Cold open
Welcome back to 20VC with me, Harry Stebbings. and I’m so excited for the episode today. First, we have some breaking news in the episode, always exciting. And second, it’s a show focused on the intersection of venture capital and media, one of my favorite topics to discuss. And so with that, I’m thrilled to welcome my friend and newly minted fund manager, Sahil Bloom. Now, Sahil, if you do not know, his threads are some of the most seminal threads on Twitter. They get more likes than Tiger does deals. I thought I was a bit ropey when I put that one in, but I thought it was funny at the time. But anyway, and he really is such a great source of knowledge. Outside of Twitter, he’s built an incredible, incredible, brand. And as I said, some exciting news for us today. Before Twitter and before the last year, he spent the last seven years at a large investment fund, managing over billion in capital. And he also serves on four boards. If that wasn’t enough, he’s also an active angel investor in over 30 companies. And I to say huge thank you to Kat Cole, Todd Goldberg, Shahid Khan, and Greg Eisenberg. Some amazing question suggestions for Sahil today.
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Conversation
Sahil, this is such a joy to do. I’ve been so looking forward to this one. You know, honestly, Twitter threads annoy the shit out of me most of the time, and then yours come along, and they’re so good. I’m like pissed that they didn’t come from me. But anyway, thank you so much for joining me Sahil.
I’m happy to be here, and Twitter threads annoy me sometimes too, so it’s okay. I’m with you.
Oh man, I love it. Normally it’s such a formal intro. That was a very casual one. But I to start with 2018, You didn’t have Twitter. You only started in 2019. Respectfully, who the hell are you and and where did you come from?
I abstracts myself that a lot, actually, by the way. it’s actually 2020. I didn’t start sharing things on Twitter until May 2020. I had a few hundred followers at the time and it was basically just COVID had happened. I grew up on the East Coast, ended up out in California, played baseball. You can see that on my Twitter profile now. I gave up a grand slam on national television. I went into finance. I took a job at a private equity fund doing the very traditional path in mainstream finance, I was doing LBOs and doing the whole dance around that.
But I always knew that I really wanted to work on early stage if I wanted to think about the future rather than thinking about the past. And so I just didn’t know what that transition was to be. Right? Like you’re kind of on this momentum building path within finance. and I didn’t know what it was to be. COVID hit. All of a sudden, I wasn’t working hours a week. I wasn’t traveling four days a week like I was before. That was kind of my jumping off point to go try something new.
And what it ended up being was building, right? I was writing around all of these topics.
Man, I want to ask, I think there’s a a load of people who are in your situation in terms of being in very secure financial positions in financial services, in more traditional finance roles who want make the move. With the benefit of hindsight that you have, I guess, what advice would you have for them?
Yeah, I think the biggest thing is just following your energy around these topics. And I don’t say that in a fluffy way. sounds really woo woo and fluffy to say, follow your dreams, follow your energy. And I really don’t mean it that way. What I mean is I’ve written about this concept of your zone of genius. There are things where you know that you are playing your game around a given arena versus playing someone else’s. And in the traditional finance world, for me personally, I was good at it.
I was fine. I could have continued progressing, but it wasn’t my game. I was never going to be the best it. I was never going to really be exceptional because it was playing by someone else’s rules around something. so my biggest advice that I give to young people is figure out what you have a chance to truly be exceptional at, because that is always going to be what you have the most energy around, what you’re willing to put your head down and really grind around is going to be that thing.
So if you have the luxury of thinking about it, which not everyone does, and so if you do take advantage of it and go find what that thing is that you can really accelerate around.
I do want ask, know, when you look back at kind of the early Twitter days, what did you learn about what worked versus what didn’t work, both on audience growth and on kind of content type and style?
I think the biggest rule and like the golden rule I always had around this was that you need to create value for people, and then you’ll receive value in return. return. I think it’s a golden rule for life. But with Twitter, that was what I found from the early days was if I was creating content that created value for people, then I received value in the form of their attention in this case. And so people are following you. wasn’t going out with the goal of follower growth.
I was going out with the goal of creating value, knowing that that would lead to people gifting me with their attention. And so I found personally that the way I created value was around things that were more evergreen in nature, creating content that wasn’t news. It wasn’t like breaking this, breaking that, creating content that sat out there that someone could come back to years from now and it would still be really good and still be quality. And that was what I focused on. It was just like build this repository, build this base, and not everything’s going to go viral, but that’s okay.
Keep putting out things consistently. And that’s always been my skill set in life. I’m not to be the flashiest. I’m not to be the sexiest. I’m not to be, you know, the fastest person on the field, whatever it is. It was just, I’m never going quit. and I’m just to keep pounding my head into that wall until it breaks through.
Did you see inflection points in your content and in audience growth?
Yeah. I mean, scale is undefeated. So as you get bigger, it gets easier to grow. Point blank. I mean, full stop, right? The first 100,000 took, I don’t know, eight, nine months. And then I think I’ve grown 100,000 in the 45 days or 50 days. So it definitely accelerates as you go just because you’re on a bigger base. The inflection points from an actual content perspective were more just around reps. You just are getting much better.
I always think that if you look six months in the past at anything you’re doing, like for you, if you, go listen to episodes you’ve done six months ago, you should almost cringe at how shitty you were at this when you go look at that because that’s how you know that you’re improving and that you’re getting better at your craft. And that’s how I always felt about my writing personally was like, I to cringe when I go look at something that I did six months ago.
I totally agree. I mean, think six months ago was probably a respectable podcaster and now I’m just a reprobate. But yeah, I’m sure. I do to, you know, start on, you know, bluntly some pretty exciting news. So I hear you have some news for us today, Sahil. What news do you have for us and what’s the announcement?
Yeah. Well, I’m excited to to have the opportunity to do it here because it feels very fitting, but I’ll be announcing my first venture fund. called SRB Ventures. SRB or my initials, Sahil Ready Bloom, debut fund anchored by some amazing people and with participation from a bunch of people that I really, really, really, admire and have learned a lot from. So I’m super excited to be kicking this off and announcing the closing of fund.
Man, I’m so thrilled that you’re doing it here. Really, honestly, it means a lot to me. Can I ask, how did you come up with the fund size? Why did you choose 10? And how are you thinking through portfolio construction, check size, deployment? What are the thoughts there?
So I originally thought I would raise five. Part of that was my own, you know how this works. like my own imposter syndrome, self- limiting mindset around these things where I was like, shit, no one’s to give me more than a few million bucks. And I’m to go out, try to raise five, but if I can only raise two, that’s okay, and I’ll just do that.
I think it was like in two days it was over five. basically. then what happened was I realized that if I had over 99 LPs, I had to keep it under 10 legally. and I offered it to a bunch of my friends and family because I’m a huge believer in like bringing people along for the ride. and a lot of my friends wanted to learn more about the things I was doing so quickly the LP base grew past 99 and I had to keep it under 10.
So then that was the actual limiting cap on going out and doing it. In terms of fund construction, it’s going to be largely stage agnostic, but it’ll probably concentrate around pre-seed, stuff. In this environment, there are slam dunk. You and I have talked about this. If there are slam dunk risk adjusted opportunities that are series B, I’m not to pass up an opportunity to go and participate in something like that. It’ll just have to be a bigger allocation, bigger check size into things like that.
How do you think the biggest challenge, which often is the case for bluntly, you know, a lot of the micro funds, is kind of bucketed into kind of the angel world and actually not really angels and 25k k checks are hard to make work. How are you thinking on the discipline you’ll have around check size? Will you do 25 and 50k k checks?
50 will be the smallest I would do. I think everything will probably fall into the 50 to 250 range. know, coming at probably series B rounds and smaller checks into earlier higher risk things. But I think 50 will end up being the smallest that I will do. The benefit of being small, which you and I have also talked about, is that it’s not hard to get into a deal with a small check. If you can show some amount of value, then the trade for the founder is for this tiny amount of dilution, is this person going to deliver that value for me?
And with what we have with a platform and the ability to go use this megaphone for these companies, that’s a very easy trade to make at 100,000 or at a 200,000 allocation. It might be a very different trade at a a million million allocation or a $500,000 allocation, which is part of the reason that I think being small for me with an initial fund is actually an advantage to getting into the best things.
How do you think about managing founder expectations? Because both of us have these big microphones. How do you think about managing founder expectations when it comes to what you are and aren’t willing to distribute and promote?
Yeah, it’s a great question. I got asked that by a lot of the thoughtful LPs that I had discussions with was like, you invest in 50 companies, are they all to be hitting you up? Are you just to be having to tweet about the companies all the time? I think it tends to be in terms of very few of the companies will actually take you up on all of the different things you can do for them. you’re able to deliver something comprehensive to a handful that is really valuable for them. and then for the rest, it’s fundraising announcements or big feature announcements or big things that happen and you’re amplifying those stories.
It ends up working out where you’re not spending all of your time just sitting around tweeting or newslettering or podcasting about these different companies. But I think the big inflection points tend to be around big announcements. Right? The other day, there was an example. one of the companies, one of the first investments out of the fund is this business, Wander. QED and Redpoint were leading the series a short term rental, vertically integrated platform. And I did this video to announce it. Packy and I were both doing an announcement for the investment in the company, and Packy did a thread we’d agreed we were to do threads and Packy was like, shit, I don’t to do a thread.
I’m not a thread guy. did a thread and then I head faked him and I did a video he was annoyed and giving me shit for it. but I did this video and I put it out. was very easy to go and pull together it did 50,000 views in 24 hours on Twitter. And that is just what I invested in the company relative to that very quick value delivery from doing something like that is insane, the leverage that you can get on it. And so that was a very quick example to me of like, there is something to this that is just different.
We did a Twitter spaces with the founder and had several hundred people on very quickly. All of a sudden you generate this massive momentum that drives real clicks. And when you think about it in the advertising world, the amount of money they would spend to get 50,000 impressions on something like that, to get the millions of impressions that the tweet did, I mean, it’s really, really, impressive, I think.
I do want ask, you know, it takes me to something that you said before, which is the traditional VC model is dead slash dying, just to put the caveat of slash dying. Why are the traditional middle tier VCs going to get their lunch eaten, my friend?
Yeah. I think what you’re seeing is a barbell that is formed or forming within the VC landscape. And on one end, have the Sequoias, Benchmarks, Andreessen’s, you know, they’re like, and even Tiger, I think now, Coatue, who have developed this name brand and this cachet and this real winning edge that I think exists around that and continues to be self fulfilling and self- perpetuating where when they come into a round, everyone’s like, oh shit, I’m not going to invest in the competitor. Competitors all get scared.
There’s a ton of money behind one player, etcetera. will continue to exist, I believe. And then on the other end of this barbell, I think you have people like us, people like Josh Buckley, people like us, people like Packy, people who have some very clear value lever that they can deliver to companies. And in your case, now you’re big, but with smaller checks. Now you’re pushing towards this other end of the spectrum. That’s a whole different story where you’re going to become one of those guys on the other end of the barbell. kudos to you.
I’m going to stay over on the other end where you can get into any deal, and you can drive material value with some specific lever, whether it’s a fund that gets raised because they’re amazing performance marketing guy Nick Sharma with Sharma Brands. amazing. Or if it’s someone like me where I have a platform and I can go help you get access to all of these customers that exist out in my pool of people that are following me that have gifted me with their attention. Those are the two ends of the spectrum that I think work.
The middle of this landscape that exists here is going to be challenged. And I think what it leads to is maybe not the death of the middle. it’s going be survival of the fittest though, where they have to and will be forced to figure out what their true value proposition is because the capital as a value proposition is completely dead.
How do you feel when you see this awakening of venture firms to the power of content and their resources behind it?
Well, I think it’s interesting because I never built an audience as a venture investor. investor. My audience is not a bunch of other venture capital firms or venture associates. My audience is a bunch of real people that are looking to learn, grow, explore things, etc. And in my opinion, that’s much more powerful because that audience is real customers of whatever it is that these companies that I’m investing in are selling. Versus venture firms who, their associates are told, hey, go out and build an audience and their audience ends up being a bunch of other venture associates who are all liking each other’s things and sharing it.
That’s tough, Because then you’re tweeting something out and you’re sharing about a company, the only people that are seeing it are a bunch of other people within your little ecosystem. So I think they are going to run into challenges around that. It’s going to require real defining for them to figure out what is our core value proposition of this content. Is it just so that we can tell our founders that we have content arm and we’re sharing? Or is there a real reason for being real insights that are being driven through it?
I think Andreessen is probably the best example of a firm who has done this Well, you know, they created future, which is almost like a standalone media entity, and they’re trying to really think thoughtfully about having that as a real media platform. But it’s to be hard for a lot of these guys to do it and do it well.
I think my kind of phrasing would be that traditional venture isn’t dying, but we’re to see reduction in their power and influence. And what I mean by that is the days where they could take 15% are gone. It will be a new generation where they take seven and a half percent alongside people like me and you taking seven and a half percent. Now me and you bring distribution, we bring content, we bring brand, we bring a lot of resources that they don’t. But then they also they do bring great stuff too.
It can be structuring of companies, it can be scaling between phases, hiring the execs. where me and you also don’t have the time because we’re also building content companies.
Yeah.
Do you see what I mean? I
think doing I do see what you mean. I guess I would recharacterize what what I was saying as I don’t think it is dying. I think the venture landscape is becoming increasingly distributed. You know, it had been very centralized for long time. Then you had the proliferation of other firms that grew, a lot of them from the lineage of the handful of original firms. And I think all of a sudden we were at this unique tipping point in time where suddenly it has become so distributed and the capital is flowing into a bunch of different people’s hands. and you’re going to have a very cool laboratory of like, does this work?
Over the next years, we’re going to find out, do we deliver exceptional returns like we think we are? Is our media angle going to actually accelerate the trajectories of these companies, going to actually accelerate their ability to raise and create competitive moats around their industries? We’re going to find out. But I do think you’re seeing this distribution that is now happening. are moving away from the centralized VC model and capital is flowing into a lot of different hands.
Sahil, tell me. I know you a little bit. I don’t buy that you want stay small and play your collaborative game. You’re gonna want go bigger and you’re to want write bigger checks and lead rounds. I know you. You’re like me. That’s why we get on. Like, what is the actual plans?
I’m gonna stay small and I’m gonna continue to write small checks. Closely held plans, man. I don’t have some grand strategy right now, to be totally honest. I like to push. That’s my wiring. With everything that I do, I like to put my head down. I like to push, and that’s how I’m always going be. I don’t necessarily think that that means going bigger. I personally think of what’s kind of being built right now is like like a less quirky Tim Ferriss with an investment fund is like what I’m kind of going for as, as, a vibe.
And I think, you know, that doesn’t necessarily require me raising bigger and bigger funds, plenty of ways to make money that I think don’t involve going out and raising million dollars. What I ultimately want to do is drive exceptional returns for my investors, I want to invest in the best companies in the world, and I want to be a part of putting capital behind companies that change the world and hopefully change the world for the better. And I think that as a capital allocator, that’s an amazing goal and amazing vision.
Does that mean I’m to go out and raise, you know, 100 million dollar funds? I don’t know. I’d be surprised if I did. You never know.
Can I ask? I spoke to Greg Eisenberg, your podcast co-host, and Kat Athletic greens, before the show, and they both mentioned your insane work ethic. They said it was unparalleled. Again, why I think we get on. But like, what actually drives you? Why do you work so hard?
I’ve never really been able to figure out what my internal engine is around things. You know, I grew up, my mom is a first generation immigrant. She grew up in India. My dad is white Jewish from the Bronx. His family didn’t accept when he wanted to marry my mom. I never really met anyone on my dad’s side of the family, which was just kind of a crazy set of circumstances. But I grew up in a household that was very hardworking. My dad’s a professor. I’ve never seen anyone work like my dad.
I mean, to this day, I’ve never seen anyone put his head down and grind on things like my dad. And it wasn’t blue collar work. He’s a professor, but just so driven to learn and grow. And I always kind of just developed this, like, chip on my shoulder thinking I wasn’t the smartest. Like, found ways to motivate myself that I was a fraud or an imposter all the time. And that, you asked a question about insecurities. my biggest insecurity is that I don’t know what the fuck I’m doing.
Excuse my language. that is my biggest insecurity in life is I’m constantly fighting this urge of, who am I? What am I doing? And I need to work really hard to continue to prove myself at every stage of what I’m doing along the way. I think it’s Josh Wolf that always says chips on shoulders, put chips in pockets. And I really believe that. And I don’t know why I have this chip on my shoulder, but I had it in baseball because I just knew I wasn’t that good.
Everyone was much better than me, and I had to find a way to compete. For me, that was just being relentless. I was just gonna over and over again, like, you could hit a home run. I was just gonna keep throwing, and I just was gonna keep coming at you over and over and over again. And that mentality for me has played out in my career. It’s played out, you know, in relationships and being there for people, I hope, and really in everything I do. And I plan to keep it going in you know, this next phase of my life.
Do you find you get highs and lows? I consider us both founders of media businesses. You know, the highs for me are very high. The lows are very low. And I think the thing that people forget is the speed between moving from one to the other is very fast. Mornings could be super high and evenings could be super low. Do you find the same or are you relatively even keel?
I’m pretty even keel. And the reason I’m even keel is from lessons learned on the baseball field. Because what I learned playing baseball was every time I got high, I’d get punched in the mouth. And every time I’d get too low, I would hold myself back from performing. And so what I learned was I had to be even keel in order to perform at a high level consistently. And I think it plays out in everything in life. And it’s a great lesson that’s learned on the sports field.
Never get too low because you’re literally always one pitch away from getting out of any situation. Never get too high because you’re also always one pitch away from being just kicked in the nuts. And that has allowed me, I think, to play out much more even keel. If something’s going well, great, it’s going well. Feel happy. Pat yourself on the back. Sure. But just like know that you’re one moment away from just getting punched in the mouth.
That’s a great title for any episode. One moment away from getting punched in the mouth. Happy Monday. Listen, I want ask you, I think, you know, luck plays an important role in a lot of journeys, but then also not as important as some people suggest. You said before that luck is misunderstood and can be engineered of sorts. How do you think about this? And I guess, can you provide some examples?
Yeah. I always had this concept. I think I first read it from Tim Brown, who was the CEO of Ideo at the time of engineered serendipity, that you can engineer your own luck. And I’ve thought about it a lot, I’m actually working on a piece I’m going to write about how to get lucky. But in general, luck is misunderstood in that a lot of what we perceive as luck is just the macro result of thousands of micro actions. And what I mean by that is you’re doing something consistently that led to you getting lucky. then you say, oh, I got lucky. this thing happened, this break went my way.
But really it was that you were doing something that led to that situation. An example of that in my own life, I used to get up super early to go to the gym. When I first started my career, I wanted to be in the office by 6:30am, be at my desk first, because for some reason in my mind that mattered. I think it’s stupid in hindsight, but that mattered to me. And so I’d get up at do some work. I’d get to the gym at 5AM on the dot, and I’d work out every single morning, five days a week.
At that time, this is at Equinox in Palo Alto, where I was working out. There was maybe five or six people that would show up, like, that were crazy enough to show up at the gym every morning at that time. At the time, this is like 2014. One of them was Tim Cook, CEO of Apple, who’s new CEO at the time. He wasn’t super famous yet. And I spent six months basically chatting with him every single morning just by virtue of the fact that I was one of the five other people.
Not because I was impressive or because anyone there was particularly it was just I was there. And so it was a situation that I was putting myself in because I was driven around wanting to work hard and show up. That then led to what has become one of the most important mentor relationships in my life. He’s become an amazing mentor. He’s a backer of mine, taught me a lot. That wasn’t a situation where it was true luck. It was luck that was created by the fact that I was showing up day in, day out with no intentions of having some end to it. it. was just the natural byproduct of actions on my end.
Can I ask, I was with a mentor of mine the other day and I was debating a tough decision. He said something very simple. He said to me, you’re never wrong to do the right thing. And it really just framed how I thought about this decision and a lot of decisions. and probably is one of the most meaningful things that he said to me. When you think about your relationship with Tim, what are the biggest lessons or takeaways you think you have from relationship?
I think he is one of the most principled and value driven people I’ve ever met. And I admire that deeply because I think there are very few people in the world that are that way, who are so deeply connected with what their principles and values are that they’re able to let them guide every decision. And sometimes it looks like you aren’t in a short term decision are making, but really the long term view that you’re taking around it is connected to what your principles and values are.
And I’ve always really admired that about him publicly and privately. The things that he does, the actions he takes, the friendships that he cultivates, the loyalty he has for friends and people who have been there with him. I think that that is probably what I’ve taken away. And that’s not necessarily something he has said explicitly to me. It’s from watching and observing someone that I just truly, truly, admire about him.
No, listen, I love that and I I love that story also. Fuck me. I would not be getting up at 3:45 a.m. That is brutal, my friend.
I’ve always been a morning person, to be fair.
I know. You messaged me like 6AM. I’m like, Jesus, that’s early. What time do you go to bed?
I go to bed early. I’m probably in bed by like most nights. Not when I go out with Shahed and get drunk like last night in New York, but normal nights.
9pm Well, no wonder you get up so freaking
grandfather, man. I’m like going on It’s great. I get into bed with my tea. I my little cup of tea in my book, and I Listen, man.
There’s some questions that I’ve just wanted to ask you for a while that I think would be really interesting to dive in on. it’s like the threads are epic. They’re long as well. What is the writing process for you look like on each thread? How do you decide which topic to focus on? Talk me through it.
So I have what I call a content engine. Like, that’s what I think is at the heart of a creator’s process, has to be a content engine, which is what allows you to produce high quality content consistently. So for me, I think of my content engine as all of the things I’m regularly consuming, the different newsletters, the podcasts I listen to, the things I watch, whatever it is, that’s where I’m getting ideas, topics where I’m pulling out insights from them, novel insights, things that I, you know, made me go, or oh, shit or whatever it was.
And then I log those. Like, I use Notion, but I basically just log them into a board where I have all of these ideas and different things that have popped up from that content engine. I’ve log them all. Then when I get inspired around something to actually sit down and write, look at that board and figure out what it was that I was inspired to write about, and I’ll sit down and write in kind of an unstructured form prior to then distilling it down into something that actually works for Twitter.
So you’ll write like a Google Doc before structuring it into numbered tweets?
Yeah, I will write in a pretty unstructured way, not worrying about how shitty it is, not worrying about word counts, character counts, etc. And then I’ll basically go look at it and distill down to things that are much tighter and punchier.
Do you ever get halfway through and go, this isn’t a great one?
All the time.
What do you think makes a great one versus not a great one? And do you know when one’s gonna hit before?
Yeah, I think there are certain topics that it’s clear that will resonate with large amounts of people. There have been a couple that I would say have surprised me, but for the most part, I know whether a topic has broad resonance or whether it’s more of a niche. In terms of what makes a great one, I think it’s it depends on what you define as great. I’ve put out things that I thought were exceptional that had a tiny, you know, potential audience and didn’t go anywhere.
But I thought they were really well written and well researched. And then I’ve put out things that I thought were like kind of fortune cookie and broad, but people like that. And maybe it resonated with them because it connected with them on some emotional level, which I also think is great. So it just depends. you know, it depends on, you know, on the situation, on how I’m feeling. Sometimes I like writing things about broad life principles because it helps me clarify my own thinking on those topics.
Or if I’ve been feeling down or up and I’m trying to kind of like change my own mood, writing is my process for doing that. I just happen to share that writing publicly after doing it.
If it doesn’t hit and you see it doesn’t hit, me and you are both smart and analytical when it comes to Twitter. If you see it doesn’t hit, do you take it down?
I never delete threads. The one exception to that would be if, like, if I thought I didn’t think something through comprehensively and somebody calls me out on it and they’re right. Then I would say, like, okay, I actually don’t think there’s a benefit to having something out there that I didn’t think through well enough. But normally I will make sure that I’m to be really proud of posting something before I post it. Individual tweets now and then I’ll delete if I just don’t think it’s hitting or if it’s particularly interesting to be out there.
But with threads, I don’t know that I’ve ever, ever, deleted a thread. Julian, our friend, deletes threads all the time. I’ve seen him delete things that have 20,000 likes because he doesn’t like two or three responses that he gets to it, which I think is, like, insane. He’s done that.
Do Do you ever get down from the responses? When someone responds negatively to mine, even though I don’t know them, they’ve never met them before, it does impact me, actually. I I get a little bit hurt.
Yeah. Negativity bias is a real thing. I don’t know if that’s the right term for it. It’s what I call it, which is, I can post a thread and I’ll be looking through the responses, and there’ll be a 100 positive responses. And then one guy says something negative. Some anonymous account says something really mean or negative, and that’s the only thing you can think about. And suddenly you’re down and you’re feeling it. So, yeah, absolutely. all the time. I’ve posted things that I thought were really thoughtful.
I posted this thing. This is a good example of it. When I found out I was to be a dad, I was feeling very introspective as a result of that. And my whole life changed in an instant knowing that. I wrote this thread about like, principles that I wanted to kind of teach my child to live by. And it was really just my process of being introspective around the type of father I thought I be, the type of child I wanna raise. I got like an amazing response.
Tons of people shared it. it. was incredible. But there was like maybe 3% of people that really took offense to me thinking I could mold my child. And I don’t know why, honestly. It was in good natured, but they were really angry about it. And I got a bunch of angry messages and responses to it. And I was pretty down about that because I was really happy about what I had written and I thought it was very thoughtful and introspective. And I remember feeling pretty down for a day about that.
I just didn’t think it was mapped to like what my intentions were going into that.
I actually didn’t know about the incoming child, which is so exciting. It’s just not a bit of a weird one, which is like me and you are both very ambitious. We both work our asses off. I have a wonderful girlfriend. I’m very worried now that like normal life, girlfriends, kids, wonderful things that happen in life will make me mediocre. Do you worry that with normality and wife and child, which is wonderful, but you you lose the work and you become more mediocre respectfully?
You know, I think the one thing I really changed from my days in private equity to now has been how I define hard work. Like I used to think of hard work in a very absolute sense, where it meant I had to be working 100 hours a week. I had to be waking up at 3:45, showing up to the office at 6:30, the last one in the office, sleeping four hours a night, sleep when I’m dead type guy. That was me. And I learned that from baseball. that was how I got through and survived actually.
But I’ve changed my mind on that because now I really do believe that as a creative, which is at the core, a lot of what you and I do, you have to take care of your full self in order to optimize creative work. And if you’re trying to do inspired creative work, which investing is creative work, by the way, you need to think creatively around things and around ideas and support people. You have to be able to take care of your full self. And for me personally, part of taking care of my full self is being able to go for a walk with my wife in the morning, spend time with my child, coach my child’s little league team someday.
I think that is part of taking care of my full self in a way that I didn’t agree that it was before.
Two things. How do you define high performance? Number one.
How do I define high performance? I think it’s totally individual. I think it completely depends on the person. For me personally, high performance means accelerating in the output and quality of that output. And it has to be better than it was a month ago, much better than it was two months ago, both in the quantity and the quality of it.
You mentioned your wife there. Fascinated to hear your thoughts on this one. How do you think about what makes successful personal romantic relationships?
Oh, man.
Well, I’m soppy. Beyond the bullshit, love love.
Yeah. What makes the most successful? So, I mean, I think, like, open trust, being able communicate, and honestly, being able to realize that most of your life is doing nothing with that person. Like, I think when you first start dating somebody, there’s this honeymoon period and everything’s so magical and doing things and out on dates every night and traveling. And most of life is like sitting on the couch, doing nothing, hanging out, having a drink at night by yourselves. You have to love that person in those moments just as much, if not more than in the crazy, amazing romantic moments.
Because it’s very easy to love someone in crazy, romantic, amazing moments. It’s much more interesting when you’ve found someone that you just absolutely love doing nothing with. To me, that was when I knew that I I was ready to get married was because I realized I had found the person who I was happy to do nothing with.
Do you believe in love at first sight? No. Why?
I think you need to have a connection with someone emotionally and intellectually in order to truly be in love. I think love at first sight is like this superficial thing that got created for movies, and I just don’t think it’s real.
I don’t know. Me and Olivia Amato on Peloton. I I felt it. Final one. Do you believe that there’s, like, one person out there for everyone?
Oh, man, you’re gonna get me in trouble. Rationally. No, I don’t. I just think it’s impossible. You know, scientific, like, numbers wise, everything about it. right? If you were born into a different situation or if you had slightly different life circumstances, I think it’s completely possible that you would have still found someone that you were an amazing match for just by the fact that there are so many people out there.
I mean, God, I love the transition of this conversation. conversation. Final one for the quick fire, Yeah, obviously so exciting with the newborn. Three traits that you’d most like your child to adopt. What three traits would they be?
I want them to be interested. That’s probably my number one trait that I look for in people in general. Someone that is interested, that is kind of curious, that is going down rabbit holes, wanting to learn about the world around them. I want them to be, I call it a darkest hour friend. The type of friend who is there for you when shit is really bad. We all have friends who are there for us to celebrate. Like, oh, you launched the fund, Everyone wants to be there and cheers and it’s great and it’s fun, a birthday party, whatever.
But what friends are there when that fund collapses? Those are the friends that really count. I want my son to be that type of friend to people. And then I think the third one is just to be kind. Be a kind person. There’s so many people out there that are just assholes. It’s so short-sighted. It’s just not a fun way to live. It’s just not a fun energy to give out to the world. And so I really want my son to be a kind human being.
And I don’t think I was a kind human being all my life, and I really regret it. And I think that that really matters.
What do you think made you change?
I got punched in the face, metaphorically and literally. know, I grew up in a small town. I was a kind of big fish in a small pond, played baseball at a high level. I thought I was great. I just thought I was awesome. I was smart naturally at the time. I did fine in school. I got a scholarship to Stanford. I thought I was the shit. And I showed up at Stanford day one and I got punched in the face academically, athletically. I went to class I was the dumbest one.
Went to the baseball field and I was the worst one on the team. And that was so important for me as a humbling experience in hindsight. And it sucked at the time. I remember it really being challenging mentally because it was the first time in my life that I had truly been knocked down in a meaningful way, but so formative in just in changing my mentality around who I was and the type of person I wanted to be.
How did you deal with that? You’re not the best and you’re not actually number one anymore.
I remember having a conversation with my dad. I called him and I was really upset thinking about academically, athletically. And he just said, he said something to the effect of remember who you are and remember what you are great at, which is being consistent. And I had never really thought of consistency as something that was my a trait or something that I kind of held deeply, I guess it was. And so I realized that that was how I was going to win and outperform at anything I did was just by continuing to show up and just being relentless.
That was when it kind of flipped for me. I was like, I’m never to be the most talented. I’m never going be the smartest. I’m never to be the hottest. I’m never to be the most talented on the baseball field, whatever it was, but I’m just to keep showing up. And it’s really hard to keep someone down if they keep showing up. Really, really, really, hard. And so that was when it clicked for me personally.
But I do to move into a quick fire, Sahil. This is so much fun. So quick fire. I say a short statement, you give me your immediate response. Sound okay?
Okay?
So what’s the favorite book and why? I know you’ve got tea in bed with your book. What book should we be reading?
When Breath Becomes Air. the most powerful and life changing book I’ve ever read.
Why?
It makes you completely reevaluate what your life and purpose is and what being alive really means. You need to go read it if you haven’t read it. I don’t to say too much more because it’ll give a lot away.
Tell me, what have you recently changed your mind on?
Hard work. What I said earlier, the nature of hard work and what it means to be working hard and and that you can be working hard in a different way, in relative sense versus just an absolute sense.
What’s the workout routine for you, Sahil?
I’m still a big workout guy. This goes back to my baseball days. I’ve got I built out a home gym, you know, like a full rogue home gym. So I still work out every single day. Right now I’m doing this crazy thing called PLP, Push ups, pull ups, lunges. You start day one, you do 10 of each. And the second day you do 11 of each. The next day do 12, do,,. 14. You go all the way up to where like, you know, today was 51 of each.
I mean, you can take as many sets as you want, but you do it in addition to whatever your normal workout routine is. So you’re doing like 2,000 plus pull ups over the course of days and it’s nuts. It is bananas you get really jacked from it. So it’s it’s been fun.
I love that. What’s the favorite type of steak? How’s it cooked?
Bone in ribeye, medium rare. I’m like a Pittsburgh style guy. People give me shit for this on Twitter, by the way. Like the kind of charred outside. I love the charred outside, pretty rare inside. That’s my go to on steaks.
Do we have a garnish? Do we have a bearnaise, a peppercorn, a chimichurri?
I’m actually just like a butter guy, like a good grass fed Irish butter.
Well, I’m I’m having it tonight. I can’t wait. Tell me my friend, Tiger, CO2 the big crossover funds, how do you think traditional funds compete with them?
Add value. Capital is a commodity. You have to find what your edge is to add value and to really be a partner to these founders and companies.
Big advice to founders who want to build a Twitter following.
Be consistent. Figure out what value you can share with the world. Be consistent in sharing it.
I also think, focus on a niche in the early days. Like, find people who love it. And it could be building cohesion between product design teams and customer support teams. And just tweet about that, but make them love you.
Yeah, it’s like don’t try to be everything to all people. Figure out what you are and what you’re really good at. Own that and deliver that.
Totally. Tell me, what was the most recent publicly announced investment and why did you say yes and get so excited?
Wander, which I mentioned earlier in the conversation. A few reasons. Visionary type founder who I think is exceptional. exceptional. It’s a big swing idea. And if it works, it’s to be so damn cool. And I think it’s probably a low probability that it works like most things in the early stage. But if it does, it’s going to be transformative and completely change the way that a lot of people work and play.
Listen, Sahil, this has been so much fun. As I said, rare that I move to do you believe in love at first sight? But always a sign of a good discussion. So thank you so much, man. and this has been great.
This was a blast. You’re the man. Thank you.
I mean, you cannot say we do not give you variety on 20. I to say huge congrats Sahil. Such an exciting time with the new fund. If you to see more from Sahil, of course, can find him on Twitter at Sahil Bloom, and we’d love to see you behind the scenes. You can do that on the on minute the20minutevc.com. But before we leave you today,
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As always, I so appreciate all your support, and I can’t wait to bring you a fantastic episode this coming Monday.