AnyLuckyDay: An Interview Four Years In The Making – with Giancarlo Massaro

You’re about to meet a guy who’s been asking me to interview him for the past FOUR YEARS.

The first time was soon after he launched. I researched his company and, of course, I said I couldn’t do the interview.

But he kept me updated on his progress and I think it’s time.

Giancarlo Massaro is the founder of AnyLuckyDay, a contest site where contestants get more entries for promoting the contest they enter.

Watch the FULL program

About Giancarlo Massaro

Giancarlo Massaro is the founder of AnyLuckyDay, which is a social media marketing platform that allows businesses to promote their products and services through online giveaways.

Giancarlo is offering Mixergy readers a free 30-day trial of ViralSweep, just use the code FREE100 after you setup your first sweepstakes. Also, two winners will get a 6 month subscription ($594 value) for free. Enter here.

Raw transcript

Mixergy’s audio transcription is done by Speechpad

Andrew: Three messages before we get started. If you’re a tech entrepreneur, don’t you have unique legal needs that the average lawyer can’t help you with? That’s why you need Scott Edward Walker of Walker Corporate Law. If you read his articles on (?), you know that he can help you with issues like raising money, or issuing stock options, or even deciding whether to form a corporation. Scott Edward Walker is the entrepreneur’s lawyer. See him at, and do you remember when I interview Sarah Sutton Fell about how thousands of people paid for her job site? Look at the biggest point that she made. She said that she has a phone number on every page of her site because, and here’s a stat, 95% of the people who call end up buying. Most people, though, don’t call her, but seeing a real number increases their confidence in her and they buy. So try this. Go to and get a phone number that will make your company sound professional. Add it to your site and see what happens.

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Andrew: Hey there freedom fighters. My name is Andrew. I’m the founder of Mixergy, home of the ambitious upstart, and you’re about to meet a guy who’s been emailing me and asking me to interview him for the past four years. The first time was soon after he launched, and of course I researched his company and got back to him via email and told him that it was just too small and too young. We don’t interview new companies. We wait for them to have a big success that other people want to emulate and to spend an hour learning about. So, that’s basically what I told him and the guy just stayed in touch with me, kept sending me updates, kept emailing me, and about four years later, I think now is the time to do the interview. Giancarlo Massaro is the founder of AnyLuckyDay, a contest site where contestants get entries for promoting the contests that they enter. I invited him here to talk about how he built it up, and Giancarlo it’s great to finally see you after writing to you for so many years.

Giancarlo: Yes, nice to finally meet you. Thanks for having me.

Andrew: So, you launched this while you were still in school. Before you graduated, how much revenue did Any Lucky Day generate?

Giancarlo: In the last two years of my college education, the junior and senior year, it made $100,005.

Andrew: $100,005 in sales?

Giancarlo: Correct.

Andrew: All right, what about profit? What do you take away from something like that?

Giancarlo: Profit was around 70 to 75 grand after.

Andrew: Really, and what do you do with that as a college student?

Giancarlo: I mean, a lot of it was going to loans. Then a lot of just went in the bank and it goes towards all the site projects that I do as an entrepreneur.

Andrew: So, you still have cash in the bank from AnyLuckyDay?

Giancarlo: Yup, yup.

Andrew: Over $30,000?

Giancarlo: Yes.

Andrew: Congratulations. That’s a nice way to go into life.

Giancarlo: Thanks.

Andrew: The idea came to you where?

Giancarlo: So, back in 2009, before this was December of 2008 actually, before I went into college I had sold off all the websites that I owned. I owned a bunch of small little websites that were generating a small amount of revenue, but I sold those all off. I went off to college, because I figured I wouldn’t have any time to do anything. I was playing Division 1 college soccer, 6 or 7 days a week we were playing. I was going to class 5 days a week, so I just said let me forget about the whole website business for now. After the fall season of soccer, my freshman year, I was laying on the couch at my girlfriend’s house, and I was like I’ve got to get back into the web business. I have no money right now. So, I saw an infomercial on TV. It was like 2 am, I was watching TV, and it was just a regular infomercial. I don’t remember what product it was for, but I remember thinking it would be cool if I could try out these infomercial products before having to buy them, because who knows how good they are. Who knows if they’re worth the money.

Andrew: Like, you’re a reviewer for things like the ShamWow [SP]?

Giancarlo: Exactly, so I review it, try it out, see if it’s worth the money. Then, that’s when I had this, the light bulb went off in my head, like maybe I could try this stuff out and then give it away to other people, and they could try it out as well. So I was thinking, maybe, a website where every day I’d give something away and anyone can win, and then I was just like, any lucky day. It could be anyone’s lucky day. So that’s where the idea came from.

Andrew: What were the sites that you had before AnyLuckyDay?

Giancarlo: The first site I started out was called “The Car Showcase”. I was 15 or 16 years old building it with a friend of mine who was a partner on some businesses, and it was basically It was a Facebook for people who owned cars and wanted to post cat pictures and had a car profile. We had built it up a little bit, and it never really went anywhere. And then the one right after that was called It was a MySpace friend adder. Basically, people paid us to be featured on the home page, and their profile would get tons of friend requests. That actually made a thousand bucks on its first day.

Andrew: [laughs]

Giancarlo: Pretty surprising. And I was 15 or 16. I saw my bank account and I was freaking out because I never earned that kind of money before. Shortly after that, I launched a site called Woo Agent, and it was a desktop widget for Basically, it would pop up on the bottom right- hand side of your screen with the new product and the price of the product that would be featured on That ended up getting 23,000 downloads and it was on Tech Crunch and Life Hacker and it really didn’t make any money, but I ended up selling it on Site Point for a thousand bucks before I went off to college. That was pretty much what I did before school.

Andrew: Who coded that?

Giancarlo: Woo Agent?

Andrew: Yeah.

Giancarlo: It was just some guy I found on a forum. I don’t remember who specifically it was, but just some guy I had found and he coded it for me. It ended up getting a lot of downloads, and it was pretty popular in the Woo community.

Andrew: I remember that. I didn’t know that was you.

Giancarlo: That was me.

Andrew: I like that about you that you’re not a developer, but we’ll see throughout your entrepreneurial experience you find someone who can develop something for you, strip it down, keep it simple so you don’t spend much money, and you find someone who will build it for you. Before we continue to AnyLuckyDay, what happened with the MySpace business? What did they do for you?

Giancarlo: FriendFleet?

Andrew: Was it FriendFleet? Yes.

Giancarlo: Basically, we had hired coders out in India. We really skimped on the development because we were young. We didn’t have much money. And so the site became very popular in a very short amount of time, within the first few hours of launching because MySpace bulletins, if you have a lot of friends on your MySpace account, and you sent out a bulletin, it would go pretty viral pretty quickly. So the site was… things were breaking, features were going down, and we were getting people that were paying us to be featured, but the site wasn’t working correctly, so we had to just shut the site down.

We put up a page, and we said, “We’ll be back in a week or two. We have to fix some bugs, and my partner and I were speaking and we were like, “There’s way too many problems. The coders wanted a lot of money to fix what they had done.” And so we ended up building a lighter version of FriendFleet called It was only supposed to take a week to build, and it ended up taking us two, three weeks, almost a month, I believe. By the time we had gotten it back up live, it just didn’t get the same amount of exposure that the first one had gotten. MySpace was also cracking down pretty hard on the bulletins. At that time a lot of affiliate offers were being sent out through bulletins, so MySpace started cracking down on everything, and pretty much we couldn’t get back to the same amount of people and sales that we were making, that we had on the first one. So, that is what happened.

Andrew: The bulletins were really popular for a while there. If you had a friend, you essentially through MySpace had the ability to email them.

Giancarlo: Yeah. Especially, I remember using these little bootleg programs that would allow you to add friends and we built up profiles, like 50,000 people. If you sent out a bulletin, you’d have tons of people looking at whatever you had sent to them. So, that’s why I knew people who were doing affiliate offers making like 20-30 grand a week or a month just through bulletins because it was so viral.

Andrew: All right. One more thing that you did before AnyLuckyDay that I want to talk about, which is you created a site for your soccer team.

Giancarlo: Yes.

Andrew: What did that do?

Giancarlo: That’s actually how I got started on the whole website business and what actually opened up my eyes to everything. It was like when I was 14 years old and my club soccer team – we were ranked like top ten in the country. We were a great team, and when you’re a great team, you travel a lot. There are tournaments all over the country that we wanted to go to and that we were good enough to play in. The issue was money, so I had just built, just one day I went on, a free website builder, and I set up a site for my team. It was just some pictures of us, the roster, and our schedule. I just sent it out to a few buddies on my team. They are all like, “It’s pretty cool. It’s awesome.” Then, the next practice I went to, all the parents were complimenting me, like, “This is so great that you set this up for you guys.” And everything. I was thinking I could make this better. Everyone likes it. I somehow stumbled across forums. This is way before I knew anything about the internet, back in 2000 or 2001. I stumbled across web design forums. I think it was Sitepoint and Digital Point, I believe. My mind was boggled that there were people on here doing web design and trading, bartering for different things. I just found someone on there. I just made a post asking if someone would help out a young guy who had a great team. Help us build a website.

I ended up finding some guy who wanted to add something to his portfolio. He coded and designed a website for free, for me and my team. I found hosting for free. I was basically going to every single host on the Internet, clicking on their live chat, sending them my story about myself and my team and how we needed free hosting. A host gave us free hosting. We basically set up this whole new, nice looking website. Then, I put some Google ads up. I just started sending out typed up letters to companies around the state, about our team, and just asking for donations and sponsorships. Through that, we got $5,000 raised through the website. The website became pretty big, just not amongst my team, but amongst all the teams that we were playing around the country, because everyone would look us up before they played us. I was doing news, updated every day. My father or my brother would videotape all of our games. I would post all the goals from the games and everything. It became pretty popular. That’s how we raised 5 grand for the team, so we could travel to tournaments.

Andrew: The reason I wanted to ask you about all these different projects that you launched is because it seems like there’s a type of entrepreneur who’s kind of a tinkerer, who just keeps throwing stuff out on the internet and seeing where the revenue is going to come from, and what happens with it. No hesitation about trying something quickly, about asking someone else to build it. No hesitation about contacting someone like me and saying, ‘Hey. You should interview me.’ We’ll find out later on in this interview that you also contacted different companies and got interesting deals from them, that other people wouldn’t have. Another guy, there are lots of guys like that. Sahil [SP], from Gum Road, was like that. He used to email me when he was still in school, and say, ‘Here’s the latest project. Andrew, you should check this out.’ He would post it up on hacker news. What I wonder is, I turned you down. I said you can’t do an interview. Lots of these people who you ask for free web hosting must have turned you down. Why didn’t that make you feel hesitant? Why weren’t you hesitant about contacting people in the first place?

Giancarlo: I look back on it now, and I realize why you said no. I realize why a lot of people said no. It was because it was too small, or the site was ugly, or you might have thought we’re not going anywhere. In my eyes, I was so new to everything on what I was doing, that I thought it was the greatest thing in the world. I thought everyone else would love it. That’s why I just kept pushing on and felt that someone out there would see the same thing that I was seeing. Eventually, I found the right people and made things work.

Andrew: That’s the thing. It’s just that you don’t see that this is too new. You told Jeremy, our producer, when he asked you what the first version looked like, you said it was ugly. Back then, you didn’t see it as ugly. You didn’t believe that.

Giancarlo: Yeah.

Andrew: I see. That’s where the confidence comes from, from just loving your baby so much that you feel like everyone must love him. Everyone must want to get to know the site. All right. OK. Now, you have this idea. It’s just starting to coalesce in your mind, and it’s time to do something. What’s the first step that you took?

Giancarlo: I went home. That week, I had just set up a word press blog. No one really knows this, but the first initial version that I had, because I wanted to monetize it from the beginning, there was going to be a pay wall. You weren’t paying to enter the contest, but you were going to be paying to access the website, to enter the contest. You can’t pay to enter a contest because it’s considered a lottery, and it’s illegal. I had a way around that. You would be paying to access the website. Then, you have access to contests.

Andrew: Basically, you are saying, “I’m creating an online casino, an online lottery. You pay in order to enter. Yes, there’s a back way that you can get in for free which would keep you legal but basically, people are paying to be entered.” What I’m wondering is how do you go from saying I’m going to test to different products online for people to suddenly getting into this contest space. Where do you make that leap?

Giancarlo: It was just kind of a notion where I was like, I wanted to try out these products and then I also wanted other people to try them out. So, I was thinking, why not just give them a way on a website where everyone can try. It can be anyone’s lucky day and then can win something and then they can try it out. And, then I kind of made the connection. Well, I need to get companies that are going to send me these products and they would like the promotion aspect of it. So, why not just give away, you know, set up like these sweepstakes and give them, give these products away. So that’s kind of where it came from.

Andrew: It was all going to be built on WordPress and you told Jeremy, our producer, that you hired a designer. What did you pay him and what did you look for?

Giancarlo: I mean the site was so basic and simple. It was just a blue background. I don’t believe I hired a designer. I hired a logo, right so I hired a logo designer, paid him like $75, I believe and he designed like. I told him I wanted, like, a leprechaun that looked like the guy on the Lucky Charms box, cereal box. And, he made a logo with a leprechaun sitting on pot of gold. And that’s what I used at the top left hand corner of the website, the leprechaun and just said Any Lucky Day in cursive lettering. And then it was just a blue background with a new blog post every day with a picture of the product that was being given away. And then a little description.

Andrew: And then, the charging access to this site. So far everything you said was very simple. You might think it was ugly in retrospect but it is simple and it works. The membership part, though, isn’t that easy. Today, you can use WishListMember with WordPress and create a quick membership section. How did you do it back then?

Giancarlo: I had paid a buddy, a buddy of mine who codes all my stuff now. We kind of like met back then and I don’t remember what I paid him but he just basically put up this PayPal button where they couldn’t access the site until they had. It was only like $0.25. It wasn’t anything crazy. It was like $0.25 to just access the website and one person had actually done it. One person actually paid. Obviously, it wasn’t enough because these companies weren’t going to get thousands of entries because not enough people were paying to access the site. So.

Andrew: I see how he did it. Very basic, PayPal has a system you tell it what you want to charge. You tell it even what the button should look like and where people should go after they pay. You give them the URL. They give you the button. You put it on the button. People see it. They click it. They pay and then they are taken over to the URL that PayPal directs them to. Right? And, then you started to send your pitch e-mails. Who did you e- mail them to?

Giancarlo: Like everyone. I was pitching you. I was pitching all the press outlets, local newspapers, national newspapers. I was sending them out to all the companies who had cool products I wanted to feature on the site. And, then, you know, some responded and most didn’t even bother to reply.

Andrew: OK. What are some of the products that you got as a result of these pitch e-mails?

Giancarlo: The first initial products, like Irons. These like food, the thing that you put the food in the bag and sucks the air out.

Andrew: Yeah. Those vacuum storage devices.

Giancarlo: Like little knickknacks like one company was this thing that you stick onto the back of your phone. You put your thumb through it so your phone doesn’t fall out of your hand. Some clothing. Foot video actually sent me a camera. All this stuff.

Andrew: All this just because you’re a nobody who just has the confidence to e-mail companies and say, “Send me your stuff and I’ll promote it.”

Giancarlo: I’m a nobody who has, like, this blog that I’m willing to promote their stuff on my blog.

Andrew: That blog was nothing at the time.

Giancarlo: Nothing.

Andrew: It was just that. So good on you for doing it and impressive that you got those responses from people. Now you have it. It’s time for you to do something. It’s time for you to start getting traffic. What did you do?

Giancarlo: Basically, I found all these contest directories. And, I would just take the link that was for the contest and I would just post it on all these contest directors. It looked like this huge sweepstakes community out there and they will enter any sweepstakes that you can imagine. And, so a lot of the traffic was generated through those contest directories. Just getting them featured.

Andrew: I ran a site call that a offered a billion dollar jackpot or a chance to get a billion dollar jackpot, backed by Warren Buffett. And, as we got entries, I noticed the same thing that you did. There are people out there that just enter contests and they might as well because we really do give them out. You sent out those irons?

Giancarlo: Yep. Yes. I sent out everything. Now, that was my initial mistake. I was requesting all the products from the companies first and then I would ship them to the winners. Then I was like wait a second. I’m losing money here and I’m not making any money because I was paying for shipping costs, but I was really shipping all those products to the winners. It’s crazy because there are money on the Internet that just sit there and enter sweepstakes all day. That’s all they do.

Andrew: And the newer sites are actually better for them because it means that there are fewer contestants.

Giancarlo: Yeah.

Andrew: Entrants. OK. So I see how you’re getting traffic. You quickly drop the pay wall. Why?

Giancarlo: Well, it was just basically seeing that if one person was paying to get access to the site, then every contest is going to have one entry and the companies are going to be like, “What the deal with that?” So I just dropped it and then immediately we were getting hundreds of entries.

Andrew: OK. And the way that people entered was…

Giancarlo: At that time it was just leaving a comment on the contest.

Andrew: I remember that. What was your thinking behind that, behind asking people to leave a comment?

Giancarlo: I really had no other way to keep track of entries. I didn’t think of collecting emails at the time. And so I just said… I think it was disgust that was embedded on the WordPress site, and people would just leave a comment and that would count as their entry. That was it.

Andrew: OK. Where would the money come from now because you were at a point where you no longer had the pay wall, people didn’t have to pay to get in, there was no advertising.

Giancarlo: Yeah. There was zero dollars coming out. I was absolutely making no money for the first year that I was running this. Basically, I went into a low point where I stopped running the site because it was making no money, and I was just like, “Why am I bothering doing this for?” So I don’t know if you want to get into that right now, but…

Andrew: Then what happened was you saw Jason Sadler’s site, a guy who I interviewed a long time ago. What was his site?


Andrew: What did you see there that inspired your new direction?

Giancarlo: We had actually launched at the same time. He launched January, 2009. So did I, and I saw that he had a calendar model where people were paying him. January 1st, it would cost a dollar. January 2nd, it would cost two dollars. It would go up through the year where December 31st it was $365.

Andrew: And what they were paying for was him to wear their t-shirt, to do a quick video. He actually promotes the hell out of them on Twitter and other sites, but essentially if he wears your t-shirt and does whatever he’s going to do on social media for the day. Companies want to buy early because they get to buy in cheap, right? He’s since increased prices, but you saw a model there What did that inspire you to do with your business?

Giancarlo: So it was actually November of 2009. I was sitting in a business law class and just drawing in my notebook trying to think of ideas of how to monetize the site because from June until, I believe, October I didn’t touch the site at all. I let it die out. I had started playing Division I soccer. We were in pre-season. I didn’t have any time to run the website, and I was making no money. So I just stopped working on it. And then I got an email in October from one of the people that had been entering the contests and they were like, “Where did you go? I love the site. Is something wrong? Did something happen?” That’s when I kind of realized, “Hey, I have something here. I just need a way to monetize it. So I was sitting in business class, and I remember seeing Jason’s calendar and I thought, “Why don’t I just charge companies every single day a price to have their contest featured on AnyLuckyDay?”

I went home right after that class, got on AOL’s Messenger and started talking to my developer, and I told him, “Look, I need you to build this calendar for me.” He charged me like 300 bucks, and basically I changed it to $1.50 increments a day. January 1st was $1.50. The 2nd was $3.00 and so on. I was like, this is how I’m going to launch this site in January of 2010, and that’s what I did. I had a calendar model, and that’s how I monetized the site.

Andrew: OK. And it would be you would do a video for them?

Giancarlo: Correct. So I also started doing videos. So it would be the contest featured on the home page as well as a video, and they would be paying for the day that they bought. So if they bought January 1st, they would $1.50. They would get the contest. They would get a video, and they would get hundreds of people entering their contest for a chance to (?) products.

Andrew: And would they get the email addresses of the people who entered the contest?

Giancarlo: No. I didn’t have any of that built into the site. It was just, leave a comment on the contest for a chance to win. That was it.

Andrew: Right. So now you need over 300 companies to participate. You can’t send out that many emails. So you discover something else.

Giancarlo: So it was in December, the calendar was finished. The December, 2009, calendar was finished and now I said, “OK. Now I have to start selling this out because I told everyone about this. I was telling all my friends, all my family, and I told them about this great new model that I was doing and how it was going to make money, and, you know, now I don’t want to embarrass myself by not selling a single day.

So at first, I started just cold emailing companies, telling them about the idea, and a lot of them had bought in because it was so cheap. They were just like, “Hey, this just sounds cool. I’ll try it out.” And so a lot of them kind of bought in. And I sold out, like, the first week or two of January, because it was so inexpensive.

And then I looked into HARO, Help a Reporter Out, and I saw their ads, and I had seen that a lot of people were getting great, you know, a great amount of sales and feedback from the ads. So I emailed Peter Shankman, and I asked him, you know, if I could buy an ad. And he told me it was $1,500. So I’m, like, a broke college student at the time. I didn’t have that kind of money, I had, like, maybe $500, $600 in the bank. And I was just like, “Uh, thanks but no thanks.”

And then, like, a week went by, and he emailed me on, like, a Thursday night, I believe. He goes, “Hey, you can have Friday night’s HARO for $1,000 if you buy it right now.”

So I was like, “Oh, jeez.” So that was, like, $500 cheaper. So, I didn’t have the money, so I went downstairs, I talked to my parents, my brother, and I told them, like, I kind of had to pitch them the idea, telling them, like, how big HARO’s reach is, and how this could help the business. And my brother and my parents were more than willing to give me the extra money that I needed to buy the ad.

So they did, and I bought the ad, and it’s history from there.

Andrew: Let’s pause, and we’re going to dive into what happened next, because it was exciting. But I guess, just about everyone in the audience knows about Help a Reporter Out, but I’m thinking maybe there’s someone who, like you, is a student, who’s listening to me and just getting started with business, the way you are, and hopefully one day they’ll be doing an interview here. I want to catch them up on what this is.

HARO is an email that Peter Shankman sends out. He did it a couple of times a day. He then sold his company. The email was a list of reporters looking for people to interview and to report on, and at the top of that email was a big ad, and I think there still is a big ad. He sold it for $1,500 a pop. You got $1,000. That’s kind of a good reminder that if you’re going to buy an ad, you might as well negotiate. You might as well see if you can get a lower price. Don’t negotiate with me, because we don’t even have ad spots, and when we do, I refuse to reduce the price.

Giancarlo: [laughs]

Andrew: But it’s still a good idea for most places.

All right, so now you’re in there. You think your world’s going to change. Actually, let me make this other observation about you. I’ve got to say this. The first version basically tanked. It didn’t go anywhere.

Giancarlo: Right.

Andrew: But when you have this new idea, you believe in it, like a guy who could never fail at anything. You’re right back believing that this is the greatest thing, that this business is going to make you rich, and of course you go and you talk to other companies and people and your family with the same belief as someone who’d never failed before.

Giancarlo: Right.

Andrew: I admire the hell out of that.

Giancarlo: Thank you. [laughs]

Andrew: All right. So, you’re going to them, they give you the money, you have your ad placed in there, and what happens? Do you instantly get flooded with reporters?

Giancarlo: Yeah, so, I was sitting at the dinner table, dinner with my parents, my brothers, and I had my laptop sitting right next to me, and then I had, like, my food right in front of me.

Andrew: [laughs]

Giancarlo: And the email in the evening goes out about 5:30, 6:00 Eastern Time. So, you know, 5:30, 6:00 came and went, and I saw the ad, and I was like, “Oh, sweet, like, the ad’s out.” And then, you know, nothing. And then, like, you know, two minutes go by, nothing, and five minutes go by, and I finally get a phone call. Because in the ad, I put, you know, my phone number and my email address. So I finally got a phone call.

And so, I got up from the table, and I went to the office, and I started talking to the person. And they were asking me questions, like, they saw the ad and they wanted to know a little bit more information.

By the time I got back to my computer, I had, like, 30 emails, like, 30 sales, and then I’m just sitting there. I couldn’t even eat dinner. And then, just, every refresh, I was making, like, a new sale through HARO. And it just, I sold out until May from that one ad.

Andrew: Do you have a sense of, do you remember how much money you got from that?

Giancarlo: I don’t remember. It was, like, over $5,000, I believe, in just that one night.

Andrew: OK.

Giancarlo: It kind of trickled, more trickled in throughout the week from that one ad. But I remember just, like, celebrating, going crazy, jumping up and down with my parents, because, you know, this idea that I had worked so hard on was finally, you know, starting to work, and was finally starting to make money.

Andrew: Doing a video a day, though, seems easy. Hey, you put the camera on, you don’t really need to be professional, you just chat into the camera, you’ve got a product to talk about, you know what you’re going to say. Was it that easy?

Giancarlo: It wasn’t that easy. The first — people can look back at my YouTube channel, the first videos I ever made, and from, like, January 1st until maybe, like, May, I was, like, filming these either in my basement — horrible lighting — or in my garage, which was a huge echo. And it was just, I had never been on camera, so it was just very awkward for me, and just, it’s awkward to even watch the videos. And then I was like, “Companies are paying for these. I’ve got to increase the production value, and I’ve got to increase the value for them and make these videos look good.

So I started getting into green screening. I did a little research on green screening. I bought a green screen. I bought some studio lighting, and I tried to increase the production value of the videos. They did increase with time. They got better, but doing a video a day is not easy, especially when you’re in college going to class, you’re trying to have a social life. Your friends are going out on a Friday night. You’re like, “I got videos to do for Friday, Saturday, and Sunday. I can’t go out, guys.” It wasn’t easy doing 365 videos that first year, definitely not easy at all.

Andrew: Unreal. I still don’t see $100,000 in this business. I see excitement over a lot of orders. I see an ad that more than paid for itself, but where does the rest of the money come from?

Giancarlo: After the first ad, a lot of people began to hear about it, just from (?) people talking to other people about it. When I look back on it now, I don’t understand how some companies could have liked what they were seeing because there really were no tangible results that you could receive other than hundreds of comments on They weren’t getting email addresses. They were probably getting a little bit of traffic from the website, but there really was nothing of value but for some reasons these companies just loved my videos that I was doing for them, and they just loved that people were talking about their products. A lot of people were coming in from referrals. Eventually, it got featured on CNN, on Career Builder, a bunch of other websites which brought another round of sales. Then I just continued to do Harrow [SP] because it was really working for me. In the first few years Harrow was my main driver of business, and that’s what I used to get all the clients.

Andrew: So why did you stop? Why did you stop doing videos?

Giancarlo: I stopped doing videos after I graduated college. So that was the first two years where I made $105,000, and then I stopped doing videos because it was taking over my life. It was just like, if you want to go away over the weekend and do something, I’ve got to do videos first. The videos take time, they’re not easy to do, and I was just looking forward, I don’t want to be doing this my whole life, making videos every single day. I changed the model a little bit, and I stopped doing videos on a daily basis.

Andrew: I don’t know how Jason Sadler does it.

Giancarlo: Yeah.

Andrew: I mean, day in and day out, he does videos, he does live chats, he does tweets and Facebook profile change with a photo of him wearing the shirt of the day. Unreal. After I interviewed him, I must have gotten, maybe, half a dozen requests for interviews from people who said, He’s doing IWearYourShirt, he’s doing IWearYourHat. He’s just one guy. It’s my family wears your shirt. It’s a whole family of people right down to the little baby wearing the shirt. I said, “No” because they were too early. It’s the same reason with you. I wait to talk to companies way later, and way later never happened for them because it’s just such back breaking work day in and day out. It screws with you mentally. What do you say on camera?

Giancarlo: Yeah.

Andrew: You start to question yourself.

Giancarlo: Yeah, I mean, and he was doing live video as well every single day as well as produced videos. I was doing videos, and I was complaining about it. I was also in college at the time. I don’t believe he was, but still a lot of props to him.

Andrew: But really to you, too, for going as long as you did. I don’t know when he’s going to stop. He’s got to at some point. It’s got to be a standalone business that works without him.

Giancarlo: We’ll see.

Andrew: He seems to keep going. I’m looking at my notes from Jeremy, and there’s something you told him about an email you got from Kodak.

Giancarlo: Right.

Andrew: What is that? We don’t understand it.

Giancarlo: So this was before the site was monetized, so this was 2009. I was sitting in my girlfriend’s dorm room on the couch, and I got an email from… Actually, she had asked me… She was like, let’s go watch a movie; come hang out. I was like, “I’ll be there in a minute.” I was in the common room, and I was like, “I’ll be there in a minute.” She ended up going to bed and falling asleep. I got an email from Kodak, and they’re interested in sending me a camera to feature AnyLuckyDay. This was huge because this is Kodak. They want to work with me. So I was freaking out, and I was no excited and she came out, like a few hours later in the common room. She started yelling at me and freaking out that she had told me to come to bed. I said I was going to be there, and she was just yelling at me because the business was taking over my life because that was all that I was doing. I loved that I was doing, and I was focusing more on the business than I was on her. So that caused fights.

Andrew: I see. You guys still together?

Giancarlo: Yeah, we are. Almost five years later, we’re still together. I kind of figured out the life/work balance after the first year and figured out how to manage things so but in the first year I was all business, nothing else. Everything else was secondary.

Andrew: It is really tough for someone to be dating an entrepreneur in this stage in the business. Alright, so I see, tough with the girlfriend, tough with videos, tough on your social life and you have to keep this thing going and going and going. You said you stopped and I understand it. What I’m looking at right now, when I go to, excuse me, why do I keep saying anyday,, it’s a whole other kind of contest, one where if I click on an offer, like here’s one for design consultation and I get $100 gift card if I win, now you’re asking me for my email address, check off a box that says that I read all the rules, subscribe to the sponsors mailing and I get one more entry, after I submit I think I’m asked to promote it to my friends, right?

Giancarlo: Yes.

Andrew: How did you end up on this model now?

Giancarlo: After, in my senior year this was when I was getting tired of the videos, getting tired of the daily grind and I wanted to create more value for the clients but I also wanted to change the business model because the calendar models, it was dying out, it was getting harder to sell to companies and the daily promotion I felt it was too short. I wanted to give companies more time to get their contests out there so working with one of my friends who is now a business partner we designed up these new giveaway landing pages. When we tested them out through the whole last five months of my senior year in college to see how they convert and they convert amazing. They did so well, I was like, “we got to do this”. This is the new version we’re going to be focusing on. It’s going to be all promotions run at once, not run per day and in order to enter we collect your email address instead of just leaving a comment and that’s when we launched last year and for a seven day promotion it’s $199 and for a 30 day promotion it’s $499 and that’s the new model.

Andrew: I see and if I as a business owner want to enter, I give you the prize, you promo-sorry

Giancarlo: So what happens is a business will sign up, will send us their information, we’ll put together a promotion for them, we’ll promote it out for them. They also have their own dashboard now where they collect all the stats, they collect all the email address and then once the promotion ends we choose the winners for them through the system and then they ship out the prizes.

Andrew: No more you shipping out irons, they ship it out.

Giancarlo: Yeah, they do everything.

Andrew: They help promote it, which means did they help you collect more email addresses but you help them promote by promoting the contest which means that they actually get entrants when they put it together.

Giancarlo: Right, so it’s kind of a twofold here. What happens is when someone enters our contests now they are asked to be added to our AnyLuckyDay mailing list so we can grow our mailing lists to get more entrants in promotions. Then they’re also asked to join the sponsor’s email list and so those are the emails that the sponsor gets to collect.

Andrew: OK. I wonder what it is about these contests. I mean I understand that after you enter you’re more likely to tweet about it because you get more entries for tweeting right?

Giancarlo: Right.

Andrew: I get that part but I did something with the founder of contest domination who I interviewed here on Mixergy and I tested it out, 40% of the people who landed on the contest page, it’s like 41-42%, I forget the exact number, gave them their email address on the contest page. That is an unbelievable conversion rate. You saw the same thing.

Giancarlo: We have, just by looking at all the conversions, we have in our dashboard, it shows all the promotions we’ve run through AnyLuckyDay and the conversion rates, it’s the same conversion rate. Between 40-45% convert and it’s just such a simple way to enter. It’s like, “Hey, there’s a new iron, I can win it, just put in my email address.” and it’s so simple that it’s a no-brainer for people, it’s like “Hey, I have a chance of winning this, why not do it.” There’s no additional steps, there’s nothing crazy that they have to do. Just put in the email address, click enter and that’s done, then they’re entered so that’s why I think the conversion rates are so high on these contests.

Andrew: It is a nice clean design. Some of these products, I don’t understand why they get 40% or 35% even, there’s a wildcat shower cap. Who’s entering to win this leopard skin shower cap with a bow on it?

Giancarlo: Believe it or not the sweepstakes audience is all mostly women. Our audience in AnyLuckyDay I believe it’s 85% women so they love that kind of stuff.

Andrew: Here’s what I asked the founder of the other company, I’ve got to ask you the same thing, did you copy Noah’s App Sumo who runs these contests and is famously been doing very well with them?

Giancarlo: No, we did not copy him. Basically, I would say my partner, he works for AppSumo and so before he worked for AppSumo we actually built these contest pages. So that’s why there might be some similarities.

Andrew: It’s not that you guys copied him.

Giancarlo: No, no, no.

Andrew: It’s not that he ripped you guys off.

Giancarlo: These were actually built before the AppSumo contests that were run.

Andrew: Why do you have a partner?

Giancarlo: He’s been a good friend of mine. He was a partner with me on a bunch of my past websites that I did, and I’ve known him for ten years. He’s just a good designer. He’s got a good business mind. I wanted to bring him on board this year for AnyLuckyDay to help give clients more value for their contests, and so he helped me build these new contest pages. Believe it or not, the value has been great that the companies receive, and they love the new model. And so he’s my partner on this and also my new project, ViralSweep.

Andrew: Did he develop this? I’m sorry, did he do the development for the – what am I trying to say? The coding, did he program it?

Giancarlo: No.

Andrew: You hired someone else.

Giancarlo: For designs, yeah.

Andrew: Where did you find someone to do that?

Giancarlo: The code?

Andrew: Yeah.

Giancarlo: The coder for all my stuff has been a guy that I met on an online forum about six years ago. We just basically kept in contact. He lives in Oregon, and we’re friends now. All my projects, all the sites I’ve done, he codes them all for me. So whenever I need work done, I send it to him, he sends me a quote, he codes it for me, and then I take over from there and work on it.

Andrew: What’s the revenue like now on the business?

Giancarlo: It’s dropped a little bit. I would say maybe under 60 this year, but also the reason is I haven’t been focused on AnyLuckyDay this year that much. I’ve had another business called Pump Ups which we recently sold, and I’ve also been building this new product for the past eight months called ViralSweep. Anyway it’s kind of phasing out. There’s a whole shift right now that I’m seeing where, back link when any of it started companies were having contests run, tons of blogs. They weren’t really running them on Facebook, and they weren’t really running themselves on their own websites. Now there’s this whole shift where there’s tons of contest apps out there where companies can run their own contests. They don’t need to hire a third party to run it for them like AnyLuckyDay is.

So that’s what Viral Sweep it. It’s basically a website that allows companies to build and run their own giveaways on their own website. That’s what I’ve been working on.

Andrew: OK. Fifty to $60,000 in revenue this year, 2012. That’s what we’re expecting and we’re at the end of November. Today is November 28th to give people a sense of how well you guys are doing. And so why give that up? Why phase it out instead of… or hire someone to manage it.

Giancarlo: Yeah. We’re not going to phase it out. We have some ideas for what we’re doing in 2013. I can’t reveal anything just yet, but it will be a little bit different next year. The site is going to be more automated, and I believe it will be able to generate more revenue with less work, and it’s going to be mostly automated. That’s all I can say for right now, but we’re working on some things.

Andrew: All right. Pump Ups, I know what the revenue is, but we agreed that we’re not going to talk about that publicly.

Giancarlo: Right.

Andrew: Not the revenue, but what you sold it for, partially because the people who bought it are Mixergy listeners and they prefer not to have our audience hear the number that they bought it for. Let’s quickly talk about that. What is Pump Ups?

Giancarlo: So Pump Ups was a subscription service where every month you get a box of supplement samples sent to your door for ten bucks. And so I came up with this idea with my younger brother who is also a Mixergy listener. We basically had the idea for… We saw Birchbox, and Birchbox is the same thing for beauty samples for women. We didn’t see anyone doing it for the supplement space, and we thought about this back in March. We basically validated the business, built it, and had our first sale within the first two weeks. Basically, in May we had officially launched. Validating it, all we did was go on Reddit. We went on body building forums and we said, “Hey, here’s the idea that we have. Who would pay for this?” People said they would pay for it. Then we just found supplement companies. We emailed them. We said, “Would you participate if we built this?” And some of them said, “Yeah. Definitely.” We actually met with a rep of a company who said he would be all for it. So we built it up, $500, that’s all it cost us. It’s just a very simple system, just a home page and a back end. And then it’s built in with Stripes so we can process payments, and that was it. We launched it in May, and we ended up growing it to 200 customers. We ended up selling it in the end of September, early October.

Andrew: And it’s the supplement company that ship out the supplements for you?

Giancarlo: No, so what happens is, we’ll tell the supplement companies send us ‘x’ amount of samples for this month and we do all the shipping ourselves. So, this is, I kind of wanted to get into a business where it wasn’t a service based business online. I wanted to learn, kind of like, the, you know, packaging and shipping business. So, supplement companies were sending us thousands of samples. We ended up learning, you know, where to buy packaging. We learned to use [??].com for shipping and we were packaging and shipping everything ourselves. So, you know, we learned that whole business and I’m glad we did it because it cost us really nothing to set up and we made good money off of it and we learned a whole new separate business than what we’re used to.

Andrew: This is May, 2012. You launched it. When did you sell it?

Giancarlo: End of September, early October, we sold it.

Andrew: OK. And we can say, mid-five figures.

Giancarlo: Yeah. We sold it for.

Andrew: Mid to low.

Giancarlo: Mid to low five figures.

Andrew: All right.

Giancarlo: And it made about, made just under $9,000 in revenue in the months that we ran it.

Andrew: OK. Oh, wow. I like how just keep launching stuff. You just keep testing. Do you feel that when you eventually find something that works that because you’re so, you’re so eager to try something different and so creative that you won’t stick with the one thing that actually works and build it up?

Giancarlo: I think I’ve trying to find the one thing that works. With Any Lucky Day, there’s, I never really felt that it would be that business that I would be running forever. It’s kind of like that one man business. It’s my face of the business. Everyone knew it was me doing the videos. And, so, that’s why I never really felt it was going to be the thing that I was going to be running long term. A lot of the things I’ve done are all short term projects. I knew I wasn’t going to be running them long term. But, what I’m doing now, Borrow Sweet, I believe, is going to be the long term project that I’m going to be sticking with for a while and that is partially why we sold Puff Ups. I kind of was doing too many things at once and I wanted to just cut back on everything I was doing and focus on this one thing.

Andrew: All right. I want to do a quick plug and then I want to find out about this one thing, about Borrow Sweet. Before I get into a quick plug, I’m looking at your email again. One of the things that I like about your email and that we kept going back and forth so much is, dude, even back when you were just a student, you kept your frickin’ emails short.

Giancarlo: Yeah.

Andrew: And right to the point. I see you are the founder of Mixergy. My site helps companies save money through rough times by getting the most exposure and bang for their buck. And you’re really just pitching quickly and so I responded in three sentences or less. You respond back in two sentences. Yeah. Just like right back and forth. I love that.

Giancarlo: Yeah, I mean I try to be quick and to the point.

Andrew: All right, so usually at this point I would talk about and tell people that if they want to learn from entrepreneurs that that’s the place to do it, but I’m not going to pitch. I’m going to ask you. You’re a guy. An entrepreneur that’s been listening to Mixergy. Don’t even pitch Mixergy Premium. Just say, why do you listen. What do you get out of it?

Giancarlo: I just love learning. That’s, I just love learning things from other people that have been there and done it. Every morning, I just, I’ll sit down and eat breakfast. I’ll put my laptop in front of me. I’ll pop up Mixergy. I’ll watch if there’s a latest interview, I’ll watch it during breakfast. I just like, you know, sometimes, I learn nothing. Sometimes, I’ll learn something, even like a little hack or growth hack that someone did. And, I’ll just add that into my list of, you know, things that I need to do or things that can help me in my business and that’s why I watch Mixergy.

Andrew: What kind of interviews do you want to see me do more of?

Giancarlo: Let’s see. More of smaller guys like me that have smaller businesses and how they’ve kind of done it. Maybe not people who are always made millions and been there and done that and made millions but people who have made you know, $100,000, $200,000 and how they have done it and I mean that.

Andrew: You know what? We get requests for that. I don’t understand it and so I keep saying our focus needs to be on the bigger companies and frankly, to be honest with you, Jeremy and I were talking a little bit about whether this interview itself made sense because it was just about $100,000 over a couple of years. That’s basically a salary, but now that I’m doing the interview I see that it’s not just a salary. It’s not about the money. It’s the creativity and the drive that went into it and the different ideas that you experimented with that I think there’s a lot to learn from. What do you want out of the smaller companies?

Giancarlo: I mean what I’d say is it’s not always about the money but about the learning and how people have done certain things to get to where they are. And also I don’t know that everyone watching will be a millionaire and going to make that million dollars but they may make that hundred thousand or two hundred thousand and it helps them relate to the person they’re watching in the interview. So I think that’s why you may get a lot of questions back.

Andrew: All right. Jeremy always tells me, “Andrew, stop promoting just the courses, tell people there are about 800 interviews in there.” If you’re Mixergy premium member, you get access to all those interviews. You listen to them in the background as you eat breakfast, as you’re commuting, as you’re running, as you’re going to the gym, if you’re travelling for a long distance like I do, those are great programs to listen to and those stories will be interesting for you, I hope. I know certain kind of outline to keep them entertaining and inspiring and the ideas that you learn from them if you’re a premium member, you’ll see, will just be embedded in your head and one day when you’re not even expecting it, you’ll go, “Oh wait! I have the solution for it, I don’t know where. Oh right, I heard it somewhere.” and then that solution will come to help you with the problem that you’re dealing with in business. So, go to and sign up if you’re not already a member and if you are a member, just start listening to all those programs. And thanks for being a member because you’re supporting the work here that we’re doing at Mixergy. So, this is a new thing, ViralSweep. I wasn’t even sure if we were allowed to talk about it. What is ViralSweep?

Giancarlo: I see it as the next evolution of any lucky day. Companies are running promotions themselves now because there’s a lot of companies out there that help them build and run their own promotions. So, that’s kind of where I see the tide going. And so, we’ve been working on Viral Sweep. It allows you to build and run your own give-away on your own website. So we give you the tools to build the give-away and it spits out a snippet of code that you upload to your website on a blank HTML file and then the give- away appears. We have a whole thing where you can do domain mapping so the give-away will show up on your own domain on whatever URL you desire. We do stats, so we track everything for you from entries to likes that are brought to you from the promotion, tweets, followers, we track everything for you. It’s where I see everything is going to be going. Everyone is going to be running their own promotions themselves and so that’s what I’m getting into now. Maybe we’ll do a follow-up interview in a year or two and we’ll see where I’m at with that.

Andrew: I know you’ll keep me updated with how things are going with it. I see here, I just went to and I see the case study. This is a great way to start promoting, by showing others how well your current customers are doing. I see here, Blue Lounge offered a mini dock?

Giancarlo: Right.

Andrew: You guys created a contest for them that they could embed on their site. Looks beautiful, I like the background on this.

Giancarlo: They actually created their own contest that they put on their site. We give them the tools to do it. They do everything themselves.

Andrew: I see. So they put that image as a backdrop, they designed it, right? Then as a result, they got 2500 email addresses in 6 days.

Giancarlo: Right.

Andrew: And that’s what you’re doing for companies. Getting them awareness, but also email addresses.

Giancarlo: Right. We’re helping them launch and run better give-aways that help them get more entries and helps them collect a lot of data on the give- away so that they have something tangible to base their give-away off of and whether they’re successful or not.

Andrew: All right. It’s up and running right now, right?

Giancarlo: Which one?


Giancarlo: Their might be a demo. I could show you a demo one. If you go to, this was just a demo we put up where you can see a demo give-away.

Andrew: I see. But if I want to, I could create a contest on the site right now?

Giancarlo: Right. We just launched this week publicly, we haven’t really told anyone about it yet but we’re just testing with a few customers. A few months ago we did a closed beta test and that’s where the case study is from with Blue Lounge.

Andrew: The design is so nice on this. I like how when I scroll, two things happen. I don’t even know if I should give it away. I won’t give away all of it. One thing is when I scroll, the email input box and company name input box stay at the top even though I scroll. But it’s the background, what you guys did with that that’s really cool.

Giancarlo: Yeah. We try to keep this really simple. If you sign up, the dash board is even simpler. I actually just got off a Skype meeting with a recent Mixergy interviewee, I don’t know if I should say who, but we just talked about it and they want to use ViralSweep and they were saying how awesome the system is and how simple it is to use. So, I’m looking forward to seeing where this is going to go in the next year or two.

Andrew: Me too. Thank you for doing this interview. Thanks for not taking it personally when I said no and for coming back here now and talking about your business.

Giancarlo: No problem, thanks for having me.

Andrew: You bet. Thank you all for being a part of it. Bye, guys.

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  • Melvin Emilio Cedeño

    Great Interview! He knows what he’s talking about, it’s hard to find a interview of a sweepstakes expert, that is both entertaining, and insightful. I’ve been running a daily give away for about a year now, and Viralsweep is something I wish I would have had ages ago! He even set up instructions for how to run it on shopify and it’s one of the easiest set of instructions I’ve seen for shopify. Kudos Amigo! Great Job!

  • Nate Andreshak

    Andrew, I like interviews about smaller companies as well. I actually feel like i get MORE value most of the time, because normally the time period that has past is shorter and they are more likely to reveal tactics and insights, rather than a really successfully person that can barely remember everything they did to get started.

  • Paz Aricha

    Great interview, Thanks Andrew and Giancarlo :)

  • acoyfellow

    This is one of my favorite interviews, thanks guys

  • Giancarlo Massaro

    Thanks Paz, glad you enjoyed it.

  • Giancarlo Massaro

    Appreciate it Jordan, glad you got a lot out of it.

  • Giancarlo Massaro

    Thanks Melvin, happy to help you in anyway that I can. Glad you found the set of instructions helpful :)

  • Chase Carter

    Awesome Interview, guys! The most inspirational interviews are those about the guys that you can most easily relate to and Giancarlo is certainly that guy.

  • Alex

    What was that site that shows up in the transcript as:

    “We learned to use [??].com for shipping”


  • Giancarlo Massaro

    Hey Alex,

    The site that was mentioned is

  • Andrew Warner


  • Andrew Warner

    Thanks. What do you like about it? What do you want to see more of here?

  • Dustin Dell’Era

    I ditto Giancarlo, would like tohear from smaller startups as well! My 2nd son is named Giancarlo, hope hes as entreprenurial as you!

  • Stuart Fingerhut


  • Stuart Fingerhut

    I second that. small victories are as inspiring and informative as BIG ones. Big ups to Giancarlo and all his success!

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