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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“I've been lucky not to have a board for limitless. I do think generally boards are helpful for first-time founders. And of course, the right board members can be helpful for any company. I think as Vinod Kosla, who said something like 80% of venture capitalists add negative value to startups, I don't know if that's true, but he's not a lot more venture capitalist than I have. And I've certainly worked with a lot of really, really great venture capitalists. Often the best advisors and investor capitalists I've had didn't need to be on the board to be helpful. You know, Laud Gill is a good example. I quoted him earlier, like that was a very pivotal conversation. That was just somebody who happened to be a small investor in our company, who I called and he answered, and we had a conversation. Those are the kinds of things that can be really meaningful. I do think boards as a company gets bigger and bigger and closer to going public are really important for governance and accountability. But when the company is so early on, very, very hard for a board member to get up to speed, they're showing up once a quarter and, you know, you have the context of being the founder. Ultimately, the board may not have. So I generally.”
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
“Different for each stage, and every investor, and that, but it starts with empathy. You got to understand where they're 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
“I think it's fair to give on valuation. You have to recognize that the person who's investing, many times, depending on where they are in their career, they're putting a lot of reputational bet on you. And so you need to give them the thing that they can tell other investors when they're at their fancy Utah ski conference. And they're like, oh my gosh, you invested in this company? Like you did the public fundraise with Rewind then, and you need to tell them, no, actually, here's the thing that I got that is so valuable and every other investor on their peer group says, good for you know, add a boy, add a girl. And so recognizing even just thinking about what it took for that person to be able to do that, I think is important because that's how you get somebody to feel like, you know, every negotiation you're compromising, you want them at the end, you know, you got to work with this person. You don't want to extract every little, you know, you don't want to squeeze them dry so that like the day after the term sheet and the day after defender sign, there's a whole bunch of resentment from day one. So I think that's important is recognizing where somebody's coming from and how you can give them some wins.”
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
“Negotiate one thing that doesn't happen to matter too much to you and matters a whole lot to them. That's a great way to trade something that you really want for something that they might really want.”
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, so this is 2013. Peter was the first person I had met. In fact, it was a very memorable conversation. It was also very competitive. And that's why it led to this, I think, them willing to sort of flex. And obviously, you know, they had certain constraints and I was able to meet them. And it was a negotiation. That's the thing I should say is that it is a negotiation of which every negotiation, everything is up for negotiation. And in exchange for less ownership percentage, they also got a lower valuation. And so I do think that is something to consider. Like that's maybe if I go, if I zoom out and just generally around fundraising, I think some of the most common mistakes founders make is they're not empathizing with the investor. They don't understand the world from the investor's point of view. They'll take like a clip of me on your show and say, oh, Dan says get less than 10%. And they think that that their job is to get everything, everything, everything for them, when really often the best negotiations are when the person on each side of the table is thinking about what motivates and drives the other person to the other table and other side. And if you find common ground, you're able.”
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 appreciate that. But I also did this before I was me. My very first series A, I got benchmarked to agree to, you know, I think it was maybe 8% or something.”
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 those classic things that investors tell the public and most founders don't know the counterexamples. Like there's a bunch of things that are all in the investors interest that are sort of in the lore of how to raise money and what's accepted, what's not. And rarely do people see the exceptions. And so this is one of those where like, yeah, the best investors, benchmark, Andresen, they will invest less than their supposed minimums for the right company. You can't call your shots if you're not doing well, but if you're doing well, you shouldn't assume that just because you've seen that somewhere for the average company, that those constraints should necessarily apply to you. And I think minimums is a perfect example of that. Even if you talk to LPs of great funds and they promise these LPs a certain set of investment theses and portfolios.”
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 used to do that I do think for the most part today the best team is a small team that is tightly lined, highly focused and typically if you think about a team as every person is an opportunity cost and you have got n-squared connections between people if given a spot you could hire somebody to start out of college for you know less money or somebody who has five or ten years of experience I would rather spend more to hire the more experienced person and keep the team smaller than sort of bloat the team by just filling you know butts and seats with 20 people today i feel like we're having a greater impact in ship faster than we ever could with 120 people and software engineers at optimizedly so that's working and i just don't want to mess it up by hiring a bunch of junior people who kind of you know they there's this old saying the best way to slow down a project is to add a person to it so i don't want to do that i don't want to hire a bunch of junior people and help train them and have that at the cost of vervocity which right now is very high”
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 there's something about that ability to provide that liquidity that makes, you know, if you're able to be the difference between them being able to buy a house or not, I think that engender is a certain amount of retentive power that is very hard to do any other way. So I think it's worth 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
“And not as much. I mean, that is a possibility. We don't have that now. We also tend to hire more senior people. Like, we don't hire people straight out of college. We hire people with experience. So we're not hiring people who are super early in their sort of wealth accumulation. And so in general, I don't feel that vibe. And by the way, we also, it's not just at company primaries. If there are secondary buyers that have been who've come in between rounds, we also give the opportunity to employees to sell then. So if you're able to, which is again maybe not always true, if you're able to offer liquidity and you have a willing buyer, doing that, you know, every six months or something I think is a healthy thing or it relieves the pressure for some people, especially people living the big.”
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
“View their stock as more liquid, I think it's kind of most investors will tell you, most investors say, you know, give them golden handcuffs, force them to stick with you. But I think that, again, that's kind of an antiquated notion. Assuming that there isn't market liquidity, then they can't go elsewhere. So I'd rather be thought of as the startup that lets people sell their vested stock and give them more stock as they continue to do well than sort of treat stock as this sort of like lockup that you can't sell.”
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 have a pretty nonconformist view on secondary, and I think this is going to get me some trouble because most of my investors feel the exact opposite, which is I think that you should let early employees who have vested their stock sell their stock at any point. You shouldn't feel like the vested stock is yours. If they've vested that stock and if they're working at your company, that should be almost as close to compensation, you know, psychologically as cash is. If there is a willing buyer, obviously you want to make sure you don't cause a distraction and your employees are going out and trying to find buyers. But for us, for example, in our series A, we're way oversubscribed. We actually have, we raised our Series A over a year ago and we haven't even started spending it. So we had far more investors who wanted to invest than we had capital to sell them. And so I gave our employees a chance to sell up to 25% of the rested stock. No judgment. Like it wasn't frowned upon. And in my theory, and we'll see if this proves out true or not, my theory is that is more retentive, not less retentive, to give people the opportunity 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
“I operate on a model. If everyone knew what everyone else made, they're like, okay, that generally makes sense. So, you know, for example, we hired somebody, a great software engineer, we thought, wow, actually the market is showing that this person should be 30k more than the other folks on the team. And so not only did we hire her at that price, but we also raised everyone else's salaries to match because we didn't feel like it was appropriate to sort of punish somebody just because they came in earlier, even though somebody else later, the market showed should be paid higher.”
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 generally feel like people should comp better than they think. You know, I think especially startups where you have some semblance of funding, we've been lucky that we've gotten great funding from almost the beginning. So I don't think it's fair to say that you should punish people when it comes to Cash Comp if they join a startup. Obviously, you can't match what some of the highest OpenAI is paying millions of dollars and Google and Microsoft. You can't match that, but you can still pay 75th percentile in terms of cash. And it shouldn't be a huge lifestyle change just because they're joining a startup. I think that's a, you know, 10 years ago, that was this idea that you're exchanging risk for reward and you should punish people when it comes to salary. I feel like if somebody who's great has the choice between working at two startups and one startup gives them a lot of equity and little cash and a lot of equity and a lot of cash, they're going to take the ladder and you want to hire great people, not hire people who are willing to accept, you know, the marginal efficient salary that you can offer them. So that's my philosophy. I also compensate pretty internally fairly.”
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 want to do that. One thing I'll say about titles that I unequivocally believe is that if this is a something that a candidate brings up early or even during the interview process at all, it is a pretty red flag. It shows you kind of what their values are. The best people I've hired are people who've come in with really fancy titles. And the topic of titles didn't even come up. You know, they show up. They could have been CTO or principal. And they show up engineer. No big deal. That is such a positive sign when title is not something they're overly fixated on. And it shows that they care about the problem. They care about the company. They know that if they do well, they'll grow within the company. So that is one thing I think is you can say almost unequivocally, like somebody coming in and this is one of the things that they're sort of focused on. It tells you kind of what their values are and what's meaningful to them.”
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
“You should be dismissive of that concept, and to be a founding engineer is so much more meaningful to somebody. For example, if 80% of your friends are founders of companies and you are just a software engineer, but you started your first employee, psychologically, I think makes it harder. You constantly have this pull. Should I just go? And many of your found friends, by the way, who are co-founders, like, these people, these people are founders? Like, I could do this. And so you mitigate the risk that somebody's going to go off and try to start their own company. You call them that. Yeah, yeah. Well, what do you see as the downside though? What's the downside of calling?”
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 do think titles, they're a bit weird because they're both kind of free to give in one sense that it doesn't cost you more money, but they're expensive in that it creates a sort of like mutually sure destruction. You know, as soon as you give out that first EP title, then everyone wants to be a VP. And that's why I think companies actually go in these ways. We're at early stage everyone's ahead of. You know, you're a head of marketing, head of engineering. You don't have distinction between VP, SVP, and I think that's actually the sweet spot. You kind of want to be in a place where it's clear who is ultimately accountable for a particular function. You don't want just everyone to be in IC. So that's why I kind of like this head of, because it makes it clear, but it also doesn't box you out from one day hiring an executive from the outside and bringing them in and making them, you know, something that maybe they're more accustomed to. The one thing on titles that I do think is important to recognize that at least in some circles, in particular the Bay Area, anything with the word found in it, founding, founder, co-founder has a certain weight that is hard to ignore. Like you're kind of, so I don't think.”
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'd say when you feel market pull, when you feel the market like I gave the example of Starbucks, you know, they're going past all of the processes. They're going past all, like they're seeking forgiveness, not permission to use your product. You're seeing signals that there's more than just a logo. There's a person at that company who feels the pain so viscerally that they've heard about what your product does or they've tried it themselves. And now what a salesperson can do is augment and sort of maximize the potential of that relationship. They're not just cold calling into the Fortune 100, trying to get somebody to pay attention to your Rinky-Dinky startup that, you know, more likely than not, even if they got a meeting, they're going to dismiss because they have no intrinsic interest in what you do.”
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
“Around there's SMBs and the way you go at them is product led growth or at the time it was sort of self service and then there's enterprise the way you go at them is with human beings who like fly up to Seattle and meet with that you know at headquarters and we had this magical thing of getting large enterprises to adopt our product without a human being in the loop and i think we too quickly ran away from that so so it's recognizing that was a core thing working well and then we looked at the numbers and said oh okay like of all our businesses the ones that are retained the best are enterprises so let's go after the enterprises so let's go hire big enterprise sales team like that then that last leap was like two two too naive we should have thought more about what would be the best way to get the fortune 100 companies using our product and i think we could have done that by being true to our core and going after this much larger market”
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 is to understand what's working about your business and what's not. I think we had a core magical thing working at Optimize E from the almost beginning, which was this product-led growth motion, which, by the way, didn't exist. That term was in many ways actually the person who coined that term, use optimization as an example of product-led growth before the term existed. And a good example is, you know, we had on our website, when you go to optimize.com back in 2013, you could put in the website, the URL for any website. You could put it into our homepage. You don't have to sign up, and you could instantly start making changes to the website and seeing what our visual editor looks like. That alone, that was such a magical part of our product that led to not just small businesses, but Starbucks. You know, Starbucks.com, a guy there who's in charge of optimization and conversion for Starbucks.com, had that experience, and he sought forgiveness, not permission to put, you know, to run our product for $79 a month. He put our AB testing product on his homepage. And so Starbucks, that's an enterprise company, but we missed, you know, we had sort of this confusion.”
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 because I couldn't verbalize my intuition, I couldn't even feel like I should defend the path we should be on. I didn't do the job of the CEO to be decisive. And I think those are the biggest lessons I learned, the biggest mistakes I made were not following my gut.”
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 biggest pattern of failures fall into the camp of my gut says we should do A. Somebody else thinks we should do B. We end up doing B and it turned out poorly. There's plenty of times where I said we should do A and it turned out poorly. That wasn't anything I remember. The things that I really stay up at night and, you know, I'm over it now, but it takes a long time to get over your company or things where you're in your bones, in your gut as a founder, you don't feel as the right move or the right focus or the right investment. But by smart people who you've hired, you're bored, it's not because you're being bamboozled. It's people that you've decided that are going to help influence the path. You go with their gut or you go with their decision and it turns out poorly. Many, many examples of this from moving to the enterprise too quickly to sort of not recognizing the core of what we had to sort of abandoning the core problem of solving churn. Like there's all of these things that I time and time again felt in my bones we should do something and I didn't have even the words or even the argument sort of I like to think I'm deeply analytical and data driven but oftentimes it's just my intuition.”
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 when you're in the moment and you are the founder and you are the CEO of the company, that should be your mindset. But, you know, you never know where the company goes. If the company doesn't make it or doesn't become the next, you know, there's like 10 companies that you described. There are going to be huge multi-billion dollar public companies the first time around. Bill Gates, Mark Zuckerberg. It's more likely than not that the company that they've started will fail. And then the second most likely is it's going to have a medium to okay outcome. And so that, and then they decide after that, do they want to start a new company? That's a huge pool of people who I think, you know, they shouldn't be knocked on for whatever reason if their company failed. You know, if it failed because of fraud or whatever, then you shouldn't invest in them. But more likely not, it's some timing to market issues. There's some factors that can explain the failure. I wouldn't, you know, not invest in them. There's just only, you know, yeah, if you can invest in Mark Zuckerberg every time, you should do it. There's just only so many of those out there. And oftentimes you might not even be able to get into that round.”
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
“Absolutely. Yeah, the caliber person that I can hire today is far, far better than the person I could have hired when I started optimizing. So I do think that's a huge factor as well. You can hire much better. And certainly if your first company”
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've referenced. Yeah, oh, absolutely. Yeah. Yeah. Because the other part about the nice thing about second time founders is by the time they decide to be a second time founder, like you kind of already de-risk one of the main things, which is perseverance. I would much rather invest in somebody who's like 100% going to stick with it and try to make it work and maybe 80% is smart than the other way around. There's a lot of people who are smart but end up giving up because it gets hard. And it always gets hard. So when their second I found they're willing to sort of put themselves through that punishment again, that alone is kind of a strong signal to me. And you've learned a lot. Personally, I've learned a lot. I'm much better because of the first company I had.”
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 make their decisions and then they end up leaving. We either part ways amicably or not. And I'm left holding the bag. I'm like, boy, if I'm going to be left holding the bag at the end of this, I better be bought in on the things we do. And some of the biggest mistakes we made are when I sort of abdicated my responsibility there. So, you know, today I try to really be involved where I feel like it has the biggest impact. I'm not all up in everyone's business. I'm up in the business that I think is the highest impact to the company. And that amount of accountability and focus, I think, helps set the example for everyone else, the other managers of a company. knowing this their job to be enough in the details that they can hold people accountable it's a balance you never know and i try to pick the things i think are highest impact but only with hindsight will you know for sure that those are the highest impact things”
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 really made a lot of mistakes in my past around hiring and abdicating responsibility to them. And I think it was the ramp founder recently on the show viewers who talked about this. So you can't abdicate your responsibility to the people you hire. You have to be involved enough to really hold them accountable to understand the details, to probe, to push. And that's something I certainly failed at in many cases my first time around where I hired people who are really great. I mean, that's partly why I hired them. They did 15 years of the job that I had hired them to do. And so how could I, this like 20-something founder who's never been the head of go to market at a huge multi-billion dollar public company, give them advice or hold them accountable. And so that's something I really struggle with the first time. I just didn't even know that was my job. You know, I just sort of thought, get out of the way, be, you know, be the kind of founder that, you know, gives them ownership, autonomy. And what I really learned is that at the end of the day, you as the founder and CEO of the company, you hold it back. Like they're going to be there. Many of the people who joined your company, even if they're great executives, they're just on for a little bit of the ride. I've had several times optimized where they'll join.”
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
“Focus, focus. That's a huge one. I made up for lack of focus when I was a first time founder by just sheer hours. You know, I just worked every waking hour. But now with the beautiful things, I have the benefit of hindsight. I have 10 years I put into my last company and I can recognize it really only three or four things that we did made the difference in the success or failure of the company. At the time, I was doing thousands of things and I thought all of them were important. But in the moment, you can't tell. You don't know what is the key things that help and are going to meaningfully change the outcome versus the things that are just work that feels like it's important. And that ability to focus, that ability to remember that the main thing is that the main thing should say the main thing. That's the thing I think a lot of first-time founders fail. For me, I also had the constraint of having kids, which also forced me that the second type as a founder to really focus on the things that matter because I don't have nearly as much time as I once did as a first time founder. So that's a skill I think a lot of first-time founders can really improve.”
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 core of it is the kind of person that makes a successful founder is usually pretty nonconformist. It's very hard either because the market has pushed them out from traditional jobs and they just can't succeed in a traditional job so they start a company or the entrepreneurship has pulled them in to want to be deeply autonomous and have controller villain destiny. And so it's just very hard. I've actually really struggled with this. I was just talking to my old co-founder from Optimizer getting his advice because he's a YC group partner now, P. Kuman. I don't really know how to give advice to other founders and have it stick. You know, some of my best investors have Jedi Mind tricked me because they've sort of never directly said what they thought. They've sort of influenced me through persuasion. I think this is why a lot of first-time founders make mistakes and don't listen to common wisdom. They're just deeply wired to be nonconformists. And the idea of doing something, the old traditional boring way is kind of maybe unexciting. And that, and there's naivete. So it's a combination of ego, arrogance, nonconformity, and probably naivete all combined. You end up with a lot of founders who, they're not, they're not, you know, getting.”
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 have these tweets that have gone viral where I compare, I say, first time founder X, you know, second time founder Y. And it's usually some painfully true thing that I did when I was a first time founder X and something that sort of insightful, something I've learned, that's Y, a good example. One of them was, you know, first time founders brag about how many employees they have. Second time founders brag about how few employees they have. It's sort of like this deep insight into like how to build a company. And I definitely think there's some truth to that. It's surprising to me how many, despite all of this great content out there and Y Combinator and all this trying to help for some founders, they all kind of make the same class of mistakes over and over again without really internalizing the learned wisdoms. Another way to put it is...”
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 think that's totally true. And I see experiments as kind of Pareto optimal or 80-20. Like you've got all your most juicy, exciting hypotheses. And if those aren't working, you can always come up with new things to try. But it's almost always going to be like if the last five things haven't worked, like is that new sixth thing going to be the key to success sometimes, but almost always if you're naturally going to try the things you're most optimistic and bullish about. But at some point, it's not so much that you don't have the experiments. It's like you're starting to ask yourself, is this even worth trying? Is there any remote chance that what I'm going to try next is even going to make a difference?”
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 other one was recently I saw Dalton Caldwell ask this question the YC group partner and he said a good pivot feels like coming home and that is something I've definitely resonated with every time I've Pivoted or changed idea or adjusted kind of what our focus is.”
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
“Best advice I give is advice I've gotten. So there's two things I've heard on this topic. One was an early investor in optimizing and actually a coworker of mine back at Google, Alad Gill, who's now a very successful investor of himself. I once sought his advice on this exact question. He told me pretty bluntly, he said, things that work tend to work really fast. You know, it was kind of this anti-pattern. Most people would say, well, you got to stick it out and be perseverant and, you know, keep banging your head against an idea. And if you keep executing it. But if you don't even see glimmers of hope, it doesn't have to completely be working. You have to see some version of a glimmer of hope in the thing that you're doing. Even some of the stories like Airbnb that people thought of is this, like it's took for years and years and perseverance. There were glimmers of hope very, very early on that the idea was really powerful. That was very eye-opening to me. And you can kind of see, okay, yeah, if we've been at it for six months and you don't see a lot of the glimmers of hope, then maybe it's time to pivot.”
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 that's largely true, and I find when I heard that, I think what I think about is, you know, I've had lots of pivots in my startups. Everything I pivoted away from almost always could have worked. You know, it's not so much that it's the unequivocal, at least in my mind, maybe this is my delusional, optimistic founder mind. I never thought to myself, oh my gosh, this would never work. It was always a version of if you draw the analogy like climbing a mountain, if you're starting a startup at the base of the mountain and as you climb the mountain, you see other paths to the top that seem a little bit easier and a little bit better. And you've learned a lot along the trip, you're like, oh, I'll go down a little bit to go back up that path. It's not to say your current path you couldn't get to the top of the mountain. You know, eventually you'll get there. It's just going to be much harder. So in that sense, I think it also goes to this idea that ideas are cheap. It's all about execution. So I do think almost any idea can work with enough perseverance, rarely, very rarely is it just fundamentally broken as an idea.”
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 I'm a big believer in technology's ability to do things that were thought of as impossible before. I'm very motivated when somebody has a cynical or pessimistic view on what technology can do. And there's nothing more motivating to me than hearing that and then trying to prove them wrong by showing them by building the demo, by building the product, by building the feature to prove that that is something that technology can do. And in some ways, every version of every startup I've ever done, there's some seed of that idea that's that no, that that's not possible that motivated me to persevere.”
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 first yes was about eight years ago when my now wife said yes to getting married. Any other yes have gotten from venture capitalists or employees or kind of pales in comparison to that big yes. And then no's, there's one pattern of no's I've gotten that now my team knows is the most motivating no I get, which is the version of a no that starts with no, that's not possible.”
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 would have been very astute to notice that I was very into computers. So from a very early age, we always had a computer around. And I owe my mom's boss. She was working as a secretary at Stanford. And her boss was Professor Hector Garcia Molina. And he had this amazing generosity where every time he would buy himself a new computer for home, he'd always have my mom buy the same one for herself and then me and my twin brother actually got to play with it a lot. So we'd always have the latest and greatest thing at home because of his generosity. And that, I think, propelled me to what I'm doing today because I'm into computers, which is something I've been doing ever since I was 10 and even maybe younger.”
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