It's been a while since I last published here. I've still been writing but just not publishing.
I've recently joined SportHold as a co-founder. I was about to get in touch with Mike Casey over something else but he happened to get in touch with me first. We met for breakfast in Pyrmont at the end of February. By that time I the thing I wanted to talk to him about was no longer relevant but I sensed he had something big he wanted to discuss with me.
He's an angel investor and advisor to SportHold. He told me what SportHold is all about and he asked me to quit my steady job so I could come on board fulltime. My first urge and gut feel was to say "Yes" immediately but I told him I'd think about it and give him an answer in a week.
I had a lot on my plate and a lot to think about. As well as this decision my girlfriend was returning to Japan for good in two weeks and I was turning 30 at that time as well. It reminded me of when I turned 18, started university and got my driver's license all in the same week. Or 9 months ago when I ended a 2 year relationship, changed jobs and changed apartments in the same month.
I spent the next weekend in the countryside with the plan of thinking it all through. Truth is I didn't think about it much at all, I just spent the weekend relaxing.
Monday was deadline day for me and I was going to meet with Stu Fox to talk about it. He's become a mentor of sorts who I know from running the Startup Poker Meetup. The meeting fell through but the upshot was that ended up sitting in Hyde Park opposite my work place with about an hour before work started.
Deep down I knew what I wanted to do but to me life is mostly about timing. It's about choosing when to pull the trigger. I recently saw the Pandodaily interview with Path CEO David Morin on YouTube and his response to making the choice to leave Facebook really resonated with me. He said he agonised over it for a year before he pulled the trigger (I even found the exact spot in the video where he discusses it - you're welcome).
It goes back to the feeling I felt when I stood in San Francisco Airport in May 2012 and vowed I would return in two years. I was returning with my then-girlfriend from a trip where we'd sailed from Brazil to New York and we had a stopover in San Francisco. My interest in startups grew on that trip when I read Tony Hsieh's book and had started reading more and more about startups. I wanted to go straight to the Valley from New York and see what I could make happen. I wanted to pull the trigger then as much as I wanted to when Mike asked me to join.
At the time standing in San Francisco airport I was broke, knew nobody in the Valley and knew precious little about the startup world. If it were a movie then this would have been the time I'd strike off into the wild unknown to make it happen. But movies are often wrong. Back then I made the right move. I went back to Sydney, got back on my feet financially and spent my spare time getting into the startup scene.
I got my hot desk at Fishburners, met people, worked on projects and grew my network. I took my chances when they came along like interviewing Gary Swart from oDesk when I got the chance and managing the Fishburner's newsletter. I figured I'd wait until it no longer made sense to keep a day job before switching over. That was my thought process for a long time.
But in the past few months I started having other thoughts. Six months ago when I changed jobs I got a 40% pay increase. I figured I'd have more spare money to work on side projects. For the most part I did but not as much as I thought. It suddenly occurred to me that my day job was becoming a trap and that if I didn't make changes I'd wake up tomorrow and be 50 and still playing it safe. The more money I would make and the more comfortable I became the further away I'd be from doing what I truly wanted to do with my life.
These were the thoughts that I was having as I sat in Hyde Park. Had I done all I could to earn the right to make this decision? Had I done my due diligence to lay the ground work for taking my shot. It's not failure that bothers me so much as the time it takes to recover from it financially. That's why I was having a hard time knowing what to do.
So I took out some palm cards and a pen and drew up quick matrix.
On one side of the palm card was the heading: "Staying in job" and the other was "Joining SportHold". I had rows titled: "Pro" and "Con".
I did all the cons first and then the pros of staying in my job. I figured those would be the easier ones to fill out. There were things like financial ruin, lost time for the startup not working. There was loss of soul from staying in the job. There was comfort, security and the ability to wait for the next opportunity to come along as "pros" for staying in my job.
Then it came time to writing the "Pros" for joining SportHold. I went to write but couldn't. My pen froze in mid-air. I knew. I just knew. I had to do this. I was kidding myself to think I had a choice. I knew all along when Mike asked me. Deep down, the decision had been made. The rest was my way of being OK with the decision. Trying to rationalise it through the paradigm I'd built up to explain my startup journey and it's direction thus far.
I put the pen away and wrote the following text: "Cowabunga motherfuckers. I'm in. Good morning btw." My finger hovered over the send button. 'I should at least finish writing the column', I thought. I started writing the column and got half way through the first bullet point and there it was again. Absolute certainty. I put the cards away and sent the text.
You'd next expect me to feel some sort of relief, right? Euphoria, iron-willed, flinty-eyed certainty? Nope. I mostly felt terror. And then, in reaction to the terror and sense of reassurance. I felt glad that I was frightened. It reaffirmed to me that I was making a mature decision. When I was 20 I was more prone to making bold, impulsive and big life decisions.
At my recent birthday party my mum gave a speech and mentioned a few things I'd completely forgotten about. One was that I had told once told her at 2pm during a day in 2007 that I was thinking of working in Korea. At 5pm I told her I'd found a job and the contract had been signed. I was going away for a year. Don't get me wrong, I didn't say yes to everything and anything. When traveling in Bulgaria in 2008 I was offered a job placing Bulgarian nurses in jobs in the UK. I turned that down and whilst I wonder what might have been I'm pretty certain it wasn't a totally legitimate business.
But walking out of Hyde Park to work I felt my fear was proof that I fully understood the decision I was making and the implications of it. Young men are excited to go to war whereas veterans do so with a sense of reticence. I was (and still am) excited but I go into this with my eyes wide open. Waiting longer would leave me jaded and if I'd gone sooner I'd lack awareness. I'm right in the sweet spot and I know it.
It's time. It's my time.
I walked in and called a meeting with my manager. I'm always irrationally terrified that my manager will fly off the handle when I quit. Every time I've been delightfully surprised that they understand. This time my manager was only disappointed I wasn't moving to Japan to follow my departing girlfriend.
Everything that's happened since I made that decision on the 3rd of March has already made it so worthwhile. Funnily enough I've never been more productive before in my day job. I'm sleeping better and my focus is laser-sharp. I only wish I had more time to prepare before I fly out to San Francisco on 4th April. I still have one more week's notice to serve out (in Aus the standard is 4 weeks) on the 28th.
We're trying to raise money and I sincerely hope we do but, in all honesty, it's not a problem for me if we don't. I'll work on SportHold until one of two things occur: it succeeds or I die. It's that simple.