Being a solo founder, the startup journey has been filled with wildly new challenges. As a by-product, I’m constantly soliciting feedback and advice to level-up my perspective on a myriad of topics. Certain comments during conversations, often said in passing, linger and end up serving a significant purpose later down the road, with one of the most impactful comments being from the amazing Aisha Bowe,
“Your company grows as fast as you do.”
Like most founders, over the past few months, my resolve has been tested in numerous ways, requiring deep personal growth. I’ve been asked several times to share some of my experiences and lessons learned and as the end of a decade approaches (crazy, I know), here’s one of them. Hopefully, it serves as a helpful perspective for others going through a similar experience.
Hello Darkness My Old Friend
I never really understood motivational posters until earlier this year. I would see them and think, “Why would anyone need this? Just do or be better.” Clearly, this was a short-sided perspective and up until earlier this year, I had never experienced true anxiety or depression.
There are several articles about founder depression, a couple of them being The Psychological Price of Entrepreneurship and Brad Feld’s perspective in Entrepreneurial Life Shouldn’t Be This Way–Should It? For most people whom I’ve met, they’ve only known the outgoing and driven version of Andrew Stroup, including myself. I had never crossed that threshold into anxiety or depression, but now that I have, I’ll always be aware and mindful of that line.
At the end of 2018 during the start of the Winter months in NYC, I ran into a wall. I was sleeping two hours a night, just closed our first round of fundraising, and was facing issues finding product-market fit six months into the company. The light at the end of the tunnel disappeared and I began to feel lost as my startup was so closely tied to my identity.
First Signs of Something Wrong
It was getting harder to get out of bed, multiple espressos were no longer working, and things felt off. I could sense something was wrong, but I couldn’t describe it until my close friends started describing it for me. I’d join a social gathering and put on a smile, thinking I could hide these changes, but would instead be greeted with a concerning look and a simple question,
“Are you ok?”
After recognizing there was a problem I immediately did what an engineer does, try to solve it myself. I experimented with an array of various practices and approaches. This included visiting my doctor, sleeping aids, deep-breathing techniques, meditation, exercising, CBD, and yes, even make-shift motivational posters taped to my apartment wall with statements like: “One day at a time”, “Follow the process”, and “Whether you think you can, or you think you can’t - you’re right.” However, the biggest challenge was that when grappling with depression, being solely stuck in your head trying to solve it often only makes it worse.
That’s when I sought external help and perspective. The transition back to normalcy started after I started sharing my feelings with close friends, family, and other founders. All of the conversations were deeply helpful during this journey, but one particular comment from Jonathan Wasserstrum regarding his personal experience resonated.
There is no single panacea solution, but instead, it’s about accepting the feelings exist and maintaining a balance to ensure you’re healthy so your startup can be healthy too.
About a month after that conversation and discovering various practices and routines that were helpful, I was able to find a balance of meditation, sleeping techniques, exercise, and more, which afforded me the ability to be present in personal life and as a founder for my company.
Back to Fundamentals
Over the past few months, I’ve spent a lot of my “free” time reading other people’s journies. A particular book that stood out was Scott Belsky’s, The Messy Middle. There are quite a few insightful nuggets in his book, but what I valued most was Scott’s ability to translate the hardest parts of building a company, traversing the unknown, making tough decisions without all the facts, and the personal struggles and journey as a founder.
During a catch-up coffee with a former White House colleague, Garren Givens, he reenforced the lean startup methodology of defining hypotheses, testing them, and quickly iterating. Applying this lesson across the company, we refactored everything we did to ensure it was being executed using a hypothesis-driven experimentation framework.
We tested six value propositions across ten market segments, receiving 1400+ responses to identify strong signals of product-market fit and our first customer, Harry’s. What we discovered was a critical workflow for supply chain organizations. After extreme sales and product iteration cycles, LVRG automatically tracks and manages supplier performance to drive cost-savings through accountability.
Onward and Upward
The journey is far from over and there are many more lessons to come. With a newly developed respect for those who have gone through depression and are on the startup journey, I recognize the importance of the continued personal growth required by the team and myself to directly support the growth of the company.
GIVE: If you’re reading this and going through a similar experience, know that you’re not alone. I don’t have the answers for you as that’s part of your journey; however, I will promise to be available to connect over a coffee to listen and share my perspective if helpful.
CREDIT: While not fully inclusive, I wanted to thank specific people in my life that had a significant impact during this part of my journey: Shanna McEachern, Joel Wishkovsky, Jon Stein, Matt Emerman, Gilad Rotem, Nadav Ullman, Matt Oehrlein, Elle Hong, Natalia Farhadmotamed, and most improtantly my mother.