Getting Paid to Assess Tech
October 9, 2017
Is It Time to Upgrade to a Modern Technology Stack?
October 19, 2017

Why I Quit Being My Own Boss

As many of my friends and colleagues know, for almost a decade I was my own boss. I ran a successful consulting business (Pongworks Consulting, formerly Adalyze Technologies) that had over $5M in revenue since the day I started it and over $3M in just the last 3 years. While it took me a few years to make it profitable, once we had a footing I was making good money and treating my family to a great life (and probably too many Disney Cruises). Now, I no longer own that business – I gave it all up to work for someone else’s consulting business – and I and beyond happy that I made that decision.

For today, I am not going to go too far back into the history of my consulting business and all the side businesses I spun out of it – that will be a story for MANY MANY more blog posts. I will just give a little back story. A little over 2 years ago, my business took on a rather large project to build a revenue cycle management application for the healthcare industry. We were given a lot of money (cannot disclose the details), and over the next 2 years we built a very solid product. People in the industry that have seen it considered it ground breaking and called it one of the most modern looking healthcare application out there. Unfortunately, the company we built it for was going through many changes and decided it was too risky at that time to fully implement the new system (they went back to an ugly old RCM system that they could claim was stable to satisfy their risk-adverse parent company). So, now I am sitting here with an awesome RCM system, a rather large development team that was dedicated to the project, and nothing really new to work on. This is one of the worst problems a consulting business could have.

Enter one of my oldest clients. They were pivoting from one healthcare product to a new service model and needed a good RCM system to run their back end. We struck a deal selling the product and the entire development team (essentially the entire business) to my client. It was a decent deal for me. I was given equity in the new business, the CTO position, and a spot on their 3 man executive management team. It was fun for a while – we acted like a startup, spent many hours trying to create processes and procedures in a very young healthcare business, and continued to innovate on the RCM product by tailoring it to the specific healthcare application. I was…happy – but not 100%.

Then, one day, a recruiter sent me a job requisition for a technology expert to focus on evaluating companies that were in the process of being acquired by private equity and other similar firms. He wanted to know if anyone in my large list of connections would be interested. I responded pretty quickly with a “Yes, ME!” Oddly enough, this would be a dream job for me.

During my years running my own business I spent a lot of time working with early stage companies and startups helping them grow. I loved that part of my job. I would frequently volunteer my spare time to mentor post college students that wanted to be an entrepreneur and help them understand how they could take their idea and make a business out of it. Now, someone was going to pay me to evaluate business (albeit more established than the startups I worked with previously) and recommend to the buyers if what I saw was good, bad, or ugly. Not only do I get paid to do that, but I get to start down the road towards my dream of one day starting my own venture capital firm. Having years of experience in my own business is great, but being paid by a well-respected consulting firm to evaluate tech businesses for some of the biggest and best private equity firms gives me an extra notch on my belt towards my end game.

You might think by reading that last paragraph that this is only a short term job. I cannot comment at this time. I might have so much fun here (like I am so far) and never want to leave them. After a few years, they might decide they want to start their own VC arm and ask me to be a part of it – and I would jump at that chance (btw, if anyone from my company is reading this – I am serious – if you want to move into building a VC arm please give me a ring). Who knows what the future will hold, but I am happy and enjoying every day.

Oh – and for those that run their own business, I no longer have to deal with accounting, legal, finance, hr, logistics, and all those other parts of running my own business. A side benefit!

For those wondering, I now work for West Monroe Partners as a Senior Architect.  It may not sound like the position a former business owner and executive would move into, but I can assure you – the senior architects I work with are all brilliant individuals who all come from the same background as myself.  Our team that specializes on technology due diligence makes up some of the best and brightest business and technology minds you will ever find.  I am proud to be grouped with them.


  1. Kevin McCarty says:

    Congrats Gary, glad to have you so fired up to be on our world class tech diligence team!

  2. Thanks. Very good stuff!

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  6. AlinaNeurotruff says:

    Great post!
    Respect the author!

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