The Best Parts, and the Hardest Parts of being a Startup CEO
I wrote this one a while ago, and just recently dusted it off/updated it.
I was a startup co-founder/CEO for 4 years. I co-founded a company called Scripted, and led us through our Series B financing. There are lots of positives and negatives associated with being a startup CEO. It is simultaneously the hardest, but most rewarding job I can think of. For those of you thinking about taking the plunge, you should know the good and bad that comes with being a startup CEO*. **
*I am speaking specifically about technology startups that require outside financing at some point in their lifecycle.
** Warning, I used a lot of sports analogies.
The Best Parts
You get to choose who you work with — I’ve worked for a few big companies in the past — you meet all sorts of people — people you want to work with, people you don’t want to work with, and everywhere in-between. Startup CEO was the only job I’ve ever had where I have control over the team and the culture. Once you establish the core team and the culture, you can empower others to carry on the culture and hire great people. This is unquestionably the best part of being a startup CEO.
You constantly push your own limits — I was a tennis player in college, and I’ve always loved competition. At every stage of a startup, you are forcing yourself to compete at a higher level, sometimes even when you aren’t ready (the tennis analog for this would be like qualifying for a Grand Slam tournament when you’re ranked outside of the top 300). The learning curve is steep, and if you can keep pace, you’ll feel like you can take on any challenge.There is no other job where you’ll learn as much as fast — and you’ll meet fantastic people along the way.
You get to work on a problem that you’re passionate about — In my case, I felt/still feel a strong sense of passion/mission about helping writers. And I don’t just mean journalists — I mean writers from all walks of life who are talented and deserve to get paid for their craft. I’ve always respected writers, and feel like they are an underappreciated group. I hope someday it will be trendy to get a creative writing degree from a college, or university because people will recognize you can get paid well for the work. I don’t recommend becoming a startup CEO unless you find a problem you’re truly passionate about solving.
The Hardest Parts
You will not be universally loved — If you are a people-pleaser, who needs consensus from everyone — and a feeling like you are loved by all at all times — don’t be a startup CEO. From the moment you start a company, to the moment you take that first round of financing… competitors, friends, etc may not ALL be rooting for you. Some may even revel in your failures and come gunning for you. A great recent example of this is Meerkat, which just shut down its livestreaming product to focus on something else. A lot of folks I know are saying “I knew that wouldn’t work”, or worse. You need to have thick skin and realize you cannot keep all people happy at all times. You have to focus on making the right decisions for the business, and not manage to make people like you.
Managing the ups and downs — A lot of great literature is finally coming out about the ups and downs that come with being a startup CEO. A venture capitalist I met put it best — “being a startup CEO is like being a coke addict — extreme highs and extreme lows — my biggest job as a board member is to help the startup CEO ride the roller coaster”. One minute you close a round of funding, the next you could lose a key team member, the next you could win a major contract. You never know what you’re going to get when you walk into the office. Your work life then bleeds into your personal life and you lose balance. You can kiss goodbye any sense of “stasis” once you decide to become a startup CEO. The best way to mitigate this is to build a great team of advisors and mentors around you. For me, folks like James Currier, DJ Patil, and Gary Swart helped me tremendously.
You will be second guessed, and you will second guess yourself (similar, but not the same as above)–People involved with the company, and people not involved with the company will constantly second guess your decisions. Worst of all, there may come moments where you second guess yourself. The sports analog for this would be like Jim Harbaugh second guessing himself for throwing to Michael Crabtree against Richard Sherman during the final play of the NFC Championship a few years back. Everyone under the sun questioned the play call, but I bet Harbaugh wouldn’t have done anything differently if he had a second shot. All you can do as a CEO is make the best decisions you can with the resources you have at the time — if the ball is moving forward at a great pace, you are making more good decisions than bad decisions.
Letting your Team Play the Game — When you start a company, you are literally doing every job — product, sales, marketing, customer service, hiring/recruiting, etc. Letting go and not micromanaging is the only way your company can scale. You have to hire a great team and trust your team to do the work. You also have to learn how much rope to give team members, and exhibit a great deal of patience. Greg Popovich is a master of this, and embodies just about everything I’d want to be as a leader someday. Should he have taken Kawhi Leonard, a rookie, out of the 2013 NBA Finals before he missed those free throws? Maybe. But the team stuck with him, and in 2014 the Spurs won a championship and Leonard was MVP.
The startup game is a marathon, not a sprint. Despite the once-in-a-blue-moon stories like Instagram, there are very few companies that experience what outsiders perceive as “overnight” success. Before you start your company, recognize that it’s going to be a years-long journey fraught with ups and downs and danger at every corner. With that being said, I can’t think of a more rewarding job in the world.
