Why I’m Leaving Compass

Why I’m Leaving Compass

June 1, 2017  |  Taylor Sundali

I spent the majority of Christmas Eve 2016 wrestling with Compass’s accounting software, trying to reconcile our books for the past year. Afterwards, I went for a long walk.

Center City Philadelphia isn’t a magnet for holiday travel. More people leave the city than come to it, so I had the streets largely to myself. It was a perfect environment for reflection. During that walk, I realized that I needed to tell my co founders, Matt and Mike, that I couldn’t see myself at Compass in the long term.

Thinking about leaving Compass – the company I founded and poured hours of my youth into – felt hard and unnatural, especially when considering the potential upside of the company. During this walk, and in the many months beforehand, I looked at Compass as a massive goldmine that we had discovered, but we just needed the right flavor of company to tap. Every day, it was easy to look past personal problems when considering the potential Compass has to offer.

Though as time wore on, a voice in my head – the same one that reminds you of deathbed hypotheticals and personal happiness goals – kept getting louder and louder. It was clear that my life would be much better if I left, even considering the opportunity that was in front of me.

A few disclaimers…

Firstly, the experience of working closely with Mike Wilner, Matt Fulton, and every Compass team member present and past was life changing. It’s been a transformative journey, and all the value I got from being a part of the company formation will undoubtedly have a dramatic impact on my life.

Secondly, I want to acknowledge how privileged I am to make the decision I’m making. I’m a well-educated, white guy who grew up with a supportive family and community. Not many people would be able to reflect on their discomforts and make such a dramatic life shift. I feel privileged to be able to do so, but also obligated to strive for a better life.

Now, let’s dig in. Like many big decisions, there wasn’t one overarching reason. There were several, all of which are very personal: Health, Lifestyle Alignment and Career Trajectory.


Many of my close friends and family will confirm: when it comes to my health I have a high standard. That high standard in mind, I’m a far cry from  what I would consider “healthy” for a 28 year old.

In the early days of Compass, I was working around the clock. This isn’t unusual for a startup, and I’ve seen many come out the other end in one piece – including both my co founders. My body, however, didn’t take to it well.

During the first year I developed carpal and cubital tunnel syndrome on both arms. Relegated to using Dragon Dictate, a dictation software that can control a computer using your voice, albeit very slowly, I spent the better part of 2015 speaking to my computer with my arms limp by my side. Even moderate amounts of computer work would have my nerves singing with pain.

The nerve issues got so bad that, in early 2016, I decided to spend an undetermined amount of time working from my hometown to resolve the issues with specialists I trust. Two months and several thousand dollars later, I was able to get one step ahead of these problems, ultimately enabling me to work again.

Just because I “put out the fire” doesn’t mean I’ve completely conquered the issue.

My hands still hurt, just not bad enough to stop working. With about 45 minutes of stretching and active range of motion exercises every morning, along with spending a large chunk of my disposable income on physical therapy, massage therapy and the like, I can keep my hands functioning. Not ideal, but it helps me get the job done.

Apart from the proactive things I must do to keep my hands functioning, I have a depressing list of things I can’t currently do because of my hand problems associated with 70 + hours of typing per week. Many of these things help keep my mind healthy – I’m somewhat addicted to endorphins – and play a major role in the second reason why I’m leaving (lifestyle alignment):

  1. Rock Climbing
  2. Nordic Skiing
  3. Yoga
  4. Paddle Boarding
  5. Swimming
  6. Weight Lifting
  7. Etc.

The gist: I’m 28, not 78, and I shouldn’t subject myself to chronic pain and a life devoid of the activities I love if I can avoid it.

Lifestyle Alignment

The lifestyle of a tech startup founder is objectively difficult. It’s especially hard when you’re in the thick of it; when the business is still struggling to find product market fit, and you’re motivated and willing to do anything in your power to make it work. The majority of Compass’s existence has been spent in trying to find product market fit.

For many, the stress levels are unsustainable; so much so that “burnout” is a common phrase tossed around, and companies like ours have to force vacation on people to make sure they get space from the office and unplug.

Even when you’re out of the office, as a co founder there is an expectation to have the company in the back of your mind. Any social gathering, any cocktail party, any event: you’re first and foremost a co founder of your startup; any other interests you may have come second.

Weekends, once a blank canvas of free time, started to change as well. It became a time to get in an extra 10 to 12 hours of work, knock out some meetings that didn’t get done during the normal workweek, and War Prep for the week ahead. “What’s War Prep?” you may ask. Basically ensuring I had plenty of groceries and clean clothes before the Monday grind started yet again.

Hell, I was spending my Christmas eve reconciling transactions, trying to get ahead during vacation. I’m sure there was a better time for this work, but I felt so behind for end-of-year activities that it genuinely felt like the best use of the spare time.

And yet, in spite of my qualms with this life, I’ve seen people thrive on it. Take Mike Wilner as an example close to the chest. Compass is comparable to “his baby”, and any time spent during its development, no matter what hour of the day, is worthwhile. I sometimes think he finds it equally stressful to not work on Compass than he does to work on it.

I’m not that type of person. I can push myself for long periods of time, but after years of it, I’m spent.

On my Christmas Eve walk, the more I thought about why I was interested in entrepreneurship, living the lifestyle of a co founder of a tech startup started to seem more and more off-putting. I want to leverage my entrepreneurial tendencies to build a lifestyle that suits me, not prioritize a company over everything else. I’m interested in entrepreneurship so I could gain financial independence alongside a great life. At the end of the day, I’d much rather be able to strike a work life balance, rather than ensuring my startup thrives at all costs.

Career Trajectory

I’m no longer interested in being a COO of an early-stage tech startup, and now is an opportune moment to make a change.

To illustrate why, I need to first describe the type of work I did as a COO. This involves understanding an important distinction reactive and proactive problem solving.

I’ll use Customer Service as a way to illustrate. At several stages in Compass’s lifetime, we had some customer service fires crop up; basically, we had some dissatisfied customers.

A customer service problem needs to be addressed in two high-level ways (at a good company at least). Firstly, the company needs to react. The company needs to address the and mitigate the customer’s problem head on. At Compass, this involved a lot of high-touch problem solving with a customer to make sure we part ways with as little brand damage as possible. The second way the problem needs to be addressed is proactive; the company needs to learn from the mistake made and proactively implement good process or product changes to ensure it doesn’t happen again.

As the COO, the far majority of my work was reactionary in nature. Reactive issues like this abound outside of customer service. Some folks thrive on that problem solving, and make happy and long-lived careers off of it, but I’m not interested in being one of them.

If I continue to operate as I have these past several years, I’ll be setting myself up for a lifetime of the same. Hell, I’ve gotten very good at reacting to problems at an early stage startup, and I fear that this is the most impressive part of my current resume. If I continue doubling down on it, I’ll forego building skillsets that lead towards a fulfilling career.

Sidenote: When “putting my co founder hat on,” I was able to do a lot more proactive problem solving; spearheading new ideas and creating my own problems to solve. I’m in love with this type of work, and suffice it to say that I’d love elements of this in my life moving forward.

Given what I now know, what does an ideal career trajectory look like from here? Honestly, I don’t yet know. What I do know is that “standing still” and continuing to operate the same way I’ve been operating is going to lead down the wrong path. I’ll take the unknown path versus the known and bleak path any day.

The Opportune Moment

My dad, wise in his years, called me the other day to point out how opportune my 20s are for making a life change; a major course-correction. I don’t have a kid, a mortgage or even a dog. I don’t have any major life responsibilities tying me down to Philly or the company. My takeaway after the call: Make a change, even if you don’t know where you’re moving towards.

Furthermore, Compass is no longer in need of a COO. We’re mid-process of a major pivot from a service-based startup to a SAAS startup. Typically, SAAS businesses don’t need operations folks until they hit, more or less, 10 team members. We currently have five. In essence, a few months from now Compass won’t have a need for me.

As of October 6th, I’ll be moving on. I’ll retain a board seat and I’ll keep in close contact with Mike and Matt about the business. I couldn’t think of a better team to leave a company with, and I can’t wait to see what the future holds for Compass.

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