Startup Founder

“Don't try to build 10 things and see what sticks, because none of them are going to stick. Surprise! None of them are going to magically take off, and you're not going to learn anything if one of them does.”

“Because at the end of the day, we're going to end up pivoting. Find me one startup founder who hasn't pivoted. It just isn't real.”

“I am more often disappointed right now that founders are being, like, less ambitious than they could be.”

“And so long as you're able to confront the reality, so long as you are able to learn the technology itself actually doesn't matter.”

“We've seen it so many times where somebody gets to the penthouse, and they're like, oh, I want to do a new thing. But they don't want to go all the way down to the ground floor, and start at the bottom, fucking putting the building together. Okay, now you're i…”

“So all these stories, when you look at them, because they are, you know, real life choices, frameworks that are being made in real time within Ramayana, you can see them, you know, and apply them equally well in the modern day world. And that's what a startup …”

“And when you look at a startup founder's life, especially early stage startups, they need to have this, you know. So, Hanuman is the character that they should follow, because they go through many, you know, ups and downs, and many down might say that, We have…”

“You don't have to be right all the time. You can be right 60% of the time. And be pretty well off.”

“Should I go there? And the answer is the same now as it always is. Yes, you should. You can go there for a bit and then come back, but you should at least go.”

“So if you just rely on your experience from 10 years ago, even though you may have been successful, I think that's actually makes you like really dangerous because now you're like credible and wrong. It's one thing when you're just wrong and you don't have cre…”

“That's actually the number one reason we see founders not selling is being unrealistic on valuation”

“A lot of people think it's risky and the best way to de-risk it is for them to see your progress.”

“If you want to make sure that you have the right founder, you ask tough questions in the interview process. Right? And you sometimes, ah, ask questions where it might be irritating to them, and then you see how they react to it. Right. And then you get a sense…”

“I'll see someone with their very first liquidity, the very, very first liquidity, they take it and instead of doing something a little bit safe in case there's a rainy day, they turn around and they go put it in a bunch of like very early stage startups. Often…”

“If that's the goal, we try to keep the portfolio actually more liquid because their hope is that they can finance more of it themselves, right? The idea is, well, I did my first company and by IPO I owned 15% of it. The next time I want to own 30% of it, right…”

“A lot of founders, though I think want to stick with their company very, very long term. They're not necessarily thinking, you know, two years out, I'm done. they want to stay along. I mean, this is their baby. They know it. They've grown it. So it's not nece…”

“Probably a lot. It's a very, when it comes to securities and capital raising or raising capital in relation to securities, it's a very easy rule to violate.”

“And one tip for founders is from a hygiene perspective, but also just a way to make it a non-emotional discussion is pre-schedule once or twice a year, the board meeting where you talk about exits.”

“No matter how hard you try, if you have picked the wrong market, if you have built the wrong product, There's no amount of hard work that's going to change the fact that the market doesn't want what you have.”

“People are conditioned by the messaging around startups to believe that if you only persist, that if you only work hard enough, you will find success. And that is just obviously not true. If you look in the rearview mirror, if you look at the data, many, many,…”

“Don't do the income statement if there is work to do over here on the product, because you can always clean the income statement up later, but the minute you leave a crack for a competitor to come in and steal your lunch is gone. And you just have to have that…”

“The thing that most startup founders, in my opinion miss when they think about fundraising and private companies is that at the end of the day, everything converters to public markets.”

“I mean, all it'll do is just obviously going to drive the wealthiest people out, obviously drive the startup founders who want to get wealthy out, because why would you start here? And literally, like you know, strangle the golden goose of California.”

“If you are hung up on the valuation in the bid need and you're spending six months a year to raise money, you're being foolish. You're being left behind. You could double, triple value if you took the money and started to build this stuff.”

“I worry that the, that it just makes sense to leave after the Series B. You should just leave. And I don't, I, and I think YC will get their seven percent, and the funds will still stay, but you'll just leave.”

“Like, you shouldn't have a Rolex, right? It's like very classless, if that makes sense, to like show up as a startup founder with a Rolex, right?”

“So what they do is they hire for tomorrow, not today, and if you do that, you'll never get to tomorrow. So you hire a guy for the job that you have today.”

“I tell all founders to sell. That's my advice.”

“There are some problems you shouldn't fight against. You should just surrender to those problems. You should become humble in front of those problems. And those problems don't affect you. Right. We want to fight against every problem. We want to solve every pr…”

“What works one day will not work the second day. Every day you need a new strategy to fight against your enemy. Some enemies you fight, some enemies you surrender to. And that's how we win the modern battles of life.”

“The highest status thing you could do because I get access to people that the startup found to raise a hundred million dollars. Couldn't, they wouldn't even talk to them. Like I get access to the craziest people in the world because they benefit from my work.”

“The problem is that it kind of has to come from within, meaning like it kind of has to be a habit that you've had that you can then carry on to founding a company because like the amount of demand on your time, it's like a pie eating contest and the prize is j…”

“This is why I tell founders to take their exits and then say no, because they can go bigger, but by default, take it.”

“As you pitch your company, you should make sure that you know which of those four you're pitching, probably pitching one or two of them, and they might also vary depending on the candidate that you're speaking to.”

“I believe at least 50% of founders massage the data and the numbers before they come to the investor.”

“If you have a lot of time to think about this question, it's probably too early. If this is something that comes to mind every day for you, it's probably too early because It's the right time to hire when, like, things are so busy that you can't even find a sl…”

“That was the first time an entire generation of founders heard, you might not raise more capital. You better go learn this crazy idea of how to have more cash coming to your business each month than go out. I imagine you were on the receiving end of a few of t…”

“We say freshmen and seniors make all the money in, in the venture business, like in the entrepreneur business. So you either don't know the rules. So you go into your business and you break a bunch of rules without knowing, or you know all the rules and you bu…”

“I will regularly talk to three, five, ten-person startup founders that, that self-report they might be getting somewhere on the order of, like, three to five to 10 X productivity improvements.”

“When you were bringing on some early investors, many of them want you to continue to be eating on a ramen budget, you know, until they get paid.”

“What you're doing you know, in each of these new environments at each of these customer sites, Is a little bit like being a startup founder, but you're a startup founder where you have access to some very powerful piece of product leverage that makes your job …”

“The biggest power users that where we get most of our revenue are actually startup founders.”

“And that's part of the reason why I think a lot of startup founders in particular could benefit from a little bit of identity diversification. If your entire identity and self-worth is wrapped up in your company, there are too many factors outside of your cont…”

“I think the two biggest issues I see with people is firstly, they don't recognize that the role has changed. They think that what got them here will get them there, right? That they can keep doing the job the way they did it when it was just them and a co-foun…”

“The best founders that I have watched up close throughout my career have all been more like the sort of quick learning and adapting style.”

“An investor's incentive is to get you to burn money because they believe it'll help you grow faster. And if it grows faster that you can always raise more money and burn more money and they can put more money in. So for you to burn, So they can deploy more cap…”

“One of the best, you know, mechanisms I've found is Just pause, take a breath, and the beauty of this is it also gives you an opportunity to listen. That pause, when somebody has a question, you don't have to interrupt them, you don't have to continue the flow…”

“And if you are a founder and you're not out there just like representing yourself and your company every day, you're, or as much as possible, you're doing it wrong. And so you still need to charge money. But I think the best founders I know, even if they're no…”

“The smartest play, if you can possibly pull it off today, is to go make five or ten million, cash out, and just chill. Because you can't predict where it's gonna go. Like, this is, the world's gonna, like, whatever you could do to liquidate your assets now, th…”

“Sometimes I feel it's much more important to, I think trade some amount for relationships over there, because it's not the only time when you're going to work with each other, but I think there will be multiple occasions where you're going to work with each ot…”

“And so I think we had two or three years where the average founder just wasn't that great, right, on a relative basis to history.”

“If you're a startup founder, and suddenly some, you know, people have heard of you, and people try to add you as a scout. Like, people kill their startups all the time by that, just by taking their eye off the ball.”

“To be a startup founder, and to build a business to 10 K a month, a hundred K a month, 500 K a month, you don't need to be the best in the world. You're not competing against everyone else trying to do it, where there's only one winner, like being a heavyweigh…”

“Just take them outside their comfort zone, take them to an escape room, take them to, I don't know, a meditation, something that they're not really used to and just see how they are as a human being.”

“When you're a startup founder, you really have to think about what's important to you, what you're willing to tolerate, what is a good outcome in your opinion. My suggestion is to not factor in financials into what a good outcome looks like.”

“And I think I think a lot of founders, a lot of times are not as transparent because they don't want to feel like they didn't do good or they're failing.”

“If you made money online in high school, I honestly can't think of an exception to have someone who's done that and has not ended up being like, Quite a successful founder in one way or another.”

“I always think every founder has one, maybe two superpowers.”

“It's 30% can be diagnosed with clinical depression. 30% can be diagnosed with ADHD. It's about 29% can be diagnosed with, like, problematic anxiety to, like, where a clinician would diagnose you with it. And there's some overlap that still ends up being, like,…”

“I've seen posts on LinkedIn from startup founders that maybe don't have a background in coding and they're basically advocating for removing the code review check because they say, well, look, I just generated this whole program and I submitted it to my team a…”