Richards originally trained as an accountant, working for Arthur Andersen until he and wife Michelle purchased their first business, an optometry practice in Wellington.
Richards says he loves business but quickly realised counting other people's money was not his scene.
Living in a draughty rental, the couple spent their $10,000 savings on lawyers' fees and the remainder of the money to buy the business came from re-mortgaging his parent's house, and from bank loans.
"I'm still so grateful to my parents for doing what they did for us," says Richards. "They aren't rich at all and had everything to lose."
Michelle, an optometrist, worked in the business while Richards managed the marketing side.
At a time when people could expect to pay about $600 for new glasses, Richards introduced $299 package deals and "thank you" packages for customers.
Referrals went through the roof, a cheap way to build a business, he says.
By the third year of business, sales were up 250 per cent, profits up 350 per cent, they had no more debt and had bought another optometry business.
But inexperience and the stress of having his dad's house on the line led to mistakes, particularly when managing staff.
"They say to go and learn all your lessons on other people's businesses so they bear the cost but we were learning the lessons in our own business so we were having to suffer all the stress of our own mistakes, ignorance and naivety."
Three weeks after taking over the second shop they had lost four out of five staff, with one poorly managed dismissal costing Richards a trip to the Employment Court.
"I had to take my chequebook in my back pocket and I had my lawyer on one side and my wife on the other."
Five years later, with a chain of three shops, they sold out to OPSM, "making millions", says Richards.
Michelle wanted to start a family and having seen overseas trends, Richards knew it was only a matter of time before the arrival of cut-price SpecSavers would re-shape the industry.
For his next venture he teamed up with Asantha Wijeyeratne in 2004 to launch SmartPayroll, a software-as-a-service offering that automates payroll functions.
"We had a cloud-based system when a lot of people were on dial-up internet connections so it was not an easy sell. The word 'cloud' hadn't even been invented; people were just still using PC-based software.
"It was difficult for the first five years but now the tide has changed. The momentum started once Xero came on the scene and started spending $10 million to $15 million a year on marketing."
Selling a chunk of the business to Datacom in 2008 gave Richards the "pocket money" to buy a food company importing rice products from India.
Richards says once the Australian former owner hopped back on the plane with his money it was about learning the business from scratch.
But what started as a business challenge quickly became a business nightmare.
The global financial crisis hit and within three months of purchase the NZ dollar went from 75USc to 49USc, meaning the cost of his stock soared.
"I was just so pleased the New Zealand dollar bounced back up again quickly. I couldn't have lived below 50 US cents for long."
The slow payment cycle, sometimes stretching out for nine months, dealing with the Indian business culture and with the supermarket chains made it a difficult business to be in.
After introducing a popular rice-based meal range, boosting profits and getting it into supermarkets, Richards says he had worked all the magic he could and sold the business in 2011 for $2.7 million.
"The confidence I got from making a success of that business, especially through the global financial crisis, was massive. I felt pretty good after that. I still do, every day."
For the past 12 months he has gone back to his roots, co-founding Smart Business Centre, a chain of accounting practices with a difference.
As well as traditional accounting services the 10 Smart Business Centres around the country offer business growth advice.
Richards says all his businesses have had a positive growth trend in common.
"I don't really want to buy a sinking ship because it's too hard to turn around," he says. "I like the tide with me, I like the tail wind."
Something Richards will be hoping for when he competes in the Kona Ironman on October 13.
