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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

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.

morcutt 8y ago
How long ago was this? Was it a specific region or all over? Did you try to raise funding or it was all bootstrapped?
- woogiewonka 8y ago
  This was about 7 years ago. It was bootstrapped. The site targeted US / US-based vacation destinations (Caribbean, Jamaica etc, not entire world).
pandapower2 8y ago
>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.
- woogiewonka 8y ago
  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.
  - webmaven 8y ago
    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).

morcutt 8y ago

How long ago was this? Was it a specific region or all over? Did you try to raise funding or it was all bootstrapped?

woogiewonka 8y ago
This was about 7 years ago. It was bootstrapped. The site targeted US / US-based vacation destinations (Caribbean, Jamaica etc, not entire world).

pandapower2 8y ago

>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.

woogiewonka 8y ago
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.
- webmaven 8y ago
  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).