How It Feels to Leave a Company You Started

You never think you’ll leave a business you start. Never. The thought doesn’t even cross your mind. You’re dialed in, living and breathing your venture day after day, fueled by your passion and a vision for what what the future should look like. I had 6 amazing years with Take the Interview (“TTI”), an HR tech startup I co-founded with Danielle Weinblatt. But alas, I’ve recently said goodbye 👋 to all our amazing employees, clients, mentors, and investors. It’s a bittersweet season to say the least, as I close one chapter and start a new one. Indulge me for a moment while I share a few of the things I’ve learned along the way and why I ultimately decided to leave TTI.

Let’s do this. 💪

Starting a business is a truly transformational experience — it forces you out of your comfort zone and pushes you to work each and every day on becoming better than you were the day before. I learned so much about myself throughout the process — my strengths, weaknesses, and which activities give me energy and which zap it from me. As our startup has grown from the two of us to a team of nearly 50, the needs of the business have constantly evolved. You are forced to adapt to these changing needs or risk holding the business back. And so I learned to never get comfortable in my role and to constantly reflect on how I could best be serving the business. I was always a little uncomfortable, wearing new hats and learning on the fly.

It sounds exhausting, but it was a blast.

Over time, as our business has grown, I’ve realized I really love the early challenges we faced—getting the venture off the ground, spending time deeply understanding the problems our customers face, finding a viable business model, and driving towards profitability. I have fun creating something from nothing, spending time with clients, hacking together processes for various areas of the business, and then hiring great people much smarter than myself to come in and take their respective areas of the business to the next level. I love pulling together passionate people around new ideas to birth something new into the world.

As you hit each new milestone in a startup, there becomes less and less opportunity for these types of activities. I love the question Steve Job asked himself every morning:

“If today were the last day of my life, would I want to do what I am about to do today.”

For too many days, I got up excited about who I was working with, but not about the types of problems I was solving. TTI has changed. I have changed. I like to think we made each other better. When I stepped back and thought about the needs of the business and how I could maximize my impact, it became clear to me that hiring my replacement was the right move for me and the business. I’ll still be involved in TTI (as a shareholder and advisor), and I’m so excited about where the business is going — I just won’t be involved day-t0-day any longer.

I’ve loved my time with TTI and can’t begin to express how grateful I am to all the people that have been a part of getting us to where we are today (and the exciting places we have yet to go! 🚀). I’ve learned so much and worked alongside so many wonderful people over the years, and I am truly grateful to them all. I wouldn’t feel comfortable stepping away without such an amazing team in place. A huge ‘thank you’ to Danielle for being an amazing partner from the beginning. I learned a lot from her and will be forever grateful. And to all our clients, investors, and advisors — you guys rock and I’m better for having been mentored, coached, pushed, and encouraged by you all.

So what’s next?

During this season of change, my wife, Kristen, and I have decided to uproot our lives in NYC and relocate to ATL, the city we are both from and excited to call home again. Atlanta has completely changed in the 6 years we’ve been gone, and we’re excited to invest in our new community and rediscover the city.

So for now, I’m taking some time off, getting settled in Atlanta, meeting interesting people doing cool things, and working on a few projects that may become a new venture one of these days. I’m spending as much time as possible with my wife and 6-month old, and freeing up as much space as possible to write, read, meditate, reflect, pray, cook, create music, and invest deeply in my new community.

Moving slower is an unfamiliar pace for me, and I can’t pretend that there aren’t days where I feel I’m being unproductive or being left behind. But I’m finding that doing less can sometimes teach you more than having a packed schedule or completed checklist.

In the stillness, with an empty calendar and nothing but time, you’re forced to confront your demons, come to terms with your short-comings, and reflect on what’s most important in your life.

I’m excited to take all I’ve learned on this incredible journey and apply it towards something new. And I look forward to all the learning left to be done. What’s next? Time shall tell. 😋

For updates on my journey and what I’m working on next, subscribe below.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store