How To Get Better Advice

1. 0:00 – 0:23

   Surface problems vs. the real issue: morale and not having fun

   1. DCDalton Caldwell0:00

      If I'm super honest, what are the three things in my business that kinda gave me a stomachache? And to your point, one of them often is, I'm not having fun.

   2. MSMichael Seibel0:09

      Yeah. [laughs]

   3. DCDalton Caldwell0:09

      Like, we're, we're-

   4. MSMichael Seibel0:11

      This-

   5. DCDalton Caldwell0:11

      We have low morale.

   6. MSMichael Seibel0:12

      Yeah. [laughs]

   7. DCDalton Caldwell0:13

      We feel bad.

   8. MSMichael Seibel0:13

      Yeah.

   9. DCDalton Caldwell0:13

      And we wanna talk about it, and that's totally cool. Like, that's-

   10. MSMichael Seibel0:16

       On the agenda. [laughs]

   11. DCDalton Caldwell0:17

       Let's do it. Like-

   12. MSMichael Seibel0:18

       Yeah. [laughs]

   13. DCDalton Caldwell0:19

       Let's talk through it. [upbeat music]

2. 0:23 – 0:47

   The key question for office hours: what advice do you actually want?

   1. MSMichael Seibel0:23

      All right. Welcome to Dalton + Michael. Today, I think we're gonna ask a question that I think as office hour givers we've learned to ask ourselves quite a bit. When a founder comes in to talk to us, I think the question we sometimes ask ourselves is, exactly what advice does this person want? [laughs]

   2. DCDalton Caldwell0:41

      Yeah. Well, and here's-

   3. MSMichael Seibel0:41

      What are we gonna be doing today? [laughs]

   4. DCDalton Caldwell0:43

      I'll just, I'll just ask them.

   5. MSMichael Seibel0:46

      [laughs]

3. 0:47 – 1:28

   Acquisition offers as a case study in hidden agendas

   1. DCDalton Caldwell0:47

      I'd be like, what kinda office hours is this? What advice do you wanna hear from me? Let me start off with, like, a really common example I hear.

   2. MSMichael Seibel0:54

      Please.

   3. DCDalton Caldwell0:54

      Which is, they'll be like, "Oh, we got an offer to get acquired."

   4. MSMichael Seibel0:59

      Yes.

   5. DCDalton Caldwell1:00

      "What do you think we should do?" And I will say, "Look, let's be real. Is what's going on here you've already decided that you're gonna do it-

   6. MSMichael Seibel1:08

      Yep

   7. DCDalton Caldwell1:08

      ... and that you just wanna tell me about it-

   8. MSMichael Seibel1:10

      Yes

   9. DCDalton Caldwell1:10

      ... in a roundabout way, and you want me to be excited for you?

   10. MSMichael Seibel1:14

       Yes. Or...

   11. DCDalton Caldwell1:14

       Or, do you not wanna do it and you just need the pep talk that it's a good idea to not take it?

   12. MSMichael Seibel1:20

       Exactly.

   13. DCDalton Caldwell1:20

       So I've just learned to ask that at the front of the office hours. [laughs] And it's, it's actually helpful for both parties to know which way they wanna take it, right?

4. 1:28 – 2:29

   ‘Shopping for advice’ and why misalignment creates bad meetings

   1. MSMichael Seibel1:28

      It's funny, because we have this concept in YC called shopping for advice, right? And we often say some version of, if you already know what you wanna do, y- you know, step one isn't go talk to a bunch of advisors and find one who agrees with you. [laughs] Like, just like, do the thing.

   2. DCDalton Caldwell1:46

      Just do it.

   3. MSMichael Seibel1:46

      Like, do the thing.

   4. DCDalton Caldwell1:48

      Yeah.

   5. MSMichael Seibel1:48

      Where I get in trouble as an advice giver is when the topic is meta advice and I don't realize it. Like, when the topic is, like, I want a cheer-up, and I think the founder actually wants to talk about practical things to do-

   6. DCDalton Caldwell2:05

      Yeah

   7. MSMichael Seibel2:05

      ... in their startup, you know? And I'm sitting here trying to get details, and they're really trying to tell me, "I'm thinking about shutting it down."

   8. DCDalton Caldwell2:12

      Right. [laughs]

   9. MSMichael Seibel2:14

      In which case, like, the design of the front page is not really the talk. [laughs] You know, it's like-

   10. DCDalton Caldwell2:19

       No, and then what they'll do is they'll bring it up in the final two minutes. They'll be like, "Oh, by the way, three of the four founders are leaving," and, you know. [laughs] Don't you love those-

   11. MSMichael Seibel2:27

       Yes

   12. DCDalton Caldwell2:27

       ... where they just, like, slip it in-

   13. MSMichael Seibel2:28

       Yes

   14. DCDalton Caldwell2:28

       ... at the very end?

5. 2:29 – 3:49

   Use agendas and state constraints—plus know what not to ask

   1. MSMichael Seibel2:29

      What would you do if you only had three months of runway? [laughs] Like, as a founder, I think you can just be up front, right? Like, the best teams have agendas, but not just kind of like, what do I think the advisor wants to talk about? Like, actually what's our purpose here? The other thing that comes up a lot is as an advice giver, I'm always telling myself, "I just don't know enough facts on the ground." Or, actually, said more broadly, I wanna draw a line around stuff where I'm not gonna give good answers.

   2. DCDalton Caldwell2:58

      [laughs]

   3. MSMichael Seibel2:58

      And I wanna have, like, a really solid border. It's like, tell me what my customer wants. Like, I don't know, right? Or like, summarize the entire history of my industry for the past 25 [laughs] years. Or, can you make a list of every investor who likes investing in... [laughs]

   4. DCDalton Caldwell3:15

      [laughs]

   5. MSMichael Seibel3:17

      So I almost just wanna, like, create, like, a border and be like-

   6. DCDalton Caldwell3:20

      Yeah

   7. MSMichael Seibel3:20

      ... "Hey, don't ask me in this area." [laughs] Where on the flip side, I love y- your thoughts on this, I find that what I'm really good on is trying to probe the founder on where should they be focused. And we talked about this a little bit before about hedging, but, like, oftentimes I kind of find myself asking questions over and over again, like, what's the best opportunity? What's the biggest problem? W- w- what's on your to-do list, and what's the order?

   8. DCDalton Caldwell3:46

      Yeah.

   9. MSMichael Seibel3:47

      A- a- how do you think about that?

6. 3:49 – 5:05

   A model from working with lawyers: tell them what you want and the constraints

   1. DCDalton Caldwell3:49

      One of the meta piece of advice that we always give is to learn how to work with lawyers, and I'm going through this a lot. We're leading rounds into companies, and so I'm dealing with a lot of lawyers right now, man.

   2. MSMichael Seibel3:58

      Yes.

   3. DCDalton Caldwell3:58

      That's like-

   4. MSMichael Seibel3:58

      Can't

   5. DCDalton Caldwell3:58

      ... 20% of my calendar-

   6. MSMichael Seibel3:59

      Can't

   7. DCDalton Caldwell3:59

      ... is lawyers.

   8. MSMichael Seibel4:00

      Okay.

   9. DCDalton Caldwell4:00

      So here's how we advise founders out there to-

   10. MSMichael Seibel4:02

       Yeah

   11. DCDalton Caldwell4:02

       ... to deal with lawyers. You ready, folks?

   12. MSMichael Seibel4:04

       Yeah.

   13. DCDalton Caldwell4:05

       Tell the lawyer what you want and give them constraints.

   14. MSMichael Seibel4:09

       Yes.

   15. DCDalton Caldwell4:09

       And then ask for legal advice.

   16. MSMichael Seibel4:12

       Yes. Yes.

   17. DCDalton Caldwell4:13

       [laughs]

   18. MSMichael Seibel4:13

       Yes.

   19. DCDalton Caldwell4:13

       And, and the reason is if you don't do that, they can go way out of scope, and often will go, like, redline a lot of documents and come up with all these extraneous points. You're basically the boss of the lawyer. Like, they're service providers.

   20. MSMichael Seibel4:27

       But Dalton, that takes work.

   21. DCDalton Caldwell4:29

       [laughs]

   22. MSMichael Seibel4:29

       Like, they're the expert. They've done this 100 times. I just want them to do it. I just want them to tell me the answer. Isn't that why I pay them? Same with an advisor, right?

   23. DCDalton Caldwell4:38

       Yeah.

   24. MSMichael Seibel4:38

       Just tell me what to do, right? Isn't that, isn't that your job, advisor? [laughs]

   25. DCDalton Caldwell4:43

       I think that these folks are used to having clients that give them advice, and so what happens with startup founders that are inexperienced-

   26. MSMichael Seibel4:49

       Yeah

   27. DCDalton Caldwell4:49

       ... is they never learned this lesson. Like, this is one of those lessons you learn in practice-

   28. MSMichael Seibel4:53

       Yes

   29. DCDalton Caldwell4:53

       ... which is you kinda wanna rein in, you wanna ring-fence, here's the type of legal advice I'm looking for. Make sure I don't go to jail.

   30. MSMichael Seibel5:00

       [laughs] Mm-hmm.
7. 5:05 – 5:41

   Applying the ‘constraints’ model to investors and advisors

   1. MSMichael Seibel5:05

      How would you apply those same thinkings to when someone is talking to their angel investor or their advisor or their friend doing startups and trying to get advice?

   2. DCDalton Caldwell5:12

      I think you want to explain what kind of advice you're looking for. Like, what is your goal of the advice session?

   3. MSMichael Seibel5:21

      Yeah.

   4. DCDalton Caldwell5:21

      Like, "Hey, do you think right now is a good time to fundraise?"

   5. MSMichael Seibel5:24

      Yes.

   6. DCDalton Caldwell5:24

      Okay, that's like a... That's a good agenda to ask an investor.

   7. MSMichael Seibel5:28

      Yes.

   8. DCDalton Caldwell5:28

      But if it's completely open-ended, you, you tend to get extremely random advice. [laughs]

   9. MSMichael Seibel5:34

      Yeah, ran- and random in this context is probably not what you're looking for. Now, okay, I'm gonna play devil's advocate.

   10. DCDalton Caldwell5:40

       Yeah.

8. 5:41 – 7:01

   When the agenda is wrong: calling out the ‘sprained ankle’ problem

   1. MSMichael Seibel5:41

      I've been accused of this. I assume you've been accused of this before, where a founder comes in and their agenda is missing the core issue. It's like, "Hey, we've been shot eight places. There's a hole in our, our aorta. Can we talk about the sprained ankle?"

   2. DCDalton Caldwell5:57

      Yeah.

   3. MSMichael Seibel5:57

      And there's a whole sprained ankle agenda. When-Do you feel like you need to be like, "Hey, why are we even talking about this?" Like, "Hey, can, let's talk about the important thing, not the unimportant thing."

   4. DCDalton Caldwell6:09

      I think it's when you can sense that someone is dancing around the core topic. And again, you could be, I could be wrong, but sometimes I can kinda read between the lines-

   5. MSMichael Seibel6:18

      Yeah

   6. DCDalton Caldwell6:19

      ... when it's, like, filler content.

   7. MSMichael Seibel6:20

      Filler content, exactly. Yeah.

   8. DCDalton Caldwell6:21

      And they, they, they just don't wanna go for the main, uh, topic. A founder that I worked with a few, uh, years ago wrote a LinkedIn post, and it's pretty funny. It's one of those, you know, where they anonymize what partner told them the advice.

   9. MSMichael Seibel6:32

      Yeah.

   10. DCDalton Caldwell6:32

       It wasn't me.

   11. MSMichael Seibel6:33

       Mm-hmm.

   12. DCDalton Caldwell6:33

       [laughs] And they were like, "Our first office hours at YC, we had one agenda item, which is should we rename our company to a better .com?" And the partner told us-

   13. MSMichael Seibel6:42

       Rejected the premise. [laughs]

   14. DCDalton Caldwell6:44

       Yeah, the part-

   15. MSMichael Seibel6:44

       [laughs]

   16. DCDalton Caldwell6:45

       Our YC partner told us to not waste our and his time like this ever again-

   17. MSMichael Seibel6:49

       [laughs]

   18. DCDalton Caldwell6:49

       ... and to come back [laughs] when he had a real problem. And then, and then in the rest of the LinkedIn post, he's like, "This was the best advice we ever got."

   19. MSMichael Seibel6:55

       [laughs]

   20. DCDalton Caldwell6:56

       You know, "This is so awesome," and you know, I wanted to be like, "Just at me next time," you know? [laughs]

9. 7:01 – 8:27

   Getting the right expertise: don’t rely on superficial bios

   1. MSMichael Seibel7:01

      Yes. Getting good advice requires some prep. Sometimes people are elevated into these, you know, oracle-style figures, and it's kinda like y- you know, even if you talked to... Wait, who was an oracle? Peter Thiel is an ora- like, even, you talked to Peter Thiel, he knows nothing about your business. You're not raising any agenda. You're completely unfocused, and it's just like, "Tell me things that could help my startup," [laughs] then you're maybe not setting things up for success. The other bit on this that I think is a little bit tricky is how often you wanna make sure you're getting the right expertise out of the person you're talking to. Like, how would you advise founders to understand what the person they're talking to is actually expert in and what they're not expert in?

   2. DCDalton Caldwell7:44

      It's a great question because I've seen this backfire.

   3. MSMichael Seibel7:47

      [laughs]

   4. DCDalton Caldwell7:48

      And so when I was a new YC partner-

   5. MSMichael Seibel7:51

      Yeah

   6. DCDalton Caldwell7:52

      ... it was like, "Okay, Dalton, you know a lot about consumer and the music industry."

   7. MSMichael Seibel7:56

      Mm-hmm.

   8. DCDalton Caldwell7:56

      "So let me ask you questions about the entertainment industry." And-

   9. MSMichael Seibel8:00

      Run. [laughs]

   10. DCDalton Caldwell8:01

       [laughs] Okay, A, that's a really small set of expertise that's not useful.

   11. MSMichael Seibel8:06

       Yes.

   12. DCDalton Caldwell8:06

       B, it was stuff I never wanted to talk about, and C-

   13. MSMichael Seibel8:08

       Yes

   14. DCDalton Caldwell8:08

       ... it missed the point, where I actually think the stuff that I was best suited to talk about was things like hiring and firing-

   15. MSMichael Seibel8:15

       Mm-hmm

   16. DCDalton Caldwell8:15

       ... and growth. We, I had a lot of growth. In fact, so did you. You were growth.

   17. MSMichael Seibel8:18

       Yeah, yeah, yeah.

   18. DCDalton Caldwell8:19

       We were both growth experts-

   19. MSMichael Seibel8:20

       Yeah

   20. DCDalton Caldwell8:20

       ... when we were-

   21. MSMichael Seibel8:21

       Yeah

   22. DCDalton Caldwell8:21

       ... you know, early in our career as startup advisors. Fundraising, I knew a lot about. Um, actually a lot of developer tools. So how does-

10. 8:27 – 9:54

    How to research an advisor’s real strengths (portfolio, technical background, interests)

    1. MSMichael Seibel8:27

       So this is something [laughs] how would a founder know that about you? You're the, you're the music guy, right?

    2. DCDalton Caldwell8:31

       Yeah.

    3. MSMichael Seibel8:31

       Like, how would the founder actually get a real dossier?

    4. DCDalton Caldwell8:34

       That's a great question. I think you wanna realize that just looking at the superficial parts of someone's bio may miss the points, and I think you would've known that I was someone that wanted to talk about developer tools and infrastructure a lot and was really interested in it-

    5. MSMichael Seibel8:48

       Mm-hmm

    6. DCDalton Caldwell8:49

       ... because you would've saw that I was a, that I was a programmer-

    7. MSMichael Seibel8:52

       Yeah

    8. DCDalton Caldwell8:52

       ... and that I was really into open source. I think you would've been able to figure that out-

    9. MSMichael Seibel8:55

       Okay

    10. DCDalton Caldwell8:55

        ... even when, when I was a new partner.

    11. MSMichael Seibel8:56

        Mm.

    12. DCDalton Caldwell8:56

        And then now you could look at my portfolio, and if you were to look at my portfolio and be like, "Wow, Dalton has funded a lot of open source companies."

    13. MSMichael Seibel9:02

        Yeah.

    14. DCDalton Caldwell9:02

        "He probably has a lot of opinions about that."

    15. MSMichael Seibel9:04

        Yeah.

    16. DCDalton Caldwell9:05

        That would be a good way to do it.

    17. MSMichael Seibel9:07

        I definitely found founders being much more interested in my operating past than my investing past. You know, you and I have funded so many companies in so many industries-

    18. DCDalton Caldwell9:18

        Yep

    19. MSMichael Seibel9:18

        ... that people wouldn't even expect. I mean, like, I don't know, like, developing country lending, you know? [laughs]

    20. DCDalton Caldwell9:24

        We're, we're experts on that.

    21. MSMichael Seibel9:26

        Yeah. And, and sometimes I think what founders are really trying to do is figure out everyone else who I have funded in their general category and kind of try to get out of me what I've learned, and I wish sometimes they had just asked that straight up. [laughs] You know? Like... And if the answer is, "I have never funded anyone in your category-"

    22. DCDalton Caldwell9:44

        Yeah.

    23. MSMichael Seibel9:44

        "... let's get that out, like, right away." [laughs]

    24. DCDalton Caldwell9:46

        Yeah.

    25. MSMichael Seibel9:47

        You know, oftentimes I get founders ask me some version of like, "Well, how have you seen other companies in our category die?" And I'm like, "That is a really-

    26. DCDalton Caldwell9:53

        That's a good question

    27. MSMichael Seibel9:54

        ... good question."

    28. DCDalton Caldwell9:54

        Yeah.

11. 9:54 – 10:38

    Define success for the meeting: decisions, clarity, or ‘therapy’

    1. MSMichael Seibel9:54

       Like, I can, I can go through that. So how would you wrap this up, right? I'm a founder. What would you put in my mind before going and talking to an investor or a, any type of advisor?

    2. DCDalton Caldwell10:05

       I think, I think it's almost like how you would view any meeting, which is what is my goal of this meeting?

    3. MSMichael Seibel10:10

       Yes.

    4. DCDalton Caldwell10:10

       And so before you even have it-

    5. MSMichael Seibel10:12

       Yes

    6. DCDalton Caldwell10:12

       ... what would you view success as?

    7. MSMichael Seibel10:14

       Yes.

    8. DCDalton Caldwell10:14

       Is it getting answers to these questions? Is it talking through your feelings so you feel better? Again, a lot of office hours really are-

    9. MSMichael Seibel10:21

       Therapy

    10. DCDalton Caldwell10:21

        ... talking. Yeah, and that's okay.

    11. MSMichael Seibel10:23

        Yeah.

    12. DCDalton Caldwell10:23

        But if, if, if what the founder wants to do is they're like, "Hey, honestly, I've just been having a really hard time the past few months."

    13. MSMichael Seibel10:27

        Yeah.

    14. DCDalton Caldwell10:27

        "I just wanna, like, talk things through," I'm like, "Great."

    15. MSMichael Seibel10:30

        Yeah.

    16. DCDalton Caldwell10:30

        "Happy to-

    17. MSMichael Seibel10:30

        Yeah

    18. DCDalton Caldwell10:31

        ... provide that service."

    19. MSMichael Seibel10:32

        Yes.

    20. DCDalton Caldwell10:32

        Um, and so I think, yeah, having a personal goal-

    21. MSMichael Seibel10:35

        Yes

    22. DCDalton Caldwell10:35

        ... for what the outcome is-

    23. MSMichael Seibel10:36

        Yes

    24. DCDalton Caldwell10:36

        ... for meeting with someone I think is a good idea.

12. 10:38 – 12:05

    Be brutally honest and specific: better input yields better advice

    1. MSMichael Seibel10:38

       I think the only thing I would add is, like, what are the top three real problems in my business? Not pop problems or fake problems or things I read about Twitter, but, like, if I'm super honest, what are the three things in my business that kinda gave me a stomachache? And to your point, one of them often is, "I'm not having fun."

    2. DCDalton Caldwell10:55

       Yeah. [laughs]

    3. MSMichael Seibel10:55

       Like, we're, we're-

    4. DCDalton Caldwell10:57

       This sucks.

    5. MSMichael Seibel10:57

       We have low morale.

    6. DCDalton Caldwell10:58

       Yeah. [laughs]

    7. MSMichael Seibel10:59

       We feel bad.

    8. DCDalton Caldwell11:00

       Yeah.

    9. MSMichael Seibel11:00

       And we wanna talk about it.

    10. DCDalton Caldwell11:00

        Yeah.

    11. MSMichael Seibel11:01

        And again, that's totally cool. Like-

    12. DCDalton Caldwell11:03

        On the agenda. [laughs]

    13. MSMichael Seibel11:04

        Let's do it.

    14. DCDalton Caldwell11:05

        Yeah. [laughs]

    15. MSMichael Seibel11:05

        Like, let's talk through it.

    16. DCDalton Caldwell11:07

        I think maybe the, the only last thing I will say is in this setting, honesty is so important. I mean, the quality of what you give us is, is the only factor in the quality of what we give you back.

    17. MSMichael Seibel11:18

        Well, again, it's, it goes back to prompting, which is if you type in a really generic, lame prompt, you're probably gonna get a generic, lame answer.

    18. DCDalton Caldwell11:25

        Yeah.

    19. MSMichael Seibel11:25

        But if you spend the time to craft, like, a really good prompt with a lot of unique-

    20. DCDalton Caldwell11:28

        Yeah

    21. MSMichael Seibel11:28

        ... aspects to it-

    22. DCDalton Caldwell11:29

        Yeah

    23. MSMichael Seibel11:30

        ... you'll get really interesting answers.

    24. DCDalton Caldwell11:32

        Yes. [laughs] Well, and oftentime, when you're super honest about something that you think is really bad, like, our reaction's like, "Oh, no. Oh, you see that?"

    25. MSMichael Seibel11:40

        [laughs]

    26. DCDalton Caldwell11:40

        "Like, you think that's bad?" [laughs] But when you hide that, you might leave that meeting being like, "Oh, we're totally screwed."

    27. MSMichael Seibel11:47

        Yeah.

    28. DCDalton Caldwell11:47

        And it's not needed. Now you know what type of advice to ask for. Cheers.

    29. MSMichael Seibel11:53

        Thanks. [upbeat music]

Episode duration: 12:05