#153 - Selling The Hustle for Millions: How The Hustle & Hubspot Deal Happened

yeah i feel like i could rule to world i know i could be what i want to put at all in it like a day's off on a travel never look kim bag okay we are live i'm back sam is here and sam who's who's this other gentleman we got alright so we have karen here karen flanagan who is gonna be speaking from hubspot perspective he's your what he is my new boss nice how many years has it been since you had a boss a long time a long very long time people said to me i can't imagine you having a boss and you know what like i'm excited because i i'm ready to learn new stuff i'm ready not to focus on the stuff i didn't wanna focus on i'm excited to learn so i'm pumped karen i hope you're pumped so what is someone worry most about about having a boss when you haven't had a boss what are the nightmares i don't think i even know like good hygiene of like having a boss like good hygiene of working at a company like i'm still gonna learn that i don't know like everything i feel like i'm i feel like i'm a kid who like was at a orphanage and now has like a real mom and dad and i'm like wait how do you how do you do this right right we celebrate thanksgiving like or like a while dog who now has an owner i'm like what is this what do you do now right right i'm not cold all the time i'm inside yeah i i actually also so i currently have a boss guy doug and doug is great he's a great guy and like super super nice smart guy but the other day he was like hey like can you like send me like like an update every week on what you're up to and i was like oh yeah that's what i always asked people who kinda report to me i just had reported anyone so long that i was used to only writing like a like an investor update every every month or every quarter and this guy probably like how come this guy doesn't talk to me like at all and now i was like oh yeah shit by bad i got you so we had the deals done i got that approved by the way i can say that karen we announced it last week it was announced last week it's kinda just now set in i haven't talked to you sean so i wanted to talk to you about it and we actually i wanted karen to come on because we could have his perspective because i think this was him and the cmo of hubspot i think there was their original idea to acquire a media company and i think most people understand it but it was very very very weird when i first told people and i thought it'd would be cool to have his perspective because i think this is gonna happen a ton and like me and karen and and the rest of the folks at husband we were like you know i don't care about awards i i don't know if they do or not but i don't care about being like doing something to win an award or to like have a case study written about us but i do think it is kinda cool that like we're gonna do it's gonna have a ton of cool stuff and maybe one of the byproducts is like this is actually like the first of many and it could be like the road map so i we could talk about that so there's a few of these right is i saw this in the trends group and then i stole it and tweeted it but basically like you robinhood bought snacks which was like a kind of an immediate company so robinhood this exchange not a media company buys a media company stripe bought indie hackers right stripe not a media company bought indie hackers this community of kinda of makers hubspot buying the hustle and there's a few other ones said that are actually like you know somewhat prominent spotify buying like let's say the ringer or things like that you know there's a few different examples of this so karen take us back so i'm less interested in the like oh what's the future look like because there's a part of that that's interesting but i think for most people that's gonna sound like you know hubspot propaganda basically so what i wanna know is and i genuinely wanna know is i've been on the other side trying to sell my company and the whole time i was like how do i get these mother efforts to buy me like what's going on in those meetings who raises their hand and says hey maybe we should look at this company where we should buy it how do they think about that so can you take us back and i wanna know if you remember even the specific like day where you were like you know what like maybe we should buy the hustle who said it was it you did you say it to what how does that go down on the buyer side yes so we got together last june talking about future growth and one of the things that kip and i talked about is we're just at such a scale now that we're trying to we can't build all the things we wanna build we want to kinda buy and we we were really we focused on content and community so we had pitched before like buying an apps from buying product and hubspot has a very specific thesis around if it would buy a product based company or not but brian the founder was like hey i'm really interested in content community media companies and if you can find something that's a fit you guys have a general strategy or your interest in content community is brian the origin here where he's like hey maybe we should buy one is that kind of how it starts like some titles set brian's the founder brian's finder yeah c cofounder founder ceo brian's the person who we just say hey can we go and go pitch some things like he's not the person telling us where the person people thought so sam said like people thought he was weird whom he was telling about it the first couple of pitches we did even around the hustle people really didn't get it internally for to begin with like we were trying to craft a narrative and took us like a couple of times to get it right in our head but so we go back we're like we're june we're like okay yeah we can go pitch some companies so we went and talk to media companies and i think it was james no it wasn't it was someone internally it said hey if you thought about hustle and i told james who's was on my team hey you go check out the hustle talk to the hustle and that's how we first got connected it was a cold email by the way it was a cold email was it was james right james gilbert yeah james gilbert it was a called email and i've gotten a bunch of those and i've said this before in the last podcast i always thought a b b saas company buys or i thought like a linkedin or a we work i never thought a media company should bias and i saw this email from james and i was like oh this guy's is like a bullshit he just fish was straight like was he straight up saying like we were interested they come forward or was he like let's talk about a partnership or would love to get to know you what was the initial cold email i suspect i bet you was partnership get to know you we i don't think we would ever be maybe maybe you correct me jim i didn't didn't talk to james but his first email but i think the partnership get to know you as usual the usual angle that we versus like straight at it's bayou you that's what i tell other founders too if you wanna get bought you know you have to like approach it like hey things are going so great over here and our customers will keep telling us about you know they want us to work with you guys more would love to see what a partnership might look like and like you know nobody knows what the hell that means but everybody kinda knows what what that means like hey let's let's kick the tires on each other and yeah wayne quick nudge does let's talk can i read this email i suspect you can they will know about the deal that doesn't talk about future stock price alright i'm gonna i'll skim it before i but said hey sam i've been a long time father of you sorry to hear about your recent diagnosis of lime i know it's pretty hectic i hope you're okay and i like that so he goes so we're looking to partner or even acquire content businesses where we think it'd be a right fit and then basically he says is this something you would be interested in talking about and he said by the way i'm also interested in self storage and i think home ownership is not an investment but a consumption point content so we agree on a lot of stuff nice a very good very good cold email right there right that is let's personalized at the beginning then you he dang something that he thought might be interesting for you like why you wanna take time to talk to me and then like kinda build some rapport real quick and shared that this wasn't a generic outreach i got on the call with him and the anna the woman i've been working with i actually don't know where title but she was like my person i was talking to most of the time he's like corp dev right yeah and i told both her and him i go look we get people trying to bias us all the time if you wanna talk tell me right away by the way that's such a funny cocky thing to just say like you say that all the time you're like like get approach all here's what i do you say it with a straight face i would say nine out of ten ceos and entrepreneurs doors don't have the like the lack of i won't even call it the guts i would call it the lack of shame we to just say that with a straight face and like put it out there it's great well i'll tell you why i said that which is i've been through this before and when i early in my career when i've been through with people would jerk you around and they would fish for information and then they would pull you along and like you know this is a good fit and and so i basically just said look we get asked this all the time i've had these conversations most of them are total waste of this time of time so i wanna get to know like right away you're saying partnership i don't know what that means do you wanna buy my company or not and if you do tell me you wanna buy us or at least you're interested in buying us and we could talk and i can tell you a little bit about the company i can send you google doc where i'll write to you and you could say yep we're interested in buying you or at least we're interested in furthering this conversation and i don't wanna waste your time or my time and i hope i didn't come off disrespectful but this is how i feel i appreciate that i send him the thing and they go we're interested let's talk yeah like a single woman who's forty years old and like look i'm not here for a casual date i'm trying to make a baby in the next twelve to eighteen months if you are prepared to make a baby then we should talk otherwise you know you state your intentions right now that's what we did and and they reciprocate and that's one of the reasons why i like them yeah saves you the kinda of dancing end the subject i think that's one of the things that we we liked is just the kind of honesty so karen you said that if you said something like we pitched a couple of companies you know you basically you you you went talk to a couple companies you pitched them internally of like hey here's a company that we might you know be interested acquiring and why why it might be great good idea so you did that with the hustle and you said the first couple times we talked about it didn't quite click so what what does that mean tell like walk us through the actual scenario you're in a room with who and you pitch the you know for twenty minutes you talk about why we should buy this company and what crickets or people say no or what happens the way we go through it is we have a batch companies and there's a couple of us by james predominantly but we'll do a five slider and pitch each other on it and we excited then we'll go a pitch through the finder and the exact team and so the hustle was the only one that we got through the us being excited by it and so we went to pitch the exact team the reason we wanted to do the hustle deal wasn't really the way that we pitch to begin with which is hey we could have this media company we we could have some contextualize hubspot across it and some people may click them out and buy hubspot that wasn't the predominant reason we we were we were kinda not being honest with ourselves about why we wanted to we just wanted the the talent who could build audience on those properties and not the monetization of that software is really second us it's like how do you build big audience in these channels and so the first time we pitch it i think i just came at an angle that i thought people would like but wasn't really the honest reason we wanted to do it i mean we we went back and actually worked a lot with brian be fair brian really helped us set the correct vision because then you have to pitched to the board to help board i spent time going back and forth with him and so the second third iteration and just the narrative got better and so from then on it just got easier to tell a story once you get the story everything else is easier because it's easier to tell it makes sense to people and was sam a risk factor where you like this guy's a wildcard card i think like the very first how we kicked off the show which is like sam never had a boss that's that's the very first thing like that comes up about founders is like how are they going to even adapt to the environment because there's there's some amount of being adapt you have a little other autonomy but you have more kind of reporting structures like the point you made on is like hey what do you actually working on like that's a real thing in companies right and so i think it's about your it's a lot about your do you think you can see this person working within the company because it was really the talent that we were excited by sam was one of those things the other thing is that person like a jerk are they gonna jerk to other people like that's just the a thing that's gonna do so the founders is a big part of it and we thought a lot about how people fell about sam and we talked a lot on slack about how felt about exam yeah how does that make you feel here's what i told them i go when we started a lot of people would call me or the company and when it was when we started it the company was basically kinda just me a couple people they would call us bros you know sean people call us that everyone's like you just wanted to tech bros and i'm like but everyone who listens to us or gets to know us after a while realizes that it's far deeper and there's far more of a richer personality you know i don't think it were offensive so we would like to think i don't yeah no like i i don't think i think that that stereotype is i told them i go i don't think being a bro is bad by the way but i just think it's not an accurate full picture yeah yeah i don't think that that's the truth i mean if you look at our company like for the longest time it's mostly run by women and people from all types of backgrounds what and so i told them i i have a feeling you guys think that i'm like loose cannon in a aha head but hopefully you know i got to know these guys i spent so much time with them i'm like hopefully you can see that there's a lot more to the story and also sean they listen to the podcast so like what better ways there to get to know someone then he's dropping on their conversations yeah exactly when we were getting acquired you know one of the companies was like whining and dining us like crazy like they flew flew us out to their headquarters and my whole team actually other companies were basically like interrogating us right like interviews but the interviews were like you could tell they were trying to like they were vetting us and they were trying to figure out how like get the best price or like who are the week links that we're gonna chop off of this acquisition and not pay for and then the other company was doing the exact opposite they were like whining and dining us flying us around taking us out to an oyster dinner and like you know i had to pretend i knew shit about oysters i don't know shit about oysters and like they're ordering wines they're asking me what i like and i say red and white they're like well which which one and i'm like you know either or you know you you could make some like the old school like at the soda fountain when you fill up your soda with all twelve things you know i was just a fish out of water but i was trying to i was trying to like be a good first date and they were trying to whine and dine then the other companies we're not doing that at all so hubspot is hubspot a wine and diner or are you a more more simple like more of the interrogation type or what's your style i'm curious so sound probably it'll be interesting to see what sound i think it's hard to do what like we just can't do one and dime because we couldn't fly covid by austin and you know because covid i i it was actually one of the things we did talk about is just how difficult this process well as doing it virtually because again this deal is for the most part buying into the team we didn't get spend any time with the team in person that was really really hard we found that difficult i think sam will tell you that i don't wanna speak for sam with maybe find the due diligence was like there was a lot of like digging into the business digging into data and digging into all of the finer details time so i think in this one we were getting to notes trying to get to know the company i don't think we have the opportunity to why and dine what do you think sam i was processed for you there was no wine in dining and frankly i wouldn't have liked that that because i would've have been like oh they're trying to butter me up and then they're gonna low me and from the very beginning it was like alright hubspot your glass door reviews are like crazy good are you guys faking it like what's going on what are you guys lying about and they were like no we don't fake it we don't do this and so i got to know them and it was very at first cordial they're respectful but very straight to the point and after we got to know each other i call it like work flirting like karen and i and andrew the other guy i was working with and anna out like we would joke and you know they would call me late at night sometimes because there were like we had to do and like we were i would be like oh i'm just sitting with my wife and what are you doing and like oh just at my new this new house i'm i'm just like we did like get to know each other and it was more like friendly coworker and that's what i wanted gotta and it was really good everything was to the point but dude sean the diligence was hell i think most deals go to a point they there's two points and and most deal like lifespan there's a walk away point where you just it's at that's early on where you're just you can't agree on the price or the terms of the structure and one side basically walks either threatens to walk away or actually does walk away and then then you can may hopefully reconcile later and then the other one is the almost fall through point where it's like usually a little bit later and all of a sudden something comes out of the wood work or there's some reason where the deal almost falls and somebody has to be like no we're doing this like let's work through this was there a walk away point during the price negotiation and was there a almost full through point later on i'm curious so in my end the price was really sam and and i think andrew and anna so i didn't really get involved in that the not really for us again the reason we would have had a walkway point if something didn't fit within the kind of story we were telling which is a can sam and team get us audience and talent on the challenge that we're not good at we looked at the data but the data and the data was important to us but that wasn't gonna be the reason we would walk away i think the reason we would walk away is we turn around and said i just think sam and his team are just not gonna be happy to have hubspot they're not gonna want to be part of the company that would have been the the red flag for us versus the of the of the data that that's funny i thought the data was so important and they were asking for so much of it we are a data we are a data that t and is important like let's say half of your traffic was the bot think that's another thing you're looking at into you we actually legally were like asking hey and it's this is this bots or at these people who stopped for the email wheeler they open in the email there's like just data that you have to have signed off on to be able to go and do the deal that's for any deal i think that would be true for anyone who's doing this kinda of deal there's just if you're fake data or the data is accurate and for my point of view i actually tried to get them to bail many times so so i actually tried to tell them all everything bad upfront and i wanted to say like look like i actually downplayed it i was like you were like protecting yourself you didn't want it to fall through later you're like look if you're gonna if you're gonna break up with me just break up with me now yeah and so i was i was like really my heart can't take was like here's so be kick butt here's where we suck here's the numbers that stink here's the numbers that rock take it or leave it that's sam's version of a sw analysis edit it like no i mean never done all done correctly but like at one point in the negotiation or in the due diligence process sean they're asking for like podcast numbers or something and like i couldn't figure out how to export something and i just go i'm just taking a screenshot and i just would take screenshots and set of or they would be like hey can we log in and see this this and this i'm like no i'm not gonna give you a login but i'll tell you what and it'll like i did like a a loom video where i would like click through i'm like here's this here's this it was definitely pretty funny during that process that's cool alright alright i like it what else is there so i'm digging for for all the drama of that position because i'm i i think that that's like it's one of those things that entrepreneurs go through so few times in your life you kinda feel like i felt like at least i was going through it blind right didn't know how the hell to do it you know there's only a handful of people have successfully done it you gotta go talk to them each deal is so unique and has all of these like little specific context things that don't apply to to other people's situations and so that's why i'm asking all these little questions about how the deal came about and when it almost broke apart and all this good stuff kieran can i actually ask you a question yeah okay so first of all i'm wanna talk about lawyers in a second because working with lawyers was a trip but before we talk about lawyers so like i'm a horrible negotiator sean because people will say alright i'm gonna make this up they'll they'll say alright we're gonna give you eight and most people are like well if you want nine say ten and hopefully someone will give you nine right i don't do that and i think that's a huge miss what what do you do instead let's say i want ten and they offer eight i go it's ten the numbers ten take it or leave it and i thought like oh people will appreciate this straightforward and like no games i don't think that people appreciate that i think that or not that they don't appreciate i think that that give and take looking back at what i know is actually useful and it's actually a huge missing attribute of my business acumen so the advice that i got when i going through i should have given you this earlier but too late but basically i was like i thought i was a good negotiator right i used to play poker i thought okay i can i don't know how these pots go down i know how to how to bluff i know how to bet i know how to whatever i asked this guy who was helping us with the deal he was like a banker so he's done many many transactions i said hey can you listen in i'm gonna record myself doing this part the conversation or we could do like a role play and let's just tell me if i'm doing it right and because i don't know when are they gonna talk about price are they gonna ask me for a number are they gonna come with a number how it gonna work you know am i doing it too am i doing too a little i recorded my my reaction to it i thought i did great and your example they said eight i wanted ten i asked twelve right and i thought okay i did the thing and he was like yeah you don't wanna do what you just did and i was like well what do you mean he goes think about it like this in a hand of poker what do you really want you know the first thing is you wanna win but if you don't win what's the second best thing you can get this information he's like you're giving away so much information so quickly and he's like don't give anything don't react and he's like they're gonna ask you for a number and you're gonna say i don't know you can play the good guy card and you're basically like you know price is secondary to us it's really it's about the right fit of course like prices super primary in many cases the way i look at it is price primary and fit is the deal breaker if there's no fit or if of price close between two or three options then you go with the better fit if they ask you for a number you give them no information you say and you don't know you'll have to think about it blah you come back to them i was trying to do all this complex anchoring and all this other shit no don't do it same thing where they came with the price also don't react you say appreciate you guys coming forward with an offer that's really helpful so we can think about this i'm gonna you know take some time to digest this and i'll get back to you that's it and he just like and then he's like you get back to them later we'll talk about it we'll figure out what to do next and so that was the main thing i was doing wrong with i was just giving out too much of a signal whether this was a good offer or a bad offer i didn't need to give any signal and in fact that darkness actually made them feel like it was too bad of an offer every single time and they would just come back and negotiate with themselves because i would just go dark for like a period of three days and they just took that as like oh my god we're way off and it was better than me saying any number and so that was the advice i got and i i started taking i wish i told you that a little sooner well i actually saw some of like then they offer people gigs and everything and i had actually saw a house i got to see how each person negotiated and i would agree sean i think your method that method you from what i know across this thing and my friends things and that is the better way people know the eight to twelve to ten anything that i've ever negotiated people come back with hire offer and the first thing we say is that's a real number the numbers in between what you said john i think is like if you have information like if you get to understand why that company want your company like how important is it is to them is there any other companies like yours they're talking to like what's your bargain and power like information i think is is part are so let's actually talk about that because sean here's what's interesting they had a legal team i know how much my lawyers cost and i would see who was on different invites to the meetings and it would be karen who is an i don't know if you're you're an executive yeah an executive vp so executive at hubspot so probably very expensive and then like the cmo would join this legal team would join all these other people would join and in my head it didn't hit me till later on i'm like oh my gosh this is costing them a ton of money i told my friend jack i was like i don't know if i wanna do this and frankly i even know if they want this and he goes like dude like they've spent all this time on this they want this if they're saying they want it they want it it's gonna take a lot to mess it up at this point and i was like oh my god you are so right because you have to think from their perspective like karen just pitch this to brian and he bought in and then brian or i i'm guessing this someone it went brian then pitch this to the board so like all these people first of all no one wants to look dumb second of all they spent probably a fair bit of money if you wanna like add up the salaries and i'm like oh shoot they're in i need to relax that was something i wish i knew better because you kinda have like guess we have self doubt you're like oh they don't really want me this is it's the biggest transaction of your life right right it's the company you just spent a huge chunk of your you know life building it's gonna be life changing and it's also gonna be you know potentially heartbreaking breaking if it goes wrong so that's a lot of room for that little brain of ours to like come up with crazy ass stories and and start telling yourself wild things and that's why you need i call them deal do like if you've ever i think probably the hardest thing is giving birth when you're going through labor having a do is really helpful to kinda talk you through it and keep you calm and keep you breathing so i call them deal do list to help you get through a deal and like bert that baby right and so i gave this talk at at at the last hustle con actually about how to sell i called out how to sell a failing company because i think if your company is just kicking ass and i think you guys are more like this you guys are kicking ass people come to you all the time trying to buy you and it's really about just finding the right fit and price and then and going with it you know when your company is not like you're not instagram you're not just taken off it takes a little more finesse to do a deal do you guys watch it's always sunny in philadelphia the tv show yeah i don't i don't i've heard of it i don't watch it so it's basically a show about a bunch of assholes being assholes and it's really funny the main guy or one of the main guys dennis he does this episode called the dentist system and the dentist system is about dating he's like this is my full proof way to get sort of like maximize my sort of dating or whatever and the dentist system i think is almost a perfect system for selling a company for exiting so d is the first step demonstrate value right why do i even wanna buy oh i have a two million person email list i don't know what the number is forty percent of people open it every morning we have trends we make all this money you know that's demonstrating value and you did that part right you sent over that doc you said that that it laid out the good parts of the company e is engaged physically that's his for dating but i think it's the same thing for doing a deal which is you need to meet the people and hit it off like meeting you know you the other execs and saying oh yeah that person's really awesome we want them to be a leader in our company that's like really important then it's nurture dependence and this is like i think the key thing which is you have to build yourself as a solution to the bigger company's problem so like let's say i'll just speculate for a second one of the reasons you want a solution like the hustle where you have this team of people who's really good at growing audience and trusted audience of kind of business owners and maybe hubspot has has face challenges in growing that audience organically great software great customers but how do you grow like an audience of people around content that might be hard so then you if you've nurtured dependents it's you've basically planted to see that if you want the thing you want we're the best way to get there and then the funny part is like the end which is you neglect emotionally you inspire hope and then you separate entirely before closing the deal and my acquisition went down almost exactly like that we even had the end the separate entirely where it was like hey this does not happening winning we're going with this other party i'm sorry i'm about to sign this thing that makes it so i can't negotiate with you anymore but i just wanted to say it's been great knowing you and that was the like core trigger to like finalize the deal actually did either of you do anything crazy to to celebrate selling on your companies did you ever have like when i sell this company i'm going to go buy something do something so right when this dealing went down me and sam hopped on club house i think it was sam's first time on club house and i asked sam through question but i think it's worth repeating on the on the podcast so the first question i asked is what did you what did your parents say when you told them or are they found out they just said like i think they say said like what what's the health care and like and like so like do you have health insurance like do you have a job for your health care and like do you have a job and like and is it a real company yeah that's that's the first one i asked the second is what's your kind of like what's your pop champagne purchase you're gonna do like are you gonna splurge buy something like you know what are you gonna do with the money sam so my not the irresponsible part what do you what's the irresponsible okay so a few things first i bought pizza so we had a big pizza and then i ate some cake and then i my wife wants michelle obama's outfit from the inauguration she like said that as a joke one day and i was like alright great i'm gonna get it for you and then i am gonna get a fun car cool okay so i think that's that's interesting and then the the third question i had is like okay your life just changed does it feel like your life just changed because the the money has hit the bank now correct and did you just look at it for like ten minutes or what happened no you wanna know what i did was last year i used this thing called personal capital you know what that is it's like a money tracking thing kinda like a budgeting and money manager for yourself personal finance app yeah so i manually added a bank account you know you can edit it and i made it a really big number and so i was like okay so this is what it feels like to have before before before the this year before months ago a year ago i did it i go this is what it feels like they have this and then i was excited and then i like spent weeks and like i'm like okay this didn't didn't pack my happiness at all like it did a little at first and then i was like shit i'm back to normal a was it maybe because it was a fake number that you input do you think that's why because it was monopoly money no because i i feel no it it's also like it's just this thing on the screen it's so anti anticlimactic and karen you've been at hubspot now for eight years eight years okay so your a vp their stock has gone up sean i think the ipo at like was it fourteen dollars i think we went fourteen twenty dollars and now it's four hundred and twenty or something like that today i don't over four hundred so surely you've had that moment where it was like oh my gosh this is like more you know it's a lot it feels a little anti anticlimactic magic do you not agree sean or karen well karen and i wanna hear yours yeah it's interesting like an interesting talk i went shoot before i i used to always tell people like accidentally join the cult this thing called neuro linguistic programming it's not a cult but there's cult elements of it and i and i was going for it for the kinda goal set part and i ended up in this kind wacky wacky group of people there was one talk i went too much i i felt was really and i was always stuck with me which is you you're either motivated towards something or you're motivated away from something and you can actually be a mixture of both so when i was growing up we had a an amazing childhood but not much money and so i always wanted enough money to not have to worry about money which just kinda like pushing away from versus when i had money no one what to do with it like i didn't have like things i was like us i won't really wanna get this fancy thing that fancy thing so for me the benefit of having some success in tech was just that not having to be a core warrior of mine versus kinda like i'm gonna the thing that makes me happy is like be up to do something for my parents be able to do something for for my family and not don't have to worry about it i think that's that's been the main advantage what about you sean and all has this quote that i like which is like he like when i was younger it was all about having the freedom to do something like oh i want the freedom to go on this boat or freedom to you know live wherever i want have mansions in different places right you want you want the freedom to do certain stuff and he's like the older i got it became freedom from like i'm a freedom from having to be you know having a ninety five job or having to be in one place at any given time we're having to worry freedom for having to worry about money or worrying about health or whatever else you know and i think that's that's an important shift and because i think freedom two never ends freedom to you know you just start to desire bigger and bigger shiny objects but freedom from there actually is a very small list of things that bring you misery or suffering and you can kind of like wipe those out and then you you might replace them with new things and you you that you start to like suffer from because you you know you're you're just addicted to having problems but i think for most people if you wipe out you know the freedom from problems it really does impact your quality of life that's why i don't believe the like oh money doesn't buy happiness and i would say like yeah i don't know what the right way to phrase it is but money does definitely buy off misery it gets misery to go the fuck away there's definitely some suffering that you just stop having when you have money because the money can solve that problem it has its own set of problems and it doesn't solve all problems that that's that part is true how does you feel i felt extreme relief that was the only thing and it part of it is like you know your time about the diligence phase the diligence phase is just really stressful because you know nothing good can happen out of diligence like let's say they're doing due diligence in your company it's not like they're ever gonna be like oh man we really think this is great we're gonna triple the price no but they can multiply it by zero and say inside never mind we're not doing this deal so diligence i feel like is this no upside only downside few months and it's this weird couple months and so by the end of that i just felt relief that the deal actually done the money's is actually in the bank you know my team is actually they have their signed offers they know what they're doing my investors got their money they're you know they feel good about that that was just relief and then i was like okay what do i do now and i had set out a long time before that that like i really just wanted to buy two things when when i had much money and one was infinite socks so i just wanted to have like i just wanted to have whatever the best sock is on the market i wanted to have like three hundred pairs of that identical socks so i never have to worry about socks mismatch socks laundry i just wanted socks and so that was like dab the house elf just really wanted to sock and said that was like my main thing i wanted to buy and then the other was like okay i wanna now ask myself different questions like you know one of the reasons this podcast called my first million was because i really wanna be a millionaire that was an important goal to me wasn't gonna listen to all the rich guys you already made millions that we're trying to tell me that making money isn't where it's at i was like sure which is what we're doing right now yeah well well that's why i'm kinda laughing right it's like i think that's the cycle of an entrepreneur right you he's you start broke you start building stuff you get rich to they you tell everybody yeah don't do what i did and like i didn't wanna be that i actually generally i enjoy big rich i think it was a great thing and i'm not gonna lie to people and tell them you know it's not great i think it's fucking great the part that's great you know because the socks were instant perk but the real perk is being able to say alright if before i was working for money right like whether i was honest about it or i wasn't i was doing shit because i thought was gonna make me money if i no longer need money right if i if money is not the biggest concern anymore what do i do with my time what is the most enjoyable way to spend my time and what projects would i work on if money wasn't the main thing i was optimizing for which some smart people are able to do earlier in life than i am i wasn't able to do it until after i actually had a lot of fear my biggest fear it wasn't necessarily that the deal was gonna not go through my fear was you just said what would you do if you didn't have money and you know what i would do sean if i have money i would start a media company and or i would start blogging and that's how this company started right i've just started blogging that's how i express myself are you saying that's what you do would do if you didn't have money and you needed money or you're saying if you didn't need to work for money what would you do your blog is that which which one is i would blog i would write i did that for fun it didn't make money at first i didn't think it was gonna make money i did it for fun i'm happy now that i still get to do that but my biggest fear was identity you know like for years even when people thought i was an idiot and they probably still do but even my mom and dad were like dude just get a job this stupid thing is like this is dumb this internet thing like what do you you don't have a real job you're just on your computer you're not wearing a nice shirt you're like you can't be working from the couch like this is dumb this is fake even when i told him about airbnb they're like this is not real and then of course you don't have to note but my biggest fear was it screws your identity because you've just married yourself to this i am the hustle or i am whatever i do for a living that is a a weird weird feeling right like sean is the guy who runs monkey inferno and works out of this fancy office like that that is him and you are closing that it's not ending but it's evolving that is the weirdest thing in my opinion yeah in fact that's still weird because even now if somebody's like oh you know what do you do or like kinda like if i have to run a bio some somewhere i'm like oh yeah i'm a founder or someone the last company computer switch i don't write my current twitch job title there because it just feels so foreign to me to be like i don't even know my job it's like senior director of some some fucking thing i i like if i write that i'm like that's not me i don't know what that is and it's not that i don't do the job or enjoy the job it's just weird to put my identity as that because for so long i wrote my identity as on the founder of x and so i'm it's very hard for me to still say i'm not the founder of x because it was like ten years straight of saying that twelve years and you know you're thirteen to just be like no now you know here's my business card i i'm an employee at this company it was it's very strange to me still and i think that my situation is a little bit different because i'm gonna be doing this podcast i'm gonna be blogging i'm gonna be writing i'm gonna be doing all this stuff for a long time so it's definitely different it's weird having that identity change yeah i'm so thankful that i don't you never had to work because you had an accounting team right yeah we had back office here i hated doing all this accounting stuff i hated doing monthly financials i hated trying to negotiate people's bonuses i hated that so much of the point that every once in while would call in sick because i'm like i just i can't face this meeting i can't like i hated it so much and so i'm so thankful i don't have to worry about that so i'm that i am relieved as well as excited so kieran what okay if somebody's listening to this podcast and they're like oh shit this is like what is this the hubspot podcast now what's gonna change so they wanna hear it from you from the horse's mouth directly what should they think about the future of this podcast if you're if you're a loyal listener yeah like people who love the podcast what it is and our entire exec team listen to this podcast there's no change like hopefully the things that we can do is just invest more and the things that sam this team wanna do for us we we we bought the properties and we bought we bought the hustle because we love the work they do if we didn't we thought like hey this content is way far off from the kind of stuff that we wanna produce there's no point buying it because the amount of it effort you have to do to like start to change that and the team is not gonna be happy so not gonna be happy so the thing that we love to buy sam is i think one of the early meetings he was like the thing i wanna do is just build the biggest business content network and that's one of the terms we've started using after talking to some in that's what we wanted to do like we wanna be the go to destination for people are entrepreneurs startups and scale ups and people love this podcast and hopefully we can just make it more successful but mike can making it more visible in all of the stuff that we do and i'll tell a story for the readers or listeners i met with brian recently and he goes you know i think i said this on told the story yesterday and i've i've been telling you a ton but sean he goes there's one big problem i have with this deal and i was like oh my god you're gonna yell at me already what did i do i was thinking up my head like did i do anything did do anything and he goes my fear is that somehow you get in here and you guys dull it down he goes you know how austin has a slogan keep austin weird i'm gonna get a big sign i'm gonna put it in front of the hustle i'm gonna say keep the hustle keep saying keep trying keep everyone keep sean keep them weird and not only are we not gonna make your weirdness go away or your your just go away i hope we absorb some of it and we learn from you guys and i was like alright alright that's sounds good to me i love it that's like when when peter t invested in airbnb i think he put like a hundred million dollars in or something like that and this is back in twenty twelve where airbnb wasn't super proven out we're so glad to have you on board you know you invest in facebook early on you know what's the single most important piece of advice you could give us it just wrote back a one line email that just said don't fuck up the culture and you know i i thought that was pretty bad let me ask you one more question we got a few minutes left i wanna do something that anyone who's in the situation of wanting to start and sell something you said earlier i don't think we can build this as like a little entrepreneur of a small business in my head i'm like dude you guys have so much money you can hire anyone you can build anything you want what are you talking about just throw like spend a ton of money and get it done it's really hard for me to understand from your perspective why you are buying versus building can you explain from a huge company's perspective why you do that and how someone just starting out can exploit that to where it's they get bought and you guys or whoever wins exploiting in a good way yeah and let me because we talked about this a lot so i don't know if it's that i we couldn't build it but there's an opportunity cost right like you would have to we would have to go and find the talent that you find we would have to go and create the brand around the podcast the trans community but the hu community like there's just an opportunity cost that we would have to say okay all of this other stuff we have planned we put on ice because we're not gonna to a pivot and start to focus on these things so i think when you're thinking about it is just like can you get from a to like b to c in a faster fashion and for us when we look in terms of can we buy or build it was how long would it really realistically take us to hire the talent you've acquired how long is it gonna help realistically gonna take us to create something that people love as much as hustle this podcast the trans community and it just doesn't make sense given all of the other things we wanna do and again we don't wanna get into in the future but there was just the perfect fit of the stuff that we would have to kinda start from scratch or start from a point where we're kinda like fine we were doing a fine job of and build those out versus just getting a team in and getting those properties in and start and at a for a hire base and so i think for entrepreneurs there's some there's a huge the the thing that i took away for because this is the first deal i've done there's a couple of things i took away like there's some amount of luck right it's just a moment in time there was a moment in time that all of the stars is aligned that i think the re the way we got connected to you is i talked to someone internally they mentioned the hustle i mentioned it to james and we were in the process of thinking about media companies i think three months right earlier three months after we actually had started to talk to freemium apps and we had mine have move past that and we might have like we couldn't find a media company so i think there's a moment in time the team that you build is so important like the talent you have within your company is a core part of why you sign off in the deal they if you go in and you have a good finder and you have a couple of good execs then you have like a weakest team the deal will not get through there's just so much thought goes into the team and the talent you acquiring then then you have to have something i think you have to have something special i think the the hustle has you guys are perfect is a type of content that fits the business audience but it's differentiated from everything else it's not like you could buy the hustle and or you could buy these other five companies who all kind of produce the same content there's a certain edge to your content it's nice mix of business comedy journalist research and i think it's hard to find that in any other kind of business that we looked at when you say it like that it sounds pretty fucking smart i i like it sam good job i don't even know if you knew you were doing all that maybe it's the irish accent but like i get this like conor mcgregor like it's inspiration i mean like at licking in the back of sean's room we talked day before we're both conor mcgregor fans the date i think it was a day before the fight or two days for the fight i haven't wanted to think about it since that was a bad weekend he called and we were supposed to talk about this deal and the podcast and you know what does it mean for the podcast to get acquired and instead he saw the conor mcgregor president i'm i well we talked about conor mcgregor for forty nine minutes of the for like eleven i'm an m mma nuts this is great insight i think this is fun to hear this i'll i'll wrap up by saying two things one i don't know sean a few experiences lawyers first of all what a hard job that you have and it is crazy to work with lawyers i haven't worked with lawyers as close but that was a wild experience and second now working and selling to a public company you we gotta be careful you know like even if you're making a joke if you say something wrong that mislead someone that's gonna be an interesting experience and now that i know what i know to see for example what day port is doing with penn stock how is that guy not sued i don't get it yeah so i'm a little like they've been telling me you know i've been getting educated on the process and like this is no longer like company policy like this is like sec like laws right and so i'm very aware and and trying to learn about all that process i don't know if you went through that showing but i had a funny situation like that where because we when we got acquired we got amazon stock and so i was diversified i sold like i like ten percent of my position because i wanted to invest in some other things and i was just talking about it casually with somebody else who works there and they were like oh but the trading window is not open right now i was like well i mean the stock market's is open he's like no no like the amazon like you know like we employees we you know if you're employee of an amazon company there's a trading window you have to trade within that time period like x out of the quarter you can only trade these times you can't trade near the earnings call or right right before right after something like that and i was like oh fuck that's what that email that i don't open says like there's this email every every month that's like important the trading window is open and i just never open it i was like what did i just go to jail and then i was like shit okay i was like emailed the general counsel and i was like hey steve like listen i made a big mistake you know i sold some my stock just now outside of the trading window let me know what i need to do i'm sure it's a big process blah blah blah blah i'm sorry for the headache he belly back and it was like good news bad news he's like yeah good news it's all fine because you're are you're not like disclosed to any inside information like basically the bad news is like oh dude you're you're not your level you're not how important enough to have like real information material information and i like why to argue you because i was so like what do you mean they're talking about promoting me right now actually like dude i know everything and i was like never nevermind i this is not the time to let my ego put me in jail so so i was like you're right i don't know shit i i don't know nothing to you're right so in the future karen i i don't know like we haven't really said what's gonna happen next but i think we could be vague but like we're gonna do more stuff right we're gonna do more stuff i think the you and i talked this sound like we're gonna spend all the time this but we love the things that you're doing and then you have some other ideas that we there was honestly we spent the first month talking about one of your other ideas more than we talked about anything else we're like oh this could be a blog this could be this this this and this and so the good news is that we're serious about building the media company win and helps hubspot and that means we have resources and ambitions to do it and so we're gonna do more i mean well we'll you we this is big enough we're gonna do a lot more content so if you i guess we're gonna have to start recruiting people so if you if you're listening and you think you're great and you wanna be the next sean wanna be the next super superstar out i don't know if i'm there yet but you wanna be somebody we'll have to we'll have to recruit you yeah anyone who's telling to come come check it out and we didn't even actually properly introduce you so give us everything yeah you're you know what's your day what's your job and where do people find you on social if they wanna like catch more of you karen oh yeah so here fine again i'm a sv of mark in the hubspot just letters and i was gonna embarrassed with this part you can find you on twitter at search prep at the one of the worst handles you could picked it's dude that's a great search brett you're like i think that's great i shouldn't really got my name i was early on twitter i got my name on the club has that's the best place to or hit you up linkedin night since we did the deal i have like three hundreds connections are probably all trying to sell me something on linkedin and kieran flanagan dot io o kira finding in dot io o but growth tl l d r dot com as well that's yours too right that is the podcast that i do not as good as this podcast that's right alright well we're gonna pick them all out this is cool i imagine kieran gonna be coming back on another time but this is fun i'll bra you what do you think that was great we kinda did a mini version of that yesterday with t but this version was was really cool people gonna get pissed they're gonna be like to diet sam as i was i didn't get to talk to you yesterday said trunk asked a bunch of questions about the deal and then i asked you a bunch of questions people are back dude we get it you got acquired enough enough about the deal if you're tired of heard about the deal i promise we're gonna keep it to a minimum going forward but i wanted to know this stuff and that's basically our outlined for the podcast is like what does sam i wanna talk about what do i wanna talk about and like that's it well no i think some of the stuff karen just said i didn't know and so hopefully like someone listens to us and they could steal it all and go sell their company or going buy another company because hopefully they can kinda use this as a little bit of a information session for doing that so thank you karen thank you sean we out alright so yeah