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

Yeah. I feel like I can rule the world, I know I can be what I want to Uh Put my all in it like my day's off travel never looking back Mm.

Okay, we are live. I'm back. Sam is here and Sam who's who's this other gentleman we got? All right, so we have Kieran here, Kieran Flanagan. Who is gonna be speaking from HubSpot's 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 want to focus on. I'm excited to learn. So I'm pumped. Kieran, I hope you're pumped. Uh so what is someone more emotional 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 um Yeah.

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? Or like a wild dog who now has an own. I'm like, what is this l 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, this guy, Doug, and uh 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 Uh like an update every week on what you're up to. And I was like, Oh yeah, that's what I always ask people who kinda report to me. I just hadn't reported to anyone in so long that I was used to only writing like a

like an investor update every every month or every quarter. And uh this guy was probably like, How come this guy doesn't talk to me uh like at all? And now I was like, Oh yeah, shit, my bad. I got you. So we had um The deal's done. I got that approved, by the way. I can say that, Kieran. We announced it last week. It was announced last week. It's kind of 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 Kieran to come on because we could have his perspective because I think this was him and the CMO of Hubsbot. I think it 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 be cool to have his perspective because I think this is gonna happen a ton. And like Me and Kieran and and the rest of the folks at HubSpot, 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 t 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 is 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 roadmap. So I we could talk about that. So there's a few of these, right? I saw this in the trends group uh and then I stole it and tweeted it. But basically like you know, Robin Hood bought uh Snacks, which was like a kind of a media company. So Robin Hood, this exchange, not a media company buys a media company. Stripe bought indie hackers. Right, Stripe, not a media company bought indie hackers' community of kind of makers.

Hub spot buying the hustle. And there's a few other ones that 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 Kieran, take us back. So I'm less interested in the like, oh, what's the future look like? Cause there's a part of that that's interesting, but I think for most people that's gonna sound like You know, hub spot propaganda, basically. So I what I want to know is and I genuinely want to know is um 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 effers 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, maybe 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? Who did you say it to? What how does that go down on the buyer side? Yeah, so we got together last June talking about future growth and one of the things that Kip and I have talked about is We're just at such a scale now that we're trying to We can't build all the things we want to build. We want to kinda buy and we

We were really focused on content and community. So we had pitched before like buying apps and buying product, and Hubstart 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 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? Put some titles to Brian's the founder and Brian. Yeah. Co founder, CEO. Brian's the person who

We just say, Hey, can we go and Go pitching things. Like he's not the person telling us. We're the person people thought so Sam said like people thought he was weird when he was telling them 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 uh 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 talked to some media companies and I think it was James. No, it wasn't. It was someone internally and said, Hey, if you thought about the hustle, and I told James, who's 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. I was It was James, right? James Gilbert. Yeah, James Gilbert. It was a cold email and I've gotten a bunch of those and I've said this before in the last podcast. I always thought a B to B SAS company should buy us, or I thought like a LinkedIn or a We Work. I never thought A

Media company should buy us. And I saw this email from James and I was like, Oh, this guy's like a bullshitter. He's just fishing. Like was he straight up saying like we were interested in did he 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 it. 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 I didn't talk to James about his first email, but I think the partnership get to know you is usual the usual angle that we versus like straight out that's by you. That's what I also tell other founders too. If you want to get bought, you know, you have to like approach it like hey Things are going so great over here and our customers are 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 quick nine stars let's talk partnership. Can I read this email? I suspect you can. People know about the deal. As long as it doesn't talk about future stock price. Alright, I'm gonna I'll skim it before I meet, but he said uh

Hey Sam, I've been a long time follower of you. Sorry to hear about your recent diagnosis of Lyme. I know it's pretty hectic, but 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 uh 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 homeownership is not an investment, but a consumption point. So we agree on a lot of stuff. Nice. A very good, very good cold email right there, right? That is uh that's personalized at the beginning. Then you he dangled something that he thought be interesting for you, like why you want to take time to talk to me.

And then like kind of build some rapport real quick and showed that this wasn't a generic outreach. I got on the call with him and the uh Anna, the woman I've been working with, um, I actually don't know her title, but she was like my person I was talking to most of the time. Like Corpdev, right? Yeah, and I told both her And him, I go. Look, we get people trying to buy us all the time.

If you want to 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 we can approach all the time. Here's what I said. And you say it with a straight face. I would say nine out of ten CEOs and entrepreneurs don't have the like the lack of, I won't even call it the guts. I'm gonna call it the lack of shame. 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 f early in my career when I've been through it, people would jerk you around and they would fish for information and then they would pull you along and like uh you know this isn't a good fit. And I and so I basically just said look We get asked this all the time. I've had these conversations. Most of them are a 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 want to buy my company or not? And if you do Tell me you want to buy us, or at least you're interested in buying us, and we could talk. And I could tell you a little bit about the company. I can send you a 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 want to 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 them the thing and they go. We're interested. Let's talk. You're like a single woman who's forty years old and is 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, stay state your intentions right now. That's what we did. And and they reciprocated, and that's one of the reasons why I like them.

Yeah, it saves you the kind of dancing around 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 uh You said something like we pitched a couple of companies, you know, you basically you you you went talked to a couple of companies, you pitch them internally of like, Hey, here's a company that we might, you know, be interested in acquiring and why, why it might be a great good idea. So you did that with the hustle and you said the first couple times we talked about it, uh 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 of companies and there's a couple of us kit by James. Predominantly, but we'll do a five slider and pitch each other on it and we're excited then we'll go to pitch to the founders and the exec 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 pitched it to begin with, which is hey, we could

have this media company, we could have some contextualized HubSpot across it and some people may click on that and buy HubSpot. That wasn't the predominant reason we we were we were kind of 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 into software is really secondary to us. It's like how do you build big audience in these channels? And so the first time we pitched 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. And then we w 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 pitch through the board, the hops up 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 the story. Once you get the story, everything else is easier because it's easier to tell. It makes sense to people. And was Sam uh a risk factor? Were you like this guy's a wild card? I think like the very first how we kicked off this show, which is like Sam's never had a boss. That's that's the very first thing like that comes up about founders. It's like

How are they going to even adapt to the environment because there's there's some amount of being adapt. You have still a lot of autonomy, but you have more kind of reporting structures. Like the point you made, Sean, is like, hey, what are you actually working on? 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 a sound is one of those things. The other thing is that person like a jerk. Are they going to jerk to other people? Like that's just the a thing that's going to So the founder is a big part of it, and we thought a lot about how people felt about Sam. And we talked a lot on Slack about how we felt about Sam. Sam, 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 and a couple people.

They would call us bros. You know, Sean, people call us that every once in a while like you just want 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 a far more of a richer personality. You know, I don't think that we're offensive. So we would like to think. I don't yeah, no. I like I I don't think I think that that stereotype is what 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 to 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. And so I told him, I go, I have a feeling you guys think that I'm like a loose cannon and a hahead, but hopefully you know, I got to know these guys. I was spent so much time with them. I'm like I 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 way is there to get to know someone than eavesdropping on their conversations. Yeah, exactly. When we were getting 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 Interroging 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 to like get the best price or like who are the weak 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 and 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 can mix them like the old school, like at the soda fountain when you fill up your soda with all 12 things. Um, 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 wine and dine.

And then the other companies were not doing that at all. So Hubspot uh is HubSpot a wine and diner, or are you a uh more more simple, um like more of the interrogation type? Or what's your style? I'm curious. Sam could probably it'll be interesting to see what Sam thinks. I think it's hard to do w like we just can't do one and die because we couldn't fly to fly the Austin. Yeah,'cause of Covet. I I it was actually one of the things we did talk about is just how difficult this process was. doing it virtually because Again, this deal is for the most part buying into the team. We didn't get to 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 want to speak first time, but the 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. So I think in this one, we were getting to know Sam, trying to get to know the company I don't think we had the opportunity to do wine and dine. What do you think, Sam? I was processed for you. There was no wine and dining, and frankly, I wouldn't have liked that. Oh, they're trying to butter me up and then they're gonna lowball me.

And From the very beginning. It was like all right, hub spot. 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, 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, this other guy I was working with, and Anna, like we would joke and you know, they would call me late at night sometimes'cause they're like we had stuff 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, I'm just at my new air this new house, I'm I'm designed like we did like Get to know each other and it was more like friendly co worker. And that's what I wanted. 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 have there's two points in in most deal like lifespans. There's a walk away point where you just it's that that's early on where you're just you can't agree on the price or the terms or 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 woodwork or s there's some reason where the deal almost falls through and somebody has to be like, No, we're doing this, let's let's work through this. Was there a walkaway point during the price negotiation and was there a almost fall through point later on, I'm curious. So in my end the price was really Sam and and I think Andrew and Anna. Uh so I didn't really get involved in that. The not really for us. Again, the reason we would have had a walk away point if something didn't fit within the kind of story we were telling, which is a c can Salmon 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 going to be the reason that we would walk away. I think the reason we would walk away is we'd turn around and say, I just think Sam

And his team are just not gonna be in happy and have spot, they're not gonna want to be part of the company. That would have been the the red flag for us versus the manuscript of the of the data. 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 tea it is important. Like let's say half of your traffic was The bots. Like that's another thing you look at too, right? We we actually the legally were like asking, Hey, is this is this bots? Or these people he sign up for the email wheel are they opening the email? There's like

Just data. That you have to have sign off on to be able to go and do the deal. That's for any deal. I think that would have been true for any anyone who's doing this kind of deal. There's just if you're faking data or the data's not accurate. And from 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 up front.

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 so I was like really My heart can't take I was like, here's how we 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 SWAT analysis. No, I mean it was done uh all done correctly, but like At one point in the negotiation

We're in the due diligence process, Sean. They were 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 send it to them. 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. 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 uh funny during that process. That's cool. All right. All right. I like it. What else is there? So I'm digging for for all the drama of the acquisition 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 kind of 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 who have successfully done it. You got to go talk to them. Each deal is so unique and has all these like little

specific context things that don't apply to each 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. Karen, can I actually ask you a question? Yeah. Okay. So first of all I'm gonna talk about lawyers in a second. 'Cause working with lawyers was a trip. But

Before we talk about lawyers, so like I'm a horrible negotiator, Sean, because people will say, All right, I'm just mixing this up. They'll s they'll say, All right, 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. W what do you do instead? Let's say I want ten and they offer eight, I go

It's ten. The number's ten. Take it or leave it. And I thought like, oh people will appreciate this straightforwardness 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. It's actually useful. And it's actually a huge missing attribute of my business acumen. So the advice that I got when I was going through it. I should have given you this earlier, but uh 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 of the conversation, or we can 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's it gonna work? You know, am I doing too much? Am I doing too little? I recorded my my reaction to it. I thought I did great. And your example, they said eight, I wanted ten, I asked for twelve, right? And I thought, okay, I did the thing. And he was like, Yeah, you don't want to 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 want to win, but if you don't win, what's the second best thing you can get? It's 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. Really, it's about the right fit. And of course, like price is super primary in many cases. The way I look at it is price is primary and fit is the deal breaker if there's no fit. Or if price is 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 You don't know, you'll have to think about it, blah, blah, 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 a price. Also don't react. You say I 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 was 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, was 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 had told you that a little sooner. Well, I actually saw some of like then they offer uh people gigs and everything, and I had actually saw how I got to see how each person negotiated. And I would agree, Sean. I think your method that method you Well 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 higher offer and the first thing we say is that's not the real number, the numbers in between. What you said, Sean, 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 bargaining power? Like information I think is is power. So let's actually talk about that because uh Sean, here's what's interesting. They had a legal team. I know how much my lawyers cost and I would see who is on different invites to the meetings, and it would be Kieran who is an I don't know if you're oh 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 join and in my head it didn't hit me until 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 don't 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 Kieran just pitched this to Brian and he bought in. And then Brian, or I I'm guessing this is how it went. Brian then pitched this to the board. So like all these people First of all, no one wants to look dumb. Second of all, they spent a probably a fair bit of money if you want to 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 I guess you have self doubt. You're like, Oh, they don't really want me. This is it's the biggest transaction of your life. 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 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 doula's. Like if you've ever I think probably the hardest thing is uh giving birth when you're going through labor, having a doula is really helpful to kind of talk you through it and keep you calm and keep you breathing. So I call them deal doula to help you get through a deal and like birth that baby, right? And so I gave this talk at at at the last hostile con actually. about how to sell I called it how to sell a failing company because I think if your company's 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 taking off, it takes a little more finesse to do a deal.

Do you guys watch It's Always Sunny in Philadelphia, the T V show? Yeah. 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 um it's really funny. The main guy or one of the main guys, Dennis, he does this episode called The Dennis System. And the Dennis System is about dating. He's like, Oh, this is my foolproof way to get to like maximize my sort of dating or whatever. And the Dennis 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 want to buy? Oh, I have a two million person email list. Well, I don't know what the number is. 40% of people open it every morning. Uh, 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 engage physically. That's his for dating, but I think it's the same thing for took a deal, which is you need to meet the people and hit it off. Like meeting, you know, you, the other exec, 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 dependents. 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, maybe HubSpot has has faced 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 nurture dependents, it's you've basically planted a seed 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 to the separate entirely, where it was like, hey, this is not happening. We're going with this other party. I'm sorry. I'm about to sign this thing that makes it so I can't uh negotiate with you anymore. But 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 your companies did you ever have like oh when I sell this company I'm going to go Buy something, do something. So right when this deal went down, me and Sam hopped on Clubhouse. I think it was Sam's first time on Clubhouse. And uh I asked Sam three questions, 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 uh when you told them or they found out? They just said like uh I think they say like what what's the healthcare? Uh and like so do you have health insurance? Do you have it? And is it a real company? Yeah. That's that's the first one I asked. The second is uh uh what's your kind of like what's your pop champagne purchase you're gonna do? Like are you gonna splurge and buy something like you know what are you gonna do with the money sample? So um my not the responsible part. What do you what's the irresponsible part? Okay, so a few things. First.

I bought pizza. So we had a big pizza. Um and then I ate some cake. And then uh my wife wants uh Michelle Obama's outfit from the inauguration. She like said that as a joke one day and I was like, All right, great, I'm gonna get it for you. And then I am gonna get a fun car. Cool. Okay. So I think that's uh 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? Uh'cause the m the money has hit the bank now, correct? And uh did you just look at it for like ten minutes or what happened? No. You wanna know what I did was last year I use this thing called personal capital. You know what that is? It's like a money tracking thing. Kind of like a budgeting and moneager for yourself. Personal finance app. Yeah. So I manually added a bank account, you know, you can add it in 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 the before the state. Before months ago, a year ago I did it. I go, This is what it feels like to have this. And then I was excited and then I like spent weeks and like I'm like Okay, this didn't impact my happiness at all. Like it did a little at first, and then I was like shit, I'm back to normal. Was it maybe because it was a fake number that you inputted? Do you think that's why? Because it was monopoly money? No, because I I feel uh no, it but it's also like it's just this thing on the screen. It's so anticlimatic. And Kieran, you've been at HubSpot now for

Eight years? Eight years. Okay, so you're a VP. Their stock has gone up, Sean. I think they IPO'd 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 anticlimatic. Do you not agree, Sean or Kieran? Well, Kieran, I wanna hear yours. Yeah, it's interesting. Like I an interesting talk I went to before I I used to always tell people I accidentally joined the cult, um this thing called neurolinguistic. It's not a cult, but there's cultish

elements of it and I and I was going for it for the kind of goal setting part. And I ended up in this kind of wacky, wacky group of people. There was one talk I went to which I I felt was really And it's 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 an amazing childhood, but not much money. And so I always wanted enough money to not have to worry about money, which is kind of like pushing away from versus when I had money knowing what to do with it. Like I didn't have like things I was like, Oh, it's one really wanna get this fancy thing, that fancy thing. So for me, the benefit of having some success in tech was

Just m that not having to be a core worry of mine. Versus kinda like I'm gonna I the thing that makes me happy is like Be able to do something for my parents, be able to do something for For my family and not have to worry about it. I think that's

That's been the main advantage. What about you, Sean? Nivelle has this quote that I like, um, which is like he's 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 um He's like the older I got, it became freedom from. Like I want freedom from having to be, you know, having a nine to five job or having to be in one place at any given time or having to worry, freedom from having to worry about money or worrying about health or whatever else, you know? And I think that's um That's an important shift and because I think freedom to 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 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 you 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's that part is true. How did you feel? I felt extreme relief. That was the only thing. And a part of it is like

You know, you're talking 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 a 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, never mind, we're not doing this deal. So diligence, I feel like is this no upside only downside few months. And um, it's this weird couple months. And so by the end of that, I just felt relief that the deal's actually done. The money's 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 ha 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 a bunch of 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 pair of that identical sock. So I never have to worry about socks, mismatching socks, laundry. I just wanted socks. And so that was like I'll be the house elf, just really wanted a sock. And so 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 wanted to be a millionaire. That was an important goal to me. I wasn't gonna listen to all the rich guys who already made millions that were trying to tell me that making money isn't where it's at. Uh 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 you s you start broke, you start building stuff, you get rich, and then you tell everybody, you know, don't do what I did. And like I didn't want to be that. I actually

Genuine, 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 the being able to say, all right. If before I was working for money, right? Like whether I was uh honest about it or I wasn't, I was doing shit because I thought it 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 f 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 didn't 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? You'd blog. Is that which which one is it? 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 when 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 uh told'em about Airbnb, they're like, This is not real. And then of course, you know, now they know, 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 kind of like if I have to write a bio somewhere somewhere, I'm like, Oh yeah, I'm a founder, I sold my last company with Twitch. 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. I was like senior director of some s 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. Cause for so long I wrote my identity as I'm 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, year thirteen to just be like, No, now I'm 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, but I'm so thankful that I don't you never had to work because you had uh an accounting team, right? Uh yeah, we had back office, yeah. 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 to the point that every once in a while I would call in sick because I'm like, I just 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, uh, as well as uh Excited. So Kieran, what okay, 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. Uh what should they think about the future of this podcast, if you're if you're a loyal listener. Yeah, I think People who love the podcast for 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 in the things that Sam and his team want to do.

For us we we we bought the properties and we bought we bought the hostel because we love the work they do, if we didn't if we thought like, hey, this content is way far off. From the kind of stuff that we want to produce, there's no point buying it because the amount of in effort you have to do to like start to change that and the team's not gonna be happy, Sam's not gonna be happy. So The thing that we loved about Sam is I think one of the early beat in C 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 Sam. That's what we wanna 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 make it 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 the song told the story yesterday and I've I've been telling it 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? Um I was thinking of my head, I'm like, Did I do anything? Did I 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 the slogan, keep Austin weird. I'm gonna get a big old sign. I'm gonna put it in front of the hustle. I'm gonna say, Keep the hustle, keep Sam, keep Trunk, keep everyone, keep Sean, keep them weird. And Not only are we not gonna

make your weirdness go away or your your edgyness go away. I hope we absorb some of it and we learn from you guys. And I was like All right. All right. That sounds good to me. I love it. That's like uh when Peter Thiel invested in Airbnb, uh, I think he put like a hundred million dollars in or something like that. And this was back in twenty twelve where Airbnb wasn't super proven out. We're so glad to have you on board. You know, you invested in Facebook early on. You know, what's the single most important piece of advice you could give us? He just wrote back a one-line email that just said, Don't fuck up the culture. And uh, you know, I I thought that was pretty badass. 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 exploit in a good way. Yeah, and let me uh'cause we talked about this a lot. So I don't know if it's that uh 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 found. We would have to go and create the brand around the podcast, the trends community. The host community, like There's just an opportunity cost that we would have to say, Okay, all of this other stuff we have planned, we have put on ice,'cause we're not going to So

I think when you're thinking about it it's 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 our build, it was how long would it really 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 the hustle, this podcast, the trans community?

And it just doesn't make sense given all of the other things we want to do. And again We don't wanna get into that again in the future, but it 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 kind of like fine, we're doing a fine job of. And build those out versus just getting a team in and getting uh those properties in and starting at a for a higher base. And so I think for entrepreneurs, there's some there's a huge the thing that I've 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 aligned that

I think the we 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. Earlier or three months after we actually had started to talk to Freemium apps.

And we had might have moved 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. Like if you go in and you have a good finder and you have a couple of good execs, then you have like a weakish Team. The deal will not get through. There's just so much thought goes into the team and the talent you're acquiring. And then you have to have something, I think you have to have something special. Um, I think the The hustle has

You guys are perfected. 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 a nice mix of business comedy. Journalistic

Research I think it's hard to find that. in any other kind of business that we looked at. Well 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 Connor McGregor like inspiration. I mean look at look in the back of Sean's room. We talked the day before. We're both Conor McGregor fans. The day I think it was the day before the fight or two days before the fight. I haven't wanted to think about it since it 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 Connor McGregor poster on my wall and we talked about Connor McGregor for forty nine minutes and for like eleven. I'm an MMA nuts.

This is great insight. I think this is fun to hear this. I I'll I'll wrap up by saying two things. One, I don't know, Sean, if you experience this, lawyers. First of all What a hard job they have. And it is crazy to work with lawyers. I haven't worked with lawyers as close. 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 misleads someone, that's gonna be an interesting experience. And uh now that I know what I know to see, for example, what Dave Portnoy is doing with pen stock. How is that guy not sued? I don't get it. So I'm a little uh 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 um

aware and and trying to learn about all that process. I don't know if you went through that, Sean, but I had a funny situation like that where um'cause we when we got acquired, we got Amazon stock. Uh and so I was diversifying'cause I sold like I don't know, like ten percent of my position'cause I wanted to invest in some other things. And um I was just talking about it casually with somebody else who works there and they were like, Oh, but the trading window's not open right now. I was like, Well what do you mean the stock market's 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 training 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 of my stocks 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. I'm sorry for the headache.

He bail me 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 any inside information. Like basically the bad news is like, oh dude, you're you're not your level, you're not important enough to have like real information, material information. And I like wanted to argue 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 oh never mind. I 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. You're you're right. So in the future, Karen, I I don't know, like w 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've talked about this sound like we're gonna spend all the time on this, but we love the things that you're doing and then you had some other ideas that we

There was w 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 uh We're serious about building the media company, a win in HubSpot, and that means we have resources and

Ambitions to do it. And so we're gonna do more I mean, we'll we can this is vague enough. We're we're gonna do a lot more content. So if you uh I guess we're gonna have to start recruiting people. So if you uh if you're listening and you think you're great and you wanna be the next Sean, you wanna be the next superstar. I don't I don't know if I'm there yet, but you wanna be somebody, uh we'll have to we'll have to recruit you. Yeah, anyone who's talented, come uh come check it out. And we didn't even actually properly introduce you, so give us everything. Uh your you know, what's your name, what's your job, and where do people find you on social, uh if they wanna like catch more of you, Karen. Oh yeah, so uh Hier and Fan again, I'm a S V P of marketing in the HubSpot. Uh just letters and uh I always get embarrassed with this part. You can find me on Twitter at Search Bratt. It's one of the worst handles you could have picked. It's a Oh dude, that's I think that's a great way. Search Brat? You like I think that's great. I should have really got my name. I was early on Twitter. I got my name on Clubhouse. That's the best place or hit me up and link down the low since we did the deal.

I have like Three hundred connections are probably all trying to sell me something on LinkedIn. And Kieranflanagan.io. Kieranflanagan.io. But growth T L D R dot com as well. That's yours too, right? That is the podcast that I do. Not as good as his podcast. That's right. We'll we're gonna pip them all out. This is cool. I imagine Kieran's gonna be coming back on another time, but this is fun. Uh Bra you, what do you think? That was great. We kind of did uh a mini version of that yesterday with Trunk, but this version was was really cool. Are people gonna get pissed they're gonna be like, dude, Sam, I was I didn't get to talk to you yesterday, so Trung asked you a bunch of questions about the deal.

And then I asked you a bunch of questions. People be like, dude, we get it. You got acquired. Enough of enough about the deal. If you're tired of hearing about the deal, I promise we're gonna keep it to a minimum going forward. But I wanted to know this stuff. And uh that's basically our outline for the podcast is like, what does Sam wanna talk about? What do I wanna talk about? And like That's it. Well, no, I think some of the stuff Kieran just said I didn't know. And so hopefully like someone listens to this and they could steal it all and go and sell their company or go and buy another company because hopefully they can kind of use this as a little bit of a information session for doing that. So

Thank you, Karen. Thank you, Sean. We out. All right. See ya.

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