your employees, you want to rationally control as much as you possibly can around the outcome of the company for them. So advocate on their behalf and likely your own because you're also likely a large common stockholder. Be willing to push for things like supervoting and multiple board seats.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“They don't recognize control as an important thing to maintain. There's the same Ultimate Camp, which is like, you know, you got to trust people at the small percent risk that you're going to get screwed over. This was before he got screwed over. So he had a very kind of like, you know, you do right for the world and they does right for you. And I wonder if, you know, I should ask him what he thinks now. I do think when you think control and you think governance, you shouldn't view it as you're offending an investor. Like an investor was highly rational. They would also ask for and want as much control as possible if they were the founder. And many former founders who are now investors understand that they wish they had more control. So things like supervoting stock, I think you should make sure to ask for multiple board seats. You should ask for not having board members, maybe having board observers instead of board members for certain investors. It's hard to ask because it kind of can feel a little personal, I think, because like, well, you don't, you don't trust me. But at the end of the day, you're just being rational. You as the founder of the company are actually, as a fiduciary, responsible to represent the interests of the common stock.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I mean, I think it's very possible, especially in a situation where during ZERP, a company raised at X valuation and they have too much pride and fear associated with that valuation and they're afraid of taking a down round if they need more capital. And so they trick employees by saying, hey, we raised an up round. But behind the scenes, what they really did was they added like a 2x liquidation preference, which almost always means no employee is ever going to get any of their stock worth anything. So I do worry about that. But if you're a founder listening to this and you're contemplating an up round with a liquidation preference more than one or a down round, do 100% of the time, do the down round. It is much better for you as a founder with Common Stock. It's much better for your employees. It will hurt in the moment when somebody says, oh my gosh, this company that I thought once was worth a lot of money during Zerp is now worth less, but that's fine. They'll leave or hire somebody else. Like you'd much rather be in a company with less overhang on the valuation, on the liquidation preference than one without.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“At every stage up until the very end, they're pretty well aligned. You know, you get into these situations near selling the company where maybe the motivations and incentives are slightly out of alignment. I think a lot of founders actually have a very binary view on outcomes. They think either it's going to go to zero or it's going to be multi-billion dollar public company. We're actually, I think, more likely than not. They're discounting kind of the middle of the road outcome where maybe it's 2x what you've raised or 3x or maybe it's slightly more and things like liquidation preference are really important. And you know, so I think those are the kinds of things where you do need to model out and think through what are the different middle of the road outcomes and how you might be misaligned there. So make sure you're not, for example, raising too much money and then getting to an outcome where investors have a very, very different financial, you know, they're basically like, for example, I just make it very plain. If you sell your company for as much as you raise or slightly more, the difference between as much and slightly more is incredibly meaningful to your employees.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“That probably helps. Maybe I don't appreciate that quite as much. I haven't heard that, but I assume that's happening as well. So that's one benefit.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I think it helps. It's not the difference maker. I think it helps with recruiting. Great, great talent can work anywhere. And if they have the choice between a company that's got great marquee investors who've done their homework, that de-risks the founder to them, that de-risks the company. So I think that's probably the most tangible benefit. It maybe marginally helps with customers. I don't think so. If you're B2B, maybe in the enterprise, it might help. But for the most part, I think it helps build a movement and sort of traction and momentum in the market. It probably scares off competitors. I did notice this that one of the beneficide unintended beneficide benefits of the round we raised, I do think kind of made everyone else's job, who's a founder trying to compete with us much, much harder. Because first of all, we had hundreds of investors. So now that all those are conflicted out and you get this sort of momentum, it's like, oh my gosh, how are you like all the questions they're getting, their appendix. Appendix slide number one is how are you going to compete with Limitless? You know, how are you going to compete with us, especially given all of the who's who's invested?”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Time proportionally to where they can have the biggest impact. The way I sort of, you know, it hurt a little bit in the moment when I sort of recognize that, but you also got to understand like it's a business. They're investors, that's rational. You're the founder. Your job is to make the company successful. You can't outsource. The one thing that really kills me is when I see a founder playing the victim here and say, well, my investors didn't help me enough. Like it's not their job. Their job is to give you money and hopefully do no harm. If you got some help along the way, great. But like your job as the founder is to make it succeed. And so playing the victim and assuming your vestor is the reason you're going to succeed or not, I think is you're lying to yourself and lying to your investors.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“The thing I noticed is well, there are some investors who just out of competitiveness, I think more than anything, are going to be helpful no matter what. They just can't not be helpful because they just feel like it's kind of in their DNA, but they're not doing it actually rationally. Like if they were rational, they would probably spend more of their time on the other parts of their portfolio where they could have a bigger IRR impact to their fund. And so there's a certain set of investors in that camp. There's others who, I'll be honest, at some point it was clear that optimizing was going to be okay. We sold for a nice outcome, but it wasn't a multi-billion dollar public company. And I could tell some of the other investors were like, okay, I'll do the minimum necessary. I'll show up to the board meetings. I'll do the work I need to, but I'm not going to bend over backwards to help recruit you the best head of engineering I can possibly find. That just happens. You have to know that too. For a period of time, you'll be the darling. You'll always have them. If you raise money for a period of time, even after you raise money, you'll have the darling effect. But then quickly, you know, as if they're being highly rational economic investors, they're going to.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Thing on this has actually changed quite a bit. I think the best investor you can have for your company is somebody who's on the rising arc of their career. You want a Peter Fenton when he's 35, not 45. You want nothing to be age, but you want somebody before they've had their first IPO. And you want them to be the person who's going to have that. You're betting on them just as much as they're betting on you. Because what happens when somebody's had a lot of success and no knock on the people, I've got to work with amazing investors who had a ton of success, like Peter Fenton and Mark Andreessen. Like they've had a lot of success. Like for you to truly be the difference in their career or not is pretty unlikely. And so you want somebody where they just in their bones and in their pocketbook, you are the difference between them reaching the pinnacle of their career. And so that's, you know, the same way that you'd rather get an NBA player who's in the prime, not somebody who's on their way out of their career. And they've done great things, but I think you get the best out of somebody when they are, when they're aligned around trying to build something with you, not because they're just a fancy logo on their many.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“That's exactly right. That's exactly right. Oftentimes, especially, I found this too. When you very quickly can tell if the person you're meeting with, they have an inclination they want to invest almost from the beginning. And all of their questions you'll find out, actually, I think, are often the questions they think their partners or the senior partner at their firm will ask them. So they just want free, give me some ammo so that when my senior partner comes back to me and say, wait, hold on, how is this differentiated in AI? And isn't this commoditized? And how are you going to pick something in the app layer? You have all of the things ready to go. You're sort of like, you've done their job. You've sort of done their homework for them. And that's, and you're in a good mood, when you're in an investor meeting and you can kind of get this vibe that they're asking the questions, not because of their interest, but because they're about to go sell their partners. That's a good sign.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“This away, but anytime I get a question there, I almost always either change the deck or I'll add a slide to the appendix. So if I ever get that question again, it's very impressive to somebody, I think, when you say, when they ask you, oh, well, what about Apple? How are you going to compete with Apple? And they say, oh, let me pull that up in the appendix. And I have like a beautiful, well-articulated with transitions slides in your appendix. If you can answer their question with a slide you've already prepared your appendix, you at least show the investor that you're prepared. You're not just winging it. So that's another reason I meet with associates is to build up my appendix.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Yes, I mean, I'll say yes, but I'll say yes in a way that's probably reinforcing the part of the Twitter verse that Think associates don't have my value. I view them as practice. I view them as if I can get past. And oftentimes when I did this, these are associates who didn't even Google me ahead of time. They show up 10 minutes late to a 30-minute meeting. But if by the end of that meeting where they care, they're just mailing it in. They show up. I use those 20 minutes I have with them to really nail it. And I really practice my craft in the same way that Chris Rock will go down to New Jersey, you know, the dive bar and nail, if you can nail your craft there with a 20 minute disengaged associate who doesn't really understand your business, you can really nail it with the people who understand your business. And I know others disagree. Some people think, you know, I think Keith Wabas said like, you know, the questions you get from a truly great investor are different from the ones you get from an associate. And there's definitely some truth to that. But I think that by nailing it there at minimum, you know your deck is polished. You know you're answering all the right questions. You've heard a lot of the objections ahead of time. For me, my secret is I probably shouldn't be.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I very much believe you should either be in fundraising mode or not. The one thing I actually really recommend. So before I did this public fundraise, the way I actually practiced and actually got the story in a pitch right was anytime prior to that, some investor would reach out, I would actually send them a calendar link for my investor week. It was a week somewhere usually it was like once I did think at the time I was doing it maybe once a quarter. Now I do it once every two quarters where I just do back to back, usually associate meetings where I hone the pitch over and over again. And I just, when they reach out, I say, hey, super interested, but right now I'm not fundraising. If you're interested, book a time. And so you build up sort of these bookings that then the week comes and then you're investor mode. So you can get out of product mode or customer mode. You're not kind of distracted along the way. And you can really, really hone a pitch. When you have like 30 back-to-back...”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Just to just reach out. And I got this great conversation to talk to 12 amazing people. I talked to every single one of his references, and that's how you can really get to know somebody. The sale part, when they meet you during the fundraise, you get a really unique, narrow view of them. You really get to understand a person when you do the references on them afterwards.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I think there's definitely some truth to that, but I also think the opposite, like when somebody, when an investor, and usually some associate reaches out and says, hey, we really love your business. We love to catch up. That's them kind of being transactional too. That's their full-time job to get meetings booked for their senior partner. And when you meet with that partner, it's not really building a relationship. It's them evaluating you to be decided, should we preempt their next round. Not to say that you should treat their lack of relationship building and transactional nature with your own, but you can very quickly get up to speed with a lead investor like I did with NEA by doing a ton of references. You know, as soon as it's clear that you're going to potentially get married and take a term sheet, in that moment, you can ask them, give me the contact info where every founder you've funded in the last five years. And, you know, even Peter Fenton did that. Peter Fenton, when I asked for references on him, at the time, he was this amazing luminary. I asked him for references. He gave me 12 founders and CEOs. Their phone number, their email. He didn't even introduce me.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Calendar, and I'm going to make a decision by X date, then they work backwards from that. So I think if you don't set those constraints, you end up in exactly the situation you want, which is, by the way, what investor, the investor who's giving you that drim cheek wants to preempt it. They want to get in early. They want to get a better price. And so they know that if they do it before you're getting information from everyone else, that's going to help them. So you should just work backwards and try to avoid it.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“So, this is actually something you can think about and be proactive about upfront. So, I'll give you an example. Last year, when we did this fundraise, we did this kind of in public. We put the deck out. And then for any of the people we felt were good finalists, we gave them a calendly link for the first meetings. And those meetings are all one week. So no more than one week. And that's another benefit of doing this in public is you can do it all in parallel. If you're just taking investor meetings willy-nilly as they come, you get into the exact bomb you're describing, which is you might get a term sheet from one investor, but you haven't even started the meetings with another that you actually want to work with. So I do think thinking about how do we structure and sort of calendar out the raise ahead of time. For me, it was all first meetings are one week. And then everyone asks, oh, how's the round going? Oh, this, and I just tell them, like this week from this day to this is first meetings. I'm having final partnerships meetings. I have three final partnerships meetings next Monday. And then two more the following Monday. And then they have transparency. The thing is, they'd also don't want to miss out. So it's actually a mutual benefit. The investors who haven't given you the terms yet, they want to make sure they're not too late to the game. And then you just set expectations with everyone that's your.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“I've been doing this for 10 years, and I probably need a better answer. But oftentimes, people ask me a very simple question Are you raising money? And my answer almost always is never yes or no. They want just a yes or no. Usually some version of, well, no, but if over the next week we get a term sheet we can't say no to, we're probably going to take it. So that's something, you know, you also got to recognize that are you raising money? Yes causes them to then have this perceived clock that okay if they haven't raised money in three months or six months then what do the other investors know that I don't know so these are small little traps that you can fall into but at the end of the day I don't think it really matters that much these are also marginal benefits you get from sort of understanding where the investor is coming from”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, first thing I'll advise you is I want to just demystify. I want to share some code that you may not know when an investor asks, how much are you raising? What they're trying to do often, they may actually want to know literally the amount. More often than not, they're actually asking, how much do you think you're worth? And let's start the negotiation on valuation right now. Because, like you said earlier, often 10% or 20%, let's say 20% is what they want. If you say, you know, we're worth, yeah, we're raising 10 million. They just take 10 million divided by 0.2, and then that's what they think that your valuation that you think your valuation is. So instead of answering the question how much you're raising, the best answer is, you know, we don't need to raise, so we don't have a budget we're driving. We want to sell no more than this percentage of the company and we're letting the market decide the valuation. That's how I frame it. It kind of pisses off investors because it doesn't play into their game of, again, it goes back to when they write up their memo for their partners and say, okay, what valuation should we go in? You know, it doesn't give them what they need so they get a little frustrated. But I usually say, and the other thing, by the way, that I think I frustrate so many investors.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“It is a factor for sure, and you have to again go to empathizing with your investors. You have to think through the world from their point of view. And especially somebody who's, you know, if somebody says, I want to invest in limitless and they're saying to their partners, look, and I think we should invest in this incredibly high valuation relative to revenue, that you need to understand that they need to be armed with the right evidence, motivation, desires to do that. And if one of the headwinds is, oh, by the way, hold on. Looks like Andreessen Orowis, they invested, they did the seed round. Like, why isn't Andreessen leading this round? Like, you need to have a good answer to that question. And that's something that I do think most founders don't recognize. It comes back to empathy. You have to understand for this person, it's likely almost certainly you'll get one person at a firm if you got a good company, you're doing something well, it's almost impossible not to get at least one person at a venture firm to love what you do. Your job often is to get that person armed with the data information and support to convince their partners that it's investment worth making.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“No, absolutely not. In fact, always saying the highest price is almost certainly going to be a mistake. I know now because I have real data on this. So I actually have a distribution of the valuations we got from the last Series A. We had offers actually 22 offers at a billion dollars. We turned them down and took 350. So we chose, we actually have this distribution. I can share the deck if you want or the graph if you want. But the most common was 200. We had several folks between 300 and 400 and we had a handful outliers at a billion. We not only chose 350, but we also invited everyone who offered more than 350 if it made sense.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“We chose NEA, which has been a great partner. NEA is a very, the thing I loved about NEA still love is they have a very long-term orientation. They're often buyers at the IPO. They're not sellers. So that was a thing that drew me to them. And there's so many things in there, both acts and words that really reinforce this, especially as I talk to references and other founders that they took money from”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“A really, really big decision. Now, imagine if you wanted to marry somebody for love and the only way you could find the person you wanted to marry was you had to drive down this one street in Menlo Park called Sandhill Road. You had to go down five beautiful offices and pick one of those five people. If that was the only method by which you had to decide who you'd marry, you would think that's ridiculous. And now you have the possibility with social media to do the opposite, to do what Tinder or any great dating app lets you do, which is cast a wide net and see who's a good fit for you. And that's what we did with our last fundraise, which is we cast a wide net. It started off not really actually as a goal of fundraising was really try to build trust with customers around our business and showing them we're going concern. And the byproduct is, you know, we put our deck out. You can see it's about seven minutes. You kind of went viral, a couple million views and thousands of offers to invest. We ended up getting many offers at a huge distribution of valuations. And we ended up with a partner who, yeah, we could have perhaps found down San Hoe Road. There were actually an office there.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, it's actually interesting. Each fundraise I've done, I think I've raised probably 280 million in my career over two companies. And every time I've done it, I've actually done it a little bit differently. It's also very much my process for honing my pitch, which is, you know, like a stand-up comedian goes to these Rinky Dinky bars on Wednesday afternoon or whatever to learn what works and to stick with what works. And so for me, each time I've raised money, I've actually done it a little bit differently. A year ago, the most recent time, what I did very differently and worked really well, I broke this sort of conventional wisdom that you should do a fundraise in private and just go down and meet the five investors. Everyone says you should go talk to and hope they say yes. Instead, what I, and so let me just draw an analogy why that's so ridiculous, how like 90%, 95% of companies raise money. Imagine, and I'll just start with when you add an investor to your company, especially if they're a board member, that's like getting married to them. It's actually harder because you can't really get divorced. It's getting married without the possibility of divorce. And if you want to be at your company for five or ten or 20 years, that's...”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source
“Think if you're a first time founder and you find somebody who's aligned around the right values long term, it's probably worth doing. But again, it's one of the things you shouldn't assume you have to do every time you raise money.”
2024-05-15 · The Twenty Minute VC · 20VC: Fundraising Wisdom that is Total BS; Dilution, Meeting Associates, Taking the Highest Price, Always Be Raising | Why Second Time Founders Are More Investable & Why Not To Hire People Out of College with Dan Siroker, CEO @ Limitless · IDENTIFIED FROM THE TRANSCRIPT · source