Ask Me Anything

Ten Questions, Ten Answers

These questions have been lightly edited for readability.

What’s the one thing about early retirement that still nags at you or leaves you feeling a bit uneasy?

Ever done the Gallup StrengthsFinder assessment? It’s based on the idea from positive psychology that we should focus on amplifying our strengths, rather than just fixing our weaknesses. The assessment itself is 177 questions designed to identify your top strengths. One of mine is Significance, which describes people motivated by a desire to do work that matters and who want to make a big impact (and be recognised for it). People with Significance push for excellence, aim high, and want their contributions to be noticed.

…Which is kind of the opposite of retiring early. It means that I constantly question how I’m contributing to Wellington, New Zealand Inc, or to the world in general. It sometimes feels like I’m selling myself—and, dare I say, the world—short by not making a meaningful contribution. Everyone has their own unique skills and experiences, and it nags me that mine aren’t really being put to use.

How do you navigate having more money and “free” time than most of your friends and family? Do you ever feel obliged to pay?

The free time is easy, I typically don’t invite my working friends to hang out during the work day. (The exception is a mountain biking group, where four of us manage to carve out time on a Friday morning).

As for money, it’s never really been awkward. Maybe it’s because my closest mates have known me decades, so there’s nothing to prove. (Although I had a girlfriend a couple of years ago where it was awkward. She was living paycheque to paycheque and we would sometimes go out with friends who would talk about upcoming overseas holidays, that kind of thing, and she said she found that uncomfortable.)

I never feel obliged to pay. I have gifted money to family before, but it was always just that—a gift—with no expectation on either side.

I'm curious about your wider family dynamics, especially your connection with siblings. Have you been able to apply any of the learnings you have about community and value/purpose building with them?

I have two sisters living in the Bay of Plenty (where my parents are as well) and a brother in London (hey bro 👋). We all get along, but we’re not especially tight-knit—which is probably why I haven’t talked much with them about the themes I’ve been writing about.

Lately, though, I’ve been trying to be more intentional with family, especially my parents, who are now 76 and 80. We live about seven hours’ drive apart, so we only catch up a couple of times a year, but I’m making an effort to up that.

Have you considered writing a version of this for your kids?

Short answer: no, but it’s an interesting idea. That’s actually how The Simple Path to Wealth came about—the author wrote letters sharing his best financial advice with his daughter. Might be worth a go… let me think on it.

One thing I noticed was limited discussion of personal development beyond learning. Have you explored therapy?

Yes, twice. The first was with a psychologist when my marriage was falling apart, which really helped me work through the trauma. The second was earlier this year with a psychotherapist, after a couple of mates suggested it when I wrote about feeling guilty over my semi-charmed kinda life. That second time, to be honest, I think we were both wondering why I was there. 😂

Not true in my case

Have you thought about courses for skill development? I found myself atrophying without the professional development I used to get at work, so I'm now consciously seeking that out

I’ve dabbled over the last few years: a couple of DJ courses from Crossfader, 100 Days of AI, a parenting course, the Masterclasses from Icehouse Ventures, but nothing too serious, structured or long-term.

How does your 'work' bucket look?

I don’t have a whole lot on work-wise at the moment. I mentor startup founders, help run the Wellington Startup Collective, and do the occasional coaching gig (which tends to be with mid-career professionals at corporates). I used to do more governance work, but am not currently serving on any boards. I also seem to specialise in running ‘North Star’ workshops for professional services firms to help them get a better grasp on their longer-term vision.

All up, though, it doesn’t take up many hours. (So let me know if you have anything interesting for me to do!)

To be honest—and this is a spoiler for next week’s post—I’m seriously considering un-retiring.

How do you value your startups?

I usually value each investment with a low and high estimate in my spreadsheet. Those numbers are typically:

• $0 - if I don’t think things are going well and the business is likely to go under, I make sure I indicate that on my spreadsheet.

• The money I invested - this is usually a conservative, middle ground and is often my default low number. Or, if things aren’t going well I use $0 for low and the money I invested as high.

• The latest valuation - when the valuation gets updated—most often when a company has raised a new round—I will use the updated number.

• A multiple of the money I invested - only used as my high estimate if there’s a decent chance of a positive outcome.

Honestly, the whole process is pretty “ish” and far from scientific—which feels about right, as valuing early-stage businesses is often guesswork.

What are your thoughts on funds versus direct investing?

I used to think direct investing was the way to go: you pick the companies yourself, get to know the founders, sometimes even get asked for advice, and don’t pay management fees.

But after a number of investments went belly up over the last 18 months, I’m less sure this is smart. My bets were too big and spread over too few companies, which is the classic rookie mistake (and somewhat fixed by investing via a fund). The dream of living vicariously through founders rarely happens either. I’m wary of offering advice unless asked, and most startups have more than enough advisers already. Occasionally I get asked to help, and I’m always happy to share contacts or war stories, but it’s rare.

For the record, I have invested in one early-stage fund, ArcAngels Fund II, a small $20m fund which is specifically targeted at women founders in New Zealand.

I’m curious about your Wi-Fi scale—how do you find it helpful?

I’ve just switched to the Garmin Index scale (I’ve owned a Qardio for years) - not because it’s better than others, just because it plugs into the Garmin ecosystem I'm part of.

As for the main benefit, there is research that says daily weigh-ins helps keep healthy eating front of mind, and that’s what I’ve found. It just makes me more conscious of my weight and habits. (By the way, if someone has an unhealthy obsession with their weight then the recommendation flips - they should NOT weigh themselves daily.)