David Carpe - How to Network, and The Myth of The Great Silent Resignation

0:00 Jon McLachlan

Welcome everyone to another episode of the Security Podcast in Silicon Valley. I am your host, Jon McLachlan, and I'm here today with a very special guest, David Carpe, the founder of Carpe Search Partners. Welcome to the show, David.

0:14 David Carpe

Hi, thanks for having me.

0:16 Jon McLachlan

Would you like to share with our listeners your background?

0:20 David Carpe

Sure. I will give you the short version. I was BFA, stone sculpture, studio art. I spent some time in Fidelity and equity research and then in trading and ops, and then went off to grad school, did an MBA in finance, did a startup that blew up in the dot-com boom. Ran a corporate espionage firm for seven. That was fun. And in that period of time, spent a lot of time with Microsoft. I worked in the old office of the CTO and then the CSA when Ray was there. So it was 12 years there. Took over a search firm and then landed through people I knew at SignalFire. So I just recently left a venture fund, like wonderful tier one fund called SignalFire. And I spent, I don't know, five and a half years there. Had some crazy personal stuff happen. So I left this past winter on great terms. So I'm doing [work with the] portfolio and with other startups. So I spend, for the last 10 years, 15 years, 10 to 14, has been just intensely focused on early stage startup activity, separate from some large clients like Microsoft, TiVo, PGP. Really, my focus is early stage, incubation, studio, pre-seed, [and] sometimes growth stage in our portfolio. That's fun. It's just product and engineering. That's all I do. The build. I just focus on co-founders, first builders, first heads of product, but really helping founders build companies.

1:39 Jon McLachlan

No, that's amazing. We have plenty of startups in the security world here. Yeah. And sometimes these two worlds don't overlap very often. So I'm very excited to have you on our show. And as you think through your professional journey, what do you think the best day has ever been for you? The best day?

1:59 David Carpe

What literally popped into my mind was in my early 20s, I had this job at Fidelity Capital Markets working on the trading floor. And so I spent a lot of time in equity, sometime in fixed income, and hired this guy. This is like the 90s. Okay. So for some of your listeners, this is like right after the dinosaurs came and went, then the [earth came]. Then it was like early 90s. So up here, and the financial services industry was very, you know, it's a very button-down industry. And in Boston, I had this, they hired this guy, the worst operational executive I've ever seen. Like he made people cry. Like he was that kind of command control, screaming at people, threatening people, like non-stop, rattling cages all day, real like tough guy. Yeah. So I couldn't stand him. And I had been looking for a way out, looking for a way out. I wound up getting a job inside Fidelity Cap, like the venture side. And the day I was able to announce my internal move and just like say goodbye to this man, just say goodbye to this horribly toxic, destructive, just like the worst man in the world. I was just like over the, it was like this weight lifted [...].

3:09 Jon McLachlan

Wow. So, your best days, when you actually got away from this toxic person.

3:13 David Carpe

Got away from a horrible boss. I took my earliest memory. It's really my earliest memory. That's a horrible boss. Everyone's probably had one in their life. This was my one. I had [jobs in] high school, never had anybody like this. This particular man was a deeply flawed individual. And I endured it for about a year. Then I just made my break. And I was like, woohoo! There was so awesome. Freedom.

3:37 Jon McLachlan

Freedom. Okay. So how about the worst day in your entire professional journey?

3:43 David Carpe

That probably one of the worst was shutting down my startup for the dot-com boom, raising a lot of money from some big, some notable tier. It was a big [YPO] fund, so it was like the [Young Presidents' Organization], YPO. It was just like a bunch of, playing a founder of [...], the guy who built Wembley Stadium, these super people. So I raised all this money, high hopes, [dot-com boom]. Everything was crazy, high fives all around. Everyone's read about it, or they've read it through. In 2001, I'm out trying to raise again, and you literally couldn't meet with anybody. Your description of your business included an acronym, and because it was B2B, B2C, ASP, blah, blah, blah. So, after enduring the endless rejections, you accept the reality that you have to shut down your startup, lay people off. The worst day was really having to break that news to my team and then simultaneously to investors who are saying things like, how are you going to make us whole? How are you going to get us our money back? And I'm like, I can sell. So, what I did was I sold all the office furniture. I gave them like $7,000. I thought that was pretty awesome. And a couple of laptops or whatever computer crap we had. And that was a bummer. That was when I was 29. And so, no, I was 31. I don't know where I was, somewhere around like the early 30s or something, but it was just anticlimactic.

5:03 Jon McLachlan

It sounds like you were between a rock and a hard place.

5:06 David Carpe

I had two little kids. I just had another baby two years before. My wife was in. I was the only source of income. Oh, yeah. We had just graduated from being so broke. Like we were still rolling coins. Like it was crazy. Expensive to have a child. So that was this comeuppance where you also have value on paper. That's like a fantasy, right? And this is what people are living through right now, today, this year, last year, these startups imploding, kind of, I don't know, it's, it felt, there was a little bit of a [mania] in 2020. A volume of crazy. And so as it dissipates and you see what's sustainable and real, it's not a lot. A lot of companies were really never, it wasn't just they weren't built to last, they just should have never been built. They should have never, it should have never even happened.

5:55 Jon McLachlan

Sure. [Time is everything], right? When it comes to a lot of this sort of thing. And speaking [fast forward] to modern time, I've heard a lot about this quiet quitting movement, the existential crisis, almost the people are revisiting their values and asking themselves things like, oh, [is that] really like what I want to be doing for the rest of my life? It's life fulfilling? Or, and I've heard that people are up and moving after reevaluating themselves and in these positions now. What's your take on all of that?

6:28 David Carpe

Yeah, I think it's, I think a lot about it because I talk to a lot of people about it because it's a pretty polarizing issue. I am [the camp], I am in the camp that believes most of the quiet quitting stuff you're reading is, by and large, is a lot of bullshit. It's a lot of corporate control narrative designed in a, like this last [bastion] of hope for capitalism. I don't know what it is. We have to keep these large populations of people under manageable control, keep them focused on a goal in which they're productive units of labor and participants in this kind of willful participants in this system we've created, and which is capitalism writ large. We took Calvinism and we went decadence. So now you get these young people who are basically saying, all right, the things that I see frustrating young people are the same things that have bothered them for, I don't know, the last 500 to 5,000 years, right? I don't know about 5,000, but I picture somebody who is 26 years old in the 70s being just as disenfranchised, the same kind of zeitgeist, right? These attitudes, these feelings of antipathy towards capitalism and structure and power controls. So these tropes get [...], right? Nobody wants to work. Young people don't want to work. And that's where it always goes. There are two ways to look at it. One way is, what are we doing wrong? How are we failing people with this promise of work and career and all this stuff? The other is to just ignore all of that common sense issue addressment and just focus on how everyone sucks. Everyone's quiet. They're like, nobody wants to work. Nobody. I think what's happening, and this is anecdotal, that's what, my son is in his late 20s. And he, like much of his generation, okay, so I take this with a grain of salt. Look, I'm looking at this through a lens of what I would call privilege, not privilege by money, but I [privilege] by education and opportunity. So a lot of people in tech, and your listeners know this, on average, wonderful personalities, but on average, the education level and income level in the tech industry is significantly higher than the US average. So, first, he's [in] enterprise software. The people he knows, they did the right things, right? They went to college, they got good grades, they got these jobs. Now they got a [...]. Some of them have no debt and some of them have minimal debt. They're doing it right. And they're all sitting there looking forward in their 20s saying, what I get from them is that nobody knows what comes next. And this is not uncommon for young people to be like, what comes, like, who, not who am I in this world, like these existential purpose questions, just literally what comes next? I, my son, we live in Boston, right? So my son lives downtown with these other young people, all of them hang out. They look at the Boston market and they say, how does this work? We think we have good salaries, but a one-bedroom condo in the North End is like 1.2 million. So, how am I going to get that? And then simultaneously save the now estimated $3 million I need after tax retirement? These are the new sort of Gen Z projections. So, where are you going to get that four to five million net liquid, like after tax money? Right. Enough in life to live the life that you imagine you were going to live, like a home in your 30s or whatever. And so, I think that is just seeing things as they are. That is reality. Things are exorbitantly expensive. Homeownership is consistently moving out of reach further and further. And the cost of growing old is hitting inescapable highs, not to mention compounded with Medicare and Social Security. So for young people, I don't think it's quitting. I think what they're doing is they're just looking at what's happening the way young people always looked at what's happening and said, hey, I'm worried about the future. There are chinks in the armor of this American dream, right? That is the story now. It's evolved, the story is a little more serious. It's like the sequel where now we know a lot more about Darth Vader's identity. We understand the familial relations, but he's still an evil dude. There's still bad shit happening, it's just now worse, it's bigger, it's easier to see. The Death Star is almost finished, right? This thing is like, is so big, this machine we built, this version of capitalism, that we're having problems, obviously, with scalability. And like, we could see it all over the world, not just here. So, for young people, again, quiet quitting to me is just young people being like, you know what, dudes? You want me to grind? You want me to give you 100 hours a week for what? The contract that society made with me is broken. Not just the company that hired me, the contract, [writ large]. The social contract. Yeah, it's all screwed up because I'm kicking the ass, I'm busting my ass at this startup. I'm doing 100-hour weeks. I don't know if I'm going to get the money to exercise my options, but if I do, and it's worth a lot, is it going to be enough to even buy like a one-bedroom in Boston? Because I wanted to get married and have a baby, or I wanted a dog or whatever. I needed an extra room for the home office, so now I need a two bedroom, and those are 1.6 million. And so I think they're just being realistic. The negative attitude, though, is what I think people are focusing in on when people say [...].

11:26 Jon McLachlan

You're making the case that it's not a new thing.

11:27 David Carpe

[It's not] new at all.

11:30 Jon McLachlan

Yeah, these mechanics, [no big thing] going on. You make reference to the 70s.

11:36 David Carpe

Oh, so it's social media, right? Like we just put a label on it. And so it's been around, like people have, I think young people have always wondered what comes, what they become. These things are not like new paradigms for growing up and living. It's more like we have this incredible hype cycle in the news, especially in this country more so than elsewhere, where as soon as we see something, we put a label on it, we call it something, and then we [...] people and we make it an issue. We live to polarize. So, if we can take these law of small numbers and break up the camps, quiet quitting is a good polarizing. Do you or do you not fundamentally believe we're offering young people a sort of the upside that they imagined they would get? And companies, instead of even talking about the issue, this is what I'm saying. Instead of even talking about that, what they're saying is, listen, you bunch of lazy shits, get back to work. We stop quitting, quiet quitting. Nobody wants to work. No, they don't. They just don't want to stay till 7 p.m. and kill themselves because they realize now there aren't as many prizes, maybe, at the end. They're not sure what it is they're working for. But the difference now is, at least in the 90s, okay, you could have that quiet quitting attitude. You could be down on whatever. [But] if you wanted to, it was okay. You could quit. You could get a job at Coffee Connection in Boston, which would be like an early predecessor to Starbucks. And you could live with your friends and you could pay rent, and you could pay rent, and you could pay for your car, and you could afford the bus, and you maybe owned a bicycle, and you did things with your friends on the weekends because you could afford to go out to a bar at a restaurant. All of gone. All of that's gone. The cost of living is so high that you just work from your studio that you might share with one other person. So you try to keep quiet and then you finish your work day and then you wait until the next day arrives, and I think that's young people are in that.

13:23 Jon McLachlan

It's almost like a [spinning], like monotonous cage, keeping

13:27 David Carpe

Yeah, no, young people, you know what they should be, they should, like, I feel like there's a time where, if you're in your 20s, I'm just talking to the sort of people like two to five years out of college, not the really recent college grads. I know they could change their mind about anything, but you're in, you think you know what you want to do? You got a job as like an IC2 on a team as an engine on a cool security product. Right. I think the questions people ask about like career and other, I think what I encourage people I know to do, like in my own family, young people, when I do like career coaching and that kind of thing, that I take very seriously, is to first zoom back out, to stop thinking about your career and start to think about just the way you want to live your life because this is really what these people are asking themselves with quiet quitting. [Is work] what I do to live, or is work and career the focus and the fabric of my identity? Is it who I am? Is it what defines me? And so I think that's a really basic question people make in their 20s or 30s, at any age. People enter or re-enter these intense periods of work and career. I just think when you couple it with the frustration about like cost of living and [...] economy, yeah, getting the things you want, life. And then at the same time, you're like, do I even want to live this life? I think that's the question young people, the quiet quitting movement, that's the question people aren't asking, is this model for living, this model for living in which you invest your life in career growth and development in return for seemingly infinite rewards that we know are not, everyone's disposable. We just saw the layoffs for three years, we're seeing them again this year. So, you're [a] disposable unit of labor. Get over it, man. As special as you think you are, this is what you are. You are either the owner or you're not the owner. If you're not the owner of that company, you're an employee, you're a unit of labor. The goal is to maximize your value, what you can produce for this entity. So, if you want to live that life, many people do, you can do incredibly well. But if you reject that notion, that model, I think there are a lot of young people who are, that's actually the question that I see them asking themselves. Literally, like my son has friends in these professional careers who are all like, you know what? Maybe we should quit our jobs, live a sprinter van and go work out of the van, see if we still like working while we're traveling. And then a couple of them are talking about taking off, [...], go live a different life. That's what I'm talking about. I feel young people get, they're so busy, they're so career-focused. Stop, man. Go look at what people did in the 60s, the 70s. They got out of college, like in The Graduate, and somebody, plastics. And the father said, this is a great career. Put on your jacket and tie. And you just graduate from college, you go to work and do that for 40 years until you die from a heart attack or suddenly retire and you're just old and burned out, you forgot what you even enjoyed doing. And so, I think that's what people are trying to avoid, but they don't call it that. Instead, somebody else hijacked the issue and called it quiet quitting and made a carnival out of the topic.

16:30 Jon McLachlan

No, I think it's, I think it's important to be intentional and deliberate with our choices, just with life in general, and to lead a life that's aligned with what are values that you have. And that's the tough question, right? You have to figure out like what are your values exactly. Why do we do the things that we do? And then once you have that figured out, it's easy to align life decision and what we're doing in terms of our career and all that with those values, right? You could be [...], but you have to think about that. It takes a sit down. And the tough part of thinking about that is to think about it, I don't say with a selfish [...], but you have to think about what's right for you. And it might be a little bit different than what's right for your peers, your friends, your family, the expectations that are put on us. They do influence us quite a bit. But I also think that, in some non-trivial sense, like value and meaning often can be derived from or comes from [...] around us, like people that we know, people in our lives.

17:32 David Carpe

Absolutely. So, I think for another great example, I think there are a lot of young people, or of any age, to be honest, who landed an organization. And just a counterpoint to everything I've done, I am equally in support of people embracing careers. That is quite literally what I've done. And granted, I am flaking out very rapidly in real time now that I'm older, like it's happening before my eyes. I'm just getting flakier. But I'll tell you, when I was younger, I was like running through brick walls to make shit happen. And I think there are a lot of young people who have that drive and ambition. Do it, man. Give yourself over to work. If you really believe that identity and those accomplishments are absolutely critical to you, then do it. You might not do it forever. That's totally fine. I know tons of people who run. This is also another issue that I see constantly with founders, specifically a lot of younger founders. They're running like a million miles an hour, doing everything, and they're making everything happen. And they turn around, they have success, right? And this is the valley. These are outsized outcomes. These are people I know. This isn't like they have money, like they have five or $10 million. These people have like fantasy money, right? And this is not a fair [...]. These are just other people with successful exits. What I see a lot is that they get to the other side of it. They have some awesome outcome. And all of a sudden, like, I don't know, they're in their 30s or early 40s. And so they did that. They already did that thing and were wildly successful. And it's almost like they aren't now, they got all this time, they got all like infinite choice. And it's now like, what do I do with myself? I've been goddamn busy and distracted. I totally forgot what I actually like to explore myself. I don't even know what I'm into. And so they fall into a predictable pattern. They believe that their calling is to build and to build startups and to build products because they're so good at it. And when I talk to them, I encourage them [...] [to stop], take a break from tech, and how's that set up for advice? So I have a lot of these conversations with people, and then people are like, why would you redirect people away from this awesome, high-paying opportunity of this industry? For these people, if they've done really well, they, as far as I'm concerned, man, just get off the playing field and room for somebody else.

19:38 Jon McLachlan

It is, I guess that's one way to see it. There's another way to see it, just like leading that intentional and deliberate life that you get a great deal of happiness for making things.

19:48 David Carpe

Absolutely.

19:50 Jon McLachlan

And you're in a wonderful position where you can engage that activity or even build something around it. Like, you're still building something at the end of the day.

19:59 David Carpe

Sorry to drop something that deeply worries me, deeply worries me, is the idea that people have hobbies and interest and then feel compelled to monetize them or somehow convert them into a source of income. That is also a broken way to live because young people right now are dealing with insurmountable cost of living, like the seemingly insurmountable rising cost. And so they're all encouraged like everyone needs a side hustle. Yeah. When do they have time to live? If all they do is photograph their food and now they got to do that nonstop because they like that, and then they go to work all day for this company and then Saturday for laundry. I'm not sure when they live. And that will just break you. Do that for long enough, and you'll, that's called burnout.

20:43 Jon McLachlan

That's burnout right there. It's funny that you mentioned this. I was listening to a podcast with Mark Cuban, and he said something along the lines of, don't do what you're passionate [about], do what you're good at. And the whole point of that comment was, if he had followed what he was passionate at, he'd still be trying to play basketball.

21:00 David Carpe

Yeah.

21:01 Jon McLachlan

That's just not what he's the best at.

21:03 David Carpe

So then I would say, then I would say to somebody like him, that's one way to see it. One way to also say what he just said is, do what you're good at. If you're not good at it, quit. Don't even try. Okay. So now I say to you, you're Jon McLachlan. In 10 years, you tell me you're done. You're done with security. You're done with podcasting. We're still talking. Some of these guys, I know, I've known some of these guys from my life with Microsoft for decades. I have followed them through their careers. We talk about what they become, what they want to do, if they should even do another [...], where do they belong? Like, we have deep discussions. And so I would say to somebody like that, like, if you are at that point and you've never tried it. You've never tried it, but you think your calling is fly fishing and making custom fly or flies, the little things you stitch or throw the water, or your calling is making furniture, or maybe you're supposed to be doing special education with children. Maybe you're supposed to be teaching math in high school, like whatever, being, buying some liturgical vestments and appearing in churches or something. I have no idea. But if that's what you think your calling is, even though you're good at it. You might have, you might be horrible. You don't know how to use a power tool. I would encourage strongly to go try it. Do not only do the things you're good at, or you'll never learn anything else. Right. Master your [craft]. But I mean, look, like, Michael Jordan, master your [craft], but he's also really good at baseball and golf. There were famous painters who were also phenomenal writers. And like, it goes on and on. I know software engineers who are phenomenal musicians, like tons of them. Maybe they should be in bands. Maybe they shouldn't be at Facebook or Meta, Meta, or whatever. Yeah.

22:41 Jon McLachlan

I think, I don't know. I'm not exactly sure what grabbed my interest into security. And I've always been fortunate enough to find like that intersection between passionate and skill set. But, you know, when I look back and I think about things like, the best way that I describe my interest in security is an irrational excitement about security. And I, maybe that's driven, I think a lot of people get sucked into security because, not sucked into security, but tend to focus on security just because it's a very easy way, if you just [glance] at what's happening in the world and notice that there's something like terribly wrong with how we handle data, with how we handle like security. These ideas of what does it even mean to be secure.

23:25 David Carpe

And you're right, as far as I see it, security is like a calling. It's, honest to God, if we're going to let software run the world, the security of that software is not just paramount. It is literally the fabric of like a whole society or something. If it doesn't, everything is a false story about the security of banks, healthcare. Everything we're trying to do this way is, if somebody's just going to [...], and they're going to say, I'm not moving. Like online, you're young. So there was a big thing when online banking came around with security. I [...] consulting a lot. Yeah, I was spending a lot of time with Microsoft. I spent a lot of time on security. And so these, now, this was like partner level of the both. So these are like legends of security that your listeners will all know. These were like the Bruce Schneiers, the [Mudge Zatkos], that, so I spent time [...] with people like [Barb Fox]. And you have to look at it for you or that big, right? What was always interesting was, I remember talking, I want to say it was [Barb Fox] in 2005 or something. So something would come up that was like [an] impossible to solve thing. This was the kind of stuff I did in the old CTO's office, like figure out who did what in the history of security, because something was coming up, like they needed a new architect, but a sort of like a DE-level architect to rethink security architecture for all of integrated collaborative environments, all of Exchange, the whole suite. These are like the super jobs. They direct the activities of hundreds of other architects and so on. So, generally speaking, let's say there are like three to seven people in the world who can do each of these jobs, right? But you talk to them at that level, what I thought was really interesting, don't misquote me. I want to say it was like, oh, it might have been [Hilarie Orman] in Boston. She was, some of your listeners might know her. She's long retired, but, and some other people she was connected with through [Purple Streak] software, I think. Anyways, my mind is, I remember like weird stuff. So, anyways, one of them made a comment to me that all the work in security was actually done, everything had already been solved. And really, what was left to solve was administration and policy. That's where all of the problems of the future were. They were actually in like consensus and agreement and standards, that the technology was actually increasingly easy to solve. I don't, I'm not a security guy, so I can't tell you that we've gone as far as we can go with crypto code optimization algorithms or something. But generally speaking, I understood what she was saying. We innovate on passwords and key fobs, like all these things, but generally speaking, we've accepted that we require this type of login for financial applications. Or if you work on Wall Street, you have to have this level of security on your messaging applications. And so we've gotten there on the admin side with a lot of stuff, but not everything. We're still fighting about these international data holds with all these big tech companies. I forgot how we got on that subject, but it's all good. Something to do with something. Yeah. No. Okay.

26:17 Jon McLachlan

So one of the things that I missed earlier in my career was networking. Yeah. But it sounds like you're a little, you're very good at networking and maybe can help our listeners, maybe even some of our younger listeners, understand like what is networking and how is that different from just socializing.

26:32 David Carpe

Absolutely. I was just talking to my wife about this because I was telling her I was doing your podcast because of context. She's a floral designer. She like literally doesn't give a shit about anything that has anything to do with the people I interact with every day. If I told you about a SignalFire portfolio company that I think is awesome, like in security, [...], it is, and/or any one of a number of companies, it's just, the eyes glaze over. It's so, it's so exciting. It's this like [shardable] clustered storage system. It's like stuff that like 11 other people are really excited about. So I was telling her, I was talking about [...], this is stuff that is a common topic, right? It's easy to understand. When you're young, how do you build a network so that you can parlay it into, let's say, conduits that connect you to opportunity in the future? And so there are a number of ways to think about it. And I think, first and foremost, people have to think about their identity in their network. Okay. So the easiest way to think of this is, you can be a giver or you can be a taker. And it's that simple. I am a giver. And what I mean by that is quite literally, not only do I network and I know a lot of people, I literally, separate from the searches I charge a bunch of money for or whatever, I do an incredible amount of search work for free. I just introduced, so I'm friendly with some really big CPOs at some big internet companies. So I made some introductions this morning. Yesterday, I introduced somebody else I know to a lot of our founders in the portfolio, like in our SignalFire portfolio. But across networks, I helped find CTOs for startups in my part-time because they're friends of mine. I've helped friends who are founders make critical founding team hires, no fees, because I know people. But what I'm really doing is I just am trying to help the people I know who I know are looking for these kinds of opportunities. So I'm doing it with real empathy toward, I'm focused on the candidate. It's an authentic, it's an authentic [give]. And then I'll go to the people I know who need help and I'll just connect to them. I have no expectations. I do not expect money, gifts, or anything. I just am trying to help these people because I'm a big believer in karma and goodwill. And it does, I'll tell you something, the way it pays back is over time. [I] come up and I need help or I need assistance or I need an answer to a question or whatever. I'm trying to literally have 12 hours. I'm trying to connect a certain kind of product executive with a certain founder I know because they have an absolutely weird question, and I know this person knows the answer. That's when I can text that person and say, can you do me a small favor? And I get a reply an hour or two. And it's just, again, helping somebody else. They're giving again, it's like giving, but it's like this [...]. And so you become a connector in your own network. You're always a connector within your own network. That's always important because the more you connect your network, the more value you provide to your network, the bigger your network grows by virtue of add-on introductions. And people remember you as not always wanting something. You know, those people who call you and they like always want something. Yes. I do remember. Yeah, I just did it.

29:33 Jon McLachlan

It's funny. I, growing up, I watched a lot of Will and Grace. One of the episodes, they were talking about like the different roles that you can play in a relationship. And the way that they had put it in the show, Will and Grace [were] having a discussion, and they broke it into two types of people. You have gardeners and you have flowers. You have givers and you have takers, you know?

29:56 David Carpe

Yeah, so, and I think that's how a lot of people see it because even if they don't call it that, they think about the people they know and they live, just like your friends in your personal life growing up. If you were in high school. And you, I didn't grow up with cell phones. That's how old I am. We like, after high school, we got on our horses. We rode down these dirt roads and we went behind like Mr. Willoughby's farm and we talked. But it was like, it literally, I had, I had to help your listeners. I had ColecoVision and I had games like surgery. And if you've read Chuck Klosterman's novels and stuff, when he talks about that generation of 80s console games, it was just hysterical. Story-based narratives, all that stuff. So, anyways, I think the other thing with networking that's important to point out to young people is, if I had like time to hit on some key things, sure. One thing that you and I were actually discussing was that there's a really common problem. And again, talking about tech. So we're talking about tech. Yeah. And what's, you're talking about a lot of above average academic performance. By and large, what I see on the engineering side and the product side of the, just the builders I know, they come through this, the whole university system is a cognitive filter. They're coming through these highly ranked or top-ranked universities, so we already know that they were competitive in high school, not necessarily competitive, but they were competitive academically. They were high-performance. So all the way through that manifestation of that identity, they get into their 20s. They were even competing for top jobs, right? So they get this top job on a security team at some hot company or some hot product. So again, they've done everything right. They've landed in the right place. They've got like this A to A plus looking resume. And now what I see them tend to do wrong is they're a couple of years out of school, or three, four, five years, it's like they're so focused on their Herculean task of, it's like some big technical accomplishment, like wowing a boss and wowing a team. That's awesome. That's awesome. If you even solve, like, what was that dude's name who invented BitTorrent? He had [...]. Oh, yeah. So you solve a really hard problem, right? Everyone's like, oh, [...]. What they, that's awesome. What they tend not to spend enough time doing is literally getting to know every single person they work with. And I do not [mean] your engineering squad or your manager. You don't have to go to conferences and events to network. You don't have to go to Zoom bars and all that crap. You can just reach out to the people at your company who work in sales, marketing, product, finance, HR, get to know other functions in your company and get to know the people involved in leadership spheres in those roles, because I'm telling you, in the next two to four years, about 80% of those people are going to change jobs at the non-executive level and below the [management] layer. So those people are going to all change jobs and now all. So in four years, when you say, you know what, I want to work on security in the entertainment industry, [your old] marketing manager, who you met before they became a director or a VP four years later, who answered some questions for you about the product package, some product literature, whatever you want to know. Now they're your contact. That's who you reach out to. Hey, remember me. And a lot of people do this correctly. A surprising number of people don't. They're so busy working. And with remote work and work from home, it's even harder to have these serendipitous hallway interactions with the marketing team or a member of the executive team, or investors visiting and you meet them. That doesn't happen anymore. So now the [rub] is that you have to make this stuff happen.

33:31 Jon McLachlan

That is what drives me crazy about these giant Zoom events where there's like a hundred people in a Zoom and there's an all-hand, and you're all listening to one person talk, and you're not interacting with each other. And it's, who are all of these people and what are they bringing to the table and who are they?

33:48 David Carpe

It's hard, it's hard. So you can never, yeah, you're not going to go to a zoominar or whatever, Zoom, 140 attendees, and then I'm going to see Jon McLachlan's little box on screen page three, upper left, three from right, second row down, and go, that dude looks really interesting. Let me click on the three dots on the box and send him [a] chat and see if, nobody's doing that. Exactly. Right. The one, I've seen some that are very well run. We did a bunch, but [...] and the network team at [SignalFire] had a whole, still do. There are a lot of people, not just funds, doing smaller events where you have a facilitator. There's, you have like maybe 20 people or 15 people. So you can directly engage everyone. So everyone gets to meet you, hear your voice, know what you do. Those events do well. People do network. They do connect.

34:35 Jon McLachlan

When you think about the roadblockers to networking, do you think like being a taker or being perceived as a taker is like a roadblocker?

34:42 David Carpe

Absolutely.

34:43 Jon McLachlan

Well, do those people, is there a place where you can do that from, or is there other roadblockers that get in the way of maybe, just to speak on behalf of maybe someone new to this? If I don't feel like I have a give, what do I do? How do I think? How do I approach that?

34:57 David Carpe

I would argue that you always have a [give]. You always have a give. There's always

35:02 Jon McLachlan

something to give.

35:02 David Carpe

Yeah. So if you're, if you're reaching out randomly, you're in, you're like IC2 on an engineering team, you're basically buried in the bowels of a product development team working on your own feature team somewhere. Who knows? Maybe I'm not even doing that yet. I'm just fixing bugs. Nobody, basically, just [assume] nobody knows you exist. The company has like a thousand people. You're like one of a, like, some handful of people buried away, and you want a network. And so, what I would say is think of something, and just think of something in your company, ideally, something that's of interest to you that you just don't really understand. An example of that might be, a really good example, if I just literally threw a [dart], if I went down where our offices were on 2nd and [Bryant] or something, and right around the corner where like Slack is, if I just threw darts at like young engineers coming out of a building or something, probably ask them, and nine out of 10 wouldn't be able to explain to me the go-to-market motion of their company they work for. Average price, average transaction times, how the business actually makes money and writes the paychecks that keep [them]. They probably have no idea how that company finds customers, generates leads. All these things are like things you should understand about, again, if you're interested in a career, and you think, for example, whether it's a big company or a startup or how you want to live your life, if you think you want to invest in your career, it doesn't matter if you're an engineer, a product manager, or whatever you do, you really need to understand how a business works. And to understand how a business works, networking is the only way to get there when you're young. Because you, unless you're a recruiter like me, that's another really good way to get really close to senior-level people very early in your career. Right? When I was in my 20s, what other CTO talked to me? I was on the phone, there was no Zoom back then. So, as far as they know, I could have been like 38, I could have been 46, but I wasn't 26. And I just, I don't know, I had a high verbal quotient, I was just a bullshitter, right? So, if you're young, right? So, if you're young and you want to get your hand [...], you always have something to give because you can reach out to marketing or you could reach out to sales and say something like, hey, I'm over here working on the product and I'm pretty sure we're building what all of our customers want. Can I talk to you about what I think I'm building? Because I'm really curious to hear how you're selling it, what you're selling, or how you

37:28 Jon McLachlan

can make sure that user experience that's going to be sold is like a nice, smooth, like your product doesn't get good.

37:34 David Carpe

You're not fudging it. It's not like you have, you, what you have to offer is like your perspective inside the company. You are a colleague, you actually work on product development. You're playing the, you're working on the build, you're building the thing that you think they want. All you want to know is, like, you have something to offer, which is your definition of what you think the company sells and builds. And what you want to talk about is what they actually think the company sells or builds. That's literally what you're offering, perspective. And so that's a really raw example. But as you move along in your career, you discover there's a lot that you have to offer. It might be your identity. It might be the university you're attending. So a multitude of affiliations you have, both professional and [personal], but you don't even know it. You don't even know it yet until you start to talk to people or [...] their background that they came from a certain geography or something. And so I think

38:25 Jon McLachlan

you speak a certain language, perhaps, like you can

38:28 David Carpe

go and do something. Like you're really, you're like an IC2, but you're also like pretty good at bass guitar or you're really good at needlepoint or cooking Indian foods. Or I have no idea. But there's always something. There's always something that you can do and that you can offer people. The challenge is, do not do that cold outreach, connecting with people, establishing rapport, and through that rapport, discovering what [affinities], what you might share in common. That assumes you'd like to develop some functional chemistry and dialogue. And I think any young person who's interviewed knows how to participate in a conversation. If they're socially awkward, that's a different thing to address. How literally, like the way you broach a conversation, but [...] there's immense value, and that's how you get to meet people outside your company.

39:17 Jon McLachlan

Just to close the gap on like the social awkwardness thing as something that, you know, I went through myself. It was always like very anxious with new people and didn't know how to start conversations. There's actually a lot of structure to that, and it's really simple. And there's a book out there, it's called How to Talk to Anyone About Anything.

39:36 David Carpe

Yeah, I don't know.

39:37 Jon McLachlan

It just goes. Do you know this book?

39:39 David Carpe

I know other. I've not read it, but I know what you're talking about.

39:41 Jon McLachlan

Yeah, it's a very good book. It just, it encourages you to think about here's the structure of like small talk, and here's how to not sound like a creep. And then you go practice it. And you practice it with low-risk people, just whatever on the sidewalk and in a cafe, like, or jobs where people that are [paid] to be nice. People in the hospitality industry are [nice to you]. So they're not going to be [mean]. It's a very safe space to practice that stuff. Okay. Tell me, David, what's the strangest place that you've ever networked with somebody?

40:13 David Carpe

God, I've had some weird connections on plane flights. I'm trying to think of some weird

40:20 Jon McLachlan

Are you one of those people where if I sit next to you on a plane, like we can share like our life story and we'll get to know each other super well?

40:27 David Carpe

Yeah, it depends. So, I used to do a lot of conferences, and it's funny. So, I like what you're talking about. I got out of college and it was, I would go talk to people and I would turn [beet red]. I was so nervous. I was so [...]. I remember when I was in LA, I was still doing art, and there was a like a corporate, I don't know, some kind of corporate art show. And I got a drawing in from [...]. I was like the representative, I had this nice drawing or something. Ned Johnson came to the art show. Now, if you know, Johnson was the founder of Fidelity, so as far as I knew in my 20s, he was definitely like one of the wealthiest men in the world, if not like the wealthiest on the East Coast. He was like [this titan of] industry. So when you're that young, I was like, I was so nerdy. I was already a red, sweaty guy when I met people, right? Then I [...], I'm like stuttering. It's so awkward. Yeah. And then I, at some point, I don't know when, there was some kind of metamorphosis. And I think it comes with age. I don't know. I was, I like dramatically, I was a very self-confident person outside of like public speaking stuff. And then suddenly I was like, oh no, I can do this. I don't know what, can't explain. I was like [...] in my mind. I started doing conferences, speaking in front of hundreds of people. All of a sudden, I could talk to anyone. I could cold call anybody. I could approach anybody in a room, work a room, go to a bar, go to whatever. And I love doing that because I'm a relentless bullshitter. And a huge piece of [why] I wound up in this career is that I realized what I enjoy most wasn't like [MBA in] finance or building a project at a startup. It was this like endless connectivity, this like tissue that connects everybody. It's just [...] people. And so you can get really good at that. You can do really interesting things with it. You don't have to be a recruiter. You could be an operator. You could be a sales guy. You could be a [...] person. You could be a security person with that. You could do anything with a network. I just chose to do something that was network-intensive. I think when you get into speaking, like, there are all sorts of like tips, tricks, books that help people facilitate that thing?

42:26 Jon McLachlan

Facilitate, yeah, because there's structure to it. And then you go practice and then it becomes second nature, you don't even think about it.

42:31 David Carpe

So, you know what? It reminds me of, there's some movie with Steve Martin, and I know, some, one of his many bad movies, but there was a scene I remember where he was at this dinner party and it was like LA, right? So it was all these like LA people, and it was this woman in very LA with her big LA hair. And she was sitting quietly at her, with her fork and knife at her table. He went over and he said, oh, I [heard] this, whatever, Carol. I heard you're taking a course in conversation, the art of conversation. And she turned to him. She said, yes. Well, it was like, and that was a joke. But I feel like if people do it wrong, that's where the conversations go. They ask close-ended questions, yes, no questions. You like, you always want to avoid that stuff early in a [...] chatty kind of dialogue. But yes, yeah, yes, yeah. But it was, a, that's what it makes me think of. But I think for young people, I think they underestimate their appeal sometimes to older people. That's another whole thing. So if you're like a 20-something, I'm telling you, network with some 40-year-olds, not like 20 and 30-year-olds, and reach out to the line executives at your company, the VP of marketing, if you can, the VP of sales, not the director, not the manager. Trust me. If you're even remotely intimidated by it, just put that out of your mind. These are just people. I talk to them every day. They're your neighbors. Or maybe they're your parents' friends, if they're that much older than you. But they're all, we're all sentient beings. Everybody, unless they're evil, is generally [out for] people's. And you already got something in common. It's, it's, you're, you're in the same [culture],

44:01 Jon McLachlan

working together towards the same vision, right?

44:03 David Carpe

Yeah. And honestly, yeah. And I think for young people, too, if they, when you get somebody who does what you want to do, this is just too much to get into in a short time. But if you bump into somebody, you get an introduction or a connection or something to someone who literally does something that you think you want to do. Like you are an early career software engineer, but you're pretty sure now you're five years in, you're really drawn to products. You think you ought to move into product management. You're not even sure yet how to get there, but you know that. And you bump into, or in your own company, there's like a, like a group PM who looks like somebody, like, who also came from engineering and whatever, literally just send that person a note, just say to them, hey, I was looking at your background on LinkedIn. We work together. Can we talk? Because I think a lot about moving into product and I just don't understand how you do it. I guarantee you that person will carve out like an hour or two hours. They will probably start mentoring you. You'll probably start meeting once a month. And now you have this like amazing connection. That one connection also is a conduit to that person's entire network of recruiters who call for product roles, industry connections, grad school friends, whatever it is. Like every connection, any of your readers who've looked at social network analysis and they've looked at, you look at like betweenness and degree centrality, you start to look at how a network works and you realize you could be that [hub]. Like, you don't have to be a distal point. Like, you actually always are the [hub]. The only thing you have to do to make that work is believe. Like, you have to believe that you're the [hub]. And I don't mean [...], don't go tell people that you're the [center of the] universe. Just remember that your network revolves around you. You're the [center] of your network. You overlap. So, what you're always thinking about as a giver is where in your network is there something that's complementary to the one that you're scratching at or touching? And it starts, getting older, it just takes time. You get [older], you do it more, it just becomes a long-term investment, right? But, but when you're in your 30s, it becomes just so easy to see who should know who. Like you meet somebody, it's like, oh, you got to meet my friend so-and-so. Oh, you live there, like the same things you do in your personal life, you just improve them professionally. Yep.

46:19 Jon McLachlan

David, thank you so much for coming on the show.

46:22 David Carpe

Yeah, thanks for having me.

46:23 Jon McLachlan

Would you like to leave our listeners with any final words of wisdom? Maybe advice for your younger self that you never received, but you wish you, you had heard?

46:32 David Carpe

Yes. One quote, Timothy Leary, the electric, if your readers are familiar with Timothy Leary, they can Google. If you don't know who he is, go Google him. He said, never forget your transcendental aspirations. And that is my message to young people. Focus on your career. If you're in tech, like if you seriously, you want to plug into a startup, like a hot start, reach out to me. If you put my website or my email or something, we'll get all your contact. And if I, if it's, I'm going to inundate it, I'll figure it out. But if it's like a handful of people, I'll talk to them to give them advice one-to-one. But I'm telling you, if your career is of interest, focus on that. But I will tell you, you're doing that while you're focused on building your career, doing these things, and giving yourself over, even if it means [100-hour] weeks at your own startup for five years and you burn out and whatever, don't lose sight of the things that fascinated you and held your imagination when you were a teenager, when you were in college or whatever it was. Like if you are, if you didn't take that women's dance class [...], but you thought it would have been interesting, I'm making this up because my father took women's dance and then studied anthropology, but she really wanted to do women's dance. So she took those classes. So if you think you want to do it, but you didn't do it, it's like it's never too late. It's never to go explore these things because if you [...], you're going to turn around like these people I know who do everything right. And then they're like decades later, it's like they're having this existential crisis. They don't know exactly what to do with it. [Except] now they're 50 and they're 45 and they have money and infinite choice. It's even worse. They're blinded by, or they're crippled by inability to realize what motivates them. All they know is that they could do anything and they follow a predictable pattern. You know what they do? They become angel investors. They become limited partners in venture funds. They become interim executives or operators.

48:26 Jon McLachlan

And a number of angels that I've met trying to like just participate in that journey, the rush, for the high, like, is an incredibly high number.

48:36 David Carpe

Right. So I'll tell you what, you want to be an angel investor and you're not sure and you're not sure what to do. Why don't you just, for one investment, for one investment, instead of investing in a startup, why don't you go do something philanthropic if you have a lot of money? Maybe go, my friend [built a well] in Burkina Faso. And he actually went there. His wife is from Burkina. This is my best friend. So they went there to build this well and spent time there. But that's something that actually didn't cost a lot, but for them, it's a lot of money. But it's a way, I'm just, this is an outlandish example, but I'm saying there's something that [holds] your interest, like, and it's a humanitarian cause or it's a hobby, but it has nothing to do with a software company. It has nothing to do. I'm just encouraging people.

49:15 Jon McLachlan

I couldn't agree more. Philanthropy is very important to me. Firstly, I'll be doing, I'm actually the team captain of an AIDS LifeCycle ride where we're going to ride from San Francisco down to LA. It's 545 miles.

49:27 David Carpe

[It's awesome.]

49:27 Jon McLachlan

We've got four of us doing it. Yep. And all of the money that we're raising for this ride, and all, it's going to go into [ending AIDS] and HIV research.

49:37 David Carpe

It's huge. You can also do it other ways. So, for example, and this is a shameless promotion, but I've been volunteering with U.S. Digital Response for quite a while. And that's like U.S. Digital Service is a volunteer-based organization, pandemic response. Some really incredible people come to us because you're basically just responding to federal, state, and local needs. So think about the pandemic. Think about the state of Louisiana. Do the best engineers you know from college apply to the state of Louisiana to work on payroll systems or unemployment collection claims processing? So this is what these people are struggling with. There's armies of volunteers who are doing what they love. They work in tech and they're taking their know-how, their project management skills, their build experience, and they're helping at a civic, they're doing civic tech. And so they do things that are actually improving society with their competencies. I'm not rich enough to do philanthropy, but I do what I can at small scale. I like, what you can do is, but I also do it in the form of services and helping out organizations like volunteer teaching, things like that. You can do that too. If you love engineering, but you want to take a break, go teach kids to code, man. You could probably throw a baseball that hit one or two schools within a couple of miles of your house or apartment. [They could] desperately use a young, skilled engineer to work with some junior high kids or grade school kids and just introduce them to computing. Introduce them to languages. Get them on Bubble. Do some no-code development, something cool. I don't know.

50:58 Jon McLachlan

David, thank you so much. This has been amazing.

51:02 David Carpe

Yeah, [...]. Thank you.

51:05 Jon McLachlan

Yeah, we have some time to [...] so that this is good.

51:09 David Carpe

Yeah.

51:10 Jon McLachlan

All right. And thanks to all of our listeners for tuning in to another episode of the Security Podcast in Silicon Valley. [...] Thanks, everyone.