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My Biggest Mistake: Launching a Tech Company Without a Technical Co-Founder

Ryan Buckley and his partners sank $70K into a tech startup they didn't have the know-how to maintain. It took them three years to recover.
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This is the first in a periodic series of columns in which entrepreneurs recall the invaluable lessons they learned from their biggest blunders. Kicking off the series is Ryan Buckley, the cofounder of Scripped.com, a screenwriting software product that spawned Scripted.com.  

 

My entrepreneurial journey started with a text from my cofounder. It read, "I have THE idea that will make us rich." He was wrong, of course. Mostly.

I had just turned on my cell phone for the first time since returning from an adventure-filled European backpacking trip. Up popped the text. This was 2006, just as I was beginning a Master's program at Harvard's Kennedy School of Government. I had quit my consulting job and had every intention of returning to the public sector. I wanted to go into politics.

That path quickly changed as we moved from initial conversations to resource commitments. There were three of us then: Zak Freer, Sunil Rajaraman, and me. I took calls at cafes in Harvard Square and answered e-mails in the hallways in between classes. I decided to go in. We each committed $10,000 cash (I didn’t have it, so I used my student loans) to hire an outside developer to build an online screenwriting software product.

That was my biggest mistake.

It may seem obvious now, but back then not having a technical cofounder seemed reasonable. How hard can it be to re-engineer Google Docs for a screenwriting environment? Thirty grand should do it, right? Oh yeah, easy.

This was at a time when the iPhone hadn’t launched yet, MySpace still had users, and Google had only recently purchased Writely, the collaborative text editing software behind Google Docs. "Cloud" simply meant "rain" and there we were, three people on a mission to merge Silicon Valley technology with Sunset Boulevard production.

In other words, for the first time since the 2000 tech bubble, it felt like open season for startups. Anyone could hire overseas talent and slap a website together. You didn't need to worry about being mobile, going viral, or checking in. I look back on 2006 and can say with certainty that life was simpler then.

We built and tested Scripped throughout 2007 and launched in January 2008. At its core, Scripped was Google Docs (or Draft in today’s terms) with the features that screenwriters care about: hot keys for Character and Dialog formatting, and page cutoffs that don’t follow Word standards. We had the first purely Web-based screenwriting software product on the market.

The problem was, since we owned the tech but couldn’t maintain it, we were completely hamstrung by cash. A technical cofounder would have allowed the rest of us to focus on growth opportunities and partnerships while he developed new features. We could have worked our way into film schools and screenplay competitions. There would have been time to think through a revenue model. Most importantly, investors wouldn't have looked at the three of us econ majors and shaken their heads while asking, "So, guys, exactly who is developing your product?"

This is what happens when you launch a technical company without a technical cofounder:

You don’t pay yourself. Ever.

Despite not paying yourself, you still run out of money.

Without money, you can’t fix bugs.

When bugs persist, users leave.

When users leave….

As of our 2008 launch we had spent $30,000 of our own money and another $40,000 of friends', family, and small angel money on outsourced developers. We were giving away the product in order to get attention from writers who might help us break into the Hollywood studios. In other words, we had no revenue model, no cash, and no reasonable hope of ever making it.

In a strange way, that's what saved us.

Not having a technical cofounder forced us to be scrappy. While competitors in our space doubled down on technology, we became innovative marketers. My cofounder was at UCLA and leveraged his resources to meet other entertainment entrepreneurs like Keith Richman from Break.com. We got some celebrity screenwriter endorsements. Competitors emerged with better tech, but we had a better brand, and we persevered. When a competing company was on the verge of collapse, we merged with them. It bought us more time and a great partner and angel investor.

It took us three years to pivot Scripped over to Scripted, our fast-growing original content company. As soon as we raised our seed round, we hired the best engineer we could find and built Scripted on the hot Ruby on Rails web framework. We now have five terrific engineers on our team and plan to hire several more in the next six months. We still don't have a technical cofounder, but I've taught myself a lot of programming in the last five years. I can't do what a real engineer does, but I can at least understand the lingo.

Yes, we absolutely should have teamed with a technical cofounder early on. That was a big mistake. But the silver lining is that it forced us to be scrappy. We earned our stripes, and out of necessity, I learned to code. Ultimately, we beat the odds and made it to a big Series A led by Redpoint Ventures.

But I wouldn’t recommend this path to anyone.




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