Since early child hood, I have always been a do-it-myself individual. It is an attitude I attribute largely to the way my father raised me and my brother. The three of us were always working around the farm making repairs and handling new construction. We did our own plumbing, electrical work, mowing, cleaning, car maintenance, and everything else. My family was reasonably well off financially so we could have hired plumbers, electricians, mechanics, etc, if something needed built or repaired, but that just was not in our nature.

When I transitioned into running a business mid-way through college, my mentality was unchanged. I still did everything myself. Whether it was customer support, accounting, or development, I did it.

As my projects grew, in scale and ambition, I began warming up to the idea of having others involved and working along side me. Over the course of a couple of years, I gradually built up a small network of contractors and volunteers to assist with support, development, design, etc. I also hired an accountant to manage the books (do this early folks!).

One year ago today, I committed fully to the idea of working with others and hired my first full time employee, Sean Davis.

Sean had been working with me as a support contractor on Easy Digital Downloads since late spring, 2014, so we were already pretty accustomed to working together, but that’s not to say there weren’t some rough edges. I learned very quickly that there is so, so, so much more to managing a team of employees (even when there is just one) than simply writing them a paycheck each month for the work they do.

I had the pleasure opportunity to learn first hand about unemployment taxes, workers’ compensation insurance, running payroll, and so many other menial aspects of running a business that employees more people than just yourself. Tip: hire someone (even if part time) that knows more about those systems than you do. It will be well worth the cost.

It has been a year since Sean was officially signed on as an employee of Pippin’s Pages, LLC, and today he is part of a six person team. Yep, I went from 1 to six employees in less than a year.

Today, the employees of Pippin’s Pages, LLC, consists of:

  • Pippin Williamson (me), Owner
  • Sean Davis, support, design and development for Easy Digital Downloads
  • Andrew Munro, co-founder, support and development for AffiliateWP
  • Chris Klosowski, co-lead developer for Easy Digital Downloads
  • Topher DeRosia, documentation for Easy Digital Downloads
  • John Parris, support and development for Easy Digital Downloads

The six of us make up the employees of Pippin’s Pages, LLC, but there are an additional 6 contractors that contribute development, support, and other services to the company projects on a frequent basis.

If you had asked me two years ago if I wanted to run a multi-person team, I probably would have shrugged and said “probably not”. Today, I can tell without a shred of doubt that bringing on the five individuals above is one of the best decisions I’ve ever made for the success and well being of my company.

Nine months ago, I wrote on this subject and described how the projects have grown far more by bringing on the right people than they ever could have with me alone. That fact has been reaffirmed in my mind over and over again in the last 12 months.

I am truly honored and humbled to have Sean, Andrew, Chris, Topher, and John working with me. They have helped me grow beyond my own capacity and achieve so much more together. To them, and everyone else who contributes big or small, I am eternally grateful. I am still not sure why they put up with me.

  1. Sean Davis

    Thank you for having me! You’ve got a great squad for sure. Even though it’s been a fun ride so far, I’m crazy excited to see what happens over the next few years.

  2. Ahmad Awais

    I couldn’t agree more on not working alone. I see the team has grown to a decent number in just one year.

  3. Jan

    Congrats! That’s quite an accomplishment!

  4. Matt Vincik

    Excellent job Pippin! I was in business for nearly 6 years before I brought on my first co-worker. Going on year 13 now and we are at 9. Still small but I can completely relate to the healthy growth as much of our own growth has come in the past 2 years… and… we use EDD and the licensing plugins to make it all happen!

    Cheers to you and your team! I hope you all have many years of success in the future, and I am sure, without a doubt, that you all will!


  5. Drew Jaynes

    Nice work, Pippin! You definitely seem to be going about it the right way.

  6. Justin Tucker

    All that in a year! Job well done. Here’s to year two.

  7. Scott

    Good work! An idea for a follow up post, I’d love to hear about your process for hiring developers, even if it is just as contractors. Hell, would be even better to hear about it on your podcast.

    • Pippin

      Thanks for the suggestion, I’ll keep that in mind!

  8. Carolyn

    People who are willing to put in the hard work themselves are often the best bosses, because being the leader is a job in itself – it’s definitely not for lazy people! 🙂 Congratulations on your continued success, Pippin.

  9. Dave Bloom

    Big Pip-pin, spendin cheese. The right way. Nice job dude.


  10. Yudhistira Mauris

    Very inspiring post Pippin! I am also eager to read your hiring and business development process.

  11. Ahmed

    Congs. Inspiring!!

  12. Aditya

    I have been a fan of the simplicity of Pippin plugins and EDD in particular. I recently had the pleasure of meeting Topher in Pune, India. I also love the perspective Sean Davis brings through via his posts and social media quips. You sure hire very good people. 🙂

  13. Barry Kooij

    Congrats, Pippin! It’s great to see your company grow and how you found all these great people to work with. I met most of the crew in Vegas and loved hanging out with you all.

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