Last week, I left a great team and a great job at a great company.
Before joining CrossChx a year ago, I was a very different dude. Fresh off of a 2-year exit with our startup, Tixers, I was burned out and questioning whether I was cut out for a life of entrepreneurship.
Alex (Burkhart) and I learned a ton from each other and from the experience of building Tixers – but our headcount never exceeded three of us full time.
What’s more, our team was always completely distributed between Covington, Cincinnati, and Columbus. Working remotely is an incredible perk – until it isn’t. There is certainly something to be said about working alongside a team.
I emailed one of my mentors to talk about my next move, and he pressed the importance of continuing to learn without starting something half-assed for the sake of maintaining my identity as a “founder.”
“I think there are a few things to consider. The first is – can you *find* an environment that would give you lots of learning experience.
It’s not suggesting for a minute that other places aren’t great – they are. I’m saying that going to another small startup is going to remind you of what you already know, probably not teach you what the “next level” looks like.
The other part that I’d point out is that you sorta need to be around folks who don’t think Columbus is the end all/be all. I’m not saying people who don’t love Columbus. I’m saying people who love Columbus but also realize that the big game isn’t being played solely here.”
Focus on learning
I felt that my mentor’s advice made completely clear what I had trouble articulating. Without an idea of my own that I was passionate about, it was time to go back to Startup University and learn from someone else.
Shortly thereafter, I reached out to CrossChx because I really respected the CEO and senior leadership. For days I asked them a barrage of questions regarding company culture, vision, and styles of leadership. After we passed each others’ sniff test, I joined the team in June 2016.
One evening soon after joining CrossChx, I walked from my new studio apartment to Northstar Cafe with a notebook. As I waited on my Thai burrito, I wrote down my learning objectives for my time at the company. I organized them into 5 categories with several goals in each:
ex: How do I lead a full engineering team and project timelines?
2. Company culture
ex: How do I set company vision?
ex: What processes need to exist for a company this size?
ex: How do processes/pipelines/sales cycles work?
5. Healthcare industry
ex: What problems exist?
For the next several months, I wore many hats (as I enjoy doing). I spent weeks driving to doctors’ offices and speaking with hundreds of doctors and office managers. I collected and synthesized the data required for office paperwork. At one point, I led a team of 8 regional sales managers while also fulfilling the role of a product manager with a 7-man engineering team.
With the pace at which CrossChx moves, I had the opportunity to learn a lot very quickly.
As we learned more about the market, our organization changed and evolved. Our products evolved, and new products were built. My role and team changed over time, and I grew along with it. I am proud of the work we did.
Considering my interests
In April, I was asked to take on a different role and realized I was at an inflection point. I needed to consider whether this new role was something I actually wanted to take on. Ultimately, I decided that it wasn’t.
As stated earlier, I was at CrossChx to learn and make an impact in Columbus. I revisited my learning objectives, was pleased to see progress made on most of them, and realized that this new role wouldn’t push towards the delta.
But for all the things I gained at CrossChx, there was something I truly missed about my time with Tixers: the autonomy and schedule flexibility. I missed having agency over my own time.
Three months ago, I wouldn’t have been as comfortable having that conversation with myself or truly understanding what was important to me. For that, I give all the credit in the world to Chris McAlister and his coaching. Over 12 weeks and a bunch of pretty intense introspection, I gained an understanding of my identity that I didn’t even realize I lacked.
I have an infinite number of interests and I can get jazzed about basically anything. But at the end of the day, I truly care about one thing: connecting with people.
There is nothing I enjoy more than talking to and working with individuals who are really into their work. It’s contagious, it inspires, and it motivates.
Since the beginning of March, I’ve started indulging my creative compulsions by writing every day. It’s so gratifying to create something, put it out into the world, see people connect with it, and not need any permission to do so.
Chapter III: Unreal Collective
I’ve now experienced startup to acquisition for a small seed startup, growth stage for a much larger venture-backed startup, and watched from afar as friends and acquaintances build their lives and businesses.
After recognizing what is important to me (creating, controlling my schedule, and connecting with people) I only see one path: it is time for me to get back out on my own and give self-employment another shot.
On April 24, 2017, Unreal Collective was approved to conduct business in the state of Ohio.
I have several projects I’m going to build and share with the world through Unreal. And along the way, I will contract and work as a consultant with others who are doing important and unique work.
For a long time, I’ve put money on a pedestal. I thought it was the key to success, the ticket to happiness, and it was difficult to acquire.
But now I’m operating on a new theory. I believe money is abundant. By creating value and connecting to people through work that I care about, I will be just fine (really mom, I promise).
Work with me
Though I’m currently taking a much-needed “vacation” with some time off, I’ve already begun some Unreal work. Soon, you’ll have an opportunity to join Unreal Collective through mastermind groups and some independent (and weird) events. I’m excited to share them with you.
In the meantime, if you have a project or work you’re interested on collaborating on, let’s talk. I’d love to hear what you’re working on and talk about how I can help.
As I go through this journey, I’ll be sharing some pretty raw thoughts and experiences through my newsletter. I share a short snippet every morning (example). It’s where I am the most honest and transparent about what I’m learning and working through, and that’s where I send first dibs to opportunities and experiments.
I encourage you to join the community here or by entering your email below.
Special thanks to my friends, family, bosses, and coworkers for being supportive, amazing people.
CHAPTER I: Going to work with a startup
CHAPTER II: Going back to Startup University
Further reading: On Unreal Collective