A while back, I talked about setting physically adventurous goals to ensure I exercised regularly, while also gaining the added benefits of a feeling of accomplishment, time outdoors, and time with friends. Over the weekend I rode the Whaka50, a 52 km mountain bike race in Rotorua, and it delivered on all of that. Here I am towards the end of the race:
Concentration face
I aimed to finish under four hours and crossed the line in 3:55, so that was satisfying. Now I have to figure out what’s next, the Faultline Ultra maybe? Anyone wanna join me?
Meet Philip
Startup founder, investor and advisor. Co‑founded Upstock, Xero and Turntable. Former American, Kiwi for 25 years. Doting family man. Keen surfer, photographer, drummer and foodie.
Philip’s story…
I was a co-founder of Xero, which was my path to financial independence. I was 45 when I decided to leave and my net worth at the time was pretty great.
However, right after I quit Xero, the share price tanked, going from nearly $24 to $12. Suddenly, my net worth was essentially cut in half. Right at that exact moment, I discovered that my US accountant had not correctly filed my US taxes. That meant I had an eye‑watering PwC bill to fix and re‑file everything, along with an absolutely crushing tax bill. To make things worse, I had to sell down a bunch of shares at a rock‑bottom share price to pay for the taxes. Fortunately, after I cleared up the US taxes, the Xero share price started climbing back up. I still had enough that I didn’t need to work, but it shows how “net worth” can change in a blink.
Another thing that was weighing on me was when I pictured myself 30 years down the road, I realised that money is worth a lot less after inflation, and the bulk of it has probably been spent. If I retire early, my earning power is long gone, right when big medical bills and elder‑care costs go through the roof.
Regardless, after Xero, I was deeply burnt out and planned to take at least a few years off before thinking about “what’s next”. My kids were still teenagers, so I wanted to spend lots of quality time with them and the family. I’d also taken up surfing at 45. But in Wellington there isn’t enough swell to keep me surfing every day. If I lived near good surf, I almost certainly would never go back to work!
I knew I didn’t have the energy to go back into start‑up life. So I started doing some start‑up investing and advising – I wanted to apply everything I’d learned to help grow the ecosystem of founders and start‑ups in New Zealand.
But after a while, I got bored and restless. I felt like I had all these skills and expertise that were wasting away. The start‑up advisory work wasn’t keeping me busy enough. I also found it frustrating working with some start‑ups that were just spinning their wheels, not good at taking advice. There were a couple of start‑ups that were great at taking advice and they were performing brilliantly – they made building a start‑up look easy! So that started seducing me into getting back into it.
Over the course of those few years, I had a few founders reach out to me, trying to recruit me. None of those opportunities really interested me until my friend Matt Watson approached me. He explained the problem he was having running the wholesale business for Foxton Fizz. So I started helping him. He wasn’t a tech guy, so I had to get back on the tools to help him and that was an incredible feeling, using those muscles again. My brain and my passions got reignited. To help out, I did customer research and I loved the people and brands I met – I was really inspired to help them improve their businesses. Then I started asking other tech people to work with me on the problem, and I realised how much I missed collaborating with people building things I knew would change the world.
At that point, I was hooked back into working on a start‑up. But even then, my plan wasn’t to do it full‑time. I proposed doing two or three days per week to help get the business on its feet. I quickly found out that I don’t do things by halves! I’m an all‑in kind of guy.
Overall, I absolutely love it. It is definitely all-consuming, and it can be very stressful at times. But I love creating and building products, brands, teams and companies. I love solving problems and seeing the impact on people, businesses and the world – at scale.
This is work that I’m actually spending money to do! Since it’s a start‑up, so far I’ve invested a lot more money into the business than I’ve earned – obviously with the plan of getting a large return. For me, just building this is a huge return on its own. There are definitely some days I wonder why I put myself through it all again. But I can’t imagine sitting around by the pool all day. And the swell where I live just isn’t consistent enough to surf most days.
Over the last few months, I have had the great pleasure of working on a strategy project up in Samoa. It’s been great fun - interesting, challenging, meaningful work with good friends who I can learn lots from. We blended field research, desk research, stakeholder workshops and interviews, and financial modelling to create a five-year strategy and funding model for a not-for-profit focussed on growing Samoan businesses.
I did not catch this fish
As this project winds down, I’m looking for the next organisation to help. If you need support with strategy, research, ‘North Star’ workshops, or cooking a large fish in a small hotel room, get in touch. As regular readers know, I’m “un-retiring” and, like Philip, hoping to put my skills and experience to use.
