Mitchella

"If he didn't like it he could send it back and not be charged for that month." In this type of service that garuntee could come and bite you one month with a large amount of returns to which you're paying the shipping on. -Insta bankruptcy- so don't make those promises right off the bat until you're on a good run and know costs, avg return rate, profit levels/have investment backing/etc so that one slip up wouldn't result in a the end of the business.

My other issue in this is vagueness of 'favorite things' and 'tastes'. You can only have so many variants each month, 10 gifts that you've bought wholesale amounts of and will have your system sort who should be getting what that month. Going overboard with trying to pick the perfect gift for every single individual isn't scalable and wouldn't attract high profits since you wouldn't be purchasing in large quantities.

Other than that, I think it's a good idea. Tough part will be figuring out the price point so that you're distributing high quality gifts at a price that someone is more than willing to pay every month.

Single accounts per device id/email/etc. with a usage throttling on free accounts would greatly limit competitors from blasting your system with spam that you'd have to pay for.

As far as not losing money in general, twillio is a great service but it's also one of the more expensive. There are competitors now so shop around a little bit. Overall though you'll most likely have to have a good advertisement system, some type of affiliate sales, or initial paid users to keep it running for awhile without investment backing.

For me the problem is not so much the lack of targeting the ads for the business but instead the traffic you'll receive. Lets say you call some businesses in your area and they jump on board since it's a dollar, very little to lose if it doesn't produce any results, perhaps 10 of these businesses decide to do it and 10 more randomly from the internet(most of which will be spammers trying to get hits for their site). You've now spent time building, making sales calls, etc. to earn ~$20. You now also have to get 20000 impressions to these jokes. Since odds are that the business owners go the quick route and just nab a popular joke from another site (copied content, google doesn't like that) you're not going to have high rankings and are in direct competition with large humour sites that everyone knows by name because of their high brand recognition.

Point being: regardless of price points, CPM, what business advertises, etc. it's highly unlikely that you'll get large amounts of people looking for jokes traffic as well as business looking to advertise this way. Don't get me wrong though, if you want to build it then do just that but do it because you want to or keep working out some of the kinks until you have a strong model. At this stage though it is not really a 'business' and is a flawed model when it comes to CPM prices and potential revenue.

I agree fully with the two other comments. Working for or even starting a startup can lead to great financial success, a good resume, great connections, and a fun experience. It however is a big risk due to lowered salary and sometimes infinite work hours. This risk however has a lower effect when you're young and don't have the expenses or time that someone who is married and has 2 kids has. Additionally as laservr said, do your homework. Since you're taking a risk with that startup you want the odds that you come out of your employment a rich man to be as high as possible. If you see that the idea/company is failing or don't believe in the idea then don't work with them.

Short advice: Go for it, but approach with caution.