Happy Monday everyone! Today we have Kelly Smith who has a tremendous background.  Enjoy the great advice and knowledge.

Kelly Smith, it’s a pleasure to do this interview with you. We did research on you prior to doing this to find out more about the projects you have worked on. It is unbelievable how much we came up with. So, Mr. Serial Entrepreneur, can you tell us about yourself and each of these projects you have been involved with.

I have been working in the internet space for since 1994. Like many people, my career got off to an accidental start. I wound up in Seattle working as a technical recruiter when I got out of college. One of my clients asked if I would be interested in filling one of the open roles they hired me to fill. That company was called SPRY and it was the first commercial internet product sold at retail. It was called Internet in a Box. We licensed the source code for the Mosaic web browser from the University of Illinois before Marc Andreeson left to start Netscape. CompuServe bought Spry and I then went to work at RealNetworks in December1994 to help that team market and sell this idea to deliver audio over the internet. It was called Progressive Networks back then and the team hadn’t yet even figured out how to deliver audio as a commercial product. I left RealNetworks to start a very early video aggregation company. It was called RocketVox. Those weren’t the YouTube days so we were too early for video aggregation. Fortunately, we wound up selling RocketVox and becoming a software company called thePlatform. It is today one of the more popular platforms to manage audio and video online and is now owned by Comcast.

The headline on CuriousOffice.com is that Ink’d has raised $1.7 million in seed capital. That’s amazing! A lot of entrepreneurs find it difficult to actually find investors. How were you able to make this possible? Do you have any advice for those out there looking for capital?

I think there were two reasons we raised money for Inkd so quickly. First, was that we had prior success with other companies and other investments. People knew us. But the main reason was that we introduced a very simple idea that seems to serve a very large market.

Inkd is essentially a buy and sell marketplace for printed materials such as flyer templates, brochure templates, newsletter templates and more. You might say it is like a graphic design marketplace as Etsy is for handmade goods. Designers, marketers and business owners can download fully editable design files such as brochure templates, business cards, flyer templates, newsletter templates etc, which were uploaded by professional graphic designers. Each creative is unique and gets screened by the Inkd team before ending up in the marketplace. If a business owner or marketer doesn’t’t find what they’re looking for, they can put out a request to Inkd or email graphic designers directly. Creatives who submit material to the design collection are paid a royalty fee on the total retail sale for each transaction that ensues, but in the future Inkd plans to debut an ‘exclusive’ membership with higher commission fees.

Inkd print templates (of which 900 are already present) are made available for immediate download in a wide variety of file formats and include page layout files such as Adobe Illustrator or Adobe InDesign along with photos and artwork. The files are fully editable and can be customized to suit any project. You can get some free samples from the Inkd website (hover over the ‘Learn’ tab) to see how they come out. Microsoft Word and Apple iWork Pages formats are coming soon.

What we think Curious Office has done is apply a well thought-out business model that has already proven its value in other fields (iStockphoto for stock images and Logoworks for logos spring to mind) to an industry that’s dying for some innovation. The advantages for business in terms of cost and time saving are clear. And that’s a key point. Investors need to easily understand how your concept will make money and its especially helpful if you’re doing something that nobody has done before.

You started Imagekind in 2006 and then sold it to CafePress in 2008. That is an extremely fast turnaround. What was your experience like when Imagekind was acquired from CafePress? How were you able to sell so quickly?

Most investors will tell you to not worry about what kind of company might acquire you when you start out and I generally think that’s good advice. What that really means is that you should focus on adding as much value as you can and think about little else. In my case though, I tend to develop ideas about likely suitors anyway. CafePress is the largest print-on-demand company. Imagekind was the first significant marketplace for buying and selling art on demand. Once we got Imagekind up and running, we made an effort to talk to CafePress. I like to be very communicative with those who some might even call a potential competitor. Big competitors are often the most likely suitor for your business. It’s important to show them early that you can communicate with them in a mature and sensible way. It’s important to show them that you’re always open to any kind of partnership possibility and that you would be interested in growing your business by helping them grow theirs even bigger.

Now, you’re giving back in a sense by doing the investing. Can you talk about this for us?

My longtime friend and business partner Adrian Hanauer know how hard it is to start a small business. Most people know him as one of the owners of the professional soccer team here in Seattle called the Seattle Sounders which he bought with the famous comedian Drew Carey and Hollywood producer Joe Roth. What a lot of people don’t know is that the Hanauer family also owns one of the largest picture framing chains in North America as well as the largest manufacturer of down and feather products (called Pacific Coast Feather). The family was even involved in aQuantive (bought by Microsoft for $6 billion in 2007). Between his experience watching businesses grow and my experience starting my own, we knew there was an opportunity to help entreprenuers make that difficult first step. So we set-up Curious Office for seed stage investing and we have a variety of companies that we’ve worked with, besides the ones we start ourselves here out of the same office. These days, Adrian spends almost all of his time trying to win the MLS Championship but I’m still here working on the technology side and trying to get new companies like Inkd going.

You are in an investing position now and you choose the projects to fund. How do you pick and choose? What stands out for you? Do you ever fear a failed investment?

I worry about failure all the time. Probably even more than I should. Many people I know who are very successful are extreme optimists. The best example might be our lead venture investors in Inkd over at Second Avenue Partners. Mike Slade, Nick Hanauer and Pete Higgins are always laughing and having a good time. I always leave that office and remind myself not to be so serious all the time but its kind of just how I am.

In terms of picking investments, I think we try to look very closely at the capabilities of the person who is pitching the project. We know lots of people have great ideas and a lot of ambition but its very important to be able to know how to do a lot of the hands on work yourself. We also like people who are technical or developer folk who also have a great marketing sense. Those people seem to be rather rare but when you find them then you’ve found a person who can develop ideas and prioritize how hard and how long it would take to deploy that idea into the market for feedback. Additionally, I gave Curious Office that name for a reason. One of the most important and noticable traits of a great entreprenuer is that they are rarely happy with the way things are done today. They are more curious than most. Always asking questions. Always wanting to find ways to be better, faster and cheaper. Always being curious is exhausting but you’ll see that trait in every great business person.

You seem like a very confident, hard working guy. But it also appears you have a great personality. You have a flickr account with tons of really cool pictures. You keep in touch with people on Twitter. You’re always smiling in your pictures. These traits are inspiring in themselves. We are curious to know what motivates you and keeps you going?

I never really think about how I am perceived except that I acknowledge that the mood and pace in my office largely depends on the energy I bring with me every day. I can be the kind of guy who worries a lot and my good friends know that but I also believe that you are either absorbing energy around you or you are contributing energy into your environment. I much prefer to be contributing positive energy when I enter a room. It’s not always easy but I often remember how lucky I am to have such great friends and co-workers who care about me so that helps keep a smile on my face.

Any other exciting hobbies other than photography and being awesome that you would like to share?

I like Formula One although I know its not that popular in North America. I also like furniture, magazines and travel. I’ve lived in 38 different cities in my life.

Would you like to add any last words or inspirational advice?

Remember that many of the old cliches are true so don’t dismiss them. For example, “work hard”. I once read that Eddie Van Halen used to sit on the edge of his bed practicing guitar almost every Friday and Saturday night when he was a kid while the rest of his friends went out to have fun. Brute force can overcome a lot of obstacles. If you don’t work harder than most then a start-up isn’t going to work for you. The other bit of advice I’d give is to remember that life is short. If you treat someone poorly and burn that bridge don’t think it doesn’t matter. Odds are, you’ll encounter that person again and you might even need their help. I try to be nice in all cases. I sometimes get frustrated and say things that I later regret. I do that less and less as I get older. Be nice to everyone and your aspirations will be realized more easily and more quickly.