It was 2021. One of my CEOs pinged me with a request. He asked if I would get on the phone with a prospective candidate to share my thoughts about what it would be like to work at the startup and with him in particular. “Please share my user manual,” the founder said to me. He meant it figuratively at the time, as the founder in question had no such document. But I loved the idea and gladly agreed.
When do employees share opinions freely? When do they call attention to system frailties? When do they jump into high-risk projects? When do they voice dissenting views? Answer: When they feel safe. Even the most miraculous startups face a jagged path to success — system failures, unplanned departures, unruly board members, competitive assaults, regulatory surprises, and a host of other painful but ordinary bumps in the startup road.
In 2022, a massive correction began in the startup ecosystem. Rising interest rates led to plummeting startup valuations and venture firms struggling to raise new funds. Global venture funding fell 35% between 2021 and 2022, and startup valuations dropped by an average of 34% across all stages. And it has not gotten better – in fact fast forward to the first quarter of 2024 and we have witnessed more startups go out of business than at any time this decade. Where are we now? Startups and venture firms are still learning to survive with less. Startups have restructured, prioritized profitability, lowered burn, and extended runway in hopes of deferring their next fundraise. Venture firms have slowed new investments, increased diligence, raised prices and deferred new funds.
My career began at the crossroads of design and technology, when the internet was young and it felt like everything was possible. In the last two decades I’ve been a designer, a manager, an executive. I’ve been a mentor, a coach, an advisor, an investor. I’ve founded multiple companies, had the privilege of speaking to people all over the world, and even hosted a podcast. I’ve been a vocal advocate for Design leadership and the power of walking your own path. When I look back, I can see that so much of my life has been about “doing” in order to prove my worth; this belief that I’m valuable because of the things I do, how I do them, having the right answer at the right time, etc. Along the way, I realized that BEING is what I’m most concerned with. I didn’t need to do more, I needed to trust myself, step into my own power, and lead. And in doing so, create an environment where others could do the same.
Raising early-stage capital is easy, right? It must be. It seems virtually every other tech-related article to grace my screen tells the tale of young founders armed with little more than a set of slides raising funds from one or more esteemed investors. Is it really that simple?...
It's been said time and again that people don't quit jobs; they quit managers. And why do they quit those managers? Because those managers often don’t know how to manage. And one of the most common symptoms of this affliction? The poor, ineffective, muddled, and occasionally offensive delivery of feedback...
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...
There are two separate paths to startup success. The first and far more celebrated path is the one where founders discover a novel way to address an existing problem in the world. They build a product or service, find early customers, and Voilà! A new business is born...
When you start a company, your job is to sell a vision. Then you have to go build something that (if you squint) resembles that vision...
Founded in 2015, Enjoy The Work is a San Francisco-based startup advisory firm serving startup founders and CEOs worldwide.
