Giancarlo Massaro, founder of AnyLuckyDay.com, and TheStartupist talk shop about his latest startup and startup strategy. Enjoy!

AnyLuckyDay.com is an alternative advertising source for companies looking to promote their products and services. On the flip side, people can win the products and services that companies sponsor on our website. It’s a win/win for everyone.

How did you/your team come up with AnyLuckyDay?

GM: In late December 09, I was laying on the couch after midnight watching television and trying to think up an idea for a website. I saw an infomercial on TV and thought to myself, “wouldn’t it be cool if they let you test these products for free before you bought them”? I started to build off of that idea, and Any Lucky Day was born.

AnyLuckyDay is a startup trying to crack a tough niche. Essentially, AnyLuckyDay is attempting to make money giving stuff away for free. What makes AnyLuckyDay the greatest success story for this niche so far?

GM: You’re right, this is a very tough niche, and one that is tough to profit from. I believe what makes us the greatest success story so far is our unique range of products and sponsors that have been displayed on the site. We have a direct relationship with every company that has been featured on our site — unlike many other giveaway sites who simply purchase products and then give them away.

Many entrepreneurs (esp. those who make a go of things online) are constantly trying to find advertisers. How would you advise other startupists to seek out and secure advertising/giveaways?

GM: While I will not speak entirely of our strategy to secure advertisers, I can tell other startupists this: Make connections, introduce yourself to people, and have a pitch that is short and simple. Let people know what sets you apart from the crowd and why they should advertise with you or sponsor you. I’ve been rejected hundreds of times. I’ve been persistent though, and from a handful of those rejections the advertiser/sponsor had a change of heart as a result of my persistence.

What marketing challenges has AnyLuckyDay come up against as a startup/new competitor?

GM: Product giveaways are common allover the internet. The biggest marketing challenge is having people enter a giveaway, and also return to your site for future giveaways. Many times people enter a giveaway, and will never return to, or remember the site ever again.

Where do you see AnyLuckyDay going short-term?

GM: It has been about 7 months since we went live and we have only grown larger since that time. Our main focus right now is to build our brand so that people will immediately recognize us when they see our logo. Within the next few months I see us obtaining more sponsors and becoming one of the more dominant and recognized contest websites.

Failure is an important part of business. Describe a few of AnyLuckyDay’s failures, and how you managed to overcome them.

GM: We have had many failures in the past, especially when we first launched the site. Our pitch was not strong enough, and securing sponsors and advertisers was impossible. In addition, our website layout turned away many advertisers who felt that their product was not a good fit for our site. We’ve overcome these failures with a strengthened pitch to secure advertisers and a newly enhanced layout which everybody has been excited over.

How can people get involved with AnyLuckyDay?

GM: People can get involved with Any Lucky Day in a few ways. If you are a user, you can simply enter our contests by posting a comment in order to win. If you have any comments, questions, or suggestions for the site, you can simply contact us via our contact form. Finally, if you are interested in sponsoring or advertising, you can contact us via our sponsors page.