What do you consider popular success? Quicken for Windows sold over 1.5 million copies per year for over a decade and has probably anywhere from 3.5-5 million active users on a currently supported version right now. In productivity software, it was always either #1 or #2 for retail software sold year over year.
I would say that is relatively successful for a piece of packaged software, but in the web world, it's tiny compared to Linkedin, Facebook, Youtube, Zynga.
A few rambling observations from years spent working on that business:
Quicken doesn't help you do any better with your finances. It gives people who are already able to manage their finances an easier way to keep score.
If you don't know how to manage your finances, Quicken won't help. It's the equivalent of the scale for finances.
Personal finance is exactly like dieting and weight loss. You have to make many short term decisions without an immediate benefit that result in a longer-term benefit.
The weight loss industry is huge, but Americans' are still fat.
Most people are not interested in managing their personal finances or feel that what their bank website delivers is more than enough.
Quicken isn't transactional you don't actually pay your bills from Quicken. Yes, you can do quicken bill pay or pay for bank billpay but very few do that. Since it isn't transactional,
you don't need to use it.
Quicken doesn't solve any 'must do' jobs in personal finance. You can't pay bills, transfer funds, buy or sell stocks, pay anyone, fund an account.
You have to go elsewhere to do any of those functions. If you are an investor it is pretty much the only game in town for easy tax lot tracking and reporting.
A quicken is a tool for those people that are responsible, disciplined and motivated to manage their finances. It isn't a tool that's going to motivate anyone.
I think the success of products like Zynga (hi, let me blow money on a useless game where I plant crops) relative to the small success of products like Mint
(let me use a free product to track my spending and check balances ) says more about what's important to the average consumer.
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