Jason Moore is the 26 year old Co-Creator and President of the infamous PYZAM.COM, notorious for the millions of free flash toys and web layouts that are dispersed via the internet worldwide on his site every month.

Young and ambitious, Jason was a theater major at the University of Arizona for acting and directing. Due to the peaked interest of his computer savvy skills on his website MYWEBSITELAYOUTS.COM, Jason and peer, Robert Nelson of FREEFLASHTOYS.com, from his cell phone sales days, decided to merge sites combining efforts to pursue their passions making websites.

The two banded together to create the media powerhouse known today as PYZAM.COM. They found out most users from their sites had been bouncing back and forth between the two sites and made the merger to provide a one-stop-shop. As they say “The sky’s the limit!”

Success came with remarkable speed, the site opened shop in 2006 and in 2008 PYZAM.COM is one of the Top 500 websites in the United States and one of the Top 2000 globally. The site easily traffics in nearly 4 million hits a month and is the largest free content website for social networks like MYSPACE.COM, FACEBOOK.COM, etc… globally! Their widget reach is actually more than GOOGLE.COM’s and are all absolutely free!

Jason has learned to heavily rely on his user base with PYZAM.COM to set the standard for ever-evolving social content and offer high quality graphic designs, making this site an industry leader. Jason stresses that anyone looking to get into this prospective field as a graphic designer or programmer to find something that develops the passion in what you are doing. To find something that you like or enjoy (widgets, applications, etc.) and improve them! To always be open to opportunity because there’s never a linear path to your destination, life has a little bit of fate you can’t control!

Brian Hugaboom, one of the Collins College interns, interviewed Carolina Barnes, the owner of Digital Dream Forge.

Carolina runs Digital Dream Forge to develop web games, build websites, and e-learning programs. One of their clients if Kaiser Permanente. She wears many hats within the small business organization. She’s the CFO, part of the creative team, makes sure everything gets done on time, and takes out the garbage. And she works out of her house.

Most of the games she works on are for kids in the educational realm. But there’s one requirement for the games as well- they have to be fun. Seeing the kids play the games she makes is the most rewarding part of her job.

He is 25 and candid. He is currently employed as the Director of Marketing for a small start up. He categorizes himself as someone who could have been a millionaire a few times over.

How did I get here today? Well, it’s all failure. Pretty much my whole life has been a failure. You usually only see the happy parts. No one ever sees failure. Frankly, I never thought I’d be this old. I thought I’d die. I don’t know. I didn’t come from the hood. I didn’t come from the streets. I’m from Cupertino, the most suburban area you’ll ever be in.

I got an internship with Microsoft my junior year at UC Berkeley. Normally, anyone who gets an internship gets the job. I was rejected.

I had a job offer at Google pre-IPO and they rescinded it for some reason. I don’t know, maybe they didn’t like me. I would have been really rich, pre-IPO Google.

Was going to go work at Wells Fargo and then I applied for a women only job at Intel. They were like, sure we’ll hire you. But not for the women’s job, for this other one. That would have been tight if I dressed up as a women to get the job though (Laughs).

With that, I went to Intel, and I loved Intel, but it was like the best and the worst for me. It was a job that was close to home, they paid me a lot of money for doing Excel work. But the people there were going home at 5 and they were soccer dads. That was their life. Some people that are at Intel are really unhappy…but that’s everyone in America.

I was really interested in meeting new people and talking about the web and being involved and making things happen. That’s what I say when people ask me what I do for a living. I used to say I worked at Walgreen’s because I didn’t want people judging me for better or worse based on my job. So what do I do? I make things happen.

I dropped a resume at Facebook because I like the web and I like people. I did a lot of college marketing to college businesses and so they offered me a job. I went in there, did product management for seven months. I made a lot of features, met a lot of people. Worked, fucking, nonstop. Lot of fun. And then, I wasn’t good there? I’m not sure what happened there, but I did get laid off. And Marky* and I maybe didn’t get along, I’m not sure.

Things happen. I have a tough time getting over things. But you just have to keep moving forward.

So how do you overcome failure?

Fuck. I’m horrible. Even this week there was a girl I liked…fuck, I’m shitty. I don’t. Really, it’s moving on to the next thing. Keeping yourself busy. When you move on to the next thing you kind of put things in the past. You have to accept it. What I’ve done with the Facebook thing is being honest with myself. So I got laid off. That’s a really hard fucking thing for people. Especially at a company where I’d be a millionaire.

So it’s on to the next thing and becoming a millionaire in other ways. To overcome failure is accepting it, being honest with yourself, and moving forward. And just giving it time. You know this is going to suck and you’re going to be sad, but it’s going to be that way. I don’t know, maybe smoke a lot of weed, eat, drink a lot, I don’t know, jerk it? Whatever you need to do to make you realize it will be better in the future.

I think the challenge with young people is that they’re often discouraged. They tell themselves they can’t do it, or that they have to go get experience from Microsoft. You’ll never get experience from Microsoft to run your own company. You’ll just get experience on how to run a corporate company. Or be in a corporate company. Or work in a cubicle.

I guess the advice I’d give is to accept the failure and know it is going to come. Maybe deal with it better…prepare yourself for that. Maybe whatever it is that I’m scared of doing, consider doing it. Be willing to take more risks. But that’s the thing! Why am I not taking more risks today then?

Postscript: Noah decided to start his own internet company four months after our interview. He decided to travel abroad to Argentina. “Why? Why not. Luckily the internet is everywhere, so I can work from anywhere.”

Nathan Kaiser, founder of npost.com, was not sure what to do with his degree in microbiology from the University of Washington. Working for a large medical manufacturer, he began, in his free time, to interview interesting people about their jobs and their career paths. From this sprang nPost, a resource for people looking into the world of technology start-ups. The site is a collection of interviews, and also job listing specific to the tech start-up world.

Nathan has denied listing jobs from Fortune-500 companies, simply because, in Nathan’s view, it would hurt the overall character of his website. Many people thought he was crazy for leaving a well-paid position to start nPost.

“I’d rather be crazy than working unhappily,” Nathan says, “People don’t realize what they’re missing.”

Nathan may not be fully maximizing the profits of his business, but if he is concerned with that, he hides it well. “When you’re doing your own thing and supporting yourself,” says Nathan, “there’s nothing better in life. Plus, he adds wryly, “I’m wired, so I do a lot of work from friends’ sailboats.”

Dave Mathews is an extrovert inventor that has been taking things apart and finding innovative ways to put them back together since kindergarten. One look at Dave’s kitchen table will tell a life story shaped by gadgets, tinkering, and an innate curiosity to find out how things work.

With the Golden Gate bridge in the horizon, Dave and I discussed how he’s made a career out of inventing, and how it translates to anyone making a career out of a hobby.

Dave’s advice:

“First, figure out what your hobby is. What are you passionate about? What do you love to do? Is it arts & crafts? Programming? Tinkering? Whatever it is, try to figure out a way to make that your career.”

So just how can you take a crazy hobby like taking things apart and putting them back together a career?

“Well, the hard part is making money, right? I was lucky coming out of school because there was a computer revolution and all these offices needed computers set up. There was opportunity everywhere. But there is opportunity everywhere today too. The video game industry is larger than Hollywood and the film industry these days. Literally, if you love playing video games, you can find a way to play video games as a career. Whether it’s coding, developing them, whatever, there’s no excuse for you to find a job you want because there’s so many different career paths that you can take based on your hobbies.”

More info on what Dave is up to can be found on his website - www.davemathews.com

I don’t know much about software and technology, but I do know that it has made Andrew Hyde’s offline world a bit more interesting, and it has the capability to make yours a lot more interesting too.

Coming out of college Andrew expected a 9-5 job in software design working for, and hating, “the man.” But as he carted his belongings around Boulder, Andrew was turned down for a job nine times before finding a freelance gig for five hundred bucks.

The freedom of freelancing turned into a love for entrepreneurship, and Andrew began to enjoy playing the “make enough to pay the rent” game.

Now twenty three years old, Andrew Hyde has already started two businesses and is onto something with Startup Weekend. The weekend event relies on Andrew’s online connections to attract top talent to build a business in a weekend.

Check out Andrew and Startup Weekend at www.andrewhyde.net.

Irv’s email read: “I’m a 46-year old entrepreneur who has founded 40 startups before I finally got this one right. Let me know if you’re interested.” Of course, we had to schedule an interview to see how he finally got it right.

The one startup that he really got right is SysGen Inc.; where he is the President and CEO since starting the company from his home in 1997, initially offering his services as an AS/400 programmer, project manager, and computer system validation expert. He has grown that into a successful company that provides outsourcing solutions for software vendors, please visit the website at sysgeninc.com.

Sys Gen Inc. was an interesting company to hear about, but the real reason I was in Chicago was to hear about Irv’s trials and errors in entrepreneurship. An interesting analogy that Irv had to offer related blackjack to starting a business and keeping it successful. “Starting a company is like blackjack. You don’t have to win every hand, but you have to have enough chips to continue playing the game, and you have to win back some of those chips every once in a while too.”

Most of the lessons we learned from Irv in our interview relate to this theory that blackjack is like entrepreneurship. Like gambling at the blackjack tables, Irv said that the hardest part about entrepreneurship is pulling the plug on a venture. It’s just knowing when to get out is the hard part. Irv said that he’s stayed in too long, and pulled out too soon many times in his entrepreneurial driven career, much like a conservative or overly-aggressive blackjack player.

The rush of winning a hand for gamblers is the reason why they play, and Irv gets the rush of thinking up a new idea and working on it like it is the next biggest thing. The rush is what keeps a player at the tables, and Irv still thinking up new ideas. It is also why a player refuses to leave a table after losing chips, and why Irv is stubborn to leave an idea because of that slight notion that “this may be it.”

But at the same time, a player has to know his risk. If a player gets a hand of 17, they know that the risk of going over is likely and they probably won’t ask for another card. Irv recognizes this concept, and realizes that a new concept has the most risk attached to it, and his job is to minimize this risk. He does this by taking existing ideas and trying to make it better.

So entrepreneurship really isn’t that much different from a blackjack. Sure there is more creativity and complexity to starting a business, but blackjack has the same themes such as minimizes risk, experiencing a rush, and knowing when enough is enough. And Irv Segal is the seasoned veteran.