A little over a year ago, I was the chief technologist at Dyn, the fastest growing private company in New Hampshire with an internet performance product suite that is changing how companies connect to their end-users. Yet after years of helping the company grow to more than 400 employees on three continents, I decided to leave to found my own startup, Adored.
Yep, some people thought I was crazy. But I wasn’t one of them. I know myself — I was itching to strike out on my own but was afraid to make the change. It isn’t easy to tell your spouse you’re walking away from a plum assignment to start something that might fail. But what kind of entrepreneurs would we be if we liked easy things?
Luckily, there are a few questions you can ask yourself and steps you can take to ensure you’re making the right decision and setting yourself up for success.
Align Your Passion With How You Spend Your Time
There are two things you should always look for in a job: 1) the ability to be passionate about what you’re doing and 2) the ability to work with great people. The alignment of these two things is crucial. You can be working with the greatest people in the world, as I felt privileged to at Dyn, but if you’re not excited to jump out of bed each morning and attack the work day with vigor, it’s a sign that your personal passion and how you’re spending your time are out of alignment. After seven years at Dyn, my fire had dimmed.
At first, I was disappointed in myself: Why had I lost my personal passion for the work I was doing? I had lived and breathed the company for years and I still believed in its vision and its mission. What happened? Had I changed as a person? Then I came to an important realization. I hadn’t changed. The size and scale of the company had changed.
Differentiate Early-Stage Startups and Growth Companies
When we think about the end of any employer-employee relationship, we immediately think that the employee failed to perform and so they were let go. The truth of the matter is that not every stage of a company is perfect for everyone. There is a big difference between an early-stage startup and a growth company.
A growth company is about maximizing scale, which means maximizing repeatability, which means building and evolving processes. It’s pretty clear to me, and just about everyone I know, that I’m not a “process person.” At a growth company, there are more “knowns” than “unknowns.”
On the other hand, an early-stage company is about finding alignment between a customer’s pain point, a solution to the pain and the messaging and pricing for delivering that solution. At an early-stage startup, there are more “unknowns” than “knowns,” and I’ve learned enough about myself to know that I get the greatest high from working in a sea of unknowns. The thrill of the risk of failure is oddly exhilarating.
Neither a startup or a growth company is better than the other, and both provide intense and rewarding challenges. I believe that people are naturally suited to a type of environment, and when I came to the realization that I was a startup guy, it made my decision easier. But even an easy decision can be the wrong one. Fortunately, as a result of some great mentorship, I had a plan to make it the right one.
Listen to Your Mentors
While the decision to start your own company is never easy, especially when you’re older and have life’s responsibilities, having great mentorship makes it possible to successfully make the leap.
I was very fortunate to have built a strong network of mentors, one of whom had left his co-founding role as CTO of a public company right as I was beginning to feel a lack of passion alignment. I asked him how he successfully made the transition, ensured his company’s success and maintained strong relationships while shifting his pursuits in other directions.
The simple answer: he started the conversation a year before he left.
It takes time to do this right. You have to first invent yourself out of a job (which you should be doing anyway). Then, you need to give clarity to customers and partners. After, you need to allow some buffer time in case something comes up. To do this, you need to be in an environment that allows healthy dialogue and promotes the best for its employees. I was fortunate to have that atmosphere at Dyn, and I am working to create that now at Adored.
Of course, the funny thing is that someday I may be faced with an interesting dilemma: what does life look like when the new early-stage company becomes the next growth company? Truth be told, I’m not 100 percent sure as I haven’t seen that journey yet firsthand. I wonder if I will I feel differently as the CEO of a growth company. Whatever happens, I am confident that if it’s not right, I have the right network of advisors and mentors to bring me to that conclusion and prepare a transition.
Of course, that situation is still years down the road. Plenty of unknowns yet to be solved. And tonight, I put my head to the pillow, excited for the early-stage journey that awaits me again tomorrow morning.