In a cut-throat business world, his vast personal wealth did not come from being scared to take on the big boys.
And when it comes to football, Burnley's chairman exudes the same confident belief; insisting his beloved football club can defy the odds and come out on top.
It's fair to say that Kilby is currently in the midst of his first real 'crisis' since seizing control of the Clarets six years ago.
The threat of administration last February was only narrowly averted by the chairman dipping into his deep pockets and supplementing another whopping cash injection with some hasty fund-raising.
Following that, Kilby was forced to make what he openly admits has been his biggest decision as chairman - ending the reign of Stan Ternent.
Now, while seeking a new manager and retaining a vice like grip on the Turf Moor purse strings, Kilby is still setting his sights high next season.
"Just by being smart, I really think we can get up there," he insisted. "I think we have strength in some positions and we have a chance of getting a decent team out.
"If you asked other teams in our division if they would like Robbie Blake, Ian Moore, Richard Chaplow and others in their side, they would say yes.
"We may be down to eight professionals, but there will be another eight coming in. What I would also like to see is some of the kids coming through now - that's what clubs like Burnley have to do."
Kilby has ploughed around £5m of his own cash into the Clarets, fully entitling him to make huge decisions he feels are best for the club.
And he warned that, despite encouraging advance season ticket sales and a levelling out of the club budget due to many player contracts' expiring, more tough decisions may need to be made in the coming year.
"It has been a trying season - probably the most trying since I've been here," he confessed.
"We only just avoided relegation and the big decision was clearly deciding Stan's future. That was always the big one looming.
"But at least the fans now know where we are going."
Kilby added: "We have done fantastically well to fill that cash hole and it was a classic example of Burnley pulling together.
"We had a better cup run that we thought and we ended the season with a few good gates.
"The combination of that allowed us to cut into the shortfall and get us through. Now the season ticket sales for next season have helped immensely.
"Everything is geared around our net income of around £4.5m and one of the planks of that is season tickets, budgeted at £1.5m.
"It is looking increasingly like we have that plank in place, which is nice to know. Then there is £1m for walk-ons, which we achieved this season. TV money comes in around £700,000 and then hopefully there will be an improvement in appearance money next season.
"That can make a massive difference. Last year we earned just £10,000 and that totally wiped out our advantage over someone like Crewe, which is a ridiculous situation. Just two home games equated to £120,000, which is a class player, and that's the difference we are talking about.
"So the budgets are still tight and they will stay that way for a couple more years yet.
"That said, it's up to us to work as well as we can within it."
Next season's First Division already looks a tougher proposition that last year. Leicester and Wolves both have big backers and will have their sights set on an instant Premiership return, while Leeds will always be a city club with huge ambition.
In addition, Plymouth and QPR can also be expected to make a fist of things after winning promotion.
Kilby said: "Let's not kid anybody, there are some big hitters in this division next season.
"If you look at the sides coming up, they have potential, while the sides coming down are a lot smarter than they once were.
"The likes of Coventry and Sheffield Wednesday have struggled with their debts in the past and now they are smarter people.
"Leicester and Wolves will come down with their squads more or less intact and with a wage bill many times our own.
"There is only Leeds who are the intriguing team that might be seriously weakened. But even so, all three are big, industrial cities and we are really fighting hard to punch above our weight."
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