EVERY SPOKEN WORD
25 min read · 5,009 words- 0:00 – 1:29
How YC office hours handle “Should we pivot?”
- MSMichael Seibel
It's never been easier or a better time to change your idea because of how fast you can grow. And if you're gonna re-roll, please don't get into pivot hell. Like, like [laughs] like, that's not actually obviously better. This is Dalton plus Michael, and today we're gonna talk about should you pivot? We've never been asked questions about startup pivoting-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
... before, so this is fresh, fresh content.
- DCDalton Caldwell
I would say this is the most common topic that I got as a YC partner-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... uh, for someone that wanted to book office hours with me, and this would be like the title-
- MSMichael Seibel
Yes, yes
- DCDalton Caldwell
... of the office hours, what I want-
- MSMichael Seibel
Especially someone that wasn't your-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... someone you didn't fund. [laughs]
- DCDalton Caldwell
Yeah, someone was like, "Dalton, I need to talk to you."
- MSMichael Seibel
Yeah, first in for this one. [laughs]
- DCDalton Caldwell
And this would be, this would be the topic.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And so I got very, um, practiced at doing this office hours, and I think something great about these videos is we can kinda give you, the audience, um-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... an office hours experience without, uh, meeting with all of you.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
So I think we'll kinda go from there, right?
- MSMichael Seibel
So let me try to ask you some kind of, uh, a setup question. So, um, what's the difference in kind of how you would take an office hour like this when you're talking to a founder who is maybe three or four months in and, and kind of afraid of their lack of progress versus a founder who was two years in? How, in your mind, were you calibrating slightly differently based on just that?
- 1:29 – 2:07
The “doctor” approach: diagnose before prescribing a pivot
- DCDalton Caldwell
The first thing that I would do, uh, my framework for this type of office hours, was I kinda would think of myself like a doctor.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
Where, you know, when you go to the doctor's office, you, you don't get out the prescription pad. At least not a good doctor.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
You're not like, "Okay, well, here's your prescription." You know, that would be, I think, deeply unethical, I think would be the term-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... for that. Um-
- MSMichael Seibel
I came in for a hurt shoulder.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Here's your shoulder surgery.
- DCDalton Caldwell
Here's some pills. It's been great.
- MSMichael Seibel
[laughs] Yeah.
- DCDalton Caldwell
Um, and instead what I would do is spend a large amount of time at the beginning of the office hours-
- MSMichael Seibel
Mm-hmm
- DCDalton Caldwell
... asking a lot of questions.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Just like what a good doctor would do-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... is they would wanna assess you. They would wanna look you all over. They would ask family history.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
There's just, like, all this context that you need-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... to make a diagnosis as a doctor.
- MSMichael Seibel
Yes.
- 2:07 – 3:14
Key diagnostic questions: backstory, alignment, reality check, and the “next best option”
- DCDalton Caldwell
And so the way that I would diagnose a case of the pivots, um, would be [laughs] would be to ask, "Okay, remind me the backstory of the company."
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
"How long have you guys been working on this idea?"
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
"When did the founders come together?"
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
"How much alignment do you have, uh, between the founders that you're working on the right idea?"
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
"Objectively, how is it going? Do you agree objectively of how it's going?"
- MSMichael Seibel
Hmm.
- DCDalton Caldwell
And then I would always like to ask, "What is your next best option?" So I would say, "Okay, so you're asking about pivoting. Do you have an idea, like, in the, in the can here? Or-
- MSMichael Seibel
Hmm
- DCDalton Caldwell
... are you just in the abstract-
- MSMichael Seibel
Pivoting into a blue ocean
- DCDalton Caldwell
... TBD.
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
Um, 'cause again, on that point, just, let's just say that they said, "Oh, Dalton, we do have other ideas." I'd be, "Well, what are they? What are your top three?"
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Because sometimes their top number one backup idea was phenomenally good.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
[laughs] And they put a lot of time and thought into it.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
And so my diagnosis would be like, "Well, that sounds, it sounds like you're pretty high conviction on that idea, and you're-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... you've thought about it a lot. Maybe you should look at that," versus, "Oh, we have no other ideas. We're just asking you this very abstract question."
- MSMichael Seibel
Mm-hmm.
- 3:14 – 3:42
A simple time-based heuristic: too early vs. too long stuck
- DCDalton Caldwell
I would tend to be like, "Well, so I'll, I'll pause here." And so the, the way I think about this is there's, like, a decision tree of asking a ton of questions, uh, about the founder's context.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
And, and as per what you said a moment ago, Michael, if it's a company that's been in the batch for four weeks and has not talked to a single customer and has no other ideas, generally be like, "Yeah, you probably shouldn't pivot. Like, you should at least try."
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
[laughs] But if you've been working on it for three years and it's going nowhere, yeah, you should, you should probably pivot, right?
- 3:42 – 4:43
Two founder archetypes: fear-driven early pivots vs. informed pivots
- MSMichael Seibel
On average, founders know less about the problem that they're trying to solve than they think, and there's this kind of frame of, like, I'm gonna start this company because I know the right solution, which is, like, a helpful frame to convince yourself to, like, do the idiocy of starting a company. But the reality, in my mind, is that in the first couple years of a company, you're actually trying to figure out everything.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Like, you're trying to figure out what the customer's problem is. Can it be solved? Is it worth solving? Everything. And what I find is that I encounter, and this is very, very generalized, two types of founders. I encounter a type of founder who, like, once they realize their vision of the world is slightly different, um, than what the world's turning out to be, they get scared, and they're like, "This seems like a harder problem than I thought, but I think this problem over here is easier. I wanna kinda run away-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... from the hard." And that's kind of what I tend to see as the early pivoter.
- 4:43 – 6:18
The “dentists” and other ‘easy’ pivots: chasing what feels simple
- DCDalton Caldwell
100%. And, uh, the, let me give you the textbook example, and-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... um, I mean this from a pr- place of love, audience, if any of you are working on this idea. This is not, I'm not trying to give you a hard time, but the classic one was s- company's working on some idea.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
And they're like, "Okay, we're gonna pivot. We're thinking dentists." Like, for some reason-
- MSMichael Seibel
Oh, God
- DCDalton Caldwell
... dentists was the thing where it seemed really easy.
- MSMichael Seibel
Dental offices?
- DCDalton Caldwell
Yeah, like somehow-
- MSMichael Seibel
Yeah, yeah, yeah, yeah. Fill out the forms for you and the-
- DCDalton Caldwell
They're like, "Yeah, this thing sounds hard-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... but I was asking ChatGPT, and I think we're going dentists."
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And I'd be like, "Oh, another one of these." [laughs] That was like-
- MSMichael Seibel
Oh
- DCDalton Caldwell
... the classic pivot. But anyway-
- MSMichael Seibel
I thought you were gonna go the, the, uh, the user interview product.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
That was another classic, uh, yeah.
- DCDalton Caldwell
That was. And again, I'm sure there's some great dental startups.
- MSMichael Seibel
Sure.
- DCDalton Caldwell
We love you. Like, no-
- MSMichael Seibel
For sure
- DCDalton Caldwell
... no diss. I just... That one was a great example of a startup idea that feels easy. For whatever reason-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... a lot of founders-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... searching for an easier startup idea-
- MSMichael Seibel
Yes
- 6:18 – 6:55
A practical rubric for dev tools: do you actually use your own product?
- DCDalton Caldwell
I think that's fair. Uh, another, another rubric I would do in my diagnosis is if it was a developer tool-
- MSMichael Seibel
Mm-hmm
- DCDalton Caldwell
... I would say, "Okay, are you all using this yourselves?"
- MSMichael Seibel
Yeah. Oh, God, that's a big one.
- DCDalton Caldwell
And it was, it was actually surprising how many companies building a developer tool could not be bothered to use their own product to build their own company.
- MSMichael Seibel
That was the whole thesis-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
... about pivoting or doing a developer tool. It's like, if you're a developer [laughs] here's the area you know really well. [laughs]
- DCDalton Caldwell
Yeah, and someone's like, "We spent six months building this AI coding thing or whatever," and I'm like, "Well, cool. Are you, are you using it on a daily basis?" And they're like-
- MSMichael Seibel
"No, we're using Cursor."
- DCDalton Caldwell
"... You know, we'll get back to you on that."
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Um, that was generally a sign that it probably wasn't the right space for them, or at the very least-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... they're not on the right track.
- 6:55 – 8:48
AI changes the pivot calculus: assumptions break faster, opportunity cost rises
- MSMichael Seibel
Yeah. So let's just say everything we've talked about before, I think I believe in the pre-AI world and the post-AI world. Let's talk about how the AI world changes this concept of pivoting. One of the things that I see is that a lot of hypotheses that founders had about how the world works for companies that were started, you know, let's say before February this year. That was my awakening. Maybe it was-
- DCDalton Caldwell
It was, like, December, but clo-
- MSMichael Seibel
December last year
- DCDalton Caldwell
... Yeah, it was, like, the Claude code, uh-
- MSMichael Seibel
Right
- DCDalton Caldwell
... Yeah, yeah.
- MSMichael Seibel
Maybe AI is kind of proving some of those hypotheses wrong, and so let's talk about a company where it's basically like their set of assumptions, oh, it takes 100 developers to build blank, or it takes a lot of humans to do Y, or the best we can do to improve a process is improve the UI and some screens and some workflows. What do we think about pivoting to some, to those companies where maybe, like, the core assumption's just wrong now?
- DCDalton Caldwell
Yep.
- MSMichael Seibel
And, like, maybe we don't... They don't have to be two years in. Like, they're going out to customers now, and their base of customers are just like, "This is categorically not what's going on." Ha- But maybe they've raised some money, and they're excited, and da, da, da, da. Like, how do you think about that kind of case?
- DCDalton Caldwell
This is very nuanced feedback, and I'm glad I have video to do this 'cause I don't know how I would tweet this. This is-
- MSMichael Seibel
Yeah, yeah, yeah
- DCDalton Caldwell
... way too subtle of a point.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
So here's what I would say. It's never been easier or a better time to change your idea because of how fast you can grow-
- MSMichael Seibel
Yep
- DCDalton Caldwell
... and the growth rates are real. And so you're taking a bigger opportunity cost than ever to keep grinding on an idea that structurally was rendered obsolete by Claude Code or what have you, right? It's super clear.
- MSMichael Seibel
Can I extend that? I would also argue that AI probably opens the opportunity aperture, so it's probably was m- more-
- DCDalton Caldwell
Yes
- MSMichael Seibel
... opportunity post-AI than pre-AI.
- 8:48 – 10:13
Avoiding “pivot hell”: the danger of weekly re-rolls and hype chasing
- DCDalton Caldwell
And the nuance here, though, is I would be really sad if people were watching this video and it causes them to get into pivot hell. [laughs]
- MSMichael Seibel
Yeah, no, yeah.
- DCDalton Caldwell
And let me define pivot hell. It's where you change your idea every week-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... and you just rotate through whatever you read about on social media, and you have no conviction.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
You're just chasing hype, and you're... Yeah, like you have no conviction. You have no ideas. You're just a vessel for what you read about on X.com.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And-
- MSMichael Seibel
And what just raised money
- DCDalton Caldwell
... it would be so sad if someone watched this video and I accidentally got them into pivot hell.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And so the nuance here is it's such a fine line. It's such a delicate balance for the viewer to, yeah, you know, it's not working. You should probably roll the dice again. Like, you get a re-roll in the age of AI.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
And if you're gonna re-roll, please don't get into pivot hell. Like, like, [laughs] like, that's not actually obviously better. And so again, there's some, some feedback I would give or there's, there's some structure that I would give someone when they're choosing ideas, which is try to find an idea that you know something about. Try to find an idea that you can get early customers on. Try to find an idea that is not just a regurgitation of who's raising lots of money. Like, try to avoid the obvious-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... you know-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... gravitational pull towards pivot hell, which again, is a very bad place to be. It's better, it's honestly better to be working on kind of a not great idea than be in pivot hell, which is-
- MSMichael Seibel
Well, yeah, yeah, yes
- DCDalton Caldwell
... very nuanced, again, what, what we're saying is-
- 10:13 – 12:38
Why founder-domain connection matters (Twitch story)
- MSMichael Seibel
Yeah, yeah, yeah. Yeah, very nuanced. I think that if we could blind poll a lot of early stage founders and they would never get attributed back to them, I think a common belief is that most of the companies that win, those founders kind of like played around in the sand and figured something out, and this whole idea of knowing something about what you're working on is not true. Like, the stories are much more like, "This seemed cool, and I tried it out, and I just ran a bunch of experiments, and this ended up working," versus like, "I actually had some kind of deep connection to this idea space, something about it." And I think what's so frustrating to me is that when I look at the winners, I can always tie, or more, w- way more often than not, I can tie some deep connection to what the founder was into. And you know, I think we lived this personally in Twitch, and it was, it was weird to watch 'cause I think there was this initial phase where, like, we were trying to make celebrities, and Justin-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... was the first one, and he wanted to be a celebrity. Like, we were solving his problem. Then there was this kind of middle phase where all we cared about was graphs and metrics and are more people coming to the website. And then there was the phase that worked, which was kind of Emmett caring about video games, and he somewhat irrationally cares about video games.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
And it's so funny when I go through so many stories of startups, and I kind of get to the meat of like, "So why are you doing this?" And then there's some like, "Oh, my dad was a pharmacist," or, "I grew up in a restaurant." Like, you know, there was like an actual... And I always think to myself, if you're competing against somebody where you're just doing the random walk of what sounds like a good idea and they're doing something that like-
- DCDalton Caldwell
If they're doing their life's work and you're just, like-
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
... hanging out-
- MSMichael Seibel
Trying to get lucky
- DCDalton Caldwell
... who's gonna win?
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
And so it's, like, so it, it doesn't seem counterintuitive to say this, but it's like- Your best dice roll is in a game you know how to play. Like, your best shot, even if it seems out of vogue, is probably something that you know something about before you sat down to think about startup ideas. And like, I don't think people like to hear that, 'cause they're like, "I grew up in a middle-class family, and I went to a good school, and I had no problems." How do you advise someone on how to figure out what the next thing is if the th- you're convinced-
- DCDalton Caldwell
Right
- MSMichael Seibel
... the thing isn't working?
- 12:38 – 13:50
Treat pivoting like a personal tendency: pivotitis vs. never-pivoting
- DCDalton Caldwell
There, there's two things I would do. Number one, my diagnosis would be to understand if their natural state is to pivot too much or too little.
- MSMichael Seibel
Mm.
- DCDalton Caldwell
And so do you have a case of pivotitis?
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Or do you have a case of, like-
- MSMichael Seibel
Yeah, I don't have a name for it. All right
- DCDalton Caldwell
... uh, the, the opposite.
- MSMichael Seibel
The opposite.
- DCDalton Caldwell
And if someone was already pivoting every week, I'd actually prescribe to them, "Don't pivot for, uh, three months."
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Like, force yourself to work on this long enough to learn something.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
'Cause right now, you're getting such surface level insights-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... to just work on an idea for a week and then change again.
- MSMichael Seibel
You're learning nothing.
- DCDalton Caldwell
You're learning nothing.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
This is, you're wasting-
- MSMichael Seibel
Waste of time [laughs]
- DCDalton Caldwell
... your time to pivot every week.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
So, you know, my prescription is work, pick any idea, I don't even care what it is, but force yourself to work on it for three months-
- MSMichael Seibel
Yep
- DCDalton Caldwell
... so that you have enough time to learn something.
- MSMichael Seibel
What about the opposite?
- DCDalton Caldwell
And now the opposite would be they've been working on something for two years and it's still not working at all. And so I'd be like, "Just do something else." Like, it'd be, the prescription is just try some stuff-
- MSMichael Seibel
Mm
- DCDalton Caldwell
... because your natural order is to, is to never try anything new. And also, that advice is always much harder for a hard tech company-
- MSMichael Seibel
True
- 13:50 – 16:28
Platform shifts and inertia: the iPhone analogy for the AI moment
- MSMichael Seibel
So let's wrap this up with kind of two interesting thoughts, and I, I will desperately try not to make them depressing, but here I go. One observation that I think we've both shared is that there were a large number of mobile startups, um, funded pre the iPhone App Store. There were folks that were building on top of BlackBerry, on top of feature phones, on top of Palm OS, on top of Microsoft. Like, all of these were, were smartphone platforms pre iOS. And as far as I can tell, none of the big mobile winners started until after the new platform was adopted. And so what gives there, right? 'Cause I think that if I'm a first principles thinker, I would say, here's a company who already understands the power of smartphones, who already has a software, a, a s- a product live in smartphones, who has funding, who has engineers. Wouldn't they have so much more of an advantage-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... against someone who's starting fresh now that they have an iPhone in their hand? They're like, "Oh, I, here's what I wish it could do."
- DCDalton Caldwell
I think if I wanted to engage with that thinking, it's that it's a disadvantage to have inertia working on the wrong thing, and that if you spent a lot of time and effort porting your mobile game to BlackBerry-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... when the iPhone comes out, you're gonna have a lot of cope to not basically just reboot your whole company.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Like, the day the iPhone comes out, you're like, "Okay, well, we're gonna lay everyone off, and we're gonna throw away all the code we spent years building, and we're gonna admit to our investors we were wrong." And I think there's probably some founders who have the wherewithal to do that.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
Um, most people don't. I think where you're going with this is that's kinda happened with AI, where a lot of companies that have been around for a while-
- MSMichael Seibel
Mm-hmm
- DCDalton Caldwell
... they need to either-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... be like, "Well, we're just rebooting everything. You know, like, all that stuff that we spent millions of dollar- all that code we wrote, uh, it's worthless, and it can be replicated in two months with Claude code. Thanks for playing." [laughs]
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
And, and, I mean, and basically you have to almost, like, declare emotional bankruptcy on your existing business-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... to truly reboot it.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
That is such a hard thing to do, versus a brand-new company, there is no emotion. They're like, "Cool, we just started yesterday."
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And so-
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
... it's almost like an existing company has to, to put themselves on a level playing field with a brand-new company-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... they have to go through the emotional state of letting all that stuff go, and letting go of all the sunk costs before. Most people can't, won't choose not to do that, right, man?
- 16:28 – 21:08
How later-stage companies can reboot: secondary, break-even discipline, and bolder moves
- MSMichael Seibel
Like, what I'm hoping is that this cycle is different. And, and here's what I've seen, um, and I've got a couple companies in the back of my mind. One thing I've seen is that a lot more companies, um, that kinda got later stage pre-AI, the founders took some secondary off the table. And, like, in a weird way, that's kind of helpful. Like, in a weird way, that kind of gives them the freedom to say, like, "I can take a bigger bet, because if this didn't work out, at least I already got some secondary off the table." So I'm seeing that. And then second, I think that a lot of founders, maybe due to some of our advice, I don't know, when they went through COVID and they saw the crazy times, they got financially more responsible.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
So it's a lot easier to think about these big moves when you're running your business at break even, versus, like, you've got this train, and if you can't keep towing the line-
- DCDalton Caldwell
Yeah. If you're like, "Oh, no, the board's gonna fire me."
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
Like, if you feel like the, the hatchet's hanging over your head-
- MSMichael Seibel
Harder
- DCDalton Caldwell
... it's much harder to be like, "Hey, all the stuff we did is worthless."
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
Like, like, that's a much harder pitch.
- MSMichael Seibel
Harder pitch.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Harder pitch.
- DCDalton Caldwell
Harder to explain that to your board.
- MSMichael Seibel
And so I've seen a couple companies kind of in this position, um, really reboot.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
And, like, what's fun about watching it is that, like, in some ways, if they can get their mind around this cope, it's an advantage. Like, their ambition level's high. They actually are good at what they do. Like, they got this business so far. They're actually kind of, like, talented. Oftentimes, if they're AI-pulled, they can kind of look at all the stuff they've done before and see, "Oh, we could've done it like this," and they can actually package that up and use it.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
And oftentimes they had time to learn about some customers, some markets, some problems. You have some insights. So I hope, and, and maybe I'm, I'm optimistic that this cycle's different, but I think that if I was a founder of a company between, let's say, uh- 10 million in revenue and 300 million in revenue, and most of that business was built on pre-AI assumptions, this is a moment, right? Like, five years from now, you're gonna look back at this moment and you ask yourself some really hard questions. What, like, I might argue that, like, if you're a company at 500 to a billion in revenue and good economics and maybe you can IPO in the next year or two, maybe you can, like, sneak over the bar. [laughs] But if you're n- not there, that bar is moving, and I think sometimes I talk to founders and, and, and I'm just like, "Look, you gotta make a bigger move than maybe you think."
- DCDalton Caldwell
Yep.
- MSMichael Seibel
And it's so hard.
- DCDalton Caldwell
And it's almost like they know it. They just feel unable to make the move. They're like, "Yeah, I know, I know, but-"
- MSMichael Seibel
But this, but that.
- DCDalton Caldwell
There's a but, right?
- MSMichael Seibel
Yeah, yeah. Like, if they were advising another company, they would tell them to make the move. [laughs]
- DCDalton Caldwell
Yeah, yeah.
- MSMichael Seibel
And it's, it's, it's hard, but I'll tell you, folks are doing it. Folks who are starting products at zero revenue-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... that have tens of millions of revenue, and, like, what you mentioned before, AI's a powerful tool. You can grow fast.
- DCDalton Caldwell
Sure can.
- 21:08 – 23:45
What a good pivot feels like: “coming home” to your unique expertise
- DCDalton Caldwell
No extra points. And I guess my, my final thought for more early stage founders-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... that I would always give people, there's a, there's an old video where I talk about pivoting. It's still on the, the YC channel. I think it's called, like, All About Pivoting.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
And one of the, one of my comments is the best pivots are getting closer to the founder's zone of expertise.
- MSMichael Seibel
Yes, yes.
- DCDalton Caldwell
A good pivot feels like coming home.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And so what I would say is if you're at this precipice of pivoting, you should ask yourself, "What makes me special?"
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
"What am I best in the world at?" And sometimes you don't know. Uh, something that I would do as a YC partner a lot is tell the founder what made them special. I would look at their LinkedIn, I would look at their resume, and I'd be like, "Wow, you were writing papers about this, like, really esoteric topic-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... as an undergraduate. How about that?"
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And they'd be like, "Oh, I never thought about that, Dalton. I was too busy, you know, worrying about dentists." And I'd be like, "Well, like, seems like you know a lot about this thing you were writing papers about."
- MSMichael Seibel
And how much do you know about dentists again? [laughs]
- DCDalton Caldwell
Right. Seriously. And, and it was, sometimes when you're in your own little world-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... you forget-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... what makes you special and different and what you're a world expert at. And so I would just really encourage the audience-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... to do that inventory of your upbringing, of where you're from, of the jobs you've had, even internships you've had.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
And you might have more super elite expertise than you realize.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And that's such a great source to move towards and not away from.
- MSMichael Seibel
I love that thought because what most founders will do, will say, "None of those things are hot right now."
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
And it's like, yes, we're aiming for it looking good 10 years from now.
Episode duration: 23:46
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