Generation gap alert! Thirty-somethings think about money in different ways. A new Web site is recognizing that fact, and offering users an entirely new money management model, writes MoneyShow.com personal finance expert Terry Savage.

Payoff.com promises to make dealing with money “Simple, Social, and Fun.”

That’s not my usual attitude toward personal finances. Yes, I try to make things simple, but I inherently believe that money management is also serious—and a very private matter.

That’s definitely not the approach being taken by Scott Saunders, a 35-year-old entrepreneur who has the backing of some of the country’s most sophisticated venture capitalists in launching Payoff.com.

And after spending some watching Saunders demonstrate the features of this new site, I’m convinced that he is headed for a huge success in this unique approach to money management.

Saunders’ starting point: “Money is a means to an end. We start with dreams and goals—and then move into money...Payoff.com is about money in the context of life...Dreams are the context that make caring about money worthwhile.”

Lest you think this is just a “touchy-feely” approach to money, let me assure you that this well-built site is a financial data aggregator powered by Yodlee, and offering all the tools and capabilities of current programs such as the desktop Quicken, or the rapidly-growing free online service of Mint.com. All promise to give you a complete picture of your financial data with one click, including how to track your spending.

But Payoff.com takes it a step further. It creates a community of users to applaud and motivate your success, and encourage you when you falter.

Payoff.com is free, like Mint.com. It's paid for by the connections you make to financial advertisers suggested by the site to improve your money-management skills.

So you might be directed to a free checking offering by a bank—or even to a Web site like LegalZoom.com to help you set up that business you’ve been dreaming about.

Goals and Dreams
That brings us back to the “dreams and goals” focus of this Web site. Saunders is building a community of users, who start by posting their dreams and goals to be shared with others.

It’s sort of like posting your “bucket list.” The concept is that the social network “connection” with others will help you reach those goals, through their comments and suggestions—a sort of “dream support group.”

Saunders feels that this positive starting point for money management will encourage people to learn more and do the right things.

“People have no freedom to dream these days," he notes. "They’re in the daily rat race, and they never seem to get ahead financially. We’re showing them they can reach their goals—step by step.”

NEXT: Reinforcement and Rewards

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Reinforcement and Rewards
The entire site is based on positive reinforcement. You earn “badges” for smaller accomplishments along the road to your goals—such as paying off a credit card, or making 25% progress in getting toward your goal, checking your credit score—or even just signing in to check your finances on a daily basis.

Those badges are posted publicly on your site (much as girl scouts accumulate badges on a sash)—and are applauded by others. Every badge earns you entry into a sort of sweepstakes, with “sur-prizes” from participating advertisers.

In short, Saunders has built the total community—motivating and educating individuals, providing revenue for advertisers, and encouraging connection with popular brands.

Money Management by Brand
The money-management aspect of this Web site is also based on psychological rewards. Saunders points out that there are no red warning flags or red bars on charts to remind you that you’re falling short of your goals.

And when it comes to categorizing spending, you don’t get a pie chart that forces you to do all the work.

Instead Payoff.com tracks your spending by brand name! Yes, as your checking account, credit card, and debit card info is securely downloaded into your online Payoff account, it is automatically categorized by the regular brands you use—whether you spend money at Starbucks or Chipotle, Shell Oil or ExxonMobil, Victoria’s Secret, Target, or Old Navy.

You can see which companies you spent the most with, and the most recent transactions. Saunders figures people think in terms of “brand spending”—and that they’ll be more willing to contemplate changing their spending habits to reach their goals.

Quite literally, Payoff.com is designed to change the mindset of an entire generation—a generation raised on credit and debt, and now plunged into despair about their future.

“Debt steals dreams,” says Saunders. “My dream is to help as many other people achieve their dreams as possible.”

Check out his approach at Payoff.com. I think Scott Saunders has a great shot at reaching his dream.