Mistakes, Growth, and Staying True to Myself

Throughout my journey as an entrepreneur, I've learned some of my most valuable lessons from my mistakes. These experiences, although challenging, have shaped me as a leader and reinforced my commitment to my values.

Failing to Secure Investment: When I moved to San Francisco in 2010, I co-founded a mobile app called Crumbly with the intention of capturing the unique energy and spirit of the city. I poured my heart into the project, but I was so fixated on developing the product that I overlooked the critical need for funding. Even though people liked the app, we couldn't compete with the well-funded companies in the market, and the app eventually failed. It was a harsh lesson that taught me the vital importance of securing investment for any startup's success. This was the first time I learned this lesson, but I have bootstrapped several startups and tech initiatives since then that have fizzled out of cash. Only within the past few months have I determined "no more," no more building products without funding. And for me, that may mean no more building tech products ever again.

A Business Partnership Gone Wrong: I've also learned the hard way about the importance of aligning with partners who share my values. While leading my agency, DAG, we experienced tremendous growth and success. However, a proposed project with a bioengineered food company created a moral dilemma for me. I couldn't support a company whose practices I believed were harmful to our health, despite the potential financial gain. The impasse with my business partner led to the brutal unexpected demise of DAG.

Not Being There for My Team: During the closure of DAG, I was so overwhelmed by the situation that I failed to communicate openly with my team. I regret not being more transparent with the people who had worked so hard to build the company with me. They deserved better, they deserved to know the truth and this experience taught me a painful lesson about the importance of honesty and open communication, particularly in times of crisis.

Struggling with Operations: I've always been a visionary leader, but I've often struggled with the operational side of running a business. In the early days of DAG, I focused more on the big picture than on establishing solid operational systems. This lack of attention to detail created inefficiencies, dependencies, bad hires, missed promotions and hampered our ability to scale effectively. I've since realized that even the most creative ventures require a strong operational foundation for sustained success and that I need to be responsible and accountable for all that happens in our business.

Neglecting My Own Well-being: For years, I pushed myself relentlessly, ignoring the warning signs of burnout. This led to a diagnosis of bipolar disorder. This experience forced me to prioritize my mental health. I've learned that my well-being is essential for my success as a leader and for living a fulfilling life. And I also gained empathy for all of those that are struggling to get through their thing. One of my former teammates died by suicide after our time working together which is a heavy feeling still today. I wonder how I might have been able to support him better, while he worked for me – and after. I still feel a sense of responsibility and concern for all my former teammates and I hope they know that I am always always always here for them.

Holding onto the Past: Letting go of the past, particularly after the closure of DAG, was a significant challenge for me. I carried the weight of regret and resentment, and it prevented me from moving forward. I see that now in my pattern over the past 10 years running from one city to the next searching for DC again. It was only when I moved back to DC to face it all that I could forgive myself and those who had wronged me that I found peace and clarity. Forgiveness is a Blessing for all and should be considered swiftly and without hesitation.

These mistakes have been painful, but they've also been powerful catalysts for my personal growth and development. They've taught me to prioritize my values, to be more mindful of my mental health and those around me, and to approach challenges with greater humility and resilience.

It's a journey I continue to navigate, always striving to learn, to grow, and to use my experiences to create a more positive impact in the world.