#100: Greatest Hits, Vol. 1

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This is a podcast episode titled, #100: Greatest Hits, Vol. 1. The summary for this episode is: If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. ----- For the 100th episode of Seeking Wisdom, we thought it would be fun to pull together some hits -- roughly 10 clips, 10 minutes each, for 100 minutes of the most popular episodes of Seeking Wisdom. Here's the full rundown: 0:48-5:37 - How SW came to be from EP #86 Live at WeWork 5:39-13:43 - Highlights from #2 Learning Machine 13:46 - 22:44 - Highlights from #93 w/Pat Grady on First Principles and Advice for Startups 22:47-45:34 #19 on Carrying the Water 45:35- 1:01:43 - #90 w/ Patty McCord 1:01:44 - 1:05:07 - #51 How To Run A Meeting 1:05:09-1:10:20 - #6 On Hiring Product Managers 1:10:21 - 1:16:57 - #36 How To Work 1:16:58 - 1:30:55 - Books That Have Had The Biggest Impact 1:30:57-1:38:26 - #95 With Brad Stulberg 1:38:28 - 1:39:18 - #28 How to Come Up With Better Ideas 1:39:21 - 1:40:54 - 6 Stars Only! The only question now is: what will be on Greatest Hits, Vol. 2?

Dave Gerhardt: Hey, what's up everybody? A very special episode today, episode 100. It is episode 100 of Seeking Wisdom and we thought we'd do something a little bit different. DC and I have a ton of good stuff coming up for you. We got some awesome new guests, some interviews coming up, and we're going to go behind the scenes on a couple of different things that we do here at Drift, including like how to say no to meetings. I think that's the next episode that we're going to do. But for this episode, episode 100, we had our homie Patrick, who's been helping us out with some production and community behind the scenes who was like, " Hey, what if I grab the 10 best episodes of Seeking Wisdom, mash them all up into a clip, make it about 100 minutes long for episode 100? I was like, " Love it. That's an awesome idea." So that's what we have today. We'll put everything in the show notes for all the timestamps and clips that we referenced. But this is a special episode of Seeking Wisdom in honor of episode number 100. We got lots of growing and other stuff to do, so 100 is just the beginning. Thank you all for the support. We appreciate it. We love doing this podcast every single week, so let's get to it. I'll stop ranting. Here is roughly 100 minutes of highlights from Seeking Wisdom. If we miss one of your favorite episodes, tweet at me @ davegerhardt, @ dcancel and let us know what you wish you heard. Here it is, all right. I'm ready if you're ready.

DC: We're ready.

Dave Gerhardt: Everything is set up. Everything is looking nice. All right. Will you turn our levels down a little bit because his are jacked up because his mic's are better.

DC: Are we back?

Dave Gerhardt: Yeah, we're back.

DC: Damn. I miss you, guys.

Dave Gerhardt: I want you to do the intro because we had another guest. We had another visitor here for lunch at Drift.

DC: You keep bringing the heat? Bringing more guest?

Dave Gerhardt: People said they love the inside look. They felt like they were hanging out with us having lunch in the office, which is awesome.

DC: Now, that's the point. That's the whole theme. That's the whole feeling we want for Seeking Wisdom, feel like you're here with us hanging with us.

Dave Gerhardt: Right.

DC: So we're going to do more of these things. Luckily, we have some cool friends, some cool people we know that we cannot talk into bringing them in and sharing what they know with you guys. 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 listen to the podcast. They listen to the two of us talk and they're like," Wait, that's just the podcast." Is this the only difference?

Dave Gerhardt: We're just having this conversation 10 minutes ago.

DC: Yeah. So we were having these conversations and I think I told you at some point that I was thinking of recording a podcast, or I was recording some of these conversations. Then you pulled me into a room one day to try to make this into a podcast. The context is, DG, he had his own podcast. That's how we met. He was doing podcasts on HubSpot before that.

Dave Gerhardt: Yeah. If you listen to the podcasts, which a lot of you have, you know that DC doesn't really remember anything, so I'll tell you what actually happened.

DC: Okay.

Dave Gerhardt: That's partially true. But the cool thing was I remember talking to you during the... I had this podcast Tech In Boston that I did on the side and that's when I interviewed you and that's when we met. I was like," This guy's really mysterious, but I can get a lot. I can get what he's saying." Then I found that you guys were hiring a marketing person. That's how I ended up working at Drift. But 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?" I was like," 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."

DC: That's true.

Dave Gerhardt: We had, it was probably like three or four months into doing marketing at Drift. One of our advisers, [ Heaton Shaw 00:00:03:50] who has a lot of followers on Twitter, if you're on Twitter, serial founder, done a bunch of companies, but he said to me, he's like," 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 a CEO. He's super busy. Doesn't answer his email. I can't get him to respond to anything. How am I ever going to get him?" The default form of content for most people is like," Oh, he's going to write." So I remember thinking like, there's no way I'm ever going to get you, and this isn't just you. This is every exec or founder entrepreneur. There just aren't enough hours in a day for you just sit down and write a blog post. But every night, you would send me something on Slack and I'll just be like," Damn, this would be a killer blog post." Or text me at 6: 00 in the morning about something crazy. I was like," What can we do with this? Oh, shit. Maybe we should do this podcast and get you an audio format so then you can just go."

DC: Yeah. Do you want to know the secret?

Dave Gerhardt: What's the secret?

DC: I haven't told you the secret.

Dave Gerhardt: What?

DC: When I met you... so Dave interviewed me for his podcast. My secret plan was when Dave came back and wanted to work at Drift, which is a whole another episode, we should do that.

Dave Gerhardt: We should do that.

DC: That was crazy.

Dave Gerhardt: Yeah.

DC: I thought-

Dave Gerhardt: He wasn't going to give me an offer until I came back from my honeymoon. I said," I'm not leaving until I get this." Then I went on my honeymoon. Then Leah literally told me today, she was like," Thank God you weren't working on our honeymoon. I couldn't deal with you looking at your phone the whole time."

DC: So he came in and we did this interview on his podcast. Then 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." Then he texted me or called me and he said," No."

Dave Gerhardt: I said no.

DC: And I said,"Why?" He said," I'm coming right over." And he comes over, we were just across the street, and says," I'm not moving until I have an offer-

Dave Gerhardt: Seven yard walk.

DC: ...because I know what'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 spirit.

Dave Gerhardt: Wow.

DC: But here's the secret that you didn't know.

Dave Gerhardt: You do remember things. That's incredible. I'm like crosstalk

DC: The secret was when I met you and we did the podcast and then you were doing The Growth Show before that, I thought," Okay, Dave's 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-

Dave Gerhardt: Totally.

DC: ...and he wants to do something new, something the Lord had made." I made it seem like it's his idea to do the podcast.

Dave Gerhardt: Damn. [crosstalk 00:06:30]

DC: So that is the secret.

Dave Gerhardt: I need a minute.

DC: Yeah. That's the secret move.

Dave Gerhardt: That's crazy.

DC: That's called 3- D chess.

Dave Gerhardt: That's called 3- D chess. That's crazy because there's so many things that we've talked on this podcast about in hiring.

DC: Yes.

Dave Gerhardt: Right? The traditional thing would have been like," Oh, he's done podcasts before, let's hire him to do a podcast."

DC: Totally. So I went the other way. I went with the neg 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." Then I'm going to plant enough things that eventually you just say," Let's just do a podcast," and we did it.

Dave Gerhardt: And we did. Damn, that's crazy. I had no idea. That's pretty good.

DC: Evil.

Dave Gerhardt: Evil genius. We live in this world where everybody wants to be smarter and more productive, but you know. Whether you want to be a better cook, maybe you want to be a better marketer, maybe you want to be a better CEO, everybody has this urge to be smarter. But you notice this thing all the time from the average Joe to the Ivy league MBA, people just stop learning after they get out of school. You notice this over and over. Once you leave school, learning is done.

DC: Yeah. This is the thing that I notice that happens the most. I think this is the thing that you can use as your secret weapon to beat everyone around you, and that is to continue to learn.

Dave Gerhardt: People like Elon Musk, Warren Buffett, they get credit for being these really smart guys as they should, but a lot of people don't know the thing that they don't get credit for is that behind the scenes, they're always learning.

DC: Yeah. I think that's the hidden secret for all those guys, whether it's Gates or Buffett or Musk or any of the famous people that you think of as inspiration. What their secret is is that those guys are reading more than anyone else.

Dave Gerhardt: The whole thing is they just become like these learning machines, just learning from other people. You've said this, at least to me, a bunch of times. People always say," This is your fifth company. What's your hack? What's your shortcut?" and you always say that your only shortcut is just learning.

DC: That's it. That's the one thing that pisses me off and gets me frustrated is when people are always asking for hacks and tricks and shortcuts. I get it. We all want to get there faster, but the only shortcut that I've ever found is continuous learning. There's lots of ways to do that whether it's through mentors, whether it's through friends, whether it's through experiences, but I found the most efficient and the highest ROI comes when you lean on books as the way to learn.

Dave Gerhardt: All right, so this is funny because everybody wants this. We live in this world of hacks and you're sitting here in 2016 telling people that they need to read more books.

DC: Yeah, read more books. Forget about reading about posts about hacks, about hacks, meta posts, posts about hacks, about other hacks. The real hack is just read books and learn.

Dave Gerhardt: So the secret sauce is these guys have all become these learning machines. The reason they become learning machines is because they put in the work. They do the reading. But the focus of this today is give some people advice for reading more. Somebody is going to say," Okay. Yeah, listen to David's podcast. He told me to read more. I'm busy. I don't have time."

DC: Yeah, everyone's busy. I'm busy, everyone's busy. I get it. I think you need to prioritize reading. I have a little system that I use personally to get more reading done.

Dave Gerhardt: All right. I want to start with maybe when you actually read. We'll talk about the ways you read after, but when do you make time? You're a CEO, you have a wife, you have kids, you work long hours. You got to put in the work at home and the office. There's minimal time for you to... When do you actually get your reading done? Do you have a spot?

DC: Yeah, most of my reading happens early in the morning. So I get up at around 5: 00 AM each day and I do a couple of things, but one of the most important things that I do before starting my day, before touching the computer, before touching my phone, and before even my kids and wife wake up is to sit down and read.

Dave Gerhardt: Why can't you touch a device? Is it if you touch the phone and touch the computer, then you're gone?

DC: Yeah. crosstalk

Dave Gerhardt: For me, that is gone.

DC: Exactly. The second I touch a computer or phone, then my mind is racing elsewhere. Part of my morning ritual or practice is to do yoga and really be intentional about my time, and part of those intentions are to sit down and read.

Dave Gerhardt: All right. So for you, it works in the morning, but maybe like the bigger takeaway for most people is it doesn't have to be in the morning. It's just you have this dedicated time. You know this is my time.

DC: Yeah, just based on my schedule because I'm always running around and kids and startup and this and that. The most consistent time I can find is early in the morning. I'd say for other people that I talk to, for them, it's riding the T, riding the train. For others, it's doing audio books in cars. For others, it's late night before bed reading. Everyone's got something that works for them. What's worked for me is early mornings.

Dave Gerhardt: But the other thing is you don't have to make it. Reading doesn't have to be this hour, this marathon thing, right?

DC: Oh, no.

Dave Gerhardt: Can be 15 to 30 minutes.

DC: Yes. Most mornings, I'm reading 15, 20 minutes is all I need to read. Sometimes I go longer than that, but if I read 15 minutes, I'm happy.

Dave Gerhardt: What is it that's so good about a book? Is it just you're able to learn from somebody who has spent hours and hours and hours and months writing a book?

DC: Yeah.

Dave Gerhardt: You just extend kind of your lifetime a little bit by reading that.

DC: Yes. So the wide books versus articles and posts and stuff like that, I think it's more considered. There are millions of books, so I will not say all books are great, but usually, the stuff that I'm reading, the stuff that most people are reading are things that have been recommended and have stood the test of time, whether that amount of time is a year or five years or 10 years or 50 years. They've stood the test of time and so the stuff that keeps coming back and bubbling back up is worth having in that format.

Dave Gerhardt: One of the push backs that a lot of people say about reading is they read 20 pages and it's just boring, and you're done.

DC: Yeah, I used to make this mistake all the time, which is I used to think buying a book was this big thing. When again, in reality, you're spending between eight to 15 bucks on average for any book that you buy. But I created this big source of anxiety for myself and said," Oh, I bought this book. I'm bored after 20 pages. I must read this book. I got to finish it. I got to read the covers. I need to read the table of contents. I need to read the intro or the epilogue," like I need to read every single piece of it. What I figured out is one, you need to give yourself permission to not finish books. There're certain books that you don't have to waste your time finishing. You may come back to someday and want to read again. Today might not be the right time to read this book. All you need to do to make a book worthwhile is to take one lesson out of the book. If you can learn one thing that you didn't know before from reading this book, that is$8 well- spent. That is eight lottery tickets right there.

Dave Gerhardt: I wanted to remind you to say that. That's been the best lesson, which is you don't have to get caught up in trying to comprehend all 300 pages and you have 40 takeaways and then write a five page paper on it. You said," If you can pull out one thing from a book, then that book was worth the eight to 10 bucks for it."

DC: Absolutely. I've taken many classes in school that I couldn't take one thing out of. So I just think I was talking to someone the other day on our team. Hey, Ali. He read Managing Oneself, a book that I love, by Peter Drucker. It's a small book. It costs like six bucks. He said he loved it. He enjoyed and he said like, " I really took away this one lesson from it." And I said, " That's all you needed." You just had the highest return on investment on six bucks that you will ever have. You have one thing that he has implemented and is totally changing the way that he works.

Dave Gerhardt: It also helps you read faster too. You're not stressed out about every little single detail.

DC: Yeah. Reading a book is not memorizing a book. With most books that matter, I end up reading them two, three, I've read some books four, five times. The reason for that is that you have to be in the right context to get the right lesson out of each book. So the first time you read it, you're coming into it with one-

Dave Gerhardt: We talk a lot about trying to think from first principles because I think starting a company or being an investor has a lot of scaffolding that's been built up around it over the years, which is useful because in a lot of cases, that can help you shortcut to an answer as opposed to have to doing everything from first principles. But I think for us, when we invest in a new company, we're trying to only invest in what we would call sort of fundamental companies, meaning they have a chance to be independent for the next few decades. Like they have a chance to completely define a category and dominate that category and show the world something that the world didn't know before they existed. For those companies, a lot of that scaffolding doesn't really matter because by definition, that scaffolding is conventional wisdom and conventional wisdom builds conventional companies. So we just try to go back to first principles like, what problem do you solve? Why is that important problem? Are there really a lot of people who have that problem? What positions you to solve it in a unique and compelling way that won't be easily replicated by everybody else who witnesses your success?

DC: Yeah. First principles is like one of these things that is, it's so logical when you hear it, but it's so hard to apply it in the heat of a deal or the heat of battle, the heat of some competition or something like that, especially in your world, everything's competitive-

Dave Gerhardt: Yeah.

DC: ...highly competitive deal.

Dave Gerhardt: Will you explain what first principles are in your context? As for us, it's customer company then us. What does that mean for you from an investment perspective?

DC: Yeah. First principles for us, in the context of a company, it means if you reduce it to its essence, why do companies exist? Companies don't exist to make people rich, whether those are the founders or the investors or anybody else. Companies exist to solve a problem. So for us, the first principle is just, what is the problem you're solving? How do you do so in a unique and compelling way that has some inherent durability to it? For us, those sort of are the first principles. How that translates into going after an investment? One of the biggest things we look for is just authenticity in a founder. Because if somebody makes a list like," Here are the 100 businesses that maybe I can build. I'm going to try a couple of them, but maybe I'm going to settle on business number 37," that's fine. There are probably a lot of situations where that ends up working out. But you might not have same level of passion in attacking business number 37 as you do when you attack a problem that you've actually experienced, and it really ticks you off that that problem exists and you just want to stamp it out of existence.

Dave Gerhardt: Yeah.

DC: The authenticity with which somebody approaches their whole business, I think they can't help but translate that into their employees and into their customers. Then you have this groundswell of enthusiasm that propels your business forward.

Dave Gerhardt: I know a guy like that.

DC: Oh really?

Dave Gerhardt: Yeah.

DC: Somewhere?

Dave Gerhardt: He is, yeah. Do you want to talk about first principles thinking Don Valentine is-

DC: Yeah, it's just so simple.

Dave Gerhardt: ...canonical example of people who are going to listen and be like," Who's that and what was his crosstalk?" Don Valentine was the founder of Sequoia in 1972. What was interesting about Don was he was not a financier. He was a chief marketing officer at a time when marketing went to everything associated with going to market. The founding premise of Sequoia was Don just saying, " Boy, I'm surrounded by all these brilliant engineers who know how to build great stuff but don't necessarily know how to connect it to human problems." That was the Genesis of our business, and that's then what we've tried to stay true to over the last 45 years.

DC: That's amazing. So that goes back to the authentic founders, right?

Dave Gerhardt: Yeah.

DC: The big markets? Then he talks about this thing of just target big markets. Just like it's so fundamental. I'm doing an injustice, you have to watch it. He's funny in the way that he delivers it, but it's a thing that we always forget, all entrepreneurs forget is just the importance of targeting big market.

Dave Gerhardt: It's tricky though, and it's a little bit dangerous because I think anymore, you don't target a big market from time zero.

DC: No.

Dave Gerhardt: You target a very, very narrow slice of a big market and you earn the right to evolve your way into more of it over time. So I think for us as investors, one of the most common mistakes we make is we underestimate or under- appreciate what a market can become when things start to work. As a result, we just don't realize how exciting a business is the first time we see it.

DC: Yeah. It's something we talk about internally all the time. It's just like it's our own go to market, is just like wedge. We got to start with something that is easy, simple, everyone can integrate it. It's nonthreatening. Nonthreatening is the word that we use. Then that wedge, over time, gives us the ability to maybe rethink all this other stuff. But we're capturing a tiny little wedge in the beginning and then expanding over time. It doesn't mean that we don't have a big vision for where we're trying to go, but we need to find that little crack to get inside. That's non rip and replace, non- threatening, it fits right in there.

Dave Gerhardt: The wedge that you talk about a lot, it actually starts big and then you get to the wedge. You love the whole invert. Invert the problems, invert the challenges that we have and then say," Okay, that's the big problem, but what's the easiest path for us to maybe get into that market or into that company?" and that's how we started small.

DC: Mm- hmm(affirmative). Since you look at so many companies, what would be your advice to young, budding entrepreneurs about how to think about their companies?

Speaker 1: About how to think about their company just in general?

DC: Yeah. I don't know if that's the- In today's context. Let's take a SaaS company for example, not a scientific risk kind of company, but just a market risk company, like someone in SaaS or some kind of software. How would you be thinking about that category now, or that type of company now versus five years ago? Like what are the risks?

Speaker 1: Good question. I guess broadly speaking, and then maybe I'll zoom in on SaaS a little bit. Broadly speaking, we've been in the same basic technology cycle since 2001 now, and so we're called 16 to 17 years in. Historically, these cycles have followed 14, 15- year patterns. In some ways, we're kind of overdue for the end of this cycle and the beginning of the next. What that means for a founder, generally, is what we would call the verrückt period. Verrückt is a German word which means insanity or craziness, what Don Valentine would have called the good theater that comes at the end of a cycle.

Dave Gerhardt: The good theater, yeah.

Speaker 1: The verrückt period is probably coming close to an end. That could be tomorrow, that could be five years from now-

Dave Gerhardt: Yeah, right.

Speaker 1: ...but it's probably coming close to an end. The way that translates into the advice that we give to founder is don't get caught up in the hype. Don't try to chase the unicorn logo. Don't raise infinite amounts of money just because it's available. Just try to stick to first principles because if your employees actually care about your mission and if your customers are going to buy your products regardless of whether or not their budget is big or small, you're in a good spot. We would actually encourage people in most cases to raise less money as opposed to more, to be very deliberate about the hiring, and try to stay away from the people who respond to the line," We're a fast growing crosstalk company," and go after the people who respond to the line," We heard about solving this problem. It's hard, but we think it's worthwhile. If you agree, you should join us."

DC: Yeah.

Speaker 1: Right?

Dave Gerhardt: We are going to change our job descriptions.

DC: Yeah.

Speaker 1: Yeah. Then I think for SaaS specifically, that's also true because five years ago, there was still a reasonably decent amount of white space in SaaS just in terms of buying centers within the enterprise that were underserved or SNDs for that matter that were underserved. I think today, there's less white space and so the companies that are cracking through are the companies that have come up with something that's truly a superior value proposition. Either it's more usable or it's more pervasive or it's more intelligent or whatever the case might be. I don't think you can brute force your way into scale today the way that maybe you could five, six, seven, eight years ago. Today, there's just more competition. Everybody's got plenty of money. We're back to the basics of find the magic of product market fit and iterate from there.

DC: Those are wise words for you entrepreneurs out there.

Speaker 1: It's easier said than done.

DC: I know. Everything is easier said than done. That is true. All right. So we're going to talk about carrying the water. Basically, that's a note saying that most of us know, which is for people when they're getting started early in their career to actually spend time carrying the water of those above them, whether that's mentors, whether they're the people in their workplace, whoever it is, and basically learning through the age- old apprentice method. The reason that this came up recently is that we always talk about the grind here and I noticed something when talking to other founders and other people of a certain vintage, aka old, that it seemed like a lot of people that they were dealing with at work or their colleagues who were just out of school, fresh out of school, had a different set of expectations for how quickly their career would progress.

Dave Gerhardt: Yeah. So when you mentioned this idea, when you mentioned this to me, I didn't know what you meant by carrying a water at first, and then you explained it to me. I'm a big sports fan and so the analogy for me was a lot of times, the rookies at training camp on a hot, 100-egree day, they got to carry the pads, excuse me, of the veterans after practice. They got to carry their shit, bring it into the locker room. So that's what you said. You said," Yeah, it's that."

DC: That's true in sports, in the military, and in way long ago, and in the workplace as well.

Dave Gerhardt: Like doing things for your parents.

DC: Exactly.

Dave Gerhardt: There's so many things and we're going to talk about all of them because this is a topic that gets me fired up. But you basically were just saying early in your career, we talked about this back and forth, earlier, you have two jobs, right?

DC: Mm- hmm(affirmative).

Dave Gerhardt: You have a job but you have to do your work.

DC: Yeah.

Dave Gerhardt: Right. You kind of have, you have a job, you have to do your work. You have to be good at your job, whatever. You're a designer. You have to be amazing designer. You've got to create value for the company and value for your customers. But you also have a second job, which I don't think a lot of people understand. And the second job is to make the rest of your team and your manager, your boss, look good and be successful. And it's not just about looking good, but it's like putting them in a position where their life is now easier because they've hired you. And, I think, the biggest thing that people just forget is they completely forget that step. But it's a hard thing to talk about because we were just at lunch and we were talking about this. We also don't want to come on here and say, you are at the mercy of your boss. And your job is to clean up their shit.

DC: Yeah. Because I think it's true at both ends. So, getting started, I think, you should be focused on making the company and your boss, whoever that is, your manager, whoever it is, your team, look better. And give them the credit. But I also think on the other end, as you progress in your career, and as you become a leader, that your job is to help those younger than you, those around you look good and not yourself. So, I think, it's not just younger people, but I think, even as you become more experienced, your job should always be to make those around you shine.

Dave Gerhardt: Yeah. And I think, the mindset is, if I'm an employee, how can I do my job and also take as many things off the plate of the person who manages me.

DC: And, I think, it's going back to your team idea there. It's just like, when you see a well- functioning team that everyone's blown away by, they're all individually doing great things, but they're also making sacrifices or assists. In basketball terms, they're assisting other players. And those are the great teams. There are great teams with exceptions where there's one dominating player, but usually, that's not the case. Usually that's the exception. And usually, the rule is, a great team is everyone is contributing to bring the team forward.

Dave Gerhardt: All right. So, for people listening, I'm 29. I graduated...

DC: He's a millennial.

Dave Gerhardt: I'm a millennial, graduated in 2009 and started working.

DC: The reason I mentioned he's a millennial is that it's unusual for millennials to be as in touch with this subject as David's.

Dave Gerhardt: Yeah. Well, anyway. So, I totally get, I understand this. And I think, since then, right around that time, 2009ish, why do you think this started to happen? You mentioned to me, it's the Zuckerberg thing. It's because, everybody that graduates college now thinks that they can start a company and be their own boss at 22.

DC: I think that a number of things have happened. In my opinion, and who knows if they're true or not, but some things which may be correlated, all of a sudden, you're being brought up in an era where very young founders and celebrities, basically, celebrities all types. Some of those celebrities being founders are being celebrated by our culture. And that could be a singer, an actor. That could be Zuckerberg, himself, in technology. But, all of a sudden, you're seeing the example, public examples, which we didn't see in the past of 22 year old, 20 year olds, Justin Bieber, 16 year olds being phenomenally successful. And the media loves to focus in on those people because they are so exceptional, because that is actually so not normal that we begin to grow up in an environment where we made think those things are normal.

Dave Gerhardt: And part of the thing is, part of the things that make millennials often great teammates is because they think they can figure anything out. And that's the mindset. I can figure anything out. I can figure this out, let me do it. I don't have experience, but let me do it. And, that is an amazing quality. But at the same time, it's also exactly what we're talking about here. And it's that mindset that I don't have to carry the water here because I'm a person just like you and I can contribute.

DC: What year did you start working?

Dave Gerhardt: I started working right after I graduated.

DC: What year was that?

Dave Gerhardt: 2009.

DC: Okay. That's important. I asked that because, I think, Dave and most people that we're probably talking about have graduated 2009 or more recently. And the reason that I think that's important is the second reason. I think that, this may be occurring more often than not is that, these people have come into a workforce, in a workplace where there has been no downturn. The last significant downturn that we had economically was 2009. So, if you came into workforce after that, you've never seen an environment where things have been rough. You haven't been through those rough times. And I think, for the people who are self- aware like Dave is on the subject, they've probably seen some rough times. They probably been through the trenches to some degree. And so they have some context.

Dave Gerhardt: Yeah. I think, for me, it was because I graduated 2009 and 2008 was a shitty year. That was my senior year in college. And, that was the weirdest I've felt in my career, actually, even though I hadn't done anything, it was because everybody says, you got to go to college, you can get a job. I know you have opinions on it, but that's separate thought. But then when I graduated, they were like," Oh yeah. We're looking for somebody with two to three years experience." And I was like," How the fuck do you get experience if you can't get a job? So, I took a internship.

DC: Okay. Talk about that.

Dave Gerhardt: Yeah. So, I didn't know what I want to do. I knew I wanted to be... I graduated with a marketing degree, which has absolutely nothing to do with anything I've done in my career. I do marketing now, but it has nothing to do with anything I learned in college. And so, I took this internship at an agency, a PR agency because it was the only place that would hire me and I thought I wanted to do business. And so, I figured this would be a good way work with all these tech companies. I think, that actually had a lot to do with the way that I think now because of the agency model. When you're 20, I was 22, I don't get to talk to clients. Nope. So, everything that I do has to go through somebody else. inaudible When I was intern, emails that I'd write, if they were client facing, somebody would have to review them first. And so, I think, that forced me to be like," Okay, Dan. There is a clear ladder here." But once you can show that you can do it, and so, it was kind of on me like," Okay, if I don't get to do any of this client facing stuff, how can I make other people that get to do this? How can I make their jobs easier?" So, then I get to do it. Yeah. And so, it just became scheduling meetings for people doing all the other shit like scheduling travel and putting stuff in Excel that nobody wanted to deal with.

DC: And were you paid well at this internship?

Dave Gerhardt: It was fucking terrible. I've got$ 10 an hour. And I was living with my parents house, which is in Worcester, which is 45 minutes away from Woburn where this internship was.

DC: So, you commute in 45 minutes. crosstalk.

Dave Gerhardt: 120 miles round trip everyday.

DC: There you go. Now, I think, I understand why Dave has some context to this and I don't think many people have gone through that.

Dave Gerhardt: I don't want to forget this thought. So, the point of that story was to say that now, all the companies that people want to work at, there weren't as many drifts or other startups. And so the problem, the challenge is that, now, if a startup is your first job or all these tech companies. You think that work, it's 10 people sitting around listening to rap on the Sonos and there's a tap in the office. You think that that's what work is.

DC: Nope, no one's working that way.

Dave Gerhardt: How do we change that though? Because like at the same time crosstalk

DC: I love everyone's opinion on how you change that. I don't know because, and maybe, the change has to come from someone like Dave, because I feel like when, if I'm to say that, then I'm the old man on the hill. Back in my day, you had to work. crosstalk.

Dave Gerhardt: Whoever says it is shitty because, excuse me, even if I say it, it comes off as I want people to be... There's rules and you're not allowed to talk because you're in this role and I'm crosstalk

DC: Definitely not. But yeah. But we have to have some context to understand that, the kegerator, and the sitting around together and having a good time and doing outings and doing all the fun stuff that we do as a team, as all of us do, as it is teams, especially in startups and early technology companies is not normal. It's not normal at all. But, that's only been the only experience that you've had, it's hard and it's hard to have context. And I don't know how people crosstalk.

Dave Gerhardt: I think, the most underrated career advice is to join a big company when you get out of college.

DC: I think it's a really good idea. It gives you context and it gives you, you may like it. So, it might be perfect for you. And if you don't like it, then you have a reason or kind of a mission behind your decision to either start a company or just join a smaller company. And it gives you appreciation.

Dave Gerhardt: I think, it depends on what you do. I can understand if you're engineer, might be easier to go join a small company and you have more focused role, but if you're in sales or you're in marketing, I didn't appreciate this while I was doing it. When I worked at two big companies, two big companies before, Drift and [Two-Star 00:35:37]. So, I've done two early stage companies and two big companies. And I think, when you're at a big company at the time, while you're there, you hate it. And you're like, " I want to be at a startup this place." But then when you get that first early stage job, you have subconsciously built in all this process and not the bad type of process, but the way you communicate, the way you share your work, the way you work with others, I think, that's stuff that you can't learn if you just go directly to an early stage company. And so, being in the constraints of a big company where you're one of 150 marketers is actually a really good learning experience, but it's just hard in that moment. I think of it that way.

DC: Yeah. And I think, in our world, that we're kind of in B2B software world, it's important to have context for what is broken today in order to fix it. And it's great to have that kind of beginner's mindset and to come in and not be weighed down by the way that things work today. But it's also super useful to have some context for what is actually broken. Do, actually, people care about whatever it is that I'm building or proposing?

Dave Gerhardt: Yeah. So, from where you are, tell me about the good things that can happen to somebody in their career if they carry the water.

DC: Hmm. So much. Let's see what are the good things. Well, one, you start to, it humbles you. So, you need that humbling. And because the humbling is going to come no matter what.

Dave Gerhardt: From your perspective, you're more likely to invest in that person.

DC: Oh, okay. So, that perspective, yes. I think like...

Dave Gerhardt: You as a CEO.

DC: Yeah. People are always asking for, to get time with whatever, with me or different people, whatever. I don't want it to be about me, but they're like," Oh, I want a mentor. I want to talk to this person. I want to talk to that person." And it's like," Well, first thing you got to do is do stuff for them." People want to get, but they never want to give. So, you got to start with giving because you need to give what you want to get back. Right. And so, you go work, apprentice, mentor, whatever the word is, basically, go create value for that person or set of people. And then, they will give back to you. But to expect that they will give back to you without first grading value, it's unlikely. crosstalk.

Dave Gerhardt: And this happens at companies. I saw this at a company used to work at. Day one, new employee, emails the CMO. Says like," Hey, can we get a coffee? I want to pick your brain." 75 people on this team. Hundred million dollars in revenue. He doesn't want to sit down with you and talk, have a coffee. You've been through the interview process. You're here now. You don't get to pull that card. It's hard enough for other people to get meetings with this person.

DC: When I was back before Drift, I was at HubSpot. And actually, that would happen. I knew when we were bringing in new classes of MBAs, because it would happen every single time. So, I knew when the new class is starting, because I would get all of these emails on. So, every MBA that would start their first day, the first thing that they would do is to send emails to everyone on the executive team and say," Hey, can we go to lunch?" So, first day you're getting all these emails and they're like," Hey, do you have time? Can we set up a meeting for Tuesday to chat?" And I do like, one," Who is this?" Two, I would always reply the same thing. They asked and say no. And then, some of them, a small percentage of them would reply back and be like," Oh, why can't we meet?" And I would say," You need to do something here first. Do something here first so that not only that you create value, so that we all have context or I have context to even understand what are we talking about because you haven't been here for more than 30 seconds. You haven't contributed to the team or the company, but yet, you want to have a meeting. I don't know what we're going to talk about." And so, most of the time, they would always want to talk about, when I did do it in the beginning, just non- sense. They just want to meet for the sake of meeting.

Dave Gerhardt: inaudible about your career.

DC: Yeah. That's why we do this podcast now.

Dave Gerhardt: So, people don't have to meet with you. He just listened.

DC: Exactly. And I could point them back and be like," Go do that." Because every time I would meet them, I'd be like," Oh, we already talked about doing this. Have you done it yet?"" No, I haven't done it yet."" Well, that's your fucking problem." Whereas like, crosstalk inaudible.

Dave Gerhardt: So, this is just a self- awareness thing. Where the right way to approach that would have been," I want to meet with this guy, but I don't have my card to play yet. But I'm on his team. I'm going to bust my ass. I'm going to do a good job. I'm going to make sure he knows who I am. Maybe make a couple of things in his life easier."

DC: Yeah. And those people? Guess what? You go out and you pull those people closer to you because they're exceptional. And so the people who would come in and crush it, man, I'd be running to meet with them. Not only me, but anyone else would be like," Wow, that person is creating so much value that I want to be a part of them."

Dave Gerhardt: Well, you take the other, you take the opposite mindset. You're like," Man, I want to try to get my hands on this person early in their career," versus them just coming to you saying...

DC: Exactly. So, totally underrated, carry the water first, push. And then, people will because it's so not normal. You will stand out and people will pull themselves to you. So, you will create a pull versus trying to push yourself onto them.

Dave Gerhardt: Yeah. So that's some career advice today from us.

DC: Yeah. And so, what would you tell people, other millennials like yourself, who haven't carried the water yet? Why would it be beneficial? How did they do it?

Dave Gerhardt: So, the beneficial part is, you just notice that people take good care of you. That's the number one thing. That's why you should do it. Because if you can take little things off of that person's plate, their life is easier and it's more likely to trickle down to you. It also just shows the self- awareness and, I think, that can be applied to a lot of other things other than the day- to- day job." Oh, this guy obviously gets how things work. I trust him working on X, because he's going to think about it the right way." As far as how to apply that in your job. I think, just remember that you have to, you have two jobs, you have the job that was in the job description on the website that you applied for and got, or whatever didn't apply for but you know the role. You have to do that well. And so, that's check number one. You don't get to earn the right to do all this other fun stuff and hang out with execs if you're not crushing your job. But once you've done that, it's just like, think about opportunities where you can take things off of people's plate. So, whether it's just like, you're in slack, for example, and somebody mentioned your CMO. And they say like," Hey, Bob should go do this." If you have self- awareness, you know that that's not something that person needs to spend their time on. Just grab that, just say, I got it. I'll do it. And, it's a lot of just doing stuff and then telling somebody that you did it like," Hey FYI, I booked this thing for you. Don't worry about it. Here's all the information. Got it covered." That person doesn't have to think. And especially, unless you're at a huge company, that's usually the story that we're telling today applies to execs. It's not usually the director of sales at a big company. It's more about people whose schedules are already nuts and already have enough stuff going on. Any sliver that you can make their lives a little bit easier as it relates to work, whether you see some bullshit stopping it before it gets to them. It's almost like you see a fight with your sibling. You could either let your parents find out so everybody gets in trouble, or you can deal with yourself.

DC: So, I think, the one takeaway, the one thing that I would tell people if they're early in their career and they have kind of a goal," Hey, I want to be the CMOs in there. I want to be the CEO. I want to be whoever you want to be." Or," I want to start a company someday." Whatever your goal is, go and find out, find the person closest to you who has already done that and has been successful at doing that. And then, go and figure out how you can go and carry the water for her, for him, and then learn from that person by doing so.

Dave Gerhardt: And, realize how long it took that person to get there. You shared a story. You said, one time, you've started a bunch of companies, manage hundreds of people. You said, one time, somebody basically jumped five different steps to become an executive. crosstalk.

DC: I think this is something that people don't see. It takes a long time. And so, some people might come out of school and be like," I'm 22, I'm 23, I'm 24," or whatever." How can I be VP of whatever or the CMO in in a year?" When someone is that far out or that far from being self- aware, it's really hard to kind of coach them. But, you can use examples and say, the best case scenario, the person who's blown you that you've seen, or either work with you or has worked around you, who's been the Kobe of their era. It took them eight years, 10 years, to be able to crosstalk.

Dave Gerhardt: And I was like," the best person you've ever seen."

DC: I've only seen one. Maybe, you can be past that person. Probably not. Probably, most of us can be the Kobe of our position, of our generation.

Dave Gerhardt: Yeah. But the thing is, it doesn't come down to, if you're 24, 25, that next step isn't about the work that you've done in the 365 days of that year. It's the experience that just compounds over time. And a lot of times, you can do an amazing job, but you just need time because you need to see more things happen. There's going to be ups and downs. You need to go through all that. It's not like, you just crush it in one year and because nobody has seen results like that, that you just get to be this role.

DC: Yeah. You need time to make mistakes and to learn from them. And you're going to make a lot to them. I'm reading this fantastic book by the founder of... Sam Adams, gym coach. I don't know if I'm saying his last name right. Fantastic book. I think we're going to do a podcast episode in the future about this. Great book. He started the microbrewery kind of industry. He started Sam Adams, which most of us know is a great beer company. And, one thing that he said that he always remembered that his dad told him, and he came from the longest line of American brewers in history. His dad was a brewer, his grandfather, his great- grandfather. His dad told him one thing that he always remembered. He said," you need time to be able to make mistakes. And you're going to start out and you're going to make hundred dollar mistakes in business. Then you're going to make thousand dollar mistakes. Maybe, you might even make it, one day, to make hundred thousand dollar mistakes." And he said," And if you're really lucky and part of the very few percentage of people who get this far, you will someday make million dollar mistakes." And he always thought about that because he did make all those mistakes, including making one multi- million dollar mistake that could have sunk his company, but you will need time in order to make all those levels of mistakes. And it's one thing to learn from a a hundred dollar mistake. But guess what? A$10, 000 mistake is coming up and a hundred thousand dollar mistake is coming up. And that just is a matter of time. You cannot rush that.

Speaker 2: The pattern recognition is such a tough. I feel like the only way to learn that is rep. We call, reps and sets. You have to have done hundreds of interviews. I'll feel it now. Him and I might interview the same person and we'll walk out of the room and I'll be like," Man, I thought she was great. I loved her." And he'll be like," Sleep on it. Tomorrow morning, text me." And I'll be like," Where's he going with this?" And then he'll be like," Did you notice that she said this thing?" And I'm like," Yeah." And he's like," That's exactly like this person and this person and this person."" You're right. But that's not a thing that I've seen."

Speaker 3: Yeah. Here's a tip for you after 30 years of doing this. If you go into an interview thinking about the problem that you're trying to solve, so you hire somebody. So, this is how you get a req approved in most companie., It's either describing the person that left that you didn't want to go a fantasy person that doesn't exist or whatever it takes to get it approved. None of those things have anything to do with why you're interviewing. Because when you're interviewing, you're trying to figure out if this person can do this job. And so, I always equate recruiting like painting. It's all in the prep. So, first, you got to go deep into what is it we don't know how to do? What problem is it that we need to solve? How do we want to round out the team? What needs to happen that's not happening now? And the more you know about that problem, the more you'll start to recognize the patterns. Because, what we do is we interview for fit and here's what fit literally translates to early in your career. I want somebody who's smart, on quick on their feet. I want somebody just like me. crosstalk All the time. And then, you interview somebody and you want to go have a beer with them. So, you figured they're great. And I would say," God, I loved him too. I totally love him. By the way, did he mention his current boss?"" Yeah. The guy's such a Dick. I can't believe it."" I know. It's horrible."" Did he manage to tell you the company before? Hard to believe two in a row like that? I mean, what an unlucky guy. Did you know that he was smarter than his principal in elementary school? He's been smarter than every CEO. So, by the way, the next asshole manager you can see in the mirror in the morning..."

Speaker 2: "is going to be you."

Speaker 3: But it's not my team. I'm just giving you feedback. So, if you do that, you'll start to see those things more that become intuitive after a while. In the traditional outsourced head hunting model, there's a one- to- one ratio between the recruiter and the manager, and you're in it together. Instead of throwing it over the wall to HR to save, throw me back some resumes, and I'll throw you back who I want your shoulder to shoulder. And so, the difference, philosophically, in my approach is that, managers own building fabulous teams that create high quality work on time. That's their job. HR's job is to help them get that right. But it's not an HR's job to build their team. And if I have the hiring managers that didn't have time and couldn't return the email, I'd just take their recruiters away. I'm like," Okay. Well, you figure it out. You're on your own because we hired you to build a great team. We didn't hire you to tell my team what. My team knows what to do. So, either need them or not. And if you don't, that's cool. You got your own methodology. Rock on. Let me know if I can help you with scheduling."

Speaker 2: So you have basically business partners for all the different functional areas?

Speaker 3: Yeah. And they spent a lot of time in those functional areas. So, look, we started with a conversation about how to find the problem. And so, whoever on the recruiting team that was working on that teams openings, would be in meetings with them, would go to most of their larger team meetings because I had to learn to speak the language and find out what kind of team they were building.

Speaker 2: This is definitely the hardest part.

Speaker 3: Sorry on that one. We're doing streaming and we've gotten in all the DVD players, but the next big penetration in the household is game players because they're already in the living room, they already stream video.

Speaker 2: This is like getting Netflix on the players.

Speaker 3: Right. And we're on the PlayStation because we had good relationship with Microsoft. Reed was on the board. And so, there wasn't that much. What we wanted was the Wii. It's cheap. Everybody's got one and it's easy, especially younger people. And then...

Speaker 3: Cheap. Everybody's got one, especially younger people. And then we also knew that if you could hook them when they're six, you got them forever, because why would you ever do anything else when you get to do that? But it's really hard because the development cycle for the Wii is two and a half years, so they don't put new players out very often. And we'd missed one, so we're like," Oh well, if we ever get..." So then we're in the Wii," Oh, hell yeah." Well, when? The next 10 months... 10 months. Shit. Do we have anybody that knows anything about it? That would be zero. Right? Other than have one in my living room, taken it apart, which meanwhile, people are doing furiously. So I'd take one of my recruiters and I'm like," Okay, this is it. This is your only job. We've got to build this team in the next six weeks probably. We've got to build the software, we've got to test the software inaudible technology." So fast forward, and we're celebrating the launch of Netflix on the Wii and everybody's at the courtyard and we're having a big party celebration. I'm standing next to this person, Bethany, and she's kind of weepy and I said," Are you all right? Did something happened today?" She's goes," I built that team. Look at the shit that we did today."

Dave Gerhardt: She was so proud.

Speaker 3: She was so proud. And meanwhile they're like," And thank you, Bethany for bringing us together to be able to do this incredible thing." And I tell that story to HR people. I'm like," That's how you want them to feel." Right?

Dave Gerhardt: Yeah. I'm thinking about Keith, right now.

Speaker 3: Yeah. And imagine the motivation is really powerful, it's really powerful.

Dave Gerhardt: And when you think about it like that, when you think about your responsibilities to build a team, you think about the puzzle pieces. You're not going to get all the same personality type. This is a strength. This is a weakness. You need to think about-

Speaker 3: Start with what you want to do differently. My methodology is think six months out. Think your team is amazing. People are just awed by what you're accomplishing. What's occurring then that's not occurring now? And then do all the numerals that are associated with that. Write that down, but make a movie of it. Are there more meetings? Are there less meetings? Are you arguing passionately coming up with a decision and executing or are you just arguing all the time, wasting time? What's different. Right? And then you drop down and you go," Okay, in order to do that, marketing." I need people who get up and go, realize that the technical people don't understand our new campaign and they don't sit around and go," These engineers, they just don't understand marketing." They get off their butts and they walk over to somebody in engineering and go," Can I talk to you about the campaign because it would really help me to know your perspective on it, because I want to make sure that we're selling what you're building." Crazy stuff. Okay. So now you drop down and you say," Okay, what would people need to know how to do in order to accomplish that?" And if you've got a team full of introverts that don't like engineers, you probably should have some people that do. Then you drop down and you say," Okay, what kind of skills and experience would it take for somebody to know how to do that in order to accomplish that? And then, and only then, who do you got?" And what we typically do is we start with who we've got and where we want to go and go hire some people to do it. Instead of that'll give you the puzzle. You know what? We really could use somebody who's seen... Scale is one that's usually hard to get in your startup team. But then you're like," I need somebody who's seen bigger." And then you just go hire somebody from a big company and they fail.

Speaker 4: How often do you go and evaluate what you have, look at the mix of the team?

Speaker 3: Every quarter. You should go six months out quarterly. Moves that fast now. I mean, I think six months out is the most realistic time horizon and if you don't put a time horizon on it, you'll never do it. You have to put time on it. So the most common startup problem is they don't put a wrapper on it, time wrapper. When's that going to happen, that culture? Someday.

Speaker 4: He's burned this one into my head. Dates are forcing functions. You want something done-

Speaker 3: So the day after, I stood on a chair, this is when I advise startups, I'm like," Are you past the stand on a chair part?" When you can stand on a chair and yell. Once you can't do that anymore, you have to change the way you communicate. But I stood on a chair and I said," We are not your family."

Speaker 4: I want to go deep on that for a second. That's something that we've been talking about a lot lately, because I think it's easy to say," Oh, this is your family. These are the people you spend so much time with. This is one big family here." Why is that such a bad way of thinking?

Speaker 3: Because it's not true. Families are undying love.

Speaker 4: Yeah. You can't get rid of them.

Speaker 3: You can't get rid of them and you're going to lend your brother- in- law money even though he's a deadbeat, because he's your sister's husband and that's what families do. You're going to forgive my daughter who doesn't call me anymore because she's busy with her life. She's got other stuff to do. And you don't come together for life and to do whatever comes along. You're a team that comes together to create a product or service that you provide to people that they give you money for.

Speaker 4: The other thing that's missing that I see all the time, and this is my rants because I go on tirades all the time, is that-

Speaker 3: Good for you. I love the tirades.

Speaker 4: Yeah. I love the tirades. Is that people want that on the other side, but they also want to work 11:00 AM to 03: 00 PM and have all those things.

Dave Gerhardt: inaudible.

Speaker 3: Yeah. I really pay attention to this. This is my life. Okay? When you go home at the end of a workday and say to whoever it is that's there, your pet, your spouse, your plants," God damn, it was a great day at work today." It is never comma there were macadamia nuts in the cookies.

Dave Gerhardt: Never.

Speaker 3: It is always," We did it." And when I talked to HR people, I just did a group of HR people, and I said," So tell me what you do?"" Well, you know I'm an HR." I'm like," I know that. What do you do? What do you do that drives this business forward?"" What are you talking about?"" What business metric does the work that you do every day address?"" I make people happy." I'm like," That's not a job." And I said," Okay, so here's your homework. Let's say, I thought that was a reason for being, I don't, but let's say I did. And my theory is that fabulous work with other smart people that affects millions of people is what drives people. So you know five very successful people in this company. In the next five days, I want you to talk to each one of them and say," Tell me about a time that you accomplished something that you're extraordinarily proud of." And I said," It will always be hard."

Dave Gerhardt: Yeah. Always be hard.

Speaker 3: Always be hard. It'll never be like,"Oh my God, it was total piece of cake. We came to work at 10: 00 AM we left at 03:00 PM and mostly we just partied. And there were cocktails, a lot."

Dave Gerhardt: It was hard.

Speaker 3: It was hard. Right? You didn't think you could do it or there's a person on my team that I really didn't think that much of and she stepped up and it was awesome. We couldn't have done it. It's always those stories. So that's what makes people happy at work, accomplishing stuff. I think that the way you go farther in your career is you have a track record of," I know that's true. You know that's true." It's not that you have progressive job titles. It's that you could describe what you accomplished. When you interview people and you think," Oh, this person's really great." It's when their eyes light up and they can tell you exactly what they did.

Dave Gerhardt: Yes. That's it. He's laughing because that's the thing that I talked about. The eyes light up. And people are looking at me, like," What are you talking about? I don't understand."

Speaker 3: When you touch their passion button, you can't fake it. Yeah. You can't fake it. And that's my algorithm for success. I'm giving you my whole book here. crosstalk. Is what you love to do that you're extraordinarily good at doing, something we need someone to be great at.

Dave Gerhardt: Yep.

Speaker 3: Okay?

Speaker 4: Those are the three.

Speaker 3: And when you're driving to work or you're on the subway and you're not looking forward to it, then take my algorithm and tear it apart." They don't even realize how good I am at this stuff and I could be doing this." It's like," I know how to do this great thing and it doesn't even matter." And the answer might be," It doesn't."

Speaker 4: So, not a good fit.

Speaker 3: Not a good fit. Or what if I hired you to do something and you amazingly did it and now you're done? Builders are rarely the best maintainers. So you've spent the last three years creating some incredible product that everybody loves and you're done doing it, but now you have tenure and you care about retention. So what are you going to do to develop me to do something I like to do next? Here's what I like to do. And you don't need anybody to do that. And honestly, you asked me about goodbyes, we don't say," Man, we wouldn't be here today without you."

Speaker 4: Yeah.

Speaker 3: "That was amazing." And when I look out six months and see what we have to do and the team I need to build, if you came in and interviewed, I wouldn't hire you.

Speaker 4: Yeah. Not now.

Speaker 3: So how do we figure how to leverage this for the next place that really needs somebody like you?

Speaker 4: I love that. I was going to ask you, how do you do this with people and just be real with them and not have people say," Oh, they have an edge?"

Speaker 3: You have to be real with them all the time. And you have to do it with love and respect.

Dave Gerhardt: What advice would you give to us? We've grown from 10 to 50 people probably in the last year or so. Next stage is going to be 50 to 500, which is what you've mentioned before. Looking at us as about to be 50 people, what advice would you leave us with?

Speaker 3: Watch for the danger of nostalgia?

Dave Gerhardt: Ooh. People missing the old days.

Speaker 3: Yeah. That's your first sign of smoke.

Dave Gerhardt: That's really good. I'm thinking of examples.

Speaker 3: And right at 50 people is when you start to get these aches and pains. And so when that happens, it's a signal that you have to prepare the organization for change.

DC: I forget where I heard it, I heard this quote once, which was in a movie, it was a great movie quote, but this is the thought that I have in my head when I'm in meetings. I have a sense of urgency and it's," Don't waste my bleeping time. Let's go."

Dave Gerhardt: You can stay, but we have the explicit tag on this. crosstalk.

DC: "My mother bleeping time and let's keep this focused." And I think one thing that I didn't mention it in the last point, which is keep the meeting as small as possible, is people are worried and they invite a lot of people because they want to be transparent about what's going on in the meeting. Instead of inviting people, what we encourage is, share what you decided on in that meeting with the entire company, have full transparency. That doesn't mean that the people have to literally be in the room with you. But as soon as you leave that meeting, share with everyone that you can, everyone on your team, everyone affected, whatever was decided in that meeting.

Speaker 4: Yeah, it's like one of the things that we do at Drift for example, is even if somebody wasn't in that meeting, it's almost like unless somebody took the action items out of that meeting and wrote them up on our Wiki and then shared them in Slack, it's almost as if that meeting didn't happen.

DC: Exactly.

Speaker 4: So, you're doing both, right? You're not inviting people, but you're still sharing everything that happened.

DC: And we'll do different things. We'll share written notes of a meeting. We'll share sometimes audio notes, sometimes video if we have someone come in and we video that, those notes, and a lot of times we just share photos of whiteboards of where decisions were made and we share those internally.

Speaker 4: Or even like, you will take the deck that you present to our Board. The whole company isn't at that meeting. They'll say," Hey, here's a link to the Board meeting. It went well. Here's what we covered."

DC: Exactly. And so if anyone has questions, we can talk about that, but they don't have to be in the meeting. We don't need to waste their time.

Speaker 4: And then the last guard rail is, either participate or excuse yourself.

DC: Yeah. I've seen some people pull this off really well, but it's very rare, which is if you are in those very few meetings that are very focused and have a small number of people, even then, if you feel like you're not adding value to this meeting, I think Elise has done this well on our team sometimes, in an Elise kind of way, of just get up and be like," I'm leaving this meeting because I'm not adding value to this thing." But I've seen other people do that very well.

Speaker 4: But people can be offended by that.

DC: No," I'm going to excuse myself. I don't think I'm adding value to this meeting. Thanks for inviting me. I'm going to go off and do what I need to do." I think Dave has done it several times as well.

Dave Gerhardt: Yeah. It depends. If I'm in a meeting and we start talking about engineering and we go too deep, I'm out.

DC: Yeah." What'd you do this week?"

Dave Gerhardt: I'm out. I'm out. I'm out. See ya. Ask me when I'm filling up my coffee or something.

DC: Exactly. Not now.

Dave Gerhardt: All right. So I've got to ask you then, how to run a company without meetings. It sounds basically like a core value of this podcast. Get up out of your chair, go over and talk to somebody.

DC: It's very simple. Get up, communicate. Communicate with that person or those people. Now in the age of Drift and Slack and messages and phone and all those kind of different ways that we can communicate, even less reason to have face- to- face meetings or even virtual meetings. Have as many as possible, just over communicate and default to transparency in everything that you do and you'll have less reasons to have a meeting.

Dave Gerhardt: I love it. Okay. So yeah. Yeah. We're good. I just set up. We're good now, it's recording.

DC: Okay.

Dave Gerhardt: The blinking red just means a it's monitoring.

DC: Okay. Okay.

Dave Gerhardt: All right. So topic for today is about hiring. The hottest job that everybody wants, everybody wants to work at a startup that's number one. So we got that out of the way.

DC: Covered.

Dave Gerhardt: Second part of that, so first they want to get a job at a startup but then the thing that everybody wants to do at a startup is all of a sudden, everybody wants to be a product manager.

DC: Amen. I found that out recently when I gave a talk at HBS. So back in the day when my product managers that I used to work with, wanted to leave product management and they would go to HBS. Now I'm going to HBS and people want to leave HBS and become a product manager.

Dave Gerhardt: So people go to business school and then they come out being product managers.

DC: Yes.

Dave Gerhardt: We don't need to dive into it, we've touched on MBA stuff before, so we won't go deep in that one, even though I can see it on your face. But the question that everybody asks you a lot is," How do you hire PMs? What do you look for in hiring PMs?" And you have a really," I don't really care," take on this.

DC: I care deeply.

Dave Gerhardt: You care deeply, but you have a criteria that's the opposite of what people are going to think.

DC: Yeah. I think I have a different perspective and mine is, they usually ask me," What qualities do you need to be a PM? How much does experience play in? How technical do you have to be?" And I say," Number one, I never hire someone to be a PM who's been a PM before." And then their mouth drops.

Dave Gerhardt: Okay, so let's go in on that. That seems counterintuitive because I listen to everybody and what does everybody say about startups? The hardest thing is the people and hiring. You've got to get those things right.

DC: I agree.

Dave Gerhardt: But you're saying don't hire somebody who has experience for what you want.

DC: Yeah. And it's for a couple of reasons. One, PM is a role that is very specific to a company and if you meet PM's from five different companies, you've met five different roles that almost have very little overlap. And then the second is, the companies that I've started or I have been a part of have been product driven companies. Therefore product is our special sauce. And depending on your company and depending on what your special sauce is, for my companies it's been product. And if that's our special sauce, then we can grow people better internally than we can hire external PMs.

Dave Gerhardt: A good example, at Drift, Matt is our Product Manager and you guys hired him right out of college, he's our only product manager right now.

DC: That's right.

Dave Gerhardt: So you'd rather do that? Where you can have somebody and mold them, than take somebody who's been at Google for 10 years and then have to retrain them to this way?

DC: Exactly. Because when we mold them and they rise internally, they have our DNA.

Dave Gerhardt: Is there a skill set for product managers or can you take anybody in and have them become a product manager?

DC: I would say there are not specific skillsets, not specific rules for hiring a product manager. I think there's sharistics, there's things that we look for that we think are patterns. I think people who are naturally obviously curious about the types of products that we're building, people who are really product junkies who really geek out on whether it's product talent or new products that are being released. They're the ones that are testing new gadgets and new things all the time.

Dave Gerhardt: So you still want somebody who's playing around with products all the time, but maybe not somebody who's gone super deep on one and that's the only thing that they can think about.

DC: Exactly.

Dave Gerhardt: Okay. So the secret sauce thing is interesting. So if product is your secret sauce, you think that you can almost train anybody to be a product manager. That's specific to us. Let's maybe give some more general advice for other companies based on their secret sauce. What's your theory on who you hire? The first thing is," What's your secret sauce?"

DC: First it's identify your secret sauce. And so let's say it's another company and their secret sauce happens to be sales, and in that company they should probably hire product managers who have experienced. They probably should hire marketers that have experienced. They probably should hire finance and HR that bring a wealth of experience. But they probably shouldn't hire lots of experience when it comes to sales, because sales is their secret sauce.

Dave Gerhardt: And so in the product driven scenario, you're looking for on the outside, the non secret sauce thing is very specific in finance, HR, or just other roles that don't support the product.

DC: Exactly. I think for us, those roles, let's say the finance, HR, hire experience all day long. I'm going to look for people who are going to teach us something there. But in product, we're teaching people about product. In growth and marketing, I'd say that's the secret sauce area for us too and so we're doing more teaching than we are necessarily learning from someone who's just had 20 years of experience in a company.

Speaker 5: Woo, woo. That's the sound of the police.

Dave Gerhardt: I wish people could see you. You're in your travel gear.

Speaker 5: I'm all sweat suited up.

Dave Gerhardt: You're catching a 9: 00 PM flight to Dublin, so you're in the sweatsuit. So today on Seeking Wisdom, we're going to talk about how to work.

Speaker 5: Show me the money.

Dave Gerhardt: Let's go. I want you to tell the backstory. We were having a conversation at lunch the other day about how to work. And this is something that you've seen over the years. This could be almost like a little follow- up to Carry The Water, but this is one of those things that you have to learn it and it's also one of those things in your career that is so important, but nobody ever tells you that it's so important. How you actually work.

DC: And why do you know how to do it?

Speaker 5: Because this is how I started working. The first boss that I had, at the time, he drove me insane and he always wanted to review every email and highlight this. And every time I'd write something, this was before people used Google Docs, just Microsoft Word. Every email I got from this guy would be feedback and track changes.

DC: That's good. So it's feedback driven. Did he do it for forever or was-

Speaker 5: No. It was a couple months. I was young, 23, and I didn't know anything.

DC: Still young.

Speaker 5: Yeah, yeah, yeah. Of course, I'm still young, but this was the first job I ever had. And at first it was hard because you'd get this thing back and it's just bleeding red. I spent time writing this thing and it's just blood red, all comments. But once you realize that everything this guy was saying was right and it changes how you think about things. So that's kind of where this whole thing started from, but there's a bunch of different topics I want to talk about with you today.

DC: Yeah, it reminds me of this book I was reading, which I forgot the title off of course because there's so many, but it's a book by Colin Powell.

Speaker 5: Oh yeah.

DC: I think I mentioned it. There's this part in it that I thought was interesting that reminded me of your experience, where he said whenever he would bring on a direct report, I believe this is when he was Secretary Of State. If you don't know Colin Powell, he was Secretary Of State, he was the head of the Joint Chiefs, chairman of the Joint Chiefs and a Three- Star General. And so he would tell people who came to work for him directly that for the first amount of time, let's say it's a month, I forgot what the timeframe was, the first few months that he is going to be all over them. He's going to be on top of them night and day and it will be hard for them to breathe. It will be relentless. In terms of giving them feedback and kind of what you were saying, being in their shorts. But his goal and the reason he was telling them this, was that this was his form of training and getting them used to his kind of feedback and learning how he worked and how he ran a group or department or organization. And then over time that he would pull himself more and more away and then finally he would hardly be involved in what they were doing. And first, I think he said it because he wanted to make clear that when these people are suffering through this, that they knew there was an end in sight.

Speaker 5: This is going to be over.

DC: Yeah." This guy won't leave me alone." But that this was his form of training.

Dave Gerhardt: It's also smart because he set that expectation up front. Because he went out and said that you don't feel like even if he is micro- managing, you're not like," Man, this fucking guy. He won't let up."

DC: It changes that up. So it was his form of training and it was really clear feedback, relentless, and then let up. But usually what happens is either someone micromanages forever and so it never stops, they never set that expectation or they don't give you very detailed feedback and you're left guessing and assuming things and then getting negative feedback later on. And so he really compressed the feedback loop as we talk about it here and put that up upfront and then set expectations for when he was going to pull out.

Dave Gerhardt: The thing that I want to talk about and have this podcast is, there's this whole layer of work, there's this whole layer of things you have to do at work that actually have nothing to do with the stuff that you're creating. So if you're a designer, if you're a marketer, if you're an engineer, part one is doing your job and creating the things you need to create. But part two is, the way that you share your work, show your work, the way that you manage up and manage your manager and have one- on- ones and proactively communicate. There's this whole other layer of work that I don't think a lot of people tell you about earlier in your career. And oftentimes a lot of people miss that, because if you join an early stage company right out of college, you don't always have the structure and the process. And so the people that I know that have had it, have either worked for somebody who has managed them that way, or worked at a bigger company where there was more process.

DC: It was very structured and process driven.

Dave Gerhardt: And this is something that you talk about all the time." Show your work. Proactively communicate. It's something that we're really big on."

DC: Yeah. I think you nailed it right there. I think it comes down to communication. And that's the part that everyone's missing about their jobs. So they know their craft. Let's say it's design, let's say it's marketing, let's say it's engineering, whatever it is, finance, they know their craft but they've never been taught and they've never been in a process where they have to learn not only to communicate to their boss or the group or their investors or whoever they're working for. We all work for someone at the end of the day, including all of us right here. And so we have investors to answer to, and we have lots of people to answer to.

Dave Gerhardt: I have you to answer to.

DC: And I have investors to answer to. See?

Dave Gerhardt: We're good, we're good.

DC: And they have investors to answer to. So-

DC: So, and they have investors to answer to. So either keep communicating to the person that you're working with and communicating to the people around you, and those might be people in your group and then people in your company across your organization. So you're never taught to communicate across and you never communicate to other people. You kind of just assume that people know what you're doing. You assume that,"Oh, I'm doing my work and I'm getting it done. And people should just know." But people shouldn't just-

Dave Gerhardt: All right, we're going to do a little Seeking Wisdom today. We haven't talked about books in a while.

DC: Damn, bringing it back to my favorite.

Dave Gerhardt: Yeah. And so, all right we came up with this topic and we're each going to share the three books that have had the biggest impact on us. But we just spent, I don't know, we spent, it took me two minutes. It took this guy like an hour. He's going through thousands of books.

DC: No way. Gave me five minutes. This guy comes in, Dave, and gives me five minutes to pick the three books that have had the most impact on my life.

Dave Gerhardt: Yeah. I mean, it's easy for me. I've read like six books so I just picked half of them.

DC: So I had to go through thousands of books in five minutes.

Dave Gerhardt: Yeah. All right. So here's what we're going to do. We'll go back and forth and we'll talk about our three. Since you're the wiser one here. Give crosstalk.

DC: The older.

Dave Gerhardt: Yeah, what's the first one?

DC: I'm going to throw you for a loop.

Dave Gerhardt: Okay, hit me.

DC: Dave's not expecting this.

Dave Gerhardt: I'm not ready.

DC: He probably has not read this. So again, these are not, didn't have enough time to really come up with the three best books. These are the three books that I'm thinking about right now, for whatever reason, that have had an impact on me.

Dave Gerhardt: Okay.

DC: The first book that I want to talk about is called Walden.

Dave Gerhardt: Uh- oh.

DC: It's by Henry David Thoreau. And-

Dave Gerhardt: So far out of my league.

DC: Dave's eyes just rolled backwards in his head. And he's like," What is going on?" So I'm going to give you a couple of quotes. That's what I was looking up, from the book. The first is, and this is from Henry David Thoreau." Our life is frittered away by detail. Simplify, simplify."

Dave Gerhardt: Damn. What made you think of this book now, for this?

DC: This time of year. So we're coming into fall here and so basically his writings about Walden Pond made me think about this time and fall in New England is that time that is awesome and kind of a little bit of melancholy.

Dave Gerhardt: Why is simplify such an important message though?

DC: It's something that we talk about all the time, right?

Dave Gerhardt: All the time.

DC: It's the thing that we kind of repeat here all the time and we think about every single day of like simplify, simplify, simplify, and even when you think you've simplified, you probably haven't simplified enough.

Dave Gerhardt: Yeah. All right.

DC: All right. His next quote from the same book is a great one." If you have built castles in the air, your work need not be lost; this is where you should be. Now put the foundations under them."

Dave Gerhardt: Damn. Translate that.

DC: So translate that. So we talk about big dreams and big things we want to do, and so it is not wrong to think of those dreams, but now we need to think about how we build the foundations to make those dreams a reality.

Dave Gerhardt: Or it's the same reason why we set goals that when we write them down, they're crazy.

DC: Holy shit.

Dave Gerhardt: And then you double them. So they're crazy.

DC: They're crazy and then I double them.

Dave Gerhardt: But they push our team to do more.

DC: Exactly. Exactly. So then it forces us to figure out how to build the foundations underneath.

Dave Gerhardt: Wow. Okay. I'm going to look like I got coloring books compared to your list.

DC: Tell us about your Elmo book.

Dave Gerhardt: All right. So the first book, this is a very popular book, but it had a big impact on me because I was just starting to get into working at tech companies. It was-

DC: What was it?

Dave Gerhardt: Actually the Steve Jobs biography, which is-

DC: That's a good one.

Dave Gerhardt: It's a very good one.

DC: It's on my list.

Dave Gerhardt: Yeah. It's on your list. Of your three?

DC: No, no, no.

Dave Gerhardt: Oh, of your thousand. Okay.

DC: Of my thousand.

Dave Gerhardt: He just showed, you can't see because it's a podcast, but he just showed me his thousands of books on Goodreads. So yeah. Thank you.

DC: It's on my top list.

Dave Gerhardt: Yeah, no. Okay, so this one I've just happened to read it, we always talk about stages and when you're thinking about things. This one was like earlier in my career just started working in tech and stuff. And I just thought it was crazy to see the behind the scenes process of building a company. And the thing that stood out was, I was at a public company at the time, and there was just a lot of stuff about managing expectations and how he managed Wall Street, which he didn't give a shit at all about stock price. And he had a lot of the same philosophies that we've talked about a bunch on the podcast and Bill Walsh. He's like," If we take care of all the little details inside the company."

DC: They'll take care of themselves.

Dave Gerhardt: The stock price is going to take care of itself. And so, a big theme was never basing a product launch around an earnings call. It's like," We're going to deliver this when we think it's ready." So that was a good one.

DC: So, how do you think that has shaped the way that you work? Is what you read in there what you live today?

Dave Gerhardt: I don't know if it's necessarily shaped my day- to- day, but I think at the time it just unlocked like a level of, okay, there is a way that people think about this differently. And there's a reason why this company has been so successful and it ties back to the whole managing for customers, not internal goals or benchmarks. Yeah. All right. What do you got? Number two.

DC: This one is no surprise. It is one that we've touched on lightly, but you think about every day, it's called Seeking Wisdom: From Darwin to Munger. Right. So this is the book that I was so obsessed about that-

Dave Gerhardt: Inspired the name, right?

DC: Inspired the name for this podcast.

Dave Gerhardt: Cool.

DC: Right, it's a book by Peter Bevelin. If you haven't read it or have it, you must purchase it now and read it. It's a long read, it's kind of sections, different teachings in it that you read over time. It's more a book that you pick up, read a little bit, put it down and then keep picking up throughout your life.

Dave Gerhardt: Good coffee table book?

DC: Great coffee table book.

Dave Gerhardt: Okay.

DC: So this is a book to own. And Peter starts the book with a Confucius quote and the quote is" A man who has committed a mistake and doesn't correct it is committing another mistake."

Dave Gerhardt: That could be the description for this podcast.

DC: Yeah. That's the very description for this podcast and everything that we write about and think about.

Dave Gerhardt: That's awesome.

DC: And of course the book goes into, and I found the book originally because of Charlie Munger, someone that we talk about a lot on this podcast and it goes into a lot of his teachings, but also others that you can learn from. So that's a great kind of coffee table book that you need to own. And Dave doesn't have it yet, but he needs to get it. I can tell he doesn't have it.

Dave Gerhardt: He does not have it. All right. My second one, read this last year for the first time. Short one, 30 pages, Managing Oneself.

DC: Oh, Okay. That's a great one.

Dave Gerhardt: Peter Drucker.

DC: Talk about it.

Dave Gerhardt: It's a little orange book. We've talked about it on this podcast a bunch.

DC: Why do you like it?

Dave Gerhardt: This one unlocked like the biggest thing for me. So there's a bunch of different lessons. It's all about managing yourself. You can't really be effective as a manager until you know how to manage yourself.

DC: Yes.

Dave Gerhardt: But for me, there was one line which was worth I don't know, the book was$ 2. 99, so it doesn't matter. He talks about," Spend more time focusing on your strengths than worrying about trying to make up for the things that you're not great at." So, I'll use my personal example, right. For me, that could be writing, creating content, email copywriting. Right? So I used to think that there was like this trend in marketing where you need to be able to do everything in marketing. You need to be a master of analytics, a master of SEO, CRO optimization, and everything. It's harder for you to go from having no skill in an area to being mediocre than it is from focusing on what you're good at and trying to be great.

DC: Absolutely. I love that. It's such a great book. That's why it's a book that we recommend internally here at Drift. And we give to people.

Dave Gerhardt: And it even ties back to simplify, right? Out of all the things you can work on, stick to this one thing.

DC: Exactly. Simplify, simplify, simplify.

Dave Gerhardt: What do you got?

DC: I have a book here that, unlike my first two, probably won't stand the test of time because it's very current, but it's a super exciting book and it's actually a book, we had some friends come up this weekend from New York, old friends, and we were talking about something and I went into my library and I gave my copy of this book as a gift to a friend of ours. And it's a book called Bold, B- O- L- D. And it's written by Peter Diamandis, and basically the subtitle is called How to Go Big, Create Wealth, and Impact the World.

Dave Gerhardt: Why isn't it going to last?

DC: Because it's talking about current trends, right?

Dave Gerhardt: Okay.

DC: And this is a super exciting book you should pick up. Easy read. And Peter is the founder of the XPRIZE. He's a doctor, a PhD, a astrophysicist, he's an amazing person. But beyond all that, if you've never seen him speak, he has this ability to take all that really complicated stuff that we don't understand and break it down and simplify it. And he's also the creator of Singularity University where he teaches people. And so this book, Bold, really talks about these trends, and these are the kinds of trends that we think about at Drift that we're trying to build upon. We talk a lot about the trends of messaging, right?

Dave Gerhardt: Mm-hmm(affirmative).

DC: And that's something that he goes into. He talks about crowdfunding. He talks about all of the different things that are happening in AI, in manufacturing and these trends, that we need to kind of capture these trends and these are going to be the things that propel us into the future. So it's all about if you wanted to think about radical and radical ideas and moonshot kind of projects pick up this copy of Bold by Peter Diamandis, amazing speaker.

Dave Gerhardt: Also, don't be in the car right now, trying to write down all these books. I'll put them all in the show notes. All right. Last one. For me, it was a book called Ogilvy on Advertising.

DC: Oh, damn.

Dave Gerhardt: This one is on my list because you got me to go back and study all of the classics.

DC: And was it worthwhile?

Dave Gerhardt: It's all I've been reading.

DC: History.

Dave Gerhardt: Yeah. So I've just started the seventh book I've read about copywriting and marketing and those books have taught me more about marketing than anything else. And this one's the one that kicked it off. And what was so cool about reading this book was, damn, these were all lessons from like 1940, 1950. And they are so relevant to all the stuff that we're doing today.

DC: Yeah.

Dave Gerhardt: And that was the best lesson," Oh, this is books from 1950 and everything here is still relevant."

DC: What's interesting, aside from the last book that I mentioned, Bold, all of the books that that we've touched upon are books that think, talk about history. Right. And the importance of learning lessons from things that have happened in repeated in history.

Dave Gerhardt: Yeah. Damn, I had something else I was going to say, but yeah, so that's our book list. So we'll write up these six books for you. And I think we're going to do some more, we'll do some more book reviews, but here here's the call to action for this, for this show.

DC: What's that? Hit me.

Dave Gerhardt: Yeah, tweet at us at Drift and give us, doesn't have to be three, what books have had the biggest impact on you?

DC: Oh, man, I'm looking forward to seeing this. I want to put some stuff on my book list.

Dave Gerhardt: Yeah, we've been getting a lot more good stuff. People saying" Oh, I read this book. It's awesome."

DC: I want to put some stuff on my book list. I need some stuff. What are you reading right now, Dave? Put you on the spot.

Dave Gerhardt: I'm reading the copywriter's handbook.

DC: Wow. That's deep.

Dave Gerhardt: Yeah. I wasn't going to read it at first because it seemed LIKE one of those kind of encyclopedia type books, not a real book, but it's-

DC: It was good?

Dave Gerhardt: It's so good. Yeah. It's so relevant. I keep taking notes cause you know me, I make lists. What do you got?

DC: Oh, a couple, I think.

Dave Gerhardt: A couple?

DC: Here are the ones that I'm listening to.

Dave Gerhardt: I'm glad that you can remember.

DC: Yeah. So I won't go into the ones that I'm reading physically, but I'm going to go into the ones that, crosstalk

Dave Gerhardt: Wait, we've talked about this before, but why did you decide to to listen to this one versus get it and read it.

DC: Some of these because it just entertainment. And so I want to qualify them and others that are more, I like listening to some of these biographies because they're usually longer and I can listen to them in parts. And so I did read a really good book, current book, a fun book, I should say called Running Man. I finished that last week, I believe. And it's the story of a guy who goes through addiction and then comes out and basically is obsessed with running. So it's a guy who's been running through the Sahara, running ultras, which are hundred plus mile races.

Dave Gerhardt: Yeah, that's awesome.

DC: That was actually a pretty interesting book just about athletics.

Dave Gerhardt: Yep.

DC: And then what I'm reading all at once here, these are all at the same time, ss Grant Cardone's new book called Be Obsessed Or Be Average. And I know crosstalk.

Dave Gerhardt: That's your guy.

DC: That's my guy, uncle G, what's up? It's uncle DC. And a lot of you are going to hate on Grant Cardone, but I think he has a good message underneath everything and he makes me laugh, Thinking Fast and Slow by Daniel Kahneman. Wow. What a book. Read that three times.

Dave Gerhardt: We'll do one on that.

DC: We'll do a book review on that. I'm reading Titan, which is the story of John D. Rockefeller, a great book. Competing Against Luck, which is a new book by Clayton Christenson. And two more, Even This I Get To Experience, which is a biography by Norman Lear. If you don't know him, he did All in the Family and a lot of books, a lot of shows I should say, in the seventies. And last one is The Great Bridge, which is the telling of the building of the Brooklyn Bridge by David McCullough.

Dave Gerhardt: Damn, all over the map.

DC: Yeah. All over the map. And I'm reading a bunch more, which I won't get into. I'm actually reading Freud right now, which is amazing.

Dave Gerhardt: That list of books is exactly what we talked about. We did a podcast on how to come up with better ideas.

DC: Yeah.

Dave Gerhardt: That's your secret.

DC: inaudible right there.

Dave Gerhardt: That's your secret right there. Six books all across the map.

DC: Yeah. Bridges, building bridges, building oil companies selling.

Dave Gerhardt: Let's go into this mindset thing because we talk about this a lot, but we haven't done a episode where we talk a lot about mindset. And I saw you're reading you got some stoicism that you're following right now.

Speaker 6: I've read lot's of stuff, yeah

Dave Gerhardt: What is your kind of philosophy on mindset? Start there.

Speaker 6: Stress plus rest equals growth.

DC: Yep.

Speaker 6: It's a section in my book and it's really how I try to live.

Dave Gerhardt: Stress plus rest equals growth.

Speaker 6: Yes.

Dave Gerhardt: Okay.

Speaker 6: Which is, if you think about, I know we said we're not going to do physiology, we're going to do mindset, but let me just take a quick detour to physiology.

Dave Gerhardt: We can do both.

Speaker 6: You think about how you make a physiological muscle stronger, like your bicep muscle on your arm. You have to stress it, right? You have to lift the weight, that breaks the muscle down and tears it. But if you lift way too heavy of a weight, what happens? You end up getting injured, you tear your bicep tendon. If you lift like a two pound weight, you could sit there all day, nothing's going to happen. You have to find a weight that works your muscle just about to fatigue, embarrasses it, but doesn't totally crush it. That's step one. That's the sweet spot weight. Step two is if you just lift that weight all day, every day, you're going to end up literally burnt out. So what you need to do is you need to find that weight that stresses the muscle to get a stimulus, but then rest and recover in between sessions, so the muscle gets stronger. And I think that that is a pattern that holds true for everything, for how to grow cognitively, how to grow creatively, how to grow emotionally, how to grow in a relationship.

DC: I love it.

Speaker 6: Perhaps even how to grow a company.

Dave Gerhardt: Why? What do you love?

DC: I love it because, because something that we were talking about before we started to record was that the fascinating thing to me is that all these patterns are the same. Right? And one of the things that we talk about at Drift, which is our company, is that our values, just us as the founding team, is this work hard, play hard, right? It's not about this false sense of balance, but it's when we're here, we're going to work hard, we're going to go for it. But equally we need to rest and recover and we need to do that hard.

Speaker 6: So, back to patterns, this is something that elite athletes have nailed. And I feel like people that have more elite cerebrals have not yet nailed it.

DC: Yeah.

Speaker 6: So what happens with athletes is you keep your hard days really hard and your easy days, really easy. Stress, rest, growth. Otherwise you get stuck in this middle zone where your hard days are never that hard, because they can't be, because you didn't take your easy days easy.

DC: Yep.

Speaker 6: And that middle zone is where careers are inaudible and you stagnate. So how I like to think about it, whether we're talking about athletes or a corporate athlete or a creative, someone that works with their mind, is that too much stress without enough rest leads to injury, illness, burnout. Not enough stress, too much rest, is complacency stagnation. And I think, again, I think that you could scale this all the way up to how organizations function.

DC: I totally agree. And what do you see as the commonality now that you have clients that are both athletes, elite athletes and entrepreneurs, CEOs? Is there a hundred percent overlap? Is there just common patterns that you see?

Speaker 6: I think the most common pattern is intrinsically motivated, driven people, it's not about stressing more. It's about holding them back and making sure that they respect the rest.

DC: So the rest part, right?

Speaker 6: Yeah.

DC: They have the stress. They're good at the stress. The people that are coming to you?

Speaker 6: Right. In helping them reframe rest as not being something that is separate from the work, but a part of the work.

Dave Gerhardt: This is like-

Speaker 6: I think that's a subtle shift because if you think of rest," I'm going to step away from work to go on a day hike in Yosemite." Or," I'm just tired. So I'm going to sleep 10 hours tonight, even though I was supposed to do work." That is like you're sacrificing work to rest. But if you shift your mindset and think of it in the stress plus rest equals growth, it's all a part of the same cycle and the same thing. So then that day hike in Yosemite isn't a luxury of missing work. Odds are, I'm going to have 10 creative thoughts on that hike that are going to be the best thing for my work and I'm going to feel better. And if I feel better, I'll do better work.

DC: And you know what a key part in there, for me, is that by flipping it, you're removing the guilt. Right. You're removing this guilt factor that someone might have of,"Oh, I'm skipping work to go to Yosemite" Which guilt leads to more stress. So they're piling on the stress.

Speaker 6: Totally. And I would just ask both of you, and then I guess listeners, I know myself, I have had all of my best ideas, not while I've been actively working on the thing. My best ideas come to me when I'm on vacation, when I'm out for a run, when I'm just chilling out. And it's not like I'm actively trying to problem solve. When I go on a run, I just let my mind go. But I solve problems that I, literally for three weeks, had been thinking about and could not solve. So I am so convinced of the value of stepping away in rest that, to me, not resting is sacrifice good work.

DC: Totally. And you know, the way I interpret that is that both were equally important, right? The stress was important because it was kind of what got your brain thinking about this and it got you thinking about this, but then the recovery gave you the space away from it to actually process something that you had been going through, right? It's not like if you only had rest and no active stress that you could be coming up with these ideas.

Speaker 6: It's interesting that you go there. So in the creativity research, the prevailing theory of how creativity works is exactly what you just said. So it's three stages. You have immersion, which is you're actively problem solving, thinking about what you're working on at the whiteboard. You have incubation, which is now you've primed your brain so you kind of let it sit. And then you have insight, which is that" Aha" moment. And in a very micro level, this is why people tend to have breakthrough thoughts in the shower, because you've been working on something all day. Your subconscious mind turns on," Aha."

DC: It wasn't the shower it was crosstalk.

Speaker 6: No. crosstalk

Dave Gerhardt: We talk about this a lot. And one of the favorite, David Ogilvy is this old school copywriter, one of the best creative guys ever, and he has this thing where he's like the secret to good ideas is you feed your brain with all that information, right? And then you unhook your subconsciousness. So that could be you're reading a ton of books, listening to podcasts, writing a lot. You're not actively thinking about that problem. You're just constantly doing work. And then when you're playing golf on a Saturday morning, riding your mountain bike, working out, going for a run. That's when that idea hits you because you've unhooked that subconsciousness. But the stress part is feeding that brain, and that's why we talk about learning so much and just consuming, the best people that we work with and the smartest people are the ones who are always learning and always consuming information.

Speaker 6: Totally.

Dave Gerhardt: Because that's when you unhook this ability to create ideas. I know for me, personally, I never read books. I never cared about any of that stuff, but in the last couple of years, I really doubled down on learning. He pushed me to read a lot and learn a lot. And now, it's never been easier for me. I feel like I have more good ideas now than I ever had, and that's a competitive advantage. And what I notice is it's because I'm reading all the time and learning all the time that when we're in the Uber on the way over here, I'm like," oh yeah. What if we did this thing?" And that's a direct product of that, right?

Speaker 6: Yeah, totally. You're priming your brain. And then when you step away, it just does its thing.

DC: Does its thing.

Dave Gerhardt: All right, so how to come up with better ideas. Wanted to do this episode because you and I were trading a couple of messages the other day. And I said to you," There is a direct relationship between how much I'm reading and listening to podcasts and articles and books and how much I'm able to create things."

DC: Yeah, and the quality of your ideas.

Dave Gerhardt: The quality of the ideas. If you look at anything I've written or anything I've done, I was reading something, I was deep in a book, deep in something that's related to that. And you said," Boom, congratulations. You earned a point. You unlocked the secret."

DC: Man, Dave just unlocked a level. Right. And I had to point that out to him. So he just took it up a notch. And it's something that is, man, it takes a while to figure this out and Dave figured it out quick.

Dave Gerhardt: I wish I knew earlier, but like we always say, there's stages. I'm glad I found out now.

DC: You weren't ready.

Dave Gerhardt: I wasn't ready.

DC: Grasshopper.

Dave Gerhardt: All right, here's this week's fan love, shout out of the week. This is from Doji Style.

DC: What, Doji Style?

Dave Gerhardt: "DC and DG are bringing immense value to the podcast world. I've been designing products for 15 years and never come across such a rich honey hole of information, not the regurgitated nonsense that you find on every email list either, real ideas that are often unique and outside the norm of the herd. I hope you guys never quit, despite the lack of ROI On this project."

DC: We got ROI. Hey.

Dave Gerhardt: I love it.

DC: I love the fan love. Thank you, Doji. Two things we need. One, leave that five star review. Actually, go check for me and see if they allow six star reviews now. But if they don't leave the five star review for the uncle, and then number two, we need help finding someone. Someone left a comment last week and shouted out Amy.

Dave Gerhardt: Yeah.

DC: And only left his or her screen name.

Dave Gerhardt: Look, email us.

DC: Email us.

Dave Gerhardt: We need to know because you won something,

DC: You won something. I need to get you the gift.

Dave Gerhardt: Don't email him, email me.

DC: Yeah, I won't answer it.

Dave Gerhardt: DG@ drift. com. I'll make sure it gets emailed. We need to give you the prize. That is rightfully yours.

DC: Yeah, and they mentioned Amy and I believe they might've been from Switzerland or Sweden.

Dave Gerhardt: I love that.

DC: Let's get it going. We're international, bro.

Dave Gerhardt: Somebody said," You quite literally can't spend 15 to 20 minutes of your week doing anything that will have a bigger impact on your business." We must have poked at someone with this ROI thing. Because this person also said" This podcast ROI has been exponential for me."

DC: That's awesome.

Dave Gerhardt: They love it.

DC: All right. Keep learning. Keep growing.


If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. ----- For the 100th episode of Seeking Wisdom, we thought it would be fun to pull together some hits -- roughly 10 clips, 10 minutes each, for 100 minutes of the most popular episodes of Seeking Wisdom. Here's the full rundown: 0:48-5:37 - How SW came to be from EP #86 Live at WeWork 5:39-13:43 - Highlights from #2 Learning Machine 13:46 - 22:44 - Highlights from #93 w/Pat Grady on First Principles and Advice for Startups 22:47-45:34 #19 on Carrying the Water 45:35- 1:01:43 - #90 w/ Patty McCord 1:01:44 - 1:05:07 - #51 How To Run A Meeting 1:05:09-1:10:20 - #6 On Hiring Product Managers 1:10:21 - 1:16:57 - #36 How To Work 1:16:58 - 1:30:55 - Books That Have Had The Biggest Impact 1:30:57-1:38:26 - #95 With Brad Stulberg 1:38:28 - 1:39:18 - #28 How to Come Up With Better Ideas 1:39:21 - 1:40:54 - 6 Stars Only! The only question now is: what will be on Greatest Hits, Vol. 2?