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Why we dropped out of Yale to start a dating website (blog.thislooksfun.com) similar stories update story
70 points by CJM13 | karma 100 | avg karma 6.25 2011-11-02 13:27:03 | hide | past | favorite | 85 comments



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I couldn't find a way to comment on the blog post or a way to contact the author:

"Diving into online dating - it’s not a zero sum game

Online dating is hear to stay,"

typo, should be "here to stay"


Fixed! Thanks! You can email us at Chris@thislooksfun.com or Greg@thislooksfun.com

>“Current dating sites suck … an undergrad could build something better as a class project.” ~Paul Graham from his essay, How To Start a Startup

>we decided to take PG’s advice a bit further and take time off of school.

A lot has changed in the online dating world. Hopefully they have a better argument than a 6 year old quote from one person, albeit being from PG.


We've recognized some of the changes that have occurred, but think we can change it even more. Thanks for the feedback!

Let us know how that name box is converting compared to without. Are you A/B ing it?

Yes, we've tested them out, this one converts the best.

I imagine that "dating sites suck" is a way of saying "it's really hard to make a dating site that works for people." Sure, lots has changed in the dating world, but I would not be surprised if there is substantial room for improvement for a long time to come.

There is definitely room for a ton of innovation and improvement in the online dating industry. Online dating isn't going anywhere and will continue to grow. Social networks and dating sites can be a great way to meet new people. We want to limit the online interaction and have people share an offline experience together as soon as possible. The artificial contact that current online dating platforms provide cannot replace the interpersonal connection that happens in the real life.

I think OKCupid pretty much nails online dating. I even mulled a dating project myself but they'd be hard to beat.

Were you guys onstage for Office Hours at Startup School?

No, that wasn't us, just proves that this is an exciting time for this industry

Good luck!

Be sure to get a fantastic front-end engineer/designer on board. It strikes me the online dating space more needs better design than algorithms. (even OKcupid is just OK. pun intended)

wishing you guys all the best - but you've probably picked one of the most difficult business models imaginable. building a user base for a dating site is even harder than building a new social network and competing against giants like match.com is gonna be very difficult. my advice; try to appeal to a niche segment - don't target the masses. as far as I can tell online dating sites aren't broken, it's in most cases just a lemons market.

Thanks for the comment/advice!

I had this exact same idea about 8 months ago - connecting singles around events. I was a little more focused on bringing local businesses into the mix to promote the events though. I thought through it quite and bit and my conclusion was that it doesn't really differ much from a singles night.

An app that made facilitating a singles night easier is a pretty solid idea, however, selling it as a dating website is not the right way to go in my opinion.

The main demographic for dating websites has always been men. The problem with trying to put together a singles night is that the main value proposition (women) is difficult to come by with an online dating website.

Additionally, a lot of people who try dating websites are there for a few main reasons: 1) they are too busy to go out and meet people 2) they are too shy to go out to meet people. Either way, this solution doesn't solve those problems.

I actually built out a good portion of the backend of this product but have since pivoted into something different. They also will run into the chicken and egg issue, although with a little facebook marketing that's pretty easy to solve.


We appreciate the feedback! Like every dating site we will have to address the chicken and egg problem of getting a solid user base (particularly women). However we are working on some clever ways to attract women to the site. More specifically we are developing a matchmaking component which will allow users to pick out dates for their friends and decide not only who their friend goes out with but also what they do.

Thanks for the comment!


Free cupcakes for the fairer sex that sign up. Chicks love cupcakes.

Is it true that there is a dearth of women in online dating sites in general? If so, where did you see that info? Or is that an assumption you're working from based on the gender ratio in bars/clubs?

How is this really different than HowAboutWe?

We differ from HowAboutWe in that we're going to offer prearranged events for our users. We want them to avoid decision paralysis when picking a date or date idea, so we give them something fun, tested, and popular to try while meeting someone new who wants to do the same thing.

Their site http://thislooksfun.com/ is currently unimpressive. It's noticeably slow on my broadband connection. Why? Huge background images changing on a relatively quick timer (sizes as large as 4.5mb, 7.56mb).

It's just an email gathering page, but a few minutes spent in an image editing program would give a much better first impression.


Might just be my device, but the site crashed my iPhone twice just trying to load.

You dont need an image editing program, just imagemagick:

> convert a.jpg -strip -quality 60 a.jpg


The images need cropping/resizing, but yes, imagemagick could do it.

My suitemates and I (BR '14) were talking about what it would be like to drop out of Yale. We realized that the school would pretty much take you back whenever as long as you were doing something cool in the spare time. That's a really nice "psuedo-assurance" to have imo.

Best of luck fellas!


Thanks! Would love to connect if you're interested in knowing more. Shoot us an email!

Yeah, Yale makes this sort of thing a LOT easier than many schools thanks to how generous its leave policy is.

The math would be a lot different for a school where dropping out meant losing your seat entirely.


I have to disagree on this one -- Yale's policy actually really sucks. I am currently taking time off, and was told that not only must I take course credits from an outside school to get readmitted from a personal withdrawal, but also have to go through an abridged re-application process. A lot of time commitments and question marks there.

I think it'd be smarter to put groups of people together and send them to events or create events for it. So long as the ratios are even, or could be set. The advantage of groups is that it's not a make or break situation, like a 1-on-1. And groups of friends can be matched with other groups of friends.

dating is really a niche that's more or less guaranteed slow growth, taking time off from school to pursue something this generic doesn't strike me as smart...since you'll spend a ton of time waiting for your user numbers to climb.

That's a bit of a fallacy to assume that more time = more users.

User growth doesn't happen by itself because you have a product out (outside of the rare viral hit).

It takes months of hard work and focus to build a user base.


months of hard work that should be spent hitting the books, learning something about the world and gaining the experience required in order to properly provide a solution for educated and experienced people over the age of thirty who can spot an immature product with their laptop closed.

I'm not saying there isn't a market for lbs dating sites, what I am saying that from what I'm reading it appears that a couple of intelligent people are dropping out of school at a young age to pursue what amounts to some low-hanging fruit.


Low-hanging fruit would be a good thing to pursue. Did you mean the opposite?

That's insane. Who told you that?

We decided to take time off from school because we wanted to fully commit to whatever idea we pursued. We realized that we could not create something meaningful in our spare time. It has already been a tremendous learning experience and we don't regret our decision.

"Current dating sites are not the last word. Better ones will appear. But anyone who wants to start a dating startup has to answer two questions: in addition to the usual question about how you're going to approach dating differently, you have to answer the even more important question of how to overcome the huge chicken and egg problem every dating site faces. A site like Reddit is interesting when there are only 20 users. But no one wants to use a dating site with only 20 users—which of course becomes a self-perpetuating problem. So if you want to do a dating startup, don't focus on the novel take on dating that you're going to offer. That's the easy half. Focus on novel ways to get around the chicken and egg problem."

From http://ycombinator.com/ideas.html


Dating sites don't inherently suck.

OKCupid is actually an amazing website. The problem, as always, is there will always, always be more men seeking women.

I'd like to see what would happen if a dating site somehow tried to keep the ratio of men to women more appealing to both sexes.


there's likely a deeply rooted social and demographical reason for the skewed ratio, which is probably impossible to change. in the western society women till age 30 are usually the ones who choose their partner and not men - hence there's less of a need to join a dating site. interestingly this switches somewhere around 35-40, after which men are in a better position (ironically in part because men have a shorter life expectancy).

> The problem, as always, is there will always, always be more men seeking women.

i don't think this is the case, exactly. after talking to people about it, the issue seems to be that men are just more aggressive about it, which turns away a significant segment of women. the women are out there, some just don't like putting up with the crap they get on dating sites.


the issue seems to be that men are just more aggressive about it

If that's the case, then it would be interesting if a site like OKCupid had a limit on the number of emails per day a straight guy could send to a straight woman. Say, only one every few days. That would require male users to think very carefully about who they email.

It's an arbitrary thing, but it would be interesting to see how the dynamic changes.


agreed. i've always thought that an interesting idea to try would be to create a (mostly) zero sum dating system where you have to respond to people in order to initiate conversations with others.

it de-incentivizes sending rapid-fire copy/pasted messages as well as completely ignoring messages. levels things out a bit.


That kind of reminds me of Slashdot's Karma system. I think it would work, I think the concept would have to be weighted towards dating, but not 100% a dating site. Something that's as much about being social as it is finding a partner. So maybe encourage people to email people they find interested on a "just-friends" basis.

Maybe instead of marking your profile with your intentions, you mark each individual email, ie, "New Friends", "Short-Term Dating", "Activity Partner".

I'm just spitballing here.


I suspect the effect of this is that the most attractive 10% of female users would get an even higher percentage of all male-to-female messages.

Maybe at first, but wouldn't that fix itself over time as the less attractive men realized that they were getting no responses?

I was under the impression that the gender disparity was actually age dependent: A surplus of both young men and older women.

Good luck guys...don't let all the negative comments get you down. Power through and stay on task.

Thanks. We really think that you have to be an unflinching optimist to be an entrepreneur!

Developing this space as a college undergrad means you should be able to do some things really well. Event planning, for one, seems like something people in their mid or early-twenties could disrupt. It'll be interesting to see how your perspective translates to older users. Especially because you can't dogfood a dating site (even OkCupid's founders never used it).

Good luck!


Thanks for the comment! We're gathering a lot of different events that cover a variety of interests, so we're hoping that we will have something to offer for everyone.

guys - your "tweet this" link is broken. Once I sign up thro the pop up, it goes to a dead page. Look fw to it though.

Do you know about the Yale Entrepreneurship Institute's incubator program. Just do the summer incubation program, and see what happens. Dropping out is risky.

Hi, just signed up to try your website.

2 comments: 1) the text box does not display underscore (_). A lot of emails contains _ character, so it could confuse ppl.

2) You should implement a 404 page. instead of the current error page when you go to thislooksgood.com/[xx]


...teach ourselves how to code

How are you guys going about doing this?


Friends of ours started an open lecture/workshop series called HackYale. Besides that there are a ton of great resources on the web. My best advice would be to just start building something and practicing a lot. Tutorials and classes are a great place to start but there is no substitute for actually starting a project from scratch and figuring things out as you go along.

Let me know if you have any more questions!


Thanks for responding, I ask because I'm currently mentoring a friend who's trying to learn and I'm curious to see what works for others. When I was learning programming I did more or less the same thing, but also found choosing the right technical books to be instrumental.

What books do you recommend in particular?

Thanks


- take out 'revolutionizing' verbiage - describe benefits in a few sentences - offer something concrete for signup - address page load issues

Just some feedback: I didn't see an easy link to your main page on the blog (not in the header, sidebar, or footer). There were plenty in the body text, but I didn't look there first for a link.

In signing up, I also had to re-enter my email address after the first username I tried was taken. You could repopulate the email address field based on the prior submission in the event that a username is unavailable.

As others have said, the background images on the splash page are huge. Even on my 15Mb connection I had to wait a moment for them to load.


I tried to think of some constructive criticism (since that's more useful than "good luck guys!"), but couldn't really figure anything really penetrating, but here's my best shot at some question to think about, constructive criticism, etc.

1) how is this different than people just going out to events with friends and then randomly meeting friends of friends to date? My best guess is that this is different because there's more of a recognition that people are looking. How does this change the dynamics?

2) My guess is that this is going to be kind of a platform for matchmakers too. What, if anything, do they get out of it?

3) Will the businesses hosting/benefiting from the event pay a cut of their proceeds to TLF?

4) Will people who meet on the site attend the events as pairs? Or will it be like a singles event? If the latter, then we'll see an "alpha male" problem where a handful of males will be desired. The betas will drop out and more importantly many women will be turned off by the competition for a few men.

5) Finally, and most importantly, any play in the dating space is most likely not going to be a tech play (that's been done - OKCupid and eHarmony among many others have all sorts of fancy algorithms). Like most social media today, the business model will stand or fall based on very nuanced understanding of human nature, in particular very nuanced understanding of male/female romantic and sexual interactions.

Now, no offense, but when I think of "very nuanced understanding of male/female romantic and sexual interactions" the image of two college guys who read HN does not come to mind. Nothing personal, I would apply the same reasoning to myself (which is one of the reasons I have not started a dating site). It's just something to be aware of, you're stepping into an area that is one of the most misunderstand social arenas for our species.

All of the above are just my musings intended to plant some seeds in your head. I think this is a great idea and you should go for it with gusto.

The only real advice I have: If you don't already have one, get a woman on your team. Gone are the days where dating sites are just tech/algorithm plays, like I said above you've got to understand the psychology and there's just no way to do that with 50% of your target market missing from your founding team.


Thanks a lot, certainly more helpful than a best of luck wish.

1) What we're doing really isn't any different at all than people just going to events with friends and then meeting potential friends to date. We want to replicate the way dating works in the real world online. So we are providing an online platform to generate more of these interactions. There is certainly the recognition that people are looking for dates so that changes things a bit.

2)Users will be able to search for dates for themselves or set their friends up on dates as a matchmaker. We're coming up with ways to incentivize the matchmakers but for the meantime are hoping users will find the experience of matchmaking fun. There is concern that the matchmaker will be put in an awkward situation if the date does not go well for their friend, but that really isn't any different than setting someone up offline.

3)There is no cost to businesses to use TLF. We help businesses solve the "butts in seats" problem so they are happy to work with us to arrange a deal that allows us to have users prepay for their dates.

4)We are starting with singles events.

5)We completely agree. Our focus is on the offline interaction between users. Our site will only serve as a means for quickly setting up a shared experience offline.

We are actively looking for a woman to bring on board! When developing the concept we gathered feedback from as many of our girlfriends as we could.

P.S. Although we may be two college guys who read HN we'd like to think we have a decent understanding of the fairer sex.

Thanks again!


This should not be [dead]:

CJM13 11 minutes ago

Thanks a lot, certainly more helpful than a best of luck wish.

1) What we're doing really isn't any different at all than people just going to events with friends and then meeting potential friends to date. We want to replicate the way dating works in the real world online. So we are providing an online platform to generate more of these interactions. There is certainly the recognition that people are looking for dates so that changes things a bit.

2)Users will be able to search for dates for themselves or set their friends up on dates as a matchmaker. We're coming up with ways to incentivize the matchmakers but for the meantime are hoping users will find the experience of matchmaking fun. There is concern that the matchmaker will be put in an awkward situation if the date does not go well for their friend, but that really isn't any different than setting someone up offline.

3)There is no cost to businesses to use TLF. We help businesses solve the "butts in seats" problem so they are happy to work with us to arrange a deal that allows us to have users prepay for their dates.

4)We are starting with singles events.

5)We completely agree. Our focus is on the offline interaction between users. Our site will only serve as a means for quickly setting up a shared experience offline. We are actively looking for a woman to bring on board! When developing the concept we gathered feedback from as many of our girlfriends as we could.

P.S. Although we may be two college guys who read HN we'd like to think we have a decent understanding of the fairer sex.

Thanks again!


"... We want to replicate the way dating works in the real world online. ..."

Isn't the real world process broken? Are you taking into account "Gutentag Secord theory?" [0]

"... the non-committers are out there in growing force. If dating and mating is in fact a marketplace—and of course it is—today we’re contending with a new “dating gap,” where marriage-minded women are increasingly confronted with either deadbeats or players. ..." [1]

Are you trying to solve this problem?

[0] Marcia Guttentag, Paul F.Secord ~ http://www.amazon.com/Too-Many-Women-Ratio-Question/dp/08039...

[1] Atlantic, Kate Bolick, "All the Single Ladies" ~ http://www.theatlantic.com/magazine/archive/2011/11/all-the-...


>we'll see an "alpha male" problem where a handful of males will be desired. The betas will drop out and more importantly many women will be turned off by the competition for a few men.

I've never heard of this "alpha male problem"; I've only heard stories of there being too few women. Could any frequenter of singles events elaborate on this?


I can't speak to the alpha male problem in the online dating market, but lots of people writing about sexual dynamics and marketplaces have noticed it (see, for a popular account, Neil Strauss's The Game; in academic land, The Evolutionary Biology of Human Female Sexuality doesn't use the term "alpha male" but describes how many women frequently glom onto a subset of males and pursue them).

Think about it this way: there were probably a handful of guys at your high school or college (probably athletes, although they might've just been unusually social or skilled in some other field) who women disproportionately sought. Most of us have seen this on some level. They're the alpha males and that, in a nutshell, is the alpha male problem.


There were also a handful of women at my high school and again at my college who men disproportionately sought. I'm not sure I see that this is a one-way issue.

Here's an idea:

The current problem with dating sites is poor response rates from women.

Many sites have tried to solve it by scoring candidates and only letting you see candidates that meet criteria---i.e. reduce messages sent, and boost chances of being a match.

Why don't we instead treat it like a SPAM problem. Only show people the type of messages that they've responded to in the past. Don't necessarily believe what they say about what they like, trust their revealed preference.


Or why not create a dating site which only allows women to contact men?

By creating a one-way dating channel, you can filter out a lot of the behavior which drives women away from sites. Make it a virtual Sadie Hawkins dance.


Would this really be ideal though?

Most women (not all) want be pursued by men.


FYI, this has been done: http://www.herway.com/. No idea how successful it has been.

Stay in school.. I can't imagine why you guys are dropping out of school to "start a dating website". That said, good luck and I'm sure will learn a lot.

Agreed. I love your excitement and energy, but there's no reason you can't explore this idea while at Yale, or during a summer break. When you do a startup, you should look at the worst case scenario - you may regret falling behind in studies. The odds are you're going to fail, and things take much longer than planned - are you okay with that? Oh, and if you want to raise money any time soon, you may want to think about a different market. I don't want to be a downer, but I think it's important that the startup fantasy be balanced with reality. Good luck!

I agree. I went to Yale and wouldn't trade those semesters for anything. You've got your whole life to start a company, but the opportunities you get to build yourself at a place like Yale don't often come up again.

And especially for another dating site -- this is a market that many smart people have spent a lot of time thinking about, and unless you have something truly revolutionary which is hard to replicate, the odds seem stacked against you.

But again, best of luck. And think about using Yale resources as well like YES, your summers, etc.


Facebook was the ultimate online dating site, until they removed/restricted the search-within-network feature.

reminds me of http://chirpme.com/

When you read about most founders who dropped out, they already had significant traction before making the leap. In my honest opinion you shouldn't drop out of college until you have a finished product(even if it's only a MVP) with traction and can show that this is a better alternative. Obviously you're free to do whatever you want but from an impartial observers perspective, this move seems unecessarily risky until you have a finished product, and enough users to prove it's viability.

The title is alarming: "Why we dropped out of Yale to start a dating website"

But the first paragraph is less concerning: "... taking time off from school to build and grow our company"

Yale is generous in terms of granting leaves of absence, so the knowledge that you're not actually dropping out really changes my view of your decision (for the better). You'd be crazy to drop out of Yale for an idea with no traction. To take a semester, or possibly a year, for the same? That's a much less drastic proposition.


We are very fortunate that Yale makes the process of taking time off so easy. I emailed my Dean the day before registration and didn't need to do anything else. We do plan on going back and graduating.

So this article post was libkbait. Gotcha.

College is one of the best times of your lives. Don't drop out, I'm glad you're only taking leave. Work will be waiting for you when you're done, I promise.

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