What time do you wake up?

Typically, around 7

What kind of work do you do?

I am one of two managing partners at Dovetail. Dovetail designs, builds, grows, and invests in technology firms across Australia, NZ, and the US. As an example, we’ve helped design and build Afterpay’s consumer-facing web and mobile platforms and have helped them grow by more than 50x since we started working together in 2017.

My day to day involves strategy, sales, hiring, investment decisions and advising clients.

What’s the ideal way to start your day?

First a strong espresso then exercise – either a surf or going for a run.

Do you have any morning rituals?

Coffee and exercise. The exercise is occasionally skipped, the coffee never.

How soon do you begin doing work-related things each morning, such as checking your phone or emails?

I will typically open my phone and check Slack as soon as I wake up for a quick pulse check on the day. After exercising is when I’ll dig into emails.

What’s your media consumption or interaction like – which podcasts, radio, videos, books, magazines, and new sites do you read or listen to?

My content consumption has gotten more varied over time. I’ve always been interested in business and investment strategy and will read everything from dry textbooks to autobiographies, business advice books and fiction favourites such as Trent Dalton and George Orwell. I prefer physical books, magazines, and newspapers as I spend enough time looking at a screen when I work.

I listen to podcasts primarily when I’m running or driving. Some are related to work, some are pure entertainment. I’m a sucker for a true crime series and love NPR podcasts especially How I Built This. For work, I tend to follow This Week in Startups.

What do you think is unique about the way you approach your work?

From the day we started Dovetail we wanted to see what we could build if we really focused on creating one great company over 30 years. We wanted to build something lasting, something that would outlive us.

This long-term focus influences a lot of what we do at Dovetail from who we hire, how we measure success and how we plan.

What responsibility do you have on a typical day? What takes up most of your time?

We have a fantastic team at Dovetail that handles a lot of the day-to-day running of the firm. My co-founder Ash and I are focused on what we need to do to continue to double the size of the firm while ensuring Dovetail improves with scale rather than deteriorates with scale.

Apart from things like strategy, investment decisions and key hires, I also help find new clients. We’re quite picky about who we work with and say no to about 95% of leads which means we end up investigating a lot of opportunities before we find the ones we truly believe in and think are a good fit.

Where do your best ideas come from?

I find exercise is hugely linked with my ability to think clearly. I’ll often get good ideas during or just after exercising.

Reading’s also a good source of ideas. When you’re reading, you’re relaxed and consuming a variety of new ideas. I find reading can prompt new ideas or solutions to current business problems I’m trying to solve.

What has been the most transformational business practice you’ve implemented at your work?

Many firms have incentive alignment issues with their customers and with their own employees. This can affect their ability to attract and retain great people and clients. Our work requires a trusted relationship with our clients and exceptional talent to pull off.

We created Dovetail Ventures, an arm of Dovetail through which we invest in the companies we work with and then redistribute the investment among our whole team. This aligns us perfectly with our clients wherein if they do well, we do well and if not, neither of us do. It also aligns our team with the impact of their work. Rather than just getting a salary, they also own shares in the fast-growing companies we work with. This has been instrumental in building great long-term relationships with clients and attracting the exceptional talent we need to be able to deliver the results we have.

What social or environmental issues inform the work you do, as well as what you’re aiming to do with your company’s overall vision?

Our core social mission is to become a key driver of innovation in New Zealand. There is so much entrepreneurial talent in this country, but the ecosystem and capital markets are less developed than many other countries overseas. We want to help build and fund the companies that will drive New Zealand’s economy.

In addition to that, we’ve helped build and invest in some companies that have strong social missions while at the same time being for-profit businesses. This allows them to scale up quickly and access capital markets to do social good. Examples include:

Provider Choice, an Australian firm which helps people with disabilities seek, manage, budget and spend funding from the government.

Grounded Packaging which is on a mission to replace the world’s plastic packaging with alternatives that are 100% reusable, recyclable or compostable.

What’s the most enjoyable part of your day?

I really enjoy learning about and analysing new company and product ideas. There’s plenty of innovation happening in almost every sector. I love trying to pull these new innovations apart and analyse them to figure out if a new project is worth investing in.

What about the least enjoyable?

I don’t really like public speaking, but I do quite a bit of it!

Do you have any side hustles you’re juggling alongside being an entrepreneur?

From a commercial perspective I pour all my effort into Dovetail, but on the side I’m also involved in helping launch a climate change not-for-profit called The Cobenefits Org. It hasn’t launched yet but is getting mighty close.

What’s your best productivity hack?

The main ones for me are: start with exercise, plan my day before I start, and work in 2-3 hour stints with Cold Turkey, a tool that disables my ability to visit any websites other than about 10 that I need for work.

Do you get stressed? If so, how do you manage it? Do you practice any mindfulness or meditation?

Sure, I sometimes get stressed. If I don’t exercise, don’t get enough sleep, go too long without eating and drink too much coffee then small problems can suddenly start to seem large. If I live relatively healthily then I can cope quite well with stress.

What do you do once you get home? Can you switch off?

I can if I work from the office, but I find it much harder when working from home which happened a lot this year due to Covid.

Going for a run, a surf or even cooking works too. You can’t think about work when you’re focusing on trying to nail that random dish that YouTube recommended you watch.

What do or don’t you eat or drink to maintain your performance throughout the day?

For me the key thing is to make sure I eat with some consistency. If I don’t do any exercise in the morning, then I don’t really get hungry until 3pm but my mood and stress levels suffer.

What time do you go to sleep? How many hours of sleep do you try to get each night? Any special techniques for a good night’s rest?

I try to get 8 hours of sleep a night. I think more clearly, handle stress better and am in a better mood if I get enough sleep. I’m not very good at falling asleep though. A good surf tires me out enough that I’ll fall asleep instantly. I’m also currently reading what’s essentially a textbook about the world’s historical debt crisis – 30 mins reading that usually does the trick.