• "Back then, the US scholarship avenue was still quite new for New Zealanders; only a handful of people such as Ryan Nelson, Simon Elliott and Tony Lochhead had done it. There were no digital links or easy ways to share highlights, so my dad brought a huge camcorder to a Napier under-19 tournament to film my games."

  • "I recommend that [US] path to anyone. The infrastructure in the US is just unbelievable. The best-case scenario is you leap into a professional team, but the worst-case scenario is that you bounce out with a degree."

  • "Looking back, poker is just problem-solving. You use the information you have to make the best decisions and learn from the experience. It also gave me a very high-risk tolerance, which has been massive for my business career."

  • "I have a very high-risk tolerance, and I’ll be the first to admit that I love a gamble. At that stage in my life, I had no responsibilities, a deep desire for a thrill, and I was looking for the fastest avenue to get out of my parents' house."

  • "Being able to write, interview, and identify good information is a foundational skill. Even with AI (artificial intelligence), good writing stands out. AI can create "slop," but if you know how to structure thinking and research, you’ll always have value. Trust is becoming the most valuable currency in a world where it’s hard to know what’s real."

  • "I didn't realise it then, but working at the Herald was building the exact foundational skills I needed: knowing how to interview, identifying good information, and writing engaging headlines to get people to click."

  • "I told Shay we were starting a podcast, even though I don’t think he even knew what a podcast was at the time."

  • "I was inspired by Tim Ferriss and his method of deep research and questioning, so I went to JB Hi-Fi, bought a $220 Blue microphone, and we set it up in my garage on a rugged old desk."

  • "It made me realise that there are parts of people's lives that you are genuinely curious about, but there is never really the right time or place to bring them up. When you officially invite someone to talk about their life and put a microphone on the table, you essentially get permission to ask whatever you want."

  • "While that multi-platform approach might seem obvious now, five years ago, not many people were doing it that aggressively. It was an incredible foundational piece of the business. Today, those channels have grown to between 40,000 and 70,000 followers each and have become a huge part of our actual revenue stream."

  • "I saw a path where it [the podcast] could be full-time, but I had to back myself to sell it. I told Shay, "I’m taking the risk. I need to be paid a salary, and you need to work for free until I bring in enough money to pay you full-time". He agreed, and he was full-time within six months."

  • "While it might look like a huge jump from the outside where I left a job while having four kids and a significant mortgage, it just made sense at the time. I didn't just walk away blindly; I phased my exit by dropping down to two days a week at the Herald for a few months to ensure I could make money before taking the "training wheels" off entirely."

  • "My advice is that you need to see the pathway for your side hustle to become fulltime."

  • "The best thing we have ever done is surround ourselves with people who are smarter than us."

  • "Whether it was learning how to write a CEO report or understanding cash flow, I’ve just tried to embrace the attitude of a constant learner."

  • "It [the podcast] has taught me that you can build something cool, but you must recognise the limits of your own knowledge and seek out the experts who can help you scale it."

  • "I realised that a podcast, as we’ve built it, relies entirely on Seamus and me being "the talent". In that sense, it’s not a business; it’s a practice. The second we stop turning up, we stop making money. I wanted to protect against that by building entities that weren't solely dependent on my hands-on involvement."

  • "We’ve become much more selective. We realised that if we couldn't give a project the time it needed to succeed, it wasn't worth doing."

  • "For anyone building their own business, there is a stage where you must fight through a specific barrier: if you aren't the one doing the work, it simply won't get done. However, to reach a point where you can hire someone else to do it, you have to make more money, which usually requires you to keep doing that work yourself."

  • "My natural style tends to be quite chaotic, so I’ve had to consciously learn to become more structured and process-oriented to ensure the business can function without me being involved in every single task."

  • ""Phoneless Saturdays" have been life changing. I turn my phone off on Friday night and don't turn it on until Sunday. Being uncontactable is incredibly freeing. I have four kids at ages where they just want to spend time with me, so although I’m working or away Monday to Friday, nothing should trump them on a Saturday."

  • "Whether it’s Lisa Carrington or Geoff Ross, they consistently show up when others wouldn't. They are also exceptional communicators, and I don't mean just talking; I mean listening and making others feel empowered."

  • "You can see through it immediately if someone isn't being legit. When someone like Mark Stafford or Liam Messam is fully themselves and comfortable being vulnerable, it’s contagious."

  • "My advice is to spread your wings and see as much of the world as possible so that you have a massive frame of reference for when you do finally decide to settle down somewhere."

  • "I worked at the Herald for 12 years and never even knew I was a good interviewer until we started the podcast, and I committed to getting better at it. My philosophy is simple: find something you enjoy doing enough that you’d do it for free and then find a way to make money from it."

  • "More seriously, your 20s are for taking in as many experiences as possible. It’s a tricky, messy time for everyone, and you won't have all the answers. If things get choppy, just stick with it and be kind to yourself."