How To Build A Successful Career In Tech: Where To Join, When To Leave

1. 0:00 – 1:34

   Career leverage comes from finding “pockets of talent”

   1. DCDalton Caldwell0:00

      We worked with Sam when he started OpenAI, and Sam was like, "X, Y, Z is gonna happen." Anyone that was like, "Okay, Sam," like, "I'll follow you," did great.

   2. SPSpeaker0:08

      Yeah.

   3. DCDalton Caldwell0:09

      And 98% of people were like, "No, no, no, no, no, no."

   4. SPSpeaker0:11

      That's crazy.

   5. DCDalton Caldwell0:12

      And so there's- there's often super talented people that you know are talented, that people still choose to ignore. [upbeat music]

   6. SPSpeaker0:20

      This is Dalton + Michael, and today we're gonna talk about how to have a successful career in tech. So we know there are a lot of people who watch our videos, not all of them doing startups. And we know a lot of the startup founders, well, this might be news to you, so a lot of the startup founders, their startups might not work out and they might get jobs in tech. And so, this video's for you. And let's be clear, most people think about a successful career as how do we make money.

   7. DCDalton Caldwell0:46

      Yes.

   8. SPSpeaker0:47

      A- and deep fulfillment, but also money.

   9. DCDalton Caldwell0:49

      Yes.

   10. SPSpeaker0:49

       So-

   11. DCDalton Caldwell0:50

       To paraphrase, How to Get Rich?

   12. SPSpeaker0:54

       [laughs]

   13. DCDalton Caldwell0:55

       [laughs] Is that-

   14. SPSpeaker0:55

       If we were paraphrasing, each- [laughs]

   15. DCDalton Caldwell0:59

       Step one. Um, what it's like to live and work in Silicon Valley for as long as I have, it's been like 30 years-

   16. SPSpeaker1:06

       Mm-hmm

   17. DCDalton Caldwell1:06

       ... is you see waves and cycles, but one underlying truth is that there are pockets of talent-

   18. SPSpeaker1:14

       Yes

   19. DCDalton Caldwell1:15

       ... where the smartest people are at any one time.

   20. SPSpeaker1:19

       Yes.

   21. DCDalton Caldwell1:19

       You can kind of figure out where they are, we'll talk about how in a second, and talent is mobile.

   22. SPSpeaker1:25

       Yes.

   23. DCDalton Caldwell1:26

       And so you'll see the talent move from company to company as the industry changes, as new technologies come out.

   24. SPSpeaker1:34

       Yes.

2. 1:34 – 2:17

   Spotting the hot company early: the Google-on-campus example

   1. DCDalton Caldwell1:34

      To start with, just give you some examples, you know, when I was an undergrad, um, at Stanford in, like, the late 2000s, Google was the hot new startup that was recruiting on campus.

   2. SPSpeaker1:46

      Mm-hmm.

   3. DCDalton Caldwell1:46

      And a lot of my professors had affiliations with Google, and so I knew that Google-

   4. SPSpeaker1:52

      The talent

   5. DCDalton Caldwell1:52

      ... was a really cool... Like, it was, it was aware to me as an undergrad that something was happening there-

   6. SPSpeaker1:58

      Yeah

   7. DCDalton Caldwell1:58

      ... and that really smart people worked there.

   8. SPSpeaker2:01

      Really early.

   9. DCDalton Caldwell2:01

      Yes.

   10. SPSpeaker2:02

       Pre-IPO, pre, da, da, da, yes.

   11. DCDalton Caldwell2:04

       Definitely pre-IPO.

   12. SPSpeaker2:05

       Yes, yes.

   13. DCDalton Caldwell2:06

       Right? And like, you know, prior generations, Sun Microsystems, like there were other-

   14. SPSpeaker2:09

       Yes, yes

   15. DCDalton Caldwell2:10

       ... sorry to even use the term, but cracked engineers.

   16. SPSpeaker2:12

       [laughs]

   17. DCDalton Caldwell2:12

       Like where all the cracked engineers work.

   18. SPSpeaker2:14

       Yeah.

   19. DCDalton Caldwell2:15

       You can kinda ask around-

   20. SPSpeaker2:16

       Yes

   21. DCDalton Caldwell2:16

       ... and people would tell you.

3. 2:17 – 3:19

   Geography and “following the doers”: leaving the wrong pond

   1. SPSpeaker2:17

      I think from my story, I thought Yale was gonna be this deep talent pocket. Certainly a lot of smart people, but, like, probably not as differentiated as I thought when I was in high school. And then, for me, it was about moving geographically. It was about, um, finding Justin Kan and Emmett Shear, who actually were talented, and seeing how they first went to Y Combinator, a pocket of talent, and then they went to Silicon Valley, a pocket of talent. And it was interesting because I had a survey of my friends, and I can't say that this was, like, a plan, but it's, like, interesting that I followed these two people. [laughs]

   2. DCDalton Caldwell3:01

      [laughs] And it worked out. It worked out.

   3. SPSpeaker3:02

      [laughs] It worked out. And these two people, I don't know who they were following, but they got the fuck out of Du- like, right? Like, it was like they had a nose that New Haven, Connecticut or New York or Cambridge was not where the pocket was developing. They had a nose they had to be in the Valley.

4. 3:19 – 4:56

   The “Bob” blueprint: tracing talent through PayPal → Palantir → OpenAI

   1. DCDalton Caldwell3:19

      I'll give you a couple other anecdotes just from even college. I remember I was friends with this guy named Bob.

   2. SPSpeaker3:24

      Okay.

   3. DCDalton Caldwell3:25

      Bob was a good programmer.

   4. SPSpeaker3:27

      Yeah.

   5. DCDalton Caldwell3:27

      Um, and he dated this girl that lived in my dorm, and so he was always at my dorm.

   6. SPSpeaker3:31

      Yep.

   7. DCDalton Caldwell3:31

      And so I talked to Bob constantly. Like, I just like, I always-

   8. SPSpeaker3:35

      It's amazing

   9. DCDalton Caldwell3:35

      ... would see Bob, and I remember Bob telling me that he got an internship when he was, like, a sophomore or junior at this tiny startup in Palo Alto called PayPal.

   10. SPSpeaker3:43

       Mm-hmm.

   11. DCDalton Caldwell3:44

       And I was really curious, and he told me all about how actually the job was all about defending against the Russian mob.

   12. SPSpeaker3:52

       Mm, [laughs] mm-hmm, mm-hmm.

   13. DCDalton Caldwell3:53

       Like apparently PayPal was just getting, like-

   14. SPSpeaker3:54

       Yeah. [laughs]

   15. DCDalton Caldwell3:55

       ... destroyed by organized crime.

   16. SPSpeaker3:57

       [laughs]

   17. DCDalton Caldwell3:58

       And he was like, "Yeah, so we're building all this, like, hardcore technology to fight, like, the Russian mob."

   18. SPSpeaker4:03

       Yes, money laundering.

   19. DCDalton Caldwell4:03

       Yeah. [laughs]

   20. SPSpeaker4:04

       To fight money laundering.

   21. DCDalton Caldwell4:04

       And so basically, I, I loved talking to him about his weird internship at this tiny startup called PayPal.

   22. SPSpeaker4:09

       Yeah.

   23. DCDalton Caldwell4:09

       And he was an elite engineer and he was saying, "Oh, all the other people that work here are really good."

   24. SPSpeaker4:14

       Mm-hmm.

   25. DCDalton Caldwell4:14

       Then Bob went to Palantir 'cause it was the same people. Then Bob, after, like, eight years at Palantir, went to OpenAI.

   26. SPSpeaker4:24

       Yeah, yeah.

   27. DCDalton Caldwell4:26

       And most recently Bob was the chief scientist of OpenAI.

   28. SPSpeaker4:30

       [laughs]

   29. DCDalton Caldwell4:31

       I think he created thinking models. And, like, that's my friend from the dorms.

   30. SPSpeaker4:34

       There it is.
5. 4:56 – 6:01

   Relationship-building is part of the strategy

   1. SPSpeaker4:56

      Well, I love the point about paying attention where, where, where they go. You actually have to build relationships. Like, you got to know this Bob. I talked to this person who wanted to start a company and they said to me, "In college, the software engineers weren't cool. They weren't the people you should get to know. It wasn't obvious." And so this person was like, "I never made friends with them." And so it's like that talent pool was there. In hindsight-

   2. DCDalton Caldwell5:24

      Yeah

   3. SPSpeaker5:24

      ... it was obvious that you should have followed them, but you never got to know them well enough to know that that was actually interesting talent pool. So you kinda not only have to be around talent, you have to engage with those people and become friends with them.

   4. DCDalton Caldwell5:38

      Yes.

   5. SPSpeaker5:38

      Which is, I think, like, hilariously, like, I think for me it's like those are the people who are fun to be friends with.

   6. DCDalton Caldwell5:45

      Yes.

   7. SPSpeaker5:45

      But those are often not the coolest kids.

   8. DCDalton Caldwell5:48

      Yes. I, I-

   9. SPSpeaker5:51

      [laughs]

   10. DCDalton Caldwell5:51

       Um, indeed. I, I, I'm gonna, I'm not gonna add anything to that. Yeah, I'll let that stand.

   11. SPSpeaker5:57

       Yes.

   12. DCDalton Caldwell5:57

       Um-

   13. SPSpeaker5:58

       Their value accrues over time, perhaps. [laughs]

6. 6:01 – 6:20

   You don’t have to be the smartest—just identify and listen to them

   1. DCDalton Caldwell6:01

      And, and again, to me, the, the lesson ... is that you don't have to know everything. You don't need to even be-

   2. SPSpeaker6:08

      Yes

   3. DCDalton Caldwell6:08

      ... the smart person to have a great career in tech. But you need to know who the smart people are-

   4. SPSpeaker6:13

      Yes

   5. DCDalton Caldwell6:13

      ... and listen to what they say carefully.

   6. SPSpeaker6:15

      It's like the hunter follows the dog, and the dog's on the scent.

   7. DCDalton Caldwell6:19

      Yes.

   8. SPSpeaker6:19

      Yeah. Yes.

7. 6:20 – 6:39

   Following conviction: the Sam Altman / OpenAI example

   1. DCDalton Caldwell6:20

      I mean, it's like, you know, we, we worked with Sam when he started OpenAI-

   2. SPSpeaker6:23

      Yeah

   3. DCDalton Caldwell6:23

      ... and Sam was like, "X, Y, Z is gonna happen." Anyone that was like, "Okay, Sam," like, "I'll follow you," did great.

   4. SPSpeaker6:30

      Yeah.

   5. DCDalton Caldwell6:30

      And 98% of people were like, "No, no, no, no, no, no."

   6. SPSpeaker6:33

      That's crazy.

   7. DCDalton Caldwell6:33

      And so there's, there's often super talented people that you know are talented, that people still choose to ignore.

8. 6:39 – 7:53

   Stop optimizing the wrong things when choosing jobs

   1. SPSpeaker6:39

      Well, let's talk about one of the reasons why people choose to ignore this, because I hear this all the time. When I, when I see some, when I walk, talk to a YC founder who's considering working at a company, or an engineer who's considering working at a company, the things that they talk about, like, frustrate me to no end. Because it's like, look, you're working at a technology company. Fundamentally, a big part of your compensation is gonna be stock, and a big part of you eventually getting rich is that stock being worth something. So, like, my first thought is, like, what is your thesis on why that stock would be worth something? That is like the last thing they talk about. They're like, "Well, here's the people that interviewed me, and like, the interview process or the recruiter I talked to and what the recruiter said," which is like, what? Does that matter? Um, "Here's like the benefits," which is like, this is not what the game, this is not how to win by maximizing your benefits. They say stuff like, "Well, this is the job I'm gonna..." Like, oh, I'm like, "This job would be more interesting versus that job." And it's like, if you're a technology company, you can move around. Your jobs change. Weird geographic stuff. Like, "Oh, I wanna be close to my friends, and they all are into New York, so I wanna go to New York."

   2. DCDalton Caldwell7:48

      Yeah. Ugh.

   3. SPSpeaker7:49

      And it's like, I mean, if you don't wanna win, then, then fine. [laughs]

   4. DCDalton Caldwell7:53

      Fine. [laughs]

9. 7:53 – 9:14

   Think like an investor: underwrite the stock with real business signals

   1. SPSpeaker7:53

      Do whatever you want. [laughs] Like, if you wanna win, there might be some trade-offs. And, and the mentality I always give people is like, look, like, think about how hard investors work to figure out which companies to invest in, and they get to hedge.

   2. DCDalton Caldwell8:06

      Yeah.

   3. SPSpeaker8:07

      You don't get to hedge your time. You can only work with one company at a time. Perhaps in addition to those kind of lifestyle things, you should be asking yourself the question, what is your thesis on why this stock might be worth more money? And the questions that come out, I think, are so much more interesting.

   4. DCDalton Caldwell8:23

      Yep.

   5. SPSpeaker8:24

      You know? Like, are people using the product? To your point about talent, am I ridiculously impressed with the engineers they have talking to me? Is the revenue growing?

   6. DCDalton Caldwell8:35

      Yep.

   7. SPSpeaker8:35

      And like, I'll see people with like these weird things. It's like, "Oh, here's their valuation." And it's like, fine.

   8. DCDalton Caldwell8:41

      Yep.

   9. SPSpeaker8:41

      But like, can you underwrite that valuation? Do you actually understand what's going on in the business? The other thing that's so funny is that good founders wanna share this information. "Oh, w- we've got great customer retention." Of course you wanna tell people that. Bad founders, when you start asking these questions, they're gonna be like, "This, oh, that's private," or da-da-da, you know, weird shit, you know? And you're like, "Oh, really? Like, the selling point, the, what otherwise would be the selling point is private?" That's a hit.

   10. DCDalton Caldwell9:08

       Yeah. The way I'd summarize what you're saying is you gotta think like an investor, and are you long or short-

   11. SPSpeaker9:14

       Yes

10. 9:14 – 10:01

    When to leave: avoiding staying too long without becoming a job-hopper

    1. DCDalton Caldwell9:14

       ... the place? And maybe one other nuance here. I don't know if we have the absolute answer here, but people that are great at having a career in tech know when to leave.

    2. SPSpeaker9:24

       Yes. Yes.

    3. DCDalton Caldwell9:25

       There's a lot of folks that stay too long.

    4. SPSpeaker9:28

       Yes.

    5. DCDalton Caldwell9:28

       And we're not saying-

    6. SPSpeaker9:30

       Gotcha

    7. DCDalton Caldwell9:30

       ... leave after nine months-

    8. SPSpeaker9:31

       Yeah

    9. DCDalton Caldwell9:31

       ... or, you know, we're, we're not saying be a short-termer. That's bad.

    10. SPSpeaker9:33

        No, no.

    11. DCDalton Caldwell9:33

        But like, like our Bob example, Bob changed jobs a small number of times, but they were all pretty good.

    12. SPSpeaker9:41

        Yeah.

    13. DCDalton Caldwell9:41

        And there's a lot of people that went from Google to Facebook to OpenAI.

    14. SPSpeaker9:47

        Yeah.

    15. DCDalton Caldwell9:48

        They didn't stay in any one place that long. And so-

    16. SPSpeaker9:50

        Yes

    17. DCDalton Caldwell9:50

        ... job hopping, bad. But choosing to move on after, what, three to five years, something like that-

    18. SPSpeaker9:58

        Yeah

    19. DCDalton Caldwell9:58

        ... not the worst idea sometimes.

11. 10:01 – 11:10

    Exceptions and variants: lifer cultures, team moves, and big-company pockets

    1. SPSpeaker10:01

       Well, and, and I don't even think it has to be time-based, right? If you want to be in deep density pockets, and every day you're re-underwriting, there's awesome people there I get to work with, I think there's a way to work at Google for 25 years and be in deep density pockets. But I think that's not-

    2. DCDalton Caldwell10:17

       That's true. And like Apple, Apple's such a weird beast.

    3. SPSpeaker10:19

       Yeah.

    4. DCDalton Caldwell10:20

       Everyone there's a lifer. Like, Apple's just such a strange culture-

    5. SPSpeaker10:22

       Yeah

    6. DCDalton Caldwell10:23

       ... where I don't think people, I think you just go there and you stay at Apple forever.

    7. SPSpeaker10:26

       It is rare that you get to build the phone that most of the, like, people u-

    8. DCDalton Caldwell10:31

       [laughs]

    9. SPSpeaker10:31

       Right? Like it's like-

    10. DCDalton Caldwell10:32

        Yeah

    11. SPSpeaker10:32

        ... it's like how, how often do you get to do that? And it's rare that that consumer product is so consistently the best product for-

    12. DCDalton Caldwell10:38

        Yep

    13. SPSpeaker10:39

        ... a decade. So I'll say like m- w- whether you're jumping around between companies, between teams, and this is applies to startups, it applies to big companies, too. Like, I had a friend who just moved from Facebook over to Google because Google's AI products are doing really well, and they were able to get a job inside of Google Brain. And it's like-

    14. DCDalton Caldwell10:57

        Yep

    15. SPSpeaker10:57

        ... that's very interesting. So this doesn't require even touching into the software p- I mean, into the startup pool. But, um, it does also sometimes require you to sacrifice that salary.

    16. DCDalton Caldwell11:10

        Yes.

12. 11:10 – 12:11

    Equity over vanity: don’t optimize titles in a failing company

    1. SPSpeaker11:10

       And I think maybe that's what I wanna end on, is that like you get rich with the equity.

    2. DCDalton Caldwell11:17

       Yes.

    3. SPSpeaker11:18

       That's where you're getting rich.

    4. DCDalton Caldwell11:18

       Yeah. The problem people have is they have vanity and titles and number of reports and all this crap.

    5. SPSpeaker11:30

       Yeah.

    6. DCDalton Caldwell11:30

       You get caught up of like leveling up your character. Like, I got promoted to L62-

    7. SPSpeaker11:34

       Yes

    8. DCDalton Caldwell11:34

       ... and like, you know.

    9. SPSpeaker11:35

       Yes. In the company that's failing.

    10. DCDalton Caldwell11:37

        Yeah.

    11. SPSpeaker11:38

        [laughs]

    12. DCDalton Caldwell11:38

        You, you basically start optimizing for these weird local inside baseball things.

    13. SPSpeaker11:43

        Yes.

    14. DCDalton Caldwell11:44

        And that's a trap, I guess is what we're trying to say.

    15. SPSpeaker11:46

        Super big trap. If you have to consistently underwrite your stock every year, and you have to consistently ask yourself, "What's my thesis why this stock will be worth four or five, 10, 100 times more?" You're gonna get a clear view. All right?

    16. DCDalton Caldwell11:59

        All right.

    17. SPSpeaker11:59

        Thanks, Michael.

    18. DCDalton Caldwell12:00

        Cheers. [upbeat music]

Episode duration: 12:11