Warren Shaeffer - How to think and act like a venture-backed founder!

Hello everybody. I'm so excited. Thanks for tuning in for this episode, episode 5 of the Undefeated Underdogs podcast. I'm Sharath, your host, and today I have a very special guest. who's a very dear friend of mine, and he's one of the kindest founders I know in my circle. Welcome, Warren Schaefer. Thanks for joining the pod.

Very excited to be here. Thanks for having me, Sharath.

Absolutely. Let me give a brief intro about Warren for folks who don't know him. Warren is a seasoned entrepreneur. He's a 3x founder. He's a dad to 3 kids. which is something I want to discuss later. He's a writer. He's a first-generation immigrant, which I want to cover as well. He built 3 companies and sold to giants like Jiffy and Medium. And he's raised over like, what, $12 million with world-class investors like a16z, Initialized Capital, and more. So His resume speaks for himself and he's one of those founders who just undersell themselves and focus on the mission and the vision of building a company. So I'm actually very excited to talk to you, Awar, and appreciate your time. Thanks for being on the pod.

Thank you so much for the kind introduction, Sharaf. So I'm such a big fan of yours and excited to Excited for everything that you're building and let's jump into it whenever you're ready.

Awesome. Yeah. So, I do have some questions. I want to cover some topics. Let's start with— so last time, so by the way, for folks who are listening, I met Warren in person for the first time a few weeks ago in SF when I was traveling there for business. And one of the things he mentioned when we were chatting was his parents immigrated to the US long before and at a very young age. And I want to dive deeper into that story. Tell me more about how the whole thing went and you transitioned from wherever it is. Is it France, if I'm not wrong?

My parents immigrated from Eastern Europe, from Romania.

Oh, wow.

Yeah, so I was actually born in the States, but they were not. And so I have a lot of empathy for people who are new to the country and who are first generation or whose parents came. Right. And sure, I should clarify, we became friends through Twitter. So we didn't just become fast friends a few weeks ago. Oh, yes. We— the first person I feel like I've become friends with via Twitter.

Oh, yes, yes. Absolutely. Absolutely. It's one of those moments I kind of like, you know, remember for myself, because those who I interact with Twitter, and those who I meet in person, it's very rare that they're actually the same person, either they just like, you know, they're a different personality, but you're one of them. Who exactly? In fact, in fact, as a matter of fact, you actually kind of exceeded my expectations of who you are in real life. So, yeah, I mean, tell me about that, like the story, your childhood, how you got into entrepreneurship, your roots, about your parents and whatnot.

Sure. Yeah. So as I mentioned, my parents left Romania in the '70s when Romania was a communist country and had a pretty notorious dictator at the time. named Ceaușescu, who ended up getting executed. But, but they left before that happened. And when you tried to leave a communist country, you basically couldn't take anything with you. So they left. And my, my father was an electrical engineer. My mom had studied music at a conservatory and was a pianist. And— Right. But ended up on the stage with, with very little. They had— I have an older brother, so they had Their first son born in Romania and ended up in the States. And I think like so many immigrants, they were really eager to assimilate. They really wanted to be part of the American story. And there's so much that resonated about America that was in such stark contrast to communist Romania and many countries that are, you know, still developing, right? Which is this idea that you can— go from, from kind of poor and insecure to, to having your needs met fully in, in one generation. And I'm sure you've got a similar experience of that. And I think that's what makes America great. I mean, it's not without its faults, obviously, but there's the old Churchill quote of democracy is the worst form of government except for all the other ones. I think the US in many ways is the worst country in the world except for all the other ones. Right. And, um, I think that the historical context of gratitude of, you know, being in a place where you can work hard and try to accomplish your goals without having too much authoritarian intervention is something that's definitely stuck with me and I feel grateful for.

No, that's so true. You know, that's why I'm here as well. I moved to the US like 10 years ago chasing the American dream. I'm still chasing. I recently got my O-1 visa, which was given to top 1% folks in startups and tech. What you said is really true, which is, I think if I remember it right, JFK said this, in America, anything is possible. So it's by default an abundant environment by nature, right? Like there are They're incredible people who always try to shoot stars and they try to be ambitious. And that ambitiousness is kind of contagious. And that's why, of course, you have to surround yourselves with those folks. And I see a lot in you, in your journey as well. You kind of lived through the American dream, which is you've kind of built companies from ground up, from scratch. And you sold it to not just like any other brands, but they're like very big, very notable brands like Medium or Jiffy. So tell me about like how was your journey going from 0 to 1 and later then from 1 to N?

So from 0 to 1 in terms of on a company building perspective,

Yeah, on a company building perspective, or like your personal, you know, hiring people, working with like ambitious people, pushing yourselves to make that mark, right? Like, how's that journey look like for you?

Yeah, so let me caveat all this by saying I feel really fortunate and very privileged to be in the position that I was in, right? So I grew up in a very affluent area, even though my parents ended up not having a lot of money when relatively certainly, I got exposed to a lot of people who were very successful. Mm-hmm. And I think that is a really unique and fortunate situation, especially when you're young. I think the internet in many ways democratizes that exposure, which is great and why we're seeing more people leveling up faster over the course of a lifetime. In terms of company building and going from 0 to 1, it's, you know, I remember I went through an accelerator in Los Angeles. I actually worked in finance for a few years after college.

Right.

And that sort of the thing was I had a liberal arts education and I wanted to get some real practical skills. And I think finance is such a great underpinning of every business, right? Because even at the end of the day, no matter how great your product is, you ultimately need to charge money. You need to make it, find a way to make money for your product. So, so I'm grateful that I got to work in finance and also there was a nice paycheck and I was able to pay, pay off my student debt and start, start actually investing at an earlier age too. So, Right. But I left finance and that was actually a really hard decision because at the time, you know, I was well paid and it felt kind of risky. It was, I felt like I was on a very safe path. I was good at finance. I was working for a really prestigious private equity firm. And I thought, well, you know what? Risk is actually subjective. And I felt I had the itch to go start something and I felt that If I didn't leave when I was young, it would be even harder for me to leave down the road. Right. And so it'd almost be a risk to not take the risk of trying something different. Thinking of that regret minimization framework, right? Of how do you make a decision? Well, on your deathbed, if you feel like you might wanna be an entrepreneur and you don't try it, you might regret it.

Yeah.

And so I was able to, you know, take some savings and move down to LA. to be closer to family and fell into an accelerator. And that's— Mm-hmm. I'm so grateful for the accelerator experience because you get put together in a cohort with a lot of other first-time founders. Mm-hmm. And it's just like grad school for thinking about company building. And that accelerator that I went through is called Mucker. Mm-hmm. The guys, 2 individuals started it, Will Su and Eric Granalla. And I'm still close with them and still consider them mentors. So, I learned, you know, thinking about zero-to-one frameworks is first really understand what is a startup today and what's a venture-backed startup versus a bootstrap startup. And if you're going down the venture model, I think accelerators are so powerful for first-time founders. So I'm going to dig in on more of the mechanics of it, but that's some high-level context.

Yeah. So I think I want to dive deeper into one thing which you said about startup versus venture-backed startup, which is having like a venture-backed idea. And I think all 3 of your companies, you raised like $12 million or more from some of the biggest venture funds. How do you differentiate? And you're an investor by yourself, right? And how do you differentiate a venture-backed idea versus like a bootstrapped, say for example, and what are some qualities you see?

Yeah. So generally, venture investors are looking to back companies that can have outsized returns and can ideally return the size of their fund, right? So a quick rule of thumb is you want the, a single investment to be paid, to pay back your entire fund. So if you have a $200 million fund and you get 20% of a company, you need that company to be worth $1 billion post-dilution for you.

Hmm.

assuming you have 20%, right, to basically pay back your entire, your entire fund. So that's why a lot of, a lot of VCs are looking for companies that can be enormous. And this is why they'll often ask you about what's your total addressable market. Is it— if it's not, if your market size isn't above $1 billion, then it's really hard for you to build a business that is worth $1 billion, obviously, right? Right. So that's, you know, venture capital really is specialty financing. It is financing for companies and entrepreneurs who are trying to go build Usually something that is, kind of rule of thumb, $1 billion or more in value. And obviously angel investors have a lower threshold because they have less capital that they're trying to return. Whereas these huge monster funds like Sequoia and Andreessen Horowitz are really looking for those enduring generational companies that are going to drive outside returns, the Facebooks, the Pinterests, the Snapchats of the

world. Right.

And bootstrapping, I think, is amazing. Actually, the first company out of Mucker that I worked on with my co-founder was largely bootstrapped. And, you know, I think that there are real pros and cons to each path. And one isn't— it really is a question of what do you want to learn about as an entrepreneur and where are you in your life cycle?

Yeah, you said this too many times to me personally when I asked for like advice about Hey, what's the path about like going venture? And you said many times like, don't raise money if there is no need. Why is that? Like, why did you feel that way? And what kind of message you want to like, you know, pass on to listeners who are like, either they're on the verge of fundraising or they just want to like, you know, they're just in the dilemma of, hey, I want to bootstrap or I want to like

Yeah, I think a lot of entrepreneurs confuse the means and the end of

fundraising,

right? So what I mean by that is a lot of people think, oh, I need to go raise venture funding because that's what you do. That's a sign of success. And the reality is, is that what you're trying to do is build a company that you're proud of, that gives you a lot of purpose, that adds value to your customers, and that, you know, you're able to derive value from economically, emotionally. Mm-hmm. And all the other ways too, right? So getting really clear as a founder of what you're trying to accomplish is very important. Um, and if you're, if you think, hey, I've got this great idea, but it's a niche business and the market is only $20 million, well, that's clearly, you shouldn't raise venture money for that because that's not gonna be, it's not gonna fit with what a venture capitalist wants to, to invest in ideally, right? And so you wanna, you wanna align your incentives with whoever your backers are. You also lose a lot of control over your company when you take on outside capital, right? So the expectations go up dramatically once you take that first VC check, right? It's, hey, I'm counting on you to try to go build that billion-dollar company. And that's a lot of pressure.

Right.

And it can also lead to making almost irrational Uh, moves, right? You might say, hey, you should be really slow and thoughtful about hiring. And, I mean, we see this now. There's lots of layoffs happening at companies. That's because— That's true. The fuel of venture capital is, you know, the expectation of moving very quickly. Investors want to get big returns as fast as possible. But that's not always right for every business. Some businesses just take longer to mature. Some businesses don't meet the criteria of addressable market. Some founders don't want to have that expectation and they'd rather have a lifestyle business. Those are all legitimate reasons to not take venture capital if you can.

I want to dive a little deeper into the topic of handling pressure, right? Like for people, for founders especially who've raised money, how do you, how did you handle before? when you were at Noble. At many times you kind of were very vocal about it as well on Twitter, sharing like your thoughts and being very transparent about it. You know, I saw many of your threads resonate that, and you're big on habits too. So what are some, any tactics you've gathered over time now that you're like kind of a seasoned entrepreneur? of handling pressure, stress, uh, in general?

Yeah, I think being a founder is often glorified, right? The idea you get to be your own boss and set your own rules and set your own schedule. And right, the reality is every founder I know works extremely hard and feels a lot of existential pressure, especially ones who have taken venture capital and feel that onus of delivering multiples of return on their investors' capital. So one, anybody who's a founder out there, I just want to normalize that it's really stressful and it often feels very lonely too. Mm-hmm. Because there is systemic pressure to be really positive as a founder, right? To say like, things are going awesome and we're crushing it. And it actually creates— it's this prisoner's dilemma problem where everyone would be better off if everyone was just very honest about how they're doing. But because on a personal basis, you feel the motivation to try to get that extra edge, there's pressure to just constantly say things are going great. And I actually think we connected because I posted a tweet after having done layoffs at Noble. So Noble was—

Right.

Raised a seed round from Andreessen Horowitz. And we thought that we had product-market fit very early and we scaled the team to 10 people. And what we realized was we hadn't cracked customer acquisition fast enough. Right. And this is a separate learning, but really thinking about growth for every product and what your strategy is from day one, I think is very important. But I let go of half the team and that was my— I felt terrible and I shared the experience on Twitter because I wanted to share the knowledge that I had learned about doing it and hopefully help at least one other founder kind of avoid the mistake of overhiring because it's disruptive to the company, it's disruptive to the people who are affected, to everybody. So yeah, I think I lost the thread of the question, but—

Yeah, I feel, yeah, so for sure, I feel you, a founder needs to be very responsible, not for themselves, but for others too. And, you know, it's easy to like, I wouldn't say it's easy is the wrong word, but it's actually more feasible to like bring more people, attract great talent and be responsible in terms of vision. And I think some of the founders I see personally do that because they're just like you said, they glorify a lot of things missing the reality and they live in their own bubble hype. and miss the whole point of why they're doing it, right? They miss the purity, sanity, and the clarity of building startups, which is much more larger than anything else. Yeah, you were telling something.

Yeah, well, what I was gonna say was, I actually think that a founder has a responsibility to look after herself or himself. And that is a responsibility that a lot of founders overlook. And the reality is, is that building a company, it's a marathon, right? You're really trying to build an enduring company. Um, and many founders operate at an unsustainable level, right? And I think there's a lot of hustle porn out there that is, is very detrimental to individuals, uh, in the short term and companies in the long term, right? Mm-hmm. Where if a founder doesn't make decisions from a place above the line, you know, if they're not well rested, if they're not thinking clearly, uh, that's, that's harmful not just to themselves, but to their employees and to their investors as well. And so, I, something that I've done, I did, and I wish I would've done earlier in my career as, as a venture-backed founder was hire an executive coach. And historically coaches were kind of a dirty word. It was somebody, you know, you were struggling as an entrepreneur or as an executive, then you would have to get a coach. Your board would say work with a coach. And I think that mentality is thankfully changing, which is people are realizing, well, top athletes have coaches. Right. Yeah. Business people or people who are trying to level up work with an outsider to help them grow. And that's something that I, you know, I got referred to a coach by a friend who's a founder and it's one of the best decisions I made for my career and for my company too.

Right. You've touched on a great point there, which is, you know, it's okay to seek help. you can't do everything by your own. It's, you know, you just have to accept the reality. And a lot of people, either their ego comes in picture or something that stops them to accept the fact that they can't do things alone, you know, and they overburden themselves and burn out many times. Yeah. So I feel that there is a sense of I would say self-awareness, which I see a lot in you personally. You're very self-aware about your situations, your consequences, and you make right decisions. So let me ask you this, like, how did you develop that philosophy or that mindset of making the right moves and being very self-aware, like, where you are, instead of going against basically like fighting against like the norms, right? Like, uh, where'd you get that? Is it, is it from, uh, your parents? Are you adapted somewhere? You read books? Want to know about, uh, your secret.

Yeah, I want to make sure I understand the question. Is it, um, understanding how to think differently from a crowd? Is that what you're getting at?

I think it's more about like How did you develop that self-awareness as a muscle? A lot many people, let's take Tik as an example, right? If you want to, you're in a situation of you have to lay off people, that's like very awkward. You kind of welcome them to the team, but you have to make the right decision. Yeah. That means you're self-aware of the current situation you're going through. And as a founder, it's really important. Self-awareness, at least to me, is the key foundational quality in a founder, being aware of what they are, how they want to move in terms of market, product, customers, everything, right? So for you, how did you develop that? Yeah,

it's a good question. I don't know that I have a definitive answer. It probably has something to do with my childhood and feeling a little bit like an outsider. Again, my parents were from Eastern Europe, had thick accents, landed in one of the wealthiest places possible, which was Newport Beach, California, in a place that was, you know, beyond our means, unfortunately. But we— I often felt like an outsider in the group. Mm-hmm. I was always thinking about how do I come across relative to my peers who may not be thinking about that as much. And so I think there are pros and cons to that. You can be, think too much. So I've always tried to find that balance over the course of my life. And I think as you get older, you get better at it. Also, reading is just such an advantage. I mean, I love reading memoirs and biographies of people's lives and understanding the arc of life. Mm-hmm. I think movies teach you a lot about the hero's journey and you see that playing out often with entrepreneurs as well, right? Where they start out, they don't know something, but they feel some call to a higher purpose and they make mistakes along the way. That is often part— one of the best ways to learn is to try, fail, and then try again.

Right. Yeah, that's amazing. Let's dive into one of my favorite topics, kindness. being transparent and doing things in public in a very authentic way. I think you've tweeted this a while ago, nice and kind are not the same. Nice is more of like short-term and kindness is more like long-term and it kind of like helps you avoid the unpleasantness. So I want to understand, how do you develop— how important is kindness to you as a founder? As a person, we can talk about other things given in the market where we are in, meaning, like you said, it's more of hustle. People see a lot more about you being very aggressive as a founder. A lot of people count that as a strength. But truly, to me, kindness is a strength, is an invisible strength. And it goes a long way, goes for like years. So, how important kindness is to you as a founder?

Yeah, I think it's such a powerful distinction, this idea of nice versus kind. And nice is really, as you said, it's conflict avoiding, right? You're trying to just, maybe you don't say the thing that you want to say because you want to avoid the short-term unpleasantness. That's a detriment to everybody. So kind is often saying what, addressing the elephant in the room, right? And in startups, that's really useful because speed and velocity really matter in startups. So if I'm working with somebody and I'm disappointed with something that they did for a work project, but I don't say it and I just say, hey, good job. That's not, that's maybe nice. That's a nice thing to say. Good job. Right. Kind because it's not fully honest, right? I'm not—

Right.

I'm not expressing what I feel. And then that latent feeling bubbles up in other ways and other interactions. Or it's also not kind because there's no constructive feedback, right? There's no saying, hey, this doesn't meet the expectation, and here's a way that I think it could have been better. So kindness, I agree, is a strength. I think But it's different than being nice. And I think the two are often confused.

You're absolutely right. I think a lot of people, especially when they, especially founders gathering feedback, they have to eliminate nice people, honestly, or else you just end up doing something that people don't want. because a bunch of people are nice to you, which is, you know, which is like a bigger problem to solve. Versus, you know, I personally feel kindness is such a tricky thing to do. You keep the honesty bar high, at the same time you care about them. So, you have to balance both. Yeah. It's not being rude. It's being upfront and caring about showing that care in a very honest way. So,

uh,

that's

like when I think about the points, just to jump in and make it more clear for me is, you know, if somebody has food in their teeth, right, you can say, you can not tell them, right? Apologize. You know, I didn't wanna be rude. Or you could say, hey, you've got, I wanted to let you know you've got some food in your teeth. No big deal. It happens to me. Uh, but just thought you should know. Right. And just that interaction, it's kind of uncomfortable, right, to acknowledge it. And they feel a little bit, But you can do it in a way that feels very graceful, right? Right. I often, if somebody has food in their teeth, I'll often just preface it by saying, oh, I learned this great rule of thumb that if you know somebody's first name and they have food in their teeth, you should tell them if they have food in their teeth. So I know

you've got it.

Right? So like just finding some ways to be graceful about it, it's just—

Right.

There's a way to be kind without being rude or overly And considerate.

And kindness often is about doing the right thing in a very careful way, meaning like in a very empathetic way, in a very, in a way that you are actually resonating with the other person, you know, instead of, like you said, you can either skip it or you can say something very bad and like make them feel like terrible. So, and in startups, it's really, really important, you know, I've dealt with a lot of kind people who just encouraged me when I was doing something absolutely wrong. And I've also dealt with people who really cared about me. And you were one of them. Like when I was struggling with ShoutOut, getting the users or transitioning from my day job, or like managing, balancing day job, you were very kind and you said, hey, take these 3 steps in mind, keep these 3 steps in mind and you can still do it if you balance both, which is why I feel very less people are kind because it's difficult to manage the conversation in reality. So let's dive into this. You and I, we're both dads. You have 3 kids, which is— I don't know how you do it.

Very lucky.

What's, what's, what's, how you, how's your life being a dad and a founder and, you know, a lot of other things?

Yeah, I have 3 kids who are under 6. So anybody who's a parent knows that that's, that's a lot. I think there's, prior to becoming a parent, I had so little appreciation for just how much work it is to have kids and just how constant it is, right? It's, I, you know, there were periods in my life where I didn't get a lot of sleep. But you would then have a period where you could sleep, whereas with kids, every morning they're up at 6 o'clock, right? And they want your attention.

Yeah.

Right. So look, again, I'm really fortunate. I have a wonderful partner who's able to, you know, take some time off of her work and work part-time and take the primary role, right? So, you know, I just want to acknowledge that privilege. But when we first had our first kid, I really, I actually felt really concerned because I was a founder. Mm-hmm. I think there is this common ethos in, in the world and in tech in particular that you can't be productive and be a parent. And—

Yep.

And the reality is, is that I actually have found that being a parent has made me way more productive and way more efficient with my time. And, and it's also given me a much clearer sense of priorities because—

Right.

I really value the time that I have with my kids. And so I, I wanna work on things that I believe are, you know, complementary to that desire and also doing things that would make my own kids proud as well. Right. And then because you do have those deadlines of, I know a kid's gotta, is gonna wake me up at 6 o'clock, I now wake up at 5 so that I can get other stuff done before that happens. It's just a real forcing function. And, and just, you know, I, I find that deadlines really help and kids create a constraint for you that you work around, and constraints often lead to a forcing function for innovation.

You're absolutely true on that front, which is, I think I had the same worry when, you know, when we got to know about my wife being pregnant and we're expecting baby and like, what the fuck? At that time, I was just transitioning into working at a Fortune-funded company at a very lazy laid-back job to fast-growing, high-attention, high-focus job in a startup, early-stage startup. So I was very concerned. And frankly, I think it actually made me very organized.

Yeah.

And now I plan more, like 2x more than I usually do in general for everything. Like every day, It's very scheduled, it's on time, and you have to do things without a heartbeat. Like you can't skip— if, like you said, you can't skip a morning meal, you have to be present there. So that means you have to do 10 other things to make sure you're present with your kid. And in a way, like you said, the other thing I want to touch as well is they drive you insanely crazy in a good way, which is— When I say drive you crazy, not about like the day-to-day activities. They drive you to be more ambitious and they drive you to dream more because you have to do better things for them, not for yourself anymore. So you kind of care about an external person. And as a founder, as an operator, you kind of like only you're in your lane, but not anymore. As if you become a parent, you kind of stretch because you have a reason now. You have a very strong reason now to do even more ambitious things. So that's why after Rohan was born, my first kid, I did like a hell of a lot more things than before. And it's all because of him, to be honest.

Yeah, I found the same to be true. And again, I think it's a forcing function. You know, it's really easy. A lot of, I think a lot of going back to kind of the hustle porn culture, you see a lot of people saying they're working 100-hour weeks, but they're spending half of it reading TechCrunch, you know, and there's just a lot of lost time in a day, especially when you're young and don't, don't have that forcing constraint. Uh, and so you find ways to become more efficient and effective. Also, I think being a parent increases your empathy and I think it helps you as a manager too of other people. Yeah. courses, right? I mean, just if anyone had to negotiate with a toddler, it's really intense. You learn really great communication skills and negotiation skills. So I think it's really a lot of relevant experience.

And patience, that too. That is an amazing quality. They kind of help you adapt. Warren, it seems like you should— you're on a great— either a Medium article or a great Twitter thread. Like a quality of a parent can translate into a quality of a founder. That's a great idea for you.

Yeah, thanks. I mean, I do think that having a startup is kind of like having a baby. You know, you never feel like you give it enough attention and it always wants more and you want what's best for it and you feel a lot of responsibility for it.

Absolutely. I do have a last question before I dive into another very funny section. which we'll talk in a few minutes. And this question is about ambitious people. You've worked with incredibly ambitious people, like take Chris Paul, the NBA superstar, take Alexis Ohanian or Scott Kelly. These were some of the collaborations you made at Knowable. How was your experience working with them and any key lessons you learned in their You know, in their day-to-day life, or their— how do they think and whatnot?

A couple of things come to mind. One is everyone's figuring it out as they go, right? And I think there's— it's really easy to have this mythology of a person, uh, but the reality is that they're still just— they're humans and they have the same 24 hours that everyone else does. So just remembering that, um, is important. But again, I do think that being exposed to people who are at the top of their game and learning from them firsthand is such a, such an advantage and such a fortunate thing.

Right.

I'm a big fan of all 3 of those people that you mentioned, you know, and they, they led courses for Knowable. Alexis was, was also an investor in Knowable and I mean, he's just a really impressive, caring, thoughtful person who's also a parent and doing incredible things. And many things too. So, you know, it's great to work, to get to hang out with people who are at the top of their game because you learn a lot from them and seeing their habits, but you also learn that they're just people too and they make mistakes. Right. And they're still trying to be better and grow. just like we are. And everyone's on their own trajectories.

Yeah, definitely. I think that's such an important lesson I keep very close to my heart. Your heroes are still figuring out just like yourself. They're, they're maybe like 100 steps ahead of you. But they're in the same boat. They're just like, you know, they have their own problems, like you have your own. No, that's amazing. Any key takeaways, meaning something you've kind of discovered after working with them that you've thought like, wow, I should have learned this years before?

Something I've noticed about high performers is they're generally really quick on replying to things. They just get stuff off their plate really quickly. So they have just a lot of momentum. And I actually learned this tip from Alexis. He was describing when he, he's one of the co-founders of Reddit, and in the early days, you know, the email box would fill up. Right. And he has this tip which is just reply to the most recent email first, because at least that person will think like, wow, this person, this founder is incredibly lightning fast. And then work your way backwards. So it's actually a last in, first out order of responding to emails. Something that stuck with me. Love that. Get back at least on top with some people.

Love that. Awesome. Yeah, that's an amazing tip for sure. I see why he did that. You know, people really appreciate immediate responses and immediate attention, especially if you're a founder serving a customer. Love that. So I have this very authentic section I call Rapid Fire 5, where I just ask like 5 quick questions. whatever that comes top of your mind, just shoot it out. You mentioned before about you're a big fan of reading biographies, memoirs. What's your all-time favorite?

I recently read the autobiography of Ben Franklin.

Nice.

Really, I mean, he was just ahead of his time. He would have crushed it on Twitter, I think. He was basically into intermittent fasting, waking up early, Having building habits, he was a vegetarian. He actually started the first newsletter. I think he has basically invented Substack before.

Love that. Wow! I should I should read that for sure. Thanks for that suggestion. Yeah. So question two: If you were to invest in a company today, you know, what would that be?

I actually got this advice from Gary Tan. I asked him what some of his best investments have been. Gary is now the president of Y Combinator and previously was the co-founder of Initialized Capital. And his point was you want a huge market and great margins. And ideally you have both, right? And so again, venture investing is so much about power laws and these outsized returns. Mm-hmm. So those are 2 things. I mean, you know, finding a company that already has traction, but where the price is right is the sweet spot, right? So that's not overvalued, but you can clearly see that there's a path to exponential growth. Are you looking for a specific company?

Yeah, I would love to hear what's in your mind. Like, what companies are you looking at right now?

You know, I just started working with First Round. They have a program called Angel Track. I feel really lucky. I was one of the people selected to participate in that. And so—

Nice.

They kind of train you up on best practices for angel investing. And there's so many great companies out there. And I actually, I don't have one specific company that comes to mind. Just, just yet. I think there's different stages. Um, obviously I think AI is a really interesting space. A friend of mine from college is named, uh, May Habib, and she started a company called writer.com. And, uh,

that's,

that's a founder who I think is just incredible and in the right space at the right time. Um, so they're kind of like an enterprise-focused Grammarly. And, uh, I would definitely invest in her company.

Awesome. So this is another cliché question which I have to ask because you have such a— you've gathered such wisdom. If you were to go back 10 years before you did everything, like all 3 startups, what's one thing you will change and why?

Buy more Apple stock. Buy Bitcoin and then sell it at the right time. I, you know, I tend to think that things just happen for a reason and step backs are often just the best way to learn. So I don't know. I wouldn't change anything. I don't know how it would affect the multiverse. So I'll just leave it, leave it as is.

Nice. What's your favorite pastime with your kids?

Reading. My daughter is now old enough to where we can read chapter books and it's so fun because the writing is, you know, interesting and it isn't just one sentence, words with pictures or pages with pictures. So that's been, that's been really fun. We're reading a book that is like the alternative Harry Potter series and—

Oh, wow.

Do

you read like at bedtime or just like, you know, some— whenever you get time with her?

Yeah, it's usually bedtime. It's just part of the bedtime routine.

Nice. Yeah, Rohan started— we— he loves books for some reason. I don't know why, because of the pictures or whatever it is. And he recently started pointing out to sentences in a book. And he signals me like, hey, Read this. So I hope like, you know, he loves books when he grows up too. Love that. Last, last question.

Yeah, go ahead. How old is he?

He's 15 months. He just turned 15. So he's learning quick, which is like very surprising to me. The last question about like same, same same zone about books. What are you reading right now? You want to like recommend to listeners?

Sure. Let's see, a book that was recommended to me by Ev, who's the founder of Twitter and the founder of Medium, that I really enjoyed is called Good Strategy/Bad Strategy. And I think a lot of people use the word strategy. Very few people know what it actually means. The thrust of this book, the TL;DR is people often confuse having goals with having a strategy. Right. Right. They say, we're gonna double revenue in the next 12 months. And that's a goal, that's not a strategy, right? So strategy really is what's the plan? How do you actually use your competitive advantages to achieve your goals? So that's one that's been really great. I actually, I really like reading fiction and short stories when I have the time. I think that Fiction gives you a glimpse into interiority of people, right? I think we kind of lose that today with just, with a lot of video consumption and nonfiction consumption. You, you for— you don't get to hear like, oh, here's how other people think about things inside their heads, right?

Right.

Um, so I, I'm reading a book of short stories by this guy Edgar Keret, um, which is really good. And, uh, Also reading this book called The Outsiders, which is about some of the highest performing CEOs of all time. And it's,

well,

it's often people who really thought hard about shareholder value, right? And not necessarily building the biggest companies, but actually just building the best companies for maximizing margins. So that's good too.

Love that. Love that. I'm going to include all those recommendations in the show notes. Let me tell you this, Warren, this has been great. It's one of the most authentic conversations I ever had in my podcast. And thanks for being you, yourself, and delivering such high-quality answers, which I hope listeners are going to take advantage of. So thank you so much for being on the show. And where can people find you if you want to Close out with with with some comments.

Well, my pleasure, Sharath. Thank you for asking such thoughtful questions, and again, I'm such a fan of yours. I'm excited to see this podcast grow, and and I enjoyed listening to to some of the others that you've had on the podcast so far. And I know that you're going to continue to deliver a lot of value to your listeners. So thanks for having me. In terms of where people can find me, Twitter is the best place. My handle is @WWShaef S H.

Awesome. That's it, guys. Thanks for tuning in again. We will wrap this up on a high note here. We'll see you next time.