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In early 2017, I was feeling pretty on top of the world. I had left my role as an attorney in Google’s legal department a few years prior to take the very cold (and very naive) plunge in the entrepreneurial pool in Silicon Valley.
I ultimately founded three companies, two of which did not go as planned, but one was approaching escape velocity. One particular period stands out. I had just raised my second round of capital. The investors were all from top firms. I had the resources, traction, team and network to win. I felt unstoppable.
Until my first board meeting. As it turns out, I didn’t know how to masterfully run one of those. I had great instincts, but I hadn’t had the reps. My new fancy investors were rough on me. My goals were unclear. My financial model was weak. My hiring plan had holes. To say the least, I was rattled.
Not too long after I received a phone call from a friend and fellow founder. I shared my recent experience and his response was, “I have someone you must meet. He and his partners are my most trusted advisors.” I was skeptical. As I mentioned, I had the network already. My cap table was filled with famous investors and successful founders. More advisors did not seem like the answer. My colleague was insistent it would be worth my time.
A few days later, I met with Jonathan Lowenhar, Founding Partner at Enjoy The Work. We talked for over an hour and by the end of our first meeting, I knew I wanted to work together. His track record as an operator was unquestionable, his advice direct yet empathetic, his frameworks thoughtful, practical and pragmatic. The other partners at his firm were equally accomplished.
I became an Enjoy The Work client soon thereafter. Over the next three years we weathered nearly every storm a founder can suffer: co-founder break ups, complicated board dynamics, product launches and product pivots, bridge rounds and layoffs and navigating all of it while pregnant with my second child. But it wasn’t all pain – we also delivered a product that customers loved. We saw our revenues and industry profile grow and grow. We built such substantial value in our product and our brand that we became a sought after acquisition target. I ultimately led the company through a successful early exit in 2020.
I stayed with the acquiring company until we were acquired yet again (unconventionally, two exits to two private equity firms in a two year period). Then I took my well earned earn-out and for the first time in many, many years, I actually took time off. I spent time with my husband and young kids. I read fiction books and started playing the piano for the first time in over a decade. I went to the farmers market and cooked extravagant meals. I finally found some space to get on a plane and visit some faraway places.
But I couldn’t stay away. It wasn’t long before I started spending all of my free time with founders. Some were just coffee dates. Others were counseling sessions. And then I began angel investing with a thesis that was firmly grounded in the founder, regardless of company stage and sector. I was fortunate to have a wide network of amazing humans building cool companies, so it wasn’t hard to find the right founders to back.
Without realizing it, I had already started exploring what would come next for me professionally. But I wanted to dig deeper and be extremely thoughtful about my next move. What really lit me up inside and brought me joy? When had I been the happiest, and what were the connecting threads? Here’s where I landed.
I never set out to be a founder and growing up I didn’t dream of becoming a CEO. I aspired to be an attorney, just like my parents. Looking back, I always had entrepreneurial instincts and tendencies, and my parents both left big firm and corporate settings to start their own law firms, but we never referred to them as “entrepreneurs.” I didn’t have the correct vocabulary, it truly wasn’t part of my lexicon.
For a long time in my startup career I suffered imposter syndrome. Who was I to be a founder? A CEO? Paradoxically, being an entrepreneur has ended up being the thing I’ve done longer than anything else professionally. I’ve spent more than a decade launching, building and (eventually) exiting startups. I love it. When I think about what makes me happiest, there is nothing I love more than building businesses, brainstorming and strategizing, and being surrounded by other creative risk takers trying to build big, challenging things. I’ve worn many hats, but being part of the founder community is something that brings me tremendous pride.
There is a certain thrill that comes with a successful fundraise that is hard to explain. After you’ve pitched the same narrative enough times you become a masterful storyteller, anticipating the next question an investor will ask so easily that it’s like you can see the future. It starts to feel like an artful and well choreographed dance, one that you’re leading with ease and grace. You get the term sheet(s) and then enjoy a brief celebration once the money hits your account.
As a founder, you’ve got the vision. You’ve got some combination of grit, tenacity and courage. But sadly, there is no official playbook that teaches you how to become a great CEO. In the early days my instincts were enough. It led me to what to build. How to sell. How to recruit. But the bigger the company and more complex our offering, the more my instincts felt insufficient.
I didn’t want to just survive the job. I wanted to thrive. I wanted to be great, and that meant gaining new skills. Things I never really concerned myself with at the start of the journey. Every founder faces this conflict – the improvisation that got your company started won’t be enough to have it reach its full potential. Learning these CEO skills well will usually involve a great amount of trial and error, ideation and iteration, and making mistakes on your own dime.
For the vast majority of founders, time and money runs out before they can collect the skills they need to win. There is a faster way.
Here’s the thing entrepreneurs don’t usually discuss publicly. Although there were times on the startup rollercoaster that were really fun, my founder journey was hard. It was scary, humbling, confusing and pretty damn exhilarating all at the same time. And it was often lonely. So many times I didn’t see a path forward. And through every one of those dark times, the partners at Enjoy The Work – particularly Jonathan, Anu, Ned and Leslie – were there for me and my team. We wouldn’t have survived the pivots, the hirings, the firings, the bridge rounds without them. And they were with me every step of the way to our exit. During our work together, I learned so much.
Truth be told, I thought I knew everything about how Enjoy The Work operates and I always thought I was their favorite client. But as it turns out, there is a lot I didn’t fully understand. Like the extent of the partner collaboration that goes on behind the scenes and the mountains of experience and pattern recognition in the collective brain trust. I always figured I was special and that’s why I received such high touch service. Now I realize that I wasn’t receiving any special treatment.
The partners at Enjoy The Work have a saying: earn the right of the first call. It means being the first person the founder contacts when something goes well, but more importantly, the first phone call when something goes poorly. It means creating so much trust and safety that the founder will come to you equally whether seeking help or celebration. For the founder, there is incredible security knowing there is a deeply knowledgeable former founder always available to you who is fully safe, genuinely empathetic, deeply informed, and entirely objective. To me, this represents the antidote to the high pressure reality that is startup CEO isolation.
I consider myself a founder fan girl, a true advocate for those trying to pull off big wins and hairy, audacious goals. I’ve built my life and my career around my founder identity and community. I abhor the idea that an entrepreneur might build something interesting only to fail due to lacking certain company-building skills. Founders should not have to survive by trial and error. Thankfully, and as I experienced firsthand, they don’t have to.
After all my soul searching, I’m so excited to announce that I am joining Enjoy The Work as a General Partner! My mission is to be in service to other founders and help them make the leap to great CEO and enjoy doing it. So if you’re a good human working on a hard problem, come find me. I was in your seat not long ago, and it would be my pleasure to be part of your journey.
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Founded in 2015, Enjoy The Work is a San Francisco-based startup advisory firm serving startup founders and CEOs worldwide.
