7 Brutal Questions for a $20B Founder

We were constantly like sales forces going to crush us tomorrow. Did you steal their announcement? We're dead. Like I said, that's so many times. (upbeat music) ♪ I feel like I could rule the world ♪ ♪ I know I could be what I want to ♪ ♪ I put my all in it like no days ♪ - I'm excited to be on your show. - It's kind of our show, Brian. - Yes, true. - You consider yourself retired? - I don't think I'll ever retire. - But you're not the CEO of a company. - No. - I have a whole bunch of interesting stuff going on. - Are you happier in this phase of your life than when you were running a $20 or $30 billion company? Or how about happier compared to when you were running a $10 million company? Where's like your levels of happiness been? 'Cause you've founded a company that is now has, I don't know, five, six, seven thousand employees, billions in revenue. Now you're retired and you're not retired, but you're not running a company and you're a little bit of a VC and advisor. So tell me about your happiness levels between each one. - Okay, I'm gonna give you like the grading system in my head for number of employees. Zero, like two to 10 employees, I was like a C. I didn't really add, I could write code but no one wanted it, like I didn't, you don't add a lot of value at that phase. - 10 to 100, I was like an A. I felt like I knew what I was doing. I had been in, you know, scale ups before 100 to 1000. You know, maybe A minus, I kind of felt like I knew what I was doing. A thousand to 10,000. I didn't enjoy the secret of life's enjoying the passage of time. I wasn't really enjoying the passage of time. It was a lot of, I was just working on a lot of stuff I wasn't that interested in. So yeah, so it depended on where I was in the history of HubSpot and I had sort of CEO market fit between 10 and 1,000. That's like you're putting 100 to 1000 at the same category. That's kind of astounding to me. That doesn't seem like those should be in the same category. So you enjoyed that whole range equally. - Yeah, I worked when I, my first job out of school. I was the first BDR at a company called PTC. It's a CAD software company. And I joined, it was like three million in revenue. And when I left, it was, you know, billions in revenue. So I sort of saw that journey and I was part of that machine. And so, you know, I took a lot of that and brought it with me into HubSpot. And I just felt like I knew what I was doing in there and I was working on things I really enjoyed. There's a lot to changes between 100 and 1,000. I just sort of remember being quite motivated and happy with my day to day in there. Very little wary in that phase about what the NAM and GOV committee of the board thought, very little interaction with our compliance and legal folks, things like that. Mostly just working on, you know, the employee's productive and happy or the customer's productive and happy. Like really focused on that. And I like that type of work. - Can you go, okay, so your categories were two to 10, 10 to 100, 100 to 1,000 and then 1,000 to 10,000. What about how hard you are working? Like in terms of hours? - Yeah, people's up one, nine, nine, six. That was at least that for both our mesh and I. We were pedals to the metal the entire time. And if we weren't working, we were thinking about working. It's not for the faint of heart. And like if you look at my life, it's kind of interesting, like I'm 58. In the years I should have gotten married and had a bunch of kids, I had HubSpot. I'm still single. And yeah, you're kind of married to your company and you're full on like the nine, nine, six thing. It's at least that for the founders. And I work with a lot of founders today. It's that's a minimum for the founders. I would say these days. - And you guys said something on a tweet that I thought was. - You said it. That I thought was kind of interesting. Like when you're a founder, like 90% of the time stuff's broken and you're dealing with problems and things kind of suck. - I'm angry, I'm angry most of the time. - Most of the time. - 10% of the time is like, we got this. We got it. Everything's going our way. The winds are back. But it's pretty rare. Like you live your day looking at your slack and your inbox and your tech. So that's mostly bad news in there. - Well, so tell me, once a company gets to a hundred or a thousand employees or 10,000 employees, does that emotion go away? Same. It's the same ratio. It's still, mostly you should say much in your inbox. - Did you feel existential threat? Like my business, we have plenty of money and very profitable, whatever. But for some reason, I still feel like an existential threat all the time where it's like, if we don't do this well, we're going out of business suddenly. Did you see their announcement? We're dead. - Yeah, we tend to overestimate where competitors do and underestimate what we do. - Maybe there's a correlation between like how like, shitty you think you are and how good of an entrepreneur. You make because maybe there's no correlation, but there's like a correlation between people who start businesses because I noticed that I have like, I personally have very negative self-talk where it's like, you're shit. You're nothing. You have to prove them wrong. You are horrible. You barely grow. You can't do this. You have to put like, and it wears people out though because I actually think that that's negative. That's a pretty poor way to motivate people. But it motivates me. - I'm the same and that people say, you know, you want to be very positive and positive and motivate the people. I tend to be paranoid. I still, after all these years, have imposture syndrome. I'm a little nervous talking to you today. Believe it or not. (laughing) - Really, why? - Yeah, and not it's given all the success I've had. My confidence doesn't eat a remote. - Well, it's like you can do it. And my inner monologue is like, you got so much to prove, dude. Don't fuck it up. - Does our match feel the same way? - Yeah. I can't say for sure, but I think very much so. - Do most other, so you run in a circle with some of the best entrepreneurs on earth, the most successful entrepreneurs on earth. Is that the common thread? - Yes. - Almost all of them. - I interview all these CEOs and I ask them during the interviews, you know, do you have imposture syndrome? I mean, they have them, hun-haw. 'Cause they don't want to say they do. They do. Almost all of them. - Let me ask you one more question about all of this. And then I want to know about what your, like more of the Sequoia stuff, 'cause I think that's super fascinating. Sometimes, I think that with being an entrepreneur, the hard part, I would think about this a lot, and I've talked about it a lot, which is the hard part emotionally, isn't the risk-taking. The risk-taking is actually not that challenging, because in a lot of cases, the risk is not that big, and you could, like, even if you go big, you can kind of land somewhere and be all right. The hard part is the uncertainty. And like, asking yourself, am I spending time for the next six or 24 months on this thing? And will it actually make my life better or get me to where I think I want to go? That uncertainty part is quite challenging. Looking back, was dedicating all this time, like, do you look back at the last 20 years, and you're like, that was a life well-lived, or would you have changed anything? - No. - I think it was. I'll take the trade off. It was just a lot of fun. I mean, there was just a lot of joy, and the people at HubSpot are amazing. The customers are amazing. I think part is amazing. So many, so many happy times. A lot of down days, but like the updates, definitely outweigh it. I'm super proud of what we built. You know, yeah, I wouldn't trade it. The thing I would say about HubSpot, that it's a little bit of what you said, but I think of it as like HubSpot was like, two steps forward, one step back. Two steps were, one step back. It looks like, oh, if you look at the grass, like, ooh, that was an easier eye, it wasn't. Like, we had lots of issues and lots of problems and lots of setbacks along the way. And it's a little bit, I think what good entrepreneurs do, is they just stick with it. Like, there's problems and issues and that step back, and they don't fold. They just like, we're gonna get through it. We're gonna rally the troops. We're gonna figure out, we're gonna learn from that, the states, and go forward. Almost all the stepbacks were self-inflicted. All right, a few episodes ago. I talked about something, and I got thousands of messages asking me to go deeper into explain, and that's what I'm about to do. So I told you guys how I use chatGBT as a life coach or a thought partner. And what I did was I uploaded all types of amazing information. So I uploaded my personal finances, my net worth, my goals, different books that I like, issues going on in my personal life and businesses. I uploaded so much information. And so the output is that I have this GPT that I can ask questions that I'm having issues within my life. Like, how should I respond to this email? What's the right decision knowing that you know my goals for the future, things like that? And so I worked with HubSpot to put together a step-by-step process showing the audience, showing you the software that I used to make this, the information that I had chatGBT asked me, all this stuff. So it's super easy for you to use. And like I said, I use this like 10 or 20 times a day. It's literally changed my life. And so if you want that, it's free. There's a link below. Just click it into your email. And we will send you everything you need to know to set this up in just about 20 minutes. And I'll show you how I use it again 10 or 20 times a day. All right, so check it out. The link is below in the description. Back to the episode. What would you have done differently to not make that mistake? One of the things we did that worked-- we had a thing that we did called the Pop-O report. And we live in Boston in this time of year's pop-olds everywhere. And that was the analogy we used at HubSpot. We would create these pop-holes. And sometimes you kind of bounce through the pop-hole and it would hurt a little bit. Sometimes the pop-hole got so big like you drive your whole damn car in it. And oftentimes, there was a series of decisions or a series of data that we could have avoided the pop-hole. So the pop-hole report was, every time we had a pop-hole, we'd look back and like, how should we have handled this a year ago so that wouldn't have happened? Or what data do we wish we had? Now, give me an example of it. We had a pop-hole in like 2011. One of the things we did at HubSpot is we hired really good support people. And our secret sauce and hiring support is would walk into an Apple store, would buy an iPhone, and would hire the kid who sold us the iPhone. And they wouldn't let me in the Apple store and they were gin and marketing art so many people. And so the value prop was great. It's like, you make a little bit more money, but I'd like to sit down at work. It was a really good value prop. How many support people did you have? We must have had 40, 30, 40. And then what we would do is we use that support group to promote into CSNs, into sales, into products. So we fed the whole company really these Apple store people that were terrific. And there's one particular period of time over like a few months. Like we promoted a bunch of people out, congratulated the promoter of them. And then we were a little behind on hiring and the customer numbers were way up. And so we pride ourselves on like answering the call within 30 seconds and then staying on as long as they wanted. And our wait time went to like 20 minutes and customers were like, what the hell was going on? That was a very solvable, predictable problem that if you just looked, this is one chart. We won't make that mistake. Yeah, we never make that mistake again. So so many things like that along the way. And as you grow, if you're growing fast, everything breaks. People break processes, break systems, break. Like everything's just breaking, breaking, breaking with skill. What I've noticed, particularly talking to people on MFM is that it really takes like eight or nine years to see something become a real thing. Yeah, it takes a lot longer than people think. I think HubSpot, if I remember correctly, I think you guys were at 20 million revenue by year six, which is like pretty huge. I think that what we're seeing right now about software companies growing faster, I don't think a lot of those guys are going to last. I think that there is a correlation between how fast something grows and potentially how fast it can die. But I do think that in order to build something that's a second mountain business. And so I've referred to a second mountain business as something that's beyond just making your initial like financial security number. That really does take decades. Do you think I'm wrong there? I don't know. I spent a lot of time with these companies who go zero to 20 in six months now. I've been shocked. I was shocked at how fast these companies are growing. And there's a lot of them. And some of them are going to flame out. And some are going to get disrupted by the model companies. But some aren't. Some of them are pretty legit and selling to non-tech companies and building real businesses. So if I look back, assuming we're in a bubble today, I look back to the bubble in '99 that I lived through 100 years ago. It was a little bit of the same many of the things that's different is the startups back then. They were only selling to each other. And when the house of cards fell, it kind of fell on everybody. And they really have much growth and much revenue. It's, that's what different about today. Like, and I think the difference is the products are different. Like you think about SaaS or you think about mobile. Like SaaS kind of started in the like, you know, Salesforce start in 2009, HubSpot, you know, whatever to, you know, for in a 10 year period a whole bunch of companies was started, not much happened after that 10 year period. And not much came out that was like, oh my God, that is amazing. The customers were blown away that they could grow that fast. The platforms were sort of set. Same thing with mobile. It all happened within like a couple of years. I kind of think the same with AI. I think most of the big AI companies were already founded. And it's going to settle in relatively quickly in the next year or two. And I think I think there'll be different too, is like, are the last one Amazon came out, Google came out, eBay came out, Salesforce came out. There were like four legit lasting great companies that came out, I think there'll be a lot more this time. This bum will pop, but I think a lot more companies will come out the other side. - Sequoia is the best of the best. You guys see everything, and you see the best companies. What are the trends that you're seeing right now amongst the companies that are rocket ships, but also you thinking they're going to be durable? Are there any trends that you're noticing amongst the entrepreneurs that sets them apart versus previous generations? - Okay, I came up with like a rubric first. So I see a lot of pit, so many pitches. And I'm trying to, what's my unfair advantage? And my unfair advantage is like, I spend a lot of time with CEOs, thinking about CEOs, seeing about the job, and I've done that. So I thought about like, what is like a rubric I can come up with, and I came up with a thing I call flock. F is is that when the fatter pitches, you get the sense they're first principled in thinking or they're just derivative in thinking. L are they lovable? Like in the question I ask myself is, if I were 27 graduating from Sloan, would I walk over broken glass to work for this CEO? Which I think is pretty good question. Were you lovable? I don't know, you tell me you work for me. When I talk to people who used to work for you, they describe you, I think it's material. Where they're like, you could be like really happy, but I only know you as a nice, like we only have cordial relationship. They would say when he was angry, he would get really, really angry. Very true, I was up and down, and it reflected my mood. My mood was up and down, and I had a hard time kind of hiding it. And I had great passion. That passion really showed up in an aggressive way. And I was definitely like, Darmesh was the teddy bear. I was sort of the bad cop a little bit. Like I was definitely tougher than Darmesh. And I think that Yinyang kind of worked for us. But lovable's won. And by the way, these criteria, I don't match 100% to all of them. Oh, is obsessed. Like I like founders who have been thinking about the damn problem for a long time. And then they finally start the company, and they are just obsessive compulsive. And I like to see a founder that was obsessed with something earlier in their life. Maybe it was, they're the world's best, you know, northeast New England, you know, ping-pong player, whatever it would be, something where they had to go very, very deep down a rabbit hole and get very good at something. I think that's good quality. I like the chip on the shoulder. I had a bit of a chip on my shoulder. I think Darmesh did too. And I like founders who have a chip. Like if it's a NEPO baby, I'm kind of skeptical whether they're gonna stick through the ups and downs. And then are they deeply knowledgeable? Do they have, you know, founder market fit? Do they know everything about this industry or are they kind of a tourist in the industry? So I call it flock. And if you have all of those money, talent, partners, customers will kind of flock to you. And nobody's a 10 out of 10 on all of them, but that's kind of my rubric I use. - Today's episode is brought to you by HubSpot. Did you know that most businesses only use 20% of their data? That's like reading a book, but then tearing out four-fifths of the pages. Point is you miss a lot. And unless you're using HubSpot, the customer platform that gives you access to the data you need to grow your business, the insights that are trapped in emails, call logs, transcripts, all that unstructured data makes all the difference. Because when you know more, you grow more. And so if you wanna read the whole book, instead of just reading part of it, visit HubSpot.com. - If you were young and getting after it at a new company, you're this 26-year-old kid with flock, what interests you right now, based off everything you're seeing? - One of the things I'm seeing in Sequoia is like the hardware companies are kind of set, the model companies are kind of set, all that infrastructure layer set. The app level is really starting, is now starting to really fly. Cursters, the really obvious one, but like Harvey and legal, rogo for investment banking. Like every kind of job now has an app company that is doing pretty well. And so I think that's the area I would be interested in. I'm a kind of an app guy. I don't really like infrastructure software that much. It's that exciting. But I like software that people use and can change their lives, improve organizations. I think that's where I would live. I like this company, rogo, which is like, think Chatchee BT, but for an investment banker. It is doing very well. I like Harvey, which is like lawyers. I like profound, which is, it's AEO, like instead of SEO, how do you get found in these search engines? I like Delphi. I built a clone on Delphi. And I think people are gonna have clones more and more clones. Like what I really want as a consumer, it's not here yet, and I'm waiting for it, is like I built this clone. People can talk to my clone all they want. It's pretty good. It's getting better every day. I want to train that clone, not just on what's out there in the internet with me, but train it on my email and my Slack and like all my calls. And I wanted to train a really know a lot about me. And instead of sending a listener to a meeting, I send my clone to a meeting that listens. And you know, for six months it just listens. But then people can start to ask my clone a question. Hey Brian, what do you think about this? And Brian will answer. And then eventually it's just like, I don't need to go to that meeting. I'm gonna send my clone to that meeting. And you know, I have a lot of meetings every week. I don't really have time for more meetings. It's just like send the clone out. I think that's the future of office work. And for some reason I don't see anyone really doing that. I want the opposite of that. I don't want a clone of me. I want the better version of me to do all the work. Or like, you know, I don't want another mediocre of me. I want the best version of me to be answering all the emails. I ask my clone questions. And it answers them much better than I would. 'Cause it's sitting on top of Chattu BT. It's sitting on top of all kinds of knowledge. It's very, very smart already. And as the models underneath get much better and as more content goes in there, it's gonna be very, very smart. Of course you're still gonna have your copial. Like I think of Chattu BT and now I use Gemini mostly. As like even better co-worker than a lot of my co-workers. So you definitely have that. But I think knowledge work is going to change. And I think my vision of the future, I don't know if it's five years out, I think something like that happens. Can you tell me how you're using Gemini right now on a daily basis? The way the thing is I've been using Chattu BT for so long, it really knows me. It knows everything about me, all my health stuff, like all the projects I'm working on, like everything. So it's tricky for me because I trained it so much, but man Gemini is so much better than I'm starting to use Gemini, kind of irritating, that I'm gonna have to train it on myself. But the thing I use that I really like are the project's functionality. So for example, on my pod, I have all these different guests. And you know, I have the CEO of Goldman Sachs coming on, like give me a bio of the CEO of Goldman Sachs. Listen to all my podcasts have done already. Create me a list of 20 good questions or topics to ask him. And then kind of go back and forth on it. I do that for every pod is super, super, super useful use case. I went to function health and I got all my blood work. I got up sole, they took gallons of blood out of me, but I know everything about it. Uploaded all that, collaborated on that, stuff like that. It's incredibly valuable. These days, I just, I think you know, I just came out of the new book by marketing lesson. And then we created a very, very cool set of videos around it that are AI generated. They're super, super cool that I like a lot. So I've been busy with it. And it's given me a massive productivity boost. I feel like there's two of me already. I find it to be very helpful as like a daily coach in a therapist of like, how should I react or how should it? Why do I feel this way about this particular situation? But when it comes to creative stuff, I find it to be a helper. But it's not even close to being hands off. But think about it, like two years ago, it was 50%. And the year ago, it was 65. And now it's 80, like keep drawing that curve. Like two years from now, it's going to be really much, much better than it is today. Yeah, and it makes me think that I'm not going to be investing in an entrepreneur anymore. I'm going to be investing in a machine that can just do all this stuff. Like I do think, I think Sam Alman said, he's like, if OpenAI isn't the first company that has an AI as the CEO, then I'll be pretty upset. And I do think that that's sort of going to happen. I think that the halves and the halves and nots have knots in terms of money is going to like separate further. And I asked Darmash when he came on because Darmash is heavily involved with, or he's an investor of OpenAI and is deep on this stuff. I was like, how is this going to turn out? And he was like, it's probably not going to be as good or bad as you think. And I was like, OK, that makes me feel better. But I don't know if I believe his assessment yet, even though he's probably the person I know best to, has the best judgment on this topic. I kind of think the way it plays out is people who are very high agency motivated. It unleashes their creativity and potential. People who aren't might be unemployed. Are you happy that you've made it already? No, I think if I were 26 at an entrepreneur, I'd make it again. Yeah, this isn't very good time to be an entrepreneur and like an outstanding, it's like never been a better time. Never been a better time. The history of homo sapiens to start a company might be. Yeah, I think I agreed. Dude, some of these young kids though seem crazy. Like, I don't remember. When I was in San Francisco back in 12, it was a much calmer environment than what it seems like now. Do you think that's an accurate assessment? Yes, everyone's here as I'm fire. I think that's going to make a lot of unhappy people. I think it's a bubble and every time this bubble, like tourists entrepreneurs come in, they're all coming into San Francisco which kind of bums me up and it kind of makes sense because Google's there and open their eyes here and they have a drop back in their breakdown town but man are people moving in. And there's a lot of tourists in there. Similar to happened in 2001, similar to what happened in the late 90s. And I think it's peak bubble. I don't know why it pops at some point. A lot of those tourists just get washed out. So my advice to entrepreneurs is like, if it's a bubble, what should you do? I'm not sure maximize evaluations where I call them but let's say you want to do that because you like the headline. I almost every entrepreneur, even starting a series A is taking money off the table. They're selling some of their own shares which is way earlier than he's dappin' and selling a lot. What's the definition of a lot? You know what, typical, if a series B company is ripping they're taking off five, 10 million bucks and then I would just raise more. Like you look at 2001, lots of good companies raise and then it crashed in like not many companies and they made it out of that valley of debt. I think you should raise a lot so you can kind of make it through like, yeah, I was gonna go like this and then go down and keep going. Another profile of entrepreneur I see a lot of. Yeah. Then I hadn't seen before. I call them like a five tool CEO where they can code, they have tastes, they can sell, they can fundraise, they can recruit. They're like a kind of perfect entrepreneur. So like Brett Taylor is one of those, and there's a bunch of them out there. The rogo CEO, I just mentioned the Delphi CEO. That's kind of a new breed we never saw. Like before you saw a lot of darmesh in me. Like the extrovert, me introvert, like the Yang and the Yang. Now you're seeing I see a lot more of these like superheroes showing you. I don't understand, like I've met some of these guys and this guy Brett Taylor in particular, I don't know him but I would love to have him on. Like when I hear something like him talk, I just think how on earth can one person be so smart and so good at so many different things? - I totally agree, I totally agree with you. - Whatever I see Shaq and like a 5/10 or a 5/4 lady, I'm like how are these both humans? - Yeah, that's what I feel about what I see. What I hear Brett Taylor talking to me. I'm like how are we like made up and mostly the same stuff? - Yeah and there's a bunch of the early CTOs are like that. They're charismatic, they can sell, they can recruit, they can pitch, man they can code and they have tastes like it's an impressive new breed that's showing up. - I just got done reading this like sales book on how to run a sales team and the intro was talking about how it was your HubSpots first, first head of sales, Mark. Yeah and then I read another one and it was like I was HubSpots first, SEO person and there's like four more like that. And it seems like your first 50 employees are now like pretty big ballers doing their own thing or our experts and people look up to them. What do you think made you so good at recruiting? And how did you do it? - I think in the early, we were very first principled so we were like marketing is totally broken. Outbound's dead, no one's listening to any of these ads or any of these cool calls or any emails. You have to do inbound. And so we had a contrarian to you. Most people that were wrong but enough people that were right. And we had a mission. The mission was to apply that idea to helping small businesses grow. And lots of people grew up in a small business family and wanted help small businesses to grow. It's a mission you can kind of get behind helping millions of small businesses grow better. I think that helped. Early we just sucked out of MIT. Like we were two Sloanies that started the companies. So like our first 10 employees, Ada the first 10 were classmates of ours. We sucked over that help. Mark Rebares was our TA actually the guy who wrote a book you were talking about. And then we worked on culture. We had a unique culture. We thought of our product as like you got to make a unique product relative to the competition. You got to make a quality product. If you do that, it pulls customers in. Our culture is like you need to make a unique culture and you need to make a high quality culture. And if you do that, you pull and retain employees. So we were kind of first principles along a few different lenses. We also kind of zaked with the world was zagging. The world said you got to go to enterprise. That's where all the money is. And we're going to do SMB. And we're going to rethink this. We're going to make the model work in SMB even though everyone thinks we're wrong. And then we said we're going to go after Salesforce.com. When Salesforce.com was like unassailable. Everyone was like, I get crazy. You'll never beat them. Shh. We weren't after them. So there's a bunch of points and upspot histories where we kind of zaked when everyone else, you know, peer teal is aligned. Like you need to be right about something that a lot of people disagree with. You need to be right about something that everyone thinks you're wrong about. And we had a couple of those. Not a lot, but we had a couple of important ones. Did you almost cave at the consensus? No, we had a real conviction on the SMB thing. It cost us. Like we would raise, we would go raise our rounds. I was walking out of Sanjaro. We had all those. Like we had, we never had, the only easy round was the IPO round. Nobody liked the thesis. Nobody bought the SMB thesis. No one else had done it other than into it. And we were convicted of it. I think part of the reason we were convicted is both of us had spent our whole lives previously selling to enterprise CIOs. And it's kind of soul crushing work, selling to enterprise CIOs. And it was like, let's do something a little bit more fulfilling. Something they can get us energized in the morning helping these small businesses grow better. The Salesforce thing, we got a lot of push back on that. But we didn't feel like we had a choice. You know, Salesforce was our really good ally. And our pitch was, you know, Salesforce.com was SFA for sales and hubbots was for marketing for a long time at work. And then Salesforce.com one day woke up and says, we want to be the Salesforce.com marketing. And so we were like, either we need to pivot and kind of come after them or eventually just going to get crushed and pushed out and sold private equity. I'm trying to become a better CEO. And I know that you guide a lot of CEOs at Sequoia, what did you do at HubSpot that you think, as a CEO, that you think was wrong and you advise people to avoid or attributes to change of themselves? - One of the things that I think really worked that's actually underrated is Paul Graham's founder mode article. And I remember reading that article in thinking that was what I did early. Those were my instincts. And I kind of got tossed out of it over time. And the guy who I think has it right is like, you know, back in my day it was Jack Welch and I was just as long. And Jensen does this, got 60 direct reports. He's tough like I was and he gives public and private feedback. Now he doesn't give private feedback, all the feedback positive negatives. And then he doesn't do what I was. And like I did all of that early in HubSpot and sort of got talked out of them like no, no, no, Brian. Matur CEO does a one-on-one with each manager every week. No, no, no, Brian, you need a staff meeting with just your direct reports. You should only have nine direct reports. No, no, Brian, you should praise publicly and criticize privately. So as time went on, I got worn down on that stuff. And then I watched what Jensen's doing today and I read the founder mode stuff and like I should have stuck with my convictions on some of that stuff. I regret kind of, I kind of managed, I got more manager Modi as time went on. I forgot that. Of the manager mode stuff, what do you think actually it works? I mean, we did, we got our shit together on planning. Like we were very shoot from the hip for many, many years. And we got a really good planning process down, which is very manager Modi. We did bring in some execs from the outside that were very, very good and really upleveled us. We probably did too much of that. And I think a mistake a lot of founders made is they go and hire that whatever CMO from Microsoft, whatever. And they're really proud of it. They do a press release. And we're excited. We have this amazing CMO, but the CMO gets in the company. They're like, where's my secretary? Where's my coffee? Where's the reports? Where's all my stuff? And Bip Waston C in this startup. And they're miserable. And their colleagues are miserable. So I see that as a big failure condition, particularly hire people from much, much bigger companies. I think people underestimate how good their homegrown talent is. And it's like the Red Sox. Like I'm a big Red Sox guy. The Red Sox dramatically overvalue players and other teams relative to their own talent. And I think every baseball and sports team does this and every CEO does this. So there's this-- I intimately and deeply remember this one phase when we were selling to you guys. Basically, my company was only like 30 people. So it was basically just me doing the deal. And I didn't have an HR team or anything like that. And HubSpot had five or six employees, of which one of them is now on the board of Asana. So these big shots. And then you guys have seven or eight lawyers who are probably making two grand an hour. And then you had seven or eight KPMG accountants. And they were asking me all these questions. And they asked two questions that it was laughable. The first question, they were asking for invoices or no, what were they asking for? They were asking if they're like, what's this $50 charge? And I was like, I had some guy on Fiverr do like a logo or something. And they're like, did he sign an NDA? I'm like, dude, his name was like big baller boy 69 on Fiverr. Like, I didn't get him. I'm sorry, I just-- I don't know. And then the second thing, they were like, what's your like five-year plan? Like, do you have like projections? I'm like, do you guys? My company's like four years old, you know? Like the projections, like we do quarterly by quarterly, but like shit changes. And they were pretty cool where they were like, OK, we understand. You know, they were treating this like $30 million deal. Like it was a $3 billion deal, which is understandable. It was a weird deal though. Like, we bought a content company. It was kind of a weird acquisition we did. And I think when it came up, everyone was like, what are we doing here? And they were trying to like, you know, make sure that they are doing their diligence and stuff. But I remember thinking like, I don't plan that far out. I'm so sorry. Like, I don't even know what the company's going to exist in two years, let alone like what the financials are going to be. And that was like pretty funny. And it rattled-- because the people I was talking to were just hires. Like, they had never like, found it a company. And like, I remember it kind of rattled them that I didn't plan. And I was like, how do you guys not understand that? And there was this huge distinction between me just being still entrepreneur mode and then being in like, I'm only used to this little bit more corporate setting. And I thought that was funny. I think people get too corporate too early. I think startups have nothing to lose, nothing. This is literally no assets, no revenue, nothing to lose. And as they get bigger, they have more to lose. And the lawyers get more involved because they want to, you know, cross the T's and dot the S. I think startups, they grow up too fast. The lawyers get too much power too fast. And I think people think, OK, we hit a billion in market cap. We have a lot to lose, right? I think the mice should be like, how do we get to $100 billion? And how do we continue that risk-seeking appetite? The other thing that gets messed up in these scale-ups, most companies break at 150, 150 employees. And that's Dunbar's number in all kinds of shit goes wrong in there. The director layer shows up. So there's like one more layer between the CEO and the customer. And I kind of messed this stuff up. The people joining are a little more mercenary and a little less missionary, who changes things quite a bit. Your whole value prop, you're giving to an employee, you're attracting someone who's sort of risk-in-first at 150 versus 15, someone who's really risk-seeking. And that just bleeds into the whole company. And the certain points is like, only the founders are the people who are risk-seeking. And that protect what we have versus go get something new is interesting. And what's happening in Silicon Valley that I think's interesting is the CEO of Rippling's doing this very aggressively. More and more CEOs are hiring failed founders or doing very cheap aquahires and kind of seeing their whole company with founders. Rippling's got over 100 ex-founders on their team. And I think that's good, that keeps you focused on the long haul and risk-seeking. You gotta keep the risk-seeking up for a low-mo period of time. (upbeat music) This is for the folks out there who have a business that does at least $3 million a year in revenue. Because around this point, that's when you're able to look up after being heads down for years building your company and you realize two things. One, you've done something great, but you're still a long way from your final destination. And two, you look around and you realize, I am all alone, I've outrun my peers, which means you're now making $10 million decisions alone by yourself. And that is when mediocrity can creep in. My company, Hampton, we solved this problem by giving you a room of vetted peers, of other entrepreneurs who are gonna hold you accountable, call you out on your nonsense and help show you the way. Because the fact is, is that there's only a tiny number of people in your town who know what you're going through and who have been there. And they're hard to find. The biggest risk is not failing. You have a company and it's working, you're gonna be fine. But the biggest risk is waking up 10 years from now and saying, shit, I barely grew in business and in life. And for people like you who are ambitious, wasted potential and regret is what we want to help you to avoid. We have made so many of these groups and we have a thousand plus members. And I know this stuff actually works. It can change your life, it changed mine, and I know it will change yours. So check it out, joinhampton.com. You're so fascinating to me, because you've one of the very few people on Earth who's built a company to be worth tens of billions of dollars. And yet, you're this grateful, dead, love, and hippie. And you're telling people, don't grow up too fast. Don't be too corporate. But you're an onion man, there's layers. That's why I think you're fascinating. Let's talk about, let's talk about Jerry Garcia for a second. He's like not the first, but what are the first in the very classic Silicon Valley entrepreneur? Do you know where the company was founded? Yeah, well, in the house across the street from Ben and Jerry's and had hate ashberry, right? Was that what he was like? It was founded in Palo Alto. Oh, interesting. It'd like rate down the street from Stanford. And the first concert was in a pizza place, rate in Palo Alto. And so it's like a, he's a classic Silicon Valley founder. Like, first principles. Completely first principle, everything. He didn't care what anyone thought. He was like, this is the way we're going to go. Right way did he say to go. For example, at the time, rock 'n' roll was new. And there were lots of rock 'n' roll bands at the time. And there were jazz bands, there were country bands. When he built his team, the team was very spiky, very good Silicon Valley spiky. And his bass player was actually an avant-garde trumpet player that learned the bass. His keyboard player was actually a blues harmonica guy. That was the blues DJ in town. His main singer was a country cruder. And his drummer was like a drum major at. So he brought together this very spiky team. And instead of creating rock 'n' roll, he created a whole new genre called jam band. And now fish and so many other bands copy them. And so hops back to the same thing. Yeah, we said this outbound thing is dead. We're going to create this genre called inbound marketing. So very first principle the way he thought. The other thing he did that was super clever beyond the music was his marketing. So if you go to go to a Rolling Stones concert, let's say in 1980, he bring in all your equipment to the concert, big camera, your microphone, whatever, and you go to walk in the concert. You get out of here with all your equipment. This is our IP. This is Rolling Stones on us to get out. A grateful dead. If an idiot liked me, he showed up with his camera and all his recording and quizz boom mic. Brian, come on in. So right here up in the front, we've got a taper section for you. And so people like me would go to Boston, charge for New York, Philly, DC, and record all the concerts. We could back home, we had the tape to tape thing. And the best concert would make 50 copies of. And then we traded, we weren't allowed to sell the tapes. That was part of the cause where you trade the best tapes with all your friends so you pick up their best stuff and my best stuff. I told you, I used to share an office with nugs.net, the marketplace where they would trade the tapes. Right. And then you'd be at like a party on campus and somebody put your bootleg on. And the person next to you would be like, "Why everyone's dancing is crazy chips." And what is this weird gypsy music? You know, it's a grateful dead. They're coming down town, come on tour with us. And so grateful they were the first Silicon Valley viral inbound marketers. So he was very first principle about his music and his market. There's a lot more stuff about his marketing and I think it's very interesting. I mean, I've been, my parents were dead heads and they traveled with them, like, you know, show to show. I'm just Google them while you're talking. You said you're 58. Yeah, I was, I'm a very young dead head. Dude, this guy looks like 30 years older than you but he died when he was only 52 or 53. Oh, of course, yeah, yeah. He was, he did not say, he's not like the Silicon Valley people like Brian Johnson, Peter Andrew Huberman fan. He is his major food grids for 20 Swinkies and Swinkies. Yeah, he looks like he parties. What's the name of the book called marketing lessons from the grateful dead? Buy it and triplicate it. You got to buy that for your parents. Did you get to meet them when you're writing it? I met Bob Weir, yes. And we told Bob Weir, like, here's what we're doing. He's like, huh. I was wondering if anyone would ever write about that. That's pretty cool. He was like, huh. That was his reaction was like, huh. If you Google, I think if you Google your name in "Greyfoot Dead," like one of the first things that comes up is that you bought, you know, his guitar at an auction. Yep. I have a jerry grime. I have considered myself the steward of his guitar. He's a very unique guitar. He played it all through the '70s and yeah, I own it. And I let it out. Like John Mayer played it. Like, everybody and their brothers. Anyone who wants to borrow it can borrow it. But yeah, I enjoy being the steward of a little piece of Jerry Garcia. I love talking to you because I just think that like, I think that like the world needs more people who have this perfect balance of being like a shark and hard hitting, but also like polite and kind. I think there's like a, there's like kind of rare. And I aspire to be like that. And I think that when I think of like all the people who I, you know, admire, it's kind of like me and Brian Halligan's kind of like, where I want to go, but in a handful of years. So I, I love talking to you. I hope we can do it in person next time. Appreciate you, my friend. I want to be like you when I grow up. All right, God bless. Thank you. All right, everyone, if you're listening to MFM, you probably want to make more money. Well, I want to tell you about a podcast you might want to check out. It's called The Sales Evangelist and it's hosted by Donald Kelly. Each week, Donald interviews the world's best sales experts who share their strategies to succeed in sales. They share actionable insights and stories that will encourage, challenge, and motivate you to hustle your way to the top. If you're someone looking to raise your income level, check out The Sales Evangelist. You can find it wherever you get your podcasts.