Planning for retirement can be scary. Whether you're buried in debt or have consistently put away 20% of your income since the age of 20, there's always someone out there telling you that you'll have to spend your golden years greeting shoppers at Wal-Mart (not that there's anything wrong with that) to maintain your lifestyle.

There's also a lot of conflicting information about financial planning for retirement. Articles abound that scold individuals for their poor saving habits, yet too much of this advice is based on the assumption that lower-income people have huge amounts of cash to work with. We're told repeatedly that small savings can produce big gains over time, although much of that conventional wisdom comes from the same mutual fund companies that charge excessive fees and take a big portion of those pennies that are supposed to make all the difference.

So when I heard fledgling retirement planning site BoulevardR present at a recent VC Taskforce event, I was immediately drawn to its premise of targeting that sizable market of people who have less than $500,000 in assets. The startup aims to provide customized advice based on lifestyle and retirement goals (everyone knows half a million bucks goes further in Oklahoma City than in San Francisco and that setting up a philanthropic organization will probably cost more than spending your retirement with family). The site, which just did a soft launch in October, seeks to offer realistic retirement planning advice based on the way ordinary people save and spend.

When I later spoke with CEO Matt Iverson, he equated the terror most people feel about retirement planning to the way an overweight person avoids the scale. Iverson founded the company with his dad, Jon Iverson, a former service provider for E*trade Financial Corp. who was able to retire at 50 with the help of stock options from the brokerage. We spoke for an hour and I nodded in agreement when he talked about how most financial planning sites offered biased, or impractical savings advice, or just ignored the sub-$500,000 asset market since they couldn't make large commissions from that group.

"We're trying to create a nonthreatening environment for consumers to figure this out," Iverson explained.

BoulevardR's revenue model is based on advertising, but it also incorporates a user review and feedback system that it says will help users get objective advice. The startup offers its own twist on the standard retirement calculator by mixing images with numbers to keep people engaged. For instance, while this calculator requires you to enter your age and income, debt and savings levels, it also asks you to prioritize a series of pictures that represent your idea of retirement (travel, back to school, family time and spirituality to name a few) as well as your immediate financial goals (save for a car, invest better, have a child or remodel your home).

It all sounded like a great idea ... until I got off the phone and ran my own numbers on the site's retirement calculator. It told me that if I retired at age 65, I would run out of money by 69, and not even be able to spend much of those intervening years with family, one of the priorities I'd listed. It also said I ranked in the bottom 6% of all people in my age group in terms of retirement savings.

This might have been enough to send me instantly to an early grave, if I didn't realize that the calculations were just plain wrong. Granted, I've never made millions on stock options, but I have always saved a chunk of my income. With decades to go until retirement, I'm still saving and starting to see the magic of compound interest. I know there are plenty of people who have a lot more money than I do, but I've also read the national savings and debt statistics and I know there is no way that I could fall in the bottom 6% of all retirement savers.

I went back to Iverson, who had worked in consumer rights and advocacy before starting San Francisco-based BoulevardR, and asked him if the team was still working out some glitches on the retirement calculator. He told me that BoulevardR's way of forecasting retirement savings could be superior to other calculators out there because it "tries to more realistically simulate all the impacts on retirement calculations than any other tool available." He said that my exceptionally weak results could have been based on the fact that I listed buying a house as one of my future goals.

It still made no sense to me, based on my own income and savings levels. And after a quick look at the calculations, I was pretty sure I had identified the source of the problem. BoulevardR drew a graph showing that my savings would steadily decline from this day forward regardless of how much I earned and saved in the future. It was like they were putting me into early retirement.

When I asked a group of financially responsible friends to try it out, they got similarly horrifying results predicting that their cash would run out well before age 75 and that there would be little or no time to spend with family in the meantime. Huh? I mean, how much does it cost to watch a video together? Even stranger, when I entered my same basic numbers later in the afternoon and switched around my retirement goals a bit, my ratings changed dramatically, ranking me anywhere from the lowest 1% of all savers to the top 7%.

Had Iverson said up-front that there were still major problems with the site's retirement calculator, I would have understood. The site remains in beta, after all, and Iverson was clear about wanting to spend more time fine tuning it before pursuing venture funds. I do think the concept is excellent, as did many people last week at the VC Taskforce event, where Iverson made a 90-second elevator pitch.

"I don't even understand it, but I love it," Gary Benton, a partner with the law firm Pillsbury Winthrop Shaw Pittman LLP said at the time.

Still, over my repeated exchanges with Iverson, I started to see BoulevardR as a symbol of many of the things that go wrong in the startup and venture world. I found it odd that he would not admit that the calculator was seriously flawed, even though it was depleting my savings decades ahead of time. I also found that all the features designed to set the site apart appeared on closer look to be more like gimmicks than effective financial planning tools. How could it tell me I wouldn't have any time to spend with family, when it didn't even know if my idea of family time was sitting on the porch or worldwide travel? I understood in a new way that common VC admonition to startups to come clean with existing flaws or glitches in the site: They may not be exposed during an elevator pitch, but they emerge over time.

If BoulevardR can clean up its calculators and attract users and advertisers, it could be onto something big. In the meantime, though, it reminds me of some of those Web 1.0 bubble era wanna-be companies challenged to execute on what could in theory be a great business. - Andrea Orr