On being the 3rd CEO of the startup I co-founded

Please allow me to re-introduce myself.

Last July I became CEO of the company that I co-founded with Sunil Rajaraman and Zak Freer nine years earlier, in 2007. Originally, we were a web-based screenwriting software company called Scripped. After building it for three years while Zak had a full-time job and Sunil and I were in graduate school, we hit an impasse in our revenue model. We couldn’t find a way to make more than $15,000 per month.

We had all sorts of ideas, of course. We tried selling screenplays to studios. We tried running screenplay contests, and partnering with other contests. We tried development deals with large brands and TV shows. Then we tried charging writers a subscription fee to use the software. Then we sold lifetime subscriptions.

Then, we gave up on making more money and focused on reducing costs by taking ourselves off the payroll. I went to work for Auren Hoffman on the sales team at Rapleaf. Zak had already peeled off, going back to school to take the classes he needed to get into Harvard Dental School. Sunil also had a full-time job on the M&A team at Applied Materials.

In the meantime, we’d been asked for non-film writing help from companies as large as Levis, and rumblings about Google algorithm changes were stirring up talk of what would become “content marketing.” It felt like we could build something here. Eighty thousand screenwriters had registered on Scripped, and good writing was becoming increasingly valuable.

Opportunity knocked, finally, when an old investor offered to help us coax this phoenix from the Scripped ashes. We called it Scripted.

I left Rapleaf in March 2011. I was 29 years old with graduate degrees from Harvard and MIT, and making $45,000 a year as a sales rep. When I went full-time on Scripted, I still had to take a pay cut. My first Scripted salary was $30,000. My wife was working at a local cupcake store at the time, so even with our rent-controlled apartment, San Francisco was too expensive for us. We were losing money every month, unable to pay off credit card debt from our wedding two years earlier.

My uncle, our first investor in Scripped, bailed me out with a $6,000 check to pay off my credit card. He couldn’t stand that I was paying 23% interest. Instead, I paid him $500 a month for a year, and he waived the last payment. That was his 30th birthday present to me.

By the end of 2011 we were able to raise a seed round for Scripted, which we described as a writing service powered by a tech-enabled freelance writing marketplace. We wanted the entire process of finding, hiring, and managing writers to be magical. So magical, in fact, that you wouldn’t even see it happening. You’d just order your writing job and get it back a few days later. For the most part, it worked!

I met Jake Kring at Rapleaf in 2010 and took to him immediately. We all did. The other sales guys loved Jake because unlike the other engineers in the office, he was approachable and didn’t smell funny. He had enthusiasm, curiosity, and you could tell he was crazy smart. He was the guy we’d ask when we had questions about how Rapleaf worked.

I didn’t know then that I’d get to work closely with him for the next five years. It would have made me happy and proud.

I’d say I’ve been on two founding teams within the same company. The first was my screenwriting product, Scripped, with Sunil and Zak. The second is my writing marketplace, Scripted, with Sunil and Jake. Jake ultimately signed on as one of our first real, non-contractor employees, and is the only one from that first group still involved with the company. I consider him a co-founder even if he’s not one on paper.

Them salad days. Zak, Sunil, and me, posing for the camera, 2007-ish.

Sunil was CEO during both Scripped and Scripted up until he left in January 2015. Then my board appointed our most senior employee (experience-wise) at the time, JD Peterson, to be interim CEO while they ran an outside CEO search. We hired Curtis Kroeker on August 25, 2015, my 33rd birthday. He had the daunting task of commuting between San Francisco and Portland, Maine, where his family expected to remain for up to six months. When they canceled their moving plans, Curtis had to resign. I formally took the reigns of Scripted on July 29, 2016.

It’s a bit odd to become CEO this way. It’s also not lost on me that I was twice passed over by my board during CEO placement discussions. This makes me head of Scripted by process of elimination. Funny thing, huh? It certainly made the congratulatory emails from distant friends and business school classmates bittersweet.

“Yes, thanks, guys.” If you only knew…

I don’t mention this to air dirty laundry. I’ve talked to my board about this stuff, and I don’t disagree with their judgment. It is what it is. But it does color my approach to being CEO, the risks I’m willing to take, and my willingness to put my very own beard on the bottom line.

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