HubSpot CTO Dharmesh Shah on empowering entrepreneurs, HubSpot’s journey, and AI automation | E1781

0:00And the truth is, even when you start with an idea that you're super passionate about, in greater than 50 % of chances, you thought you were starting a jazz trio and you made a rock band or a rock band or a rock band or a rock band or a rock band or rock band or rock band or rock band or rock band or rock band or rock band or rock bandwomen success in a lot of ways. Yeah. Well, and waiting for the perfect idea is actually the barrier to finding the perfect idea. Even better. It happens after you start. Once you come into contact with customers, the market, you work together and you start, I love your analogy, as you start playing is when you kind of really discover, kind of discover yourself and what's out there.

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1:22Get 25 % off your subscription or try out the app for free when you sign up now at fitbod.me slash twist. All right, welcome back to the program, everyone. Today we have another amazing guest, one of my favorite people on the pod or just outside the pod. Dharmesh Shah is the co-founder and CTO of HubSpot. He was on the show 10 years ago this year, episode 334. he uh is an incredible supporter of founders angel investors thinker and a friend of the pod welcome back sir thanks for having me glad to be here uh you and i became friends because we share a passion for entrepreneurship and um writing those 25k 50k checks 100k checks into early startups i think we were both in raul's first company were you we were yeah uh rap leaf i think it was called um uh it was called reportive reportive that's right rap leaf was the other one that was doing apis around social media but report of got sold to linkedin and then you and i were the first investors in superhuman and uh it's one of the great things about having a reputation as a supporter of founders early is they always remember yes for their first company and they always have room for you in the next one maybe you could talk about uh we got so much to talk about with ai and hubspot and all the great things going on in the world but i wanted to start just with your what you learned being an angel investor and you know supporting other founders uh in relation to uh building your own company and keeping your own mind sharp yeah um so i'll tell you a quick story of how i got started angel investing in the first place because i was in grad school um at mit here in the boston area and um i just sold my last startup and i had promised my wife i was not going to do any more startups and that's why i went back to grad school it's like, okay, I'll get my master's, maybe get a PhD and go teach.

3:13That was the original plan. And, um, you know, as fate would have it, I think, um, the entrepreneurial genetic flaw is very real. It's hard to stop it just once I was having withdrawal symptoms months into the, um, into selling my last startup. And so I'm like, okay, here's what I'll do. I will start doing angel investing, which I'd never done before. I didn't really know anything about it, um, to live vicariously through other founders. It's like, I don't have to have my own startup, but I can at least participate. It's a little bit like having a niece or a nephew where you get to play with them.

3:42They're fun. It's awesome. But then you hand them back to their parents, then you can go to bed and get some sleep. So that's why I started angel investing early on, you know, in my second year of grad school. And then, you know, ended up starting HubSpot, which I wasn't supposed to start after I met my co founder in grad school, and then just kept up with it. But I have a very kind of atypical style to my investing because I'm a very big believer in focus. And once we started HubSpot, I'm like, okay, well, this angel investing thing is really not going to work because it's kind of hard to do both things.

4:16So I set a bunch of rules up for myself, which is, I'm going to solve for time, which is reduction of time, not money, not return. So I don't meet with founders, I don't take calls, don't sit on boards, don't do all the things that might contribute to increasing the amount of time, no due diligence, try to make my decision in 24 hours. And so kind of kept up that policy, because that was the only mechanism by which I could continue to angel invest and feel like it was not taking away from my, you know, kind of primary activity, which is, as you know, startups can be or should be almost all consuming.

4:50So yeah, I've done I think, not as prolific as you have done a little bit over 100. Now over the over the years, I'm at three, 400, I think, but I have a firm now and what you pointed out, the stack of things that each your time due diligence um and then post investment support and then making decisions on pro rata um and then all of the anxiety that comes with the fact that you know in your child uh you know in kids and grandkids kind of analogy is really apt um and it is the case that the problem child if you have five kids um the child who is a rebel or who gets involved in shenanigans and has trouble at school is the one that takes all your time and then the two or three that are just absolutely gifted and rocking it or the one or two they don't get your time yeah it's a very hard conundrum um that i do not have an answer for because you're kind of judged on your reputation and then the people like all detractors and you know you know from having hubspot and doing marketing your detractors are really important to keep an eye on um because they'll keep you from having future success and you gotta really try to control the number of detractors even if you have a great product somebody has a bad experience in your restaurant you could be three michelin stars but that detractor is gonna destroy you every day of their life until they get their perceived retribution uh it's a really strange thing but talk to me a little bit about where hubspot's at um where it started and where it's at today uh it's been pretty rough road um in terms of the public markets but you seem to have weathered the storm and uh have a very solid product that people feel is um indispensable if i was going to use a word when i talk to startups and you guys are really generous to startups with your startup program uh but it's kind of indispensable i think uh and affordable so talk a little bit about the state of the company today and who are the customers and what do they use the product for primarily?

6:54Sure. So HubSpot is now 17 years old. So it's been a while time flies. They grew up so quickly. And we're about 7 ,000 employees. And as you noted, it's publicly traded, a$25 billion market cap based on which week you look. So and that's, and it's been a, like interesting journey, we can talk about kind of the pre IPO times and going through the IPO process. And our primary offering is we offer a CRM platform. So it consists of marketing, sales, service, software, operations, everything you need to manage your go-to-market and manage your relationship with your customers offered as a pure SaaS product.

7:36One thing that makes HubSpot noteworthy and remarkable is for all of our 17 years, we've been focused on the SMB market. Despite every quarter since our existence, everyone always asks us, including our investors and would-be investors, like, okay, it's fine that you started an SMB, but what's the plan to go into the enterprise? Because that's kind of the natural, I think of this reverse gravity that happens in software where outside of any kind of intervention or pullback, you always get pulled up in the market over time, right? The product gets more powerful. And as you move up market, usually all the numbers that you care about will look better.

8:11Your LTV goes up, the term goes down, all the numbers look better. Average revenue per customer. Yeah. Pick your metric of choice. And usually as you move up market, it gets better. But we very deliberately chose not to allow ourselves to get pulled up and stay focused on SMB, which at the time was relatively controversial and hard to get funding around. It's now gotten better, including HubSpot. There's other companies that have kind of succeeded in SMB. But back then, there were not a whole lot of software companies that had kind of built big global brands, multi billions of dollars of market cap.

8:45focus exclusively on SMB. So that's, Why did you make that decision? What was the reason to go after the wisdom, the collective wisdom at that time? Yeah, a couple of reasons. One is, I've been in enterprise software before. So I've done an enterprise software company. And there are good things about it. But the bad thing is that you have these kind of long extended sales cycles, you have a high degree of influence from your larger customers on the product roadmap and things like that. that. And quite frankly, it's just not that fun. You're serving the fortune 500. And it's kind of very niche.

9:23It's just I didn't find it to be that fun. It's lucrative. At least it was back in the day and probably still is. And so if you look at the other modality, right, so you can have like, serve the fortune 500, or you can build a consumer app, consumer software company. The issue with consumer software companies is that they have very bi-modal outcomes, either you're the next Facebook, the next Google, the next whatever, and you're worth a bazillion dollars or you're nothing at all. It's hard to incrementally build something in the consumer world because often it's subsidized through advertising and things like that.

9:52And the nice thing about SMB is that it has the elements of both. It's got the elements of enterprise software where you can solve a problem and charge money for a product the old-fashioned way and make money that way. But it's got the scale of consumer where there's millions of businesses out there. You don't have revenue concentration. You can control your destiny. So once you sort of figured out how to make the physics and the math work, it's actually a fun kind of business to run and grow. That's kind of part number one. That's the analytical side of me saying this is a reason to be an SMB.

10:22The emotional side of me is we thought there was an underserved market. Both my co-founder and I are kind of champions of small business, hence my kind of startup investment activity. And there are enough companies catering to the Fortune 500. Those folks will always have options. we wanted to create something that helped like in our kind of early version was primarily marketing software, which is, oh, there's this new thing called the internet and every small business should be benefiting from it. And not enough were. So we're like, how do we democratize access to this kind of new technology?

10:53How do we educate? How do we build products that are easy enough to use for people to kind of benefit from this thing called the internet? And we've kind of stuck to that mission for all 17 years, which is, you know, how do we help millions of organizations grow better using the internet and using whatever technology happens to be available at the time. If you're a SaaS or services company that stores customer data in the cloud, then you need to be a SOC 2 compliant, you know that from a third party and you need that third party to close big deals. And if you want to get compliant easier and faster, you need to use Vanta V A N T A Vanta makes it so easy for you to get and renew your SOC 2.

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12:06And tight is right. Lock down those big deals. Here's the best part. Vanta is going to give you$1 ,000 off. That's 10 hundies. Get$1 ,000 off at vanta.com slash twist. That's vanta.com slash twist for$1 ,000 off your SOC 2. It's also a huge blue ocean. People don't want to take on the small players because it's not enough revenue. That's exactly right. If you have a thousand people, a thousand seats or three seats, well, you're going to play for the long ball and try to spend the extra six months to get the thousand seats as opposed to trying to get 333 people to sign up for three seats each. Yes.

12:41But man, if you do make it work, there's nothing like a startup that enables somebody to create a business. Shopify, eBay, Airbnb, Etsy. Yeah. Gosh. Even, you know, to a lesser extent, Uber, DoorDash, like people create, you know, sort of micro businesses. These businesses are just amazing in terms of the amount of creativity, the people who you enable, because then that informs the product, doesn't it? people start using your product in ways that you probably didn't anticipate and they are this incredible focus group you know that's that's the great thing about having these really um you know what's the word you know they're really scrappy yes so they're gonna they're gonna give you some great ideas i'm sure some of the best ideas have come from the customers most um yeah and so hub spot has you know 170 000 plus customers now right and had we been in the enterprise market that would have been more like 1700, right?

13:40Like a multiple hours of magnitude difference. So we get all the better. And it's just a lot of fun because I'm a big believer in terms of product development and fast iterations, short feedback loops, being able to act on things. And when you have thousands of customers, you know, joining every month, you're able to then kind of get that feedback very consistently, get ideas in, kind of iterate on the product. You're not dealing with six month, 12 month sales cycles and figuring out whether something will or will not work. You can run better experiments. Yeah, just lots of positive to it. Once you can make the math work, it's and for all folks in your in the audience listening, if we were having this conversation, let's say 15 years ago, been our early years of HubSpot, you know, I would say, okay, well, you know, it still remains to be seen whether HubSpot is successful or not.

14:26And SMB is hard. So I wouldn't recommend it. Now I would actually recommend it. Because especially as a startup, right, if you look, so in the kind of 90s and 2000s, when I first kind of got started in in software and tech, enterprise software was on a relative basis, relatively easier. But now we've gotten, I'll say like a glut of products, very, very discerning buyers, you don't, it's hard to kind of make money and kind of get things through as it once was in the 90s. And so for a startup, it's like, okay, you're, you're getting out, it's like, if it's going to take you three, six, nine, 12 months to kind of get those early customers, and you're trying to iterate and maybe pivot if you need to.

15:06Doing that in the enterprise market is really hard doing that in SMB is much easier. And one of the reasons that made SMB so hard is they were expensive to get to back then. Yes, it was just hard to reach them. How do you make the kind of knock on the door? I mean, that was traveling sales. You know, that was out there. And literally, that was actually determined. Now that I remember you had inside sales and outside sales and outside sales was knock on doors. And there were so many of them back in the 90s. It's a little no solicitations, please. Do not come in here and sell something. Now that we have Shopify, there's HubSpot, there's ProofPoint.

15:38So even if you're raising money, which we can talk about that, whether the good and bad of venture capital, but I think SMB is still a vibrant market for entrepreneurs to kind of tackle because it's easy to get started. Everyone knows 20 people that are entrepreneurs or small businesses, you know, we're one degree removed. So they're not some sitting in some ivory tower that you're going to spend six months just trying to get a meeting with the the decision maker the decision maker is usually the founder ceo and it's um it's much easier it's much much more fun business so yeah i suppose the small businesses too do not have cycles to waste so you can get to a very quick decision i need this i don't need this i don't have time for this whereas if you go to a big company and i worked at a big company for like a minute or two aol and sony uh selling one company and then starting my career and last a year at each um there would be meetings and committees and there were middle managers who i realized all they did was go to meetings all day and i was like what what do you do and i go to meetings and i don't know you saw toby's awesome at shopify's awesome calculator this week this meeting cost two thousand dollars yeah that was awesome they should put that meeting on whoever uh sets up the meeting it should be billed to their department they should get the bill for that you know if you're going to pull in six developers for$200 an hour or whatever they cost, she gets a bill for it.

17:02It's not just that they're having kind of meetings and they have these committees, they have this, like you need just one relatively influential person in the company that's going to say no, that can veto that pop, you know, that potential deal for whatever, whatever reason, right? It could be, you know, stay in the market. And so you're just kind of jumping through these, you know, 12 flaming hoops, hoping that, okay, I got through this committee, I got this person to approve it. I've got my champion doing this, whatever. And then ultimately, maybe you get a sale six, 12 months in. Whereas in the small business world, it's like you've got one person who's generally an optimist.

17:33They're an entrepreneur. They took a risk. They're used to that. You don't have people whose entire job or most of their job is saying no to things, right? That's not which in the enterprise world you get all the time. Let's widen the discussion here. What is your advice to founders or potential founders, not people who have done it before, but people who haven't? we have massive layoffs in tech um i don't have here in my notes if you did a riff but i'm assuming you probably did if you were part of the uh over hiring trend we were all hiring for explosive growth we'd be interested to hear your thoughts on the lessons there but putting that aside a lot of people had jobs at uber or google or microsoft suddenly find themselves with a decade of experience and two or three friends who uh were getting paid ginormous salaries huge options and now they don't have four offers uh competing for their services they got zero yep so some of them are looking on huh these offers aren't great maybe i should start a company best reason to start a company who should start a company why should they start a company so i think two reasons to start a company i don't think uh that should be one of them i mean if you were already considering it uh that can be one of the factors this is okay well my opportunity cost was too high i've had good ideas but the two reasons to start is you've got a passion for a particular kind of problem that you want to solve in the world, you know, for whatever, you know, set of customers, or you've got a set of people that you know that you'd love to work with and do something with, right?

19:02And HubSpot actually falls in the latter camp. HubSpot, we had, we had not actually decided on what the final idea was going to be until after we started the company. The first decision we made was that Brian, I, my co-founder and I, we're actually going to start something. And it's like we were loosely, we were looking at several ideas. One was going to be like an Oracle for SMBs, like an ERP kind of thing. We've looked at marketing. And so my advice to founders here would be like on the idea front, I'll give you my kind of quick framework for, we'll talk about the idea and we can talk about kind of founder selection.

19:36On the idea front, one of the mistakes I think would-be entrepreneurs make is they assume that in order to kind of take the leap of faith and start a startup, they have to have this really great, perfect idea. And I don't think that's true. And even if you happen to have a really great, near perfect idea, you wouldn't know it a priori at the time. Until you start a company, the greatness of the idea does not really reveal itself. And often, if you study startup history, a lot of the success stories that we've seen actually became successful for an idea that was not the original founding idea. right they kind of pivoted along the way and something very different happened over over time either a full-on pivot or at least incrementally the company looks very different from the early idea so the corollary here would be is like okay well if most successful startups end up with an idea that was not the original idea then how much does that original idea matter should that preclude you um from from starting okay so that's kind of a very important insight i think for founders to understand because as you said hey if you got three people you like to play music with then just start playing music start the band you know you're gonna love it and the truth is even when you start with an idea that you're super passionate about in greater than 50 of chances you thought you were starting a jazz trio and you made a you know and uh you know uh you know a rock band or a southern rock band whatever it is you'll you'll find your sound and you'll find it by doing it you have to play the music and so waiting for the perfect idea is the enemy of success in a lot of ways.

21:09Yeah. Well, and waiting for the perfect idea is actually the barrier to finding the perfect idea. And even better happens after you start, once you come into contact with customers, the market, you work together, and you start, I love your analogy, as you start playing is when you kind of really discover, kind of discover yourself and what's what's out there. So let's, let's talk a little bit, I think about, you know, ways I use to kind of assess an idea. And I think in frameworks a little bit. So there's, I think, three things to look at. And there's a common mistake that happens. One is the potential that particular idea has.

21:42So let's say everything goes your way. It's like everything works. It's like you execute and things happen. What could this potentially be? What's the overall potential magnitude of the outcome here? And there's no right or wrong answer based on if this is your third startup versus your first one, things vary. But that's thing number one is what's the overall potential. The second thing is, what's the probability of success of achieving that potential? How hard is this to actually execute on and get to the actual potential? The mistake I think entrepreneurs make is they start with the probability question, what are the likelihood of me pulling this off?

22:18And if that's too low, they never even think about the potential. And you play poker and are into stats and kinds of things. For instance, if you have a 10 % chance at a billion dollar outcome, The expected value of that is 10 % of$1 billion. It's worth$100 million. Just putting everything else on the side, all things being equal. If you have a 50 % chance at a million-dollar outcome, yes, you have 50 % chance at a million. That's worth$500 ,000, worth far less. Now, obviously, a lot of it has to do with what you can put at risk and all those things. But all things being equal, just putting an idea aside simply because the probability is too low is short-sighted.

22:55You should also look at, number one, what's the potential? And the last thing is, to what degree do you have passion or proximity to this idea? Don't just pick it based on those numbers to say, oh, I really have a passion for solving this problem, or I've been working in this particular area for a long time, I've got what I call proximity. So a combination of those three things helps you pick amongst the ideas that you might pursue. Look at the right mix of, okay, here's something I'm passionate about that's got decent potential and is a level of risk in terms of the probability that I'm willing to accept.

23:26And then you kind of pursue it. All right, we all know the one thing that separates great startups from the good ones is product velocity. What does it mean product velocity? Fancy term, right? Here you got your product and your velocity speed, the speed in which your product improves. So can you ship updates? Can you release new features? Can you do bug fixes? Can you iterate on the interface? Can you solve problems for your customers? And can you do it quickly? Because you're not alone, You have competitors and your customers have choices. They may solve their problems by writing their own custom code, or they might use your solution.

24:02This is what startups are about. How fast can you get that product velocity going? And so, you know, how do you supercharge it? Everybody says, okay, yeah, we want to go faster, but you got to go faster intelligently. And Crowdbotics is going to help you do that. They're your CTO as a service. Basically, they provide you with the most optimal architecture to get your product to market as fast as possible. You'll have access to an on-demand product manager and developer talent, and they will help get your app into production 10 times faster than conventional development. Crowdbotics can work with your in-house dev team, or you can just have them work independently.

24:34And you own all the IP. You own all the source code. Let the folks at Crowdbotics supercharge your product velocity today. No more waiting. Get a free build plan at crowdbotics.com. That's a$4.99 value just for the Twist listeners. You get that for free. That's C-R-O-W-D-B-O-T-I-C-S dot com slash twist for a free build plan. It's such a great framework. I think one of the things I've seen over and over again is people will pitch me what is essentially a service business, you know, maybe in a wrapper with a little bit of software or software enabled services, whatever. and if you think about the expected value something we talk about in poker um if i do call this bet and i or and i do hit it on the river or i do hit my magic card on the turn do i get that person's whole stack do i get three people's whole stack is everybody going to come in you really have to think about that and what i tell founders uh you know which is largely based on your framework here is you're going to put in 60 70 80 hours a week for your startup it's just the nature of it it's going to be all encompassing if you're an entrepreneur you're going to put everything you got into it if you put everything you have into a service business you're going to get it to 10 million dollars a year in revenue if you put everything you got you know into a software business or a marketplace uh or a fintech company and you know pick a platform company you know the the potential revenue is billions of dollars and there's just a natural cap to some businesses you pick d to c it's going to be a low margin grind yeah sure you get a bow and branch once in a while or an eight sleep there there are outliers that can do it but man it's hard and then i love yours passion and proximity to the idea.

26:10Yeah. The other thing is, especially if you're early in your entrepreneurial career, let's say you're doing your first one. The other reason to lean a little bit more towards potential for the idea is that you want several, if you can, several steps up to bat. So you may not get it exactly right the first time, right? But if you do a service business, you're sort of in there for the grind, you're going to be there for 5, 10, 15, 20 years. And that's sort of going to be it. It's not going to probably die, right? It's going to make revenue. You'll have a comfortable living, but it's unlikely you're going to have this kind of breakout success, which is okay.

26:41There's nothing wrong with that. But, you know, if you really feel like this kind of entrepreneurial drive to kind of take your swinging bat and swing for the fences, you're better off doing a product-oriented company. And as it turns out, in my experience, and this is a little bit paradoxical, it's often easier to pursue a larger idea than a smaller one. And the reason is that a larger idea will attract better people that are more ambitious, that will kind of thrive on that challenge. Like, oh, we're going to do this thing that's really, really hard. That's the way to get people into the company that will help you increase the odds of your success.

27:18Whereas if you're going at a, oh, we have a high potential. It's like a 70%. We're going to all make money here. It's going to be$1 million,$5 million, whatever it is. That's fine. But you're going to find other people that are kind of mitigating risk a little bit too early. so if you're kind of an entrepreneur career you know as much as you're kind of willing to stomach uh nice i'd say take your shot right like in this of course you you i mean and when you get to our age you and i uh got the gray hairs coming in uh you realize more and more that the finite commodity in the world is time and you have a certain amount of time to get this done and to just build off of our you know jam band uh analogy here you know if you say hey i'm i'm looking for some studio musicians to play backup at the studio and i'm going to open a studio and we're going to do backup musician you're going to get a certain type of person a conservative person who wants a steady salary if you say hey i want to i want to build the largest rock and roll band in the world and go on tour and do stadiums and have the number one hits you're going to get people who are like yeah let's do it and one group of people is going to write their own music and wants to write their own songs and own the ip and go big and the other group wants to punch a clock and get out of there on time and you know the more i look at it i feel like there are people in the world who are wired for either group and a lot of the tension in our society that we see the anti-capitalist kind of underpinnings that we see in the united states today or clearly in europe or wealth disparity a lot of it has to do with this live to work work to live or my life is my work and this disconnect that people just don't understand that for entrepreneurs there is no other way they have to be building something they have to be the person playing lead guitar, they have to be the lead singer, they can't play any other role.

29:04You think that's right? Do you think like, there's just different people in the world? Yeah, this is, it's not a popular opinion, but I'll put it out there. Anyway, you know, HubSpot has 7000 people. And we have the entire broad spectrum of people at various stages of life, various temperaments, which is great. Well, that's one of the values to scale is that we can kind of support whichever modality you have. So there are people that are kind of like, I want, you know, more balance in my life, I want this, I want, and that's fine. I think that's totally okay. Where start things start to not be okay, is when you pick a particular mode, that is incongruous with what your expectations are.

29:43So let me give an example. In every competitive endeavor that humans will ever undertake, there's always sacrifice to be in the kind of top 1%, top 0.1 % as far as outcomes, right? If you're in the Olympics, you don't say, you know what, I was born with this talent, I can really run fast or jump high or whatever. And so I don't really have to work all that hard, because I've got all this talent, no one shows up for the Olympics without sacrifice without having getting to that point. And even then continuing to do that as an Olympic athlete, same for music, same for any competitive endeavor, right, where you're trying to be in this kind of small, small percentage of outliers.

30:17And not everyone necessarily needs to do that. But it's like, if you're expecting the outcome of one of those outliers, but you're not willing to make that sacrifice, that's when conflict starts to occur. It's like, okay, well, you know, it's fine to pick one path or the other. But you can't say, well, you know, I want hundreds of 1000s of adoring fans. But also, I really don't want to practice, you know, five times a week or seven times a week. I don't want to be famous. I want to have 80 ,000 people pay$200 a ticket for my show. I'm Taylor Swift. I want to go on a tour. But I don't want people to ask for a selfie.

30:47It's like, you're gonna get asked for a selfie. you know what to her credit she does that fan service but there are people who are like they want it they don't want it mark knoffler from dire straits man they when they hit the peak and they were the largest tour uh in the world they had two different sets and this is when he said when you own your own stage that's when you know it's gotten too far and they owned two stages and in san paulo in brazil and then in venezuela argentina mexico you know southern california the stages were moving while they were playing three nights at the next place and they were doing 250 gigs a year they were printing money but he said it was now a beast and he just disbanded dire dire straits at the peak to become you know a folk singer basically and he did his solo albums and i still love him for both eras miss dire straits but i think you do need to know it's like the it's the it's the absolute perfect example if you if your expectations are set right and at a big company you need people um who are steady and long term and you don't need them to come in every weekend go go if you're the sales team and you hit your numbers god bless spend time with your kids if you got to leave at 4 35 30 pick up your kids that's that's great but in my when you were a 19 person hub spot i guarantee you people were there at 10 o 'clock at night on the weekends yeah yeah yes and and one one thing to be clear on is that you know i'm not like a big fan of kind of the aggressive hustle, hustle culture, right?