David Cancel: Leading A High-Growth Company

David Cancel is a 5x founder and 2x CEO with four successful exits to date. Currently, he’s co-founder and CEO of Drift, a startup that’s making it easier for businesses to talk to their customers. Previously, he was at HubSpot as Chief Product Officer after they acquired his company Performable.

In this (fireless) Fireside chat, we delve into what inspires and motivates David, how he came to start five different companies, and how he leads a high-growth company. Plus there are some great questions asked by the audience at the end that helps David open up about what he has done and what’s next.

Transcript

ML: Right. So, pretend there’s a nice fire behind us. I’m going to ask David a few things and if you would like to ask questions as well, please either stick your hand up at appropriate points – so I have the mikes in the room all the time. Or you couldn’t tweet over. But I’ll just start off by saying welcome back David. You’ve spoken a couple of times before; you’ve been on lots of other occasions as well. Give us the 30 second elevator pitch on Drift

DC: Drift basically helps B2B businesses connect with the customers that are interested in buying now that are on their website.

ML: Describe David Cancel

DC: In 30 seconds? Originally software engineer, long time ago no one on my team believes that anymore that I ever coded and then have started five companies and Drift is the fifth.

ML: Fantastic. Okay. What was the first company?

DC: the first company was called Compete. I was part of several other startups before that but in 2000 I started company here in Boston called compete.com and it’s like if you know Alexa which is sort of related to Alexa so we would help people figure out how they were doing relative to competitors using internet data, but the thing that we got wrong in 2000 was timing matters and in 2000 post bubble 2001 which is when we started the company. No one really cared about the Internet right from a commercial standpoint, and so I have a lot of good stories now that are funny but they weren’t funny at the time; including you know getting kicked out of many company when we were trying to sell can compete services into its software into it. And if quotes like no one will ever put a credit card online no one will ever buy anything but books online. Well you know like I lost my bleeping 401K stock to Yahoo’s stock but et cetera et cetera we’re shutting down e-commerce. E-commerce is dead. Department like all of these things make for nice stories now. They didn’t feel good for the first almost three years Compete, and we sold Compete in 2007 to a company WPP a London based giant.

ML: Yeah, who are having a few issues.

DC: Yes.

ML: Right, now let’s share some other stories. Few things that I want to talk about with you today I think sort of motivation. What you what are your thoughts on products. What …Have you evolved as an entrepreneur over the years? I think one of the things that we’ve heard today from a lot of the speakers is some very kind of honest and open and sort of self-reflective truth. So we’ve been kind of talking about the sub you started off as a product guy?

DC: Yeah an engineer, software engineer and then yes. It’s a long story. So I started off as a software engineer in college I studied computer science and accounting and then I interned one summer for an accounting firm and for about 30 seconds in I was like I never want to do this ever. And I only took accounting because my parents both emigrated to the US and my mom’s only dream for me – which I never fulfilled – was to be an accountant and to wear a suit and to go to city wearing a suit and a briefcase and I’m pretty sure my parents did not know what an accountant did but it looked like a stable job.

But I was kind of obsessed with the early Internet and that was like in the early to mid 90s. And I stopped going all my classes in college and just hung out in the library because that was the only place where we had access to the Internet and an early version of mosaic and then later Netscape. And so I just stopped doing everything else because I basically found a rabbit hole that I’ve never come out of. It just kept going deeper and deeper and deeper. Both my parents work for themselves I wanted to start a business I didn’t know what that meant at all. And it’s hard to explain this to people now who for us that grew up precommercial Internet like I had no idea what a business meant entrepreneurism I felt like nobody was like a four letter word until like the mid 2000s like post Zuckerberg era. Entrepreneur meant like you know I don’t know what I’m in, I’m in something bad like you sold the infomercials or something at least what I had heard and I didn’t really know any of that. But I joined a startup – which I didn’t know what a startup was either – in 1996 and then started to build something and that got me really interested in what I do now. And so I kind of taught myself how to how to code how to do everything. I like that pirate aspect of the early Internet. And then I think one of my people like asked me not about how did I start/How do you start companies and I said like I don’t know; one of my advantages was that nobody ever expected anything of me like. And so like my parents I never went to college like they didn’t know anyone who started a business like the way that we’re thinking about like my dad. I remember I came home one day I think I was in high school maybe starting college and my dad had given had brought home an application – I lived in New York City – for the New York City Department of Sanitation because he thought that would be a good job for me. And then my mom cried for two days and said he would never do that. And so like the reason I mentioned that is that because I didn’t actually have any expectations of what was going to happen. So in other words I had nothing to lose and when I started a company I had nothing to lose. What about if it didn’t work so then I could be an overpaid software engineer like so I mean it didn’t actually matter. And so I had very little risk compared to a lot of people that I talked to today where entrepreneurism is in vogue. I want to start companies and they almost to me they seem too logical about it. And they have a lot to risk. They have a big you know a huge education behind them, huge set of expectations from their parents, huge set of expectations from society. They have a lot to lose and I kind of talk them out of doing this thing for crazy people because I think like starting a business is excusable if you do it one time and cause you didn’t know you were naive.

The second time it’s kind of questionable by the third or fourth time that you start a business like you probably there’s something going on. And by the fifth time you’re certifiable at this point. Like starting businesses cause when you go through it is. I was just talking earlier to some people about and I think like we romanticize the pre-product market fit phase and I’ve talked a lot about that in the past like the early days a lean startup sort of agrees and stuff I used to give talks and I gave when I hear about that and a long time ago and people romanticize that part but having gone through that with Drift in the first two years I never want to go back to that. Because it was a constant you know kind of constantly going I have a co-founder the two of us we can’t say look at ourselves every day and say like why did we do this right. Because we left a company where we were we just went public as a company the company is called Hubspot and Dharmesh has spoken here many times and we were working with Dharmesh and he left that to go start a company again. And pre product market fit you’re like just the only way I describe it it’s like it’s almost like walking through the desert every day with no reference points and every day you think to yourself Did I am I closer to getting out or did I just go deeper in the desert because I have yet to have reference points and then at the beginning when you hit product market fit at least you can see the giant Himalayans in front of you. But at least you can see something. And for a long time for that first year and a half we could see nothing we were just wandering around aimlessly trying to figure stuff out.

ML: So Drift aside which of your four startup are you most proud of.

DC: Probably one that’s not even officially a start up but I started a nice thing called ghost story and which is a browser plugin privacy browser plugin and I started that in 2008. I want to say something like that and I’m most proud of it because I never thought it was a business on purpose, I thought this cannot be commercialized. I only created it because I was interested in something geeky which was trying to see what things were tracking you online and so I created it. And then a friend in San Francisco was equally geeky and he asked me to post it so that he can install and the easiest way to put it in the Mozilla add on store inside extension store. So I put it in there and then like in the first year there was like 3 million people using it but it was and now there’s I don’t know for Mozilla owns and now it’s like 40 million or something like that people use it but like and most people will like remember that that thing.

ML: And was there a monetization?

DC: No I could’ve. Like in retrospect there were lots of ways to do it but when I was doing it I was always like this is not a real business like this you know. So it was always like and I finally I sold it in before I started Performable like 2010 and because I never thought it was a business. And but obviously it could have been massive.

ML: So I think one of the things that comes across from you is that you were very very people think of you as a product. And you were running What was that thing HubSpot bought?

DC: Performable

ML: that’s kind of weird moving from running you’re thing, something that people have been talking a little bit about. And today you’ll land on somebody else’s rocket ship.

DC: Yeah. Yeah it was. It was fantastic is an awesome experience. But you know in 2009 we started performing two thousand like 18 months later. We were acquired by Hubspot and that was it was great. You know HubSpot was probably the size that Drift is now like two hundred and some odd people and growing really quickly. I never thought I would sell the company and I had one investor and they definitely didn’t want to sell the company but I thought you know I had known Dharmesh who’s the CTO and founder of HubSpot for a little bit just like virtually because of Compete and because he’s interested in some data Compete and then I knew all a lot of the people that were involved in the company and we thought we had this crazy idea at that time that perform like we were a product people and HubSpot was super strong on marketing and sales and services and everything else. And so like if we were together and maybe we could build like this big company. Which now obviously happened but like at the time seem crazy. And so that was really the driving force behind it. And it was an incredible experience. Like we went from like 250 or 200 people when I was there to like I don’ t know 1300 when I left something like that pretty quickly and like three and a half years yeah it was nuts.

ML: But it’s interesting because you left pre IPO.

DC: Yeah the day before that I left. Actually, today marks the anniversary of Drift. Four years ago we left and today.

ML: Happy Birthday!

DC: Thank you

ML: [singing] Happy birthday to you…

DC: And it was the four year anniversary I left we left September 30th 2014 and HubSpot went public. Sometime in the first two weeks of October. This month. Yeah.
ML: Did you feel like if you stay that when it’s public you’re going to be tied in there for a little bit or ….

DC: Yes, I’m probably as crazy as everyone else is here who has started businesses and so you know it was a decision borne for me of like I had an amazing amazing friends and an amazing company and everything could not be better. But if I stayed then I had to commit for another two years let’s say. And I don’t know I think most entrepreneurs are commitment phobic. Yes very. So I was nervous about that. And then I’ve really only started companies as a byproduct of I have an obsessive personality and I channel that in a positive area which is like I’m obsessed with learning and getting better. And the next set of things that I felt like I wanted to learn were back at this stage of the business and so that was the driving thing a little bit was this commitmentphobia but it was really like I want to learn again. And I was learning lots of things there. But I was not the set of things that I wanted to learn next. And that was really it. And then my co-founder at Drift who’s V.P. of engineering for me over at HubSpot came along and we started this company the next day. Yeah. You should probably take time off between these things.

ML: So you knew what you were going to be doing.

DC: No not at all. Zero.

ML: Really.

DC: Yeah. That’s why we started at the end of ‘14 and we didn’t launch our product commercially until April of 2016. Yeah. No we didn’t. I mean we had like the story of Drift is like I had things and this is kind of my migration as a product founder in the early days I used to think – in the first several companies – that everything was product and so like 99% of the stuff to focus on everyday was about the product and engineering and building the thing and then a little bit about the go to market and selling that thing and marketing the thing. But it was really around. How do you build this thing

ML: and then people will come.

DC: Yeah. They will all come somehow and I but I do think in that era it was a little bit more true than it is today because in that era like a lot of the things that these fellow early other Internet pirates were building at that point like it was most people didn’t know how to build them yet there was in you know a book on it. There was no Stack Exchange. There was no Google. There was no way to find this thing. So the fact that you could build it was novel enough and now fast forward to where we are now. When I started Drift like everybody knows everything about building, scaling, doing all that stuff it’s all easy easily accessible hard to apply. And so very hard to apply. And so in the beginning I used to care 99% of a product and all that stuff. When I started Drift by the time I started Drift I had gone 180 and thought like well it’s 99$ people. That’s the hard stuff. I wish it was just the other stuff because that’s that would be a lot easier. It’s 99% people and it’s like 1% all that other stuff that I worried about the most. And those people are the people that you work with. But it’s also the people that you serve in terms of customers, if you happen to have investors, if you can your greater community those things are complicated – as we all know – those are very complicated dealing with people is very complicated dealing with bits which I did for a long time that’s complicated but less so. You know that was fun times and so by the time I sort of Drift to fast forward I was obsessed about some trends that were happening; one of them was messaging.

Basically the fact that messaging from a technology standpoint I say hasn’t changed in my career. No one can argue about that all day long fellow product people not really. IRC (internet relay chat) is not that different from Slack today and in some ways you can line them up and they’re almost like Pixel for pixel the same and messaging on your phone looks a lot like instant messaging did twenty five years ago almost exactly the same. What has changed is that we’ve gone from like millions of people using it when I first started use it to like by the time Skype was massive 150 million people using around the world to now multi billions of people using it. That’s the difference. And like identifying that behavior change and saying like oh we’re at scale now maybe we can use messaging in the same way a slack or WhatsApp or whoever to kind of resegment or rethink a problem space like let’s do that. And that’s all we knew in terms of Drift and then we knew some other things like wow like the consumerization of the enterprise that we’ve all talked about for like twelve years is finally true meaning like we all actually all buy stuff within our companies. It’s not just one person or two or three that’s huge because all of a sudden you drag along the way that you your consumer preferences to work. And so we’ve all lived through that. And then like this huge commoditization of software and hardware frankly where everything that we can create can be replicated like in a nanosecond. And that means that all of a sudden we think that the shift is happening where the power is going to all of us the consumers and the buyers and less so to the companies. Obviously they’re still monopolies all over the place but like it’s shifting pretty fast when all of a sudden you’re in a category where there might be 10, 100, 1000 competitors in where you know years ago you might have had three competitors in that market.

ML: Yeah that’s interesting. I suppose one of the things I’ve noticed over the years with certainly since Drift you’ve been much more vocal about growth and scale. And I mean you used to tweet obsessively about products. And you got a lot more obsessed or not obsessive but in a lot more of your tweeting is about growth and you know your user event which you’ve just done two of not yet holds two in the same month. Never again. It’s called hyper growth. And everything is about that thing. Yeah. How did you get your head round. That was kind of a conscious thing. Or is that something that’s evolved?

DC: Because yeah it’s different from obsessive where I’m product. I still obsess around product and that’s where I’m most comfortable. Product design and engineering in terms of growth, I think what has fuelled a lot of it has to do with these kind of these the shift that I think specifically in SaaS that I live through, in 2000 when I start to compete that was actually a SaaS product. We never ended up selling it as SaaS as a category or thing a concept that exists. I think we called it like we were going to sell software via e-commerce you know and you could subscribe and we couldn’t even describe what it was. We had to go back and disguise what it was because no one would buy, We couldn’t find people to buy or care about our software at that point. But so I’ve been in SaaS this whole time right. And since 2000 would I think I think SaaS has been through these three phases as I think about it which is this first phase when I started compete which was like and you know Salesforce and all these companies had start at that point and you could develop a moat around technology the fact that you could take something that used to be on Prem or some kind of service and then put it in the cloud, make it accessible to people like there was technology moats that we were building at that point around that all those companies and you’d have single digit number of competitors and a lot of them would be like on-Prem software versus what you were offering. And and so that world we could hide behind patents, and secrets, and you know like technology and all that kind of stuff.

Then we went into the second phase of SaaS which you know we were with Performable or in Hubspot and what have you. And you saw the rise of all these SaaS companies I think that second phase was more like the Model T phase – Basically your defence ability most companies were building was around like the business process, kind of technology was equalised a little bit and all of a sudden was like ‘What’s your go to market’, ‘what’s your LTV (life time value) to CAC (Customer acquisition cost)?’, ‘What’s your ACV (average customer value)?’, ‘do you use field sales? Online sales? A mixture of both?’, ‘Do you have. So you have field, inside, BDRs (business development representatives), ADRs (account development reps), CSMs (customer service Managers), etc all these acronyms that we all know. Like all of these things and how do you line them up? And are you vertical SaaS or a horizontal SaaS? And we chopped up the market that way and many companies went to market that way. I think we’re to go back to answer your question I think we’re in this third phase and I think this third phase you have infinite number of competitors in your segment and you can’t hide behind just the business process, nor the technology. So I think in this phase you have to build a brand. And so I started to – I’m not a marketer – I started to obsess. I’ve become one but I was a I’m not naturally one but I’ve been I started studying a lot of it gone back in time and studying a lot of stuff and saying like how did those companies build a brand. Like what does a brand mean? I don’t know. I came from being an engineer and a product guy. And so I started to study how did people make decisions when they buy, what is the psychology behind all this stuff and just really got deep into that stuff and thought like okay if we’re going to build a company the kind of company that we’re trying to build like we’re going to have to make it accessible to a global set of customers and we have to create this brand and all this stuff and so that is where that kind of idea of growth came around because all of a sudden we wanted to play on a global stage versus in this small segment or region

ML: So one of the things I was thinking about when we’re when we were talking about this was working somewhere like HubSpot. It’s become a marketing company and I think you know you are talking about being the next Boston pillar company which is an interesting thing. Is that something that you would have seen yourself doing five years before HubSpot or was this?

DC: No not at all.

ML: Was this something motivating you?

DC: I feel like I don’t know incrementalistic maybe is the wrong word. But like that I’m obsessed with learning. I keep learning part of learning is having access to different role models different mentors and then being able to look behind the curtain and say oh that’s how they do it right. And so at least for my version of learning and so I think part of the way Hubspot is shaped this is like I got to see like oh I never had seen like what does it take to go from like 200 people to this public company. Doesn’t mean that you can do it but like what are the mechanics how does it work. How do you like decompose this thing. And so I saw that and then I thought wrongly or rightly like oh maybe we can do that right in the next company. And so I’ve been kind of like learning kind of these step functions along the way of like different scale and operating in different scale and so I definitely would never have thought about it before Hubspot and also beyond HubSpot I thought hey this is my I started four companies already like why am I going to get up? What’s going to motivate me every day. Like do I want to go just start another company and then sell another company eventually like I don’t know that and feel like it would motivate me. But like maybe if we could serve our customers and eventually build this type of company like maybe that would be motivating. So, all of these things I think it’s a complicated answer. But I learned by observing how people have been able to do things

ML: And does the sort of emergence of I mean people talk about unicorns which I think are nonsense. I think rhinoceroses, ugly beautiful unicorns. You know actually exists and they’re quite rare. But you have things like HubSpot which is probably three, four, five billion dollar. Yeah. Is that the sort of thing that makes you go actually 50 million isn’t enough?

DC: No, I don’t actually. No, not for me because part of like I don’t actually.

ML: That’s the money in your pocket. It sort of does that change the measure of ambition?

DC: a little bit. I’d say you know part of my motivation for myself I won’t speak for my co-founder but similar is like I thought look if we’re going to start we’ve been super fortunate we start Drift if we ever have been able to build this kind of company. Like my goal from the very beginning is like 100% of my equity in Drift. I will give away. Like 100% I’m not keeping a dollar of it. So like a dollar of it is not motivating. So it’s not the 1% pledge with me it’s a 100% pledge. So that motivates me. Yeah. Like can we create enough value and have that.

ML: So let’s talk a little bit about your giving you equity; where’s the queue? Where’s the line?

DC: Yeah.

ML: Is that something that you’ve articulated yet?

DC: Internally. But I don’t talk about it publicly often, except for here.

ML: It’s a special place

DC: Yeah, a special place. Yeah. Internally sometimes I talk about it and yeah I mean I think for me there’s certain, obviously we do that now, that gets me up in the morning. And they’re specific causes that get me up – my co-founders from Nicaragua he immigrated here and he wants to build schools in Nicaragua and that’s his cause. And so we don’t trumpet that around but that’s what gets us up.

ML: So are there particular things that you would like to see happen with that?

DC: Yeah absolutely. So for me learning is a big part of it, so helping you know in different formats which we try to now like kids under a certain age because I think that’s when we really have a chance and like some of the bigger issues that we try to deal with now I kind of think like the unfortunate answer to a lot of them is like they’re like multigenerational answers right. And they would put everyone wants like a shortcut to it and it’s gonna take a long time and so I’d like to support that. And you know my mom basically raised me alone and so I’d like to support single moms. And those are two things that I’m focused on.

ML: Fascinating. So how does that then tally with someone we can we can talk about we should talk about when you have a growth minds when you have a team that is rapidly expanding you’ve got a lot of venture capital coming in to fuel that growth that requires quite a commitment not just from you but yet from the entire employees and the entire team of people that have gone to Drift. Absolutely love it. It. But they’re very they’re very committed. And it feels like it’s one of those things where everyone is on that mission.

DC: Yeah I think you know we’ve been super deliberate on that side of like talking about one quarter all of us there even at this early size is like that we’re all obsessed with learning. Right. So one of my issues is that that I only really like to be around interesting people that want to learn things and that I’m not very good at being around people who are not like that. Which is unfortunate so makes it good for this kind of environment like with everyone in this crowd and then starting companies that’s like an interesting trait to have. It’s not a good trait to have in the rest of your life because you don’t encounter a lot of people like that. And so we wanted to design, I wanted to design a company where like everyone was had this kind of mindset they wanted to learn and in order to learn one of the things that we talked about the most is that the hardest thing that’ll keep you from learning is your own internal battle which we all have every day between your own ego and balancing a level of humility.

And that is a painful thing. That’s an easy thing to talk about and it’s a hard thing to deal with every day. And so those are the two things that we really talk about with everyone on the team and so the team is very, it’s very diverse, very different but I think we’re the same and these two qualities of having this learning obsession or mindset and then having this second thing I’ve like always trying to figure out like that this level of humility and that we are here to serve customers and that we’re not a software company and we’re not a whatever company and like we are a customer service company and we’re only here to serve customers and the minute that we stop doing that we will not have a business anymore. And that’s again a super easy thing to talk about which you can talk about that and put stickers on the wall and do all that stuff. It’s hard to live it every day and live values and I think you know I talk about values for a reason like I talk about values a lot. And like and I think like you know my view on that kind of stuff is like I think that culture is like the sum of the people at any given time in your company and then the things that you want to preserve and that you are willing to promote, but that you’re also willing to part ways with people if they violate those. And everyone will promote and everyone will talk about the values but almost no one will ever make the hard calls because that’s a talented engineer. That’s a great salesperson that’s very marketer whatever will look the other way. No one will ever do that and that you have to live every single day and that is the that that becomes your values the minute that you turn away and don’t look at that then that was the value of the company.

ML: I mean it’s always been very clear to people that know you, you have obsessive values that you hold close. Let’s talk about Hypergrowth East And what happened. Because I mean if I’m looking at that from the outside and ask you to kind of elaborate say what shape you know what your sense of what was going on was is you kind of have a culture that is growing and you have people kind of coming in. It’s harder and harder to control.

DC: Very hard.

ML: And then suddenly something gets out of control. You want to just give us a little background on that?

DC: Sure. So we had this are we have a conference called Hypergrowth. This was the second year that we’ve that we held the conference. Last year we held it in Boston this year we held hypergrowth east in Boston last month and it’s officially a month ago. And then we held another conference called hypergrowth West creatively in San Francisco and had hyper growth this week. It was big. We had 4,500 people registering like three thousand people show up and it was kind of in this outdoor thing we had a bunch of speakers come and kind of like my thing with the idea for hyper growth was that I never wanted it to be a Drift conference or to talk about marketing and sales or that kind of stuff that we do because I just think that’s boring. And even to me – having done it one time I wanted it to be more like this like this kind of conference. And but to have what label for you. Yeah right. OK. So I wanted it to be speakers from all sorts of areas because I think like when we talk about growth we think like we don’t separate or I don’t separate professional growth from personal growth and personal growth being emotional growth and physical growth. And, you know, growing and all these different dimensions I think you need to grow in all these dimensions to ultimately grow. Right.

And so we had speakers from military Jock Willink who wrote a book called ‘Extreme Ownership’. We had speakers from put had on high growth companies like Molly Graham from Facebook and quip et cetera. And we had speakers that came out of music and fitness and all of these speakers we had and then we had one person that came out of marketing world Ryan Dice and we had one person that came out of the sales world and his name is Grant Cardone and we had a Grant come up. He wrote a book called 10x Growth.

It’s not the formula I made that up it’s called 10x growth something that’s not formula yet guaranteed steps. It was its growth mindset or something like that. And we had him come up he’s from Florida, Miami or some and we had them come up the group we had 12 amazing speakers and one that that was very bad and that was Grant Cardone. And I’d say the first third of his talk was OK and then the last two thirds were all over the map including one point where his wife Alena was in the audience and his whole entourage flew up and where he made some disparaging remarks about his wife during the conference. And so and most of that logistically like most of that I had started to hear from Twitter basically from the tweet stream. And so I later came out onstage at hypergrowth and apologised to everyone, took ownership for failing to have that speaker there. So it was painful.
ML: looking at that kind of tweet stream for the event there was actually a lot of people going ‘wow this guy’s cool’. So it’s really sort of interesting how you how you kind of manage and arbitrate between people who are saying interesting things, who may be saying unacceptable things as well. If a lot of your crowd is kind of egging them on. How do you how do you kind of change that in terms of culture? Is that just that sort… how do you sort of manage that – the kind of cultural thing – and what sort of how would you do things differently next time?

DC: I think you know most of this stuff that I saw which you price so we’re talking about the.  We’re referencing the first third or so of his talk which was on selling and market more marketing but selling and marketing and so I think those that that’s what the references were then the talk went off the rails. Yeah. And then there’s the next sequence of tweets.

So most of this was all of us backstage we’re seeing this kind of through tweets. And so we saw the same ones which you saw which were a bunch of positive ones those were at the beginning and then the timeline was then they then we started to see the tweets about like where this thing was going. And so from like ‘how do you change it’ standpoint. I mean what we did at Drift was we put more eyes on vetting the speakers including the ones that we had at San Francisco even though we had already booked them. And so like we have like nine people now and I’m one of them who are going through all the speakers and interviewing them before they come onboard. There’s some stuff that I was talking to another friend who runs a very very large conference much larger than the one we threw. And they have had experience with all sorts of stuff going on. There’s a lot of vetting that you can do before but as you know like when someone goes on like you know unless you have a giant hook …

ML: You know I’m quite a big guy.

DC: Yeah you’re a big guy. You could tackle them!

Q&A

ML: Yeah, I mean I think it’s an interesting thing. We’ve got a few minutes. Before drinks and networking starts at 18:30. I can’t access my computer so I don’t know if I have anyone asking questions on Twitter. So, do you want to put your oh we’ve got Mics so let’s start here with Glenn.

Audience Member: Thanks. Hi David. I’m curious what’s been your philosophy around fundraising especially in the early stages of the company?

DC: Yeah it’s an interesting question I think. You know, I’ve done I’ve bootstrapped companies and I’ve obviously taken a lot of money. I Drift we’ve raised $107million which is an insane amount of money. I think you know I think it depends on your outcome. I kind of view it as like ‘Hey you have to have your eyes wide open going into it’. I think most of the issues that I’ve talked to entrepreneurs and business owners about are always happen around this like they’re not super clear on what they’re getting themselves into. They’re not walking with their eyes wide open and they’re like I want to run this like when I still owned it but I want to like raise some capital from these professional people over here and I just want to keep it this way and I’m like these things are in conflict it’s never going to work that way even if it is temporarily because they have goals it doesn’t mean that they’re bad or not it’s just black and white what they want and, so, I’ve run into that issue a lot and I think you just have to know what you want. But again for me I knew that we were trying to build a certain type of company and knew what that would take and we’d like reverse back like an averaged out like how much money would it take and all of these kind of questions and that’s what led to our decision. But I think you need to be super deliberate because it becomes seductive when you’re bootstrapping a company that think like I can just take the pressure off and I can just raise money and it is temporarily and then and then it’s not. So just be clear.

ML: Oh hello

DC: I should’ve worn my sunglasses!

ML:  I know I was bright up there. Hello!

Audience Member: Hi. Great talk. You’ve had multiple entrepreneurial successes which is like the holy grail of Holy Grail. Are there any particular things that you think you know some things that really helped you get there. Was it around the environment? Did you have some weird cult that you joined? Share a little bit about who you surrounded yourself with and what key things or tools you feel helped you get to where you are?

DC: Thanks, I think for me when I look back at it I think it’s exactly what you said: who I surrounded myself with. But it wasn’t deliberate about that in the past like I can now look back and be like kind of I kind of think about myself as like the Forest Gump of this – like I kind of stumbled my way and I didn’t really know what I was. Now I look back I’m like That was weird I was around some amazing people that showed me this next set of things to learn and then I stumbled upon another one, and another one. And without having this deliberate kind of mindset I had my first stumble upon my first mentor in high school and college I worked at a warehouse I unloaded trucks and at this warehouse happened that the owner of that warehouse which I didn’t know at that time his name’s Sam Lee – who owned this incredible business in New York. And Sam was, he became my first mentor right. And indirectly and he kind of like a good mentor made me work super hard. He had emigrated here from Taiwan. I was the only person in the whole all of his companies that was not for Chinese as the only one. And I only got that job because my best friend at the time knew his family. He was Chinese and he vouched for me and so I got this job. And the biggest compliment that Sam ever gave me and why he mentored me over time, over years was that he said you work like a Chinese person. And I was like OK all right. I didn’t know how much that actually meant when he said that to me but I was the only compliment and I stumble upon him. And Sam was you know not that money means anything but he was like a first like really successful person that I knew but he was super humble. He drove an old car. You can never tell that he actually owned these businesses. It took a long time before he told me like I really found out. And like every trapping like you would think of like someone like that he did not have he is the most humble person ever. And he became my first mentor.

And then I stumbled upon another man another person named Sam who’s my next mentor. So I have like three mentors named Sam. Sam Lee, I have a virtual mentor Sam Walton – Whatever you think about Wal-Mart, which I don’t love, but like if you read that book that book has impacted me a lot. It has a lot around servant leadership about focus on the customer and what have you. And then Sam Zell’s is my third Sam but I stumbled upon these and then I stumbled upon many more including many great people at HubSpot which we talked about before and all of those kind of like opened my eyes to like what is possible. And so now I try to help everyone on our team make sure that they have their surrounded with that they have mentors and I help them find them, that they have role models people and that they are putting themselves in the right peer groups like this. I spend a lot of my time when I’m doing these one on ones making sure that they have those because those have been the most impactful thing for me personally and I want to make sure everyone has access to that

ML: Thank you. All I can see is lights.

Audience Member: I’ve got a microphone so I’m going to go for it! Hi, So you talk a lot about your you mentioned earlier not separating professional from personal growth and as long as we’re on the topic of diversity inclusion especially given what happened with Grant Cardone something I’m interested to hear more about from you is when you’re growing a company at scale how are you ensuring that your own personal values related to diversity and inclusion are kind of trickling down to the rest of the team at Drift. And what are some steps that other CEOs and founders can take?

DC: Yeah that’s a we’ll probably be here all night. This is a good question to talk about. I like this question. It’s just a surreal question. I will say so like we want to be like “Raw at BoS”! It’s a surreal question because I think like, I kind of grew up in these environments where I was – I’m Hispanic – most people don’t know that but like when I was the only brown person. Right. And so I’ve dealt where it’s like everyone has dealt with things you know racism and lots of issues in my life. And so like but now I’m on the other side and almost surreal to like it’s almost like a movie almost like …

ML: Not so much the underdog

DC: Yes. I’m not the underdog anymore I’m on the other side and then then so people then ask me about do I think about diversity and I’m like kind of like thought about diversity my entire life!

ML: What’s Drifts gender split for example?

DC: Pretty close. Depends on the role. Right. Obviously. And so it’s easy. The total company size is pretty well because STEM is very different. But right STEM is very different. So which we could talk about from a company standpoint we’re pretty close to 50/50 from a STEM standpoint and product standpoint we’re like probably like 30-odd%, 35% stuff like that which is pretty high but like but obviously not 50/50. I think STEM. The reason I say obviously, STEM is an important one because that goes back to what we were talking about earlier which is like some a lot of these answers are multigenerational answers I’d like to fix the problem in stem specifically coming as an engineer like that’s a multigenerational problem because from a math standpoint the math does not make sense right. Like if you look at I think – I forgot the last numbers were from Google and Facebook I spent a lot of time on this – like you know if you have you know total STEM graduates from a gender standpoint being you know I forgot the numbers let’ s say it’s 20% right. It’s sub 20% but let’s say it’s 20%. The idea that in the next couple of years we’re all gonna be at 50% is obviously mathematically impossible. We have to change some systematic things and we can get closer to whatever the number is. But it’s hard because it means like I have these conversations with people both in the building, outside of building all the time of like you know I might be talking to found out I want to get to 50% and it’s like and then I want to feel like you know my view is like well one that’s amazing to like mathematically how would you do that. And would you feel as good knowing that you got to 50% but it means the two companies next door to you have to be at 10% in order for you mathematically if you want to short it solved in the short term.

Those are very real things that nobody wants to talk about that they want to talk about like a hashtag thing or whatever. And it’s like that’s a real problem. So how do we what are we doing and that’s where I want to. What I’m doing, personally, is like how do we invest in making starting all the way back here. Because all the way back. Here’s what it’s actually going to take right. And so it is a tough tough thing. In terms of like how do we do this at Drift. We talk a lot about it. We talk about it. I talk. We talk a lot about it with our recruiting team and all of our people who everyone on the team basically recruits and say like it’s not enough to think about it from a high level or firm initiative standpoint the real way that you are going to do this is every day and that means like maybe you know this flow that you have this way of recruiting fees really easy. This other way that’s going to open up the pool is really really hard and maybe we’re going to say no to these really really easy ones and you’re going to do the hard work and that’s going to be three times the work for you. That’s how you’re gonna do it. Like not by just you know being pumped up about like some high level program. And so the answers I always think the answers to everything are like hard and took a lot of hard work. And so that’s how we deal with it every single day. And it’s like growth, it’s hard it’s not comfortable to do it every day.

ML: Okay. Thank you. Right. So I’m actually sitting here and can’t see a thing!

Audience Member: Thank you so much for sharing with us today. I’ve heard you talk a lot about process so far like thinking about product thinking about marketing and thinking about what you’re doing every day. But you know this morning we heard a couple of talks where we’re sort of the subtheme running through both was the notion of creation not as an act but as a product as a business separates from the founder. You’ve been through this a bunch of times and sometimes you described it as stumbling into at least in the past. Have you given thought, do you have a plan for what your last day of Drift is and what do you want it to be?

DC: Yeah well you know it’s funny my partner, my wife, you know for four years was always the one that was like hey you should start and then the company when I was like really? Really should I started another company. And then during Drift like in the first two years we had a conversation she was like “This is the last company!” I was like well what does that mean? Like what do you mean? And say. This is the last company. So like make it count like this is it. I’m like What is what does that mean. My wife and I met a long long time ago and she’s an entrepreneur as well. She sold her company long time ago to company call oxygen media in New York and she wrote a book and she did this and she’s professor and then all this amazing stuff. She is a super powered one for sure and she she’s like now I’m going to go start now I’m going to be entrepreneur and you’re you know we’re going to switch places so Drift is my last company for sure. Definitely. There’s no doubt about that hundred percent 100% guarantee

ML: Have a word with the boss.

DC: Yeah. Yeah it was. But I really haven’t set a date yet for that’s a great question that I haven’t set a date yet for when my last day will be aDrift. I’m still learning that process of which I think all of us are like how do you let go. We/I created this idea when we started company about three year sabbatical so every three years you will get one month off which I thought was a cool idea. I’ve never taken one month off in my entire life. All right working life since 13 and then this year I did take a month off because I was a member of the team who was there at the beginning said “Hey remember that thing my three year sabbaticals. It’s like three years now.” I was like what wait tell me that. Yeah and then then I was at home and my wife and I were talking and she said ‘Oh you you’re going to have to take it’. I said Why. Nobody’s going to take it. And I said even up until the day before I was supposed to leave I was like I don’t know if I can do it because I’ve never done it right. I’ve never taken more than a week off that I can remember and then but that month off was amazing I’m the biggest supporter of sabbaticals haven’t gone through it because it let me see things in the business that I couldn’t see because I was too close. And the reason that I mentioned that is that in a weird way that’s not me leaving or stepping down. But it gave me a way to like understand like that this thing can go on and like that this distance can be okay like personally

ML: maybe this isn’t just about you having time off. That was about you having space when you weren’t doing your day to day but I was still thinking about business right? 50:19

DC: I stopped if you believe it took me I can’t. It’s unbelievable if you would’ve told me. It took me two weeks into it. Yeah I was reading obviously I read all the time. My daughter is super, super equestrian, like super into horseback riding and so I took her to an event that she was doing in Vermont in a place where there was no cell phone coverage. So in some ways I had no choice. And I just was a stable hand for two weeks. And that forced me to just be present.

And I was and I was meditating as well which I do and I was okay with it. And so it taught me a little bit of what you’re asking about like that it was it could be okay when before was always wrapped up probably like all of you in my identity and that I have could have an identity outside of that. And my biggest fear though by the end of this sabbatical is like maybe I’m never going back. Maybe I’m on sabbatical forever.

ML: were you a very good stable boy?

DC: I was a very bad, very bad, bad stable boy. You know I was good at clapping good clapping, good supporting, good and getting water and cleaning stuff. Yeah. So maybe I was a good stable hand. That’s all it is my job.

ML: We’re going to wrap up now. But see you ever over the over the road for drinks. Yeah. I’ll leave you with one question: What do you want to be remembered for?

DC: Helping people learn. All right. Which is what I want to do. All right. Just being able to assist them in their learning in their journey of growth.

ML: Okay, Ladies and gentleman; David council. Thank you sir.

David Cancel

David Cancel is a 5x founder and 2x CEO with four successful exits to date. Currently, he’s co-founder and CEO of Drift, where he’s helping marketers transform their relationships with customers to drive retention & growth.

More from David.

Next Events

BoS Europe 2025 🇬🇧

🗓️ 31 March – 1 April 2025
📍 Cambridge, UK

Spend time with other smart people in a supportive community of SaaS & software entrepreneurs who want to build great products and companies.

Save your Spot

BoS USA 2025 🇺🇸

🗓️ To be announced soon
📍 Raleigh, NC

Learn how great software companies are built at an extraordinary conference run since 2007 to help you build long term, profitable, sustainable businesses.

More Details