My First Million - 7 Brutal Questions for a $20B Founder

Episode Date: December 26, 2025

Get Sam's AI Executive Coach Playbook - his exact system for everything from revenue optimization to life decisions: https://clickhubspot.com/dhn Episode 778: Sam Parr ( ⁠https://x.com/theSamParr⁠ ) talks to Brian Halligan ( https://x.com/bhalligan ) about the highs and lows of building HubSpot.  — Show Notes: (0:00) Are you happy? (2:57) Does it ever stop sucking? (5:18) Do you have imposter syndrome? (6:55) Were the trade offs worth it? (11:53) Is AI a bubble? (14:47) Do you have to be liked? (17:02) What would you do if you had to start over? (29:36) What did you get wrong? — Links: • Marketing Lessons From The Grateful Dead - https://tinyurl.com/ydmyh6f9  — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com  • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano //

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 feel like I can rule the world. I know I could be what I want to. 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're running a $20 or $30 billion company? Or how about happier compared to when you're 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, 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. I'm going to give you like the grading system in my head for a number of employees. Like two to ten employees. I was like a C. I didn't really, I could write code, but no one wanted it.

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. 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. Like I had sort of CEO market fit between 10 and 1,000. That's like 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 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 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 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 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 category is. 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 talk about 996.

That was at least that for both Darmesh and I. We were peddled to the metal the entire time. And if we were working, we were thinking about working. It's not for the feign of heart. 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 9-96 thing, it's at least that for the founders. And I work with a lot of founders today. 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. 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 that are back. But it's pretty rare.

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 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, whereas like, if we don't do this well, we're going out of business. 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. Yeah, we tend to overestimate where our competitors do and underestimate what we do. Maybe there's a correlation between like how, 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 notice 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 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 imposter syndrome. I'm a little nervous talking to you today. Believe it or not. Really? Why? Yeah. Given all the success I've had, my confidence doesn't even remotely compare to it. And my inner monologue is like, you've got so much to prove, dude.

Don't fuck it up. Does Darmash 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, do you have imposter syndrome?

And they have them 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 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 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 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.

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 easy ride. It wasn't. We have 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 mistakes 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 and to 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 in 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 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 chat Chb-T 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 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 Pop-hole Report. And we live in Boston in this, like this time of years, pop-holes everywhere.

And that was the analogy we used at HubSpot. Like, we would create these potholes. And sometimes he kind of bounced through the pothole and 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 look back and like, how should we have handled this a year ago? So that wouldn't have happened. What data do we wish we have?

I'll give me an example of that. We had a powerful in like 2011. One of the things we did at HubSpot is we hired really good support people. And our secret sauce in hiring a support is we'd 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 Cambridge anymore. We heard so many people. 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 problem. How many support people did you have? we must have had the 40, 30, 40. And then what we would do is we used that support group to promote into CSMs, into sales, into products. So we fed the whole company really with these Apple store 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 promoted 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, you know, 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, 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 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 in 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 refer to a second amount of business as something that's beyond just making your initial 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 of these companies that go zero to 20 and six months now. I've been shocked. I're 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, like, if I look back, like, 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 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. That's what's different about today. 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, 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 of 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 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 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 from out the other side. Sequoie 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 pitch, so many pitches. And I'm trying to, you know, 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 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 in a, like in a lot. Like in a, is, is, is that, are they lovable? Like, in a lot. And, like, in a. And, 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 work for me. When I talked to people who used to work for you, they described you, I think, as mercurial, where they're like, you could be, like, really happy. But I only know you as a nice, like a, 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, Ying and Yang kind of work for us. But lovable is one. 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 were the world's best, you know, northeast New England, you know, ping pong player, whatever would be, something where they had to go very, very deep down a rabbit hole. 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 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, 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 flocked.

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 want to 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, 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 very 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 kind of an app guy. I don't really like infrastructure software that much. I don't think that exciting, but I like software that people use and can change your lives, improve organizations. I think that's where I would live. I like this company Rogo, which is like, think chat chip 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 going to 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'm 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 on the internet with me, but train it on my email and my Slack and all my calls. And I wanted 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 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 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. 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 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. Because it's sitting on top of Chatubit. 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. Of course, you're still going to have your copilot. I think of Chat Chachybti, 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 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 I've been using Chat Chabot-G-T 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. of irritating, that I'm going to 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 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 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 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 think, you know, I just come out with a new book, my marketing lesson in the Grateful Dead. We created a very, very cool set of videos around it that are AI generated that are super, super cool that I like a lot. So I've been

busy with it and it's giving 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 and a therapist of like how should I react or how should, 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 8.000. And now it's 8. 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 Altman said he's like

if open AI 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 haves nots have nots in terms of money is going to like separate further. And I asked Darmesh when he came on because Darmash, you know, is heavily involved with or he's an investor of OpenAI and is a 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, 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 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 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. The history of homo sapiens to start a company might be. 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 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 on fire. I think that's going to make a lot of unhappy people. I think it's a bubble, and every time there's a bubble, like tourist entrepreneurs came 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 opening eyes here and they had prop like right downtown. But man, are people moving in? and there's a lot of tourists in there. Similar to happen in 2001, similar is what happened in the late 90s. And I think it's peak bubble. I don't know what it pops.

It pops at some point. A lot of those tours just get washed out. So my advice to entrepreneurs is like if it's a bubble, what should you do? I'm not sure maximizing evaluations is the right call, but let's say you want to do that because you like the headline. 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 used to happen. and selling a lot. What's the definition of a lot? You know, a typical, if the 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 raise, and then it crashed, and like not many companies made it out of that valley of debt. 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 that I hadn't seen before.

I call them like a five-tool-c. where they think code, they have taste, 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. 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 and me, like the extrovert, the introvert, like the Yang and the Yang. Now you're seeing, I see a lot of, 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, 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 510 lady or a 5-4 lady, I'm like, how are these both humans?

Yeah. That's what I feel about. what I hear Brett Taylor talking to me, I'm like, how are we like made up of mostly the same stuff? Yeah, and 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, first head of sales. Mark.

Yeah, and then I read another one. 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 principled.

So we were like marketing is totally broken. Outbound is 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 view. Most people thought were wrong, but enough people thought 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 business 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, eight of the first 10, were classmates of ours, we sucked over. That held. Mark Rabears 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've 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, 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 along a few different lenses.

We also kind of zig with the world was zagging. The world said, you've got to go to Enterprise. You know, that's where all the money is. We said, no, no, no, no, no. We're going to do S&B. We're going to rethink this. We're going to make the model work at S&B, even though everyone thinks were wrong. And then we said, we're going to go after Salesforce.com.

When Salesforce.com was, like, unassailable. Everyone's like, oh, you're crazy. You'll never beat them. We weren't after them. So there's a bunch of points in Uspot history. where we kind of zig when everyone else, you know, Peter Thiel is 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 a real conviction on the SMB thing. It cost us. Like, we would go raise our rounds. we go up and down San Hill Road. We had all knows. The only easier round was the IPO round. Nobody liked the thesis. Nobody bought the S&B thesis.

No one else had done it other than into it. And we were convicted us. 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 pushback on that, but we didn't feel like we had a choice. Salesforce was our really good ally. And our pitch was, you know, Salesforce.com was SFA for sales, and Huffbot 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 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 and thinking that was what I did early. Those were my instincts. And I kind of get 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, it was Jack Welch and I was Jason Wong.

And Jensen does this, he's got 60 direct reports. He's tough like I was and he gives public and private feedback. He doesn't give private feedback, all the feedback positive negatives and then he does a new one-on-ones. And I did all of that early in HubSpot and sort of got talked out of them. Like, no, no, no, no, Brian. A mature CEO does a one-on-one with each manager every week.

No, no, no, no, Brian. You need a staff meeting with just your direct reports. You should only have nine direct reports. No, no, 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 watch what Jensen is 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 managed. 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 got her shit together on planning. Like, we were very shoe 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 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 are like, where's my secretary? Where's my coffee? Where's reports? Where's all my stuff?

They're lost and C 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 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 of 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 like 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 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 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. Do you have like projections? I'm like, 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 were treating this like, you know, like 30 million dollar deal. Like it was a three, $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 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 what the company is 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 the, because the people I was talking to were just hires. Like, they had never, like, founded a company.

And 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, like, a huge distinction between. between me just being still an 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 cross the T's

and dot the eyes. 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? 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 and 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. 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 protect what we have versus go get something new. is interesting. And what it's happening in Silicon Valley that I think is interesting, and the CEO of Rippling's doing this very aggressively. More and more CEOs are hiring, you know, failed founders, like, or doing very cheap aqua hires and kind of seeing their whole company with founders, like Rippling's got over 100 X founders on their team. And I think that's good. That keeps you, like, focused on the long haul and risk seeking. You got to keep the risk seeking up for a long, long period of time. 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 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 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 the 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, There's layers. That's why I think it's, I think you're fascinating.

Let's talk about, 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? Yeah, I, well, in the house across the street from Bedin-Jerry's in Hayd Ashbury, right? No.

It was founded in Palo Alto. Oh, interesting. It's like right 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 and 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, 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 bass player was actually an avant-garde trumpet player that learned the bass. His keyboard player was actually a blues harmonica guy. His dad was the blues DJ in town. His main singer was a country cruder, and his drummer was like a drummer. 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 Fish and so many other bands copy them. And so Hotspot did the same thing.

Yet we said this outbound thing is dead. We're going to create the genre called inbound marketing. So very first principle of 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, you go to walk in the concert. Get out of here with all your equipment.

This is our IP. This is Rolling Stone's on us. Get out. They're grateful dead. If an idiot like me, shut out of his camera and all his recording, quits, boom, Mike.

Brian, come on it. 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 get back home. We have the tape-to-tape thing. And the best concert would make 50 copies of. And then we'd trade, we weren't allowed to sell the tape. So it wasn't part of the cause where you trade the best tapes with all your friends. So you pick up their best stuff in 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 party on campus and somebody put your bootleg, you put your bootleg on. And the person next to you'd be like, why everyone's dances, crazy gypsy. What is this weird gypsy music? It's Grateful Dead. They were coming in town. Come on tour with us. And so they're grateful they were the first. first Silicon Valley viral inbound marketers. So he was the very first principle about his music and his marketing.

There's a lot more stuff about his marketing. I think he's very interesting. I mean, my parents were deadheads 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? Yep. I'm a very young deadhead. Dude, this guy looks like 30 years older than you, but he died when he was only 52 or 53.

Garcia, yeah. He did not take... He's not like the Silicon Valley people like Brian Johnson, Peter, Andrew Heuberman fan. His major food groups were Twinkies, Twinkies, and Twinkies. Yeah, he looks like he parties. What's the name of the book? Called Marketing Lessons from the Grateful Dead.

Buy it in triplicate. You've got to buy that for your parents. Did you get to meet them when you're writing it? I met Bob Weir, yes. 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. His reaction was really, 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, you know, his guitar at an auction. Yep. I have Jerry Graham. 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 in their brothers, anyone who wants to borrow it, can borrow it. But, yeah, I enjoy being the same. 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's kind of like where I want to go, but in a handful of years. So I, uh, 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. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back. 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,

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