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Y CombinatorWhere Do Great Startup Ideas Come From? – Dalton Caldwell and Michael Seibel
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20 min read · 3,926 words- 0:00 – 0:30
Rookie Mistakes
- MSMichael Seibel
In all three of these cases, these folks had the problem, they had experience, and in hindsight, there was an obvious opportunity to make something 10X better. But most people thought they were idiots, and that's probably the overarching theme. They had to be contrarian. Hey, this is Michael Seibel with Dalton Caldwell. Today, we're going to talk about where do great startup ideas come from. We've picked three successful YC companies to unpack this question: Airbnb, Coinbase, and Stripe.
- 0:30 – 0:35
3 common themes
- MSMichael Seibel
And there are 3 common themes that we've seen through all three of these companies. The first,
- 0:35 – 0:48
1. Timing
- MSMichael Seibel
timing was important. For each of these companies, there was a preexisting product, preexisting competitor, dominant you might say, but there was an opportunity to make something that was 10X better than what existed.
- 0:48 – 0:59
2. Idea
- MSMichael Seibel
Number two, most people, founders and investors, thought these ideas were horrible, either because they were too hard to execute or because they just were bad ideas.
- 0:59 – 1:10
3. Market
- MSMichael Seibel
And then number three, and I think the coolest one of them, is that each of these opportunities turned out to be bigger than the founders even knew when they started. They turned out to be way bigger.
- 1:10 – 1:24
AirbnB
- MSMichael Seibel
All right. So let's talk about Airbnb. Um, one of the things that I think is really interesting to set this up is that existing products did exist, right? Airbnb did not come up with this idea.
- 1:24 – 2:47
Competition
- MSMichael Seibel
So what were you using before Airbnb to Airbnb, Dalton?
- DCDalton Caldwell
Yeah, um, for context, I, I think if you, if you've only seen Airbnb, you think they came up with the idea. That's probably if I, if I talked to my mom, she'd say, "Oh, Airbnb is a great idea that those founders dreamed up." Um, but back in the day, I was already using VRBO, um, before Airbnb was even funded by YC or, or existed. There was also a very, uh, popular startup called CouchSurfing, which was quite similar to Airbnb, and it had a lot of mind share, had a lot of, uh... It was a big network. And so it kind of felt like the third-rate entrant [laughs] to a crowded space at the time. I remember when they were in YC, that was my perspective.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Do you remember that, Michael? Had you used any of those? 'Cause I'd used VRBO personally, and I thought it was pretty good.
- MSMichael Seibel
I had used VRBO. I had also used CouchSurfing. Um, one of the reasons why I was actually excited about working with the Airbnb folks was because using CouchSurfing was so painful. [laughs] And so I think that, you know, first thing when it comes to timing, I think they nail this hardcore. They weren't first, but the existing products weren't great. And I think it's interesting to talk about why the existing products weren't great because honestly, um, that's important. I would argue that, like, there were two fundamental facts that made the existing products not good.
- 2:47 – 3:08
Payments
- MSMichael Seibel
The first is that VRBO and Craigslist did not facilitate payments. So when you arranged an, a house share with someone or staying in someone's apartment, you still had to pay them either in cash or check or wire, and there was a lot of friction because it's two people who don't know each other having to trust each other to transmit payments.
- 3:08 – 3:36
Free listing
- MSMichael Seibel
I think the second problem that VRBO had was they charged hosts to list. And if you think about the core insight of this market, it's that hosts are the game. If you can get the most hosts, you win. You have the best inventory. But if you charge them [laughs] upfront to be on your site, uh, like, you're probably doing it wrong. So to me, timing was huge. Existing product did not... There were 10X improvements that could be made. I think
- 3:36 – 4:35
Solving their own problem
- MSMichael Seibel
the second thing that was really interesting was that, um, they were solving their own problem. Like, most people don't realize that Airbnb started because Joe and Nate needed to make rent money, and there was a big conference going on in San Francisco, and they basically rented out f- room on their floor to host people so that they could make some money. And it's funny 'cause we always talk about personal problems, but, like, not being able to pay rent, that's like, that's a real problem, right? [laughs]
- DCDalton Caldwell
[laughs] And that doesn't sound like a vacation rental, which was what I was used to seeing, uh, on VRBO, which was vacation rentals. The-
- MSMichael Seibel
Exactly. Exactly. I think it was interesting at the time that a lot of people realized that they could use their property to make extra money, and it's not a coincidence that this happened around the same time as the '08 crash, where a lot of people needed to make an extra buck, and suddenly they realized, "Oh, I have an asset right now I can make some money on."
- 4:35 – 4:46
Used their own product
- MSMichael Seibel
Then I think the last thing is they used their own product. Airbnb didn't realize the insight around facilitating payments, around accepting payment when they launched.
- 4:46 – 5:04
What were the takeaways when they launched?
- MSMichael Seibel
They didn't have the insight when they launched. You know, Brian came and spoke to YC recently, and he shared the story that when he used his own product and he forgot to bring money for payment and the host thought he was a fraud, he realized, "Oh, crap," like, "Our site needs to allow people to pay." Like, "We have to solve this problem."
- 5:04 – 7:35
Criticisms
- MSMichael Seibel
So it's funny 'cause these insights seems l- obvious now, but Dalton, back in the day, you know, put your investor hat on.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
What were the shit takes? Like, why did everyone think, "Oh, this is a dumb... This is dumb. You should-"
- DCDalton Caldwell
Well, look, there, there's two extremes. One was renting a house when someone is already home, renting a room in a house with a hoster there was, like, the ultimate unappealing, scary, bad thing that no one wanted to do, especially older folks, you know-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... like investor folks versus young-
- MSMichael Seibel
Like investor types. [laughs]
- DCDalton Caldwell
[laughs] You know, it's like-
- MSMichael Seibel
Who had a lot of money and can now can afford nice hotels. [laughs]
- DCDalton Caldwell
Yeah. Why would I wanna go stay in a stranger's apartment in Manhattan? Like, no, thank you, right? So it was extremely unappealing idea. People worried about those sorts of things. Um, and then, like, the other, the other insight I have for you on this one is it was seen as uncool and impure When you're building a community at this time in history to charge money for it. [laughs] Like the CouchSurfing ethos was, was a very like communal, community-based, pay-it-forward, social collective action, decentralized goodness thing, and to be commercial was extremely in poor taste. And remember Michael, you and I both were both founders in this era. All of the messaging that was bombarded from us, from everyone, all of our peers-
- MSMichael Seibel
Yep
- DCDalton Caldwell
... is that making money isn't cool, and being commercial isn't cool. And what they should have done is get as big as they could and, and get 100 million people on Airbnb and then charge once they've built the network. And so to charge, that's a horrible idea, guys.
- MSMichael Seibel
Horrible idea.
- DCDalton Caldwell
Build the network first and then charge, right? Like again, you went through this as a founder, man. Isn't this what-
- MSMichael Seibel
Of course
- DCDalton Caldwell
... you would've been told?
- MSMichael Seibel
It's, it's what we were told. I, I mean, Twitch became big when we started diversifying our business model and then started accepting direct payments from users in addition to ads, but that was seen as dumb back then. So clearly, and of course this is gonna be a common theme, if they had listened to most of the investors or most of the founders at the time, Airbnb wouldn't exist.
- DCDalton Caldwell
Yeah. It'd be like-
- MSMichael Seibel
They wouldn't exist
- DCDalton Caldwell
... well, CouchSurfing is free, so your plan is to build something like CouchSurfing, but with no users and you're just starting, and you're gonna charge money for it? Good luck.
- MSMichael Seibel
Making it up.
- DCDalton Caldwell
That sounds like a suicide mission. [laughs]
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
Right?
- MSMichael Seibel
All right. So,
- 7:35 – 7:46
Coinbase
- MSMichael Seibel
so the next one is Coinbase. So set the scene for Coinbase. Like what do you think Brian saw when he was getting rolling? What was the insight?
- DCDalton Caldwell
Yeah. So I, I was around back then, and I was trying
- 7:46 – 9:22
Buying Bitcoin
- DCDalton Caldwell
to buy Bitcoin back then too, and I remember, um, the Coinbase YC application really well, and the whole historical context. So to set this up for people, circa 2011 and 2012, it was really hard to buy Bitcoin. Really hard. I remember looking into it in around 2011, and there was a step of sending money orders, like going to Western Union and sending a money order to some foreign country, and that's when I opted out of it. I wish I would've done it. Would've made a lot of money.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
But I didn't, 'cause it just seemed too much like a total scam. Like if you're ever sending money orders to foreign countries, something is going wrong in your life, right? Um-
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
But anyway, I also, um, was familiar with Mt. Gox, and Mt. Gox was a, was the biggest and largest Bitcoin exchange back in the day, and, um, it went down a lot, and it got hacked, and everyone lost all their money. I actually lost some money in Mt. Gox personally. Um, I think I had about one Bitcoin in Mt. Gox. I'm not too worried about it. Um-
- MSMichael Seibel
I feel like the reputation for Mt. Gox was like you can get money in, but you can't ever-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
... get any money back out. [laughs] That was the environment where Co- [laughs] Coinbase was coming of.
- DCDalton Caldwell
And what's great is that Mt. Gox was an acronym that was Magic: The Gathering Online Exch- Online Exchange. It was originally a website to trade Magic cards that they pivoted into, into Bitcoin. And so anyway, um, the historical insight was buying Bitcoin was something people wanted to do, but all of the options were pretty bad. That's the historical context, and, and Brian wanted to fix that.
- MSMichael Seibel
I think what's really interesting about this is we come back towards he wasn't
- 9:22 – 9:33
Not the first mover
- MSMichael Seibel
the first mover. Was not the first mover, but the product that existed was so bad that a 10X better product was actually within reach. Like it was actually possible. I think the
- 9:33 – 9:54
Online gold is 10x better than gold
- MSMichael Seibel
other fun insight here is that like portable online gold is valuable. Like it is 10X better than gold. [laughs] And so as something you might wanna have, if you think gold is something that you might wanna own, and it seems like the market does like owning gold, portable online gold, strictly better.
- 9:54 – 11:08
Criticisms
- MSMichael Seibel
So I think out of maybe all three of these founders, Brian was exposed to the most shit takes. The most-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... people saying this was not gonna work. So break that down for us. Like explain all the reasons why Coinbase is not supposed to work and Brian should not be a successful founder today.
- DCDalton Caldwell
Well, at the time, um, people saw Bitcoin as a tiny market, that it was gonna crash, that it was a bubble. Um, investor didn't like it. It was synonymous with a lot of, you know, actual fraud, right? Didn't, didn't have a great reputation. Also, getting a bank deal was impossible. It's not like other founders didn't wanna start something like Coinbase. Uh, US-based exchanges were incredibly hard to start, and this is the reason why all the exchanges at the time were offshore, was, uh, the regulatory environments were, were different in different places, right? Um, a- another thing I wanna note is even Brian in his YC application didn't really believe in his own idea because what he basically applied to YC with was, um, the P2P transfer parts. It wasn't buying Bitcoin and holding it, it was the idea that he could build something like Pay- PayPal to do P2P transfers.
- MSMichael Seibel
Love it.
- DCDalton Caldwell
And that the, the buying Bitcoin part, but that was just part of it. And so isn't it funny that even
- 11:08 – 12:10
Undercounted
- DCDalton Caldwell
he kind of undercounted the-
- MSMichael Seibel
Yep
- DCDalton Caldwell
... the simple promise of buying Bitcoin in a non-sketchy way with a debit card in the US and not getting hacked and losing all your money. That was enou- that was enough of an insight to be the basis for a, like $100 billion company. He didn't need to do all this other stuff.
- MSMichael Seibel
But Dalton-
- DCDalton Caldwell
He didn't know that
- MSMichael Seibel
... to your point-
- DCDalton Caldwell
No one knew that
- MSMichael Seibel
... and, and, and following the pattern, a valuable insight that he learns after starting the company, right? Like you don't have to have all the valuable insights before you start. [laughs] Like-
- DCDalton Caldwell
Well, you remember what the Coinbase product was back in the day, right? It was a website. You logged in, y- you put in how much Bitcoin you wanted to buy, and you pushed a button, and you buy it, and that, that was, you could sell it too.
- MSMichael Seibel
That was it. [laughs]
- DCDalton Caldwell
There was no, there was no social network. There was no comment feed. You know, it was-
- MSMichael Seibel
There was no news. [laughs]
- DCDalton Caldwell
... probably the simplest products.
- MSMichael Seibel
No graphs. [laughs]
- DCDalton Caldwell
There were no graphs. [laughs] It was one of the simplest products I've ever seen.
- MSMichael Seibel
Yeah. So-
- DCDalton Caldwell
But it's 'cause it solved the right sim- single problem at the time
- MSMichael Seibel
And, and I
- 12:10 – 12:31
Impossible time raising money on demo day
- MSMichael Seibel
think that the way that this is kind of embodied was that, um, fully embodied how bad of an idea people thought this was is that he had a impossible time raising money on demo day. And so if he had taken the demo day signal, the investors' signal of, "Oh, we don't wanna give you money," and quit, we didn't have Coinbase.
- DCDalton Caldwell
Correct.
- MSMichael Seibel
All right.
- 12:31 – 12:39
Stripe
- MSMichael Seibel
Last one, Stripe. So, um, you had dabbled with payments, um, pre-Stripe.
- 12:39 – 14:14
Context
- MSMichael Seibel
How easy was it to accept credit cards online pre-Stripe? Tell-
- DCDalton Caldwell
Yeah. So I-
- MSMichael Seibel
Share the story with everyone. [laughs]
- DCDalton Caldwell
I have set up... Before Stripe existed, I set up, um, accepting credit cards for, for my companies twice. Once in 2002 or so, believe it or not, when I was very young, and then once again, um, in 2007. And to get a merchant credit card account, um, was like applying for a mortgage.
- MSMichael Seibel
Oh.
- DCDalton Caldwell
You had to fill out lots of paper.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
You had to fax in stuff. You had to personally guarantee things. They had to do fraud checks on you. It was rough. It was expensive. There was minimums. And it was, so it was a possible thing to do, but I would call it gnarly and the opposite of easy in every way, okay?
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
And so that was... So, and I also remember when Stripe came out, I was actually in the Stripe beta. I was one of the first 100 customers of Stripe way back in the day for my c- for my third company, the third time I wanted to accept credit cards. And, um, I really wanted it [laughs] in terms of make something people want.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
When it came out, and I read about it on Hacker News, I immediately wanted Stripe.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
And I hadn't even seen it yet. I just knew I wanted it.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
So that, that's the historical context.
- MSMichael Seibel
You know, it's funny. We were Authorize.net users, too, um, at Justin.tv and Twitch. And perfect example, again, of, like, a taste of the good stuff, but so hard to u- It took us three months to start accepting credit cards. I think there was a 30-page contract that we had-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... to read and figure out to sign, and it was like, "Wow." So once again, not first mover.
- 14:14 – 14:42
Peer problem
- MSMichael Seibel
I think another really interesting thing about Stripe was that it was a problem that they saw their peers in YC have. So literally, they were seeing all of their friends in YC not, like, going through all of the pain of Authorize.net, and they were hearing this story over and over again. And then, you know, that's a good hint for people out there looking for ideas. It's like, if all of your smart technical friends are complaining about the same thing, maybe [laughs] it's a real problem. Now,
- 14:42 – 15:19
Go-to-market
- MSMichael Seibel
last insight that I think that they had, talk to me about their go-to-market and specifically about understanding that their customers were developers and not business guys, 'cause I think that was revolutionary at the time.
- DCDalton Caldwell
Yeah. The, the really clever m- brand promise or marketing stance or whatever you wanna call it they had was to try to make the most beautiful website they could with the most beautiful documentation that was every, you know, programmer's dream. Like, they, they constantly asked themself and pushed themself to say, "What
- 15:19 – 16:38
What would a programmer want?
- DCDalton Caldwell
would I want?" Or, "What would a, what would a programmer want?" And this was so different than every other processing company because it was built for basically business people. Like, the customer was not the... The programmer who had to implement Authorize.net was not the customer.
- MSMichael Seibel
Right. [laughs]
- DCDalton Caldwell
It was like some- someone getting paid, you know, 20 bucks an hour or something to, to implement the code.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
Whereas this was like, they went nuts at making something that developers would just freak out about. And everyone copied it, by the way. Every developer would copy the Stripe documentation, copy the Stripe website. It was like the Apple. It was, it was like if Steve Jobs had to design a payments company, it would be Stripe. And I th-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... they totally did this on purpose, but what this created is a lot of buzz on Hacker News and around nerds basically that, "Hey, have you seen this Stripe thing?" "Oh, are you in the beta?" Also, they had did a beta invite program, and so there was a, it was a hot commodity to be able to get into Stripe and be able to use it. You were seen as well-connected if you got the-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... the pleasure of getting to use Stripe. It was like a favor they were doing you to let you use their product. That's how, that's how, that's what a great job they did in making the website and documentation excellent.
- MSMichael Seibel
What I love is that when the Stripe founders came to speak at YC, the other detail they added was it
- 16:38 – 16:58
Most expensive product
- MSMichael Seibel
was the most expensive product in the market. Like, to make sure people really wanted it, they didn't give it away for free. They didn't price it comparably. They made it more expensive, and people were still desperate to use it. Like, that's how you know you have an insight, like, when you're the most expensive thing, speaking of Apple, and people still are desperate for it. Now the shit
- 16:58 – 18:46
Criticisms
- MSMichael Seibel
takes, right? The shit takes were pretty clear. One, what are two teenagers doing in the banking space?
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
The reg- government regulation. It's the most regulated space in the fucking world, right?
- DCDalton Caldwell
Isn't this like a suicide mission? You're like, "Hi, we're 19."
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
"Um, we wanna start basically a bank. Give us all your money. Like, we're gonna, we're gonna, we're gonna handle hundreds of millions of dollars of everyone's money, so yeah, that's our plan."
- MSMichael Seibel
"And there will be no fraud."
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
"Like, we're, we're good." I think the second one is that even subtracting the regulation, they needed a bank deal. They needed Wells Fargo to let them start using their rails. What, like, as a s- as an early-stage startup, they need to get that, which at the time seemed impossible. And then of course, I think the last one is that, like, you know, PayPal existed. There was a really popular company where it felt like PayPal was, like, a quarter step away from this, right? And it was like, oh, even if you start doing well, PayPal can go here instantly. They have all these users. They're the hot company.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Oh.
- DCDalton Caldwell
It was seen as a crowded market with huge companies, with hundreds of employees, thousands of employees, and it's the classic thing, again, the knock against YC companies at the time is YC would just fund crappy versions of existing company. Like, the third-rate knockoff version of something actually good was what YC companies were. Isn't that hilarious? I don't know if people remember that, but that was the reputation of YC companies is like, "Oh, yeah, they'll take a existing idea that's good, and they'll make like a less popular version of it."
- MSMichael Seibel
Which, which kills me-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
... because, like, in all three of these cases, these folks had the problem, they had experience, and in hindsight, there was an obvious opportunity to make something 10X better, but most people thought they were idiots. And that's probably the overarching theme. They had
- 18:46 – 18:59
Contrarian
- MSMichael Seibel
to be contrarian to walk down this path because if they had asked 10 startup experts, 10 investors, 10 fellow founders, eight of them would have told them that they were stupid.
- DCDalton Caldwell
And-
- MSMichael Seibel
And like how much of that-
- 18:59 – 19:33
They had to build great good products
- DCDalton Caldwell
... they had to build good products. Like you can't-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... take for granted, you can't, we can't, you know, talk on a whiteboard and plan our strategy and win. All of these founders had to actually do it, and the doing it part was the hard part.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Right?
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Like, all-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... all these people had to execute and build a product that people loved and actually worked, and all these people built products that handled hundreds of millions of dollars, and they couldn't lose the money, right? So the actual execution bits, talk is cheap, execution's hard. Execution's expensive, and they ha- all these folks had to execute.
- MSMichael Seibel
So I think what
- 19:33 – 19:37
Takeaway
- MSMichael Seibel
the takeaway here is, if we can sum this up,
- 19:37 – 19:48
Incumbents
- MSMichael Seibel
one, you shouldn't give a shit if there's an existing product in the market. If you're a user of that product or your friends are users of that product, then they all hate it, and you should not give a shit. Um,
- 19:48 – 19:53
Don't care about experts
- MSMichael Seibel
two, you should not give a shit if most of the people around you who you
- 19:53 – 20:07
Market Research
- MSMichael Seibel
believe are experts don't think this is a good idea, especially you shouldn't care if they're not gonna be users, if they have no experience with the pain of using the existing product. And then
- 20:07 – 20:56
Market math
- MSMichael Seibel
three, be very careful about your initial market math. Be very careful about pretending that you know how big the market could be. It turns out with so many of these transformational technologies, there are use cases you can't dream of, that once you build a 10X better product, other people will do. And so each and every time these founders were presenting, "Oh, we have a market size of blank," the next time they raised money, they could say, "Actually, we made a mistake. The market size [laughs] is actually bigger. We didn't think of this. We didn't think of that." And so don't be discouraged if someone's like, "That's a tiny market." That- that's kind of a, a bullshit, um, thing. That would have killed all these companies. All right. Talk to you later, man. [outro music]
Episode duration: 20:56
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