The CEO is the Chief Cultural Officer

Hard lessons learned from Uber's brilliant jerks

I’ve come to realize that the culture of an organization forms at the very start of the entrepreneurial journey. Founders serve as Chief Cultural Officers, and their beliefs, behaviors and values heavily influence the culture of a company, starting on day 0. 

Unfortunately, many founders are brilliant jerks - which partially explains why there are so many successful companies with toxic cultures (e.g. Tesla, Citadel). Of course, there are also successful businesses with CEOs that have built inclusive cultures, grounded in authentic leadership, a care for people, and psychological safety (e.g. NVIDIA, Slack). In our capitalistic society, ends justify the means; a toxic work environment is rewarded by investors, insofar as the business is growing and printing money. Regardless, cultures are set from the very beginning. 

There were many brilliant jerks during the hyper-growth years at Uber. Shockingly, Uber did not roll out its first set of cultural values until year 6 of its start-up existence, after it had already grown to a few thousand employees. These values included “toe-stepping”, and “always be hustling”, which were often weaponized to get one’s way. 

Case in point: Anthony Levandowski “toe-stepped” his way to taking the top job at Uber’s self driving car division, “hustling” stolen secrets from Waymo into his start-up, selling his start-up to Uber, and trashing the team. Progress on the technology side halted under his leadership, leading to massive attrition. 

I happened to have an unfortunate, front row seat in this debacle. My wife and I will always remember the fateful call during our honeymoon, when I was informed Travis had replaced my current boss - who was one of the most gifted technologists and wonderful leaders I’ve ever worked with - with Anthony, who immediately disbanded my team, among many others. Anthony ended up being sentenced to 18 months in prison. Uber - despite its deep bench of industry leading technologists and experts - ended up selling its self driving division to Aurora in a deal that resembled a massive acquihire. You can assemble a world class team, and still not succeed, if you do not prioritize your culture. 

When my co-founder and I set off to build rideOS, we were determined to learn from the parts of the Uber culture we hated, while still fostering innovation. We wanted to build a culture that truly cared for its people, focusing on the “how” just as much as the “what”. We eventually developed values centralized around doing good by serving people, and used words like kindness and forgiveness, running against the grain of Silicon Valley’s hustle culture. Employees that joined in the later years were amazed by the type of workplace environment we and the leaders had cultivated. 

What people don’t see are the hundreds of mistakes we made in building the culture. The reality is that the culture at rideOS was very tense in the early days, and far from perfect. Folks “passionately debated” the product roadmap, and wrote scathing remarks on each other’s pull requests. (I’ve become allergic to using the term “passionate debates'' as a guise to rationalize away one’s abusive behaviors.) I personally had to de-escalate every other meeting - literally sitting down with groups of engineers, asking them to read their pull requests comments out loud and reflect upon whether or not there were kinder ways to communicate feedback. 

I made mistakes and hired the wrong people. While we were ahead of the curve in terms of writing down a set of cultural values a few weeks into starting the company, we did not realize that it was important to screen for these values during the interview process. We had many of the world’s best engineers working at the company, but they did not work well together as a team. We did not invest heavily enough into properly onboarding folks, and giving them clear expectations for how they should be working together as a team. 

*v2 of rideOS cultural values

For all the founders asking for advice and guidance as it relates to building better, more inclusive cultures, here are 3 things I have learned: 

1. Culture starts at the top, and at the very beginning. As CEO, your behaviors, words and actions carry power and influence, so remember to use it wisely. Find out your blind spots by reaching out to folks you have worked with and ask them to identify 3 words that come to mind to describe what it’s like to work with you. Ask them for constructive feedback on areas of improvement. Do these descriptions align with the vision you have for the culture? If not, it’s time to do some internal work. You are going to reinvent yourself many times as the company grows, so get comfortable with constant change. 

2. Treat culture like your product roadmap. The pace at which technology can impact the world is breath-taking in this day and age, but with faster growth, and a bigger team, comes more problems. Give your culture the same amount of attention that you give to your product roadmap, from the values you write down, to the process you use to solicit feedback and implement change. Implement a weekly people task force to talk about cultural problems, along with ideas for solutions. 

3. Investing in culture is one of the best ways to do good: Cultures outlast companies and products, and building a good culture can leave the world in a much better place than it started. Folks working at your organization will carry the behaviors and practices to their next organizations, creating a powerful web effect. While your company may not be directly saving lives, establishing a great culture is one of the most direct ways to impact people’s lives directly and positively. 

There are no shortcuts to building a fantastic culture, and great cultures are the result of a thousand improvements. Cultures outlast companies and products, and building a good culture can leave the world in a much better place than it started!  

Note: some of the most difficult choices you encounter as CEO revolve around determining how much you are willing to compromise your values in return for business success. We’ll dive more about this in a future post.