About a year ago, I stepped away as CEO of Scripted.com — a company I co-founded and led through our Series B. It was an unusually long journey getting Scripted to the stage we reached. We started off in 2008 as a screenwriting software company in Los Angeles, and grinded out several long, hard years before getting any traction with Scripted. We were lucky to time a few things right (the rise of content marketing + marketplace businesses in general) and I’m proud of what the Scripted team continues to accomplish with the new CEO.
Stepping away as a venture-backed startup CEO is a crazy experience. Here are some of the things I learned in the past year of not startup CEO-ing:
You have no idea what you are putting your body through as a startup CEO: The first month of not being a startup CEO, your body basically goes into shock. After p
utting myself through 5 + years of literally constant stress (managing the business/employees, fundraising processes, hiring, travel, etc, etc) my body just crashed out. As a relatively healthy 30-something, I found myself toward the end of my time at Scripted with elevated blood pressure almost daily. Another thing that startup CEOs refuse to talk about publicly, but will in private settings is how anxiety plays a factor in your day-to-day life. You are constantly feeling “adrenaline-fueled” and that’s what gets you through the fact you should be sleeping 4x more. My BP went down, and my anxiety went away after month 1.
You have no idea how intertwined your entire life is to your startup: This one was particularly hard to get over. Everything about your life for the past 5 years was focused on one individual goal — to make your company successful at all costs. You were ALL IN on doing everything you could for the company and its employees. But your identity is also deeply intertwined in the startup — people knew you as the “Scripted CEO”. Your Amazon Prime account was linked to your Scripted email address. It took several months to untangle the mess between my personal and professional life. And in a way I had to “mourn” the fact I was no longer CEO of this company I helped build.
Some of your “friends” are no longer your friends: The Bay Area is starting to exhibit some shocking similarities to the Los Angeles entertainment scene. One day you are in, the next day you are “out”. CEOs of venture-backed startups with decent profile in the Bay Area are like rockstars. Once you are no longer in that position, people who used to reach out to you — conferences you used to get invited to — a lot of those privileges disappear. The upside to this is that the real relationships endure no matter what.
You IMMEDIATELY get ideas for companies, and they are all really shitty: I was fortunate enough to have Ashu Garg, a GP at Foundation Capital, reach out to me to join the firm as an EIR shortly after I left Scripted. I remember my first meeting with Ashu — telling him about all of these amazing businesses I planned on starting. As an entrepreneur, you think to yourself — I have to do something bigger and better based on the lessons I learned and it has to be RIGHT NOW. Don’t do it. You will end up jumping into something stupid that you are not passionate about. Instead, I took a different approach, and acquired the assets of The Bold Italic — a publishing site, which I run while @ Foundation — it’s a site that’s already working, and is fun to maintain. It keeps my skills sharp, while not diving in full bore into a company where I raise another $15M.
You think about what you would have done differently: You go through a phase where you think about how you could have managed the business better. You realize that you made some bad hires that sucked the energy out of you rather than give you energy. You realize you could have made a different business decision or two.
But ultimately, you move on: The one characteristic I can say about most of the successful people I know is that after they face adversity, they move on. Whether it’s moving on from a company, a personal challenge, a health problem, etc — you find a way to cope and move on. If you linger and wish things could be the way they once were, you will ultimately fail, be filled with resentment, and can’t get to what’s next. I’ve got a lot to look forward to this year, and I’m excited for what’s ahead. I had an amazing year of reconnecting with family and close friends, and I’m thankful for everything I have in my life.
