Should You Start a Company? The Honest Truth

- December 26, 2025 (3 months ago) • 42:04

Transcript

Start Time	Speaker	Text
00:00	Brian Halligan	We were constantly like, "Salesforce is going to crush us tomorrow. Did you see their announcement? We're dead." We said that so many times. I'm excited to be on your show.
00:15	Sam Parr	"It's kind of our show, Brian."
00:16	Brian Halligan	Yeah, it's true.
00:18	Sam Parr	"Do you consider yourself retired?"
00:19	Brian Halligan	I don't think I'll ever retire.
00:21	Sam Parr	"But you're not the CEO of a company."
00:23	Brian Halligan	No, I have a whole bunch of interesting stuff going on.
00:27	Sam Parr	Are you happier in this phase of your life than when you were running a $20 or $30 billion company? Or how about compared to when you were running a $10 million company? Where have your levels of happiness been? You founded a company that now has, I don't know, 5,000–7,000 employees and billions in revenue. Now you're retired—not exactly retired, but you're not running a company and you're a bit of a VC and advisor. So tell me about your happiness levels between each one. </FormattedResponse>
00:55	Brian Halligan	Okay, I'm going to give you the grading system in my head for a number of employees. 0 to around 2–10 employees: I was like a C. I could write code, but no one wanted it. You don't add a lot of value at that phase. 10 to 100: This was like an A. I felt like I knew what I was doing — I had been in scale-ups before. 100 to 1,000: Maybe a — I kind of felt like I knew what I was doing. 1,000 to 10,000: I didn't enjoy it. "The secret of life is enjoying the passage of time." I wasn't really enjoying the passage of time. It was a lot of... I was just working on a lot of stuff I wasn't that interested in. So, it depended on where I was in the history of HubSpot. I had sort of CEO–market fit between 10 and 1,000.
01:45	Sam Parr	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?
01:55	Brian Halligan	Yeah. My first job out of school, I was the first BDR at a company called PTC — it's a CAD software company. I joined when it was about $3 million in revenue, and when I left it was, you know, billions in revenue. I sort of saw that journey and I was part of that machine, so I took a lot of that experience with me into HubSpot. I just felt like I knew what I was doing there, and I was working on things I really enjoyed. There's a lot that changes between 100 and 1,000 [employees]. I remember being quite motivated and happy with my day-to-day work in that phase — very little concern about what the nomination and governance committee of the board [nom & gov committee] thought, and very little interaction with our compliance and legal folks. It was mostly just working on whether the employees were productive and happy and whether the customers were productive and happy — really focused on that, and I like that type of work.
02:50	Sam Parr	"Can you go... Okay, so your categories were 2 to 10, 10 to 100, 100 to 1,000, and then 1,000 to 10,000. What about how hard you are working—like in terms of hours?"
03:01	Brian Halligan	Yeah, people talk about 9-9-6. That was at least that for both Jarmesh and me. We were pedal to the metal the entire time. 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. You're kind of married to your company — you're full-on the 9-9-6 thing. It's at least that for founders. I work with a lot of founders today; that's the minimum, I'd say. You guys said something in a tweet that I thought was interesting: "When you're a founder, like 90% of the time stuff's broken and you're dealing with problems."
03:47	Sam Parr	Things kind of suck. I'm angry. I'm angry most of the time.
03:51	Brian Halligan	Most of the time I'm angry. Most of the time... 10% of the time it's like, "We got this. We got it. Everything's going our way. The winds are back." But it's pretty rare. You live your day looking at your Slack, your inbox, and your texts, and it's mostly bad news in there.
04:04	Sam Parr	"Well, so tell me: once a company gets to 100, or 1,000, or 10,000 employees, does that emotion go away?"
04:13	Brian Halligan	Same — it's the same ratio. It's still mostly a "shit sandwich" in your inbox.
04:19	Sam Parr	"Do you feel an existential threat? Like, my business — we have plenty of money and are very profitable, but for some reason I still feel like there's an existential threat all the time. It's like, 'If we don't do this well, we're going out of business.'" </FormattedResponse>
04:32	Brian Halligan	We were constantly like, "Salesforce is going to crush us tomorrow. Did you see their announcement? We're dead." We've said that so many times. Yeah — we tend to overestimate what our competitors do and underestimate what we do.
04:46	Sam Parr	Maybe there's a correlation between how shitty you think you are and how good of an entrepreneur you become. Maybe there's no correlation, but I notice a pattern in people who start businesses. I personally have very negative self-talk. It's like: "You're shit. You're nothing. You have to prove them wrong. You are horrible. You've barely grown. You can't do this." That kind of talk wears people out. I actually think that's negative — it's a pretty poor way to motivate people — but it motivates me.
05:17	Brian Halligan	I'm the same. I have people say, "You know, you want to be very positive and motivate people." I tend to be paranoid. I still, after all these years, have impostor syndrome. I'm a little nervous talking to you today, believe it or not.
05:32	Sam Parr	Really? Why?
05:33	Brian Halligan	Yeah, I'm not. It's all the success I've had — my confidence doesn't even remotely compare to it. My inner monologue is like: "You got so much to prove, dude. Don't fuck it up."
05:47	Sam Parr	Does Darmesh feel the same way?
05:49	Brian Halligan	Yeah, I can't say for sure, but I think very much so.
05:53	Sam Parr	Do most others... So you run in a circle with some of the best entrepreneurs on Earth — the most successful entrepreneurs on Earth. Is that the common thread? </FormattedResponse>
06:00	Brian Halligan	Yes — almost all of them. I interview all these CEOs, and I ask them during the interviews, "Do you have impostor syndrome?" They hem and haw because they don't want to say they do. They do — almost all of them.
06:12	Sam Parr	Let me ask you one more question about all this, and then I want to know more about your 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 — is that 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. Even if you go big, you can kind of land somewhere and be all right. The hard part is the uncertainty: asking yourself, "Am I spending time for the next 6 or 24 months on this thing, and will it actually make my life better or get me to where I think I want to go?" That uncertainty part is quite challenging. Looking back, was dedicating all this time worth it? Do you look back at the last 20 years and say, "That was a life well lived," or would you have changed anything?
07:04	Brian Halligan	No, I think it was... I'll take the trade-off. It was a lot of fun. I mean, it 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 up days definitely outweighed them. I'm super proud of what we built. You know, yeah—I wouldn't trade it. The thing I would say about HubSpot is—it's a little bit of what you said—but I think of it as like HubSpot was two steps forward, one step back; two steps forward, one step back. If you look at the graphs, it might look like it was an easy ride, but it wasn't. We had lots of issues, lots of problems, and lots of setbacks along the way. It's a little bit what good entrepreneurs do: they just stick with it. There's problems and issues and that step back, and they don't fold. They just say, "We're gonna get through it. We're gonna rally the troops. We're gonna figure it out. We're gonna learn from those mistakes and go forward." Almost all the step backs were self-inflicted.
08:08	Sam Parr	Alright. A few episodes ago I talked about something and I got thousands of messages asking me to go deeper and to explain. That's what I'm about to do. I told you how I use ChatGPT as a life coach or a thought partner. What I did was upload all types of personal information: my finances, my net worth, my goals, books I like, issues going on in my personal life and businesses. I uploaded so much information that the output is a GPT I can ask about problems I’m facing in life—questions like, "How should I respond to this email?" or, "What's the right decision knowing my goals for the future?" I worked with HubSpot to put together a step-by-step process showing the audience the software I used to make this happen. ChatGPT asked me all this stuff, so it's super easy for you to use. Like I said, I use this 10–20 times a day—it’s literally changed my life. If you want that, it's free. There's a link below: just click it, enter your email, and we will send you everything you need to set this up in just about 20 minutes. I’ll also show you how I use it again 10–20 times a day. Alright, 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?"
09:26	Brian Halligan	One of the things we did that worked was a thing we called the pothole report. We live in Boston, and this time of year there are potholes everywhere. That was the analogy we used at HubSpot. We would create these potholes. Sometimes you'd kind of bounce through the pothole and it would hurt a little bit. Sometimes a pothole got so big you'd drive your whole damn car in it. Oftentimes there was a series of decisions or a series of data that we could have used to avoid the pothole. So the pothole report was: every time we had a pothole, we'd look back and ask, "How should we have handled this a year ago so that wouldn't have happened? What data do we wish we had?" I'll give you an example. We had a pothole in 2011. One of the things we did at HubSpot was hire really good support people. Our secret sauce in hiring support was: we'd walk into an Apple Store, buy an iPhone, and hire the kid who sold us the iPhone. They wouldn't let me in the Apple Store [but Jenny and Mark came with me]. We hired so many people. The value prop was great. It was like, "You make a little bit more money, but how'd you like to sit down at work?" It was a really good value prop.
10:33	Sam Parr	"How many support people did you have?"
10:36	Brian Halligan	We must have had the 40, 30, 40. What we would do is use that support group to promote into CSMs, into sales, into product. So we fed the whole company, really, with these Apple Store people that were terrific. And in this one particular period — over a few months — we promoted a bunch of people out, congratulated them, and promoted them. We were a little behind on hiring, and customer numbers were way up. We prided ourselves on answering the call within 30 seconds and then staying on as long as they wanted. Now 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. If you had just looked at this as one chart, we wouldn't have made that mistake. Yeah — we won't make that mistake again. We never make that mistake again. So, so many things like that along the way. As you grow — if you're going fast — everything breaks: people break, processes break, systems break. Everything's just breaking, breaking, breaking with scale.
11:36	Sam Parr	What I've noticed, particularly talking to people on MFM, is that it really takes 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 — you guys were at $20,000,000 in revenue by year six, which is pretty huge. I think 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 there is a correlation between how fast something grows and potentially how fast it can die. But I do think that in order
12:07	Brian Halligan	To build.
12:07	Sam Parr	Something that's a "second mountain" business. I refer to a second mountain business as something that's beyond just making your initial financial security number, which really does take decades. Do you think I'm wrong there?
12:21	Brian Halligan	I don't know. I spent a lot of time in these companies that go zero to 20 in six months. I'm shocked — I'm shocked at how fast these companies are growing. There are a lot of them. 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: selling to non‑tech companies and building real businesses. So, if I look back — assuming we're in a bubble today — I look back at the bubble in 1999 that I lived through (a hundred years ago). It was a little bit of the same mania. The thing that's different is the startups back then were only selling to each other. When the house of cards fell, it kind of fell on everybody. They really didn't have much growth or much revenue. That's what's different about today. I think the difference is the products are different. You think about SaaS or you think about mobile. SaaS kinda started in the, like, you know — Salesforce started in 2009, HubSpot… you know, whatever, in a ten‑year.
13:25	Brian Halligan	A whole bunch of companies started, but not much happened after that ten-year period. 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 a couple of years. I kind of think the same will happen 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. The thing I think will be different this time is: out of the last wave, Amazon came out, Google came out, eBay came out, Salesforce came out — there were like four legit, lasting, great companies that emerged. I think there'll be a lot more this time. This bubble will pop, but I think a lot more companies will come out the other side.
14:07	Sam Parr	"Sequoia is the best of the best. You guys see everything and you see the best companies. What are the trends that you're seeing right now among the companies that are 'rocket ships' but that you also think are going to be durable? Are there any trends you're noticing among the entrepreneurs that set them apart from previous generations?"
14:30	Brian Halligan	Okay. I came up with a rubric—I see a lot of pitches, so many pitches—and I'm trying to figure out what's my unfair advantage. My unfair advantage is that I spend a lot of time with CEOs, thinking about CEOs, thinking about the job. I've done that. So I thought about what kind of rubric I can come up with, and I came up with something I call FLOCK. - F is: do you get the sense the founder is first-principled in their thinking, or are they just derivative? - L is: are they lovable? The question I ask myself is: "If I were 27, graduating from Sloan, would I walk over broken glass to work for this CEO?" I think that's a pretty good question. Were they lovable? I don't know. You tell me—you work for me.
15:13	Sam Parr	When I talk to people who used...
15:14	Brian Halligan	To work for you, they describe you. I...
15:16	Sam Parr	Think mercurial, where they're like, "Yes, you could be really happy, but I only know you as nice — I only have a cordial relationship, a very cordial relationship." They would say, "When he was angry, he would get really, really angry."
15:32	Brian Halligan	Very true. I was up and down and it reflected my mood. My mood was up and down and I had a hard time hiding it. I had great passion — that passion really showed up in an aggressive way. I was definitely like Darmesh was the teddy bear; I was sort of the bad cop a little bit. I was definitely tougher than Darmesh, and I think that yin and yang kind of worked for us. But lovable is one. By the way, these criteria — I don't match 100% of them. Obsessed. I like founders who have been thinking about the damn problem for a long time and then finally start the company and are just obsessive-compulsive. I like to see a founder who was obsessed with something earlier in their life — maybe they were the world's best New England ping-pong player or something — where they had to go very, very deep down a rabbit hole and get very good at something. I think that's a good quality. I like the chip on the shoulder. I had a bit of a chip on my shoulder; I think Darmesh did too. I like founders who have a chip. If it's an IPO baby, I'm kind of skeptical whether they're going to stick through the ups and downs. Are they deeply knowledgeable? Do they have, you know, "founder-market fit"? Do they know everything about this industry, or are they kind of a tourist in the industry? So I call it flock: if you have all those, money, talent, partners, customers will kind of flock to you. Nobody's a 10 out of 10 on all of them, but that's kind of the rubric I use.
17:01	Sam Parr	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 on everything you're seeing?
17:14	Brian Halligan	I... one of the things I'm seeing at Sequoia is that the hardware companies are kind of set, the model companies are kind of set—all that infrastructure layer is set. The app level is now starting to really fly. Cursor is the really obvious one, but like Harvey and Rogo for investment banking—every kind of job now has an app company that's doing pretty well. 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 it's that exciting. But I like software that people use and that can change their lives and improve organizations. I think that's where I would live. I like this company Rogo, which is like—think ChatGPT-like but for an investment banker—and it's doing very well. I like Harvey, which is for lawyers. I like Profound, which is 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. What I really want as a consumer—it isn't here yet, and I'm for it—is: I build a clone, people can talk to my clone all they want. It's pretty good and it's getting better every day. I want that. I want to train that clone not just on what's out there on the internet about me, but train it on my email and my Slack and all my calls, and really have it know a lot about me. Instead of sending a listener to a meeting, I send my clone to a meeting that listens. In 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. Eventually it's like, I don't need to go to that meeting—I'm going to send my clone. 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.
19:07	Sam Parr	"I want the opposite of that. I don't want a clone of me. I want a better version of me to do all the work. I don't want another mediocre me—I want the best version of me answering all the emails."
19:20	Brian Halligan	I ask my clone questions, and it answers them much better than I would because it's sitting on top of ChatGPT. It's sitting on top of all kinds of knowledge—it's very, very smart already. As the models underneath get much better and as more content goes in, it's going to be very, very smart. Of course, you're still going to have your "co‑pilot." I think of ChatGPT, and now I use Gemini mostly as an even better coworker than a lot of my coworkers. So you definitely have that. But I think knowledge work is going to change. I think my vision of the future—I'm not sure if it's five years out—but I think something like that happens.
19:57	Sam Parr	Can you tell me how you're using Gemini right now on a daily basis?
20:00	Brian Halligan	The weird thing is, I've been using Traci BT for so long it really knows me. It knows everything about me—my health stuff, all the projects I'm working on—everything. It's tricky for me because I trained it so much. But man, Gemini is so much better. I'm starting to use Gemini, and it's kind of irritating that I'm going to have to train it on myself. The thing I really like are the projects functionality. For example, on my podcast I have all these different guests. I have the CEO of Goldman Sachs coming on. I can say, "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 go back and forth on it. I do that for every podcast—it's super, super, super useful. I went to Function Health and got all my blood work. I got upsold; they took, like, gallons of blood out of me, but I know everything about it now. I uploaded all that and collaborated on that stuff. It's incredibly valuable these days. I just came out with a new book, "My Marketing Lesson from the Grateful Dead." We created a very cool set of videos around it that are AI-generated and that I really like. I've been busy with it, and it's given me a massive productivity boost. I feel like there's two of me already.
21:24	Sam Parr	I find it to be very helpful as a daily coach and a therapist—helping me figure out how I should react, or why I feel this way about a particular situation. When it comes to creative stuff, I find it to be helpful, but it's not even close to being hands-off. </FormattedResponse>
21:40	Brian Halligan	But think about it: two years ago it was 50%, a year ago it was 65%, and now it's 80%. Keep drawing that curve. Two years from now it's going to be much, much better than it is today.
21:54	Sam Parr	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. I do think Sam Altman said, "If OpenAI isn't the first company that has an AI as the CEO, then I'd be pretty upset." I do think that's sort of going to happen. I think that the haves and the have-nots—in terms of money—are going to separate further. I asked Darmesh when he came on, because Darmesh is heavily involved with, or is an investor of, OpenAI and is deep on this stuff. I was like, "How is this going to turn out?" He was like, "It's probably not going to be as good or bad as you think." 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 who has the best judgment on this topic.
22:41	Brian Halligan	I kind of think the way.
22:42	Sam Parr	It plays out as people who...
22:43	Brian Halligan	They're very high-agency and motivated. It unleashes their creativity and potential. People who aren't might be unemployed.
22:53	Sam Parr	Are you happy that you've made it already?
22:55	Brian Halligan	"No, I think if I were 26 and an entrepreneur, I'd make it again. Yeah — this is a very good time to be an entrepreneur, and, like, an outstanding... it's like never been a better time. Never been a better time in the history of Homo sapiens to start a company. It might be..."
23:11	Sam Parr	Yeah, I think I agree, dude. Some of these young kids, though, seem crazy. I don't remember when I was in San Francisco back in 2012 — it was a much calmer environment than what it seems like now. Do you think that's an accurate assessment?
23:24	Brian Halligan	"Yes, everyone's hair is on fire."
23:27	Sam Parr	"I think that's going to make a lot of unhappy people."
23:30	Brian Halligan	I think it's a bubble. Every time there's a bubble, tourist entrepreneurs come in — they're all coming into San Francisco, which kinda bums me out. It kinda makes sense because Google is there and they're opening offices here, and they [unclear phrase: "anthrop back in there"] right downtown. But man, people are moving in and there are a lot of tourists — similar to what happened in 2001 and in the late '90s. I think it's peak bubble. I don't know when it will pop, but it will pop at some point. A lot of those tourists just get washed out. So my advice to entrepreneurs is: if it's a bubble, what should you do? I'm not sure "maximizing valuation" is the right call, but let's say you want to do that because you like the headline. Almost every entrepreneur — even those 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.
24:14	Sam Parr	"What's the definition of 'a lot'?"
24:17	Brian Halligan	You know what? Typically, if a Series B company is ripping— they're taking off $510,000,000—then I would just raise more. Like, you look at 2001: lots of good companies raised and then it crashed, and not many companies made it out of that valley of death. I think you should raise a lot so you can kind of make it through. AI is going to go like this, then go down, and keep going... another profile of entrepreneur I see a lot of...
24:38	Sam Parr	Yeah.
24:39	Brian Halligan	"I call them a five-tool CEO, where they think in code, they have taste, they can sell, they can fundraise, and they can recruit. They're the kind of perfect entrepreneurs. Bret Taylor is one of those. There are 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 before. You used to see a lot of Darmesh and me — like the extrovert and the introvert, the yin and the yang. Now I see a lot more of these superheroes showing up."
25:15	Sam Parr	"I don't understand. I've met some of these guys, and this guy Bret Taylor in particular — I don't know him, but I would love to have him on. 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?'"
25:28	Brian Halligan	I totally agree. I totally agree with you.
25:31	Sam Parr	Whenever I see Shaq and, you know, a 5'10" or a 5'4" lady, I'm like, "How are these—how are these…?" That's what I feel when I see or hear Bret Taylor talking to me. I'm like, "How are we made up of mostly the same stuff?" </FormattedResponse>
25:48	Brian Halligan	"Yeah, there's a bunch of early-stage CEOs like that. They're charismatic: they can sell, they can recruit, they can pitch. But, man, they can code and they have taste. It's an impressive new breed that's showing up."
26:00	Sam Parr	I've just finished reading this sales book. The intro was talking about HubSpot's first head of sales. </FormattedResponse>
26:09	Brian Halligan	Mark.
26:10	Sam Parr	Yeah. And then I read another one, and it was like, "I was HubSpot's first SEO person." There are four more like that. It seems like your first 50 employees are now pretty big ballers—doing their own thing, or they're experts and people look up to them. What do you think made you so good at recruiting, and how did you do it?
26:33	Brian Halligan	I think in the early days we were very first-principled. We believed marketing was totally broken: outbound's dead—no one's listening to ads, cold calls, or emails. You have to do inbound. We had a contrarian view. Most people thought we were wrong, but enough people thought we were right. We had a mission: apply that idea to helping small businesses grow. Lots of people grew up in small-business families and want to help small businesses grow. It's a mission you can get behind—helping millions of small businesses grow better. I think that helped early on. We had just come out of MIT Sloan; we were two Sloanies that started the company. Eight of the first ten employees were classmates of ours. Mark Roberge was our TA—he's actually the guy who wrote that book you were talking about. Then we worked on culture. We had a unique culture. We thought of our product this way: you have to make a unique product relative to the competition and you have to make a quality product. If you do that, it pulls customers in. Likewise, you need to build a unique, high-quality culture, and if you do that you pull and retain employees. We were first-principled along a few different lenses. We also zigged when the world was zagging. The world said, "You have to go to enterprise—that's where all the money is." We said, "No. We're going to do SMB [small and medium-sized businesses] and rethink this. We're going to make the model work in SMB," even though everyone thought we were wrong. Then we said we're going to go after Salesforce when Salesforce seemed unassailable. Everyone said, "You're crazy—you'll never beat them." We went after them. There are a bunch of points in HubSpot's history where we kind of zigged when everyone else zagged. As Peter Thiel says, "You need to be right about something that a lot of people disagree with."
28:20	Sam Parr	You need to be right about...
28:21	Brian Halligan	Something that everyone thinks you're wrong about. We had a couple of those — not a lot, but a couple of important ones. </FormattedResponse>
28:26	Sam Parr	Did you almost cave at the consensus?
28:28	Brian Halligan	No. We had a real conviction on the SMB thing. It cost us... like, we would raise — we would go raise our rounds; we'd go up and down Sand Hill Road. We had all "nos." The only easy round was the IPO round. Nobody liked the thesis. Nobody bought the SMB thesis. No one else had done it other than Intuit, and we were convicted of it. I think part of the reason we were convicted is both of us had spent our whole lives previously selling to enterprise CIOs, and it's kind of soul-crushing work selling to enterprise CIOs. It was like, "Let's do something a little bit more fulfilling — something that can get us energized in the morning: helping these small businesses grow better." The Salesforce thing: we got a lot of pushback on that, but we didn't feel like we had a choice.
29:13	Sam Parr	You know.
29:14	Brian Halligan	Salesforce was our really good ally, and our pitch was: "Salesforce.com was SFA for sales, and HubSpot was for marketing." For a long time, that worked. Then Salesforce.com one day woke up and said, "We want to be the Salesforce.com marketing." So we were like—either we need to pivot and come after them, or we're eventually just going to be crushed, pushed out, and sold to private equity.
29:36	Sam Parr	"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, was wrong? What did you advise people to avoid, or what attributes should they change about themselves?"
29:57	Brian Halligan	One of the things that I think really worked — and that's actually underrated — is Paul Graham's _Founder Mode_ article. I remember reading that article and thinking that was what I did early; those were my instincts, and I kind... </FormattedResponse>
30:13	Sam Parr	I get talked out of a lot.
30:14	Brian Halligan	I've thought about it over time, and the guy who I think has it right is... back in my day it was Jack Welch. Now it's Jensen Huang. Jensen does this: he's got 60 direct reports. He's tough—like I was—and he gives public feedback. He doesn't give private feedback; all the feedback, positive and negative, is public. And then he does new one-on-ones. I did all of that early in HubSpot, and I sort of got talked out of it. People said, "No, no, no, Brian—mature CEOs do a one-on-one with each manager every week." Then others said, "No, no, no, Brian—you need a staff meeting with just your direct reports. You should only have nine direct reports." And then, "No, no, no, Brian—you should praise publicly and criticize privately." So as time went on I got worn down on that stuff. I watched what Jensen's doing today and I read the founder-mode stuff, and I'm like, I should have stuck with my convictions on some of that stuff. I regret it. I kind of... I got more manager-mode-y as time went on. I regret that.
31:15	Sam Parr	Of the manager mode stuff, what do you think actually works?
31:21	Brian Halligan	I mean, we did — we got our shit together on planning. We were very shoot-from-the-hip for many, many years, and we got a really good planning process down, which is very manager-mode-y. We did bring in some execs from the outside who were very, very good and really up-leveled us. We probably did too much of that. I think a mistake a lot of founders make is they go and hire that "whatever CMO from Microsoft," and they're really proud of it. They do a press release and everyone's excited: we have this amazing CMO. But the CMO gets in the company and they're like, "Where's my secretary? Where's my coffee? Where's my reports? Where's all my stuff?" They're lost in this startup, 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. It's like the Red Sox — I'm a big Red Sox guy — the Red Sox dramatically overvalue players on other teams relative to their own talent. I think every baseball and sports team does this, and every CEO does this.
32:31	Sam Parr	So there's this—I intimately and deeply remember this one phase when we were selling to you guys. Basically, my company was only about 30 people, so it was just me doing the deal. I didn't have an HR team or anything like that. HubSpot had five or six employees, one of whom is now on the board of Asana—these were big shots. And you guys had seven or eight lawyers who were probably making $2 an hour, and then seven or eight KPMG accountants. They were asking me all these questions. They asked two questions that were laughable. The first: they were asking for invoices... no, what were they asking for? They were like, "What's this $50 charge?" I said, "I had some guy on Fiverr do a logo or something." Then they asked, "Did he sign an NDA?" I was like, "Dude, his name was Big Baller Boy 69 on Fiverr—I didn't get him, I'm sorry, I don't know." The second thing they asked was, "What's your five-year plan? Do you have projections?" I said, "Do you guys—my company's like four years old. We do projections quarterly, but shit changes." They were pretty cool about it and said, "Okay, we understand." They were treating this $30,000,000 deal like it was a $3,000,000,000 deal, which is understandable.
33:48	Brian Halligan	It was a weird deal, though. We bought a content company — it's kind of a weird acquisition, I think. When it came up, everyone was like, "What are we doing here?" </FormattedResponse>
33:58	Sam Parr	And they were trying to, you know, make sure that they're doing their diligence and stuff. But I remember thinking, "I don't plan that far out. I'm so sorry. I don't even know if the company's going to exist in two years, let alone what the financials are going to be." That was pretty funny, and it rattled them because the people I was talking to were just hires—they had never founded a company. I remember it kind of rattled them that I didn't plan. I was like, how do you guys not understand that there was a huge distinction between me still being in entrepreneur mode and them being in, like, "I'm only used to this more corporate setting." I thought that was funny.
34:37	Brian Halligan	I think people get too corporate too early. Startups have nothing to lose — literally no assets, no revenue, nothing to lose — and as they get bigger they have more to lose. The lawyers get more involved because they want to cross the t’s and dot the i’s. Startups grow up too fast, the lawyers get too much power too fast, and people start thinking, “Okay, we hit a billion in market cap; we have a lot to lose.” I think the mindset should instead be: how do we get to 100 billion and how do we continue that risk-seeking appetite? Another thing that gets messed up in scale-ups: most companies break at around 150 employees — that’s Dunbar’s number — and all kinds of stuff goes wrong. A director layer shows up, so there’s one more layer between the CEO and the customer, and that messes things up. The people joining are a little more mercenary and a little less missionary, which changes things significantly. Your whole value proposition to an employee shifts. You’re attracting someone who’s more risk-averse at 150 versus at 15, when people are much more risk-seeking. That just bleeds into the whole company. At certain points, only the founders are the people who are risk-seeking, and they end up protecting what they have rather than going to get something new. What’s interesting happening in Silicon Valley — and the CEO of Rippling is doing this very aggressively — is that more and more CEOs are hiring failed founders or doing cheap acqui-hires and populating their companies with founders. Rippling’s got over 100 ex-founders on their team. I think that’s good: it keeps you focused on the long haul and maintains a risk-seeking mindset. You’ve got to keep the risk-seeking up for a long, long time...
36:23	Brian Halligan	Of time.
36:23	Sam Parr	You're so fascinating to me because you're one of the very few people on Earth who's built a company worth tens of billions of dollars, and yet you're this Grateful Dead-loving hippie. You're telling people, "Don't grow up too fast; don't be too corporate." But you're—you're—you're—you're an onion man. There's layers. That's why I—I think you're fascinating.
36:41	Brian Halligan	Let's talk about Jerry Garcia for a second. He's not the first, but one of the first of the very classic Silicon Valley entrepreneurs.
36:53	Sam Parr	"Do you know where the company was founded?" "Yeah. Well, in the house across the street from Ben & Jerry's in Haight-Ashbury." "Right. Was that... it was like?"
37:02	Brian Halligan	It was founded in Palo Alto.
37:04	Sam Parr	Oh, interesting.
37:05	Brian Halligan	It's right down the street from Stanford, and the first concert was in a pizza place in Palo Alto. He's a classic Silicon Valley founder—first-principles, completely first-principles. He didn't care what anyone thought; he was like, "This is the way we're going to go."
37:25	Sam Parr	What way did he say to go, for example?
37:31	Brian Halligan	At the time.
37:32	Sam Parr	Rock and roll was new.
37:33	Brian Halligan	There were lots of rock and roll bands at the time, and there were jazz bands and country bands. When he built his team, his team was very spiky—very Silicon Valley spiky. His bass player was actually an avant-garde trumpet player who learned bass. His keyboard player was actually a blues harmonica guy. His dad was the blues DJ in town. His main singer was the country crooner, and his drummer was like a drum majorette. He brought together this very spiky team and, instead of creating rock and roll, he created a whole new genre called the jam band. Now, Phish and so many other bands copied them. HubSpot did the same thing. 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. If you go to a Rolling Stones concert, let's say in 1980, and you bring in all your equipment—the big camera, your microphone, whatever—you'd try to walk into the concert and they'd say, "Get out of here with all your equipment. This is our IP. This is the Rolling Stones on us." Get out. The Grateful Dead, though—if an idiot like me showed up with his camera and all his recording gear, it would go, "Boom. 'Mic, Brian, come on in. Sit right here up in the front. We've got a taper section for you.'" So people like me would go to Boston, Hartford, New York, Philly, D.C., and record all the concerts. We'd get back home, we'd have the tape-to-tape thing, and from the best concert we'd make 50 copies and then we'd trade. We weren't allowed to sell the tapes—that wasn't part of the culture. We traded the best tapes with all our friends, so you picked up their best stuff and my best stuff.
39:12	Sam Parr	I told you I used to share an office with Nuggs.net — the marketplace where they would trade the tapes.
39:18	Brian Halligan	Right. Then you'd be at, like, a party on campus, and somebody would put on your bootleg. The person next to you would say, "Why is everyone dancing like crazy gypsies? What is this weird gypsy music?" Or they'd hear the Grateful Dead—people shouting, "They were coming, they were coming downtown, come on, tour with us." So the Grateful Dead were the first Silicon Valley viral inbound marketers. He was very first-principles about his music and his marketing. There's a lot more stuff about his marketing that I think is very interesting.
39:47	Sam Parr	"He— I mean, I've been... my parents were Deadheads. They traveled with them, like, you know, show to show. I'm... I'm just googling while you're talking. How old— you said you're 58?"
39:58	Brian Halligan	"Yep. I was — I'm a very young Deadhead."
40:00	Sam Parr	"Dude, this guy looks 30 years older than you, but he died when he was only 52 or 53."
40:06	Brian Halligan	Oh, Garcia. Yeah. Yep. He was—he did not take... he's not like the Silicon Valley people, like Brian Johnson, Peter, Andrew Huberman fan. He—his major food groups were Twinkies, Twinkies, and Twinkies.
40:19	Sam Parr	Yeah, he looks like he parties. "What's the name of the book?"
40:23	Brian Halligan	They called it "Marketing Lessons from the Grateful Dead." Buy it in triplicate — you gotta buy that for your parents.
40:28	Sam Parr	Did you get to meet them when you were writing it?
40:30	Brian Halligan	I met Bob Weir. Yes — I told him, "Here's what we're doing." He said, "I was wondering if anyone would ever write about that. That's pretty cool." That was his reaction.
40:43	Sam Parr	If you Google— I think if you Google your name and Grateful Dead, one of the first things that comes up is that you bought his guitar at an auction.
40:49	Brian Halligan	Yep, I have Jerry Garcia's guitar. I've considered myself the steward of his guitar. It's a very unique instrument — I played it all through the seventies, and I own it. I let it out — John Mayer played it — like everybody and their brothers. Anyone who wants to borrow it can borrow it. But yeah, I enjoy being the steward of a little piece of Jerry Garcia.
41:08	Sam Parr	I love talking to you because I think the world needs more people who have this perfect balance of being like a shark—hard-hitting—but also polite and kind. I think those people are kind of rare, and I aspire to be like that. When I think of all the people I admire, you—and Brian Halligan—are kind of where I want to go in a handful of years. I love talking to you. I hope we can do it in person next time.
41:37	Brian Halligan	Appreciate you, my friend. I want to be like you when I grow up. Alright. </FormattedResponse>
41:44	Sam Parr	God bless. Thank you.

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Should You Start a Company? The Honest Truth

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