The end of a careera…

ca·ree·ra
/kəˈrirˈrə/
noun
a long and distinct period of a time in a career with a particular feature or characteristic.

TL;DR After 11 years in startups, I’m taking a career-break and moving to Athens, Greece with my wife Karina Rook to become a mid-life-crisis-boat-bum and live on a boat for a few years. Read on to find out more!

It’s almost-to-the-day 11 years ago that I first met Alex Dong and my career trajectory changed dramatically. After a few months of planning, I took the plunge and quit my job at PricewaterhouseCoopers. As I like to say “I ran away to join the startup circus”.

It’s overwhelmingly been one of the best choices I’ve made in my life and started a wild ride that I’ve enjoyed immensely. Although it’s been tough at times (to the point early on that we had no savings left and were deep into our overdraft and over 50k in personal debt), there’s no doubt that overall it’s been a great success. I’ve taken risks, I’ve bet and worked on long shots and come out of the experience changed for the better.

Still, there comes a time to re-evaluate what’s important and the midst of a global pandemic seems like a good time to do just that. As Karina and I took stock of our lives (kids left home, sold our house and cashed up, almost 50…) the realization was that we have options and we are fortunate enough for that to include not working for a bit.

Not only did the time feel right for a change, we increasingly felt that NOT doing what we wanted would lead to future regret. We could knuckle down and push these dreams out for a few more years, but what this pandemic has brutally shown us is that the future is unknown. There’s no better time to start than today.

Our longer-term goal for several years has been to buy a barge and cruise the canals in Europe based out of the Netherlands. The reality of visa issues and residency permits made this a challenge. After considering a lot of options we chose Greece and cruising the Mediterranean which is something that I’m even more excited about! I could do a whole post on what we’ve learned through the process (and perhaps might in the future).

So we’re off, leaving the USA and heading to Greece, the end of this “careera” for now. I feel I’d be remiss to do so without mentioning a few of the people who have made my time back in Melbourne and here in Silicon Valley working on startups so rewarding. Buckle up, it’s a long list, I have a lot of people to be grateful for.

Firstly my family! Karina Rook, Ella Rook and Jasper Bull — I couldn’t have got to where I am today without their support. It’s easy to set off on a wild adventure when Karina’s definition of the worst that could happen is “so what, we have to sell our house? That’s not so bad, I’m bored with this place anyway.” Thank you all three of you for support. Ella is currently in Edinburgh and Jasper in Sydney and open to work opportunities, I recommend them both!

Alex Dong — my “OG” co-founder and still at the grind now with HappyMoose (check them out if you want to print awesome wall stickers online). Alex is still one of the most well rounded technologists I know, a true entrepreneur and a friend. He makes me happy every time I work with him, even when we occasionally argue!

Didier Elzinga, Jon Williams, Doug English, Rod Hamilton, Tom Howard, Fenn Bailey, Ned Dwyer, Cris Pearson, Mark Mansour and more — those “Startup Food” dinners back in Melbourne kept me sane and made me feel like part of a family. I’m not sure I’ve been great at applying every lesson I learnt from you all, but I’ve strived to apply them everyday. The power of networking has led to many great opportunities for Karina and I from here too. I should mention Sean Callanan who was endlessly supportive through advice and contract work and Scott Kilmartin who’s love of ice cream and all things entrepreneurial inspires me.

Steve Chen — You shoot big and aim high! Without you pushing to take a risk on Alex and I, we may never have made it to the US and AVOS. Thank you for the opportunity.

The team at AVOS, MixBit and Zeen — there’s too many to mention you all, just know that you all prove the maxim that Silicon Valley is full of smart people and it’s been my pleasure in getting to know you all, you smart, crazy bunch (none crazier than Doug Hicks who broke his leg the week before a wedding in Hawaii playing basketball with the team).

The NZ crew (Meg Garner, Josh Garner, Sam Garner, Jan Dawid-Root, George Sealy, Gerwin Van Royen, Daniel Sutton, Ben Bishop and more) — thanks for all your hard work over the years, you’re proof that crazy smart people don’t just exist in Silicon Valley but in Dunedin NZ too! We could never have achieved what we did without you and I’ve come to really love Dunedin. I’m sad I won’t get back there to see you all for a few years now, but when I do, let’s catch up.

Brent Hurley — A steady hand at the financial helm, you’ve been a great mentor and sounding board for many things around which I had a lot to learn. There’s more than a few times that your sympathetic ear made all the difference.

Ches Wajda — You’re going to do great things in product management, you’re one of the most thoughtful and introspective people I know, I’ve learnt a lot by learning to listen to your thoughts and design advice and you were a great supporter of what we achieved at Zeen.

Matt Miller and Andy Chen — you guys crack me up, keep me sane and keep me laughing — who knew competitive Golden Tee was such a thing? We have to get together again once the US is allowed to travel again (Vegas trip?). Matt, keep up the hustle and Andy, you always amaze me with a solution to any problem. You both each deserve your own page, but it felt fitting to list you together.

Finally the GreenPark Sports team, what to say. The hardest thing about boarding a rocketship is jumping off as it’s heading for the stars — you’re all insanely talented and I spent most of my days in awe of what everyone is collectively producing from engineering to art. Travis Beauvais and Andy Baron — you two are the brains and heart of the engineering team, I know that it’s going to go to great places under your leadership Travis. Alexander Stein, with you at the creative helm, I can’t wait to see how amazing GreenPark becomes, it’s already blowing my mind and the team has so much further still to go. Jenn Amato, thanks for being such a sharp operator — it sometimes frustrated that part of me that likes to fly-by-the-seat-of-my-pants but it also made me sleep easy knowing that you were there to keep us on the path.

If you’ve read this far, the GreenPark team is super talented, creative and on a mission — they’re also hiring https://boards.greenhouse.io/greenparksports, I can’t recommend them highly enough.

And of course, the GreenPark founders, people I couldn’t be happier to have spent the last 2 years working with and to call friends, Ken, Nick and Chad.

Ken Martin — 2 years working together was far too short. You’re the MOST insanely creative person I’ve ever had the pleasure to know and I loved working with you and creating the reality of the vision for GreenPark. If a picture is worth a thousand words, your decks are legendary and worth a million. Let’s catch up soon! Maybe when you come to strike a deal with Ελληνική Σούπερ Λίγκα (if we can ever get you on a plane to Europe)?

Nick Swinmurn — your energy and attention to minutiae is infectious, every meeting is a ride 🤣. You reintroduced me to fitness through Dozen and I’m healthier and in better shape now than any time in the 10 years prior. I’m in awe of the number of ideas you juggle at any given moment, can’t wait to see what’s next — hit me up, whatever it is, I’m in! Next time you get to Denmark or England, come stop by Greece and say hi! Go Tottenham, Go FC Helsingør and Go Warriors!

Chad Hurley — Last but far from least, what can I say! For 8.5 years now at AVOS, MixBit, Zeen and now GreenPark you’ve been my boss, mentor, partner-in-crime and friend. Your generosity in sharing experiences with those around you is legendary and your passion for the vision is inspiring. Building products with you is something I will always remember (mostly fondly I think 🤔), who knows, maybe we will again. So many good times and great stories, we will catch up again soon. Go LAFC and of course Go Warriors!

This is a long list of people, but in many ways it’s too short! There’s more that deserve a mention and a shout out — you’ve all influenced me in so many positive ways.

At the risk of making this far too long, one other achievement I’m proud of here in the US, is my involvement on the board with Design Tech High School. I’ve learnt a lot about Design Thinking and education through the efforts of Dr Ken Montgomery, his amazing staff and the great network of people on the board, particularly Mark Kuperschmid. It was my pleasure to serve and thank you for your amazing service to the future of education and helping raise our kids.

As I reflect on this startup phase of my career, the thing I’m most proud of is the teams I’ve worked with. I hope that most people have found working with me to be a positive experience and I take a lot of joy in seeing where everyone has landed and how they’ve developed their future careers — not least because it means that working with me didn’t screw them up too much!

But despite all the great experiences, fun challenges and amazing people, the time has come to step aside and take a long awaited break while I look for the next thing to build in the future. Which, who knows, could be a cheese shop, dive shop, or a wine bar! No promises it will be in tech.

So what’s next? Well definitely that career-break. We’re moving to Athens, sorting our residency and then buying a boat. I’m going on record to say I’m NOT rushing back into a new startup, but I also can’t promise I won’t keep building either, it’s just who I am. Ultimately, if you want advice from a mid-life-crisis-boat-bum floating around the Mediterranean, hit me up. I love startups and problem solving, but as noted, I’m done “working” at them for now. That said, I doubt I’ll be truly happy if I can’t mull over a few ideas and problem solve for people too.

While it feels like a goodbye, it’s really just the start of a new journey. No matter how well you feel you know me, if you get that itch to cruise on a boat in the Mediterranean, hit me up! Karina and I would love to have you aboard from March 2021.

Well, that’s enough from me, it’s time to start the next journey and “run away to sea”.