Should You Start a Company? The Honest Truth

We were constantly like, Salesforce is going to crush us tomorrow. Did you see their announcement? We're dead. We said that so many times. I'm excited to be on your show.

It's kind of our show, Brian.

Yeah, that's true.

Do 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? Because you've founded a company that is now has, I don't know, 5, 6, 7,000 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, a VC and advisor. So tell me about your happiness levels between each one?

Okay. I'm going to give you like the grading system in my head for number of employees. Zero, like 2 to 10 employees. I was like a C. I didn't really, I could write code, but no one wanted it. Like I did, 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 1,000, you know, maybe A minus. Like I kind of felt like I knew what I was doing. 1,000 to 10,000. I didn't enjoy the— the secret of life is 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, in the history of HubSpot. Like I, I had sort of CEO market fit between 10 and 1,000.

That's like you're, you're, you're putting 100 to 1,000 in 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 work— 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 $3 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 that 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 worry in that phase about what the nom 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, are the employees productive and happy? Are the customers productive and happy? Like really focused on that. And I like that type of work.

Can you go through? Okay. So your categories were 2 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 talk about 996. That was at least that for both Dharmesh and I, we were, 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, you're full on. Like the 996 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 got, 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.

I'm angry most of the time. 10% of the time it's like, we got this, we got it. Everything's going our way. The winds are at our back, but it's pretty rare. And like you live your day looking at your Slack and your inbox and your texts and it's mostly bad news in there.

Well, so tell me once a company gets to a hundred, or 1,000 employees or 10,000 employees, does that emotion go away?

Same. It's the same ratio. It's still mostly a shit sandwich in your inbox.

Do 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 constantly.

We were constantly like, Salesforce is going to crush us tomorrow. Did you see their announcement?

We're dead.

We've said that so many times. Yeah, we tend to overestimate what our 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. Uh, you have to prove them wrong. You are horrible. You barely growed. You can't do this. You have to, like, and it wears people out though, because I actually think that that's negative. That's a pretty poor way to motivate people. Uh, but it motivates me.

I'm the same. And 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 imposter syndrome. I'm a little nervous talking to you today. Believe it or not.

Really?

Why? Yeah, I'm not— given all the success I've had, my confidence doesn't even remotely compare to it. And my inner monologue is like, you got so much to prove, dude. Don't fuck it up.

Does Dharmesh 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, 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 imposter syndrome? And they hem and they hem and ha, because they don't want to say they do. They do. Almost all of them.

Let me ask you one more question about all this, and then I want to know about, uh, what you're like, more of the Sequoia stuff, because I think that's super fascinating. Sometimes I think that with being an entrepreneur, the hard part, I've been thinking 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 6 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 a lot of fun. I mean, there was just a lot of joy and the people at HubSpot are amazing. The customers are amazing, partners are amazing. So many, so many happy times, a lot of down days, but like the up days definitely outweigh it. I'm super proud of what we built. I'm, you know, yeah, I, I, I wouldn't trade it. The thing I would say about HubSpot that it's, it's a little bit of what you said, but it's, I think of it as like HubSpot was like two steps forward, one step back, two steps forward, one step back. It, it looks like, oh, if you look at the graphs, like, ooh, that was, that was an easy ride. 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 going to get through it. We're going to rally the troops. We're going to figure out, we're going to learn from that mistake and go forward. Almost all the step backs 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 ChatGPT 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 with in 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 ChatGPT ask 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, enter 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 to 20 times a day.

Um, 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 pothole report. And we live in Boston, and this, like, this time of year is potholes everywhere. And that was the analogy we used at HubSpot. Like, we would create these potholes, and sometimes you kind of bounce through the pothole and it would hurt a little bit. Sometimes a pothole 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 pothole. So the pothole report was every time we had a pothole, we'd look back and like, how, how should we have handled this a year ago so that wouldn't have happened? Or what data do we wish we have? And I'll give you an example of it. We had a pothole in like 2011. One of the things we did at HubSpot is we hired really good support people and our secret sauce in 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 in Cambridge anymore because we hired so many people. And so, and the value prop was great. It's like, you make a little bit more money, but how'd you 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 CSMs, into sales, into products. So we fed the whole company really with these Apple Store people. People that were terrific. And in this 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 prided ourselves on like answering the call within 30 seconds and then staying on as long as they wanted. And you know, our wait time went to like 20 minutes and customers are like, what the hell is going on? That was a very solvable, predictable problem that, you know, if you had, if you just looked at this one chart, we won't make that mistake again. 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, you know, people break, processes break, systems break, like everything's just breaking, breaking, breaking with scale.

What I've noticed, particularly talking to people on MFM, is that it really takes like 8 or 9 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 in revenue by year 6, 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 refer to a second mountain business as something that's beyond just making your initial, like, financial security uh, uh, number that really does take decades. Do you think I'm wrong there?

I don't know. I, I spent a lot of time in these companies that go zero to 20 in 6 months. Now I've been shocked, shocked at how fast these companies are growing. Uh, 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 like, some of them are like pretty legit. Selling to non-tech companies and building real businesses. So like, if I look back, like assuming we're in a bubble today, I look back at the bubble in '99 that I lived through 100 years ago. It was a little bit of the same mania. The thing that's different is the startups back then, they were only selling to each other. And when the kind of house of cards fell, it kind of fell on everybody. And they really have much growth and much revenue. It's it, that's what's 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 started in 2009, HubSpot, you know, whatever, you know, for in a 10-year period, a whole bunch of companies were 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 years. I kind of think the same with AI. I think most of the big AI companies are already founded and it's going to settle in relatively quickly in the next year or two. And I, the thing I think it'll be different too is like out of the last one, Amazon came out, Google came out, eBay came out, Salesforce came out. There were like 4 legit lasting great companies that came out. I think there'll be a lot more this time. This, this bubble will pop. But I think a lot more companies will come out the other side.

Sequoia is the best of the best. Uh, 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 for, so I see a lot of pitch, so many pitches and I'm trying to figure out what's my unfair advantage. And my unfair advantage is like, I spend a lot of time with CEOs thinking about CEOs, thinking about the job. And I've been, 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, is that when the founder pitches, you get the sense they're first principled in thinking or they're just derivative in thinking. L is, are they lovable? Like, and 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 a pretty good question.

Were you lovable?

I don't know, you tell me, you worked for me.

When I talk to people who used to work for you, they described you, I think, as mercurial, where they were like, you could be, um, like really happy, but I, but I only know you as a nice, like a we only have cordial relation, a very 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. Um, and I had, I had great passion. That passion really showed up in an aggressive way. Uh, and I was definitely like Dharmesh was the teddy bear. I was sort of the bad cop a little bit. Like I was definitely tougher than Dharmesh. And I think that yin and yang kind of worked for us. Um, but lovable is one. And by the way, these, these criteria, I don't match 100% all of them. O 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 Dharmesh did too. Um, and I like founders who have a chip, like if it's an EPO baby, I'm kind of skeptical whether they're going to stick through the ups and downs. And then are they deeply knowledgeable? Do they have, 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.

If you were, uh, young and getting after it at a new company, you're 20, you're this 26-year-old, uh, kid with Flock, what, what interests you right now based off everything you're seeing?

I, I, one of the things I'm seeing in Sequoia is like, you know, the hardware companies are kind of set, the model companies are kind of set, all that infrastructure layer set. At the app level is really starting, is now starting to really fly. You know, Cursor's the really obvious one, but like Harvey and Legal, Rogo for investment banking. Like every kind of job now has an app company that's 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. I don't find 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 ChatGPT, but for an investment banker, and it's 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 going to have clones, more and more clones. Like what I really want as a, as a consumer, it's not here yet. And I, I'm waiting for it. It's 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 that, I want to train that clone not just on what's out there on the internet with me, but train it on my email and my Slack and like all my calls. And I want them to train and 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, the first 6 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 going to 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. Um, 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, uh, the better version of me to do all the work or like, you know, I don't want another mediocre me. I want, uh, the best version of me to be, to be answering all the emails.

I ask my clone questions. And it answers them much better than I would, because it's sitting on top of ChatGPT. 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 going to be very, very smart. Um, of course you're still going to have your copilot. Like I think of ChatGPT, and now I use Gemini mostly, as like an even better coworker than a lot of my coworkers. 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 5 years out, I think something like that happens.

Can you tell me how you're using Gemini right now on a daily basis?

The weird thing is I've been using ChatGPT 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. And 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 going to have to train it on myself. But the thing I use that I really like are the projects 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 I've 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. It's a super, super, super useful use case. I went to Function Health and I got all my blood work. I got upsold. Like, I like, they took like gallons of blood out of me, but I know everything about it. Uploaded all that, collaborated on that, um, stuff like that. It's incredibly valuable. These days, I just, I just, I think, you know, I just came out with a new book, My Marketing Lesson from the Grateful Dead. We created a very, very cool, uh, set of videos around it that are AI-generated. They're super, super cool, uh, 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, like a daily coach and a therapist of like, how should I react? Or how should I, why do I feel this way about this particular, particular situation? But when it comes to creative stuff, I find it to be a helper, but it's, it's not even close to being hands-off.

But think about it, like, 2 years ago it was 50%, and a year ago it was 65%, and now it's 80%. Like, keep drawing that curve. Like, 2 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 Altman said he's like, if OpenAI isn't the first company that has an AI as the CEO, then I'd be pretty upset. And I do think that that's sort of going to happen. I think that the haves and the have-nots, have-nots in terms of money, is going to like separate further. And I asked Dharmesh when he came on, because Dharmesh, you know, 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. Uh, and I was like, okay, that makes me feel better, but I don't know if I, I don't know if I believe his assessment yet, even though he's probably the person I know best who 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 and an entrepreneur, I'd Make it again. Yeah, this is a very good time to be an entrepreneur and like an outstanding, it's like never been a better time, never been a better time in the history of, of Homo sapiens to start a company in my opinion.

Yeah, I think I agree, dude. Some of these young kids though seem crazy. Like I don't remember when I was in San Francisco back in, um, 12, it was, it was a much calmer environment than what it seems like now. Do you think that's an accurate assessment? Yes.

Everyone's hair is on fire.

I think that's going to make a lot of unhappy people.

I think it's, I think it's a bubble. And every time there's a bubble, like, tourist entrepreneurs come in. They're all coming into San Francisco, which kind of bums me out. And it kind of makes sense because Google's there and OpenAI's here and they have PropTech and they're right downtown. But man, are people moving in. And there's a lot of tourists in there. Similar happened in 2001. Similar is what happened in the late '90s. And I think it's peak bubble. I don't know when it pops. It pops at some point. A lot of those tourists just get washed out. So my advice to entrepreneurs is like, if it's It's a bubble.

What you sh—

what should you do? I'm not sure maximizing valuation is the right call, but let's say you want to do that because you like the headline. I almost every entrepreneur, even starting Series A, is taking money off the table. They're selling some of their own shares, which is way earlier than it used to happen and selling a lot.

What's the definition of a lot?

You know, a typical, if it's Series B company is ripping, they're taking off $5, $10 million. And then I would just raise more. Like you look at 2001, lots of good companies raised and then it crashed and like not many companies made it out that valley of death, I think you should raise a lot so you can kind of make it through. Like, AI is going to go like this and then go down and keep going. Another profile of entrepreneur I see a lot of, yeah, that I hadn't seen before, I call them like a 5-tool CEO, where they think code, they have taste, they can sell, they can fundraise, they can recruit. They're like the kind of perfect entrepreneur. So like Brett Taylor is one of those. Um, there's a bunch of them out there. Um, 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 Dharmesh and me, um, like the extrovert and the introvert, like the yin and the yang. Now you're seeing, I see a lot more of these like superheroes showing up.

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, when I hear someone 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 like, whenever I see Shaq and like, you know, like a 5'10" lady or a 5'4" lady, I'm like, how are these—

how are these both humans?

Yeah, that's what I feel about what I see when I hear Brett Taylor talking to me. I'm like, how are we like made up of mostly the same stuff?

Yeah. And there's a bunch of the early stage CEOs are like that. They're charismatic. They can sell, they can recruit, they can pitch, but man, they can code and they have taste. 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— HubSpot's first, um, first head of sales, Mark. Uh, yeah. And then I read another one and it was like, I was HubSpot's first SEO person. And there's like 4 more like that. and it seems like your first 50 employees are now like pretty big ballers doing their own thing or are, uh, experts. Um, 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 cold calls or any emails. You have to do inbound. And so we had a contrarian view. Most people thought we were wrong, but enough people thought we 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 want to help small businesses grow. It's a mission you can kind of get behind, helping millions of small businesses grow better. I think that helped early. We, we just sucked out of MIT, like we were two Sloanies that started the company. So like our first 10 employees, 8 of the first 10 were classmates of ours we sucked over. Uh, that helped. Marc Roberge was our TA, actually, the guy who wrote that book you were talking about. And then we worked on culture. We had a unique culture. We thought of our, our product as like, you gotta make a unique product relative to competition. You gotta make a quality product. If you do that, it pulls customers in. Our culture, 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, you know, we were kind of first principles on a, along a few different lenses. We also kind of zigged when the world was zagging. The world said, you gotta go to enterprise. You know, that's where all the money is. We said, no, no, no, no, no, no. We're gonna do SMB and we're gonna rethink this. We're gonna make the model work in SMB, even though everyone thinks we're wrong. We, and then we said, we're gonna go after salesforce.com when salesforce.com was like unassailable. Everyone's like, oh, you're crazy. You'll never beat them. We went after them. So there's a bunch of points in HubSpot histories. Where we kind of zig when everyone else, you know, Peter Thiel has a line 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, we had a real conviction on the SMB thing. It cost us like we would, we would raise, we would go raise our rounds. We go up and down Sand Hill Road. We get all nos. Like we had, we never had, the only easier round was the IPO round. Um, nobody liked the thesis. Nobody bought the SMB thesis. No one else had done it other than Intuit. And we were, 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. It was like, let's do something a little bit more fulfilling, something that can get us energized in the morning, helping these small businesses grow better. The Salesforce thing, we got a lot of pushback 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 HubSpot was for marketing for a long time. That worked. 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 we're eventually just gonna get crushed and pushed out and sold to private equity.

I'm trying to become, um, a better CEO, and I know that you guide a lot of CEOs, um, 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, uh, 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 and thinking that was what I did early. Those were my instincts. And I kind of got talked out of a lot of it over time. And the guy who I think has it right is, is like, I, you know, back in my day it was Jack Welch, now it's Jesse Hwang. And Jensen does this, got 60 direct reports. He's tough like I was, and he gives public and private, um, feedback. He doesn't give private feedback, all the, all the feedback, positive, negatives, and, and, and then he doesn't do one-on-ones. And like, I did all of that early in HubSpot and sort of got talked out of them. Like, no, no, no, Brian, mature 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 9 direct reports. No, no, no, Brian, you should, 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. I'm like, I should have stuck with my convictions on some of that stuff. I regret kind of, I kind of, I got more manager modey as time went on. I regret that.

Of the manager mode stuff, what do you think actually works?

I mean, we did, we find, we got our, 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 modey. Uh, we did bring in some execs from the outside that were very, very good and really up-leveled us. Um, we probably did too much of that. And I think a mistake a lot of founders make is they go and hire that whatever CMO from Microsoft, whatever, and they're really proud of it. They do a press release and everyone's 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 reports? Where's all my stuff? And they're lost in see in this startup, and they're miserable, and their colleagues are miserable. So I see that as a big failure condition, particularly hiring 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 in 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, uh, I, I, I, I intimately and deeply remember this one phase when we were selling to you guys. Basically, it was, you know, my company was only like 30 people, so it was basically just me doing the deal. And I didn't have like an HR team or anything like that. And, and HubSpot had like 5 or 6 employees, of which one of them is now like on the board of Asana. So these big shots. And then you guys have like 7 or 8 like lawyers who are probably making $2,000 an hour. And then you had 7 or 8 KPMG accountants and they were asking me all these questions. And they asked 2 questions that I like, it was laughable. The first question, they were like asking for like invoices or no, what were they asking for? They were asking if I, um, 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 5-year plan? Like, do you have like projections? I'm like, you guys, my company's like 4 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, okay, we understand. Like, you know, they were treating this like, you know, 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's 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 were 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 if the company's going to exist in 2 years, let alone like what the financials are going to be. Uh, and that was like pretty funny. And it like, it rattled the, because the people I was talking to were just, uh, hires. Like they had never like founded a company and like. I remember it like kind of rattled them that I didn't plan. And I was like, how do you guys not understand that? And there was this like a huge distinction between me just being still in entrepreneur mode and them being in like, I'm only used to, um, 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. There's 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 I's. I think startups, they grow up too fast. The lawyers get too much power too fast. And I think people think, okay, we hit a billion in market cap. We have a lot to lose. Where I think the mindset should be like, how do we get to $100 billion? Um, and how do we, 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 Dunbar's number, and all kinds of shit goes wrong in there. Um, the director layer shows up, so there's like one more layer between the CEO and the customer that kind of messes stuff up. The people joining are a little more mercenary and a little less missionary, which changes things quite a bit. Your whole value prop you're giving to an employee you're attracting someone who's sort of risk-averse at 150 versus 15, someone who's really risk-seeking. And that just bleeds into the whole company. And at certain points, it's like only the founders are the people who are risk-seeking. And that, that protect what we have versus go get something new is interesting. And what is happening in Silicon Valley that I think is interesting is more— and the CEO of Rippling is doing this very aggressively— more and more CEOs are hiring you know, failed founders, like, or doing very cheap acquihires and kind of seeding their whole company with founders. Like, Rippling's got over 100 ex-founders on their team. And I think that's good. That keeps you, like, focused on the long haul and risk-seeking. You gotta keep the risk-seeking up for a long, long period of time.

You're so fascinating to me because you're 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-loving hippie, and you're telling people, don't grow up too fast, don't be too corporate. But, uh, you're, you're, you're, you're an onion, man. There's layers. That's why I think it's, I think you're fascinating.

Let's talk about, let's, let's talk about Jerry Garcia for a second. He's like the, not the first, but one of the first in the, in the very classic Silicon Valley entrepreneur. Do you know where the company was founded?

Uh, yeah, I, uh, well, in the, the house across the street from Ben Jerry's, uh, in Haight-Ashbury, right? Was that like?

It was founded in Palo Alto.

Oh, interesting.

It like right down the street from Stanford. And the first concert was in a pizza place right in Palo Alto. Um, and so it's like a cla— 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.

What way did he say to go?

For example, uh, uh, at the time rock and roll was new and there were lots of rock and roll bands at the time and there were jazz bands, there were country bands. When he built his team, his team was very spiky, very Silicon Valley spiky. And his, his bass player was actually an avant-garde trumpet player that learned the bass. Uh, his keyboard player was actually a blues harmonica guy. His dad was the blues DJ in town. His main singer was a country crooner and his drummer was like a drum majorette. So he brought together this very spiky team and instead of creating rock and roll, he created a whole new genre called jam band. And now Phish and so many other bands copy them. And so HubSpot did the same thing. Yeah, we said this outbound thing is dead. We're gonna 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, you bring in all your equipment to the concert, your big camera, your microphone, whatever, and you go to walk in the concert, get out of here with all your equipment. This is our IP. This is Rolling Stones on us. Get out. The Grateful Dead, if an idiot like me showed up with his camera and all his recording equipment, 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, Hartford, New York, Philly, D.C., and record all the concerts. We'd go back home, we had the tape-to-tape thing, and the best concert we'd make 50 copies of. And then we'd trade— we weren't allowed to sell the tapes, that wasn't part of the culture— where you trade the best tapes with all your friends. So you pick up, 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 a, you'd be at a, like a party on campus and somebody put your bootleg, you put your bootleg on and the person next to you would be like, why everyone's dancing this crazy gypsy, what is this weird gypsy music? Grateful Dead. They were coming, they were coming in town, come on tour with us. And so the Grateful Dead were the first Silicon Valley viral inbound marketers. So he was very first principle about his music and his marketing. There's a lot more stuff about his marketing that I think is very interesting.

He, uh, I mean, I've been to— my parents were Deadheads and they, uh, traveled with them like, you know, show to show. I'm, I'm, I'm just Googling while you're talking. How old? You said you're 58?

Yep. I was— I'm a very young Deadhead.

Dude, this guy looks, uh, like 30 years older than you, but he died when he was only 52 or 53.

Garcia, yeah. Yeah, he was— he did not take— he's not like the Silicon Valley people, like Brian Johnson, uh, Peter, uh, Andrew Huberman fan. He, he His major food groups were Twinkies, Twinkies, and Twinkies.

Yeah, he looks like he parties. What's the name of the book?

It's called Marketing Lessons from the Grateful Dead. Buy it in triplicate. You gotta buy that for your parents.

Did you get to meet them when you were writing it?

I met Bob Weir, yes. And we told, I 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 only, huh.

If you Google, I think if you Google your name and Grateful Dead, like one of the first things that comes up is that you bought, uh, you know, his guitar at an auction.

Yep. I have Jerry. I consider myself the steward of his guitar. It'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. Um, uh, but yeah, I, I, 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 that 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, you're— it's kind of like me and Brian Halligan is kind of like where I want to go, but in a handful of years. So 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.