First, Some Context

Or How Trent Wound Up Retiring in the First Place

Early retirement crept up on me.

Here’s the helicopter view of my career: In 2003, I co-founded Optimal Usability with Sam. A decade later, I stepped down as CEO, and we sold the business the following year. After that, I became the Chief Product Officer at a startup and later held an executive role at an online classifieds and marketplace business called Trade Me—much bigger than eBay in New Zealand—where I stayed for four and a half years. My last position before retiring was as the CEO of a not-for-profit called Summer of Tech, filling in for someone on maternity leave for a couple of years.

Me with some of the Summer of Tech crew, December 2020

Shortly after starting at Summer of Tech, my marriage, and life, fell apart.

I vividly remember attending a job fair in Auckland, the first one of many that I’d go to, encouraging students to sign up for summertime internships. I’d give the sales pitch to student after student, and when there were lulls in the crowds I would go into the bathroom to sob. My eyes were already red from not sleeping the night before, I wondered if my colleagues thought I was stoned.

You might wonder why I didn’t quit or at least take some leave (and there were chunks of time when I was AWOL) but the truth is that Summer of Tech was a refuge. A job that was low stress, but that occupied my waking hours so I could have some relief from the chaos in my head. (Also, yay for sleeping pills, anti-depressants and a great psychologist. And friends and family, of course.)

So, I didn’t plan to retire after Summer of Tech. But given that I was newly separated, with the kids half the time, jumping back into a demanding C-level role didn’t feel right—for me or them. I didn’t want to hand the kids over to after-school care or a nanny. And my head wasn’t ready to tackle a big job. Instead, I thought I’d make up for the long hours I’d worked during the kids’ early years, spending more time with them and filling the rest of my days with consulting, advising, and board work. I did some of that, but it wasn’t enough to fill my time—not even close.

And so, without meaning to, I slipped into early retirement in February 2021. The transition was rockier than I’d expected, as I’ll share in the next installment.

P.S. How could I afford to not work? The short answer: I sold two businesses I founded and had a couple of smaller startups return 7-8x. More on that later.