#153 - Selling The Hustle for Millions: How The Hustle & Hubspot Deal Happened
Okay, we are live. I'm back. Sam is here. And Sam, who's this other gentleman we got?
All right. So we have Kieran here, Kieran Flanagan, who is going to 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 am 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.
So what does 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 going to learn that. I don't know, like, everything. I feel like I'm— I feel like I'm a kid who, like, was at an 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 wild dog who now has an owner.
I'm like, what 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, 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 kind of 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 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 HubSpot. 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 going to happen a ton. And like me and Kieran and the rest of the folks at HubSpot, we were like, you know, I don't care about awards. 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 kind of cool that like we're going to do, it's going to 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 we could talk about that.
So there's a few of these, right? Is I saw this in the trends group, uh, and then I stole it and tweeted it, but basically like, you know, Robinhood bought, uh, Snacks, which was like a kind of a media company. So Robinhood, this exchange, not a media company, buys a media company. Stripe bought IndieHackers, right? Stripe, not a media company, bought IndieHackers, this community of kind of makers. HubSpot buying The Hustle. And there's a few other ones that are actually somewhat prominent. Spotify buying, let's say, The Ringer or things like that. 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? Because there's a part of that that's interesting. But I think for most people, that's going to sound like HubSpot propaganda, basically. So what I want to know is, and I genuinely want to 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 motherfuckers 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 want to know if you remember even the specific day where you were like, you know what, maybe we should buy The Hustle. Who said it? Was it you? Who did you say it to? 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 kind of buy, and we were really focused on content and community. So we had pitched before like buying apps and 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 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?
Brian's the founder, yeah, co-founder, CEO. Brian's the person who we just say, "Hey, can we go and go pitch some things?" He's not the person telling us. We're the person. People thought— Sam said people thought he was weird when he 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 it 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, have 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 B2B SaaS company should buy us, or I thought like a LinkedIn or a WeWork. 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.
Was he straight up 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 it was partnership, get to know you. I don't think we would ever be, maybe you correct me, Jim, I didn't talk to James about his first email, but I think the partnership, get to know you is usually the usual angle that we versus like straight out, let's buy 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 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 kind of knows what that means. Like, hey, let's, let's kick the tires on each other.
And yeah, Wayne Quake nods. 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.
All right.
I'm going to— I'll skim it before I read it. All right. But he said, hey, Sam, I've been a longtime 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 home ownership is not an investment, but a consumption point. So we agree on a lot of stuff.
Nice. 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 might be interesting for you, like why you want to take time to talk to me. And then like kind of built 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.
She's like corp dev, 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, we get approached all the time.
Here's what I said.
And you say it with a straight face. I would say 9 out of 10 CEOs and entrepreneurs don't have the, like, the lack of, I I won't even call it the guts. I'm going to 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, 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, ah, you know, this isn't a good fit. 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 want to 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. They go, we're interested.
Let's talk. You're like a single woman who's 40 years old and is like, look, I'm not here for a casual date. I'm trying to make a baby in the next 12 12 to 18 months, if you are prepared to make a baby, then we should talk. Otherwise, you know, 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 went and talked to a couple of companies, you pitched them internally of like, hey, here's a company that we might 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, it didn't quite click. So what does that mean? Tell us, like, walk us through the actual scenario. You're in a room with who, and you pitch that, you know, for 20 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, there's a couple of us, Kit, I, and James predominantly, but we'll do a 5-slider and pitch each other on it. And if 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 us being excited by it. And so we went to pitch the exec 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 were kind of not being honest with ourselves about why we wanted to. We just wanted 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 went back and actually worked a lot with Brian. To be fair, Brian really helped us set the correct vision, 'cause then you have to pitch to the board, the HubSpot 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 'cause it's easier to tell. It makes sense to people.
And was Sam 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 the very first thing like that comes up about founders. It's like, how are they going to even adapt to the environment? 'Cause 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? 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, and Sam was one of those things. The other thing is that person like a jerk? Are they being a jerk to other people? Like that's just 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, the company was basically kind of just me and a couple of people. They would call us bros, you know, Sean, people call us that every once in a while. You're like, you're just a bunch of 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 that we're offensive.
So we would like to think.
I don't think, yeah, no, like I don't think, I think that that stereotype is 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. 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 was mostly run by women and people from all types of backgrounds. And so I told them, I go, I have a feeling you guys think that I'm like a loose cannon and a hothead, 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 way is there to get to know someone than eavesdropping on their conversations?
Yeah, exactly. When we were getting acquired, you know, one of the companies was like wining 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 to like get the best price or like who are the weak links that we're going to chop off of this acquisition and not pay for.. And then the other company was doing the exact opposite. They were like wining 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 can mix them like the old school, like at the soda fountain when you fill up your soda with all 12 things. You know, I was just a fish outta 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, is HubSpot a wine a wine and diner, or are you a more simple, like more of the interrogation type, or what's your style? I'm curious.
So Sam can probably, it'll be interesting to see what Sam thinks. I think it's hard to do, like we just can't do wine and dine because we couldn't fly to Austin. Because of COVID Yeah, because of COVID 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, and 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 for Sam, but maybe from 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 wine and dine. What do you think, Sam? How was the process for you?
There was no wine and dining. And frankly, I wouldn't have liked that because I would've been like, 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, HubSpot, your Glassdoor 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 and 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 Ana, like we would joke and, you know, they would call me late at night sometimes because they're like, we had stuff to do. And like we were, I would be like, oh, I'm I'm just sitting with my wife and what are you doing? And like, oh, I'm 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. 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 walkaway point where you just, it's a, 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 you can 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 there's some reason where the deal almost falls through and somebody has to be like, no, we're doing this, let's work through this. Was there a walkaway point during the price negotiation? And was there an almost fall-through point later on? I'm curious.
So on my end, the price was really Sam and I think Andrew and Anna. So I didn't really get involved in that. Not really for us. Again, the reason we would have had a walkaway point if something didn't fit within the kind of story we were telling, which is like, 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 going to be the reason that 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 going to be happy at HubSpot. They're not going to want to be part of the company. That would have been the, the red flag for us versus the minutia 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-led team. It is important. Like let's say half of your traffic was bots. Like that's another thing you look into, right? We actually, the legal were like asking, hey, is this bots or these people who sign up for the email real? Are they opening 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 have been true for 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 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 going to, if you're going to break up with me, just break up with me now. Yeah.
And so I was, I was like, really, my heart can't take it. I was like, here's where 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 SWOT analysis.
And it like, uh, no, I mean, it was done, uh, all done correctly, but like at one point in the negotiation or 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. And I'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, 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, cuz 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 gotta go talk to them. Each deal is so unique and has all these like little specific context things that don't apply to you, 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 want to 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, all right, I'm just make this up. They'll say, all right, we're going to give you 8. And most people are like, well, if you want 9, say 10, and hopefully someone will give you 9.
Right.
I don't do that. And I think that's a huge miss.
What do you do instead?
Let's say I want 10 and they offer 8. I go, it's 10. The number's 10. 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, is 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 record myself doing this part of 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 going to talk about price? Are they going to ask me for a number? Are they going to come with a number? How's it going to work? Am I doing too much? Am I doing too little? I recorded my reaction to it. I thought I did great. In your example, they said 8, I wanted 10, I asked for 12, 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? The first thing is you want to win. But if you don't win, what's the second best thing you can get? 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 going to ask you for a number and you're going to say, I don't know. You can play the good guy card and you're basically like, price is secondary to us. Really? It's about the right fit. And of course, 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 2 or 3 options, then you go with the better fit. If they ask you for a number, you give 'em 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, 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 is 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 3 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 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 8 to 12 to 10. 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 number's 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 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 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 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 want to 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 going to 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'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 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 kind of have like, I guess you have self-doubt. You're like, oh, they don't really want me.
This is the biggest transaction of your life.
Right.
It's the company you just spent a huge chunk of your life building. It's going to be life-changing and it's also going to be 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 start telling yourself wild things. And that's why you need— I call them deal doulas. Like if you've ever— I think probably the hardest thing is 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 doulas to help you get through a deal and like birth that baby, right? And so I gave this talk at the last HustleCon 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 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 TV 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 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 sort of 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 you? Oh, I have a 2 million person email list. Well, I don't know what the number is. '40% 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 engage 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, 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 nurtured dependence, 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 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 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 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 3 questions, but I think it's worth repeating 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, I think they say like, what's the healthcare? Uh, and like, like, so like, do you have health insurance?
Do you have a job?
What's your healthcare? And like, do you have a job? And like like, uh, 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, buy something? Like, you know, what are you gonna do with the money, Sam?
So, um, my—
not the responsible part, what do you— what's the irresponsible?
Okay, so a few things. First, I bought pizza, so we had a big pizza, um, 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, all right, great. I'm going to get it for you. And then I am going to get a fun car.
Cool. Okay. So I think that's, uh, that's interesting. And then the third question I had is like, okay, your life just changed. Does it feel like your life just changed? Uh, cause the money has hit the bank now. Correct. And, uh, did you just look at it for like 10 minutes or what happened?
No, you want to 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 money manager 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 this. Before, before this deal, 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. 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 feel, no, it's also like, it's just this thing on the screen. It's so anticlimactic. And Kieran, you've been at HubSpot now for 8 years?
8 years.
Okay. So you're a VP. Their stock has gone up, Sean. I think they IPO'd at like Was it $14?
I think we went $14, $20.
And now it's $420 or something like that today. I don't— over $400. 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 anticlimactic. Do you not agree, Sean or Kieran?
Well, Kieran, I want to hear yours.
Yeah. It's interesting. Like I, an interesting talk I went to before I used to always tell people I accidentally joined a cult. Um, this thing called neurolinguistic programming. It's not a cult, but 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 felt was really, has always stuck with me, which is 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, I really want to 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 worry of mine versus kind of like, I'm gonna— the thing that makes me happy is like being able to do something for my parents, be able to do something for my family and not have to worry about it. I think that's been the main advantage.
What about you, Sean?
Naval has this quote that I like, 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 live wherever I want, have mansions in different places. Right. You want the freedom to do certain stuff. And he's like, the older I got, it became freedom from. Like, I want freedom from having to be having a 9 to 5 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. And I think that's an important shift because I think freedom to never ends. Freedom to, 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 wipe those out, and then you might replace them with new things that you start to suffer from because you're just addicted to having problems. But I think for most people, if you wipe out 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, that's, that part is true.
How did you feel?
I felt extreme relief. That was the only thing. And part of it is like, you know, you're talking about the diligence phase. The diligence phase is just really stressful cuz you know, nothing good can happen out of diligence. Like let's say they're doing due diligence on 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, nevermind, 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 there. 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 I just wanted to have whatever the best sock is on the market. I wanted to have like 300 pairs of that identical sock so I never have to worry about socks, mismatching socks, laundry. I just wanted socks. And so that was like Dobby 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 want to 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 going to 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. I was like, sure.
Which is what we're doing right now.
Yeah. Well, that's why I'm kind of laughing, right? It's like, I think that's the cycle of an entrepreneur, right? You, 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 generally, I enjoy being rich. I think it was a great thing. And I'm not going to 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, all right,, right? 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 it was going to make me money. If I no longer need money, right? 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 going to 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 I would start blogging. And that's how this company started, right? I just started blogging. That's how I express myself.
Are you saying that's what you 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 going to 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 them 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 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, I'm like, oh yeah, I'm a founder. I sold my last company to 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 title. I was 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. Cuz 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 cuz it was like 10 years straight of saying that, 12 years. And you know, year 13 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's 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. Change. But I'm so thankful that I don't— you never had to work because you had 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 as well as 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 going to change? So they want to hear it from you, from the horse's mouth directly. What should they think about the future of this podcast if you're a loyal listener?
Like, 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 bought the properties and we bought the hustle because we love the work they do. 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 effort you have to do to like start to change that and the team is not going to be happy, Sam's not going to be happy. So the thing that we loved about Sam is I think one of the early meetings he was like, the thing I want to 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 want to do, like we want to be the go-to destination for for people who are entrepreneurs, startups and scale-ups. And people love this podcast and hopefully we can just make it more successful by 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, told the story yesterday and 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 going to yell at me already. What did I do? I was thinking in 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 a 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 Truong, keep everyone, keep Sean, keep them weird. And not only are we not gonna make your weirdness go away or your edginess 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 when Peter Thiel invested in Airbnb, I think he put like $100 million in or something like that. And this was back in 2012 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 thought that was pretty badass.
Let me ask you one more question. We got a few minutes left. I want to 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 where it's they get bought and you guys, or whoever wins, exploit in a good way.
Yeah. And let me, uh, cuz 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 trans community, the hustle 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 cuz we're now going to pivot and start to focus on these things. 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 or build, it was how long would it realistically take us to hire the talent you've acquired? How long is it going to help— realistically going to 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 want to. And again, we don't want to get into that kind of the future, but it was just the perfect fit of the stuff that we would have to kind of 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 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, 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 the stars aligned that I think 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 3 months earlier or 3 months after, we actually had started to talk to freemium apps, and we had might have moved past that, and we might be 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 on the deal. Deal. I think if you go in and you have a good founder and you have a couple of good execs and 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. I think the Hustle has, you guys have perfected a type of content that fits the business audience, but it's differentiated from everything else. It's not like you can buy the Hustle and or you could buy these other 5 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. And 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 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, 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 2 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 Conor McGregor poster on my wall. We talked about Conor McGregor for 49 minutes and the deal for like 11.
I'm an MMA nut.
This is great insight. I think this is fun to hear this. I'll wrap up by saying 2 things. One, I don't know, Sean, if you experienced 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 got to be careful, you know, like even if you're making a joke, if you say something wrong that misleads someone, that's going to be an interesting experience. And, uh, now that I know what I know to see, for example, what Dave Portnoy is doing with Penn 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 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. So I sold like, I don't know, like 10% of my position because I wanted to invest in some other 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. And 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 an 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 minute. I was like, what? Did I just go to jail? And then I was like, shit. Okay. So I 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 emailed me back and it was like, good news, bad news. He's like, you know, good news, it's all fine because you are, you're not like disclosed to any insider information. Like basically the bad news 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. 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 don't know nothing.
You're right. So in the future, Karen, I don't know. Like, we haven't really said what's going to 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 have talked about this, sound like we're gonna spend a lot of time on this, but we love the things that you're doing. And then you had 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 were 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 within HubSpot, and that means we have resources and ambitions to do it.
And so we're going to do more. I mean, we can— this is big enough. We're going to do a lot more content. So if you, uh, I guess we're going to have to start recruiting people. So if you, uh, if you're listening and you think you're great and you want to be the next Sean, you want to be the next superstar— I don't know if I'm there yet, but you want to be somebody, uh, we'll have to, we'll have to recruit you.
Yeah, anyone who's talented, come, come check it out.
And we didn't even actually properly introduce you, so give us everything. Uh, you know, what's your name, what's your job, and where do people find you on social, uh, if they want to like catch more of you, Kieran.
Oh yeah, so, uh, Kieran Flanagan. I'm a SVP of marketing at HubSpot, uh, just letters. And, uh, I always get embarrassed for this part. You can find me on Twitter @searchbrat. It's one of the worst handles you could have picked.
It's a— oh dude, that's— I think that's a great 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 on LinkedIn. Although my— since we did the deal, I have like 300 connections. They're probably all trying to sell me something on LinkedIn.
And kieranflanagan.io. kieranflanagan.io. Yeah, but growthtl.com as well. That's yours too, right?
That is the podcast that I do. Not as good as this podcast.
That's right. Well, we're going to pip them all out. This is cool. I imagine Kieran's going to be coming back on another time, but this is fun. Abreyu, what do you think?
That was great. We kind of did a mini version of that yesterday with Trung, but this version was really cool.
Are people going to get pissed? They're going to be like, dude, Sam, because 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 would be like, dude, we get it, you got acquired. Enough about the deal. If you're tired of hearing about the deal, I promise we're going to 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 want to talk about? What do I want to 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 an information session for doing that. So thank you, Kieran. Thank you, Sean. We out.
All right, see ya.