Why My Start Up Failed
Fresh off a sabbatical, having neatly tied up a few year leadership role in NYC, I left with my husband, baby and dog for the Bay Area. I was so nervous, but excited to shake things up. My husband had landed his dream role at a FAANG, and though I was scared to leave everything behind, we were off and running.
I was interviewing while taking care of my daughter full-time in a city where I knew no one. The interviews were disappointing, marred by discrimination. I couldn’t believe it. “This was Silicon Valley? This is what I left everything for?”. So I talked to my best friend, who was going through something similar in NYC in her career, and out came our idea to fix the broken interview process at early stage tech companies.
I felt alive, and inspired again — especially to work with my best friend. We worked so well together. It was easy, fun, and productive.
And after my second daughter was born, I flew out to run our alpha version in a workshop filled with friends and family to get feedback. We had sales in the pipeline. And then, everything fell apart.
The end of my startup was unbelievably painful. I not only lost the company, but I also lost my best friend. And it took me a long time to fully process, and own what went wrong. Here’s some of it.
I buried resentment
I lacked the self-awareness to address what was really bothering me in my co-founder relationship. Or rather, they were feelings that sat under the surface, that I was afraid to address. It wasn’t until I entered my executive coaching program that it bubbled up, leading to a lot of tears, and frustrations. My resentment was about our personal dynamic — I felt she took the lead too much, and I wanted to be more at the helm. I resented how much energy I was putting into the company while juggling a newborn, a toddler, and a job search, and I saw it as her fault, even though I never voiced it, nor was it. This festered until I couldn’t hold it in, leading to an emotional discussion where she decided to walk away.
My heart was elsewhere
I liked the idea of addressing discrimination and bias through the interview process. I loved the methodical approach to making the candidate experience better, and I loved working with my co-founder. But my heart wasn’t in it. By the time we started the company, I had already decided to pursue coaching at the Hudson Institute, and that’s where my passion was. I say my long term career as a coach, and it was hard to be as emotionally invested in anything else.
I was afraid to sell
Pregnant, in a new city without friends or family, with my husband at work all day, I was lonely and anxious. My confidence was at an all-time low, and I hadn’t yet found a therapist. I’d uprooted my entire life in NYC and that reality was setting in. So alone, I doubted my abilities, telling myself that leaders wouldn’t take us seriously. I deferred to my co-founder to take the lead because I was afraid of rejection and afraid to put myself out there.
I was burned out
I thought my brief sabbatical in NYC had cured my burnout, but it hadn’t. I was still recovering from a big job, being a new parent, and (little did I know at the time) a life that didn’t align with what I truly wanted. Uprooting my life, starting a company, searching for a job, and doing a coaching program without adequate support was too ambitious. The exhaustion, low confidence, physical injury from pregnancy, and lack of emotional capacity made it impossible to address my feelings or have tough conversations with my co-founder until it was too late.
I have a lot of regrets about that startup, and I am still not over the loss of my best friend. But I learned so many big lessons about myself and how to do things differently. We often focus on the technical aspects of starting a company, but it’s our self-awareness, the personal and human dynamics, our ability to manage conflict directly and compassionately, that are so crucial. Today, I’m grateful to apply these lessons to my own business, and in helping my clients navigate them too.