My Entrepreneurial Journey

I remember the moment when I knew I wanted to be an entrepreneur. I was having dinner with my Dad, a business owner, and my Mom, an attorney. My Dad said, “I am making money right now as we are eating dinner. Your Mom can only make money when she is in the office billing her hourly time.” This made me realize that I needed to start a business, not work for someone else.

The next step in my realization that this was the path for me was going to business school at USC where I studied entrepreneurship. There, it was engrained in me that there was no other option. So far, the journey has been somewhat successful, but I know there is a lot I can learn. Below, I will go through each of my business ventures and tell you what I learned from each.


  • Kevin’s Powerwashing and Staining

    Business Launched: 2002

    What was It?: In high school, instead of getting a summer job, I ran my own business powerwashing and staining decks around my hometown of Santa Rosa, CA.

    Successful?: Yes, compared to a $10 /hour part time job. I was making $200 – $300 per deck, which was done every 2 days. I was my own boss and making enough to make it worthwhile.

    Biggest Lesson Learned: Create a system you can use over and over. I used a formula for estimating the price of a job. It was a certain amount per square foot of deck plus a much higher amount per square foot of railing. I could go to a prospective job, measure it out and give them a price on the spot. Having a system where I could give feedback to the customer on the spot, while keeping a guaranteed margin, gave me an advantage over the competition.

  • Flyer on a Chain

    Master-header-logoBusiness Launched: 2008

    What was It?: My first business out of college, I had no idea what I was doing or what was need to succeed. Flyer on a Chain is an alternative to real estate flyer boxes that constantly go empty. I saw a lot of real estate listings that had no flyers in the flyer box and I thought there could be an opportunity change that. Customers would upload their real estate flyers to my site. I would then print them, laminate them, and attach a swivel chain to the laminated flyer.

    Successful?: No

    Biggest Lesson Learned: Marketing, marketing, marketing. I was naive in thinking that once I had a site built and a product in place, the sales would start rolling in. It hit me like a wall that marketing was everything. It didn’t matter how good the idea or product was, it needed to get out there. I sold a couple hundred flyers, but in the end, there was not enough sales to make a living. It was time to move on.

  • Inbound Design


    Business Launched: 2009

    What is It?: A web design company, Inbound Design, that has built over 100 websites for local and national clients. Inbound Design has built WordPress sites from the beginning, back when WordPress was still in its infancy as a CMS. This is where I grew my knowledge and experience with web design. It is still active today, but it is in a transition from my full time business, to one that I am slowly phasing out.

    Successful?: Yes

    Biggest Lesson Learned: Networking can grow a business. Inbound Design was built on referrals through networking. I got myself out there and made connections that turned into business. It is worth spending the time to network and grow your business by growing relationships.

  • WP Setup 101


    Business Launched: 2012

    What was It?: In exchange for visitors using an affiliate link to signup for hosting, I would install and setup WordPress for free. I made a commission from the affiliate link while the client would get a free setup of WordPress.

    Successful?: No

    Biggest Lesson Learned: Don’t start a business with a partner you don’t trust. I started this business with someone who wanted to work with me on a business, but I didn’t trust my instincts about that person. If you don’t feel good about something in your gut, don’t proceed.

  • iPrint Pano


    Business Launched: 2012

    What was It?: I was taking a lot of panoramas with my iPhone, but I wanted a way to see them at a larger scale than on my phone. iPrint Pano was a service where customers uploaded their panoramas and we would print them at up to 48″ wide.

    Successful?: Yes

    Biggest Lesson Learned: Calculate whether or not something is worth your time before you dive in. I spent a lot of time developing a website, buying a printer, and getting processes in order without doing one simple calculation. That calculation was: quantity x price. I would have to sell hundreds and hundreds of posters to make enough money to live on – and I realized this after I had put all the work into creating the systems to do it. I sold about a hundred posters and then realized my time could be better spent.

  • wpONcall


    Business Launched: 2013

    What was It?: WordPress Support Services

    Successful?: I am making sure of it :)

    Biggest Lesson Learned: You need to make sacrifices for the greater good. I have decided to stop taking web design projects through Inbound Design to focus all of my attention on wpONcall. I want to build a more scalable business that does not rely entirely on me doing projects. I am sacrificing the income of projects for my long term goals.

That’s my entrepreneurial journey. Share yours below!

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