Innovation

I’ve been given a lot of chances by a lot of people. Some I’ve taken great advantage of. A couple I’ve pissed away.

(This is part of a collaborative answer to: Who took a chance on you?)

I’ve mentioned before how broke I was in college. That was a guiding influence to find a co-op opportunity. A co-op is a job where I could go to school for a semester, and then work for a semester, then go back to school, then back to work, etc. The making money part was very attractive. So was the awesome experience.

As a Freshman, I interviewed for a co-op position with 3M, well known for Scotch Tape and Post-it Notes. To prepare, I read some pamphlets about what 3M does and how innovative they are.

I sat in that interview, inexperienced, naive, using standard cliches like, “I work hard.” And now I’m blabbering on about how important “innovation” is.

The two interviewers got sick of me saying that word so often. Innovation. Innovation. So one of them asked me, “What does innovation mean to you?”

I was just a college Freshman. When I wasn’t working my ass off, all I wanted to do was go to a house party, or drink Popov Vodka in my dorm room. My roomate and I invented a drinking game using the card game War. Invented. Who am I kidding? You play War. When it’s time for a war, you drink. And now here I am in this interview without any real idea what innovation is.

But I immediately blurted out something like, “Innovation is two things. First, you obviously have to spot something that people aren’t doing yet. But second, most importantly, you need to have the courage to do something different than what you’ve grown comfortable doing.”

I have no idea where that came from, but somehow it impressed them. The two interviewers eyes opened wide, they looked at each other and smiled.

I got the job offer to co-op for 3M.

I talked it over with someone advising me. We were both clueless how opportunities like this work, and thought I could play the field a little more. Maybe even make a little more money.

As I tried to see what else was out there, the offer time-bombed, and it was rescinded.

We got greedy and I pissed the chance away.

In 2005, I applied to Y Combinator (YC). They provide seed money to get fledgling technology businesses off the ground. I had wanted to start my own business since college. My first attempt at creating a software business was database administration software for mobile devices like the Compaq IPAQ. I never shipped anything. Other attempts at starting a business had similar results.

So applying to YC seemed like a pretty good next step for me. We got an interview.

My partner, Adam, and I travelled to Boston for the interview, and the night before, we went out for Indian food. As we were finishing up, Paul Graham, Jessica Livingston, and Aaron Swartz walked in the door. Paul and Jessica are two of the founding partners of YC. Aaron, one of their first investments.

Adam and I thought we should introduce ourselves, in order to hopefully leave a good impression for our interview. We walked up, before they ordered, and introduced ourselves and our company. Paul blankly stared back at me like he had no idea who we were. Jessica, though, recognized our names and introduced the group. That was it. We told them we looked forward to chatting tomorrow.

Pretty sure we weren’t on Paul’s list of startups he was looking forward to investing in.

My feeling was further confirmed, when we showed up for our interview. Here I am, now a naive software engineer, telling these investors we were going to build this business better than those who had come before us, but I sensed Paul knew we had no idea what we were doing.

However, later that day, we got a phone call that they wanted to invest in us. Another time-bomb.

Lots of fear, uncertainty, doubt and greed crept in. Are we giving away too much equity? Is the opportunity cost too high of leaving my job? Can I stand being away from my home for 3 months? Will I get along with my partners whom I barely know?

But I’ve been here before. I’ve screwed this up before.

We called them back in a few minutes and agreed to their offer. Inkling was going to be a company.

Somehow we convinced YC to take a chance on us. And that chance turned into a business. And that business has now been around for over 7 years. It’s paid a handful of people good salaries and I’ve been working for myself ever since. It’s been used by dozens of Fortune 500 companies and the US Federal Government.

Even 3M has used Inkling.

It wouldn’t even exist today, if YC hadn’t taken a chance on us. It wasn’t about the money. They gave us $17,000, which we could have pooled together ourselves with the good paying jobs we had at the time. But their buy-in was the activation energy we needed to believe in ourselves, quit our jobs, and commit to the business full time.

Fast forward to 2011. Inkling had matured as a product, and I wanted to try something new. And YC gave me another chance.

It’s taken me a couple years. A few false starts. Took a 6 month break to regroup. But I was finally able to take another of YC’s chances and turn it into Draft. It’s still early. It’s impossible to say how things will turn out. But I can say, that a lot of people really love Draft. They are paying me for it. The numbers are growing. And I have never had this kind of momentum before.

None of this would have been possible without those chances and a hell of a lot of hard work. And maybe?

The courage to stop doing what I’ve grown comfortable doing.

P.S. I’d love to meet you on Twitter: here.