Lessons From 5 Years in WordPress Business

2011-09-22February 2nd marked our 5th year in business. What started as moonlighting while working a full-time job and going to night school for my BA turned into a business on Groundhog’s Day in 2009.

That month was kicked off by friends who had businesses and were waiting for me to have enough time to create a nicer WordPress site for them, and I suddenly had all the time in the world to work on sites.

There have been high times and low times. This is actually a low time for us so it felt awkward to write this, BUT IT’S A MILESTONE, and I have faith it will work out. We are doing what we are meant to do, both as individuals and as a family.

Times I conceded I’d get a job if a project didn’t come in by X day and times my wife was insisting she needed to go back to work. Neither of those things came to fruition because the work always came in time.

It’s these times that make me look back at epiphanies like I had a few months ago about where we are now compared to where we thought we could be by now, 5 years ago.

Where were you FIVE YEARS ago? THREE YEARS? Are you more or less where you wanted to be “someday?” For me, I’m well beyond where I would be by now. I hit that just TWO YEARS into business when my wife quit her job. I’m actually living well into my fantasyland from five years ago.


I’ve learned a few lessons along the way that are important to remember. Remember where you came from and don’t abandon those people – and don’t get too busy to help the people who first believed in you when you were a risk. It’s a very good idea to give to the community and don’t charge for everything, but don’t go hungry because you helped a friend – business is business. Obey the Golden Rule – everyday. Believe in yourself and surround yourself with those who believe in you. Have trustworthy people you can bounce ideas off of or ask questions before making a major decision – wisdom in the counsel of many if the counselors are wise.

Stats & facts

I spent a little time and compiled some stats and facts from our first 5 years in business and in 2013:

  • 228 clients in total since 2009
  • 1,300 invoices since 2009
  • 313 invoices for site development since 2009
  • $342,000 in gross revenue since 2009
  • 4 hosts and 5 servers used since 2009
  • 4 WordCamps attended since 2009
  • 8 desk moves since 2009, including not having one
  • 4 desk moves in 2013
  • 2 WordCamps attended in 2013
  • 75 clients served in 2013
  • 24 full sites launched in 2013
  • 260 invoices in 2013 (1 per weekday)
  • 27 sites migrated to WP Engine in 2013
  • 1,654,905 visitors to all of my hosted sites LAST MONTH

Thank you all for the opportunity to serve you and serve with you. I can’t imagine doing anything else right now.

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  1. says

    Thanks for sharing this man, I just started moonlighting a few months back and have a lot to learn. It’s great to be able to learn from other peoples experiences. 5 years feels like a lifetime to me at the moment

    • says

      Moonlighting is great and annoying at the same time. I’ll admit that during our low times, I’ve considered for a few days at a time that getting a job and doing this in the evenings would be good, but I know that’s just a moment of weakness. You’ll get there and then 5 years back will seem like a lifetime ago.

  2. Little Shiva says

    Thank YOU for being so good at what you do – and responsive, phew! I love working with you.

  3. Cape Dave says

    What a truly fantastic post. Seems like great success. On all levels. All around nice job! I see we both enjoy the mac mini. I may have said that before. Getting old. Dave

    • says

      We do and you have, but that’s okay. :) I love how easy it is to move and setup with how often I move my desk, but I’ve hit on a display limitation because of the 2011 integrated graphics. TB is great if the GPU could push more pixels. Alas, I’m doing things the bootstrap way. Paying cash for my Mini server was absolutely my most rewarding purchase ever. In June it will be < $1 per day for it, too.

      • Cape Dave says

        I am practically obsessed with the mini :) A refresh is due soon (so they say) and I am really curious what it will be. Many say Iris Pro graphics. I follow Macrumors very closely :) I may even do my second podcast ever on the mini.

  4. Joel Schmidt says

    First, congrats! It takes a lot of guts to go the solo-preneur route, especially with a family. Second, your expertise and assistance with our web development projects has been nothing short of a revelation. Looking forward to a long, successful partnership! Hopefully, one day our paths will actually cross in person.

      • Joel Schmidt says

        I worked for a small animation company out of grad school; I was married just a few years with our first child on the way. After about a year, the economy turned against us, and business started drying up. We had to let go of some good people, and everyone at the mgmt/ownership level (including me) took huge pay cuts. I can’t imagine how the pressure and stress are multiplied when you’re the whole show.

  5. says

    It’s so true that we can become preoccupied with the low times and then forget from where we came. Thanks for sharing this and being vulnerable.

  6. Quincy Zikmund says

    Jesse, congrats on 5 years! This is a huge encouragement and inspiration to me. Keep up the great work, here’s to another 5.

  7. says

    Thank you Jesse for the transparency you’ve displayed here on your website. I know how hard it is to put yourself out there when people think that you have it all together. Because you wan to be an inspiration and you don’t want anyone to think that it’s impossible to achieve your goals. Because you already know that it’s possible.

    It’s amazing, even in our times of doubt and struggles that we are always thinking about other people. For me to read this article from you was very inspiring and tear jerking all at the same time.