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>The thought was, build it, offer it for free to grow it and then charge.

I feel like this is an incredibly common software developer turned entrepreneur mistake. Lack of confidence in asking for money leads to a reluctance to put a price tag on the thing you have built.

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With vacation rentals, you have to have people who actually rent stuff and that's the part of the chicken/egg problem I haven't solved yet. While I was able to bootstrap the site, the traffic to it was non-existent thus I felt guilty if I charged people to list. The premise was that they would list for free first, their listings would attract traffic, then I would charge people to list. Meanwhile people are booking and more are listing - that was the idea.

The simple way out of that conundrum is to make it free to list (perhaps with an option to upgrade to a "premium" listing for a recurring fee), and charge for the actual bookings made through your site (you'd need to experiment to figure out whether flat fees or a percentage worked better for you).

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