All right, welcome to Dalton Plus Michael. Today, I think we're going to 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? What are we going to be doing today?

Yeah, I'll just ask them. I feel like what kind of office hours is this? What advice do you want to hear from me?

Let me start off with like a really common example I hear is, which is they'll be like, oh, we got an offer to get acquired. 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 going to do it and that you just want to tell me about it in a roundabout way. And you want me to be excited for you.

Yes.

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

Exactly.

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

It's funny because we have this concept in YC called shopping for advice, right? We often say some version of, if you already know what you want to do, you know, step one is to go talk to a bunch of advisors and find one of the groups with you. Do the thing, do the thing.

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 the other 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. In which case like. The design of the front page is not really the top, you know, it's like, 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 will leave in and, you know, telling you love those where they just like slip it in at the very end.

What would you do if you only had three months of runway?

As a founder, I think you can just be upfront, 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 want to draw a line around stuff where I'm not going to give good answers. And I want to have like a really solid board. Tell me what my customer wants. I don't know, right? Or like, summarize the entire history of my industry for the past 25 years, or can you make a list of every investor who likes investing income? So it almost is when I create like a border and be like, hey, don't ask me in this area.

On the flip side. I love 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. 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? What's on your to-do list and what's the order? How do you think about that?

One of the meta piece of advice that we always get 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. That's like 20% of my calendar is lawyers. So here's how we advise founders out there to do what lawyers. You ready, folks?

Tell the lawyer what you want and give them constraints. And then ask for legal advice. And the reason is if you don't do that, they can go way out of scope and often will go like red line 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.

But Dalton, that takes work. Like they're the expert. They've done this under 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? To tell me what to do, right? Isn't that, isn't that your job advisor?

I think that these folks are used to having clients that give them advice. And so what happens to startup founders are inexperienced is they never learned this lesson. Like this is one of those lessons you learn in practice, which is you kind of want to rein in, you want to ring fence. Here's the type of legal advice I'm looking for. Make sure I don't go to jail. Make sure something really bad isn't happening. Otherwise, I want to get this deal done, sign the deal.

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

I think you want to explain what kind of advice you're looking for. Like, what is your goal of the advice session? Like, hey, do you think right now is a good time to fundraise? Okay, that's like a good agenda to ask an investor. But if it's completely open-ended, you tend to get extremely random advice.

Yeah, and random in this context is probably not what you're looking for. Now, okay, I'm going to play devil's advocate. 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 order. Can we talk about the sprained ankle? 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? Let's talk about the important thing, not.

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 kind of read between the lines when it's like filler content.

Filler content. Exactly.

And they just don't want to go for the main topic. A founder that I worked with a few years ago wrote a LinkedIn post. It was pretty funny. It's one of those, you know, where they anonymize what partner told them they advised me. And they're like, our first office hours at YC, we had one agenda item, which is, should we rename our company to a better.com? And our YC partner told us to not waste our, his time like this ever again, and to come back when he had a real problem. And then, and then in the wrestling tempo, he was like, this was the best advice we ever got. You know, it was just so awesome. And, you know, I wanted to be like, just at me next time, you know.

Getting good advice requires some prep. Sometimes people are elevated into these, you know, Oracle style figures and it's kind of like... You know, even if you talk to a way, who's in Oracle? Peter Thiel is in Oracle. You talk to Peter Thiel, he does nothing about your business. You're not raising any agenda. You're completely focused and just like, tell me things that could help my startup. 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 want to 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?

It's a great question because I've seen this backfire. And so when I was a new YC partner It was like, okay, Dalton, you know a lot about consumer and the music industry. So let me ask you questions about the entertainment industry. And...

Run!

Okay, A, that's a really small set of expertise that's not useful. B, it was stuff I never wanted to talk about. And C, I missed the point where I actually think the stuff that I was best suited to talk about was things like hiring and firing and growth. We had a lot of growth. If I suited you, you were both growth experts when we were Yeah, early in our career as start advisors on raising I knew a lot about actually a lot of developer tools.

how would have found to know that about you know you're the you're the music guy right yeah with the founder actually get a real dossier?

That's a great question I think you want to realize that. just looking at the superficial parts of someone's bio may miss the points. And I think you would have known that I was someone that wanted to talk about developer tools and infrastructure a lot and was really interested in it because you would have saw that I was a programmer and that I was really into open source. I think you would have been able to figure that out even when I was a new partner. 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. He probably has a lot of opinions about that. That would be a good way to do it.

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 that people wouldn't even expect. I mean, like, I don't know, like developing country lending.

where are our extras on that?

Yeah. And sometimes I think what founders are really trying to do is figure out everyone else who I 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 sort of. And if the answer is I have never funded anyone in your category, let's get that out right away.

You know, often times I get founders ask me some version of like, well, how have you seen other companies in their category die? And I'm like, that is a really good question. Like I can go through that. So how would you wrap this up? I'm a founder. What would you put in my mind before going and talking to an investor or any type of advisor?

I think it's almost like how you would view any meeting, which is what is my goal of this meeting? And so before you even have it, what would you view success as? 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 there talking. And that's okay. 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. I just want to like talk things through. I'm like, great. Copy to provide that service. Um, and so I think, yeah, having a personal goal for what the outcome is from eating with someone I think is a good idea.

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 kind of gave me a stomach ache? And to your point, one of them often is, I'm not having fun.

Yeah. We have low morale. We feel bad and we want to talk about it. And again, that's totally cool. Let's do it. Like let's talk through it.

I think maybe 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 the only factor in the quality of what we give you back.

Well, again, it goes back to prompting, which is if you type in a really generic lane prompt, you're probably going to get a generic lane answer. But if you spend the time to craft a really good prompt with a lot of unique aspects to it, you'll get really interesting answers.

Well, and oftentimes when you're super honest about something that you think is really bad, our reaction's like, Oh, no. You see that. You think that's bad. But when you hide that, you might leave that meeting being like, oh, we're totally screwed and not needed. Now you know what type of device to ask for.