Pippin Williamson

A few days ago I posted my 2014 in review post that detailed revenue and expenses for 2014. In short, it detailed some pretty darn good numbers and showed a greater than 2x growth from 2013. One could easily look at those numbers and think, "damn, he's got it good", and to be frank, yes, things are going very well for me, but they didn't happen overnight. Getting to $780,000 in annual revenue has been a long journey with more failures than successes. To count all of the contributing factors that helped me reach this point would be impossible, but I would like to talk about one: relinquishing control.

My 2014 in review post, and some from other WordPress business owners, were quickly linked to from several blogs. Two of those blogs made very similar points. To put them in my own words, they said:

You can look at a business's success and be jealous or envious of their numbers, but what you often don't see is everything that happened in the background to achieve those results.

One particular aspect of my backstory that I feel has been largely responsible for achieving numbers like $780,000 in annual revenue is how I have continually given up more and more control of various aspects of the business.

I began building my business while I was a sophomore in college at the University of Kansas. Since that time more than six years ago, I have personally handled every aspect of the business. And yes I mean everything. Development, planning, marketing, design, book keeping, taxes, etc. Everything. For a long time I was truly a one-man-team.

At first I loved doing everything myself. I was in total control. It felt great to rarely, if ever, have to rely on someone else to move a project forward. If the announcement post wasn't done, I only had to kick myself in the rear and say "get a move on" instead of reaching out to someone else to see what the hold up was. When it came to filing taxes, I never had to worry about how long it would take an accountant to finish them. When I wanted to get a plugin update pushed out, I only had to push the big red button myself.

It was awesome because I was 100% accountable for everything. That meant I could move at 100 MPH and get things done with great speed.

That younger version of myself was delusional. What I had failed to understand was the tremendous value that working with other people can provide, both to your mental health and your business numbers.

Two and a half years ago, when I first launched Easy Digital Downloads, I started to get interested in actively working with other people within the WordPress community to build better and better products. The first step I took towards working with others was to ask for development help with EDD. I had no idea at the time how much of an impact that little blog post would have on my future working relationships.

When I first asked for help, I was still a one man team. There were a few contractors that I worked with occasionally, but no one that would have been considered a team mate. Little did I know that blog post would be the start of one of many great working relationships.

Learning to manage a team of people when you have worked as a one man show for so long is difficult. Exceptionally difficult. With a team, it's crucially important that each person's opinions and skills are valued, and that they feel valued. To have a strong team, the team members must feel empowered in their position on the team. Building an empowered team is hard because it means relinquishing control. If you have ever led a one person team, you will likely know exactly what I mean.

Giving up control of aspects of your business is one of the most challenging, yet rewarding things a business owner can do.

One of the first pieces of total control I gave up was customer support. Since day one I had always done all of the customer support. Even to this day I do a significant amount of customer support, but early on I did all of it. Learning to give up that control and allow someone else to help manage the support queues was mentally exhausting. I kept saying things like "what if they screw up?", "What if they don't know the answer? That will reflect back on me!". Giving up complete control on support, however, was one of the most freeing moves I've ever made. It allowed me to work on growing the business, instead of focusing on keeping our heads barely above water.

The second major piece of control I relinquished was book keeping and taxes. Unless you are an accountant or just love numbers, it's unlikely that you are too attached to running the books and filing taxes for your business. I didn't ever love it, but I knew it was a part of running the business, so I did it. I always did it myself because it just made sense. I already did everything else, why not books and taxes?

Hiring an accountant and a CPA are two of the best moves I've made in the last two years. The mountainous weight that was lifted from my shoulders simply by no longer needing to worry myself with filing taxes was amazing. Early on I thought "it's cheaper to do it myself". If only I knew how wrong I was. After I got the first bill from my accountant, I literally laughed out loud. Why? Not because she was cheap, oh no. On the contrary, her bill was actually pretty high because she had to work through the mess I had made. I laughed because it occurred to me suddenly just how much money she was saving the business. By shifting the book keeping to someone else (someone who was far, far more knowledgeable about it than I), I found myself with a lot more time to focus on building and growing the business. That allowed me to more than double the business since she came on as the book keeper.

There is one more aspect of control I'd like to talk about briefly, and that's development. I am a developer. I love code. If I could spend all day writing code, I'd be thrilled. Over the last two years, I have, however, gradually given up more and more of the development responsibility of my projects. With Easy Digital Downloads, I gave up significant control when I chose to allow 3rd party developers to sell their extensions on my site and I gave up even more control when I gave Sean Davis the role of support manager. With AffiliateWP, I gave up the site development and design to Andrew. I won't deny it: giving him creative ownership of the site is 90% or more the reason AffiliateWP has done so well this year.

Yesterday I gave up my position as the sole lead developer for Easy Digital Downloads. I hired Chris Klosowski as a co-lead developer for the plugin and as co-lead developer, he has the power to make development decisions without me.

Andrew did amazing things with AffiliateWP by being empowered to do so.

Chris is already doing amazing things with EDD by being empowered to do so.

Sean has done amazing things with EDD support and themes by being empowered to do so.

Over the last two years, my team has grown from me, myself, and I to a team of four full time employees and three very active part-time staff. By growing and empowering the team, the business has more than doubled two years in a row. From 2012 to 2014, the business grew more than 480%. That only happened by relinquishing control and empowering others.

I'll end with a superb quote from Cory Miller of iThemes that comes from an African proverb:

If you want to go fast, go alone.
If you want to go far, go together.

Pippin Williamson

About Pippin Williamson

Founder and Managing Director of Sandhills Development.


  1. Pippin Williamson

    First, congrats on scaling successfully with a team.

    Thanks for this. What you and others (Thomas Griffin) have been writing lately has been an inspiration to me. I am hyper-independent. I am also stretched thinner than ever. I see two options: 1) Help less people or 2) Take the advice from that quote that you and others have proven.

    It’s nice to have examples to follow.

    1. Pippin Williamson

      I used to be adamantly opposed to not doing everything myself. In retrospect I can say that getting rid of that opinion has helped me in so many ways.

  2. Pippin Williamson

    Well said Pippin, congrats and best of luck to you in 2015… many of the things you said I can relate to very well and is another reason you’re one of my favorite devs… Very happy to hear things are going good

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  4. Pippin Williamson

    Are you worried about (or have you planned for) EDD not growing as much or less and revenue potentially dropping and having to go back to doing it all yourself again?

    1. Pippin Williamson

      Oh yes, definitely. That’s actually one of the reasons for bringing more people on. With more people to handle the load, it’s actually much easier to notice and act to reverse downwards trends if they begin to show themselves.

  5. Pippin Williamson

    Learning when and how to give up control is both one of the hardest, and most valuable lessons I think any project-lead can learn.

    There’s good things ahead for EDD, AWP, and the rest!

  6. Pippin Williamson

    Your achievements are very inspirational to so many of us. Can I say something? You have excellent way of teaching that helped built SMS gateway for various clients to have on their website to communicate with their customers. That was my number one Plugin, without your tutorials I wouldn’t have been able to build this . What you do has impact on other people’s lives like me, you have excellent way of teaching and one thing you need to look at is building educational site and monetise it. I have subscription for other mainly WordPress learning sites but your style of ground up teaching has helped me learn a lot. Than you mate

    1. Pippin Williamson
  7. Pippin Williamson

    I completely agree. But one thing I think I struggle with is the financial part. I can’t afford help. I’ve hired some part time people which I thought would work well only to literally have to redo all their work which ultimate cost me money and time. I have a full time design and dev business and a premium plugin on the side (which I would live to focus all my attention as clients are a drag). But financially I can’t justify paying anyone to help with support or development (for either the client side or plugin side). I feel like I will be stuck in Solotown the rest of my career as much as I agree with the quote and am ready to embrace it.

    1. Pippin Williamson

      Don’t worry, Derek, you will get there! I spent 5+ years as a one-man team.

      I’ve enjoyed watching your work over the last year or so and can’t wait to see how you continue to grow.

      1. Pippin Williamson
    2. Pippin Williamson

      You will get there 🙂

      One piece of advice that I received ( from I forget who now) was to hire earlier than I thought I was able. If you have a job that pays the bills and then you have a side project that you hope to onetime take the place of the current job, bring someone on to help build the side project. One good way to do that is to split all revenue between both parties, that easy both people have a good incentive to work hard at improving the product.

      You will be able to grow faster by splitting the work up than doing it all yourself.

      1. Pippin Williamson

        Going to slightly hijack this comment thread… Any developers reading this let me know if interested in discussing an opportunity. If you’re reading this site and still reading this then you are likely a good person to talk with.

        (Feel free to delete this Pippin, I would completely understand)

  8. Pippin Williamson

    This has always been a massive struggle for me, and I think it’s harder for me now than it’s ever been. Mainly because I’ve made some mistakes with people I’ve hired in the past.

    My core team right now is amazing, and because of some annoying past experiences, I’m very hesitant to mess up the chemistry we have now, so I have a tendency to over-analyze potential new hires, or set the my expectations too high with folks that we’re have doing a trial with us.

    It’s a dangerous place to be. It ends up costing us a lot of time and money and of course creates awkward relationships with the people who lose the opportunity to work with us.

    So I guess my question for you is, have you ever hired people who totally blew it in the past? And if so, how did you avoid approaching your next hire with skepticism? And if not, how did you find all the best people? 🙂

    1. Pippin Williamson

      I have not yet, thankfully, had the experience of hiring a full time employee that bombed, but I have had bad experience with part time contractors.

      While I’m sure it’s different for everyone, I think following a system where all fulltime employees start out as part time contractors and then move to a fulltime position works well. It helps everyone get used to each other and better insulates everyone involved from really bad experiences.

  9. Pippin Williamson

    I can relate it with what I have had been doing for last 5 years or so. Right now in process of building up a team and YES it is exceptionally hard to team up with right people and manage them.

  10. Pippin Williamson
  11. Pippin Williamson

    Thanks for sharing these insights Pippin!

    Question: had you known what you now know, what would you change in the way you started to work solo and when you bring more people onboard?

    1. Pippin Williamson
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  13. Pippin Williamson

    This kind of success is really inspiring to me. It’s probably the only thing spurring me on at the moment.

    I’ve been developing my plugin (Easing Slider) for 3/4 years now solely, and I’ve watched it die slowly as I fell out of love with it. Personally, I found the loneliness of being a jack of all trades the hardest to deal with, and still do.

    Constantly I’m going around in circles in my head, “should I do this”, “should I change that”, etc. Not having anyone to feedback off is mentally exhausting.

    Working ridiculous hours to little return is hard too. I know the hard work will pay off, but some days it’s extremely difficult to remind yourself. Having complete faith in yourself and the decisions you make is difficult on overtired days.

    This week, I’ve just changed the business model from freemium to paid extensions. In opening up my core offering, I’m letting other people in to what I’ve worked on alone for so long. It’s hard, but in doing so I’d hope it’ll open many more doors. Yes, I’ll be cash strapped for a while the business is rebuilt, but in the long run it will provide much larger opportunities. Still, it’s terrifying. It’s nice to know I’m not the only one.

    Keep at it Pippin, I hope it continues to grow. Gives us much smaller outfits something to aspire to and keep going! 🙂

    1. Pippin Williamson

      These sentiments feel especially familiar to me. You are definitely not alone.

      I wish you the best of luck with the adjustment to the business model and hope it works out well for you!

  14. Pippin Williamson

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