Seeking Wisdom Live At WeWork

As the Seeking Wisdom community keeps growing, we keep looking for new ways to bring that community together.

Our latest idea: Record a live episode of Seeking Wisdom at WeWork South Station in Boston.

Listen to this special and candid live episode as we discuss the history of the podcast, review our top episodes and themes, and answer audience questions along the way.

Seeking Wisdom Live At WeWork | Seeking Wisdom Podcast from Drift on Vimeo.

Time Stamped Show Notes:

00:45 – Intro to live session

1:28 – How the Seeking Wisdom podcast got started

06:40 – Thoughts on hiring practices (Listen to the “Management & Career Growth” episode)

10:18 – “The Secret to Becoming a Learning Machine” episode and David’s obsession with learning and mentorship. (Listen to  “The Secret to Becoming a Learning Machine” episode)

14:14 – The importance of role models as a benchmark

17:15 – Audience question: How do you select your role models based on where you are in your life?

22:26 – Work style at Drift: transparency, intensity, showing your work and autonomy

26:25 – Thoughts on ownership and autonomy

29:57 – Audience question: How do we deal with mentorship at Drift?

31:09 – Audience comment: Autonomy increased productivity at his organization.

32:26 – Audience question: How do you pick what to obsess on and how you obsess over it?

36:07 – Audience question: What are your pain points and learning experiences from the previous business ventures that came before Drift?

38:45 – Audience question: What’s something you guys have changed your minds about recently?

41:10 – Audience question: Have you done anything differently because you’re both a Founder and CEO of the company?

42:12 – Two marketing mega-trends people should be thinking about: video and messaging

44:23 – Audience question: What daily habits have led to most of your progress?

47:13 – Audience question: Do you feel a responsibility to do social good?

49:12 – Audience question: How long do you focus on a great idea that doesn’t gain momentum?

50:56 – Audience question: Does Drift have a company role model?

3 Key Points:

  1. Keep learning and acknowledge what you don’t know.
  2. Create a culture of mentorship in your organization and make a list of role models to aspire to.
  3. Always be progressing in your learning to push yourself forward and stay interested.

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Come hang out with us at and on Twitter @seekingwisdomio.

Learn more about Drift at

Episode Transcript

Dave: I thought what we’ll do is maybe go for 30 minutes and then there’s a bunch of good questions, most people have questions for you, I already heard some good ones.

David: Is it for Drift?

Dave: No, no Drift questions actually but they did sit in the front which is nice. Michelle’s already had half a beer so we’re in trouble. How many of you listen to the podcast right now?

David: How many people have left five stars?

Dave: What’s up with that?

David: Do we have a five star booth?

Dave: We do. You put your head in that booth and you get six stars right there. I pulled out a list of the top five or six episodes that we’ve done. I want to revisit some of those with you. Maybe let’s give some background like how did this whole podcast start, because we didn’t really set out to actually do a podcast, maybe let’s start there.

David: Sure, I have no idea. I think the way it started was we were having these conversations in the office, if anyone visits Drift, and we’ve had a number of people visit who listened to the podcast and they listened to it with the two of us talking there like, “Wait, that’s just a podcast.” We were having these conversations and I think told you at some point that I was thinking of recording a podcast or I was recording some of these conversations. You pulled me into a room one day to try to make this into a podcast. The context is DC used to have his own podcast, that’s how we met. He was doing a podcast at HubSpot before that.

Dave: If you listened to the podcast, which a lot of you had, you’ll know that DC doesn’t really remember anything. I’ll tell you what actually happened, that’s partially true. I had this podcast, Tech In Boston, I did on the side. That’s when I interviewed you and that’s when we met. I was like, “This guy is really mysterious. I kinda can get what he’s saying.” I found that you guys are hiring a marketing person, that’s how I ended up working at Drift.

                      In the interview process, you said to me, you’re like, “Oh that’s cool, you do the podcast thing. I’ve always wanted to do a podcast.” I was like, “Oh really? What is it about?” You’re like, “I don’t know what it’s going to be about but I know the title, I know it’s going to be called Seeking Wisdom.”

                      We had probably three or four months into doing marketing at Drift. One of our advisers Steven Shaw, who has a lot of followers on Twitter, if you are on Twitter, serial founder, done a bunch of companies. He said to me, “You’re fucking up right now.” I’m like, “Why?” He’s like, “You need to be putting DC out there and promoting his stuff.” I was like, “Okay. He’s the CEO, he’s super busy, doesn’t answer his email, I can’t get him to respond to anything.” The default form of content for most people is like, “Oh, he’s going to write.”

                      I remember thinking like, “There’s no way am I ever going to get to you.” This isn’t just you, this is every exec, or founder, or entrepreneur. You just hardly have enough hours in a day for you to sit down and write a blog post. But every night you would send me something on Slack, I’ll just be like, “Damn, this would be a killer blog post. Text me at 6:00AM about something crazy. What can we do with this?” I don’t know, shit. Maybe we should do this podcast and get you an audio format so then you can just go.

David: Do you want to know the secret?

Dave: What’s the secret?

David: I haven’t told the secret before. When I met you, the day you interviewed me for your podcast, my secret plan was when Dave came back, I wanted to work at Drift which is a whole another episode, we should do that.

Dave: He wasn’t going to give me an offer until I came back from my honeymoon and I said, “I’m not leaving until I get this and then I went on my honeymoon.” Lia would tell me today, she’s like, “Thank God you weren’t working on our honeymoon. I couldn’t deal with you looking at your phone the whole time.”

David: He came in and he said, “We did this interview on his podcast.” He came back and said he wanted to work at Drift. He came in and we were like, “I don’t know, we’re going to hire someone in marketing soon but we didn’t know when.” I said, “Go on your honeymoon. We’ll talk after you get back from your honeymoon.”

                      He texted me or he called me and he said, “No.” I said, “Why?” He said, “I’m coming right over.” He comes over, he lives just across the street and he says, “I’m not leaving until I have an offer.” I know it’s going to happen. I’m going to go on my honeymoon, you’re going to hire someone else. It was amazing, the most amazing experience. Here’s the secret that you didn’t know.

                      The secret was when I met you and we were doing the podcast and then you were doing The Growth Show before that, I thought, “Dave is going to come here, we’re going to do a podcast but I’m not going to tell him that we’re going to do a podcast because if I tell him that I want him on the team to do a podcast, then he’s not going to want to do a podcast because that’s just what he did before and he wants to do something new so I’m going to lurk him in and I’ll make it seem like it’s his idea to do the podcast.”

Dave: I need a minute.

David: That’s the secret move.

Dave: That’s crazy.

David: That’s called 3D Chess.

Dave: That’s crazy because there’s so many things that we’ve talked on this podcast about in hiring. The traditional thing would’ve been like, “Oh, he’s done a podcast before, let’s hire him to do a podcast.”

David: I went the other way and I said no, I’m not going to bring that up. I’m going to bring up everything else because that’s going to be something new and different for you and then I’m going to plant enough things that eventually you just say, “Let’s just do a podcast.” And we did.

Dave: Damn, that’s crazy. I had no idea, that’s pretty good, evil. Evil genius. There’s a lot of things in hiring that we talked about a lot that I’m super interested in. I’m trying to figure out now like building a team and trying to figure those things out. One of them is, we talked about all the time, this is one of the episodes that was popular, it’s about hiring. My default now is like I’m going to look at your LinkedIn and be like, “Oh you worked at SalesForce, you worked at this other big company. You’d be a perfect fit for our team.” A lot of times those people are just really shitty fits. They might be amazing at what they’re doing but they might not be a good fit for what we’re doing.

You had this other playbook which is like what are the other skills. Was it something about doing a podcast and you said maybe this guy could do marketing?

David: I think it was something about the way that we did the podcast that was natural, this was a hit podcast when you interviewed me for Tech In Boston, that I thought was natural. I love that you had this aggressive attitude which was I’ve never met a marketer with an aggressive attitude. You kind of reminded me when I met Aaliyah, cofounder.

Dave: He’s now famous because he’s been on the podcast.

David: One time. In his mind, he’s so fucking famous.

Dave: You haven’t been listening for a while. David’s co-founder of Aaliyah’s. They’ve done their third company together.

David: Fourth company.

Dave: They’re like a married couple, it’s unbelievable. It’s incredible.

There’s a great episode a couple weeks ago where DC sent Aaliyah down to this bootcamp with a navy seal which is a whole other episode, you should go check that out.

David: He had his big mouth and he tells me that people stop him on the street which I don’t believe. You remind me of Aaliyah’s because you’re nothing like, but Aaliyah’s was unusual when I met him years ago because he was the first engineer that I met that was so extroverted. I thought that was his superpower so I thought, “Alright, I’m going to get this guy to work for me.” Back then, I just wanted these companies to work together because he’s got this thing that is weird.

                      I was talking to someone on our team the other day, Matt. Matt has a super power that he’s been trying to hold down ever since I’ve known him because he doesn’t think it’s valuable. I saw this super power in you that you were ready to be aggressive, ready to get out there. I thought like, “Oh man, we’re going to build our brand, forget the podcast but build a brand. We’re going to have to do it one on one and this guy can do it one on one.”

Dave: I love that. There’s so many hiring lessons in there to just go deeper. The whole way that you go through that in an interview is you ask people about a bunch of different topics. I’m in there for marketing, you might ask me about marketing, golf, basketball, podcast, reading, and you’re looking for that one thing to see what’s one of those things that I light up at.

David: Today, I was talking to someone that I’m trying to hire, I’ve known her for a long time. I’ve been waiting five years for the exact role that she’d be perfect for. Now is the time, the first time that I’ve gone after her.

Dave: When you’re interviewing her, is she lighting up about the topics that you guys are talking about?

David: I’m talking exactly about an area that I think she wants to grow in and that I’ve been thinking about for the long time. Because that shows that I’ve been thinking about this person for a long time, it’s not just about coming in and working here, it’s about meeting what matches with what they want to do.

Dave: I want to completely change topics on you. One of the early episodes that we did that has the most downloads today, I think it’s called The Secret to Becoming A Learning Machine. I want you to talk a little bit about your obsession with learning. This is coming from a guy who didn’t read books until probably two years ago. Never read a book in high school or college.

David: Now he reads books, he sends me passages highlighted with his book.

Dave: Last night I had a book up, feet on the couch. Why is that something that you’re obsessed about as a founder, as an entrepreneur, and what’s in there that relates to the building of businesses?

David: I’d say I have an obsessive personality, it’s actually an addictive personality. I go all in 100% on things. I think I was talking with someone, some reporter today from Forbes.

Dave: I’m the marketing guy, you’re talking about Forbes.

David: It was about mentorship. I said, “The reason that I’m obsessed about mentorship or role models is because I didn’t have any. I didn’t know that this was a thing that you can have and that this was a shortcut path, when I did have those books.

Dave: Where did you grow up, give us some context.

David: Queens, New York. I was born in the Bronx, South Bronx, New York.

Dave: Did you go to college?

David: I did but I dropped out. I lived in Queens, New York. I went to college, I studied Computer Science and Accounting and then I dropped out. The only reason I can think of why is because I was bored as hell and I was obsessed about wanting to start a business but I didn’t know what a business was and I didn’t know how you started one. I had this accidental mentor who’s my first mentor, Sam Lee.

                      From that, I discovered this power of like, “Oh, having this mentorship, I never even knew that term.” I think I knew that term years later. I didn’t know that he was a mentor at the time until I experienced it. I became obsessed with this kind of idea of mentorship, of learning and acceleration because it was giving me a way to shortcut things.

Dave: One of my favorite things that I’ve learned from you is the whole thing about reading. You don’t read or learn to really learn something new, it reinforces these things that you may have already been thinking.

David: Yeah. I think the important thing about mentorship and reading and role models and all this stuff is that the one thing that we have as humans is that we can simulate, meaning that we can read some things or view some experience on video or audio or whatever that we have never done before and we can mentally simulate what it’s like to do that. That’s one of the things that separates us. By reading, you can simulate using other people’s experiences and try to avoid the mistakes that they’ve made.

Dave: There’s so many things, we talked about marketing, positioning a company. It’s already been written, the challenge that we’re going through has already been written, it’s just finding who said it at what point in time and what we pull out and relate to what we’re doing.

David: Being humble enough to listen to that, listen to what you’re hearing or what you’re reading, I think that’s the hardest part. I think everything that you send me when you read now, you’re like, “Oh shit. Look, someone wrote this. This is exactly what we’re doing. This is exactly what we’re talking about.” But it’s like a discovery and you’re like, “Holy shit, this thing is speaking to me right now.” It was always there but you have to be in the right context to pull it out.

Dave: The other part in there that I think is interesting, that I didn’t really think of until I came here was your obsession with role models, but from a benchmarking perspective. Can you talk about that?

David: One of the things that I think that we use role models for and I use role models for is the benchmark. A lot of times, you might be taking on a new job or a new challenge or doing something that you’ve never done before, you don’t have context for what is possible, you just have your local group of friends or the people that you work with as your role models.

What I try to do is find people who are 2 years, 3 years, 5 years, 10 years ahead of where you want to be in a particular thing, whether it’s health or work or whatever personal. Use them to pull you ahead and understand what does good look like, what does great look like, what does bad look like. If you have enough of these people, you can start to benchmark where you are and then you can convince yourself, you can simulate and say, “I know everything that they know and they don’t have any secrets so I can actually achieve what they’ve done.”

Dave: How does that apply to what you’re doing leading and growing Drift?

David: I’m constantly looking for my own role models. One of the things that we talked about just working together is I’m always pushing Dave. Who are your role models right now, let’s take a list. We look at them, we review them and then I’ll say, “Those are the role models for six months ago, we need the next two years from now or else you can’t pull yourself along.”

Dave: It’s an easy pattern to fall into because I think we had a conversation awhile ago, we’re like, “I thought I had the right role models.” You’re like, “No, we’re already past that.” That’s context. You’re comparing yourself to a whole different group, you need to think about. That’s uncomfortable, though, because you’re going to compare yourself, it’s like working out. That’s the easy example of fallback but if you see that guy that’s 6’6” and just shredded and you’re like Brogan, oh my God, that guy could rip my head off. He was in my Instagram DMs this morning, just for the record.

David: This is Brogan from November Project.

Dave: But you have to see someone that’s uncomfortable enough out there to let you know it’s obviously possible for that person. Other than the whole 6’6” thing.

David: I can’t wait to put out that episode because Dave does crossfit all the time, he works out but Dave was looking small last week, Brogan was.

Dave: DC came up to the lobby, he’s like, “There’s a monster down the lobby waiting for you.”

David: That’s a good example, it’s a completely different path but you know that that’s out there. I’m kind of feeling that we should take a question or two right now. Anything on anybody’s mind?

Audience 1: I think you bring up a really good point about role models, this is something that I’m personally torn between because on one hand you have people like Mark Zuckerberg who started some company. I’m 28 now, he just turned 28, I’m very far away from starting my own company at the age that he was at. But then on the other side we have someone like Arianna Huffington who didn’t start at The Huffington Post until she was 40. How do I gauge where I’m at versus where they were at versus where I want to be? How do you select the right mentor for you?

David: That is a tough question to repeat. How do you select your role models based on where you are in your life? I’d say one thing, those are amazing people but those are fictional role models. Maybe you can get to them but most of us won’t be able to get to Zuckerberg or Arianna Huffington. I think you need to think about who are the people that you can actually get to, who would get you on the path towards maybe them or maybe someone else. Who is addressable? Who is actually addressable that you can get to?

                      It’s not like getting towards the $3 trillion end goal but it’s what gets me the next 12 months. When we talk about role models, we’re talking about in 12 month chunks. Who’s the role model for the next 12 months?

Dave: One thing that he pushes me on is he says, “Okay, don’t go and look for somebody who is 20, 30 years older and 15 pay grade.” Find out who are the people who are doing what you’re doing right now but are the varsity level, locally. I might say, okay, I got to go cold email three VPs of marketing or three CMOs and go find those people locally. You can get to anybody, especially locally. You’re never going to cold email Mark Zuckerberg like can I pick your brain? Can I get a copy with you? Find who’s that person that’s like half a level above.

                      The other thing that is interesting often times with that, you also learn the flipside of that which is reversal model. It’s an entirely different topic.

David: I think one state had role models and a series of role models and that was going great, then I sent him to a couple of events, they were close events, small events. Because I said, “Now you got to go meet some reverse role models.”

Dave: You didn’t tell me it was reverse. He sent me to this fancy ass dinner, I walked in with sneakers and jeans on, sorry. It was at this crazy restaurant in Cambridge, we’re sitting around, a bunch of things in the menu that I’d never had before. I’m like, “What am I doing here?” I was really embarrassed, I was really nervous, I was like, “These people are going to look at me and be like, “What? Who’s this little kid from Drift?”

David: They were CMOs.

Dave: They were all CMOs and me. They started going around the table and talking about the problems in their business and I was itching. This isn’t a reflection on them. The problems are the same and it made me realize, these are all things that we’re thinking about now. I texted him on the way home and I was like, “Hey, thanks for inviting me to that dinner. Really put things in perspective.” He’s like, “You just learned.” I was like, “Yeah. Was that a trick?” He’s like, “Yup, reverse role model.” I went home, I was so confused, I was like, “What’s up with that? I don’t know.”

David: I knew the people who were going to be there are great people but I thought these are going to be the reverse role models because these are people that are running at a slower pace, probably doing things that are not the type of things that Dave might be doing or we’re doing, a little less interesting. This is what the reverse models look like. Also, it would show you that you already know more than most of these people on the table even though if you would look at them from just a LinkedIn standpoint, you would probably be nervous and you were nervous when you were there. Then you start pushing the deep water back.

Dave: There is an important lesson there because I’m an introverted extrovert, I can turn it on of I need to but most of the times, I just prefer to not really talk to anybody and just hangout. I hate doing stuff like that, I hate networking, I hate doing that stuff but that was a good lesson to push yourself to go to that thing, to go to maybe something like this or whatever just to realize, “Yeah, these people are much similar to me, much more similar than I thought. Damn, I have a ton of work to do.” Because I think both of them work in ways to inspire you.

                      Number one, when you see what people are already doing, you’re like, “Oh, I’m on a good path.” But then when you really get to the elite level or another level, you’re like, “Shit, I got to put work tomorrow.”

David: Exactly. That’s why you have to keep upgrading your role models and get the next 12 months, next 18 months.

Dave: I think the advice there is you’re not just going to skip and go right to Zuckerberg. Who are the people, maybe even here locally, that you might be able to go and grab?

One topic I definitely wanted to talk to you tonight about is work. This is like you and Aaliyah’s and this came from you, we have a really interesting way that we work at Drift that I don’t think is really similar to a lot of companies. I want to let you talk about it.

I think there’s a couple of things. Number one is transparency. I’ll list them out and maybe you can talk about them. Intensity is a big one, showing your work is another one, and then autonomy is probably the fourth one. Did I miss any?

David: I think the transparency one is hard. I think the intensity one is probably the biggest one. The way that I think about it is we have this crazy machine that we’re trying to achieve, we’re here for this huge purpose. We run at a pace that’s probably unusual for people, I know that’s unusual for people. We’re trying to create this team, we think about this concept called the Drift 100 which is the first 100 people that work at Drift, we’re 50 something now. We’ll be the 100 that build a foundation for the company, we think about those people need to have this outside intensity and outside’s hunger.

I also want people to look at the team externally like, “Holy shit, look at that team.” Look at them, go across the team and say, “That team is loaded.” They do, everyday. Because of that, we run at this intensity because speed is one of our advantages. What do you think about intensity?

Dave: I was just going to ask you, we’ve grown from 10 people to 50 people in this. I think we’ve skipped over a lot of the middle management phases and some of the admins and stuff. I think the intensity drives us but also you have to be completely uncomfortable with not knowing what your full job description is in a given week or given month. You know what you have to do today but things change so fast and it sounds cliché to talk about startup but it really is a super fast experience. I think the intensity is just like you have to be comfortable with everything always being uncomfortable, that’s been the biggest lesson.

David: I think we have a lesson that is everyone has a different context. I think for a lot of people who would come to Drift and who are in Drift, “Holy, this might be the most intense environment that you’ve ever been.” But then, I think, in my personal context, like the companies that I’ve been of, it’s not close.

Dave: You actually were texting me the other day, you said, “We should do a Seeking Wisdom episode on this.” We’ll do a full one later. But really, the context was it can’t be that intense, we have bean bag chairs and free beer and snacks. That’s the context. You start companies in a different decade.

David: What are you trying to say?

Dave: Every time I go there, you still think that OG stands for old guy.

David: I just had a different experiences where there was, before this at HubSpot, whatever, the intensity level was, we’ll do an episode on this, through the roof. I would say most of those environments has the least intense person.

Dave: One thing that’s been interesting for me to see, this is something that you guys started HubSpot with idea for a really small autonomous team, the ownership piece in autonomy is interesting. I would love to tell people a little bit about how you think about that. A big thing that is in your company’s plural DNA is this idea of autonomy.

David: I think it’s super important, I’d say first that it’s a progression, everything is a progression to me. I think it’s something that gets created over time. If I look at where we are now at 50 people, there’s some autonomy, that’s not the level of autonomy that we’re shooting for, for sure, but it’s a progression where you can build this over stages. When you talk about it, people may expect like it’s spontaneous but it’s not.

Even when we did it at [00:27:45] and then later at HubSpot, if you were there in the early team, it was the same way by the time it was a couple of hundred people in that product team, it was insane autonomy, insane amount of ownership. It’s a progression over time as we stand up the system. I think it’s important because we want to create the environments that we want to be in. I’ve always been an entrepreneur meaning that I don’t like being told what to do, that’s what my wife says to me repeatedly because I don’t like being told what to do.

Dave: What does that mean in the word context?

David: We want to create the environment that’s like that, that’s entrepreneurial, most entrepreneurs share that. You want to create that, you want to have autonomy but you have to also develop the systems so that you have the right level of accountability and transparency so that the system works because if you don’t have the accountability and the transparency systems in place, then it’s just a free for all and it’s fucking crazy.

Dave: That’s the thing that gets people’s attention. I think we talked about that on the podcast before. There is a piece at work that is like, “I want full ownership and autonomy but also I’m going to show up when I want and maybe not really do the things that I’m supposed to do.”

David: It’s just a learning process, I don’t know if it’s new or not but I think it’s something that we’re trying to push and I think it’s something that’s important for people because you want to create an environment that everyone feels like they’re entrepreneurs. As we add every person on team, the one thing that I think about with each person is like, “This person has to be capable, if we add them to the team, in a few years to run a team that is as big as the company is now.”

Dave: Do you feel that way? Will that be how you think of things until 100 and then it changes?

David: No, I keep thinking about it that way. When you come in, you have to be able to run a team that may be as big as your division, maybe as big as for us the whole company is now. It might take 5 years, it might take 1 year, it might take 10 years, I don’t know how long it takes for each individual but they have to have that capability.

Dave: Anybody have questions?

Audience 2: How do you address mentorship at Drift with autonomy? Say all your managers get in one room, how are you coaching them?

Dave: How do we deal with mentorship at Drift? I think we all push each other, I think our men, our VP of sales is here tonight. I see him out on his own hosting a dinner with 20 other VP of sales in Boston. I’m like, “Shit, where is my group, what am I doing? I need to go out.” You build the culture, it’s competitive in a good way. I think one of the things that is embedded in our company’s culture is this idea of always learning. That could be always reading, always listen to Seeking Wisdom or whatever or always out there and talking to other people. That’s just in our DNA.

                      I think it’s really hard to be in a culture like that if you’re not. I know this myself, I never read a book ever, and then I go to Drift then I’m like, “Oh man, I gotta find some way to be smart.” When you see what everybody else is doing, it just pushes you.

David: I like that answer.

Audience 3: It’s not really a question [00:31:22] in your experience. I have the chance to implement the autonomy but our engineers were actually, the level of intensity went down because they became far more autonomous. They were able to produce much more in a more relaxed fashion and they also self-organize.

David: They were able to create more?

Audience 3: Create more with less effort.

Dave: Yes, absolutely. We’ve seen that in the past too which is something that you wouldn’t expect, you create this environment. It’s because you have to have the right guard rails in place. For us to grow [00:32:03] around the customer, if the customer is getting happier and better and buying more for your particular team, engineering team’s product, then things are going the right direction then we shouldn’t care about timelines and release dates and all this kinds of stuff that you usually judge an engineering team on. The more you do that, the more control that they have and the happier they are and the more they’re building and the more that they self-organize.

David: One vote for autonomy.

Audience 4: You talked about learning earlier, how do you pick what you obsess on and how you obsess over it, because if you do it in the wrong way and then you’re obsessing.

David: Because I have an addictive personality, I’ve had to channel my addictive personality traits to be focused on things that are positive. For me, it’s always learning something, learning something positive. It could be about work, I could obsess about making pizza, that was a long time ago, or cars or bicycles or whatever I’m obsessed about at the time. I think my obsessive personality could also go dark. I can’t just be obsessed about all bad things, all kinds of vices, that would be easy.

                      But for me, I think it’s not just obsessing about learning just for learning’s sake, but learning type of progression. You’re trying to progress in something whether it’s work or personal or whatever. Your learning has to be a type of progression or else you get bored just learning for learning’s sake. For me, as long as learning keeps pushing my progression, then that’s the virtuous loop and so then it becomes more and more fulfilling and the more and more I want to do it because it’s pushing me forward.

Dave: You can also look backwards at it, this is what he pushed me to do last summer which is like, “Alright, we need to get better at marketing.” What’s the most reasonable skill that fits with what I might already be interested in or good at? He’s like, “Alright, here is your mission, study all the great copywriters and direct response marketing people.” He could’ve said, “Learn how to be a master at Google Analytics or setting up this and that or something technical.” But he’s like, “Okay, what’s probably already a strength like talking, communicating, and channeling that into something. I’m sure you know there is one or two things that you’re probably already good at.”

                      I think the biggest lesson has been to double down on strengths versus worrying so much about sharing up different weaknesses. I think it’s human behavior in order to be, I’m not really great at this thing so I’m going to spend all my energy trying to get better at it, when the real super power comes when you take something that you’re already pretty damn good at, spend all your time on that thing and then you’ll become an absolute superstar in that one category.

David: I think that sounds easy, it’s easy to say. Usually, people are dismissive of whatever they’re talented in and they want to get better at something else. For Matt, I’m talking about Bilotti, I would use him again because he is a product manager on the team, he is the first product person on the team and he’s a really good product manager but then he has this other weird skill which is he’s great at public speaking, I thought he would be great on videos, he’s a storyteller, he’s a personality.

Dave: He’s the guy that would lead a campus tour at college.

David: In a shark suit. He has got this outside personality and he can translate technical things easily to people because he can tell stories. I thought he would be good on video because of his crazy personality but he just kept dismissing it and said, “No, no, that’s not good. I don’t want to do videos.” I taught him into doing videos, this was probably a year and a half ago. He did one and then he saw the reaction that people had and they’re like, “Holy shit, that’s very funny.”

Dave: And then people started messing around his beard.

David: Now he’s starting to see that’s a unique super power that he has that I haven’t seen many people have in his intersection or product and video.

Dave: Anyone has a question?

Audience 5: First of all, thank you guys for doing this. I want to ask about, obviously, Dave, you’re a serial entrepreneur.

David: Drift is his last company, by the way.

Dave: My wife told me that. I was like, “What?” She’s like, “This is the last company.”

David: I’m only 30 and my wife said the same thing.

Dave: I’m like, “What do you mean?” She’s like, “This is the last one.”

Audience 5: I wanted to ask about the early days, OG, DC, the learnings or pain points that you were able to take from that time and apply to Drift now.

David: My first company, it’s a long time ago now. It was hard, it was a really hard company. My takeaways were we built an amazing team, we sold that company in 2007, it was great but I never really cared about, as an engineer, CTO, and I didn’t really care about culture. We had a pretty hard culture because half the company, half the team was sales or consultants at that time and they had a certain hard charging personality.

Dave: They were sales guys.

David: No. Actually the sales guys were easier but consultants were harder. They were like all [00:38:04], a whole team, that kind of intensity. I have never gone home after Will, never, ever. We never cared about culture and then at the end I was like, bunch of amazing, really smart people who are still friends today but I don’t think we’ve created a culture that I was that proud of. That became a learning and I started to focus on that.

I think the other learning from Compete was we went back close to the customer from an engineering team standpoint. That’s something that we want to apply at [00:38:41], then we applied it again at HubSpot and now we’re continuing there. There’s two learnings around being close to the customer and caring about the internal culture.

Audience 6: What’s something you guys have changed your mind about recently? Like a belief that you’ve changed recently because of information?

Dave: That’s tough.

David: Have I changed beliefs on anything?

Dave: I don’t think so.

Audience 6: You’re always learning new stuff, changing, ideas and stuff like that.

David: That one is a hard one because I think that’s a really good one but it’s hard because my fundamental belief is that I don’t know anything. That’s the core thing I think we talked about internally, we call it internally defaulting to wrong. We just think every idea we have is wrong, we need to validate it which goes to the customer driven thing. My mindset is like whatever we’re saying is wrong somehow.

Dave: That’s an important point though, that’s worth mentioning in front of this crowd. Is your obsession with being none of us know the answer, if think you have an idea, you need to ship it. It could be a code, design, a blog post, a video, or some idea. I’m sure you’re talking to so many people who want to pitch you on an idea for a company that haven’t even launched the company yet. That’s just one example of the whole idea, ideas need oxygen. The only way to learn is to actually get out there.

David: It’s something to talk about a lot, it’s just ideas need oxygen and that the idea and the equation process is always the same and that you need a feedback loop to go on it. I think that’s totally different with the one that we did at Compete where we probably in that phase it was more of like yeah, we have this idea, this is their idea and this is what we’re going to do. Now, I’m 180% on the other side. We have a bunch of great ideas, probably a lot of them are wrong, we need to get into the market, we need to validate it and all that matters is building around the customer.

                      If we can do that, we’re lively over and over then we will win because that’s uncommon, because most people are not willing to say that most of the stuff was wrong because ego gets in the way and they’re not willing to be that close to the customer. That’s our advantage.

Dave: Most people just never get started. I can think of a couple friends off the top of my head that have had this idea for five years but it’s still an idea. It doesn’t mean you have to do it but either you’re going to stop talking about it or you’re going to do something and then you’re going to get real feedback. What else?

Audience 7: A question for DC, have you found any unique challenge or approach to the company differently being that you’re both founder and CEO at Drift?

David: Good question.

Dave: Have you done anything differently because you’re a founder and a CEO?

David: I’m sure I have, but I didn’t know what I’ve done differently. My view on what we’re trying to do as founder and CEO, how far out our mission is I think is different because of founders. We have this vision that takes us the longest time to get there. I think that’s different than just founding something like I have in the past and not being CEO. I’m really thinking about long bets on people, that’s probably number one.

Dave: Investing things now that might not pay off today that have to compound.

David: They were doing them because they reinforce some value that we think is important to us.

Dave: Speaking of that, I want to ask about your entrepreneur thinking ahead side of things, we got a little bit of time left. Right now, you say, there’s two megatrends, there’s two big trends that everybody should be thinking about, worrying about, waking up and thinking about. What are they?

David: This is in the context of marketing and selling, it’s video and messaging.

Dave: I think it’s in the context of building your business.

David: Yeah, everything. I think it’s video and messaging, because I think about it from marketing and sales standpoint all the time. I think we got to look at where attention is shifting and attention is constantly shifting. In my life, it’s been shifting from a channel perspective all over from TV to the internet to eventually video now and messaging and all these different channel types.

If we look at just behaviors, this is how we started on the idea which is Drift today. We just looked at what’s different now that wasn’t five years ago or three years ago or whatever. It was because of these, we were just looking at where people were spending their time. People were just proportionally spending, I thought, their amount of time on some form of messaging whether it’s through IG or messages or Snapchat or whatever. Just think of the amount of time that you spend just personally on that.

The other one is consumption of video, whether it’s YouTube or stories or whatever. Because of that, that means we need to rethink how we communicate to people inside the business going out if people are spending their time there. Many of us may be still thinking about reaching them through old channels but that’s not where you would spend a fortune anymore. Because of that, I think, everyone needs to be thinking about what’s my video, what’s my messaging strategy. Just like 10 years ago we were thinking about what’s our Google strategy and what’s our Facebook strategy.

Dave: I think we got time for maybe one or two questions if people got anything else.

Audience 8: What day do you have to let the most of your progress?

Dave: That’s a good one. What day do we have to let the most of your progress?

David: We talk about mornings a lot and we have a morning club going at Drift. I didn’t know that, Michelle showed me that.

Dave: Everybody’s in now. What’s it called?

Aundience: Morning glories.

David: I think it’s a group that wakes up super early. They text each other at 5:00 in the morning or 4:30. I wake up pretty early, DG now wakes up pretty early.

Dave: I had a routine until two months ago.

David: For me it’s reading in the morning, I’ve done yoga, just like 20 minutes of yoga everyday now for two years, I think.

Dave: It’s an app.

David: I track the number of days. I started up today doing that, I do reading, there’s a whole bunch of stuff that I do in the morning but it’s basically around being intentional in the morning.

Dave: The question was pretty good, how do you think that impacts your success or progress?

David: I believe it’s day by day, all the stuff is day by day, everyone wants to fast forward. My thing has always been if I can get a little bit better every single day because I learn one new thing or progress somehow, all of those inches will add up.

Dave: You only have time to read for ten minutes.

David: Yeah, often that’s only 10 minutes but it will add up and it will compound over time instead of saying, “I need to read the entire book today, this week,” or whatever. I just read every single day, do yoga everyday, and do a whole bunch of other things. Dave has his own morning practice that he does. I’m introducing new things into it and testing and seeing if they stick or they don’t stick

But then I started intentional, I don’t start frenzied in the morning, checking email and freaking out first thing in the morning. I have this moment of peace. Now, a couple of people on the team have it, Aaliyah, again, we talked about before, now wakes up at 4:30AM.

Dave: Every morning for the last two weeks, he’s posted an Instagram video 4:44AM.

David: He can’t stop. Be intentional, I think that’s the habit.

Dave: It just changes the rest of the day. If you get that stuff done in the day, you’re not coming home from this at 7:30, 8:00 tonight being like, “Oh, I didn’t do that thing today.”

Audience 9: As a fast growing startup, when do you think about building culture and the makeup of your company? Do you feel responsibility to do social good and how do you implement it?

Dave: Do you feel responsibility to do social good?

David: Yeah, that’s deep. That’s a good question. I think yes, of course. I think it’s personal for Aaliyah and myself, we’re cofounders. The way that we think about Drift is that whatever happens with Drift, huge success, the reason that we’re doing it is that we hope we can get back basically everything to social good. I haven’t talked about that.

Dave: But I think the difference between you guys that I’ve seen is you do a lot of stuff behind the scenes that nobody knows about versus making a press release every time you donated money or did something.

David: I’ve never talked about it but I’ve been fortunate at Drift. My plan is 100% of whatever happens goes to social good. But we definitely thought about things like becoming a B-Corp and all that kind of stuff, it’s just too early for us to do any of that.

Dave: That’s one of the reasons why we talk about Patagonia a lot. Internally, if that’s real, possession of Patagonia, even though we build business software, I think, internally we don’t think of ourselves as a B2B SaaS company, it’s more like we want to be a brand, like Patagonia is a brand. I think a lot of that stuff is embedded in the DNA of those companies for sure.

David: The hard thing is that it’s incremental, it’s hard to see it everyday. You got to build yourself there.

Audience 10: You talked about bringing oxygen to ideas, how long do you focus on great ideas that doesn’t gain momentum?

Dave: How long do you focus on a great idea that doesn’t gain momentum?

David: I don’t think we think of any idea as great, that’s an important qualifier. I don’t know, I don’t think we have a specific time frame on stuff, we’re pretty impatient on things but we measure everything by getting customer feedback. I think if you’re open to listening, it comes pretty clear, pretty fast when something is not going in the right direction. I think it would be weird if we spent more than three months in any given direction and it wasn’t paying off.

Dave: Especially today, there’s so many ways to get feedback on something, you could find that really quickly. We talked about a lot, you just have to have a gut feeling on a lot of things. People are going to tell you, one great example is this podcast. We never measured it, we never set out to generate leads from it or business but I can tell you that every candidate that walks into our office is like, “I listen to the podcast.” People downstairs, “Oh, I love the podcast.” There’s things like that, you just know. We never set out to measure that and get feedback on it.

                      I think a lot of people don’t do things that just feel right, sometimes. They worry about, “Can I get enough people to be interested?” You just have to do it and see actually what happens. There’s so many different ways you can get feedback from people today.

David: The number one problem is that people don’t want to reveal their ideas. They spend way too long working on it because they don’t want to get bad feedback.

Dave: No one is going to steal your idea.

David: They don’t want someone to criticize their idea.

Audience 11: You talked about role models, that’s great, does Drift have a role model and has it changed over time?

Dave: I want to tell you all of them publicly but internally we have a page with benchmarks of every… Will, on our team, put it together, it’s benchmarks of every single SaaS company, basically over the last 10 years, 20 years, revenue in year 1, revenue in year 2, revenue in year 3, employees year one. Internally, there’s not necessarily one company that we look at but we care a lot about those benchmarks. It could be, “We’re hiring a new marketing person, what should our team mint be at this stage? What did this company do in year two based on where we’re at right now?”

David: We look at those benchmarks a lot obsessively just to make sure that we’re pacing those companies. It’s not like they have some secret but if you look at all of them, there’s trends that you see in terms of ratios of people and what have you and cost and revenue. We want to make sure we’re on track there. I think there’s aspirational companies that we look at, Patagonia is one of them. I don’t think there are many in B2B SaaS that would be on our list that we look at.

Dave: That’s a big part of why, I think, that you guys push to do that is because if you want to do something extraordinary, not like anything else, if you just look at the comparables on the same industry, you’re going to wind up just like everything else. We might look and say, “What did Patagonia do? How did they launch a conference? How did they start this movement? How we can apply it to what we’re doing?” That might be one. Or we might look at the companies in the industry like, a company that’s blowing up right now is Zoom. We’re like, “Wait a second, web conferencing isn’t new, it’s been around forever, it’s a huge pain in the ass but everyone is using and talking about Zoom. What did they get right?”

                      We might ask those questions and go dive deep and say, “Oh, they did this thing.” How can we pull those things and apply them to Drift? That must’ve been a good answer because you’re taking notes now.

David: We pick out different traits in different companies. I look at Google for certain things, one thing actually, which is that they’ve been clear from day one, not with many people but if you knew them internally, they’re basically a data collection and processing company. If you look at them from that lens then every product that they’ve ever launched makes sense, even if those products don’t make any money and they’re loss leaders for them, they make sense because they reinforce. Just like Apple is a hardware business and the App Store, they don’t care about revenue in the AppStore because the reason that the App Store exists is to sell more thousand dollar phones. It’s to reinforce that.

                      I look at Google and say they’re clear on data collection and because of that they can build certain products. We want to be in the middle of every conversation that our business has with customers. We will therefore build products that may not make sense standalone or even standalone but they may reinforce that thing that we’re trying to do.

Dave: Thank you everybody for coming out. We really appreciate it, it’s a lot of fun.


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