Starting a company again after I swore I would never start one again

“Would you ever do it again? Was it worth it?“ 

I was with my mom at a family dinner a few days after we announced the sale of rideOS to Gopuff. I was exhausted, I had not had a proper night of rest in months.

“I would never do it again. And, I’m not sure if it was worth it” 

Chris and I had achieved the American dream, but I was traumatized from the battle wounds over the last years. Waking up everyday to problems you feel that you cannot handle, shouldering the burden of so many teammates, combined with the isolation of the pandemic. The constant pressure to find product market fit, the crazy pivots, the morale hit after a quarter of the team left over the course of a few months. 

Many regard me as one of the happiest and most positive people they know. But behind closed doors, my wife, close friends and family saw me go through seasons of sleepless nights, heavy anxiety, and situational depression. 

Is it pre-existing mental health issues that lead to folks becoming entrepreneurs, or the startup journey that exacerbates mental health issues? What I have learned is that it is paramount to invest in your mental health before you need it. 

If you want to be a good leader, husband, friend, child, it starts with taking care of yourself. If you do not take care of yourself, it becomes that much more difficult to take care of the people around you.

Last year, I spent the majority of my time advising startups and investing, and I slept like a baby. I reconnected with my good friend Mick Eddy, and supported him in launching an incredible venture fund and making several investments along the way. At clubs, I noticed it was my friends yawning, not me. I played pickleball for 3 hours a day, made some wonderful friends, and gave an incredible quartet performance. I explored many different things, filled with many failures and successes. My goal was to help out as many entrepreneurs as I could.

For some reason, something still felt empty. 

In December, my wife looked at me, and said “Justin, every time you talk about your career, it has you starting another startup. If you want to start a company, just go ****ing start a company”

I love my wife. She has always believed in me, and it was a similar conversation that spurred me to start rideOS. I would not be here without her encouragement and strong support. 

This time, I was hit with a wave of shock, excitement, and fear. This is indeed what I had wanted to do all along, but I was scared. I embarked upon a month-long process to revisit my trauma. Trying to find the courage to break through the fear. 

I read through all of my old journal entries. I reflected upon all of the failures, all of the most difficult situations at work. I relived the worst version of myself at home, punching walls, and getting into fights. I broke down so many times. I prayed daily to find clarity for the path ahead. This is part of the process of healing. 

Compartmentalizing your stress and darker emotions is not a sustainable way to live. You need to give yourself the space to breathe and experience the entirety of the human experience. 

At the end of this process, I was firmly convinced I was ready to start another company. The next question was who to start it with. Thankfully, Chris Blumenberg, my prior co-founder, decided to join me again on the upcoming journey. Life is all about the people you spend time with, and I am so grateful for his leadership, support and friendship through the last decade. 

There are 3 things I keep in mind as I embark on this journey: 

1. I have already succeeded, just by taking the courageous step to embark on this journey. Society measures entrepreneurship by team size, capital raised, the size of the exit. The reality is that 99% of startups will fail. The failure of the startup must be separated by the failure of the entrepreneur. There are so many things out of one’s control. This does not mean that one does not dream and shoot for the moon to build a company that can outlast yourself. But, it means that you are proud of yourself no matter the outcome. It means that you separate yourself from the comparison trap that inevitably exacerbates more severe mental health issues. 

2. Entrepreneurship is all about culture. Culture = values + people + process. If you build a great culture, it will outlast your company and products, because the people you have the privilege to lead will spread this culture to other places. To me, entrepreneurship is a lifestyle. It’s about the values you establish, it’s about the people you bring onto the team, and the process of finding product market fit. It’s about the resilience to get through the ups and down, and never giving up. Build the right team and culture, and the rest will sort itself out. 

3. Do not worry and be optimistic. Many folks often ask me where my optimism comes from. The world could be falling apart, and I’d still find the silver linings. My optimism comes from my faith in God. James 1:2-18 is my favorite passage, and these words carried me through so many of the hardships during the prior journey. Research shows that less than 8% of our worries actually come true. And, for the worries that do come true, these are often accompanied by the greatest opportunities to grow, and develop resilience. 

Onward and upward!