The most important thing is to get WOMEN onto the site first, and mostly attractive women. A dating site is similar to a bar or club. Where attractive women go,

The most important thing is to get WOMEN onto the site first, and mostly attractive women. A dating site is similar to a bar or club. Where attractive women go, men follow. Do you think you are going to get a lot of male signups if there's nothing but unattractive women on your site? How do you use $50k to get attractive women, who can easily get dates in real life, onto your dating site? Offer them something they find valuable, but most importantly, wouldn't be embarrassing for them if their friends found out. What might that be? What about a charity auction? Men bid on women's profiles and the highest bidder gets to take the woman on a date. 90 % of that money goes to charity (10 % to you, the owner of the site). Women can choose to either make their bid amounts public or private. They can also choose a charity of their choice. Women don't have to be embarrassed about doing something for charity - in fact, they might drag their friends along for kicks (and among some groups of women - to see who can get the highest bid). They also get to go on dates with generous and/or wealthy men. Valuable + not embarrassing. To set this up, start in NY. Throw events with the $50k where women get to set up profiles online and men bid on them, preferably with influencer type groups. You can offer the reverse as well, so it's not sexist (although that sort of controversy mixed with charity gets you a lot of press) and because some women would delight in bidding on men. Later, you can expand bidding to include other, non-monetary things: home cooked meal by professional sushi chef, help with moving, etc. So the less wealthy men can too have a chance at wooing the women of their dreams.