That has resulted in staying connected to rugby working for Sky, starting the JK Foundation for mental health, a workplace health company called Mentemia (Italian for My Mind) and now what he describes as investing in people with "cool ideas around my passions."
He had exposure to the tourism industry after working as an "ambassador" for Auckland Tourism, Events and Economic Development and liked what he saw.
"You see these cool New Zealanders out there doing it. Being able to help these people grow and spread our message is what appealed to me," he says.
He reckons this country is a bit like the "world's bach" for tourists.
He met one of the investment company's founding partners, Jason Hill, when the pair were in Japan at the beginning of the decade, Kirwan coaching rugby and Hill working for Tourism NZ.
Among them the founding investors — including former Air NZ corporate development team leader Jonathan Cameron — have committed $500,000 and Kirwan says he's happy to have "skin in the game".
He doesn't have a hands on, day-to-day role but already he is challenging the founding partners to think outside the square. As Hill puts it: "We're subject experts but sometimes we need to have someone who can helicopter in."
Kirwan says he's not necessarily expecting to get rich from the new venture but sees the strong profit potential.
"Someone asked me what I do the other day and it's really hard to put your finger on it. There's tech entrepreneurs, property entrepreneurs but I think I'm a people entrepreneur.''