We were constantly like sales forces going to crush us tomorrow. Did you steal her announcement? We're dead. Like I said, that's so many.
I feel like I can rule the world. I know I can be what I want to. I put my all in it like a day. I'm excited to be on your show.
It's kind of our show, Brian. That's 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 your levels of happiness been? Because you've founded a company that is now has 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. OK, I'm going to give you a grading system in my head for a number of employees. Two to 10 employees. I was like a C.
I didn't really add. I could write code but no one wanted it. You don't have a lot of value at that phase. 10 to 100, I was like, hey, I felt like I knew what I was doing.
I had been in scale ups before. 100 to 1,000, maybe A minus. I kind of felt like I knew what I was doing. 1,000 to 10,000.
I didn't enjoy the secret of life enjoying the passage 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. Like I had sort of CEO market fit between 10 and 1,000. That's like 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 I 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 billions in revenue. So I sort of saw that journey and I was part of that machine. And so 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 of 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 nom and go committee of the board thought. Very little interaction with our compliance and legal folks, things like that. Mostly just working on the employees productive and happy or the customers productive and happy, like really focused on that. And I like that type of work.
Can you go? 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 talking about 996. That was at least that for both Darmesh and I. We were pedals in the middle the entire time.
And if we weren't working, we were thinking about working. It's not for the faint of heart. If you look at my life, it's kind of interesting. 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 996 thing is 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.
You guys said something on a tweet that I thought was, you said it. 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. The temperature of the time is like, we got this.
We got it. Everything's going our way. The winds that are back. But it's pretty rare.
And like you live your day looking at your slack and your inbox and your text. And it's mostly bad news in there. Well, so tell me, once a company gets to 100,000 employees or 10,000 employees, does that emotion go away? Same.
It's the same ratio. It's still mostly 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 sales forces going to crush us tomorrow. Did you steal their announcement?
We're dead. We said that so many times. Yeah. We tend to overestimate where our competitors do and underestimate what we do.
Maybe there's a correlation between like how 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. You're shit. You're nothing.
You have to prove them wrong. You are horrible. You're barely grored. You can't do this.
You have to put it like it wears people out, though, because I actually think that that's a pretty poor way to motivate people. But it motivates me. I'm the same. And then 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, I have impostor syndrome. I'm a little nervous talking to you today. Believe it or not.
Really? Why? Yeah. I'm not.
It's given all the success I've had. My confidence doesn't even remotely. Let's look into it to it. In my inner monologous life.
You got so much to prove, dude. Don't fuck it up. Does Dar 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, 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 interviews. Do you have impostor syndrome? I mean, they hem and hem on hot, 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 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 even if you go big, you can land somewhere and be all right. The hard part is the uncertainty.
And asking yourself, am I spending time for the next six or 24 months on this thing? And will it actually make my 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?
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 the update's definitely outweigh it. I'm super proud of what we built.
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 forward, one step back. It looks like, oh, if you look at the grass, like, oh, that was an easy ride.
It wasn't. 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 mistakes and go forward.
Almost all the setbacks 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 chat GBT 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 my personal life and businesses. I uploaded so much information. And so the output is that I have this GBT 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 use to make this, the information that I had chat GBT 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 into your email and we will send you everything you need 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.
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 potful report. And we live in Boston in this, like this time of years, potfuls everywhere. And that was the analogy we used at HubSpot. Like we would create these potfuls.
And sometimes you kind of bounce through the potful and it would hurt a little bit. Sometimes the potful got so big like you drive your whole damn card in. And oftentimes there was a series of decisions or a series of data that we could have avoided the potful. So the potful report was every time we had a potful we'd look back and like, how should we have handled this a year ago, so that one of the things that we wish we had.
No, you have an example of it. We had a potful 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 we'd walk into an Apple store, we'd buy an iPhone and we'd hire the kid who sold us the iPhone.
And they wouldn't let me in the Apple store in Cambridge anymore, so many people. And so 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 background.
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 and to sales and to 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 them. And then we were a little behind on hiring and the customer numbers were way up. And so we pride ourselves on 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 is going on? That was a very solvable, predictable problem that if you just look at this as 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 going fast, everything breaks. You know, people break, process these breaks, this isn't break. Like everything's just breaking, breaking, breaking with you. 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.
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 gonna 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. So I refer to a second mountain business as something that's beyond just making your initial like financial security number. That really does take decades. You think I'm wrong there?
I don't know. I spend a lot of time with these companies to go zero to 20 in six months. No, I've been shocked. I've been 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.
Like some of them are like pretty legit and 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 was through 100 years ago. It was a little bit of the same many of the things that different as 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. 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 starting in 2009, HubSpot, you know, whatever to it to. You know, for in a 10 year period, a whole bunch of companies have 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 are sort of set. Same thing with mobile. It all happened within like a couple of years.
I try to 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 think I think it'll be different too. It's like out of 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 bubble will pop, but I think a lot more companies look about the other side. So, actually it's 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 pitches, so many pitches. And I'm trying to feel, 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 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 when the fatter pitches, you get the sense they're first principles in thinking or they're just derivative in thinking. L is, are they lovable?
Like in the question I asked myself, 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 work for me.
When I talk to people who used to work for you, they describe you, I think it's a material where they're like, you could be like really happy, but I only know you as a nice, like we only have a 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 yin yang kind of worked for us. But lovable is one. And by the way, these criteria, I don't match 100% all of them. Oh, it's 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 obsessed and 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 and radical, you're 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 an up-oh 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 the kind of a tourist industry? So I call it flocked. And if you have all those money, talent, partners, customers will kind of flock to you. And nobody's attending on all of them.
But that's kind of my rubric I use. Today's episode is brought to you by HubSpot. As 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.
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If you were young and getting after it at a new company, you're a 26 year old kid with flock, what interests you right now based on everything you're seeing? I think one of the things I'm seeing in Sequoia is like, you know that the hardware companies are kind of sat, the model companies are kind of sat, all that infrastructure layer sat, at the app level is really starting, is now starting to really fly. You know, cursor is 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. It was a bit exciting, but I like software that people use and can change their lives and prove organizations. I think that's where I would live.
I like this company, Rogo, which is like Think Chat, JPT, 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, 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 wanna train that clone not just on what's out there on the internet with me, but I train it on my email and my Slack and like all my calls and I wanted to train it 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 six months it just listens, but then people can start to ask my clone question, Hey Brian, what do you think about this? And Brian will answer. And then eventually it's just like, I don't use that meaning. I'm gonna send my clone to that meeting.
And you know, I have a lot of meetings really, 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 really doing that.
I want the opposite of that. I don't wanna clone to me. I want the better version of me to do all the work or like, you know, I don't want another mediocre me. I want the best version of me to be answering all the emails.
I ask my clone questions and get an answer to them much better than I would. Because it's sitting on top of Chat GPT. It's sitting on top of all kinds of knowledge. It's very, very smart already.
It has the models underneath get much better and has more content goes in there. It's gonna be very, very smart. Of course you're still gonna have your co-pilot. Like I think of Chat GPT 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 weird thing is that I've been using Chat GPT for so long it really knows me. It knows everything about me. All my health stuff like all the projects and 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 than I 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 I have the CO Goldman Sachs coming on like give me a bio the CO Goldman Sachs. Listen to all my podcasts I've done already.
Create me a list of 20 good questions or topics. Ask him and then time to go back and forth on. 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 solo. I got like they took like 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 just, I think you know I just know the new book my marketing lesson and grateful 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 I, 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. I 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 gonna be really much, much better than it's today. Yeah and it makes me think that I'm not gonna be investing in an entrepreneur anymore.
I'm gonna be investing in a machine that can just do all this stuff. Like I do think, I think Sam Albin 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 gonna happen. I think that the halves and the halves and the halves and the halves and the halves and the halves of money is gonna separate further.
And I asked Darmash when he came on because Darmash is heavily involved with, he's an investor of OpenAI and is a beep on this stuff. I was like, how is this gonna turn out? And he was like, it's probably not gonna be as good or bad as you think. And I was like, okay, 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 as an entrepreneur, I'd make it again. Yeah, this isn't very good time to be an entrepreneur and outstanding, it's like never been a better time. Never been a better time. The history of Homo Cpians, the start company might be.
Yeah, I think I agree. Dude, some of these young kids, they'll 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 is on fire. I think that's gonna make a lot of unhappy people. I think it's a bubble. And every time there's a bubble, like tourists, entrepreneurs come in, they're all coming in San Francisco which kind of bums me out.
And it kind of makes sense because Google's there and opening eyes here in that and they're out in the redown town, but many other people moving in. And there's a lot of tourists in there. Similar to that in 2001, similar to what happened in the late 90s. And I think it's peak bubble.
I don't know why 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 a bubble, what should you do? I'm not sure I'm maximizing my evaluation, so I call it, but let's say you want to do that.
Because you like the headline. Almost every entrepreneur, even starting at Series A, is taking money off the table. They're selling some of their own shares, which is way earlier than you just happened. And selling a lot.
What's the definition of a lot? You know what, typical, if it's Series B company is ripping, they're taking off $5 million bucks. And then I would just raise more. Like you look at 2001, lots of good companies raise, and then it crashed, and not many companies made it out of that value of debt.
I think you should raise a lot. So you can kind of make it through like, hey, I was gonna go like this, and then get down and keep going. Another profile of an entrepreneur I see a lot of. Then I hadn't seen before.
I call them like a five tool CEO, where they can 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, 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. Now you're seeing, I see a lot more of these like super heroes 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 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 him. Whatever I see, like whatever I see Shaq and like, you know, like a five, 10, or a five, or a five, 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 of mostly the same stuff? Yeah, and there's a bunch of early stage CEOs are like that, they're charismatic, they can sell, they can recruit, they can pitch, man, they can code and they have T8s, like it's an impressive new breed that's showing up.
I just got done reading this like sales book and how to run a sales team and the intro was talking about how it was your HubSpot's first, first head of sales, Mark. Yeah, and then I read another one and it was like, I was HubSpot's 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 are 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 principles. 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 were wrong, but enough people thought were right. And we had a 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 just sucked out of MIT.
We were two slownies that started the company. So our first 10 employees, eight of the first 10 were classmates of ours. We sucked over that helped. Mark Reber 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 competition. You got to 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 kind of first principles along along a few different lenses. We also kind of zig with them. World was zagging. The world said, you got to go to Enterprise.
That's where all the money is. We said, no, no, no, no. 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, you're crazy.
You'll never beat them. We went after them. So there's a bunch of points in up-spot histories where we kind of zig 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 SMB thing.
It cost us. We would raise, we would go raise our rounds. We'd walk down the same door. We had all those.
We never had the only easy rounds, the IPO rounds. Nobody liked the thesis. Nobody bought the SMB thesis. No one else had done it other than into it.
And we worked with 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. I'll be this small business grow better. The Salesforce thing, we got a lot of pushback on that. But we didn't feel like we had a choice.
Salesforce was our really good ally. And our pitch was salesforce.com was SFA for sales and help I 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 we're eventually just going to get crushed and pushed out and sold practically.
I'm trying to become a better CEO. And I know that you guide a lot of CEOs. I said, 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 of 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 like, you know, back in my day was Jack Welch, and I was just at home.
And Jensen does this 60 direct reports. He's tough like I was. And he gives public and private feedback. Now he doesn't get private feedback.
All the feedback positive negatives. And then he doesn't want to want to once. 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, Brian, you need a staff meeting with just your direct reports. You should only have nine direct reports. No, no, Brian, you should freeze 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 manage or moodiest time went on. I've got that. Of the manager mode stuff, what do you think actually 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-mody. We did bring in some execs from the outside that were very, very good and really up leveled us. 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 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? And they're lost at C in this startup. And their 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 hunger and 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, 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 HubSpot had like five or six employees, which one of them is now like on the board of Asana. So these big shots. And then you guys had like seven or eight lawyers who were 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 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, 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 Fiver.
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 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 it quarterly by quarterly, but like shit changes. And they were pretty cool where they were like, okay, we understand. Like, you know, they're 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're 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 two years, let alone like what the financials are going to be. And that was like pretty funny.
And it like it rattled because the people I was talking to were just hires. Like they had never like funded a company. And 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 like a huge distinction between me just being still in entrepreneur mode and them 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. There's literally no assets, no revenue, nothing to lose. And as they get bigger, they're more to lose. And the lawyers get more involved because they want to 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 and mark a cap. We have a lot to lose.
But I think the mindset 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 Dunbar's number, all kinds of shit goes wrong there.
The director layer shows up. So it's like one more layer between the CEO and the customer. It kind of messes up up up. The people joining are a little more mercenary and a little less missionary who exchanges 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 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 Ripley's doing this very aggressively. More and more CEOs are hiring failed founders, like, or doing very cheap back by hires and kind of seeing their whole company with founders, like Ripley's got over 100 ex-founders on their team. And I think that's good. That keeps you focused on the long haul and receiving.
You got to keep the receiving up for long, long periods of time. This is for the folks out there who have a business that does at least $3 million of your 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 a room of vetted peers, of other entrepreneurs who are going to 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 going to 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 can change mine and I know it will change yours. So check it out, joinhampton.com.
You're so fascinating to me because one of the very few people on earth who's built the company to be worth tens of billions of dollars. And 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 Jerry Garcia for a second. He's like, not the first, but what are the first in the very classic Silicon Valley entrepreneur? The company was founded?
Yeah, I, well, I've been the house across the street from Ben and Jerry's and had hit Ashbury, right? 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, right in Palo Alto. And so it's like 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.
Very late, he'd say to go. For example, at the time, Rockamroll 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 good Silicon Valley spiky.
And his base player was actually an Amman Guard 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 rest.
So he brought together this very spiky team. And instead of creating rock and roll, he created a whole new genre called Jambak and fish and so many other bands popular. And so how's about 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 he go to go to a Rolling Stones concert, let's say in 1980, he bring in all your equipment to the concert, big camera, microphone, whatever, 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 his account. The Grateful Dead.
If an idiot like me, he showed up with a camera and all his recording was boom, Mike, Frank, 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, 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 would trade. We weren't allowed to sell the tapes. That wasn't part of the calls.
We'd trade the best tapes with all your friends. 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. Like, you put your boot leg on and the person is like, why?
Everyone's dancing crazy chips. What is this weird gypsy music? You have this Grateful Dead. They're coming down town.
Come on tour with us. And so the Grateful Dead were the first Silicon Valley viral inbound marketers. So he was very first principal about his music and his marketing. A lot more stuff about his marketing.
I think he's very interesting. She, I mean, I've been to my parents or dead heads and they traveled with them, like, you know, show to show. I'm just Google. I'm like, you said you're 58.
I'm a very young guy. Dude, this guy looks like 30 years older than you, but he died when he was only 52 or 53. Garcia. Yeah.
He was, he did not take the, he's not like the Silicon Valley people like Brian Johnson, Peter, Andrew, he woman, he is his major food. He's for 20, 20, he's in 20s. Yeah. He looks like he parties.
What's the name of the book called marketing lessons from the Grateful Dead by it in triplicate? 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, 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 naming, great for dead. Like, one of the first things that comes up is that you bought, you know, his guitar at an auction. Yeah.
I have a job. I consider myself a steward of his guitar. It's very unique guitar. I played it all through the 70s and yeah, I own it.
And I let it out. Like John Mayer played it. Like everybody in the brothers, anyone who wants to borrow it can borrow it. But yeah, I enjoy being the steward of a little piece of jargarcarcia.
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 admire, 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 and my friends. I want to be like you and I grow up. All right, God bless.
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