Pixelkeet is an international graphic design and web development firm that works with clients like LinkedIn, UC Berkeley and many Bay Area startup companies to design marketing campaigns, websites, print materials and branding. The company’s founder, Jessica Greenwalt, has been running her own business since high school. In addition to leading the successful Pixelkeet business, she was recently named one of Inc. magazine’s “10 Women to Watch in Tech” and is the co-founder of medical crowd-sourcing site CrowdMed.

The Start

How did you get started with your business?
I always knew I wanted to be an artist. When I told my parents, I think it was a little traumatizing to them. “That’s great, honey! But how are you going to eat and pay rent?”

I ended up enrolling in a class at my high school called Design for Digital Media. It was all about graphic design. When I was in high school, most people didn’t even know what graphic design was. It’s a well-known thing now, thanks to Apple. People now realize design is important and branding is important. Immediately, when I learned about graphic design work in this class, I knew this was the job for me. It was like meeting my soul mate! I’ve been doing it ever since. It’s something I never tire of. It’s really worked out for me.

I started building up my client base in high school. I started building web sites for friends and family. Then, I started reaching out to companies whose branding or web presence I thought could use a little facelift. Sometimes, people would bite, which helped me build up my portfolio.

I started building up my web presence and posting my work online. People started contacting me from all over the world – People from places like MTV and Marvel Comics. I was building up my portfolio by freelancing all through college.

Still, my parents were worried about me freelancing right out of college. They felt the “normal” thing to do was to have a job lined up for after college for job security. I ended up getting a traditional job, and it was a good experience. But I kept building up my website with my freelance work and I ended up being the No. 1 search result on Google for “freelance graphic designer.” I realized that with all the work that was coming in, I could quit my day job, work half the hours, and make twice the money. So, I did it.

I wanted to build a bigger team to support all the work that was coming in. There were great projects, and I hated having to turn away fun things. So, I built a team of freelance designers and launched Pixelkeet.

Who was your first customer?
My first commercial client was my family’s neighbor. He had a construction company. I did their website.

How did you fund your business in the beginning? Have you taken on any additional funding since?
The great thing about starting a business when you’re in high school is that you live with your parents and have no rent. Everything you make, you can put back into the business. At some point, it started making enough to support a team, and that’s where we are now.

Running the Business

How did you learn to run your business?
On the job. I had no formal training. I think it would have been nice to have gone to some kind of business classes. But, since I have been doing this for so long, trial and error is how I’ve learned.

What was the biggest mistake you made in your first year?
Falling into the trap of clients not paying. You do this beautiful project, you deliver the work, the client is so nice, and then there is no check. It is exhausting and demoralizing. So many people just don’t want to pay for stuff and they think that’s totally fine!

You do that once, and you learn that you need to take half or all of the payment up front, depending on the size of the project. You start having contracts in place. You never just work on a handshake or a verbal agreement. You work on clear terms that have been printed and signed and confirmed by both parties.

What’s the smartest thing you did in the first year?
In the past year, I started reducing the amount of interaction that my team has to have with each client by making things automated. People need to fill out an online form describing what they want so we can then give then an estimate, as apposed to one of my team being on the phone for an hour and a half with a prospective client who hasn’t really defined their own idea.

What’s the most rewarding thing about running your own business?
I had a traditional day job for two years. It was soul-crushing. The idea of sitting in the same place, like in a cave, for 8+ hours a day, day in and day out, doesn’t make any sense to a creative. Creatives are supposed to be coming up with new things all the time. How is sticking them in a static, unchanging, uncreative environment helping to encourage that?

By going freelance, you can work on your own terms in whatever place inspires you on whatever schedule you want. And you can only take on the clients who you think are inspiring.

The best part about running my own business is the ability to control the culture and build a company where I can make sure that the people working there are happy with their job and feeling fulfilled in some way – That they’re actually happy to be there and not just punching in.

What’s the most difficult/challenging thing about running your own business?
When you’re first starting out, it demands everything from you. There are so many things that never occurred to me to worry about. So much paperwork and legal formations and schedules to keep track of and things to set up – You really have to juggle all the different things and wear all the hats. You have to do the legal research, the accounting, the hiring and a lot of the projects. How are you supposed to do all of that without it taking up your entire life?!

What’s the most surprising thing about running your own business?
I’m surprised at how it’s changed me. I used to be so afraid to be confrontational, or talk about bad news, or ask for money, or fire someone. These are all difficult things that made me uncomfortable. Now, after years of doing this, I think I handle all of those situations pretty well! I accept them as a part of doing business. The hard things are actually the first things I talk about now, because it’s important to me that everyone’s on the same page.

What business owner or entrepreneur do you admire most? Who is your role model?
I am a co-founder of another company, CrowdMed, which is a project to crowd source medical diagnoses. My co-founder, Jared Heyman, is someone I admire. We are working on this crazy project that’s never been done before. It’s a whole change in the way people normally think about the medical industry. It’s a serious topic. Running the business is hard! We’re out there pulling all-nighters trying to get things out. But, Jared has this life balance where he’ll do what needs to get done with the business, but he still makes sure to have a lot of fun. I appreciate that and I want to make sure that I maintain that so I’m not all business.

What I’ve Learned

What advice do you have for others starting their own business?
Contracts! It doesn’t matter who it is – It could be your buddy or someone you think you’re on really good terms with. It’s just better to have a contract because everyone knows what’s going to happen at what time and there’s no confusion. Discuss everything up front, agree to everything up front, and then have it written and signed!

What do you wish you had known before starting your business?
Everything! I wish that it would have occurred to me to talk to someone who’d done this before. I wish I would have known to seek out the advice of a mentor so I could have known what to expect and what I was getting into.

About the Author — Ashley Sweren is a freelance marketing writer and editor. She owns her own small business, Firework Writing, located in San Jose, California.