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The Twenty Minute VC (20VC) Podcast Episode Notes
Episode Overview Title: 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 Host: Harry Stebbings Guest: Dan Siroker, CEO @ Limitless Release Date: [Specify Date] Listen: [Link to the Episode](https://www.20vc.com)
Episode Summary Dan Siroker shares his unique insights and experiences from his entrepreneurial journey, highlighting effective fundraising strategies, the importance of serial entrepreneurship, and the differences in hiring practices. This episode emphasizes the evolving landscape of venture capital and the significance of problem-centric approaches in startups.
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Key Topics Discussed
- Investing in Serial Entrepreneurs
- Rationale for Preference: Dan prefers investing in serial entrepreneurs due to their:
- Experience in team building.
- Strategic focus and prioritization.
- Ability to pivot when necessary based on past lessons.
- Advice on Pivoting: Insights from industry figures (e.g., Elad Gil, Dalton Caldwell) suggest that successful pivots feel like "coming home," indicating a return to core competencies.
- Fundraising Strategies and Insights
- Fundraising Approach:
- Always be in fundraising mode or not at all.
- Valuation Discussion: When asked about the amount being raised, founders should sidestep direct answers to maintain negotiating power.
- Create urgency in fundraising rounds but avoid the pressure to secure the highest price, which Dan argues can be detrimental.
- Engaging with Associates vs. Decision-Makers:
- Engaging with associates can be beneficial for practice and refining pitches but should not replace meetings with decision-makers.
- Best Practices for Raising Funds:
- Set clear timelines for meetings with potential investors.
- Leverage narratives and transparency to maintain investor interest.
- Hiring Practices
- Why Avoid Hiring Recent Graduates: Dan believes hiring seasoned professionals enhances team effectiveness and prevents unnecessary bloating of the company.
- Titles and Compensation: He warns against giving out titles too easily, which can lead to internal tensions and misalignments.
- Lessons from Optimizely
- Biggest Mistakes: Dan reflects on significant errors, such as moving to enterprise too quickly and not following his instincts, which often led to successful outcomes.
- Feature Creep: The risk of expanding product features without clear demand can dilute focus; simplicity in product design is essential.
- The Role of Technology and AI in Startups
- Focus on Problem-Solving: Successful startups are led by founders who are passionate about addressing specific problems rather than chasing technology trends.
- Market Perception: Dan emphasizes the need to understand shifts in market sentiment towards technology and how that affects entrepreneurial ventures.
- Personal Insights and Future Vision
- Fatherhood's Impact: Dan shares how becoming a father has changed his perspective on work and life balance, emphasizing the importance of focus on family and career.
- Outlook for Limitless in 2034: Dan envisions a future where Limitless seamlessly integrates into everyday life, with millions of users embracing the technology for personal enhancement.
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Key Takeaways
- Serial entrepreneurs are often more investable due to their accumulated experience and ability to adapt.
- Fundraising is a strategic game; understanding investor psychology is crucial.
- Hiring experienced professionals can lead to better decision-making and company performance.
- A focus on simplicity and problem-solving can drive product success and market acceptance.
- Personal experiences, such as parenthood, can provide invaluable insights into managing work and life.
Final Thoughts Dan Siroker’s insights provide a rich framework for understanding the intersection of venture capital, entrepreneurship, and personal growth. His experiences highlight the need for resilience, strategic thinking, and an unwavering focus on solving real-world problems.
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For more resources, show notes, and episodes, visit [The Twenty Minute VC](http://www.20vc.com).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00I very much believe you should either be in fundraising mode or not. The always thing the highest price is almost certainly going to be a mistake. When an investor asks, how much are you raising? More often than not, they're actually asking how much do you think you're worth? And let me, let's start the negotiation on valuation right now because 20 % is what they want. If you say, you know, we're worth, I mean, we're raising 10 million. They just take 10 million divided by point two. And then that's what they think that you think your valuation is. This is 20 VC with me, Harry Stubbings. And I think this is the most tactical show that we've ever done on fundraising.
0:29This show happened, after me and this guest disagreed on funding around dilution amounts on Twitter, how nerdy can you get. And I'm so glad we did, because this is one of the best shows we've done on fundraising. So I'm thrilled to welcome Dan Siroka, co -founder and CEO Limitless. For his latest funding round, Dan took a really unusual approach, resulting in a thousand preliminary offers, with valuations as high as a billion dollars, and resulting in him taking a $350 million dollars series evaluation. Now prior to founding Limitless, Dan was the founder of Optimizely, scaling the company to a 120 million an era, and raising from some of the best, including Peter Fanton at Banshmock, who led the series A.
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3:40Thank you for feeling as mutual, been a bit of a big admirer of the show and glad to be on it. Now, I think Grey lunchpreneurs are shaped by their early years, and so I just love to go back. When you think about how your parents or how your teachers would have described, the 10 -year -old Dan, what do you think they would have said? They would have been very astute to notice that as very into computers. So, for 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.
4:13Where 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, 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. Yeah, along the way we have many great yeses and many hard nose in life. And I find that they shape us to highs and the lows. When you think about a great yes that you think really shaped you.
4:42And also a really shit no. What comes to mind for each before we dive in? Yeah, the first yes with 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 the nose, there's one pattern of nose 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. And I am 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.
5:20And 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 know that that's not possible, that motivated me to persevere. Do you agree with more countries and statement that there's no such thing as a bad idea only a bad time? 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 like unequivocal at least in my mind Maybe this is my delusional optimistic founder mind.
5:58I 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. I'll just 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. Eventually you'll get there, it just can be much harder. So in that sense, I think it also goes to this idea that ideas are cheap.
6:24It'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. I told you beforehand we kind of just go off on Towngents but I am fascinating and we had Daniel Dynes the founder of Uipath on the show It was 10 years to 500k in ARR not exactly hyper grows scaling You've scaled now and you've pivoted many times as you mentioned if I'm a founder come into you asking your advice down on Do I pivot or do I stick? What's the advice that you most often give founders knowing all you do? The best advice I give is it likes I've gotten so there's two two things I've heard on this topic One was an early investor in optimizing, and actually a coworker of my back at Google, a lot Gail who's now a very successful investor of himself.
7:07I once sought his advice on this exact question. He told me pretty bluntly, he said, things that work tend to work really fast. It was kind of this anti -pattern. Most people would say, well, you got to stick it out and be perseverance and 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, the people as a thought of as this, like it took for years and years and perseverance, there were glimmers of hope very, very early on that the idea was really powerful.
7:38That was very eye -opening to me. And you can kind of say, 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. The other one was recently I saw Dalton Caldwell was asked 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. with every time I've pivoted or changed idea or adjusted kind of what our focus is, in many ways, similar to my mountain climbing analogy, it feels like you're on a better path. It feels like you're closer to your core, closer to the problem, closer to being able to solve it and you are kind of on the periphery and now you're in the core.
8:10So that would be my two thoughts of advice. Things that work tend to work really fast and if you're going to pivot, it should feel like you're coming home. I can tell you're not a venture investor, because you should never give attribution for other people's wisdom when you can take it as your own. I always ask you also one question, which is, are there more experiments that you're excited to run and if so what are they? And if not, then it's probably time to pivot. When you've run out of experiments, probably time to change. Yeah, I think that's totally true. I see experiments as kind of Pareto optimal or 80 -20.
8:41You'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, is Is that new six thing gonna be the key to success? Sometimes, but almost always, if you're naturally gonna 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 gonna try next is even gonna make a difference?
9:07When I speak to you now, the thing that's just really striking to me down is just like the experience of starting companies going through the hard yards and finding product market fit, not finding it the pivots, which is why I love to back serial entrepreneurs. and I struggled back first time founders. Just so much mistakes and shit that you don't know that causes costly time. Do you agree with me in the value of serial entrepreneurship? What do you actually say? It's kind of overrated and every time's different. Well, I have these tweets that have gone viral where I compare, I see first time founder X, 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's sort of insightful, something I've learned, that's why.
9:48You could example one of them was first time founders brag about how many employees they have second -hand founders brag about how few employees they have You know, it's sort of like this deep insight into like how to build a company And I definitely think there's some truth to it surprising to me how many despite all of this great content out there and why Commentator and all this trying to help first time founders They all kind of make the same class of mistakes over and over again without really you know internalizing the the learned wisdoms Another way to put it is What is that done? Is that just human ego, humanity?
10:18Is that just humanity of raising too much, hiring too much? I think the core of it is the kind of person that makes a successful founder is usually pretty non -conformist. It's very hard. It's 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 control of real 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 Optimize and getting his advice, because he's a YC group partner in Outpeacumin.
10:47I don't really know how to give advice to other founders and have it stick. Some of my best investors have jet eye -mind tricked me because they've never directly said what they thought. They've influenced me to 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 non -conformist. 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, non -conformity, and probably not even today. All combined, you end up with a lot of founders who they're not going to kill the company usually, but they waste a lot of time and energy on things that ultimately don't matter.
11:22What do you think are the core examples of first time versus Sarah Launchprenate, where it's just very striking the differences? Focus, focus. That's a huge one. I made up for lack of focus when I was the 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've 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 mean if we change the outcome versus the things that are just you know work that feels like it's important and that that ability to focus that ability to Remember that the main thing is the main thing should say the main thing That's the thing I think a lot of first -time founders fail.
12:06For me, I also had the constraint of having kids, which also forced me that. The second time is 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. Okay, the main thing being the main thing and the importance of those two to three things. But, Dan, I did my homework pre -this show. I spoke to so many of your teammates. And they said, one of the things that makes you so special is your ability to get very in the weeds to really be at ground level and know exactly what is going on in each part of the business.
12:38How do you think about the higher, great people and let them do their work and know those two to three things that you should focus on versus being everywhere for everyone? 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 you're as we 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 in my first time around, where I hired people who are really great.
13:08I mean, that's partly why I hired them. They did 15 years of the job that I 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. I just thought, can I be the kind of founder that 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 the bag. They're going to be there.
13:34Many of the people who join your company, even if they're great executives, they're just on for a little bit of the ride. I've had several times optimizably where they'll join, they have their make their decisions, and then they end up leaving, be the part ways, amically or not. And then I'm held, 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 We bought in on the things we do. And some of the biggest mistakes we made are when I sort of advocated my responsibility there. So, you know, today I try to really be involved where I feel like it has the biggest impact.
13:59I'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 the company knowing that it's 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. Before we move on to kind of lessons from optimizing which you kind of touched on now, do you just have to also if you're an investors day, would you have more of a leaning towards backing zero entrepreneurs over first -time founders as a preference?
14:31Yeah, 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 rather invest in somebody who's like a hundred percent going to stick with it and try to make it work and maybe 80 % of smart than the other way around. There's 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 they're technically found they're willing to sort of put themselves through the punishment again, that alone is kind of a strong signal to me, and you've learned a lot.
15:01Personally, I've learned a lot. I'm much better because of the first company I have. I also think clock speed is so important going from zero to one. And as part of clock speed, that is something the best team to take you from zero to one. And as the zero launch player, your network is so much better, more refined than a first time founder who's hiring friends, and kind of anyone who can join at that stage. Absolutely, yeah, the caliber person that I can hire today is far, far better than the person I could have hired, you know, when I started optimising. So I do think that's a huge factor as well.
15:27You can hire much better. And certainly if you're first company did okay, did well, you sold it. That also I think helps a lot when, you know, employee thinks I joined this person. They had a good, they had a, you know, they'd done one good thing, maybe we'll do another. On the flip side though, just help me out on this. I never like it when a founder is like, I have, next company, I'd do this. I'm like, no, no, no, no. The great founders of all time have one company. It is their mission. Daniel Acquitt Spotify, you name these great founders that we have the Colossans that strive. This is the unwavering mission of their life.
15:57Is that wrong of me to expect it to be the founder's life mission? 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 never know where the company goes. If the company doesn't make it or doesn't become the next, there's like 10 companies that just you described that 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 gonna have a medium to okay outcome.
16:23And so that, and then they decide after that till they wanna start a new company, that's a huge pool of people who I think, they shouldn't be knocked on for whatever reason if the company failed. You know, if it failed because of fraud or whatever, then you shouldn't invest in them. But more likely than not, it's some timing to market issues. There's some factors that can explain the failure. I wouldn't not invest in them. There's just only, 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.
16:49So we're going to get on to rounds because I think we have some differences of opinion here which I'm really looking forward to to be fair. I do just have to ask, we mentioned kind of mistakes and lessons. I think like the best thing in podcast honestly is when someone shares mistakes and attaches lessons to them. When you think about optimising, you scale it to a 120 million in ARR. What are the biggest fuck ups that you made in your leadership that you have not taken with you to optimize to limitless. 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.
17:26There'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 just stay up at night, and I've been, I'm over it now, but it takes a long time to get over your company, or things where you're in your bones and 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, your board, you know, this is not because you're being bamboozled. There'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.
17:52Many, many examples of this, you know, 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 like I, I, 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 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 were the biggest lessons I learned, the biggest mistakes I made were not following my gut.
18:26My question to you there is so many founders made the mistake of moving to enterprise too quickly, thinking that it's the holy grail. Having had that experience, what are your biggest piece of advice to founders on when to move into enterprise and when to stay at the core? 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 used Optimize E as an example of product led growth before the term existed.
18:56And, you know, a good example is, you know, we had on our website when you go to Optimize E .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. Starbucks .com, like I there, who's in charge of optimization and conversion for Starbucks .com, have that experience and he's not forgiven. It's not permission to put, you know, to run our product for $79 a month.
19:26He put our A .B. testing product on his homepage. And so Starbucks, that's an enterprise company, but we missed, you know, we had sort of this confusion around there's SMBs and the way you go at them is product -like growth or the time 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 the 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 it's recognizing that was a core thing working well.
19:55And 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 out for the enterprises. So let's go higher, big enterprise sales team. Like that last leap was like two to 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. So if I'm a founder, asking you advice is a portfolio founder of yours in your angel portfolio. And I say, how do I know when's the right time?
20:21What advice do you give me? I'll tell you 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 that going past 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 even 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 more likely not even if they got a meeting, they're going to dismiss because they no intrinsic interest in what you do.
20:59I find one thing that early founders often make mistakes when I say give titles out too easily. Oh, you're a CPO, a head of sales, a dirt, and actually titles are quite expensive in my experience. Do you agree with me on the challenge of giving away titles too easily? What have been some lessons for you there? And I got a shitload of hate, by the way, this weekend, because I said, can we abolish like founding engineer? You're either a founder or you're an engineer. 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.
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21:34As soon as you give out that first VP title that everyone wants to be VP and that's why I think companies actually go in these ways where early stage everyone's ahead of, you know, your 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 particular function. You don't want just everyone to be an IC. So that's why I kind 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, something that maybe they're more accustomed to.
22:06The 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 you should be dismissive of that concept 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 like that just secondologically I think makes it hard you constantly have this pull should I just go and many of your found friends by the who are co -founders Like these people these people are routers like I could do this and so you mitigate the risk that somebody's gonna Go off and try to start their own company.
22:43You call them that as well. You have an employee number one employee number two And people take real pride in the fact that they're employee number four at ramp or at great company I see like founding marketer. They were employee number 26. Yeah, yeah. Well, what would you see as the downside that what's the downside of calling them a founding marketer? It loses the meaning that is quite rightly deserved to founders to the founding team. It kind of cheapens it and then I think it makes it more difficult to layer. If you have a Bunny of a junior marketer being a founding marketer and then we want to bring in a killer It's just going to be really difficult.
23:18They're going to be like, so I'm kind of under the founding marketer who is clearly not at the same level as me. I know. That's right. One thing I'll say about titles that I unequivocally believe is that if this is 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 have hired or 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, you know, CTO or principal or they show up. I'm just off an engineer.
23:45No big deal. That is such a positive sign when title is not something that are 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 there's sort of folks on. It tells you kind of what their values are and what's meaningful to them. Any lessons on comp in the hiring process? I generally feel like people should comp better than they think. I think especially startups where you have some semblance of funding.
24:13We've been lucky that we've gotten great funding for 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 company opening eyes, paying millions of dollars in Google, 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 10 years ago. That was this idea that you're exchanging risk for reward, and you should punish people when it comes to salary.
24:42I feel like if somebody who's great has a 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 gonna 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. Like I operate on the model of everyone knew what everyone else made. They're like, okay, that generally makes sense. So, you know, for example, you know, we hired somebody a great software engineer.
25:09We 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. Okay, it's really challenging in one pivotal moment when secondaries become available now, more so than ever for early team members. And obviously, it's important that people get the right to do it in a lot of cases.
25:38Any lessons on how to do that the right way, how to not lose motivation incentive when suddenly people have got $5 million from their already stock. I have a pretty non -conformance 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 psychologically as cashes.
26:12If 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 over -subscribed. 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 rest of the 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 attentive, not less attentive, to give people the opportunity to view their stock as more liquid.
26:45I think it's kind of most investors would tell you, most investors say, give them gold and 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, 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 treat stock as this sort of like lock up that you can't sell. I like that idea, but I was chatting to a founder of Random Mind who was in this position He was like the challenges it creates a tale of two cities Which is the new employees who have unvested and the older who have vested and suddenly there's like the rich people in the team Who've got not rich, but you know have sold and have more liquid cash and those who are coming in with less liquid cash It kind of creates this old versus new vibe.
27:31Do you worry about that? And not as much as that is a possibility. We don't have that now We also tend to hire more senior people. 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 them. So if you're able to, which is again, maybe not always true, if you're able to offer liquidity, you have a willing buyer, doing that every six months or something, I think is a healthy thing, or it relieves the pressure for some people, especially people living in the Bay area.
28:09And there's something about that ability to provide that liquidity. You know, 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 attentive power that is very hard to do any other way. So I think it's worth it. Why didn't you hire people out of college? 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 has an opportunity cost and you've got n -square connections between people, if given a spot, you could hire somebody to start out a college for less money or somebody who has five or 10 years of experience, I would rather spend more to hire the more experienced person and keep the team smaller than to re -bloat the team by just filling butts and seats.
28:55With 20 people today, I feel like we're having a greater impact and ship faster than we ever could with 120 people and software engineers at Optimizel. So that's working and I just don't want to mess it up by having a bunch of junior people who kind of, you know, 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 a velocity, which right now is very high. In terms of like the funding that we mentioned there and being well over subscribed, I think we're going to have an interesting chat here because we actually first like engaged on Twitter When I was like a funding round that's at least 10 % available total, bluntly will not result in great investors because you can't get a great investor to be engaged with 7 -8%.
29:40And you disagreed with me on Twitter. Why did you disagree and what experience led to that? This is one of those classic things that investors tell the public and most founders don't know the counter examples. Like, there's a bunch of things that are all in the founders or investors interests that 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 investor, Ben Schmarrer, in Dresden, 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.
30:20And I think minimums is a perfect example of that. Even if you talk to LPs of great funds, and they promise these LPs are a certain set of investment DCs and portfolios. But if you talk to the LPs and say, hey, LP in big, successful venture fund, would you like that fund to either yes invest or no invest in some of the best companies? Let's say the best likely company of the year. And if they say, well, the only way to do that is for less than the target ownership percentage, every LP would say yes. And much rather get 1 % of the next Google than 0 % if that's the constraint. So that's why I disagree because I feel like a lot of founders, They just fall into the pattern of what they think is common wisdom not knowing that there are many exceptions to all of these sort of standard very much investor Favorite terms.
31:01I get you. I think the caveat is is you and I mean that nicely a not blowing smoke up your ass But you scaled a business to 120 million in an era and the first zero to one for limitless has been very Successful and efficient 99 .9 % of founders are not like you and I almost worry that they will listen go to raises with like hey we're doing 10 % dilution and it's like yeah, down's a different story. Paul, are playing as a different story? Well, I appreciate that, but I also did this before I was me. You know, my very first series A, I got benchmarked to agree to, you know, I think it was maybe 8 % or something.
31:37Talk to me about that. I'd love to hear about that. So how did that round happen? You met Pito or you met? Who did you meet? How did it go? Yeah, so this is 2013. Pito is the first person I had met. In fact, there's a very memorable conversation. It was also very competitive. And that's why it led to this, I think, the them willing to sort of flex. And obviously, 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.
32:08And 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 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, the other table, and other side.
32:37And if you find common ground, you're able to 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. So what's your advice to founders on what they should give on versus what they should not give on when it comes to those negotiations? 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?
33:12Like 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 groups is, good for you, you know, out of boy, out of girl. And so you recognize it, even just thinking about what it'd take for that person to be able to do that. I think it's important, because that's how you get somebody to feel like, you know, every negotiation you're compromising and you want them at the end, you know, you gotta work with this person. You know, you don't wanna extract every little, you know, you don't wanna squeeze them dry so that like the day after the term sheet and the after -different doctor sign, there's a whole bunch of resentment from day one.
33:45So I think that's important is recognizing where somebody's coming from and how you can give them some wins. That's different for each stage and every investor and that but it starts with empathy. You got to understand where they're coming from. How do you advise founders on when to be willing to have a board? Often VCs want a board seat? I've been lucky not to have a board for 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 there's the node coach who said something like 80 % at Adventure Capitalist at negative value to startups.
34:14I don't know if that's true, but he's not a lot more venture capitalists than I have. And I've certainly worked with a lot of really, really great venture capitalists. Often the best advisors and the best venture capitalists have had didn't need to be on the board to be helpful. You know, a lot of Gilles 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 that 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 get bigger and bigger and closer to going to 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.
34:48They're showing up once a quarter and you have the context of being the founder, ultimately the board may not have. So I generally think if you're a first -time founder and you've found somebody who is 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. I do just want to ask you know, you're a pro now on fund raises. When you think about running your process. How do you do it step by step? How do you think about structuring it? Can you just walk me through that? Yeah, it's actually interesting.
35:16Like, each fundraise I've done, I think, you know, 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 standup comedian goes to these rinky dinky bars on Wednesday afternoon or ever to learn what works and to stick with what works. And so for me, each time I've raised 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 fundraiser in private, and just go down and meet the five investors everyone's that you should go talk to, and hope they say yes.
35:51Instead, let me just draw an analogy. Why that's so ridiculous? How like 90 % and 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. 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 twenty years, that's a really, really big decision. Now imagine if your job, 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 Santel Road.
36:21You 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 that possibility with social media to do the opposite, it to do what Tinder or any great dating app let you do, which is Castaway Net and see who's a good fit for you. And that's what we did with our last fundraise, which is we castaway net. It started off not really actually as a goal fundraising. It was really trying to build trust with customers around our business and showing them we're going concern.
36:48And the byproduct is, you know, we put our deck out, you can see it's about seven minutes. It kind of went viral, we had a couple of 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 saying, in a road, they were actually on office there. But ultimately I felt like that was the best path. Who did you choose? We chose NEA, which has been a great partner. NEA is a very, the thing I loved about NEA, still love is they've been very long -term orientation. They're often buyers at the IPO, they're not sellers.
37:17So that was the thing that drew me to them. And there's so many things in there, both acts and words that really reinforced this, especially as I talked to references and other founders that took money from. Should you always take the highest price, Dan? No, absolutely not. In fact, always taking the highest price is almost certainly gonna 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 a 22 offers at a billion dollars We turned them down and took 350 so we chose we actually have the history that can share the deck if you want or the graph if you want But if the you know 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 we invited them to be part of an RUV aerol of vehicle to participate even a little bit in the round.
38:04So we got this benefit of great lead investor and this wide net of hundreds of smaller investors who then are sort of evangelists and supporters and to help retweet things when we post launches. So we had kind of the best of both worlds. No, dude, I am joking. I totally understand and agree and I think the biggest challenge is people struggling to scale into enormous and enormous valuations. So I totally agree with you there. You mentioned NEA in that kind of continuous financing pathway that they can do. often found as a told, ah, signalling is really dangerous with these large firms, because if they don't do the next round and they can, as a serial founder, are you like the signaling arguments not true?
38:40Are you like, oh, it's worth thinking about? How do you think about that? 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 in Dries and Horowitz, they invested, they did the seed round, like, why is an injury sent leading this round?
39:10Like, 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 that a firm, if you got a good company or you're doing something well, it's almost impossible not to get at least one person at Adventure firm to love what you do. Your job often is to can get that person armed with the data information and support to convince their partners that it's investment worth making. Yeah, I totally agree. I think one thing that people forget is the craft of sales ,manship, or sales inside a partnership, and you have to get other people along with you in a lot of cases.
39:42So I totally agree there. How do you advise founders on how much they raise and how they say the price? Like should they shoot for a smaller amount that people go over it? There's a cat and mouse game here. How do you advise them? Well, first thing I'll advise you is I want to just demystify one and 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 me let me start the negotiation on valuation right now because like you said earlier, often you know, 10 % or 20 % let's say 20 % is what they want.
40:17If you say, you know, we're worth, I mean, we're raising 10 million, they just take 10 million divided by point two 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, what valuation should we go in?
40:44You 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, I've been doing this for 10 years. 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 also got to recognize that are you raising money?
41:08Yes, 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 the marginal benefits you get from understanding where the investor is coming from. One of the worst things that I've heard from investors and team members is that, oh, they're not raising right now. If you want to make it happen, you can always make around happen if you want to.
41:32So I agree with you. And please, anyone listening, do not take down advice. That was terrible advice. No investor ever wants to hear. We'll let the market decide. It makes our life so much more difficult. How do you think about actually a really challenging thing when you've got one term sheet and then you're kind of waiting for others But they're pressuring you to get an answer But you do want to wait and see what the others say. How do you manage this timing process on term sheets? 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 calendar link for the first meetings.
42:15And 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 nileas, they come, you get into the exact problem 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 is the round going?
42:37I go, oh, this, and I just tell them, like this week, from this date to this is first meetings. I'm having, you know, final partnerships meetings. I have three final partnerships meetings next Monday and then two more of the following Monday. And then they have transparency. The thing is they also don't want to miss out. So it's actually a mutual benefit. They, the investors who haven't given you a term sheet, they want to make sure they're not too late to the game. And then you just set expectations with everyone that like that's your calendar and I'm going to make a decision by X date. Then they work backwards from that.
43:00So 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 term sheet 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 gonna help them So you should just work backwards and try to avoid it Do you not feel that with the transactionalization of the process you lose the ability to get data on what that like is a true partner If you're just I think there's definitely some truth to that, but I also think the The opposite like when somebody when investor and usually some associate reaches out and says hey, we really love your business We love to catch up But that's them kind of being transactional too.
43:37That'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 pre -empt 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. 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 funded in the last five years.
44:09And 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, just to just reach out. And I got this great conversation to talk to 12 amazing people. I talk to every single one of his references. And that's how you can really get to know somebody. The cell 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 the afterwards.
44:34Should founders always be raising Marxistus says about lines not dots and building that relationship over time, but then it does take time away from running the core business. Lines not dots or... 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 monthly link for my investor week. It was a week somewhere, usually it was like once, I didn't think of the time I was doing it, maybe once a quarter.
45:06Now I do it once every two quarters where I just, but I do back to back, usually associate meetings where you 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 your investor mode. So you can get out of product mode or customer mode. You're not kind of distracted a long way. and you can really, really hone a pitch. When you have like 30 back -to -back associate and investor meetings, or you're practicing your pitch and tweaking the deck every single meeting, by the end of that, you have this really, really honed product, like a standard commuting practice had earlier.
45:37I totally agree with that in terms of the constant AB testing and really measuring what works and what doesn't. Should founders engage with the associate level and how does that vary? Yes, I mean, I'll say yes, but I'll say yes in a way that's probably reinforcing the part of the Twitter first that think associates don't have much 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'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.
46:14And the same way that Chris Rock will go down to New Jersey, the dive bar, and if you can nail your craft there with a 20 minute disengage associated who doesn't really understand your business, you can really nail it with the people who understand your business. You know, I know others disagree. Some people think, you know, I think Keith Roboss 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.
46:39You've heard a lot of the objections ahead of time. For me, my secret is, I probably shouldn't get 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, oh, well, what about Apple? how you can compete with Apple. And so 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.
47:04You're not just winging it. So that's another reason I meet with associates is to build up my appendix. I so agree with you. And I think the FAQs is a brilliant way to show getting ahead of time on that concerns and actually alming them with the internal material to sell it to that partnership. That's exactly right. That's exactly right. Oftentimes, especially I found this too, when you very quickly can tell the person you're meeting with, they just, they have an inclination, they want to invest, almost from the beginning, and all of their questions, you'll find out, I think, are often the questions they think their partners are the senior partner and their firm will ask them.
47:34So they just want free, give me some ammo so that when my senior partner comes back to me and say, hey, hold on, how is this differentiated in AI? And isn't this commoditizing? 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 done their homework for them. And that's, when 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 question, it's not because of their interest, but because they're about to go sell their partners, that's a good sign.
47:57I'm not being a dick, but I guess I am being a dick, but I guess at this stage, you know, I don't really wanna work with someone who's gotta go up and sell it to someone else. Like, Fenton does not have to sell a deal. I mean, like, he will present it in the way that optimizes liars and people will see the brilliance, but he's not like selling in the way that we talk about that. My thing though, 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 not not gonna be ages But you want somebody before they've had their first IPO and you want them to be the person who's going to have it 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 got to work with amazing investors I had a ton of success like Peter Fenton and Mark and Dreson like they've had a lot of success like for you to truly be the difference in their career or not is pretty unlikely.
48:50And 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 the same way that you'd rather get, you know, an NBA player, you know, 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're aligned around trying to build something with you, not because you're just a fancy logo on there, you know, many logos of public companies they've taken. How do investors differ pre -success on the arc versus post -success when their legends?
49:21The thing I noticed is, well, there's some investors who just out of competitiveists, 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, you know, IRR impact to their fund. And so there's a certain set of investors in that camp. There's others who, you know, I'll be honest, you know, at some point it was clear that optimizely was gonna be okay You know, 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 you know minimum necessary.
49:56I'll show up to the board meetings I'll do the work I need to but I'm not gonna 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 is a 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 that's a darling effect. But then quickly, you know, as if they're being highly rational economic investors, they're gonna allocate their time proportionally to the 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.
50:21But you also got to understand like, it's a business, their 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've got some help along the way, great. But like your job as a founder is to make it succeed. And so playing the victim and assuming your vestors the reason you're going to succeed or not, I think is a is lying yourself and lying to your investors.
50:49Can I see you've had some of the best brands, banish mark, your Andreasons of the world. To what extent does venture brand being behind you make a large difference to company trajectory or not? I think it helps. It doesn't it's not the difference maker. I think it helps with recruiting. Great, great talent can work anywhere. and if they had 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 may be marginally helps with customers. I don't think so.
51:19If 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 bennisside unintended bennisside 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. First of all, we got hundreds of investors. So now 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 -lighted everyone is how are you gonna compete with limitless, you know, how are you gonna compete with us, especially given, you know, all of the, the who's who's invested.
51:55So that probably helps. Maybe I don't, 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. Do you think there's any big misalignments between venture investors and founders that aren't cool down enough? At every stage, up until the very end, they're pretty well aligned. 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 a multi -billion dollar public company.
52:24Or actually, I think more likely than not, they're discounting 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. 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, they're basically, for example, I'll just make a very plain.
52:52If 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, makes no difference to the investors. They basically get 1x back. So in those situations, you really got to be thoughtful around how you want to raise and also how you structure that. Never take more than 1x non -participating, preferred liquidation preference. That's when things get really out of alignment. Do you think we're going to enter a world of pain around like prefs? We've seen a lot of people raise a lot of money. I think investors will get that money back in a lot of cases, not all, but everyone else will suffer in a lot of case is to agree and I hope and I need advice.
53:26I 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 two -exlicuation preference, which almost always means no employees are ever going to get any of their stock worth anything. So I do worry about that. But if you are 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.
54:01It is much better for you as the 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 Dirt is now worth less. But that's fine. They'll leave you 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 any big of a mistakes the EC founders make in fundraising. When you look at the founders around, 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, you know, small percent risk that you're going to get screwed over.
54:33This is 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, you know, I should ask him, what do you think now? I do think, when you think control and you think governance, you shouldn't view it as you're a fending investor. like an investor was highly rational, they would also ask for and want as much control as possible if they were the founder. In many former founders who are now investors, understand that they wish they had more control. So things like super voting stock, I think you should make sure to ask for multiple boards, you should ask for not having board members, maybe having board observers instead of board members for certain investors.
55:06It's hard to ask because it kind of can feel a little personal, I think, because like, well, 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. 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 super voting and multiple board seats.
55:33Do you find most investors get in the way? No, I don't. Actually, I think more likely, and 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 my investor update list. We have maybe 300, 200 people. And you know, I'll get, you know, on a good email, maybe 20 responses or like, you know, something, and wherever I ask them to do something. But most people do, they were just one of many companies. So you just got to recognize that like even great investors, you're just one of many. You're two kind there. I respond to everyone.
55:59You can say, Dan, awesome to see the user growth well done. It's five seconds. I actually do the same. I have a few angel versus I do the same, mostly because when I don't get those back, and it's like five seconds for fuck's sake. Do you know what the when -in -to -that update? All right, Harry, I'm gonna add you to my investor update list and I will look forward to just for the just for the Add a boy or a good job or here is how I can help you solve it on honestly, I think it's so important to yes good What was the best venture meeting you've had like when you look back and like oh that one was like my favorite ever across both Companies 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.
56:43He could barely walk. And the reason was he had just been helicopter skiing and he broke his knee or something. We still show up to the meeting. He then, by the way, he thinks he's a similar kind of dynamic with me where he can't sort of prove the world other things. Anyway, he went it 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.
57:11The 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 and 2018. Exactly five years later, it was exactly when I started to feel trapped, resentful, disengaged, going through emotions. And he exactly, astutely, figured it, asked and pointed out. And at the time, 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 to public, they're all founders who have just been persevering, who can keep it up, who stay in love with the business 5, 10, 20, 30 years into it.
57:48And 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 it, but it was really actually trying to understand what motivates me, what drives me. And that's something I've definitely learned with Limitless. I will be at Limitless, this 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. I just have to ask you, as an investor, it's a really freaking hard world to navigate, investing in a world of AI, of such transience of leadership, one week it's Mr.
58:17All, the next week it's Lama, the next week it's Open AI. How do you think about where we are? How do you analyze the landscape today? I know it's broad and shit question, but just help me understand how you think about it and where we are. 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 and searcher problem. I learned this anti -pattern at Google actually. I started my career there as an social product manager, and Google's notorious for building products that are technology and searcher problems.
58:54Google 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 start -up 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 and search -a -ro 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.
59:26It'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 AppLayer or Foundation layer? It shouldn't be first time or second time founder. It's, is this font founder obsessed with a problem in the world? Is a problem real? Are there other people have that problem? Do I have confidence that this founder will persevere to try to solve that problem? And maybe you have some of the skills necessary to use technology to do that? Not, oh cool. It's like, you know, Mistrel's the latest greatness. You know, those things are ephemeral.
59:52I'll focus on problem obsessed founders. How do you think about visibility of problem? And what I mean by that is that everyone's like, Oh, AI customer service, AI sales rep. Probably two of the most prominent kind of use cases that we see. Yes, there's a problem, but everyone else sees it. How do you think about differentiation, competition, and actually if it's a problem that the world sees, is there a lower quality of problem? Yeah, I mean, I think every problem can expand over time. So I don't think you should be so much, is it 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 on Twitter or social media.
1:00:31There's actually something they care about. And the best version of that story is, hey, at my last company, gosh, it was so annoying that we had to do blah. And now, you know what, I started this company to try to solve blah. And it's like some niche thing, I think Coinbase might have been similar. We could, you know, Brian had seen things at Airbnb or, you know, so you want somebody who both first hand saw that problem and maybe felt it themselves. The best CEO for a AI customer agent is somebody who started their career answering customers of or calls You know like that's what you're looking for is this founder market fit around the problem Not somebody who's like a McKinsey consultant who said like if their first light is here's the market map and here's the market size And you know here's the niche we're gonna you know That's very very to me at least and I'm maybe I'm missing out on good companies But to me that's immediate red flag you want somebody who understands the problem and just couldn't sleep at night if this problem wasn't solved.
1:01:18And maybe there's 100 other companies out there. But this one is the one that will succeed, because the founder cares so much about the problem and understands the problem. And let me just give you some empathy for why that's so important. I found when we started optimising, the thing that made it work. And I had two failed startups right before that I can explain. But basically, the thing that clicked for optimising is it was the product I wish I had in the Obama campaign in 2008. And because I had used AB testing from Adobe and from Google, I saw all of the pain points. I saw what was so hard about those products.
1:01:46And it wasn't the lack of features. It was in fact the opposite. What you wanted in the product and the market was something that didn't require developer was what you could see, what you see is what you get. And we did not do a lot of things that McKinsey Consultant said you should do. We didn't have multivariate testing. We didn't have all these things that's like some outsider would have said was necessary. But if you're an insider, if you've done the problem yourself, you know very quickly what matters and what doesn't. And so as a founder coming into a new market, if you've been the person doing customer support calls, you know the problem so much better than an outsider who has it.
1:02:16So that's what I would vote on and that's what who invested. You said there about kind of the features and I think feature creep is one of the most dangerous things. How do you think about simplicity and product today, the importance of it and how to prevent feature creep? This is one of the things that I think the CEO really needs to do 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.
1:02:45You 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, you know, around building features that no good deed goes unpunished.
1:03:15I 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, now there's this edge case we didn't think about it. Oh, then someone wants to do this other thing. So it's like opening a commitment that you don't have to keep peeing. 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? What is the biggest thing that you said no to that you should have said yes to in either company and did it teach you anything?
1:03:42And optimizely, 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 we were sitting at Chipotle and Soma with Spencer. And I, to this day, I'm so impressed with it. I was offering him insane amounts of money. Life -changing for him 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 was associated with that.
1:04:09I should have been more zuck -like and just said, okay, they didn't accept our offer. Let's go just beat with that. We already had the distribution. We had the market, you know, and we could have been amplitude or more in amplitude. It's now a big public company. Another example is segment, another area where it was adjacent to what we're doing. We tried to acquire them. They were later stage 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 finally enough, both of those companies, I thought, oh, it's too late.
1:04:34Ambulance Adoris got this huge lead, you know? So I was too, too, too, I guess, down on myself and maybe two ego -driven to see it had to be my idea. But I think both of those are things I said no to or got said no to that should have said yes. You crush launches. Like when I was looking at the launch for pendant, it was just really well done. Like, well done in the way that like Apple crush launch. Any big lessons for you on what it took, what it takes to do launches well, having done especially pendant so well, so recently. If I had to give you any advice, it just focused 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.
1:05:10That'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's this all thing? How does this help my life? So I can talk to you all day but I am cognizant of time. So we're going to move into a quick far out. So I say a short state when you give me your immediate thoughts. Does that sound okay? Sure, yeah. So why not do YC the second time? I probably should have. I kind of regret not doing it. I think I was maybe too much pride and ego. I didn't need it. YC has a lot of gifts that keep on giving, even if you're a second time founder, like work at a startup, like office hours.
1:05:41So 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. If you would have sought another company and you could add a board member, any board member, who would it be and why? Probably Sam Altman or a lot Gil, two folks who have been very helpful to me, who don't learn or board and probably don't need to who are wants to be, they're two fantastic people who have always had question advice and sort of deep intuition for the market. It has both been honest and candid. That's another thing that you often, I need to remember, somebody who doesn't shy away from saying the hard truth that you need to hear to try to save your ego.
1:06:14So especially a lot of, I very much appreciate that in the past. Okay, you can cool yourself up before your wife has your first child and give yourself some advice knowing all the ENO now about fatherhood. What advice would you give yourself? It is going to be harder than anything you've ever done before. set expectations incredibly low. If you're gonna do this well and focus on what you care about, you're gonna 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. What is so hard? Especially the early days, there's just these tiny little human beings who you have to feed and care for who are never stopping.
1:06:50You 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 there just be too much. And I've also the theory, humans in general, and probably kids in particular, have learned to nap and sleep just to give parents a break because otherwise they 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, you know, like, and I'll be honest, like I've cut out basically, I don't spend much time with friends.
1:07:20I had basically no hobbies. I'm reminded of this Rick Rubin code. 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, it's just a lot. So that's what makes it hard. I think now in hindsight, one was not so hard. Three is about three kids too hard. Would you have a fourth? Well, you know, I'm not ruling that out. I certainly think now is not the time given all the other things on my plate.
1:07:51and I'm just in loving and enjoying. When kids are at this age, 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, is just spending time with you. And that is just so special. To have a five -year -old who all they want to do is just like run around the house with you which those doing yesterday, or letting ladybugs go, or planting things, and that's such a special time. So with another fourth, you then have to split your time a little bit more. So I think we're very happy with things how things are, and it's only getting better.
1:08:17Someone once told me, really appreciate every time your child runs up to you when you come home, because that will never be a last day where they say this will be the last time. For sure. No, I definitely value it. Appreciate that. It also creates a certain level of focus in my life that I didn't have before. I have a purpose, a meaning, and in a way that 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 techy answer, but I love watching how they learn and how they grow, Imagine the parallels to AI and AI and seeing and understanding intelligence and what it means to be human from first principles to witness to see a human being learned 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.
1:09:04What worries you most and what are you most optimistic about in the world that they're going to grow up in in 20 years? What worries me most about the world that grew up in and today, frankly, is humorism. 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 a approach to technology innovation that is cynical. I think there's a time when I started optimizing 2010, where it was cool to be a founder, even in San Francisco, it was cool to be a founder. Then I think after the Google bus protests, it was actually, I think, the movie silicon or social network that actually propelled a lot of people.
1:09:42That brought in a lot of sort of, you know, launchpreneurs, but, you know, you had appeared at a 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 is a counter -movement against technology and against optimism that I think could be really dangerous. And we could go into the dark ages. You know, we have that that's happened once and at least once in the history of society and that I know I think it's you know, I think it's too far down actually known matter what the doomer is and AI is out of the box maybe I don't know I mean governments have control they can do things to And all it takes is one or two bad policies here and there I mean we are not that far off from regulatory capture around AI models that the unfortunate challenges the doomers are on the same side as the regulatory capture and there's a lot of money at stake so So, you know, Dumaurs Plus regulatory capture, I could see creating a world in which a lot of AI innovation is stalled.
1:10:43And 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, you know, if it were true that it was, you know, 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, you know, 1996, even 2000, you could just put up a website and 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.
1:11:09You need hopefully a 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. You know, 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 stop going out of space. And it wasn't until SpaceX came around and new technology was built and entrepreneurs like Elon Musk pushed frountiers 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.
1:11:39But people are 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 zero percent chance that the doomswend. Do you think Tate Talk will be banned? It is likely to have quite a bit of headwind regulatory headwind regulatory wise. And certainly, you know, the bill is past. So they've got a year to sell it. And you know, the rumors are now that, you know, Donald Trump's going come in and make the key part of his platform that he's going to un -ban it, which might actually work for him. So a lot of this posturing and a lot of government intervention here may be more around trying to appease what it takes to get reelected than it is actually making good policy.
1:12:15So I don't know. Final one for you. Next is 10 years for limitless. So it's 2034. What would be successful for you if you were to paint the limitless picture in 2034? It would be millions of users, active users daily. What are 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. What did it 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 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 chop down from a tree called paper, you had a stick with ink at the end of it and you scribble things down.
1:13:14And that's how you remember? That was the thing you thought was the best idea to remember and that people would laugh at that concept. That would be success in 10 years. Down, listen, I've absolutely loved this conversation. Honestly, it is so refreshing to have such honesty and granularity to a discussion. So thanks for being such a great guest and I've loved it. Thank you Harry, it was real pleasure to be on the podcast and really excited to be here. I mean that show is so much fun too, I want to say huge thank you for Dan for being such a great guest. If you want to see the full video on YouTube you can check it out by searching for 20 VC, that's 2 -0 VC on YouTube.
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From the publisher
Dan Siroker is the Co-Founder and CEO @ Limitless, a personalized AI powered by what you’ve seen, said, or heard. For his latest funding round, Dan took an unusual approach resulting in 1,000 preliminary offers with valuations as high as $1BN — and resulted in a $350 million Series A valuation. Prior to founding Limitless, Dan was the Founder of Optimizely, scaling the company to $120M in ARR and raising from some of the best in the business including Peter Fenton @ Benchmark who led the Series A.
In Today's Episode with Dan Siroker We Discuss:
1. Serial Entrepreneurs are More Investable:
- Why would Dan always prefer to invest in serial entrepreneurs than first time founders?
- How do serial entrepreneurs approach team building and size of team differently?
- How do serial entrepreneurs approach focus and prioritisation differently?
- How do serial entrepreneurs approach pivoting differently to first time founders?
- What is Dan's advice from Elad Gil and YC's Dalton Caldwell on when to pivot?
2. The Secret to Fundraising: How to Speak VC
- Should founders always be raising?
- What is the right thing to respond to investors when they reach out to you outside of a round?
- What question are investors really asking when they ask, how much are you raising?
- How should founders approach valuation, what should they say when they are asked for it?
- How can founders create urgency in a funding round? What works? What does not?
3. How to Raise the Best Funding Round:
- Should founders engage with associates or only worth it with decision-makers?
- Why should founders always choose the investor who is on the early arc of their career?
- Why was Dan's first meeting with Peter Fenton the best meeting he has ever had with a VC?
- Why does Dan believe that taking the highest price is never the right answer?
- To what extent does having a true Tier 1 VC lead your round, change the game for your company?
4. Dan Siroker: AMA:
- How did becoming a father change the way that Dan operates?
- Why is Dan scared we might see technological progress stall for the next 20 years?
- Why did Dan not do YC the second time around with Limitless?
- What is the story of how Optimizely nearly bought Amplitude?




