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Stop me from doing something stupid


Cheer up dude :slight_smile:

I do agree dating sites are mostly made from the perspective of men though.


There’s 2 problems with the dating agency idea where the end-goal is finding a life-partner:

  1. It’s a 2-sided marketplace (generally recognised as a Really Hard Business Model)

  2. When you achieve Customer Success, your revenue stops (usually you’d expect more money at this point)

Not saying you shouldn’t do it, but those are the 2 problems I think you need to think about really seriously


P.S. If you haven’t listened to Series 2 of the “Startup” podcast, it would be worth a listen; the company they follow is a dating agency.


First, yes, a marketplace is really tough to approach as a bootstrapper. And, not especially appealing for investors.

As a personal example, with https://MastermindJam.com I effectively run a dating site.

For polygamists.


Let me explain.

I set four strangers up on what amounts to a blind date into a peer-driven business mastermind group.

Much like eHarmony, I use around 30 points of data to make the best possible match that can be made with the candidates on hand.

Thus, the network effect, marketplace problem. These matching algorithms work fantastic when you’re dealing with a large number of signups, but everything falls apart with a slow traffic month.

I might say that MastermindJam has a problem that’s even more onerous than the one facing a dating site that matches people 1:1. I’m matching 4 people into groups. If one of these groups has a jerk in the mix, then the other three members walk away feeling they didn’t get their money’s worth and have a negative opinion of the service—for something that I have no control over.

(Because there’s just no good way to ask people in a questionnaire if they’re an asshat or not. Trust me, I’ve tried.)

So yeah, I can attest that bootstrapping a marketplace (or any business relying on network effect or matching humans with one another) is really, really difficult.

On to Rachel’s second point…

[quote=“rwillmer, post:22, topic:3944”]2) When you achieve Customer Success, your revenue stops (usually you’d expect more money at this point)

I don’t agree. I mean, yeah, this does happen, but it doesn’t have to happen.

A great counterexample of Rachel’s assertion would be the wedding-centric website https://www.theknot.com

The Knot helps you plan literally every aspect of your wedding. Seating charts, picking out groomsman outfits, invitations… everything!

And you’d think they lose a customer at the passing of every wedding date.

But not so.

After your wedding date, a clever sequence transitions you to their other properties:

The Nest https://www.thenest.com helps the newlyweds build a happy life together with advice, content, products, and services on housing, furnishings, cooking, budgeting, pets, and travel.

The Bump http://www.thebump.com Yes, you guessed it. After you’re married, you’ve got the perfect home and personal life, many of The Knot customers will find baby advice useful at The Bump where they provide products and content around getting pregnant, fertility, pregnancy, newborns, infants, toddlers, kids, schooling, fashion and parenting.

Clearly, The Knot sees their customer differently. If they earned your trust in helping to plan a wedding, you’re pretty likely to trust them in many of these other areas, too.

I think more dating sites should take that approach, frankly, but it requires a long-term vision most don’t care for.

With a dating site, you could easily emulate the existing dating sites like OkCupid, and then after a successful match start offering services, content, and products to move them to engagement products, wedding products (divorce products :wink: ), and so forth.

But first, you have to have the guts and the strategy for solving the marketplace conundrum.

I’d love to hear more fresh ideas on how to defeat the marketplace dragon inherent in these matching services, personally. Is it absolutely a requirement to have a warchest of cash to throw at marketing, or are there other ways short of taking out a Super Bowl ad?


Hi Serge,

I am on board with your thinking.

Yes there’s a lot of competition and yes it’s a market place that only works when you have a critical mass of people using it but boy oh boy if you could create something that worked significantly better than the existing sites and you got that critical mass you would have a monster on your hands.

Some thoughts :

  • Does it have to explicitly be a dating site ? In real life checking out potential romantic interests usually happen in a group context with no explicit acknowledgement that that’s what’s happening. Could the site superficially come across as something else providing plausible deniability even if everyone knows what the deal is.

  • In order to get started could you target a specific geographic location and a specific segment of people who have particular selection criteria. I think some research and thought could come up with an under served group but the first ones that come to mind are already being served eg. vegetarians, specific religious, political and philosophical groups.

  • Is there a way to make it more group oriented, so you don’t match couples you match dinner groups and people can join as a group. So a woman and her 2 friends can join and be matched with 2 guys and they all go to dinner. Safety is an issue for women in way that we men don’t understand. Making it a group activity where a woman brings her friends might be significant.

  • I think older women are an interesting market for dating sites. I’m 37 but I know 5 women between 50-65 who are looking for a man. A technology that really engages them might look quite different to what dating sites currently look like.

  • More and more older people are playing games on their phones and computers. Could it be a role playing game that extends out into real life meet ups and dating. What about letting users create a parallel fake/fantasy profile to go along with their real profile, people communicate much more freely when ‘playing a chracter’. One of the over 50 women I know who is looking plays Clash of Clans on her phone. If there was some game that also gave her the chance of getting a date I think she would try it.

I think there are some deep psychological insights about human mating that could allow great innovation here, not sure exactly what they are though :slight_smile:



You are probably right. There was an interesting article on BBC recently about a woman starting a lesbian dating app. It’s interesting because it sheds some light on the female perspective and it contains some bootstrapping stuff on getting a dating app off the ground. Here it is:


There are already apps trying to make it easier for older people to find companions. One example is http://www.stitch.net/ that received over $1 million in funding (they’re at the co-working space I work from). I’m not saying it can’t be done as a bootstrapped business but you really need to find something that everyone wants and that only you do. Also, unless you have a lot of friends looking for someone I think you’re going to struggle to create a market.


Well that’s that sorted then.

If Buggy is against it it’s a sure thing that someone will make over a billion from it in the next 18 months.