Surf Roots, Software Thoughts

I recently announced that I was heading up to Mammoth Mountain for some snowboarding. Turns out me, my good buddy, and my family are having a killer time, but the vacation is making me think of a former friend of mine, call him Scott, who used to travel to Mammoth with us. And so goes the story of Cellarspot, Scott, and why friends should be careful when going into business together:

Scott and I had been friends since middle school and very close friends since high school. He’s the same age as me, and he’s studying entrepreneurship at USC. I started getting very involved with academia and computer science my sophomore year, so I started working on Cellarspot in the summer of ’06 to apply my newly learned skills. I mentioned the idea to Scott sometime that summer, and he said it sounded like a good idea. A lot of time went by, and I finally started taking Cellarspot seriously in winter ’07. Scott and I had dinner when we were both home for winter break, and he expressed interest in helping out and being involved. I said that’d be cool, but we didn’t move forward from there at all. At about this time, Scott started getting very involved in his entrepreneurial studies, building his interest in Cellarspot a lot. He kept asking me, “What can I do?” I would reply, “nothing,” because my classmates and I were working on the website and there wasn’t anything for a non-technical person to do. He continued to ask me this question through March ’07, and my answer never changed. On a sunny, Sunday morning in April ’07, I got a phone call from Scott that would eventually terminate our friendship (literally).

Scott told me that he was planning on raising capital for Cellarspot so that he could outsource the website to the Philippines. At this time, Cellarspot had already launched but still needed tons of improvements. Scott wanted me to make the improvements, but I didn’t really have much time seeing as how I was insanely busy with senior-level CS classes, TAing, and other things. By outsourcing the website to the Philippines, Scott would be able to get changes made to the site quickly. I didn’t like this idea.

My initial reasoning for not wanting to raise capital and outsource the site was because I loved working on the website. Moreover, the whole reason why I started Cellarspot was to make a cool website and have fun and learn along the way. I thought it would be cool to make money, but that was never my initial intention — I didn’t want to give something I love away. Some of my reasoning was also selfish in that I didn’t want to have pressure from investors, because my main focuses at that time were school and TAing.

When I told him, “no,” Scott started to lecture me about respect, because he learned all about respect in his fraternity. Apparently Scott had been networking with people about Cellarspot for quite some time now, and he was angry that his networking would now be wasted because I wasn’t willing to move forward at the pace he wanted. I would be angry if I were him as well, but he was never upfront with me about what efforts he was making. It’s almost as if he had a plan the entire time that he kept secret from me.

After the phone call, Scott de-friended me on Facebook, and we haven’t spoken since. It’s really sad to see a long friendship end over a business that makes about $5 per month on average, but I suppose that’s just how it is. I wish I could have gone back and handled things better, but I can’t. My only hope is that others learn from my mistakes and maintain their friendships.

Lessons Learned
First, make sure you are always upfront. Instead of telling Scott, “There is nothing for you to do,” I should have said, “You should work on something else and stop thinking about Cellarspot.” This is hard, though, because I didn’t not want Scott to work on Cellarspot. I wanted him to be involved with iterating on the website, but I didn’t want him to take total control of the site and rob me of my technical fun. We both should have been more upfront with one and other about what we wanted and what we could offer.

Second, look for signs that your business is interfering with your friendship. Once Scott and I entered a dialogue about Cellarspot, he would introduce me to his fraternity friends as his “business partner.” Weird, huh? I should have recognized this as an interference and acted on it. Instead I just kept going with the flow and didn’t really think about it outside of being weirded out that we were no longer friends but instead “business partners.”

Third, analyze your friendship prior to becoming business partners. If you have any doubt whatsoever before going into business together, then don’t do it. Scott and I had been great friends for a long time, but Scott is very, very stubborn and opinionated. Even in high school the two of us would angrily argue about silly things because our opinions differed. I’m not very confrontational and argumentative at all. In fact, there have only been six people that I’ve had angry arguments with on a semi-regular basis: my mom, my dad, my sister, my brother, my roommate, and Scott. I should have realized that Scott and I would engage in angry argument and not rationally come to conclusions, making business impossible.

Forth, just remember that freakishly good friendships are infinitely more valuable than business and money. My friendship with Scott prior to Cellarspot was on the decline from freakishly good, but relationships always have bumps in the road, right?