The Learning Leader Show With Ryan Hawk - 433: Sahil Bloom - The Qualities Of A Great Coach, Investing In Leaders, & Being Positive Sum

Episode Date: August 22, 2021

Text LEARNERS to 44222 for more... Full show notes at www.LearningLeader.com Twitter/IG: @RyanHawk12    https://twitter.com/RyanHawk12 Sahil Bloom is a writer who attempts to demystify the world. He's an investor, advisor, and creator. As a pitcher at the University of Stanford, he once gave up a grand slam on ESPN in 2012 and he's still waiting for it to land. Sahil is an angel investor in 25+ startups across the technology landscape. In this capacity, he works directly with entrepreneurs and founders to identify and execute against core value creation initiatives to build scalable, sustainable value for all stakeholders. Notes: Writing makes you better at everything you do. Writing is the best way to expose gaps in your thinking. When you write, you think better. The makeup of a great coach - Never too big to do the small things. They push you beyond what you think you're capable of. Everyone should take a moment and say thank you to someone who has done this for them. Learning Circles -- Develop a circle of people to collectively learn with. Push your thinking. I do this with my Learning Leader Circles and it's some of the most rewarding work I do. Why the cheeky Twitter bio? ("Once gave up a home run on ESPN that hasn't landed yet"). "People take themselves too seriously." The difference between big public failures and private ones: "I think private failures can shape you more." Freshman year at Stanford was a grind... "I thought I was hot shit." "Are you willing to spring when the distance is unknown?" It's all about how you bounce back from failures. "You need to be able to take constructive feedback. You can't crumble." Sahil asks, "What do I want to instill in my child?" Let them fail... It's the greatest experience. Angel Investing - An individual who provides money to start-ups. The "must-have" qualities in a person for Sahil to invest in them: Resilience and Grit. "You're going to get knocked around. They are willing to die before they'll fail." "I'm driven by relationships over data points. I like to ask: Tell me about a time you got your ass kicked..." Sahil invests because he learns so much through the process of it. The intellectual returns make it worth it. "Writing is the best way to expose gaps in your thinking. It makes you better at everything you do." Be a teacher: "I'm learning alongside you." Great storytelling... "It is a built skill." Disney, Pixar... It's a foundational skill. They infuse personality in writing. The three biggest keys to storytelling: Elicit an emotional response Novelty - That "Oh wow!" moment Punchy & Concise - "I didn't have time to write a short letter so I wrote a long one instead." Viral tweet threads - It started in May 2020 for Sahil. He went from a few followers to hundreds of thousands... Be "Positive Sum." The world is positive sum. A rising tide lifts all boats. You should genuinely root for others to succeed. The makeup of a great coach: In the trenches with the team - never too big to do the small things Willing to challenge you and call you out. They help you get better They push your thinking Coach John Beverly (Sahil's high school baseball coach) He was first to suggest that Stanford could be a reality for Sahil ("He was nuts") He had very high expectations He believed in Sahil more than Sahil believed in himself He changed the trajectory of people Cognitive bias - High expectations lead to higher performance You need to vocalize your appreciation for those who have pushed your thinking and expected a lot from you The power of learning circles: There is push & pull with others Helps you develop circles of friends to collectively learn with and push your thinking

I just think that writing is the best way to expose gaps in your thinking and where your thinking is falling short. It is impossible to write down everything you know about an idea and not immediately see the gaps in what you know about that concept. And so as a leader, it's one of the most important things you can do for clarifying your thinking on any given topic. I recently found an exciting new investment opportunity, Blue Chip Art. Now, it's traditionally only open to billionaires because of the high entry cost. But one startup is making it available for everyone. Masterworks.io lets you invest in multi-million dollar works by artists like Banksy and Monet. Contemporary art prices outperformed S&P 500 returns by 174% from 1995 to 2020.

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slash learning. That's Masterworks. com.I.O. slash learning. Also, please see important disclosures at Masterworks.com.i.o slash disclaimer. Welcome to The Learning Leader Show, presented by Insight,

Insight Global. I am your host, Ryan Hawk. Thank you so much for being here. Text, learners to 4-4-2-2-2 to become part of Mindful Monday. You, along with tens of thousands of other learning leaders from all over the world, will receive a carefully curated email from me each Monday morning to help you start your week off right. You'll also receive details about how my book, Welcome to Management will help you become a more effective leader. Text learners to 44222. Now on to tonight's feature leader. This was a fun one.

It's Sahil Bloom, writer and angel investor. He publishes work on The Curiosity Chronicle of the name. He demystifies complex topics and makes them simple. Previously, he was a pitcher for Stanford. baseball team. Here are the topics we discuss the must-have qualities of a leader he chooses to invest in. And then what makes a great coach both on the field and in the business world? What he learned from giving up a grand slam in a pivotal game broadcasted on ESPN?

And why you should write. been beating this drum for a while, but Seahil shares some great examples of how it's made his life better. Ladies and gentlemen, this is a great one. It's Sahil Bloom. You first peaked my curiosity. I saw a thread you've written on Twitter and then I looked at your bio and it said a couple things that I really liked. One, writing threads to demystify the world, investor, advisor, and creator. And then this next part really got me. Gave up a grand slam. on ESPN in 2012 and still waiting for it to land. So I was like, okay, this guy, I like this guy and I don't know him yet.

Could you share more about a little of your backstores? I guess going to Stanford and being a baseball pitcher and why you thought, let me just jab myself a little bit with my Twitter bio. Yeah, yeah. Well, I appreciate you having me on. This is awesome. Been a big fan of the content you're putting out. So I'm excited to be a part of it now.

But no, I mean, the genesis of all of that was like, I generally think that people take themselves too seriously. And we all have a tendency to do it, right? Like, especially while you are pursuing something that you think is meaningful, you know, you're achieving things that you think are meaningful. There's just a tendency to like get really buttoned up and serious along the way and stop, you know, stop having the ability to make fun of yourself. And so I, you know, I have this like great group of friends, a lot of my baseball teammates from back in the day. who like, no matter how far any of us make it in life, the exclusive purpose of when we get together is making fun of each other. And so I sort of just like have adopted that ethos in my own life that I just can't take myself too seriously ever. And so the bio is kind of a, you know, a jab in

that direction of like, you know, I was accomplishing something that I thought was great. I was playing on this, you know, big stage and at this great level. And, you know, I had this horrible moment. I gave up a grand slam on national television, lost us, you know, a chance at playing in the college world series. It was like one of the worst moments of my life at the time. But being able to laugh at yourself, kind of on the back end of that stuff, I think it's such a powerful thing. You know, and there's also a lesson there in like never getting too high, never getting too low. The week before that, I mean, the context to it is like the week before that we had played in the regional championships. And I had closed the regional championship game, got a, got a save in the regional

championship game, like 10,000 people in the stands, you know, the highest moment of my baseball career to date. And I remember coming away from it being like, man, I am so good. Like, I really thought, you know, it's like the Giannis quote from a few weeks ago. Like when you think about the past, that's all about your ego. And that was how it was. I was like, man, I did this. I did this. Like, look, I'm coming. I'm getting better. I'm going to get drafted. And then the next week, I gave up this absolutely massive grand slam to lose my team a chance to go into the college world series. And it was that exact example of like, you get too far ahead. yourself, you get too high, you get knocked down. It's just what happens. And so you need to be able to

focus on the present and never get too high, never get too low. So that's always just really resonated with me. How do you, uh, so I have a somewhat similar college story. I coming out of high school, I went to Miami of Ohio here in Ohio, obviously, the Mid-American Conference. And I happen to go at the exact same time and play the same position as Ben Rathlisberger. And, And a bunch of people at college coaches, others called me back after, because Ben committed about a week after I did. And they said, hey, dude, you don't want to go there. Like, it's not going to work out for you.

And of course, like, I'm sure you're the same way when you're 18. You're like, you guys have no idea what you're talking about. I'll beat them out. And I think, though, the great lesson that I learned from that experience of battling it out for two years and maybe having this, this belief in myself that I somehow could win this job, even though I, like from the first day, I probably was never going to win that job, but I thought I was. But I think it's that you, you know, you do everything you can to make it happen. And the world doesn't necessarily care because the coach is going to play the guy who gives the team the best chance to win.

In this case, the late great Terry Hepner made obviously the right decision when he named him starter during our second year at Miami. And I think there's, those are awesome lessons like it. So I'm curious from giving up that grand slam. It sounds like one of the toughest moments of your life at up to that point at least. But especially in your formative years, having to bounce back from things like that. Like, what have you learned from that grand slam that has made you better in what you do today? Yeah. You know, it's interesting.

It's like you hear about those big public failures and those moments, right? Like I talk about that one because it was a big moment. It was on TV. It was, you know, big game, whatever. I actually think the like private failures are even more impactful in terms of how they how they kind of create you and shape you. I think about one of the most impactful ones for myself was like the day I showed up at Stanford campus. I was a freshman 2009. And, you know, I had grown up in a small town in Massachusetts.

I was like the ultimate big fish small pond syndrome. Like, you know, I thought I was hot shit, man. I mean, like, excuse my language. But like I, you know, I thought I was really smart. I thought I was a great baseball player. I got a scholarship to go to this great school. And I got to campus the first day and just got like kicked in the gut. Academically, athletically, I mean, everything, right?

Like I went to class and realized I wasn't that smart. You know, I went to baseball practice and realized I wasn't that good at baseball. And so I remember like freshman year was such a grind because it was like the first time in my life that I had really had to experience on a daily basis failures. And in hindsight, you realize that that kind of stuff is crucial to forming and shaping who you are as a person later. The fact that you were able to like just keep pounding your head into a wall, keep pounding your head into a wall, keep pounding your head to wall, until finally you break through. And you didn't really know when it was going to happen. There was no end in sight. It might have never happened.

It's like that idea of, are you willing to sprint when the distance is unknown, which I've always loved. It's resonated with me. It gives me chills even when I like see people. talk about that or quotes because it's so powerful. Like how much are you willing to just keep running when you have no idea how far you're going to be running? And those were the moments. I mean, none of it was public. It was like practices or going to class on a daily basis and just like being willing to just get knocked down every day and get back up. There's nothing more powerful than that in the long run than if you can kind of like form your character around those type

of, that type of ethos. Has anything like that happened now? because I think sports and especially going to school like Stanford for you probably were great learning tools. But as then you transitioned to post athletic career, you're into the business world, you're investing, you have a job, you're doing things on the side. Can you think of like a moment where you drew from that and it made you better in this more professional world that most of us are in now since we can't play sports forever? Yeah. I mean, every day. It's like your career, your life, like it's all about how you bounce back from failures. No one has the privilege of only succeeding.

If anyone tells you they do, they're lying or they're in such rare air that I can't even relate to them. So, I mean, I remember like my first job, all of the failures that came with it. You screw stuff up. What was your first job after playing baseball? I went straight into the investing world. I got hurt my last year at school and thought I was going to go play professionally. It got taken away from me. probably for the better because I wasn't all that good in the grand scheme of things.

But I went and took this job in the investing world, didn't know a lick about investing. And so I knew I was just going to have to do the same thing. Like, you know, pick up and pick up and just start grinding with it. And I just remember like every day there was something I was screwing out. I'd forget to do something or make the same mistake twice. And the ability to actually like take those pieces of feedback in and not crumble from them is such a massive advantage in life. So many people that I saw and still see a lot of young people entering the work world, they can't take critical feedback. You like give them one piece of

constructive feedback, not even critical, constructive. Like, hey, I want to make you better. Here's one, two, three things that you could do to make your, you know, performance better. And it's like they crumble almost because their whole life, they've been only succeeding at things. And they've only gotten straight A's and they've been at the top of their class and they went to X school or whatever it was. They never had to deal with that like, I'm back. at something, how do I pull up and get better? And so I just think that like those moments, especially as a parent, I think about it for, you know, when I eventually, God willing, have children and I'm raising them, what do I want to instill in them? And that's one of the biggest things

to me is like, let them fail, let them fall on their face. And it's terrifying as a parent, I imagine, easier said than done. But like those moments of failure and those things that I had to, you know, get smoked by are now like the greatest experiences, the things that I wouldn't trade for the world in terms of forming my day-to-day perspective and character. You are an active angel investor. So first, you can, for those who don't know anything about that, I'll ask you to kind of define that for a second. But the second part of the question, which I'm going to ask at the same time, is when you're

looking to make an investment, like what are some of the must- have qualities and or behaviors in a person that you're going to invest. And I know the idea is probably important or their product or whatever it is that they're doing product market fit or if you're so early, you might not even have that yet. But I'm really, because I think of the best investors when I hear what they say, they usually say something like, I invest in the person first before whatever it is that they're doing. I believe in that person regardless of what they're doing. So I'm curious, CEO, from your perspective, what are some of those must have qualities in a person to back? Yeah.

Yeah. So, I mean, first off to your first question, angel investing, I think it's like this term that people start throwing around a lot. It's like, you know, effectively, it's just that you are an individual, not a investment fund, and you are providing money to startups is the right way to think about it. And I don't know where the term angel officially got coined, but, you know, you're like, supposed to be like, they're saving grace. It's far from that. You know, you're just, you're buying into a person and an idea and you're providing capital for them to go and execute in the very early days, generally, before they can go get a venture fund to back them or whatever private, private fund. And then to your question on what you're looking for, I mean, I think the like resilience and

grit is probably the number one thing. And the reason I say that is because startups and entrepreneurship and small business in like all of these areas, you're just going to get knocked around. It's just the reality of life is that nothing is ever up into the right in a straight line. And so if you're investing in a person, you're investing in their idea, the idea can be as good as you want, but it's going to have struggles along the way. Jeff Bezos, like the struggles along the way of Amazon, you look at how much wealth he's accumulated. It's because he was literally the only person that has held Amazon stock for that entire time. No one else could stomach those like 60% drops that the stock had because of massive business, you know, like issues over time. It was resilience.

It was like you stick with it and you continue to find a way to win in the long run. You like zoom out of the short term issues and are able to kind of see the vision and see where it's headed and what I'm supposed to be doing. And when you find that in an entrepreneur, it's really hard to like ask the question that makes you figure out that they have it or not, but you can feel it. Like when you talk to someone, you can really feel it. And I'm by no means some expert. I'm the, you know, there are legendary investors who I'm sure have this like sixth sense figuring out whether an entrepreneur has that it factor. But I think that is just like the most critical thing. Like is this person just willing to die before they fail at this business?

And there are just people out there that have that, that are just like that. And you just know, that's not even an option for them. Like this business that you're backing could completely collapse and they will somehow find a way to like Phoenix out of the ashes and start something else that ends up being even more impressive. So, yeah, a long way of answering your question, but I think resilience and grit are the two. You've done this more than 25 times from what I've read.

So when you think to each of those 25 plus decisions, like can you take us inside the room like i don't know or or or zoom or the calls or like how do you go from oh okay this is an opportunity to all right i'm giving them money like can you can you can you i'm fascinated by that process like how does it work yeah i think it depends on like first off it depends on if you're in the covid you know pre-covid or post-covid world because a lot of the okay maybe sure both yeah yeah i mean pre-covid a lot of this stuff is driven by relationships and in a sense, it was easier as an investor then because you got to spend time building relationship with these individuals that you were going to eventually back. And so you had more data points,

right? Like you saw how they interacted with other people. You saw how they responded to different questions, challenges, things that were happening over just like a longer duration. In the post-COVID era, a lot of this has been done by Zoom. It's like this. You're on a Zoom with someone. And so they have their like, you know, an entrepreneur that's really seasoned has their pit. and they know how to run through it. And so I've personally found, like, if I'm doing a call with someone, I already understand the idea. I'm interested in the idea in the business.

I believe in the long-term vision of it. So I personally try to take it more towards like, I want to get to know you. You know, tell me about a time you got your ass kicked type thing. But the other reality to it is like, I'm not an investment fund. I don't have, you know, limited partners, LPs that have given me their money to invest on their behalf. It's my money. And so, you know, when I do it, I want to get comfortable. And the burden of that is different. And I reach that kind of burden of proof in different, you know, amounts of time depending on the person. I've gotten on a call with someone in like two minutes in

said to myself, holy crap, I got to back this person. I don't care what the idea is almost. Because like, I need to back this person and they're going to figure it out. I had that with a, with an entrepreneur recently. And I actually didn't even think the idea is that good, what he's working on, but I just want to invest in him because I think that he's such a killer in the long run. But it just depends. It just depends what, you know, kind of what the circumstances are around it, how long it actually takes you to go develop that comfort around an idea. The other thing to mention, which people have probably seen in the news, is like the market is so frothy and hot right now. Yeah. And there's so much capital out there that these things, like the timeframes around them

have just compressed and compressed and compressed to the point where, you know, most of them, if you can't make a decision quickly, you're just, you're not going to have an opportunity to invest in the thing. You know, the like investors that are stealing everyone's lunch right now are the ones that can just move really quickly, you know, and send a, decide to say, let's go. Totally. Like, they've done the work. They've done the prep in advance. They know the industry. They know the market. They know the business. You know, like, the competitive landscape. And so they're basically just like check the box on a couple of things that they really want to figure out. And then they can just roll and make a move on it.

So how about let's make it personal? So my current kind of investing strategy is I have set amount of money that goes to my financial advisor every month. And it's kind of automated and I don't really think about it. And then I just let compounding go to work, right? The best way to get wealthy writers just don't interrupt it as Charlie Munger or Warren Buffett might say. And I know that's, and I'll continue to do that no matter what, but I am curious about this. And I think other people are too. So let's say Seheel, I called you. I'm like, dude, I want to do this. I have this set amount of disposable money that if I lose it, I lose it, it's okay. How can I get started? So what advice would you give to me if I'm like, I want to do this part of what you do? Yeah. I mean, look, the,

my first advice would be don't do it. Just keep compounding. Because the reality of most of this, most people want to say they are an angel investor. And it's become this like, it's like a flex almost. It's like a LinkedIn flex where you're like, you want to say that you're an angel investor. The reality is like the vast majority of those investments go to zero because they're startups and they're like really risky. And so for most people, probably, myself included, the like value maximizing thing to do over the long run would be to take all that money that you were going to angel invest and just put it into the S&P 500 and let it just go up over the next 40 years of your life. And you'd probably like on an expected value basis,

that'll leave you the best off. My personal opinion on it always and why I do a lot of it is I learn so much from these conversations, from the people that I get to associate with because of it, from being around these businesses, from helping them. I mean, for me, I could lose all the money that I've invested in all this stuff, every single dollar. And I think it would be a net positive return to me because of the, like, the actual intellectual returns that I've gotten on that capital that I've put out beyond the financial returns.

But on a purely financial basis, I think it's like the burden of wanting to get into that is very high. The challenge, so if you said, okay, I understand that and I want to do it, it's all about deal flow. What are you actually seeing? And so therefore, what can you execute against? The challenge with the venture world and with angel investing in general is that it is the ultimate game of adverse selection. The deals that want you to invest in them are typically not the ones you want to be investing in because they're the ones that no one else has backed. Right. Like if there's some unbelievably hot company that can raise money from anyone in the world, like five years ago, maybe not now, but five years ago, if they had come to me and said like,

Sahel, we want you to put in some money into this, my first reaction would have been like, why? Why do you want me to? I'm like some random analyst at a, you know, fund at the time. Like, what about what is making you want me to invest? And now it almost like set off alarm bells. Now it's a little different because I can help them with a bunch of things. You know, I have a platform. I can talk about them publicly. I can get them exposure. And so now it's like, I'm in more of a, you know, real position to add value to that. them. And so I might be able to get into things that way. But like for a new person starting angel investing, every deal that you see, you almost have to have your initial reaction be like, why am I so

lucky? Is this actually a really good opportunity? Or are they just showing it to me because they can't get the money from anyone else? Interesting. Yeah, it's like the very beginning of when people started asking to like come give talks. I would talk to other more experienced speakers. And I would say, hey, you have a speaking agent, you know, should I, should I get one of those? And they said, trust me, the speaking agents will start reaching out to you the moment you don't need a speaking agent anymore, meaning like the book you kick. So it's just weird how it, how the things work. And that's exactly how this has worked now that multiple years have passed where I don't need the inbound person or the person out there doing it. It'd be just kind of like an admin person.

It's not worth giving all that percentage for that. So I handle it myself. It's kind of interesting how the world kind of works that way. Totally. Yeah, I mean, that's a great analog. But there's like, there's so many analogs like that, right? Actually, a lot. I mean, it's funny because the, uh, the, like common adage within the financial world is that, like dentists have made the best marks for like some of these funds to go and try to raise

money from because they had, they met the accredited investor thresholds, which are what require, you know, you're required to meet in order to invest in these private placements. But they weren't particularly knowledgeable about financial things. because they had pursued a life of science and medicine. And so those were the people that were like typically falling victim to. And it was obviously generalized, but that was like the thing that everyone would talk about where like dentists were the most prone to falling victim to these like random scams that were coming up within the finance world.

Shifting gears a bit. And I want to talk about writing. There's a great Boston Globe story that talks about this, written about you. Great picture with you and Tim Cook. But a lot of, I feel like, I mean, I became aware of you because of your willingness to ship work publicly, to learn in public, to share what you're learning, and to be a fantastic storyteller, whether it's through tweet threads or your substack. Can you first, from a leadership perspective, let's talk about from a leadership perspective, why should every leader have some form of a writing practice, whether they decide to publish it or not? Great question. Simple answer. When you write, you think better. I just think that writing is the best way to expose gaps in your thinking and where you're thinking is falling short. It is impossible, virtually impossible, to write down everything you know about an idea and not immediately see the gaps in what you know about that concept. And so for me, I mean, to make it real, like when I want to go write a thread or write a newsletter piece about some new topic, say inversion, it's like this mental model that I use quite a bit, I can go and write down a piece about it.

And then I'll read it and realize, oh, my God, there's like these massive gaps in how I'm understanding this. And I wouldn't have known that. I would have thought I understood inversion. Like, yeah, I understand it. Because your mind tells you that. You're just like, oh, I get it. I don't need to read more about this. And when you write it down, suddenly it becomes very clear to you where those gaps exist and how you can go fill them in.

And so as a leader, I just think it's one of the most important things you can do for clarifying your thinking on any given topic. The other piece is it makes you better at everything you do. When you write clearly, you communicate more clearly. You're able to be more succinct in everything that you're putting together. I mean, my Twitter writing habit started with Twitter, it's become. I'm a newsletter writing habit has made me a better investor. It's made me a better husband. It's made me a better friend. I just because I think more clearly and I think in more concise terms, I have more value add and conversations that I have with people because I'm able to just like

draw upon these things that I've written about. And so I've learned them more effectively. It just has this massive spillover effect across all these realms of your life. I sold a book deal on management to my publisher McGraw-Hill. I remember in the book proposal, you know, you write like a sample chapter, but a lot of it's kind of the marketing. That's what, that's how a proposal sells. Like, can this dude sell books? And we're going to say yes or no. The idea, yeah, they want it to be good enough. But then you get the deal and then you have to actually write the book. and I didn't fully realize how little I actually knew about the topic that I had just sold a book deal until I was forced to go really deep. And so this is why I push all leaders.

That was one of the greatest learning tools in the world. And so I pushed all leaders right. I mean, I like if you're going to publish. But even if you're not, you should still write. And second, put yourself in the position of being a teacher. So anytime like you're going to give a speech or you're going to meet with a mentee or you're going to try to help, let's say a founder in your case, you're not going to want to not be a value add. So leading up to that meeting, you're probably going to really like, wait, what do I think about this? How am I going to help this person? What can I do? That process of preparing so much learning happens. Then you share the advice and you get immediate feedback if it was useful or not and you can adjust moving forward. I feel like you're You seem to always be in the mode of being a teacher, and that seems to be a great learning tool for you, I gather. 100%. I mean, it's funny.

Like, people have told me over the course of the last year that they've learned a lot from the things that I've put out in the writing. And I think that's amazing. First off, I'm absolutely, like, I have so much gratitude for the era that we live in that I can, like, put things out there and that globally it can have an impact on people. I mean, you like the responses I get from people in India and in Africa and all these places. Like, it's just incredible to me. And I am still blown away by it every day. The thing I always say back is like, I'm actually learning alongside you about all of these things. Because I can't even describe how much smarter I have gotten in the last year from doing all of this writing that was from the outside looking in, looked like me teaching.

It was actually me learning. And it's the most selfish thing I've ever done candidly because. I've done all this writing and, you know, people view it as all this time that I've put out to to help others. And that was a huge inspiration and motivation around it. But I've learned so much from doing it that like the downside to me of writing all of these pieces and doing all of this was that I learned a lot. And the upside was limitless. And so it always just felt like that's a pretty good asymmetric trade I can I can make there. One of the things that you're really good at is is writing great threads. So those who are, I guess not everyone's on Twitter. I find Twitter to be

one of the greatest learning tools in the world. It's also been a great networking tool for me to meet people. That's how we met. And part of what makes your threads so good is that you've become a phenomenal storyteller. So I do want to get specific on the threads thing, but I know not everybody cares about that. I do, but I know not everybody does. So let's start with the storytelling aspect of it. How have you worked on and what is the makings of someone who is a great storyteller?

Like, how can we do this? Yeah. I mean, for me, storytelling is a kind of built skill. A lot of people think that you're either a good storyteller or you're not. And I just push back on that. I read, I just spent a lot of time reading all of these different pieces on the principles of great storytelling from Disney and Pixar and these places that I consider to be foundational storytellers. And I think honestly, you can study that. I don't write about fantasy worlds and different realities,

but those principles run through every area of your life. If you're an entrepreneur and you're running a business and you're constantly telling stories, you're doing it to your investors to tell them to give you money. You're doing it to your employees to give them that vision of what you're building and why it's so exciting. And so it's just a foundational skill on a day-to-day basis. And I just focused on how can I just keep getting better at it. My mom is an incredible storyteller.

Everyone that knows her will say that about her. She just has this like air about her where she she just kind of captivates a room. And I think maybe I had a little bit of that from her naturally. Like I was always the guy in the locker room that was telling stories and like, you know, had people laughing. I wasn't like a clown, but always had some story that I would like to be telling. And so I've kind of tried to take that and like put it into my writing. Like when I'm writing about a topic, how can I infuse a degree of personality, of emotion, of novelty, something that just makes it more than a dry educational piece.

Because you think about like as a child, you have all these textbooks and these things that they're making you read. And it's really hard to absorb stuff that feels that dry, mundane. It's much easier to absorb something when it feels relatable. It feels like it has wit. It feels like it has novelty or emotion and it's grabbing you in some different way. And so I think it's just so important to develop that, to hone that skill. And really to just keep improving upon it. I mean, I started this a year and a half, not even a year and a half ago.

I started it. I'm looking at the date. I started at May 12th of 2020. I started writing publicly. That was when I started my Twitter writing as. Wow. Really? It's only been that amount of time.

Yeah, yeah. 14 months or 15 months, whatever that is. I had 500 Twitter followers, like, started, yeah, started putting stuff out. And I like, I objectively think my early stuff was like pretty bad. It was well researched and well thought through, but it didn't have that like extra kind of it factor. And that just comes from storytelling. So let's let's get to the, let's go a step further than. Let's break it down.

Someone who says, I'm not a good storyteller. What, how can I get better? Like what are some of the practical applications or practical things they could take away from this conversation to implement immediately to become a better storyteller? Yeah. I think the three biggest ones. ones for me. Maybe I'm going to end up running over on that. But I think something that elicits an emotional response from the audience, you need like emotion woven into the fabric of what you were writing, saying, speaking, whatever it might be. It needs to grab people in some way. And so when you're

writing it or when you're sketching out your notes for something that you're going to publicly say and the storytelling aspect of it, you need to know what that emotion is going to be. Like, what are you trying to elicit. Is it happiness? Is it hope? Is it inspiration? And the best writers do that naturally. I wasn't one of those like best writers. I had to force it. I would have to think before I wrote something, what is the emotion that I'm going for here? And how do I weave that in and make sure that it's kind of creating that reaction and creating that response? The other piece is novelty to me. It's what is like the oh wow moment that I'm triggering in my audience that's kind of taking them out of their normal, just like humdrum life that I'm hitting them with.

Because that's when you grab someone and then they remember it. Then they're telling that story and they're sharing it with somebody. And now you're bigger than just your one to one of you telling a story to someone else. It becomes like you have this K factor of like shareability of the things that you're putting out there. So I think those are the two biggest. I mean, the other one which is just like table stakes for all writing and speaking is you need to be punchy and concise about how.

you tell a story. Telling a great story isn't about writing a million words and winding it in 40 directions and like making it complicated and using big words. It's actually the opposite. It's like the Mark Twain quote. It's one of my favorite quotes. I didn't have time to write a short letter, so I wrote a long one instead. And I just love that quote because it's so true. Like it's much harder to simplify and write something very clear and short than it is to write some long, winding, verbose piece. And that plays through to storytelling. The best storytellers in the world are the most concise. Every single word is considered. It's thoughtful. I mean, I think that is just table stakes if you want to be a great storyteller and you want to improve your storytelling.

It's like a stand-up comedian's talk about the economy of words. The best of the best. They make it feel like they just kind of just kind of stumble out on stage and start talking. And yet the great ones have handcrafted every single word they say when they get on that stage. So I want May 9th, 2020. Is this the first thread that helped you blow up? And I just want to give an example for people who haven't read this or heard of your stuff yet. And this is how it starts and it peaked my curiosity. A thread on markets.

It is the year 1500 and you enter a market in Renaissance era, Italy. There are buyers and there are sellers. Prices of the various goods are determined by the interaction by and among these individuals. Now in walks Mr. Federico, a man of endless means. Tweet two, Mr. Federico climbs a tower in the center of the market and proclaims, quote, I am a buyer of any and all goods in this market regardless of their price. He climbs down off the tower and exits the market to return to his mansion. what happens in the market when he leaves.

And then the thread continues. So this is what I'm talking about. I'm like, wait, it's like in a book where the good authors make you turn the page. I got to go to the next one and the next one. And the next one. You can't put it down. So this is at the beginning of you. You probably had no followers at this point.

And now you have 240,000 plus. So what's going through your head as you're putting this together now that I shared a real example? Yeah. That was my first one. So I had near and dear to my heart. I, this is like, so it's May 2020,

um, markets are soaring while the economy is still shut down. Everyone's stuck at home. And basically everyone in the world, myself included was like, what the hell is going on? Like how is the market ripping right now? While everyone stuck at home and no one's spending money.

Um, and I was trying to find a way to explain the concept that like what the federal reserve is doing, which is they're going into the market and basically just buying, a bunch of stuff and the impact that has on prices in a market. And I was like, how can I do this in a way that it's going to make it digestible? It's not going to be technical things about buying bonds and what they're doing. And it's going to be accessible to anybody. And so basically, I sat down. I had a few friends from my baseball days texting me, asking me these questions.

And I was like, I need to figure out something that I can just send them. And I can just be like, here, this explains it. You'll get it. And that was how that came to life. And I created that fictional character, Mr. Federico, which is admittedly, yeah. Yeah, admittedly not my best humor, but it got the point across that that's what I was talking about. And, and I wrote that, like, on the floor of my garage, just because I had an idea right then. I wanted to write it down. And I posted it, you know, first off, I called my shot because I told my wife that it was going to go viral. And she, like, rolled her eyes at me and walked away. You know, I had 500 followers at the time, so there was no reason to think so.

And I really believe that, though. You really believe that. You really believed that. I did. Yeah. I wrote it and I was like, I basically just wrote it and I was like, this is really good. This, I mean, if this is a meritocracy, which I believe Twitter effectively is, this should go viral. Like, this is really good. It's thoughtful.

It gets the point across. I think it's really good. And so I tweeted it. And, you know, I didn't have many followers. So it didn't really get much traction at first. And then I sort of hustled a little bit. Like I commented it under a couple big accounts posts. And Chamath, who has this massive following, saw it and reached.

tweeted it and said like, this is good and retweeted it. And so all of a sudden, like, my phone just went bananas. You know, like I went from having 500 followers to 2,000 or something that day. And that was kind of the start of it. I realized like, oh, there's something to this concept of breaking these concepts down in an easy, digestible way for people. And that it wasn't out there. Like in general, I had this perception that the market had split where in the world of finance and the world of business, you have like the really low end, like the TikTokers that are giving you nonsense advice about buying options and like all of that stuff. And then you had the like really high end of people who are just talking over your head. They're like, you know,

basically trying to make you feel dumb because they want you to pay them to manage their money, whatever it might be. And so my decided was like if if this end is the like really crappy like, you know, bicycle and this end is the like Ferrari, I was like, I'm going to be the like Toyota Camry. just like good old faithful gets you from point A to point B sell tons of those cars because they're just very you know they're like a good price point quote unquote and that's what I wanted to be I wanted it to be accessible digestible I wanted anyone to be able to share it and get value out of it and I think I've generally met that you know met that burden that I tried to set out for reminds me a little bit of Tim Urban he's been on the show he writes at wait but Wyatt dot com takes a huge fan of Tim yeah I think

everyone who writes loves Tim because he takes the super complex, makes it simple and is funny. And I think the best writers have that ability to take the complex. They then digest it and synthesize it and retell it in the form of a story. They add some humor and they make the reader feel smarter after having read them, not dumber because they speak like listen to my big words. And that is what I strive for. I think that's what leaders in general should strive for, regardless of your title, regardless of your job. And one of the best ways I think to get better at this. One, first and foremost, like anything else, you just got to do it. Right. You got to get the reps. But then two, and I think a close second is you've got to be reading this stuff constantly. And that's why Twitter

has been a great learning tool for me and I push people towards it because there are some negative things just like anything else in life. But there's so much positive that comes from it. And there's so much out there to learn. And I feel like this is something you've really, it's become part of you. Yeah. Yeah. I mean, to me, it's just about being positive sum. You clearly have that mentality, but the world in my view is a positive some game. When other people win and we have a rising tide and a groundswell of people getting smarter and feeling empowered and inspired by things I'm putting out there, that makes me better off. Like the economy starts getting better. People are making better decisions. They're spending money on things. They're investing in things. And when that happens,

we all win. And so, like, I just have this general positive sum mentality around this stuff where if I can empower people and if I can spend a few hours writing something that, I don't know. I mean, the recent things I'm putting out there are like, it's two million, three million impressions in 24 hours. It's like, that's an unbelievable number of people that I can reach. And if one percent of those people feel empowered and inspired or learn one thing, that's the best university teacher in the world. Like, you can't reach that many people. And so we live in this era where I can do that. And I just am blown away by that fact. And so that's kind of what inspires me to continue doing it is just this like general positive sum mentality that I feel around all of it. You know, I tweeted something about

like starting to genuinely root for others to succeed is this massive unlock in life. And I really believe it. Like the people who I look at who have helped me along the way, who had no reason, like I was giving them no benefit. And I may never give them a benefit, but they still just rooted for me along the way. That just blows me away. And I want to be that person to 10s, hundreds, thousands of others, you know, in their lives so that they feel that same way. Yeah. One of the things I wanted to talk to you about since we have the similar background of playing a sport in college is that we've all we've had experiences with coaches both on the field and maybe like a boss can play the role of a coach as well. I'm curious from your perspective, what have you found like

when you compare and contrast like the excellent coaches who have made your life better in more ways than just maybe throwing the ball harder or more accurate, but they've made you better. What's the makeup of a great coach? both sports-wise and maybe outside of the sporting world, too, in your mind. Yeah. I think the two things for me are in the trenches with the team. That's a common thread in everything, whether that's sports or life. The best leaders, the best coaches, they're in the trenches with their guys. Like, they're never, it's, I think it's the New Zealand All Blacks, like the concept

of like never be too big to do the small things. and the team, the captains of the team, are the ones that have to sweep out the locker room at the end of a game. And I was always taken with that concept. And it's really powerful. And I think the best coaches do it naturally. You can learn that.

But it's just being in the trenches with the guys or girls on the team and feeling like you're fighting alongside them. You just do so much and you want to work for that coach that's there with you. And then the other one is someone that's willing to challenge you, call you out when you're wrong on something, tell you that you're, you know, what you did is not good enough. Because otherwise, you're just never going to get better. I mean, I had, I've had coaches in my life that were, you know, sort of just, sort of just there and like, you know, not going to call you out. If you didn't put in the effort, you should have because you were the star or whatever,

they don't want to call out the star. The best coaches I found were the ones that were like, literally just say to your face, that's not good enough. You know it's not good enough as well as I do. And if you're okay with that as your level of effort, there's, I don't know, I don't know who you are as a person. Those kind of things, you're just like, whoa, it kind of like knocks you back when someone calls you out like that. But those are the moments where you get, you might get pissed and you might be like, how dare they say that to me. But if it triggers that response and you kind of jump in and you're working harder because of it, I mean, man, the impact that can have on a full team when you're doing that. And I always found that. I mean, I've had some amazing coaches and been privileged to have some amazing mentors, people that have been around me in my life. And the common threat among the most

amazing ones is they just push my thinking. They just push me and push me. And if I say something that's unfounded, they're like, oh, you really believe that? You think you've done the work to to really believe that or to make that assertion in that confident of a manner. And normally, you realize that you haven't. And you're like, oh, crap, you know, they're right. I need to, I need to dig in further. I need to spend more time on that. But I think it's, I think it's those two. It's being in the trenches. And then it's just being willing to challenge, challenge the people that are under you. I like that. I know for me from a coaching perspective, they're the ones who pushed me to levels that I didn't even realize I was capable of. And that's because they weren't afraid for me to

temporarily dislike them. I grew to love them deeply, sometimes after the fact. But I, I love the fact that they cared so much that they were willing to upset me because they knew that's what it took to get me to perform at a level. And I would say, I don't think I get a college scholarship without two of my high school coaches. I'm in the exact same boat. My high school baseball coach, who I'm still extremely close with to this day, I was this guy coach John Beverly, small public high school in Massachusetts. And I remember like my freshman and sophomore year of high school,

I had two great seasons, but I was throwing, I don't know, 78, 80 miles an hour. But I was good. I was like, you know, dicing guys up, little, little breaking ball. Yeah, I was doing the whole dance. And I remember at the end of that sophomore season, he called me in and he was like, what do you want to do? Like, what's your vision for baseball? Do you want to play in college?

And I said, like, yeah, I think maybe I could play in an Ivy League. And, you know, that's kind of lower end D1 baseball. I think I could go do that. And he looked me straight in the face and he was like, how about Stanford? how about rice? And I remember thinking like, this dude crazy. I mean, that was like the first thought that went through my mind was just like, this guy's nuts. I'm like a 510, 165 pound right-hander from Massachusetts, public high school in Massachusetts.

I'm throwing 80 miles an hour. What do you mean Stanford? Like Stanford's one of the best baseball programs in the country. And he was dead serious. He looked, I mean, like, I kind of laughed and I looked at him and he was just staring at me. And he's like, if you were willing to put in the work, you have the talent to do this. It's going to be hard. But that's what I expect from you.

doing that. And all of a sudden it was like, oh, wow, someone believes in me at that level. Like this guy who is an informed individual and credible believes in me at that level. And a year later, I had a scholarship offer from Stanford. And I was signing a letter of intent to go to Stanford. And I attribute so much of that to just that one moment where he kind of challenged me. And he was like, what about Stanford? What about Rice? It still blows me away to think about it. not like one of the most impactful moments in my whole life. I mean, in terms of setting the trajectory. And I owe him a massive debt of gratitude. But it's, uh, it's just amazing. It was like one person that believes in you on some level like that and is willing to challenge you

and kind of push you to that level can totally change the trajectory and, and your path. Doesn't that make you want to do that for other people? Totally. I mean, I mean, it's what I try to do every single day. Like I want to mentor people. I want to be that person that had that impact. It's why I think coaches, teachers, we're some of the most underpaid people in the world. Everyone has that one high school teacher or some person that, you know, again, for no benefit, for no monetary benefit helped you and like completely change the course of your life. And we pay our teachers like crap. We pay these like high school coaches like crap.

And the impact they have on young men and women and the course of their life, it's truly remarkable. I think it's it's it's it's it's got to be such a fulfilling and rewarding feeling for them to do it. And I've I've gone back and interviewed. Some even had had a couple on this podcast because as a way to say thank you and just to deconstruct how their mind works. And to me, I love the thought of like seeing something in someone who they believe in themselves, but they maybe their level of expectations are just right like here. You know, they're kind of realistic, but they've got like a ceiling that they've put that it's not intentional.

There's nothing bad. They just they just don't really think bigger. And for for you or me or anyone to say actually Stanford, Rice, that that is realistic for you. I know it is. And here's some things to do to do it. But it is an actual, it's actually in play. And all of a sudden, your mind changes. your mind shifts, your expectation level changed.

And to me, like, he set a standard of excellence for you that we can do. We can do this for people if we care. But that's hard. Like, it's much easier for your coach. Be like, wow, I'm glad you're on our team. Don't transfer. Don't go somewhere else. I love you.

I'm here for you instead. He's like, no, I'm going to push you and raise your level of expectations. Like, what an awesome moment of leadership. Yeah, insane. I mean, it's like the Pygmalian effect. I just wrote about this. It's a cognitive bias. It's like high expectations lead to improved and higher performance.

Someone vocalizing that they have these amazing high expectations for you has this impact where you just want to live up to those expectations that the person has set for. You want to work hard and achieve those things. I don't know. It's funny. Like we go through life and we don't necessarily vocalize our thanks for the people that gave us those moments. I mean, I'm like, I'm going to send my coach this, this podcast because I want him, I want him to hear it. And, you know, like publicly kind of hear the word of thanks.

But, you know, maybe I've said it to him over the years, but it's just funny to think about like how impactful one moment. I don't even know if he remembers that moment, but it's so impactful for me. Yeah, he probably doesn't. You know, he probably doesn't. I've said those things to my coach. You're like, oh, because it's just the way they are. Yeah. You know, like the great ones.

It's just how they're. And they've done it for other people, too, because that's just their standard mode of operation. And I think that I'm glad you said that this is a good kind of signal for people if there is somebody like that in your life. And hopefully there is or hopefully there's more than one. I would urge you to tell them, call them, email them, try to see them if possible. I would urge you. I did this recently with my high school offensive coordinator who became a head coach. I asked him go to dinner.

This was months ago. And we went out to eat. And I just wanted to look him in the eye. He was with his wife. And I wanted his wife to hear it too. I wanted her to hear the impact he had on me. And I just was like honestly told him exactly how I felt. And he had this like look in his eye.

It's like emotional even thinking about this, this look in his eye of like, okay, like good. Like I still want to impress them though. You know how weird those coaches where you still want to impress them? But I just want to make sure he knew it. And then we had like hours and hours of conversation, storytelling, a follow up meeting afterwards. It just I urge people to do that.

Like to call somebody, see them, tell them, even text them, whatever maybe to let them know. Thank you for what you've done for me. Like I don't know if you fully realize how much you've impacted me. And that can be really powerful. Yeah, absolutely. I love it. I love it.

One more thing. I know we have to run, but I'm going to talk about the power of learning circles. Could you briefly describe like the power of learning circles? Because you're a lifelong learner. I'm a lifelong learner. I'm fans of leaders who are learning leaders. And you've written about learning circles. And I get to do this too.

in my daily life. Can you talk about the power of learning circles? Yeah. Maybe I need to write more about this too because it's something people, a lot of people ask me about. My hypothesis is that the best learning is communal. It's not an individual activity. And what I mean by that is when you read something new, you read a new concept, you can sit there and think about it and it's in your head and you've learned something a little bit. But it gets really cemented. It gets much more dynamic and usable when you go talk about it with a bunch of people and you riff on it and you push and pull it in different directions. This idea becomes much more than just a concept that you've read about and you've only heard it one way. And so one thing that

I always encourage people to do and that I've adopted in my own life is develop these like circles of friends, like whether it's a group chat or a, you know, hang out every now and then in person, like groups of people that you can collectively learn with about these things and bring up these ideas. It doesn't have to be formal and you're like saying, hey, this is my learning circle, but groups of friends that push your thinking on things where you can throw out an idea and say, hey, I'm really thinking about, you know, the future of work. What does it look like? I read this cool article about X, Y, or Z and what do you think about that? And they totally disagree. And then you kind of, you know, go at it a little bit and push in different directions. And suddenly you're just like,

you have this unbelievably dynamic set of thoughts about a concept that you never would have had if you had just read the article and then said, oh, yeah, I know about the future of work now. It's just a different degree. You were here and now you're up here. And that's brought about by that collective learning. And so I always encourage people like find your learning circle, find people that you can kind of collectively come together with and learn together, learn in that same way. I love it. Thanks so much, man, for being here. There's so much out there to learn more about you. Where would you send people online? Yeah, I mean, my Twitter is at Sahelblum. Just my name. It's the benefit of having a,

having a weird name. So it's at Sahelblum. And then my, my newsletter is, I don't know, sawhillblum.com, I think. The Curiosity Chronicle, I love the name. Yeah. Yeah, just exploring my own curiosity and sharing it with others. So I highly recommend people checking it out because both your threads and your, um, your substack because I've, I've learned a ton from it personally. So every time like a new thread comes, I am ready. Um, so I really, and your, uh, substack, I really appreciate it, man. And thanks so much for being here. I'd love to continue our dialogue as we both progress. Would love to appreciate it. Thanks so much. Thanks, ma'am.

Now that is a conversation. I love to have continued for hours. And we both intend to do that. After we got to them recording, Seheel said, hey, you got, you have to come to New York City. so we can keep this going, maybe over a meal and a few drinks, and I fully intend to do that. I really appreciate the way his mind works and how deep of a thinker, Sejil, is a few takeaways from my notes. Learning circles, develop a circle of people to collectively learn with push your thinking. This is something I do with my learning leader circles, and it's some of the most rewarding and fulfilling work. I do where I'm able to facilitate conversations, ask questions, ask even better follow-up questions so that we all can learn together.

Then the makeup of a great coach, they're never too big to do the small things. They push you beyond what you think you're capable of. They lift expectations for you, as his coach said to him, how about Stanford when that wasn't even in Sahel's mind? And I'd like for you to take a moment and say thank you to someone who has done this for you, for you. Maybe text them, call them, meet with them, send them an email, write them a letter. I'd love to see you do this and hear about the response from that person when you do. And then why writing makes you better at everything you do. That was a fun part of the conversation. When Sahil said writing is the best way to expose Gap, in your thinking. When you write, you think better, and it makes you better at every aspect of your life. All leaders should be writers. I want to say once again, thank you so much for continuing to spread the message and telling a friend or two or two, hey, you should listen to this episode of the Learning Leader Show with Sahil Bloom. It will make you a more effective

leader. And because you continue to do that, and because you continue to write reviews and rate the show hopefully five stars on Apple Podcasts. You are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so much. Talk to you soon. Can't wait. I recently found an exciting new investment opportunity, Blue Chip Art. Now, it's traditionally only open to billionaires because of the high entry cost. But one startup is making it available for everyone. Masterworks.io lets you invest in multi-million dollar works by artists like Banksy and Monet. Contemporary art prices outperformed S&P 500 returns by 174% from 1995 to 2020. The total art asset class is currently estimated at $1.7 trillion and is growing by another

trillion over the next five years. Now, demand is high, but I've worked with Masterworks to let you skip their wait list by going to masterworks.io slash learning. That's masterworks. dot i.o slash learning. Also, please see important disclosures at masterworks.com slash disclaimer.