My first startup failed because I had no idea what I was doing. I started an online vacation rental site, similar to vacationrentals.com vrbo, homeaway etc... I was getting traction and had people list their rentals on my site but I failed to collect any revenue. The thought was, build it, offer it for free to grow it and then charge. Well, I built it (wasting way too much money on an original solution when existing solutions could have done just fine), people came (after I bent over backwards trying to onboard them), but time sucked me dry and I was not able to sustain the "business" any longer. Looking back, I did just about everything wrong.
>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.
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).
