My First Million - Billion Dollar Business Philosophies With Hubspot Co-Founder Dharmesh Shah

Episode Date: July 12, 2022

Sam Parr (@TheSamParr) and Shaan Puri (@ShaanVP) talk to Co-Founder & CTO of HubSpot, Dharmesh Shah (@dharmesh), about why a bad economy is a good time to start a business, creating an alternative to Wordle, and the trillion dollar Venn diagram of success. Also, want $5,000? Check out the My First Million Clips contest. ----- Links: * HubSpot * Why to Start a Startup in a Bad Economy article * WordPlay * Maven writing course * Shaan tweet about starting the next Pixar * Do you love MFM and want to see Sam and Shaan's smiling faces? Subscribe to our Youtube channel. * Want more insights like MFM? Check out Shaan's newsletter. ----- Show Notes: (02:10) - Why renting is better than owning (25:20) - Framework for three types of employees (35:05) - Why Dharmesh built WordPlay (01:07:55) - Driving value through an intersection of skills (Trillion dollar Venn diagram) (01:12:10) - Why Shaan is starting the next Pixar ----- Past guests on My First Million include Rob Dyrdek, Hasan Minhaj, Balaji Srinivasan, Jake Paul, Dr. Andrew Huberman, Gary Vee, Lance Armstrong, Sophia Amoruso, Ariel Helwani, Ramit Sethi, Stanley Druckenmiller, Peter Diamandis, Dharmesh Shah, Brian Halligan, Marc Lore, Jason Calacanis, Andrew Wilkinson, Julian Shapiro, Kat Cole, Codie Sanchez, Nader Al-Naji, Steph Smith, Trung Phan, Nick Huber, Anthony Pompliano, Ben Askren, Ramon Van Meer, Brianne Kimmel, Andrew Gazdecki, Scott Belsky, Moiz Ali, Dan Held, Elaine Zelby, Michael Saylor, Ryan Begelman, Jack Butcher, Reed Duchscher, Tai Lopez, Harley Finkelstein, Alexa von Tobel, Noah Kagan, Nick Bare, Greg Isenberg, James Altucher, Randy Hetrick and more. ----- Additional episodes you might enjoy: • #224 Rob Dyrdek - How Tracking Every Second of His Life Took Rob Drydek from 0 to $405M in Exits • #209 Gary Vaynerchuk - Why NFTS Are the Future • #178 Balaji Srinivasan - Balaji on How to Fix the Media, Cloud Cities & Crypto * #169 - How One Man Started 5, Billion Dollar Companies, Dan Gilbert's Empire, & Talking With Warren Buffett • ​​​​#218 - Why You Should Take a Think Week Like Bill Gates • Dave Portnoy vs The World, Extreme Body Monitoring, The Future of Apparel Retail, "How Much is Anthony Pompliano Worth?", and More • How Mr Beast Got 100M Views in Less Than 4 Days, The $25M Chrome Extension, and More

So this is what I call it the trillion-dollar Venn diagram of success, right? I just made that up. So you draw those circles of your skills and say, okay, well, I am now not like one in a million. I'm one in a billion, right? Or one in five billion, whatever that is. And if you can convert that into some kind of monetizable business thing or whatever, that's when magic sort of happens. So that's kind of thing number one is like, what's your thing?

What are your skills? And what drives the value, how much value will that intersection create is two things. one is how rare is that intersection, whether it's two circles or three circles or whatever. How rare is it? And then the other one is... So on the pod right now, we've got Darmash. Darmash is the founder of HubSpot.

He's a... Your technical title, CTO, right? That is correct. I see you more... I think this means that you have to do the ad reads for your own company today. Why are we talking about HubSpot? You do the ad reads. You tell people why to buy it.

You're talking about HubSpot because you guys do a much... better job. I am terrible at that. I'm terrible at the promotion side of things. Sean, do you, you're renting a house right now? Yeah. And Darmash, you do not rent though, right? Not anymore. I did for a long, long time. I'm a big believer in rentals as it turns out, but I, I'm staying in Brooklyn for the summer and I rent a furnished house and it, or an apartment, and it is so much better than owning a place and having to worry about stuff all the time. It is so much better. I think I'm with the renting train, I think now. Like, I've kind of been there, but like, I actually love it more. Do you like it? Because, Sean, you owned a place in San Francisco for like four years,

and then now you rent again. Way better. In fact, every time something breaks, I now just have joy to be like, let me call somebody else. It's their problem. It's their cost to fix. They have to arrange it. They have to do whatever. And I don't have to think about it. Plus, also in California, property taxes are like insane, or like in San Francisco because the, you know, the house price is so high. So, you know, even if you tried to do the calculation, it's so hard to beat just this annual property tax every single time on rent. Wait, so, Damesh, if you had the choice again, I mean, I think maybe perhaps you bought because like your wife wanted to or your kids wanted to, but if it was up to you, even with

a family, would you be a renter? If it was up to me, yes. Because just the decrease in maintenance and wear and tear on one psyche and soul that ownership bestows upon you is just not worth it. That's my thing. It's just like, like, I don't want to worry about those things. I want to get as close to, like, living in the matrix as I possibly can, right? And renting is a step closer to being in the matrix.

We don't have to worry about physical things and atoms and things like that. It's like, that's somebody else's problem. Why you show up? How many people in your socioeconomic, like, ballpark, like, you know, founders of multi-billion-dollar companies or people like you, do you think also rent? because I think that'd be a, if it were a fair amount, that would be fairly shocking to a lot of people, but do you know a bunch of people that are similar to you that are still rent?

I know people that are similar to me in terms of that they would prefer renting, because I've talked to them about this, but almost everyone I know now, once you get a family and once you have like other things that you're trying to factor in, for instance, you know, one of the things my wife loves gardening and loves having a yard, and that's kind of hard to do in a rental. Not that you can't do it, but it's...

Right. One thing that a guy told me who's... similarly, you know, I think he's probably got like a 10 or 10 or 20 billion dollar house. He was like, he's like, renting is amazing until you want the, until your wife wants a specific house. And then once your wife wants a specific house or in a specific neighborhood, that neighborhood, like higher end neighborhoods have no rentals. So you just can't get into that neighborhood, which means you can't have whatever. So then you're forced into a different path. And so I thought, you know, it's a, it's a version of good problems to have. So we'll count it that way.

All right. What are we talking about? where should we start? Well, you have a few things left over from the last episode, Sean. I don't know if we want to jump into some of those. Let's do one. Let's do one because I think you will have a take on this. So have you ever read, I don't know, do you know Paul Graham, by the way? I do.

We're not best buddies or anything, but I do know of him. I've met him, yeah. So he's from Boston, right, or Cambridge? Cambridge, yep. Yeah, so you guys know one another. He wrote a blog post back in 2008. It was October 2008. So this is like right after the crash.

And it's just if you go to Paul Graham.com slash bad economy is the name of the blog post. And he makes this case where he goes, the economic situation is apparently so grim that some experts fear we may be in for a stretch as bad as the mid-70s, which is when Microsoft and Apple were founded. And as those examples suggest, like a recession may not be such a bad time to start a startup, which you've heard before, but I thought there's one interesting part where he goes, I'm not saying it's a good time either. The truth is more boring. the economy doesn't matter much either way for a founder starting a startup.

And I actually thought that was a really good point because I hear this so much. I'll talk to kind of young founders and they listen to Twitter and they listen to podcasts and they listen, you know, they listen to kind of these like a lot of it's like, you know, VCs who are, you know, also pandemic experts and also, you know, macroeconomists as well. And so they hear and then they sort of start to adjust their plans and their mental models and like their room. for everything. It's like, dude, if you're a startup, you're like an ant in this world. Does the aunt care what's going on with the presidential election? No. Like, you basically just need to build a product. You need to carry your little piece of dirt. It's like, build a product, get a customer. Get 10 customers. Like, it doesn't matter if the economy is bad. If you can't get 10 customers, it's not going to work anyways. And so I thought it was a

great little blog post talking about like kind of starting a startup during the downtime, which is where I think we're about to or we just officially entered a recession again. So I was curious, Darmes, do you have any thoughts on that? Yeah, so my position is I lean more towards kind of the Paul Graham and the spectrum, which is I think it's either neutral that it doesn't matter. It's one of the things you're suggesting, towards positive. And the positive elements of being in a kind of downturning economy or recession is that things become available that would not have been

available to a startup before. Like talent, it's like, oh, well, there are people sitting at meta Facebook or sitting at Google right now that may be re-evaluating their lives or they may have just been let go from a, venture-backed company that raised $200 plus million, right? So now you've got this talent that's coming on the market that might not have come on the market before. Things that were super expensive, like buying Google

AdWords or certain marketing channels because you have this glut of money and a glut of venture capital. I think of venture capital as a very efficient machine of turning like money from LPs into Google AdWords rep, right? They're just a conduit between the two. And as in a downward economy, you're going to get

less of that kind of glut of money flowing in which drives the cost overall down. for certain things that I think are important to entrepreneurs. So I'm generally net positive. That end up economy is actually a relatively good time to start a startup. For like the last 18 months or, you know, whenever like the last 24 months, whenever things been booming, I've, my wife works at Airbnb and, you know, I've got a lot of friends at work at HubSpot and all these.

And Sean was at Twitch. So we have like some perspective on how on the salaries of big companies. And I've seen some of these salaries and they are crazy, crazy, crazy, crazy, crazy. As the, as like a leader and the biggest shareholder of HubSpot and you like see these, see these numbers, are you thinking to yourself like this? Like, we can't afford to pay someone like an entry level person, $250,000 a year. I don't know how this is going to work. Like what's your perspective on that when these salaries are going so high? And now it's like a little bit normal, more normal.

Yeah, but as a startup, I mean, you can't afford those salaries anyway, right? Unless you're one of those kind of rare exceptions that has 50 plus million dollars going out of the gate, which is very, very rare. And so, you know, one of the things a founder has to kind of get good at, it's convincing really smart people to do this irrational thing, which is join you in your startup, right? And if you can't do that, if you can't make that sale, which is the most important sale you'll make, is being able to kind of attract people and that it's customers.

It's not going to work. So you have to do one up, you have two things, either recognize kind of superstar talent and give them something they can't get because it's beyond competence. It's like, oh, you'll learn more here. Oh, you're going to do your own startup someday. This is a place to get your startup MBA, because you'll be exposed to a bunch of things.

You'll meet your future co-founder of the company, those kinds of things. Either you have to do that, or you have to say, I'm going to be really good at identifying diamonds in the rough. People that have not made it to the 200 plus $300,000 plus salary yet, but they will someday. I caught them early in their kind of evolution,

and so I can get them. There's that. So it has to be one or the other form of arbitrage. Otherwise, you can't play the game. That's just not, like, it's viable. I'm doing, when you're saying that, it's like resonating so much because it's basically, all the three things we just talked about I'm doing.

It's like I started the Milk Road in January this year. And so it's been, it's about to be six months or it's been six months. And it's like, here, let me start a crypto company right when crypto crashes, you know, like 70%. And at the beginning, Ben even my co-founder Ben, he was like, you know, the only thing I can see going wrong is if crypto goes in a bare market. I go, well, crypto is going to go to a bare market. Like that's like one of the few certainties of crypto is that it goes up and down. And when it does, it is dramatic in both ways. It goes from the elevator is dramatic in both ways.

And I was like, you know, so it's just a question of like, do you, what, do you think that kills it or do we just make it through? Like, that's really all we have to think about here. So that was the first part of starting in a bad economy. The second one on talent was I recently hired this guy. And he quit a pretty well-known venture back company that I think it just raised maybe $50 or $100 million. And he joined.

And I had talked. talked to him a little bit before he joined. Like he was thinking about doing his own startup. He had traded a couple emails. Nothing serious. Just he, he was wanting to be to use his product. Then he took a job at this place.

All right, whatever, I forgot about him. Then he emails me, and I shared this on Twitter. He emails me, subject line, I have made an irreversible decision.

And I was like, okay, I got to click this. What's inside? And he's like, I just quit my job. And I think you should hire me. And I was like,

okay, direct into the point. And he tells me why, blah, blah, blah. And so I was like, all right, boom, I'm sold. very bold approach. I already liked your hustle before this because when you were hustling to try to get me as your customer, I was like, this guy's good.

So, okay, let's do this. And I made him a job offer, which was not like, you know, a Silicon Valley job offer. But the guy lives in San Francisco. He was working for his Silicon Valley startup. So he was like, oh, dude, that's like a 50% pay cut. And I was like, and I didn't say this out loud. But in my head, what I felt. I told him, I was like, that's what I could afford to pay right now.

And like, look, you come crush it. The sky's the limit. But like, that's what I can pay you right now. A sight unseen. And I said, and in my head, I was about to tell him the line that I heard from Warren Buffett. You guys probably heard the story. But when Warren Buffett goes and tries to work for his, you know, kind of hero or whatever, Ben Graham. And he's like, you know, I'll work for you for free.

And Ben Graham goes, your price is too high, sir. Which is, which is the truth, which is the idea that you got to shadow Ben Graham and work side by side with him every day was you should be paying for that. if you really want to be like a successful investor. That's how I felt. And I didn't want to say it because it's kind of arrogant, but it's like, dude, if I take you under my wing, my team is like three people.

If you become one of those three and you're working out of my, he came out of my house yesterday, you're sitting by me working out of, you know, side by side every day. Like really, I'm providing more value to you than you are providing to me at that point. And like there's still a, you know, I appreciate the value you bring,

but let's like the dollar amount is like, the salary dollar amount is not the value you're getting. And I think he knows that intuitively, and that's why he said yes, but like that Ben Graham story always stands out to me. No, no, he's a young guy, just graduated from college. Here's the thing. I think people have a couple of thoughts on that.

One is the salary slash compensation is just one vector of value that you get from a company that you join, right? Another one that you get is you get the learning, whatever it is that they get exposed you to. Another one that you get is a network that you build while you're there. Right. So there's all these other things. But also in kind of an aggregate, and maybe, I think it's common for people to overindex on the compensation or the kind of current compensation and underindex on other things that. And then there's just the raw emotional value. Do you like being around the people that you're around? Do you enjoy the idea that you're working on? Like is it, you know, those things matter, as it turns out. I have a fun HubSpot story. So when we start on this compensation thing, you know, Brian and I had to pick salaries for ourselves, something more than zero. And so we picked $5,000 a month. Right. It's like, okay, well, it's a number.

And obviously below market value, we'd been out in the market for a while and had worked in our lives. So when we hired employee number three, we had to decide what we were going to pay them $5,000. Hired employee number four, $5,000. And so we just built like, okay, if you're here for the salary, you're here for the wrong reason, right? That's not why you're going to join this Motley crew of folks. And that lasted for like a while. And then it kind of has this inertia built in where it's like, okay, well, all of us sitting in the room chatting with you that we're trying to get you to join the company. are all paying each other, I mean, paying ourselves $5,000 a month.

Now, what do you think you should be able to get when all of us are making $5,000? Of course, that doesn't last forever and you have to get. What was the pitch at that time? So it's not like, you know, no offense to HubSpot, but it's not the sexiest idea. You're not saying we're building the electric car here, you know, like you didn't have that going for you. You know, you might have had like a, you know, your own magnetism, which is like, you know, like for me, I get this cheat code because like this guy, he listens to the podcast.

And this happens, this podcast is a great talent pipeline for us because people will listen to it. And over time, they decide for themselves. Either I think this guy's a dummy and he annoys me or I think this guy's smart. I really like, you know, I'd love to hang out with these guys. I think I could learn a bunch from them. And so it becomes an unfair advantage. But you didn't have that back of the day. So what was your, how did you convince people to do this $5,000, you know, Lego block of salary building?

So we cheated a little bit, right? Because of the first eight people in the company, seven of them, came out of MIT Sloan, the same school that Brian and I went to and we met in class. So it was kind of in network kind of thing. It's like, okay, well, it's just a bunch of friends that sort of know each other in network or whatever. Let's go do this thing, right?

And it's also, and they were kind of far enough along in their careers that they were not missing meals or anything like that, right? They had just gone to business school or relatively good business school. And so that was it. And then the other thing, and this is the... There's equity, but there's also the... Like, this is not that risky, dude. Like, let's say this doesn't...

doesn't work out. We end up being chumps of the idea is really bad three, six months from now. You will basically be able to pick up where you left off, right? There's, like, there's no loss other than the opportunity cost of those three to six months. This is not like a irreversible lifetime decision that I've made this call, and that's all I'm going to have to be able to do for the next five or ten years. And that was enough. It's, yeah. Well, did things change? How many people do you think, um, how many people do you think at a HubSpot have made like eight figures because of their equity? and once you worked with those people for a long time and you're like, oh shit, the company went public

and like, you don't need to work anymore. And does that change the dynamic? It hasn't. So to answer your questions. I always have to, there's this little, it only takes like a second and a half for me to translate eight figures into what is that actually? So that's 10 million plus.

Yeah, like maybe five or 10 million is like the number where you're like, fuck this, I don't need this job. probably somewhere in the 20 to 30 range, if I had to guess, of people that have made that much, you know, over 50, maybe even 100 millionaires in the seven-figured range. But even when that was happening, right, like, well, a couple of things. One is it distorts it a little bit because as a private company, even though the valuation from the last round or whatever is X, the shares are not liquid, right? So they're worth it, but they're worth it on paper. They can't go out and actually sell their shares. So that's kind of thing number one.

And so it doesn't, even if they wanted to, it doesn't, we can't really change. behavior. You can't go off and, you know, buy something with your shares. So that's thing number one. But thing number two is that we did have like this kind of spree decor, right? It wasn't really about the money. It was about winning. It was about kind of building something together. And I like to believe that it wasn't even really the idea that if we had taken that same early group of 2025 people and parachute them into some other company and some other industry, there's still software and SaaS that we would have likely done reasonably well as well.

I think it came down to the people who had good chemistry. They were focused on the right thing. I think we our early hiring policy was to hire kind of smart people that get shit done. That was kind of the thing, right? We want people that have what we call it high wattage. They were like measurably smart. If you had to

have them take an IQ test, we didn't do that. But measurably smart. But there's lots of very, very smart people in the world, but they have this kind of predilection to action. They could not help, but like if they found a problem, they're going to go try and start solve it. They're going to jump in, you know, feed first and they're just going to do it or head first, whatever the phrase is.

And that was enough. So we made a deliberate decision not to hire what we call press release hires. Press release hires when you hire someone and then you feel compelled to issue a press release, say, oh, HubSpot just hired the VP of sales from such and such company, whatever that is a 30-year background in doing X. If we felt like we ever hired someone that was worthy of a press release, we did it wrong, right? That's not the kind of person we were looking for because.

they may have done amazing things at Google, Microsoft, Facebook, pick your company of choice, but the startup is such a different context and you're paying for these kind of specialized set of skills that may or may not be relevant. Arbitrage is really, really hard. So we're bigger on the identified diamonds in the rough,

people that are going to be big, you know it. It's like you're buying a stock early versus going after the folks that already were press release worthy. I think that's been my skill. Sean, you've kind of seen my journey. I think my skill has been, in finding the diamonds in the rough.

So we've had like, well, Sean and I kind of discovered one another. But then like there's Steph Smith who's now at A16Z. We had Trong, who's popular. We've had a bunch of people who went on and founded different companies. And what I've always looked for, like I purposely have looked for these diamond in the ruffs because I was like I can't afford, you know, to pay X, Y, and Z. So I got to hire this 24 year old who I know will be a boss in like five or 10 years. By the way, Sam, it's not just that you can't afford them.

I remember once the hustle got to the point where you could afford them, you were just kind of disgusted by the concept of somebody making that much money. I remember you were just like, how much is this kid over here worth this like engineer at my office? And I'd be like, I don't know, like, whatever. He's 150, 170. You're like, what, 70? Oh my God.

Like, this is, you know, if this person left, would the company fail? No, no, not at all. Well, it was crazy. That was 10 years or that was a few years ago. So things have changed a little bit. But also, like, your people would show up to work at, like, noon. And I'm like, what the hell, man? This guy, like, just waltzed in.

And, like, he arrived right within their serving lunch. But we've, we've, like, discovered some cool people. And I always look for a couple things. The first thing is, actually, this is from Paul Graham. He goes, I look to hire animals, like, people who, like, you're a little bit afraid of and they're, like, just, like, freaks where they work a lot. I also look for people who are, like, weird. So I always want like weird people who have like fairly extreme opinions.

Even if I totally disagree with their opinions, I really like that someone's like well thought, well, well research and has a strong opinion on something. But I love like weirdos and eccentric people. And I have found that if you can at our startup at the hustle, we did a really good job of like accepting weirdos and letting them be odd. And like we like embraced it. And I always found that to be kind of like a, we used to say, you know, let your freak flag. Let your freak flag fly. and we're like, you know, I was like, we'll have, we had all types of different people. We, we had, just every type of, like, person we worked at our company, and they'd like that we, like, embrace their odd, they're kind of like them being different.

Yeah, we have something, so we have, you know, five kind of core values as part of our Hopspot culture. One of them is, is remarkability or being remarkable. And what we mean by that is there's something noteworthy they've done in their past or there's something quirky, something different, something that's an outlier about them. And it doesn't have to be specifically business or whatever even roll that they're in. But there's like, they're just kind of like off the kind of main beat. And that we've done well with those kinds of people. We give them a home, kind of let them do their thing. And it tends to work out.

So Sam had weirdos and kind of like let your free flag fly. You have the, the remarkability. Have you done something remarkable? We had one at Bebo that was the same. We used to say we hired degenerates. It's like intentionally a word that's usually negative. right like we hired degenerate and what we said we would always ask me and furcon we noticed this in each other we were like dude we've gone through these phases in our lives where we just got really obsessed with something that didn't have a clear payoff like it wasn't the popular thing to be obsessed with um like it wasn't the like cookie cutter good thing to be obsessed it like it wasn't like grades in school it would be like you know friccund got really into you know um this video game and he was like yeah became like a top hundred ranked player of this game and like it was a total like you know in one hand I knew it was like a waste of time, but like I couldn't help it.

I just loved it and I obsessed with it. I became the best at it. And I just wanted to win like so badly. And at some point I even stopped being about winning. It was just like I wanted to like get to like the next level and and keep going. And I had done the same thing with poker. He had done it with poker also. So we kind of identified these.

Do you, it's like, hey, do you go through these periods of like three years of deep obsession around some get competitive like thing? And then when you do, do you like really like try to study the game and figure out, how to like, what are the loopholes in the game? What are the rules of the game? You immerse yourself with other players in the game. Because like, well, cool. Our game now is just startups. And we would try to find people who had some evidence of degeneracy.

It's like, yeah, you come in at noon because you stay up till four in the morning, like building that a SoundCloud player that works like TikTok for no reason because you're so in the way that SoundCloud, like, is too slow in the way that they develop things. It's like, other people would look at that as like, oh, you're not really reliable or very structured. Or you, you know, why does you? you work on that? That wasn't even like the task at hand. Whereas we would see that and we'd be like, oh, all we need to do is just point this guy's degeneracy at the right direction and then we'll win. And that was like our mindset. Yeah, I think of that as a kind of borderline pathological

obsession. Like that's like once you attach yourself, whatever it happens to be, right? And what our job is to kind of bring it just shy of pathological where it's like kind of harming themselves, but it's like, you can't help yourself. You're going to like just dig in and whether it's video games or whatever it happens to be, people that have, I don't call it a gene, but they have that trait. tend to work out well in startups because you're trying to attach yourself to a particular thing, a particular problem. The other thing I'm just as aware

since on the topic of talent, I've got this little mini framework, works at multiple levels of abstraction. They're like three kind of vectors of kind of measurement of people. One is you have the creatives, and these are people that start things. They have ideas.

They have 180 mile, you know, ideas, an hour kind of thing if you sit down in a room with them. Then there are the, so they're the starters. Then you have the completers. Those are the people that can make a list It's like, here are the things that need to get done in order for us, to ship a product, to do whatever. And often, those folks are at odds.

Like, the idea folks are kind of really frustrated with the completers that are like, I'm just trying to check a box and make it already. It's like, yes, but I'm doing this thing, and it's not good enough yet. But you have that tension. And that's what brings in the third person, which is the collaborator. And the collaborator is really good at communicating, is really good at bridging gaps across departments, across individual people, and kind of pulling it all together. And usually you're looking for someone that has at least some, like a nine or ten on one of those

dimensions, a seven or eight, another one, and usually very low on the third, right? It's like you can have, what are you? We're creative. I'm on the creative side. I'm like, yeah, for sure. Well, how have you. Well, but how, that doesn't make sense to me because you lead a $20 billion dollar software company that, and you've been doing it for 20 years.

Like, and as a CTO, so like, how on earth do you pull that off? And it's public, it's publicly traded, which means you've got to go through all the bullshit that, like, is the opposite of creativity. Yeah, how do you? How do you? Well, like, one thing he shared last time. You talked about those little like kind of calculators or the little like kind of growth, growth tools that you had built, which was just like, oh, I was just tinkering and

I made this little like page load speed test site and then or whatever. I don't remember the exact example. But you had built like three or four of those that drove like a substantial amount of traffic for HubSpot early on and like even now with wordplay. Like, you know, you're just, you're still creating stuff even now that's like. Yeah, but we were just talking. We were just talking. He's getting ready for the earnings call.

And like, that to me is the opposite of creativity. You know what I mean? That's like you have so many, you have such a narrow lane that you could stay within. That's like, it seems so hard. Yeah. So I'll say this. I have done everything in my, in my power to reduce the time I have to spend on things that I'm not good at, right? Which is things that are kind of non-creative, not a part of that.

So I don't have any direct reports, which is unheard of for a company that, you know, for a founder that has 7,000 people in the company. A lot of them on the kind of product. engineering team, which presumably, you know, CTO would kind of help manage and Lee. I don't do that. And so, and the only meetings I go to are where there's some creativity involved. I don't like to go to kind of status things and updates or whatever. It's like I can read an email as well as the next person.

But there are things that are non-delegatable. One of we should probably talk about it says on my list of things. So one is earnings calls. Another one is getting on to public stages, right? So, for instance, we have an annual conference called inbound that, you know, the last time was in person that had like 25,000 people in the live event, right? Like it's, it's big. And I have to give the keynote every year. And I've been doing it for 10 plus years now, which I hate and I'm bad at. But that was one of those, because I'm founder, that was one of those non-delegatable things.

Right. I couldn't say, oh, well, we're going to have someone else to go do that because in my role as founder, I have a certain kind of weight to me just by virtue of the title of being a founder versus someone else. So, Sean, listen to this, listen to this, listen to this Darmesh story. And Darmesh, you could fill in the blanks as we go because you could decide how much you want to reveal. But there's been a couple different times, maybe three different times. I've introduced Darmesh to a founder of a company who was raising money. And literally within five minutes, he replied and said, I looked at the deck, I'm in for a blank amount. He, don't much you could reveal if you want to say some of the times how much it was. But,

and he replied with, I'm in. Just so you know, though, I've got one rule, which is I always side with the founder, and I'm always on your team. But the downside of that is, like, I'm going to make close to no time. You didn't say it this way, but it's like, I'm going to make close to no time for you. Or like, you know, like, I think you said it,

like, I'm totally going to be silent, a silent partner. I'm not going to bother you, which means if you want to bother me, I probably, you know, I'm not going to talk to you that much. But that's like the stipulations for taking my money. If you want to take it, great, do it? I've seen that happen three different times. And do you want to reveal how much it was or no? I don't recall, but I will say this.

I've made roughly, I think, a little over 100 investments now across my angel investment, I won't call it a career, but my activities. And 80 to 90%, I've never actually talked to the founders or ever met with them. Over a vast majority of my deals, I make the decision within 24 hours. It's like, I don't have time to go dig into due diligence on some industry or whatever. It's like, that's not the point. My point is not that. There's only two reasons I do angel investing.

And neither of them are to make a return. One of them is around living vicariously through other entrepreneurs. I just like that process. And this is, you know, predates even starting HubSpot. And the other one quite immodestly is just bragging rights. It's to be able to say five, ten, 15 years from now. It's like because no one cares like how much you invest in what I was like, oh yeah, I was in Octa back in the day.

I was in Stack Overflow back in the day. I was like, you know, first money on this company, this company, this company. and that feels nice. It's not such a kind of magnanimous giving back to the community as purely it would be cool to be able to have been part of these great founding teams that went off and built great companies.

I really respect that you said that part because I thought you were going to say like, you know, to support the causes I care about. Yeah, I just, you know, just to foster entrepreneurship or like, you know, use the D word, democratize something, something. And instead you said a true thing that I, I think every angel investor feels is like,

it's awesome to have a notch on your belt and be like, yeah, I either I saw that or I backed that, I bet on that and it worked out. It's awesome. It's an awesome feeling. It is a perk of the job and it's a real one. So the fact that you said that to me shows me that you are a real one, Darmesh. I'm what I refer to myself as like a warm-hearted,

red-blooded capitalist, right? So I have compassion. It's not like that I don't like people. I'm not a sociopath, but I'm a capitalist. It's like, okay, well, for instance, and this is going to sound completely and modest, but we opened this door in the last episode, so might as well walk through it now,

is so last episode we talked about kind of putting a value on your time, whatever it happens to be, and that anything that falls below the line in terms of you can outsource a delegate or whatever for less than that, you don't do those things, right? You don't mow your law and whatever. And so I haven't, I should recalibrate, but my number personally, the one I use,

just because the math is easier, like $10,000 an hour. I think that's what I, if I were oddly open market, I think I could make that if that's what I'll, Dude, I would have thought higher. I would have thought higher. Well, what do you think? That was the modest number. It's higher.

No, but I think it would be like 50 or 100,000 an hour maybe. Like, I mean, way higher. One could make the case, but I can make my point without having to make that particular case. Let me ask you a question to make it real. So you buy something, you book a plane ticket. It's like whatever. It didn't work out or you deserve a refund, but you'd have to go chase it down. Do you just have somebody?

who you're like, this is my chief of staff, my EA, that like, I just say, you do it, or you're like, hey, it was $2,000, but it's below my early rate. I'm not going to do it. I just eat the loss and move on. I don't do it. Because even delegating then requires some follow-up, require some explanation, and they're going to apologize because they could only get half back or it was only a credit. I don't care. I just honestly don't care. And so, and back to the investment thing. So let's say, you know, my, when I started, my average investment rate was, we'll call it $100,000, give or take a little bit. It's grown considerably simple. then, but if I spent like five hours doing due diligence or having founder meetings or whatever,

I basically doubled their valuation or halved my investment amount, right? Because not only that I put cash in for which I'm going to get shares, but then I put another $50,000 or $100,000 worth of time in just in the due diligence, which is easy to kind of run up that bill, it makes no mathematical sense why people would do that, right? It's like, okay, do you really feel like you're going to, and the reason they rationalize, and this makes sense, is that if you really believe that as a result of spending that time on the margin, you're going to make better investment decisions. You're going to pick better companies. You're going to do these things.

And maybe for the first hour or two, in an early state startup, there's just not that much diligence to do, right? Like, what are you going to dig into? It's like the idea you don't. You like the founders or you don't. Move on. Our software is the worst. Have you heard of HubSpot?

See, most CRMs are a cobbled together mess. But HubSpot is easy to adopt and actually looks gorgeous. I think I love our new CRM. Our software is the best. HubSpot. grow better. Or the other part that's obvious, but worth saying out loud just in case people are like, well, then why are you doing this podcast?

Well, you also just do things you like. Those are the things that you don't do. You don't put a dollar amount on because you enjoy them. And therefore, it is not a cost to you. It is like a benefit to you. So, yeah, if you love gardening, then you garden. You don't put a $10,000 an hour mark on it. Is that fair for you?

That's how I think about it, at least. That is fair. And so what I solve for is I like to solve for, it's because, It's a little bit of a squishy term, is just raw impact. I like scale. So if you folks were a much smaller blog, let's just say, it's like, oh, I'm going to reach 50 people as a result of this. And I have ideas that I think are worth sharing. And it was smaller.

I'm like, and it's not like, oh, I don't get up out of bed in the morning unless there's at least, you know, 10,000. If this was morning Bruce podcast, then we're not doing it. Amplify my time, right? To what little time I have left on the planet, what things that I know. So I'm always looking for to do things at scale. Like, how can I find a way? Speaking of things at scale, let's talk about this thing. Because, like, on the surface, this thing that you recently did, like a year ago,

is incredibly silly and not worth your time. But basically, I think a year and a half ago, Whirtle is it like a game that, an online game is like a word game that went viral. You built a thing called the wordplay. Is it wordplay.com? It's wordplay.com, right? By the way, you buy domain name. So you bought The Hustle.com for,

us. You bought me copy that.com. Thank you for that. I forgot to say thank you in person. But so you buy like a lot of amazing domains, but you have wordplay.com. And did you tweet that it was getting 7 million users a week or three, what was the number? So the, I just went and checked with the numbers. Okay. So just to kind of place the timeline in frame. So November and December of last year, 2021, is when Wordle took off. In January is when it really kind of hit, it's, I I think close to its peak. And that's roughly when the New York Times acquired Werdle. And a couple things kind of bought, I mean, it was fine.

I think it was a great outcome for Josh Whartle. But there were things that were kind of bothering me that were limitations in the game. And I was an avid player of the game. And now it's like, okay, well, the New York Times has bought it. There's no way that anything's going to happen for like years, if ever. So that was kind of thing number one. Thing number two, like it had been a while since I had launched like some simple free thing publicly. hadn't gone through the process

and there were other things I wanted to learn. It's like, oh, I want to learn more about Versel and NextJS and TypeScript and things like that. So I was like, okay, well, this is a excuse. And then that intersected with the third thing, which was like the dominant variable in the equation, is my son was taking a Python programming class. He's 11, right?

He's going through this process. And for him, it's still very abstract. He's learning programming and enjoys everything involving technology and screens, but it was abstract. So on a Saturday night, I said, okay, well, let me build something. When Python happens to be my language, build something so he can see,

because he plays Wordle, he knows the game. And so I started on Saturday night with a deadline for Sunday, then I'm going to launch something with him tomorrow. We're going to have Google Analytics on it, so we're going to launch it. I'm going to launch it by tweeting it. And so he knows what social media is, right?

He's, you know, so I'm like, oh, we've got this thing that didn't exist yesterday. I wrote the code over the course of last night in Python, the language that you're learning and we're going to launch it and now you can see users coming in, right? You can see that. And so now what I want him to have in his head is that when he has, through the course of his life, as he encounters problems that are solvable with software, which is a lot, like, it's actually tactile for him. It's like, oh, I don't know, I don't have the skills right now to do

what, you know, dad just did, but I know it's possible. I know it's possible because he did it in the span of 24 hours, right? So if I want to go off and build a video game, I want to go off and build some tool for my school. I want to build some social network for my, whatever it is, it feels like now it's more approachable for him. It's got years to go before he'll get to that level. But anyway, so those three things sort of came together. And so we launched it on that Sunday. This is, I think, in February or so, give or take.

And since then, it's had like 45 million games have been played. Nine and a half million people have come through it. Any given moment in time right now, or look at the Google Analytics. It would be 2,000,000 people playing, like, right now. Which... How did it get so much traffic? Where did the traffic come from?

well it helps i have a social media falling right i've got a million followers on lincoln i've got 300 000 on twitter so there's that uh there's some viral that that that's that's a lot but that's not i i wouldn't have thought that yeah yeah it's not enough for that is it how many users do you think out from that um in the early days all was it was it big was it big was it big was it big i know the first day probably a bunch of people checked it out but like i'm sure you posted it and that was the big surge so what was like the first week roughly do you The first week was probably maybe 50 to 100,000, so it wasn't

a lot, but it was something. But then, once you kind of get into it, this is the power of iteration is that, oh, well, one of the things that I found missing in the original wordel was that it was a single player game. Like you played, and you played once a day, and that was it. So two big

changes that we made in wordplay, one was it was unlimited play. You didn't have to play just once a day. And two, it allowed you to challenge your friends. So you could say, oh, I just played this word, I solved it in four turns, here's my score, and send literally a simple link to anyone or a group, and this happens tens of thousands of times, right? Like, someone will take a link that they just play. They're really proud of their score, and then their family. They can post it

their WhatsApp group, they can post it there, you know, wherever they want, and say, I invite you to, like, beat my score kind of thing. And so that's the viral element. And so then as more people play, you can track that as you might have, as a Google Analytics event and say, how many people, how many times are people clicking that share button and issuing challenges to other people? And so that, once you can kind of get into something where there's a compounding effect on the user base, so as a user base grows. And so now the thing I'm fighting, though, right, is that so that's happening, that's going well. But then the interest in Wordle and related games is waiting because everything has its kind of peak in its ebb.

And so it's been an interesting exercise. And so on the kind of learning path, one of the things I hadn't done in a while is like, okay, well, what's traffic actually worth? Let's say I had to make a living on this thing or make the company, quote unquote, or project profitable. So I put Google AdSense on it, which is the easiest thing to do, and discovered that, like, if I weren't bothered by the fact that there would be two ads on the main game board page, if I were solving for monetization, it was like $90,000 a month. Wow. Wow. I thought you were going to say that way less. Yeah, I thought he's going to say

five grand a month, but 90 grand a month and you're, you only have, your only costs are hosting, right? Yeah. And my time. Right. And, yeah. And, First of all, Sean, go to wordplay.com and then go to like the about page. His about page is incredibly well written. It's wonderful copywriting. It's wonderful. You've got a wonderful voice. It says, I'll just read the first sentence, but it says, why would you do this?

Or is it better yet? Why would I do this? That's a really good question. My wife asked me the same question. And then you, like, go on to explain why. It just, you're quite a good writer for also being like this amazing engineer. Typically those things aren't always. I wouldn't have a power writing course that Sean put on.

You know that, right? It's like I'm not. I'm looking around here with my The alumni. I like to say I taught Darmesh everything he knows, even before he met me. I somehow taught him all that good stuff before he built HubSpot.

What do you, so this is making $90 grand a month maybe or about what do you? It could. It's not, right? There's no ad. I turn the ads off because that's sort of not the point. And people were asking me, like, Darmesh, why do you have ads on this thing? I'm like, to learn. Like, it's like I've learned what I needed to learn so I can.

Was, was tweeting and link posting this on LinkedIn, the only way you got users, what do you think this could sell for right now? And is this the biggest side project you've ever created? Our buddy tried to buy it. Suli tried to buy it off you. Did he really? He tweeted out.

He's like, I'd like to buy this off you. I've built mobile games before. He was like semi-serious at least. I don't know. I don't know if you talked to him or not, but. I did not. What do you think you could sell it for? What do you think you could sell it for?

$2 or $3 million maybe? Let's feel right now that, let's say the ad revenue, would go down to like 50,000 or something like that because I haven't turned to Google Adsense in a while. That's $600,000 a year. Apply a 5x multiple. So somewhere between $2 and $10 million would be my guess if that's where I want to be solving for.

And was posting it on LinkedIn and Twitter the only way that you got users or did you do some other weird hacks? I had my blog. It's like I'm a big believer in like what folks call like the flywheel. There's all these little things that are attached to the flywheel, right? It's like, oh, well, LinkedIn helps a little bit, it puts a little energy. Twitter does a little bit, and then I have my blog, and the email goes out,

and there's, like, things that I sort of do. Yeah, so it helps, but it's like the hardest part is that cold start problem. Like, how do you get your first 100,000 people, 100 to 1,000 people? And then it's the matter of, like, tracking the retention rate on those users, do they come back? The other thing that's been interesting about Wordplay, as far as the lesson learned, is that, you know, when it started, the average time a user spent, according to Google, was roughly four minutes on the game. Okay.

In the early weeks. And now that number is at 14 minutes is the average time a user spends, you know, across however many 1,000 of users come in a given day. Right. And is this the biggest side project

you've ever created? Depends on how you measure it. So technically, no, not in terms of just like raw traffic. I've built graders and things like that before that have done better, but... What have you built that? What side project have you built

outside of HubSpot that gets more? traffic than two or three million people a month. I really did side projects. This was my first one that was like clearly because it was a game. Had it been anything other than a game, I would have rationalized some way to bring it into the HubSpot umbrella because I like to have like all my eggs in that basket. But just given the circumstances here, it didn't really make sense. And even now, like I'm thinking about doing a kind of a marketing and sales related

edition of wordplay, right? It's like, oh, the entire list of words. Or do it based on Martec companies. Like, okay, do you know the players in the space kind of thing? And then you can get sponsorships or whatever. Anyway, but, yeah, website greater was this kind of a project where it was like a free, I really like low friction things that people can come to the website.

This is why my son and I were chatting yesterday is where we're looking at Flutter, this new development environment and language, well, dark's the language, but Flutter is the app framework for building mobile apps across iOS and Android and things. It's what the cool new kids are learning. And he's like, no, why would I ever want to build a mobile? mobile app. That's like something people have to download. I have to get approval from, you know, Apple to kind of post my, like, I want to like

just do it like immediately. He's got done. And he's right. It's like, okay, anyway. So that's the wordplay story. It's been, it's been a lot of fun. And it's hard to know with these things like, like where the road leaves. Like, Worldplay itself may or may not kind of connect back to other things, whatever, but the things I've learned through it, I think will. It's like, okay, well, here's what it takes to build this kind of thing. It's like, okay, well, then I'm using it to, uh, play around with community. It's like, okay, can I take the

wordplay user base? What are the things they care about and build a community around wordplay, using one of the existing kind of community platforms and see if that's a thing, right? It's like, okay, if you could aggregate people with like interests,

that in itself has value. And I want to be something that kind of self runs, but we'll see. If you were, I'm going to ask Darmesh, if Sam had built this as a side project and he was at the same point you're at right now, what would you like kind of advise him

to do. If it was Sam's project and you were just kind of an outsider said, oh, that's really cool. You did that. And it sounds like you've kind of reached this point where you don't really have a direction of where it's going to go next. What would you kind of tell Sam? Decide what you want to do, which is, okay, do you want to like take this to the next level and you turn into a $100 million, billion dollar business, you know, spit it off, or decide that it's just going to be a personal project and just like my personal blog is, and I made that decision. It's like I'm not going to try and monetize and hire employees. I'm not going to do any of those things, right? It's going to be, and my son will continue to act as head of product, because he's the one that

test the thing every morning, and we play tournaments every evening. That's the big new feature that's coming out, is a multi-round tournaments. By the way, in terms of like, I think half of what I know, Sean, I learned from you, the other half I learned from FM, right? So one of the things is around chess.com, which you guys talked about, which I've been a member and player on for 10 plus years, I knew of the site. But then you think about wordplay as like, okay, well, this is chess.com, but for word game enthusiasts versus chess enthusiasts. And then like, as a reminder to people,

chess.com is like a huge business. Like multi-billion dollar valuation. We talked about this when we talked about chess also, which was what other things are like chess. And we had said, Sudoku and we had said, I think we had said like a Scrabble or whatever. Word is, word games are all.

I think they're almost as big, if not, I think it would be, I wouldn't be shocked if it was bigger than chess. I wouldn't be shocked. I would be more. shocked if it was like a tenth the size as the chess enthusiast audience, I would guess it's like in the range and there's very few games that are in the range. And so that alone makes it an interesting comp in that sense.

So the lessons you draw from chess.com, right, which is a relatively straightforward, is you have like a rating system, right? You have leaderboards and scores. You have challenges. You have social connections where you make your friends on chess.com. So you can invite, like, it's all the things, right? that these are very easily translatable into other games like wordplay, right? So anyway, so we'll pick and choose as far as you.

Can I give you one little feature I think would be cool? Because leaderboards are always this problem in general where like leaderboards cool for the top 10 people and then for everybody else on Earth. It's like, oh great, I'm player number 39,000. Fantastic, right? And so there's all these like, if I kind of studied this once, I was like, who solved this problem? And there's really three models that work. one is more like chess and games do this they create a rank system so it's not your number 80,000 in the world because that doesn't mean anything, but you go from bronze to silver to gold to platinum

to master to grandmaster and like you you just compete to get your own level up within that to get to your next badge and that's a karate belt the karate belt method let's call it. Then there's the next one which is your social rank matters when it's with people you know that are either your friends, your school, your city, something like that. that so you could kind of hack a proximity-based thing. And then the third one, which I think is somewhat interesting, which is it doesn't even matter what my rank is, but there's something cool. Like, if I go to WordPress Play right now, I feel like I'm alone in this experience.

I don't know that there's 3,000 other people solving this right now. And also, I don't know. I bet you there's like some celebrity that plays WordPlay every day, right? Like, I bet you like, I don't know, Milakunis plays this every day. And I think there's something really cool to like sort of like a stars. They're just like us vibe of like if I kind of knew that that ex-known people, you know, have solved it for today. That's just kind of interesting.

And it's kind of like, you know, makes them more approachable. So I almost wonder if there was like a little feature like that where if you're a blue check type person, you could kind of like off in and be like, I either solved it or failed today. And you could just have that as a little board.

Anyways, those are my three random feature ideas for you. That's a good idea. The one of things, and I don't, it's not surfaced on the, on the, this is a really good idea.

But one of things I do have is in the comment. There's, there's commentary. So as you're playing, the software will kind of give you little kind of sometimes snarpies, sometimes fun messages, sometimes date. It's like, oh, you're one of the few people that's ever guessed this particular word. That's not a very common word to use.

Congrats good for you. Or this is the thousandth time you've used this particular word. You know, points for consistency. So there's this kind of running commentary. But I like that idea of like just kind of front-loading. It's like, here's a number of people that have solved this game. I give you stats at the end of the game. It's like, oh, only 14% of the people or players solve this particular word. And it took them on average seven, I mean, four point seven guesses.

So, yeah. Can I throw two more at you? this is now my future brainstorm for you. There's nothing more, there's nothing more than like an entrepreneur. There's nothing more than like a person who has no stakes saying, hey, have you thought about, have you thought about this? Why haven't you done this yet?

There's nothing less entertaining on a podcast than me telling you features for wordplay, but fuck it. It's just our podcast. If you ever played Candy Crush, they do this thing, which was they make, so stakes, stakes matter a lot in stories or any kind of like adventure.

And so, like, you know, if you open up a pack of warheads and you see a black one, oh, that's the really crazy one. Candy Crush does this in their games where if you start a level, it says this is nightmarishly hard or this is a, you know, medium hard or whatever. So I'd like to see that in the wordplay when I come into every day. I'd like to know if this is a nightmarishly hard puzzle or if this is just okay. It gets me amped up for my play. That's a little good idea. And combining that with your tearing idea and then we can move on. So imagine we had a tiering mechanism that you go from bronze to silver to whatever to ninja.

their level. You know, right now, when you start the game, you get a random word that, and other people get random words as well. And there's a daily word that everybody plays together. But imagine that, like, as you move up the rank, it gets harder. It's like now you're a level that few have achieved, let alone solve, right? It's like no one even gets here. You're here and then, you know, do things for streaks. Like, okay, well, you're the first person to have solved like 50 games in a row at this tier or something like that. I think that'd be fun. So one last one I think you'll like, which is you are a fan of crypto. I think you would, you like the crypto ethos,

and I think if you could advance the cause of crypto, that would be like a win for you personally. So we gave out this milk money grant, this like milk for the milk grow, we gave out like a bunch of money to people just to build whatever they want. And one guy, this guy, Dave, he built this thing that was like a wordal game,

but it was with crypto, which was just you play wordal as is, but if you solve it, you could win like onematic, like a tiny amount or like, then he was like playing with different ideas. He's like, oh, there's actually a hundredmatic jackpot for the day.

And like, only winners are eligible for the jackpot. You might, you might get it or you might not. And so you got a bunch of people connecting a wallet. So I think what you could do is you could actually just add that into Wordplay, which is, by the way, there is a $100 a day prize paid out in Maddo or whatever. All you got to do is create a little wallet here and like you might win. And so I think a bunch of your avid players would create a crypto wallet where they might not

otherwise. So you'll onboard new people into the world of crypto. You can create a dead simple meta, either funnel them to MetaMask or create a dead simple crypto wallet that will become like a play to earn crypto wallet. you know, for the future. Anyways, I will now stop talking about WordPress. Yeah. By the way, I just,

so I actually added the ability to connect your, um, connect your diesel wallet and your Ethereum wallet, um, to Workplay. Um, and my idea at the time was, instead of turning ads off,

I'm going to make that a pot. And so as ad revenue accumulates until the next payout, whatever it happens to be. And then it's like, oh, the top 10 winners are going to get this distribution and let's start over again. So not to make money, but,

we'll have money coming in through ad sense and then we'll kind of, right, a sustainable play to earn. game. That's awesome. Yeah, that would be amazing. So let me, Sean, this is an interesting topic, but I understand there's like laws and SEC stuff around what

you can. I cannot say, Darmesh. Just tell me if you can't. But basically, I think it was in late May, I'm looking at now, like May 25th or something like that. Sean, I don't know if you saw this, but like there was headlines that said like Darmash Shah, CTO, co-founder of HubSpot, buys

HubSpot shares. And I think it was like, was it 10,000, dollars it was it was a pretty substantial amount it was over three forgot the exact amount is but it was millions of dollars and then suddenly like the stock like the next day like went up because it was like oh man darmet like this insider bought it he like he uh like here he has faith in the company that was a pretty that that's a pretty cool move when you're doing something like what is your thinking like are you thinking like um like is it part of you like i just want to prove to the world that i'm brave is it part of you like oh no this is just under

valued, like they're foolish. I mean, like, what's your, what's your motivation there? It's exactly what you said, which is, I just thought the company was undervalued, given the long-term potential. And I've done this before. I did it a couple of years ago in about a bunch of shares, I think even more at that time, like at $125 a share, right? I'm like, okay, well, and this is when HubSpot stock had dipped over the ensuing,

I mean, the prior prior two or three months. I'm like, I understand the market's more like it's, but this doesn't make any sense. Like it, you know, HubSpot stock, to me, was worth more than, at the time, $125. Turns out I was right. And so it's, it's a similar thing. It's like, and it does signal belief in the company, right? But it's what I, it's what I believe. And there are regulations around it. And, you know, people ask, well, why did you, you know, buy at that time? As it turns out, it was the exact window of time that had to wait a certain period since my last transaction to when I could buy in the day that I was eligible to buy, I bought. And it's like,

oh, the price is low enough. I still have conviction that, um, law. Are you also buying with money that, like, where does this $3 million come from, let's say? Isn't that just stock you previously sold that you now are buying? Or it's not like you have some other huge side income stream? Yes, yes, yes, yes, yes. Or can you, can you take a loan against your HubSpot shares to buy more? There's like a hundred things you cannot do. That's one of them.

Wow. No, I think I saw that the other day. And you've done, you've made a few decisions like every once in all, you do something. and I'm like, oh, this guy is nutty in a cool way. And that's not exactly nutty, but it's like a pretty bold move. I thought it was a pretty cool move. And I saw that. And I was wondering what was going through your head when you did that?

What's the psychology like when, I don't know, Hubsby's stocks like, I'm just rounding. I think it's down like 40, maybe 50%, something like that from the all time high, like during the last kind of the peak of the peak last year or whatever. And so, you know, we come on here sometimes. and I'll be like, all right, guys, you know, you know, Sam will be like, dude, how are you? And you lost a bunch of money today. I'm like, yeah, yeah, I lost like a million dollars today. And like, you know, Heath is down and I'm down a million dollars. I'll share my psychology of like dealing with this, this travesty of a loss or whatever.

And I'll be like, yeah, you know, here's how I think about it. You play that game at like a thousand X higher stakes where like, you know, more like you lost 500 million. Yeah, exactly. I'm losing 500,000. and you're losing $500 million or whatever. You know, something crazy like that. What's your psychology like, I don't know, like, I think you know what question I'm trying to ask,

even though I don't have the word. How does it feel to lose half a billion dollars is what you're asking me? Yeah, and how do you deal with that? And like, yeah, go, go for it. Is that how much you lost, do you think? It's more than that, but yeah. Who's counting? He's like, this podcast is more fun when we were talking about wordplay.

Actually, fine. Like, I'm not really in the, I'm not just saying this, but it's true. It does not phase me like one bit because the reality is it does not change my life, one iota, right? Other than like, okay, well, it impacts, you know, Hopspot employees and Charlott. I get that, but in terms of me individually, like nothing changes, right? Like, I wasn't planning to buy small islands or takeover governments or something like that.

Or by Twitter, right? I didn't have any of those kinds of plans. And so absent those kinds of plans, Like, I feel sorry for the nonprofits that I would have invested in. But, you know, my wife continues to invest. There's, you know, we have plays to do the philanthropy we want to do. And so it's like, okay, well, I still wake up every day than do the same things I did before. And I'll look at the wordplay things and respond to user emails.

Or it's like, and do my HubSpot stuff. It's like, okay. Like, what's really changed? So you don't even have, you don't even have the self-talk in your head where you kind of need to like, because for me, when it happens, I'm like, you know, I have an instant reaction as I go look at a chart. or a price or whatever. And then I give myself a little self-talk and I'm good. Like it lasts 17 seconds, but I do have those 17 seconds. It sounds like you don't even have those 17 seconds because you're like, well,

I've already been over this before in my head at some point in my life and I just decided it doesn't matter. Let alone the self-talk. The self-talk is one thing, let alone like that. And then there's also this other thing that you and I have, Sean, which is like if the markets are shit for a year or two, like we will change our day-to-day actions. Like, you know, we may not buy X, Y, and Z or like we might, you know, we're not. we're not to that point where it's like, it doesn't matter. Major cutbacks at the Puri household right now.

Major cutbacks. Yeah, it's like, we'll maybe change behavior, but you don't even change. I laid off my son. They change in the other direction, right? So as the market has dipped, my kind of average check size has actually gone up. I've made bigger bets and things because I think valuations are starting to adjust, slowly.

So I think there are better deals now, good entrepreneurs, starting companies. So, but over. all, like the psychology of it just just does not, like, have any impact. And like, over the long term, you know, I didn't make this up, but I, is, is that the, you know, the valuation of a company, which is like the market price will oscillate around the value, right? And value is, like, the revenues you have, the products that you build, what are you actually doing for your customers? And so that, you know, if our revenues had dropped off, you know, before something like that had happened, that would be a different story. But it's like, okay, well, that hasn't changed.

We are the same business today, if not better than we were three months ago, six months ago. And the valuation over time will kind of self-correct some of the things I like about the market is that I think things will kind of wash out and we'll see. And a lot of HubSpot's customers are kind of like, you know, medium-sized, let's say businesses. So do you like, do you spend much energy being like, okay, where is the economy going? What's going to happen to my customers, which will have some knock on effect of like what's going to happen to our business? is do you care or spend energy there? Because I find myself, for the reason I ask,

because I find myself sometimes going down these rabbit holes of like, okay, what do I think is going to happen? Then part of me is like, well, does any of that really matter or affect me? Or is this energy useful or is this just sort of nervous energy that I'm wasting thinking about this stuff? Do you do that? Is Hubstads customer base? How many customers does Husband have like 130,000?

Like, yeah. Yeah, and I think when I sold it was 100,000 or just crossed 100,000. In the grand scheme of things, one of the reasons I saw them, like, well, 100,000 customers, that's like kind of a lot, but that's not that much. I was like, the market's way bigger than 100,000 people who would want to buy this. And so is, is the 100,000 or 150,000, whatever it is. Does that number even big enough to have the needle move significantly when the economy is shit? On a percentage basis, look, it's, I'll answer it this way. So I'll answer the first question, then we'll kind of move the second one, which is, you know, do I spend time thinking about this?

do I do anything about it? The answer is yes. At HubSpot, we will try to model out. Here's the impact we think it could have on our business. And there's two sides to it. There's the kind of defensive side of it. It's like we want to make sure that we have enough cash in the bank to weather the storm. We don't know how long the storm's going to last.

And we have models for how long it's going to last, how deep it's going to be those kinds of things as far as impact. But then the other part, which is, to me, much more exciting, which is, okay, given what we know, what can we do to capitalize on this crisis, right? this is what's happening right now. What can we do to make this net positive for HubSpot? And we had something similar happen in 2008 at the last HubSpot was much earlier. So things, even when the pandemic started, one of the things we did is like, oh, there's lots of uncertainty, businesses are struggling.

Everyone's kind of batting down the hatches. And so we said, okay, we're going to give even more value. We're going to, for our partners, we're going to front them the cash for the revenue we know is coming over time because cash is an issue. And we had a bunch of cash in the balance. So we did things that kind of made us stronger, help our money. our customers. And so we're looking for those same kinds of opportunities. I was like, okay, now that everyone's kind of looking at the P&L and looking at all their line

items or whatever, can we benefit from this? Because HubSpot in some ways is counter cyclical. It's like, okay, well, instead of buying the big incumbent and spending hundreds of thousands of dollars, maybe now people that might not have considered HubSpot a year ago would now consider it because there would be more value conscious now than they were historically. When you were starting the company, so like there's a, you know, if you just look at the math, there's a world where HubSpot in the next five or 10 or who knows how long can be worth like $100 billion, which is, you know, one of the biggest top 200 or something companies in the world. When you were starting the company, did you have a number in your head where you're

like, man, I think this, I think this can make $100 million here. I think this might be a billion dollar company or was it as big as, man, I think this could be worth tens of billions. We didn't have a specific number in our head, but we had, um, I'll say, make comparables for lack of a better term, which is, okay, there are successful software companies that have done similar or related things, either they're in the same market or in the same target customer base that had achieved it. It's like, okay, well, and this is what we told to VCs at our pitch. We're like, okay, we're not, we think at the time we were just in marketing software, so here we're, I'll give you the first 30 seconds of the pitch, is that in the history of

software, no one has ever really built a 10-plus billion dollar household name, global brand marketing software company had never been done. Omnish. was the greatest one at the time with a billion a half dollar, you know, price tag at the time. And we're like, and the reason people, you know, companies have not been built in the marketing tech space is because marketing is an arts and crafty kind of discipline. It's about the shade of your logo and you're outsourcing a bunch of creative stuff or whatever, but it's not the kind of problem software solves. And our belief was that marketing was increasingly turning into the kind of thing software

does solve, lots of data coming in. You're trying to make decisions around all this stuff. It's to look exactly like an industry that software can help with. And so our thesis was that someday someone will build $100, $500, $500,000, $500 software company that's doing the thing we're trying to do. And we said it might as well be us. We're relatively nice people and we're kind of committed to this

and seeing it through. So do we think the odds were relatively high that we would pull it off? No, but did we think there was an opportunity to do the kind of thing that you're talking about? Yeah, others had done it. We were not putting someone on Mars, right? That was like, okay, well, people have done this before

and this is just a different time. And maybe now the time is right for a new company to do something that has been done but better. This goes a little bit to your Pixar kind of vision. Sean, it's like, okay, well, you know, people sometimes give us like, okay, well, you know, what are you going to do that's different? And why is this, you know, what is the world need more? The answer is the world does need more Pixar's. And so, you know, saying to you, like, oh, you don't really need to do that.

It's like telling Elon Musk, does the world really need another car company? And like they kind of downplay the fact that's like, yeah, it's got four wheels. And I guess you from point into point B, but it's all, like there's just one, interesting element about it makes it completely different right it's like it's the same thing like most ideas that have been super successful are not complete new from all cloth cut right they're like and i don't like the cliche of building on the shoulders of giants but it's like like just about everything that's ever been done is derivative to some degree it's just based on your level of abstraction how many steps back you're willing to go so it's like okay yeah i can see someone building something

massive here it's like i'll get off my ranch it's like so we had facebook did awesomely well. Then Twitter comes along and people said, oh, well, that's just Facebook where you have shorter messages or something like that. It's like Facebook with constraints. With less.

And then Facebook comes along. It's like, well, you can post photos on Facebook. Why would anyone ever use Instagram? That's like Facebook with all the other cool things that I like as well, right? No Messenger, none of that stuff. And then TikTok comes along. It's like, well, that's just kind of videos

that you can do on Facebook. You can do on Instagram. You can do on Twitter. But it's this. It's like just different enough in a compelling enough way where, and it's still a video, social net social based video app

and lit the world on fire right so even something as old as video or as photos it's still not over it's just not over it's just part of the kind of the human condition right now anyway it's uh if i was i'm with you uh sean if you go off and want to do

another Pixar and if you're ever looking for an investor that will make a decision 24 hours i your god what was that tweet about sean that was on the left field what do what are you saying uh okay so all my tweets are out of left field that's just Twitter. That's what Twitter's supposed to be, right?

Just a bunch of left field shit that all gets put in a feed. I was watching. I don't know what I was watching. My nieces were over and they were watching Toy Story. And I was like, Toy Story is amazing. Pixar's amazing. And I was like, why is it like, I want to do something amazing. This is literally how my brain works.

It's like, oh, that looks so awesome. That's like an awesome end of output. I would be so proud if I had made something like that. I bet I could, right? Like it's this combination of like seeing something that is really appealing and then having the delusional belief that like of course i could do it if i just tried and so i just thought it to myself i was like you know that would be a fun company to build if you could just make great stories great movies um and put them out there into the world that

would be so fun as a thing if that's like the thing you did and like i mean hundreds of millions of people not just like use your product there's one thing to use your product it's another thing to like love it grow up on it and have like you know like this extreme like nostalgic emotion around around like these movies, right? Like if I see, you know, for everybody, it's a little bit different, but for me, it's like, I don't know, Home Alone and Mighty Ducks

and then, you know, Lion King. There's like a couple of movies that just like, they meant a lot at the time, and they still mean a lot, even though I don't interact with them. So I have, otherwise I'm going to forget.

There's one thing I need to say on this particular episode because otherwise it'll keep me up at night. So I have like a handful of like frameworks and things I think about the way to think about the world. And this ties back to Sean's next trillion dollar company thing, Pixar, which I think it can be, by the way, Sean, just so you know.

Okay, so imagine, let's take a step back. I'm on a whiteboard. And the whiteboard, it's the universe of all possible people, everyone on the planet, and he draws a circle with one of your skills. So in Sean's case, let's say we put copywriting as one of the skills that he's in the top 1% or top 5%, whatever number you want to associate with it. And so that's the circle. It's like, okay, X number of people are at Sean's level or better at copywriting.

Awesome. Let's say we draw another circle that's, we'll call it crypto, knowledge is just how crypto works. And that's a group of people. Awesome. Rarer skill, because it's newer. There's fewer people that know how to do that versus copywriting. We can accept that.

It'll be a smaller circle. What happens, though, is if you intersect those two circles and turn into a Venn diagram, the number of people that know copyrighting really well and also know crypto really well is a hundred times smaller than either of those circles combined, right? And we see the same effect in standardized tests. If you took the SAT or the GRE or the G-MAT, there are people that are really good good at English portion of the test. There are people that are really good, the math portion of the test, but the ones that score

really, really well are the ones that are good at both. They don't have to be the best at both because that's the thing that's actually rare, is the combination of the English and the quant. Same thing here. So now imagine, so this is what I call it the trillion-dollar Venn diagram of success, right? I just made that up. So you draw those circles of your skills and say, okay, well, I am now not like one in a million. I'm one in a billion, right?

or one in five billion, whatever that is. And if you can convert that into some kind of monetizable business thing or whatever, that's when magic sort of happens. So that's kind of thing number one is like, what's your thing? What are your skills? And what drives them value? How much value will that intersection create? It's two things.

One is how rare is that intersection, whether it's two circles or three circles or whatever. How rare is it? And then the other one is how much does it kind of reinforce, force the other skills that you already have. So, for instance, I'm a software developer. That's my core skill. I've been programming for like 30 years now. That's my thing. Deep down inside my core. If I

combine that with, I'm going to go often, which I could never do, become an Olympic level swimmer, let's say. Also very rare. The intersection of that, it's like, okay, well, the opportunity that reveals because the two things are so unrelated, I don't know how I would take my ability to build a web app and intersect it with my,

like, yeah, there's some things I could do, but I don't know if that would be that huge. But, software development is applicable to lots of if I was going to be an academic researcher, if I was going to go into music, if I was like other things, there's a lot more overlap to agree that those two, they reinforce each other. The software helps me do this, and that helps me

do this. And this is one of the reasons, so my advice here was, as you're picking skills to acquire, acquire skills that are both rare, but also reinforce things that you're already exceptional at, that will kind of drive that rarity, and that's what drives the overall value, which

kind of brings me to, is like, And so when I think of things that I want to learn, it's like, okay, well, this is why I got into copy. It's like if I can, and copywriting is another form of, this is communicating at scale is what copywriting is, right? Like it's in usually textual form. It's like, okay, well, I don't know that many software engineers that can copyright really well. Like, literally, other than that have not started companies, right? It's like they don't exist.

But very rarely do you get like really, really good engineers that went off and read six books on copywriting and took Sean's class. That's not a common approach. You weren't a good writing, a writer before you got into this? No. I mean, your writing is great. And by the way, Sean, you got to pimp it out. Maven.com slash power writing or just go to maven.com and you see it.

Yeah, yeah. Just go maven.com, M-A-V-E-N.com. I'm on the homepage. It starts in two weeks. All right. So what you said is great. I would add one more circles to that. To your picture thing, by the way.

The reason you might pull it off is because you have a very weird and unique and related level of skills. So yes, there are people that are better, maybe better creatives, better animators, better entertain, whatever, but they don't know crypto. Maybe that's the thing that unlocks the next trillion dollar company is entertainment intersected with crypto. It's the Netflix for the blockchain, whatever it is, right? Something like that, where two things combined that never had been put together in that way before.

The other circle that I would add that I think people underestimate it. So I tweeted this out. So people, I didn't explain what the tweet is. The tweet was, as I said, the next company I build is going to be like a new age Pixar, like, like the next Pixar. And I think I would work on that project for 30 plus, like 30 plus years. I'd just keep going with that company. I wouldn't be trying to sell it or flip it or get out of it or whatever.

So that was the tweet. And then a bunch of me, I basically had two reactions. One reaction was awesome. Like where can I sign up? How do I work for this company? That sounds awesome. I love Pixar. You could do it.

And those are like fans of MFM type of thing. Or people who themselves had been thinking, God, that would be awesome to create another like Pixar type of company. you know, because I love Pixar. Then there's the other half of people that were like, what makes you think you could do this? You know, like, you know how hard it is to make a movie? You know how expensive it is?

You know, how unique, you know, Steve Jobs and, you know, whatever, Lasseter and Catmull, like how rare those talents were when they came together. That's a once in a generation company. And then other people were like, one guy had this amazing burn. He was like, check, aqua hire, like a green check mark. aqua-hired power writing course podcast next Pixar and I was like

oh thanks that's pretty solid actually and so you know a bunch of people were sort of all in the same bucket of like this is so hard this won't work you can't do it there's some version of that and so the third circle one is like I'm really great at X I'm really great at Y the third is just I have the courage to go do a thing

and like Tim Ferriss once told this story he goes I went to a business school class Harvard Business School class. I gave this talk. At the end of the talk, I go, oh, by the way, guys, I'm doing this challenge. Only for you guys, you know, whatever.

I want to get in touch with either Bill Clinton, Jennifer Lopez, or, you know, some sports person, you know, Michael Jordan or whatever. If anybody here can connect me over email with them, like, you know,

just reach out to them. And if you get a hold of them, connect me over email, I will buy you two round the world playing tickets, you know, for, you could fly business class for a year. around the world anywhere on my dime. All right, guys, thank you very much.

And he told that to one class. And he's like, you know, you have 30 days to complete this challenge. And then I think I forgot what it was. It was like he did it to two classes, but he gave a slightly different message in each. The first one, he just said that. 30 days go by. Nobody did it. Sorry, nobody completely the challenge.

He's like, oh, what happened? Turns out nobody even tried the challenge. The perceived difficulty was so high that nobody did it. So in the next one, he told that story. And I think he added a twist, which was whoever gets the closest to it wins. And all of a sudden, like, everybody tries. And in fact, I think somebody did get in touch and actually successfully completed the challenge. And he was like, he had this principle, which was sort of like, you know, everybody wants to fish where everybody else is fishing because they think it's so easy to catch fish there.

He's like, in actuality, often it's easy to just go catch a fish where the fish actually are. And you don't have to base it on how many people. how many other people you think have tried something or what the perceived difficulty is. And in fact, sometimes the bigger you go, the easier something can be because nobody else is even trying to do it. And so I would say like, you know,

this Pixar thing, who knows if I'm going to go do this or something else? I tweet things just almost to my prototype. It's like, let me say this out loud. Let me see how that feels. If I sleep and to wake up tomorrow, do I want to tweet five more ideas about that? Or am I over it?

It was just a passing fleeting moment. But the core ingredient I think most people lack his courage to actually go and do the thing. And I think that's the, the, people put way more emphasis on what skill am I top 1% and they kind of, they undercredit themselves. One skill you could just have for free.

You just got to go, it's like at the sand, the deli at the grocery store, go pull the number. Is, yeah, I have the courage to actually go do it. Like, you know, I'm, I will go do, pull the trigger on this thing and not wait for other people to kind of like reinforce that it's a good idea to me. Yeah. And this is, I could not agree more. And I think people conflate sometimes skill versus talent,

and they believe they don't have a talent for entrepreneurship or for design, for programming whatever it is. In my mind, so skill is something that's learnable. That's an easy definition. Talent is the rate at which you could acquire a particular skill. So if you have a talent for music, that means you will acquire musical skills faster than someone that doesn't have a talent for music.

It doesn't mean that someone that doesn't have a talent for music can't learn it. So they may have a ceiling as far as how far they can go. Fine, I get that. But this doesn't mean they can't do it. And so one of the big lessons kind of in my life, in my professional career is that most things are actually skills, not talent. Mostly, like, it's like you can start with zero. Like, I would have been voted least likely to ever start a company in my entire generations of family.

That's not a talent I ever had, like, until I went off and did it. It's like, public speaking was not something. It's like, oh, that's a skill. And then there's this thing from software engineering, I think it's worth sharing. I think some of the best ideas are when you take stuff from other industries and pull them into this thing and apply it here in a weird way. But in software engineering, there's this thing called functional decomposition, which is take a problem, be able to articulate well. So a function that has a set of inputs and an output in what it's supposed to do. And really all software problems are being able to take the highest order function is, let's say you want to create a possible investment based only on the website.

It's like, I'm going to give you a domain and you're going to give me a score from zero to hundred as to how good this is. Okay, well, that function is easy to define. Like, domain goes in, score from 0 to 100 comes out. What other functions does that function need in order to pull that off? It's like, okay, I want a function that looks at the domain and looks at the level of SEO they have. That's one layer down. The person that's right in the SEO function goes down levels. Like, I'm going to look at the on-page SEO and see how good they're doing at meta-tag and H-1 titles,

and I'm going to look at the off-page SEO and their link acquisition and that kind of stuff. So if you roll it all down and you go down far enough, individual functions at the atomic level are so simple as to be trivial. What matters is the fact that you were able to abstract it down that simple thing, right? And so most things can be broken down that way. So if you look at, oh, I want to become someone that can give a talk in front of 25,000 people on a stage, that seems like an insurmountable task for someone like me that's never done that. And that's not my, that might not my thing. It's like, oh, well, what does that involve? Number one, you have to have kind of overcome. I didn't have like stage fright. I had severe

stage anxiety, right? Stage fright is like, oh, there's a ship, It's going to come down from space and just suck you up because you were so bad. And stage anxiety is like, man, I wish a spaceship would come down and suck me off this stage right now. I want to get off. So there's that. Like, don't you know, don't pass out on stage. And then there's the, oh, you learn about storytelling. You learn about writing.

You learn about slide design. You learn about humor. And I did all those things, right? Read books, took classes on all those components of public speaking. In aggregate, I'm okay now, right? Like, I can do that. And again, then it's practice. and you do it over time.

So anyway, my point here is startups, whatever skill and startups are a skill, figure out what set of skills you need to acquire. Some you'll be good at acquiring because you have the talent. The other one, you're just going to have to grind it out more than others made, but it's doable. It's a doable thing. One question that I had.

If I can do it, anyone can do it. That's my point. I love that. So Sean, I love that. Sean kind of added this thing to your event diagram of like just people brave enough to get started. And would you add another thing?

like with the hustle, we sold in year four or five. And I don't regret it. I'm very happy with that. But I actually like, I looked at the numbers this year and I was like, oh, wow, we would have made like maybe like it's, it was close to the point where like you could have potentially next year made more revenue that year than all the revenues combined. And I'm like, whoa, that's kind of crazy. Like I, again, I'm happy with it. But like real value. Like I guess for me, I was like real value was created in year like five, six, seven, eight. Of course, you probably could say, like, when you're in your 5, 6, 7, 7, 8, you're like, oh, wow, it's really created in 10, 11, 12. But do you think that what portion of HubSpot and your success has been, well, I'm just willing to shut up and focus on this for 20 years as opposed to you actually being amazing or good at product and marketing and things like that? Yeah, here's how I think about it.

I think the outcome is a combination of, like, dreaming really big and, like, iterating really small and having tight feedback loop. So the dream really big is you have to have something that can someday translate and it doesn't have to be as clear of a vision as, you know, Sean has kind of laid out as far as oh, it's going to be Pixar for the new generation. But you have to kind of start

with something relatively big in mind, at least at some level. But then it really comes down to the iteration, right? I think others have demonstrated this through data is that the quality of the output is almost, I won't say always, but frequently a function of the number of iterations, not the quality of the people's. For instance,

So one of the common examples that's thrown out is, and I've heard it with a pottery class or a photography class, but it's like, oh, one set of students divide it class in half, let's say it's a photography class. One set of students is like, okay, every day you have to submit a photo for the next 30 days while this class is running. The other one is like at the end of the 30 days, you're going to submit your best photo,

and then your grade is going to be based on the quality of that best photo. The first class is like as long as you submit a photo every day, you're going to get an A at the end of the 30 days. The other one is like as long as your, is A quality material, that photo is going to win. And what's been proven out across disciplines is that the class that did the multiple iterations had a better output than the one that was trying to solve for quality.

Like arguably the first one's like, all they really had to do was submit a photo. It didn't have to be like world class quality. It's not the best I could do. But just by virtue of doing it, they're going to make it better and make it better. At the end of the 30 days, they produced a better photo and they produced a better clay pot if it was a pottery class

than the other one that was solving for quality. And they were like too much in their heads trying to say, oh, I'm going to do the best I can do. Like, no, just do it. repeatedly. But the key to that, it has to be meaningful iteration. If you're just iterating and doing the same thing, you're not learning anything, there's no feedback loop, then the iterations have no value. But if you have a tight feedback loop, like, I'm going to do this thing and I immediately get response back that tells me whether I got better or got worse, that is amazingly

powerful to be able to do that and compound it over time. So I think my, I'm not that special, candidly. It's like I'm willing to grind it out more than people that are smarter, and I'm a little bit smart than people that are willing to grind it out. That's my Vendai. That's awesome. Have you, you've probably seen this or maybe you guys have done this, but there's this group of like consultants that created this thing called the marshmallow challenge, which they go to a company and they give you like a bunch of sticks, one marshmallow, some tape and like a string or something like that. Have you seen this, Darmesh? I think I have, yeah. But I'll kind of summarize for this. Yeah, those you have it. Basically, they give, they give you these, these.

set of tools and they say, okay, your goal, the game is you need to get a marshmallow. The winning team is going to have a marshmallow like as high above this table as you can. So build your tower as high as you can. If you can, whoever gets the highest marshmallow, whoever's tower has the highest marshmallow at the end wins. We're going to stop the clock after 30 minutes. We're going to say hands up and, you know, your marshmallow, whoever's marshmallow is standing the highest wins. Okay, good, good.

So they go and they do this test with like a bunch of different types of people. They do it with consultants. They do it with like kind of doctors. and they do it with, you know, engineers, they do it with whoever creatives, like ad agency types. And they're trying to see, okay, which group is going to perform the best at a challenge like this? And basically across the board, what they found is that they suspected maybe engineers are going to do the best. And the engineers do on average do a little bit better than others, but not by much. They actually are all pretty horrible at it.

And I think like, you know, whatever, 80, 90% of the groups at the end of the challenge, their marshmallow is on the ground. It is fallen over. It never even, you know, got up. up at all. Like if you had just put it, if you had just taken like, you know, two sticks and put a one marshmallow on top, you would have won the challenge. And the reason why is, and they did this test with kids. And kids actually are phenomenal at this. Kids on average will beat the adults at this game. And why is that? Well, because what happened is that they would give the project to the adults and the adults would spend the first five minutes like delegating roles. Like, okay, you're going to be

the person who does the planning. You're going to be the one who you work on the sticks and the bottom structure. We're going to do this over here. Then they would just like kind of draw. out like, okay, let's do a tpee. No, let's do a ladder. Let's do this a cube shape or whatever. And they would do all this. And at the very end, they would try to stick the marshmallow on. And what they don't realize is a lot heavier than it looks.

And it will outweigh the sticks and it will all fall over. And because they're doing that thing where they wait until the very end to like ship the final good product, they don't even realize where the flaw in their plan until like it's too late, essentially. Whereas what kids will do is kids will immediately grab the thing. They'll stick the marshmallow on. And it's like, if the kids don't eat the marshmallow, the marshmallow will get into the structure very quickly and they'll see, oh, it falls over.

Okay, it falls over. That means we need to iterate and we need to do things differently than we would have otherwise assumed. And that, like, one lesson I've done at pretty much every company I've ever started because it's the only way I can get engineers and designers who by nature are often like sort of like perfectionist or quality. And like they in their associate, they in their mind associate the longer we work at this, the better the quality will be before we ship it. And I'm always like, dude, let's ship it today. Let's see how bad it sucks.

And then let's remove some suck from it. And like tomorrow it'll suck a little less. And then tomorrow it'll suck a little less again. And the best way I've been able to drive this point home is to give them the marshmallow challenge and not just like watch the video, watch the TED Talk. It's like, no, go fail at this so that you taste defeat and then you will actually learn this lesson. That's like the greatest CEO thing that you've ever done. That's a good one.

That's a really good one is to make people do this and then make them watch the TED Talk. That's like, that's a really good leadership. tactic. I'm 100% going to steal that one day. Yeah, it's an awesome one. All right, we went kind of long. I don't know if we were good to keep going or not, but Ben's telling me wrap up.

But, Darmesh, this is awesome, man. I love having you around. Are you, the last time you were on was like a year ago, I think. And I've been like, I've been like begging you. I'm like, man, just come on. And he goes, I'll just come on today. And I'm like, all right, cool. are you a

actually I have a quick question what you know people ask me about selling to HubSpot and they're like has it been good from a creative perspective

it's been awesome you guys haven't like we haven't been told a thing on like what we can and cannot do of course I don't think we do anything

where anyone would ever tell us you can't do that but uh maybe Darmesh do you ever get complaints

about anything we say that's what I was gonna ask that's not I'm gonna ask is there anything that like so far

I guess there's nothing that's crossed the line because we've not heard a thing. But it's been crazy how productive this relationship has been. I did not think that because, you know, people say one thing and the reality is different, but it's not been that way. That's been pretty cool. Yeah. Thank you. I'm glad that it's working out in your teams.

You folks have been kind of great for HubSpot. And I know this keeps you up at night in terms of evaluation. I've thought about that a lot. probably not as much as you have, but at the time, I would not beat yourself up over it. I think it was a fair deal. I don't know that.

And even at that, just so you know, even at that price, and nothing to do with you, but like it was a board level discussion. We had to, like, okay, do we really want to, you know, not that it wasn't worth that, but was it worth that to us at the time because it was a relatively new thing that we were doing. I think there's a, but, yeah, for sure.

I think there's a world, I think there's a world where in one to three, three years, the podcast alone is worth more than the deal. Yes, I definitely see that. Yes. But the same way to kind of, when we can kind of wrap on this, is that when we were talking early in the beginning of the episode around kind of compensation as being just one of the dimensions of value in a acquisition, the kind of the valuation that you get the price tag is just one dimension of value.

Then the rest of it is, how happy are you? How happy is a team? Did you meet people that will kind of, you will enjoy working with in your future years? Are there your future co-founders? It's that kind of thing. It's like we know that this is not forever. We know that going in with, even with people we hire,

but especially with M&A. But yeah, hopefully an aggregate, you know, HubSpot delivers a bunch of value. That's my pitch for why it's okay to join HubSpot if you're ever out there looking. No, it was awesome. Well, thank you.

This is awesome. Found what do you think. Yeah, great episode. And I'm glad you used our line against us. I, he emailed us up then. I was like, oh, you should come back on sometime, which is like the, sometime is like one of the most dangerous words

in the English language. Yeah, because it's like you think it's soon and in reality it's never. And you pulled a great move, which was what we talk about, which is like, forget scheduling stuff. Like, either I want to do it. And if I, if I can do it right now, let's do it right now. And if not, like, let's not schedule it for the future just because we didn't want to do it right now. And you were like, how about today? And we were like, all right, let's do it.

Let's do it. Perfect. And I intentionally made it open. It's like, okay, I knew when my last meeting was. It's like anytime after this. So it's not even like, oh, like I could have made it work this afternoon, but I was only available for the small window. It's like, no, any time between 2 p.m. and midnight, if you had come back,

I would have been, let's do it. It's, yeah. That's awesome. This is awesome. Well, it's a lot of fun. Thanks for doing this. It's a lot of fun. It's a lot of fun.

Thank you for coming on. All right. Thanks for having me. Yeah.