Archive for the ‘ The Matching Game ’ Category


Got inspired last week. Between a discussion with a friend at Pivotal Labs and observing people on The Matching Game I decided to build a new site:

It’s just for fun, inspired by the viral success of and the fact that people on The Matching Game like to talk about their personality traits. I figured why not create a site where you can see how your friends would describe you. Maybe even turn it in to a dating site where you can see how someone’s friends would describe them.

We’ll see…

Check it out and create your own page:

Investing with Purpose

Ok, so Irrational Design was featured in the NYT because of our (now my) passion for avoiding investment.

Over the past few weeks I have started to explore the idea of taking investment for a few reasons:

  1. I’m worried about my personal finances as I try to get these businesses off the ground
  2. I’ve been introduced to a few investors that are amenable to deal structures that will not hurt the long-term risk taking / “do crazy shit” ability of the company (e.g. no board seats)
  3. The Matching Game is at a point where an injection of capital would be put to immediate and good use, providing a clear and effective return on their investment (or at least the numbers seem to suggest that).

Despite all of that I’m still hesitant about taking capital. A few things still nag at me. One thing:

Why don’t any investors ever ask me about why I’m building this? What’s the purpose of all of it?

They ask about the idea, the numbers, the team, the technology, etc, but they don’t ask why?

Why do the vast majority of investors view companies simply as a vehicle for profit? Most of them spend their own time and money supporting non-profit work, giving back to the community, etc, but they very rarely ask “How can what your building really move the dial, change the world, or even just change the community, or even just one person’s life?”.

How is your company going to make a difference beyond just making money?

Here’s the deal, and I structure my thinking around this more and more:

I want to spend my time doing things that can’t fail.

TheMatchingGame may fail financially, but in the meantime I’ve helped thousands of people meet someone, maybe meet someone who will be with them for the rest of their life. That may not sound like non-profit work to you, but it’s some of the most meaningful work I can think of. For a lot of people companionship can help empower them to do more good themselves, which is a huge multiplier effect.

SecretGoals may fail financially, but in the meantime it’s giving people a place to discuss, vent, brag, etc. about the most important goals in their life, free from judgement. It’s actually pretty close to a lot of the work non-profits do. If I can get it to a profitable state where it’s self-sustaining, how awesome is that? If I can’t, then well at least I affected people’s lives for the better along the way.

Why don’t more investors think like that? Why aren’t they saying to themselves, “Here’s 10 grand. Even if I never get a return on my money I’ll be happy spending 10 grand with you because I like what you’re doing and, even if you fail, that 10 grand will be put to good use along the way.”?

Sounds cheesy, I know, but it’s also common sense. Why not have an investment that can’t fail?

Why does doing good and making money have to be separated out? Why can’t we try to build companies that are capable of doing more and more good because they’re making more and more money? Why can’t we look to reward our employees with good pay while at the same time rewarding them by giving them time and resources to give back to the community?

If I can get Irrational Design profitable enough I want to explore starting a school (I already have a lot of ideas around it).

How many investors would balk at that?


And yet something like that would be putting capital to good use in the community, would make people look at your company and want to support it, would probably garner a lot of press and great attention, and would make your employees feel like they’re part of something truly special. It could end up making the company far more successful in the long run.

And yet I doubt there’s too many investors who would support, let alone encourage something like that.

Investors: you’re already rich, why aren’t you supporting more crazy shit?

New York Times Article

I guess it is possible to get some press with out raising venture capital:

New York Times Irrational Design Case Study

Interesting to see how all of the experts disagree with us:)

Going With Free

Make it free for people to connect and message each other on The Matching Game.

Why Not?

Well, for one, it’s the only revenue coming out of the site right now.

Plenty of sites have proven that a subscription model works with online dating. People are willing to pay a monthly fee to join an online dating community. If we go down this road and start offering it for free, it may be difficult to reverse the decision.


For one, we’re not making much money off the subscriptions yet (maybe $50 a month). We’ve become popular with a slightly younger crowd (18-25) and they may be a little less likely to pay. Either way, we’re not throwing away much revenue.

Since not that many people are paying, not that many people are connecting and meeting people through the site either. It frankly sucks to know that you have two people who may really enjoy meeting each other, but they’re not because you’re asking for a fee. Of course if they were serious about meeting each other they would probably just pay the fee, but given where we are at with the site, it seems better to lower any friction points and get as many people meeting through the site as possible.

How’s It Going?

We opened it up about a week ago and, not surprisingly, a lot of people are connecting and messaging now. Now we just need to figure out a way to monetize the site. So far in a few limited experiments advertising has not worked that well, so we may need to get creative.

The Right Adhesive

When we tell people we’re building 4 products simultaneously, none of which are close to being finished, the immediate assumption is that we’re trying to throw products against the wall to see what sticks.

This isn’t the case.

It is unlikely that we will ever shut down any of our products.

We’re simply trying to figure out what the right formula is for making each product stick. And we don’t want the products to be too heavy and bloated until we’ve found that perfect minimum product that does stick.

We believe in the story and the value of each product. Getting it to stick and grow and achieve the critical mass necessary to make the product truly valuable is a different story, though. That is why we are focusing on the fundamentals of each product, the minimum viable feature set, to make sure we’ve got that right before expanding on it.

Already with we went too far and are considering doing either a massive re-factoring or possibly even completely rebuilding it to simplify it down to that minimum set of features that are the foundation for the overall experience. As it is, all of the features we built that we thought we needed are making it harder for us to push forward now that we have better perspective on what is important.

Of course if we try for years and can’t get something to stick we may think about shutting it down, but we’ve been careful to choose products that require minimum maintenance and can run cheaply, so we can simply let a product run. This allows us to both to think about the product (maybe a brilliant idea comes to us in 6 months about how to make it click) or simply give it a longer time to hit the necessary inflection point where the size of the community makes the product valuable enough to stick.

Embarassing Launch

We’ve just launched and it’s far from complete. I think we would even consider it somewhat embarrassing.

Secret Goals

Why Not?

Well it’s embarrassing for one. People who use the product right now are probably going to be disappointed. There isn’t that much functionality, the functionality that is there is half-complete, and we’re not yet satisfied with the design and user flows. If we do get anyone to register we’ll probably lose them rather quickly just because there’s not much to do on the site yet.


We’re trying to push ourselves to validate our assumptions early on. We can launch early, use to see what people are doing on the site, and make better decisions about what to prioritize, hopefully allowing us to get to the right product a lot faster.

It’s hard to look past the embarrassment, but we need to be efficient. We need to figure out what people are engaged by on the site and where people are getting confused. We learned from our efforts on that we can’t rely on our own assumptions without frequently validating our ideas. We spent way too much time on building features that were complex and made the site more complicated, but had little impact on the way people used the site. Had we been more incremental in our approach and less afraid of embarrassment we probably could have saved ourselves a month of work.

How’s It Going?

We’ve just launched it and ran our first test. Already we’ve identified one page on the site (the page for a new goal that no one has take on yet) that is just killing everyone’s experience. Right now it just looks like a registration page, which may be suggesting to people that you have to register in order to do anything on the site.

We’re going to focus on changing that page now and then run another test. We’ll let you know how it goes.

A New Product

We’re considering building a new product. It would be our fourth product following,, and

Why Not?

Well for one, we already have three products, and all of them could use some attention. We’re also nervous that we’re simply doing this because it’s shiny and new and has infinite potential. It’s always easier to imagine a non-existent product becoming a hit than a product that has a track record deviating from that track much. We don’t want to be guilty of getting distracted too easily when we have products that are showing solid results that we can build on.


We feel that one more product can help round out what we are working on effectively. We also want to explore a site that is built around community with the potential to monetize through advertising, unlike our other sites, none of which have advertising on them. We know that it’s not easy to build a business off of advertising alone, but advertising is a very established and effective way of generating revenue and right now that is what we need, even if it’s not a huge revenue stream, it would go a long way to helping us keep the doors open long enough to make sure the other products have a chance to get going as well.

We are also thinking about an idea that may be an effective story in the press, helping us to get the word out about it, and may help a lot of people improve their lives, which we feel really good about.

How’s It Going?

We’re still debating it, but I’m pretty sure we’ll be building it soon. Will have some more info about the product once we’ve fleshed it out a bit more and can describe it effectively. Hopefully soon.


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