Interview with Brandon O'Brien, Creator,

Related Website(s)
Related Blog:Brandon O'Brien
Interview Date:Feb. 20, 2007

Lots of folks, it seems, are looking for a reason not to purchase Quicken or Money.

I can say this because one of the most popular pages on IYM is my article regarding Alternatives to Quicken and Money. As much as I love these programs, I absolutely understand why folks often run screaming at the thought of using them. And paying for them. I've been a Quicken user since the mid-1990s, and if anyone knows how little of Quicken can still be called "simple," it's me. Sometimes just getting it to set up and track your checking and savings account balances can be an ordeal.

And who wants an ordeal? Certainly no one I know.

They just want to manage their checkbook.


Build It and They'll Come:
Brandon O'Brien, Creator,

I offer it for free because I believe you shouldn't be charged to manage your money. I think that's the reason a lot of people don't try to manage their finances. They don't want to pay for some bloated software (like Quicken or Money) when they just want to track their spending and set up some simple budgets.
— Brandon O'Brien

Which brings us to what people are willing to do.

Lots of them, as we know, are perfectly willing to ignore their spending and account balances altogether, believing that "everyone does it this way" and that "things will work themselves out" in due time. (Which, of course, never happens.) Some of them are willing to use Excel spreadsheets (like — ahem — my Check Register spreadsheet) as a starting point. And now more and more folks are turning to online solutions like ClearCheckbook.

ClearCheckbook is a pretty new player on the financial-software scene, but it's gaining converts quicker than your local bank can dish out a round of overdraft fees. ClearCheckbook offers a free way to manage your checkbook and other accounts online. You can also categorize your spending, set up reminders, build a simple budget — and do it all remotely, without the need to install any software or attend night classes to learn how to use the interface.

Who in the world would offer such a thing? Well, Brandon O'Brien would. He's the brain and brawn behind Clear Checkbook. And frankly, I think he's still too young to understand the value of just what it is that he's built.

And he's got some really interesting stuff to say.

Brandon, you've mentioned that you didn't start ClearCheckbook with the intention of building a website for others to use — that it was just for personal use. When did you figure out you might have something "bigger" on your hands?

I realized I might have something good in my hands after I was encouraged to release it for multiple users. I did some research online and looked for similar projects that were currently in the works. At the time, the only similar site I could find was After learning about Mvelopes, I realized sites like theirs would be what helps mine succeed. People don't want to have to pay to manage their money. If I could provide them with a similar service for free, with an easy and intuitive interface, there's no reason people should want to turn it down.

How would you describe your own money philosophy? Do you enjoy managing your money? Have you ever done anything with your money (or credit) that was really dumb?

I've had jobs since I was 12 years old. I started out as a paper boy for my neighborhood, detassled corn in the summers during junior high, worked at book stores and office-supply stores through high school, and had a variety of jobs in college. From the time I opened my very first savings account back in junior high, my mom taught me how to keep track of my expenses in my register. She taught me about balancing my checkbook. "Jiving," she called it. Which is why I labeled my balancing feature "Jive" on ClearCheckbook.

I love the idea of being able to wake up and know that I'm making a difference in peoples lives by the services I provide.
— Brandon O'Brien

I have always been somewhat obsessed with seeing where my money was going and knowing how much I have in my account. It was never too big of an issue until I got in college and opened a credit card and a new checking account with a local bank. Now instead of tracking the occasional purchase from one account, I had three to keep track of.

This is when I realized Excel wasn't working too well for me. At the time, I didn't know enough about web programming to think to write my own program to keep track of my money, so I kind of let my organization slip. I had a few dumb things happen, as far as overdrawing an account and getting charged some outrageous fees. I learned quickly that some things needed to change, so I opened up Excel again and tried my hardest to make it work. After the eventual frustration and learning some more about web programming, that's when I started working on my banking app (at the time I simply called it myBank).

Most young adults around your age run in fear from the "B" word. Do you believe in budgets, in planning your spending to attain specific goals? Do you follow a written budget yourself? Why or why not?

I think budgets are a great way for people to manage their money. I know a lot of people think badly of them, but they really can help you keep track of where your money is going. If done right, you can really save money as well. I set monthly limits on my spending for different categories. Right now I'm using them mostly as rough guidelines, as I just moved to a new city and got a new job, so it's taking me a while to adjust from the "college mindset" of spending to the "real-world" way people spend. I do plan on eventually setting a strict budget and sticking to it each month.

Do you have much interest in personal finance outside the realm of Clear Checkbook? Do you read money blogs, or do the works of any particular financial personas appeal to you?

I've always had an interest in money and finance since a young age. I remember mowing the grass and collecting the money and using my parents ironing board to iron the bills so they would fit nicely in my wallet. I've also always been a bit of a penny-pincher, always trying to find the best deals for things before making a purchase. I subscribe to a few productivity blogs and read the tips and advice they have.

I've always had a bit of an entrepreneurial spirit and have had dreams of opening my own web development company. I love the idea of being able to wake up and know that I'm making a difference in peoples lives by the services I provide. I've received countless emails from ClearCheckbook users telling me how they haven't bounced a check since they started using my service or that they never realized how much they were spending on certain areas and have cut back and it's saved them a lot of money. I would love to keep providing new services that help people as much as ClearCheckbook does.

In your mind, what's the greatest impact the internet could have on the personal finances of average folks? Can you see any ways in which it (or technology) could be more detrimental than beneficial?

I think the greatest benefit the internet has on personal finance is the readily available wealth of information on budgeting, credit cards, debt, savings, and so on. Where before you might have to talk to your bank or a professional, now you can get tips from people all over the world on how they manage their money, and then use their advice to form your own methodologies for saving. The internet also brings sites like mine into play — people can now update and manage their finances from anywhere in the world. If they're not by a computer, simply text message the site with your cell phone and BAM! — no need to worry about carrying around a wallet full of receipts.

I think the internet and technology can have a detrimental effect on some peoples' finances because they rely so heavily on their online bank statements that they feel like they don't have to keep track of it because the bank does for them. This is one of the biggest questions people ask me about the site: "Why do I need a site like this? I can keep track of all my finances on my bank's website." My only response is that banks can, and often do, make mistakes. I've had several charges to my accounts over the years that are either errors or duplicates. Another thing is that banks don't know when you write checks. If you write a large check and the person doesn't cash it for a few weeks, and you only go by your bank statement's balance, then you can very easily overdraw your account.

And another thing that can be bad about the internet is shopping. People can see so many things, and simply enter their credit card numbers into sites. They spend left and right, and they'll spend themselves into debt without ever leaving the chair.

So far, Clear Checkbook has earned over 2,400 users. That's pretty impressive — and the time and effort you've invested in your site is obvious. What about Clear Checkbook brings you the most pride? What's your ultimate hope for it?

I get the most pride out of ClearCheckbook by knowing that it's making a difference in peoples' lives. When I get emails thanking me for the service, or letters explaining how much it's helped them with their finances, it all becomes worth it. It's also great that what started out as a pet project for myself was able to transform into something that helps so many people.

My ultimate goal for ClearCheckbook is for it to be the number-one place people go to manage their money. It would be great if ClearCheckbook became a household name: Instead of getting out the old checkbook register, you simply log in and keep your spending updated right there. I also plan on never charging for the service. That's one of my founding principles with the site: People shouldn't have to give up their money so they can manage it.

Lots of folks lament the fact that the "biggie" financial software programs like Quicken and Money now suffer from "feature bloat" and are no longer useful (but are, perhaps, intimidating) for the average consumer. What's your take on this?

I know that a lot of users on my site say the same thing. Microsoft Money and Quicken are huge and overly-complicated for people just looking to track expenses, set budgets, and do a few other things. The cost is also another reason people tend to stay away from those applications. They get scared off by the price tag and then never get around to balancing their checkbook or managing their money any other way.

I know that for myself, the price tag was the big reason I stayed away from Quicken and Money. I often use this analogy when comparing Quicken or Money to the needs of most of the ClearCheckbook users: Say someone is looking to go to a party a few houses down from theirs. They have two choices for transportation: a bicycle (ClearCheckbook) or an Apache attack helicopter (Quicken and Money). Sure, they could jump in the Apache, tick off half the neighborhood, and waste 50 bucks' worth of fuel ... or they could just hop on the bike and spend 30 seconds riding down the street.

Most people don't need or want everything associated with Quicken and Money. They just want a simple, straightforward app they can use to manage their spending. For free.

Do you come from a family that talked openly about money, or was your family overall very secretive? Was money a taboo topic in your household (or in the homes of your friends)?

Money was never really taboo when I was growing up. My parents were always making sure I was tracking my spending, that I wasn't using more than I was saving. I can remember one family vacation we went on when I was younger. My parents gave my siblings and I each twenty dollars to use for the week. We could buy souvenirs or candy or whatever we wanted. My brother and sister spent all their money within a few days, and at the end of the trip I had $19 dollars left. The only thing I bought the whole trip was a pack of Starbursts at a gas station.

My parents also taught me how to pay bills at a young age. When I had my paper route, I decided I wanted to get a moped. A good friend of mine had one and I did all the research and found out I could get one for a little under 800 bucks. Well, a 13 year old kid obviously doesn't have 800 bucks laying around, so I loaned some money from my parents and bought the moped. Over the next year or so I would pay them each month from my paper route and corn detassling money. I kept a log book and each time I paid them I would keep a running total of how much I owed. It was a great way to learn about money and budgeting at a really young age.

Tell us your thoughts on why so many people have such a difficult time managing money and debt today. What might we as entrepreneurs, bloggers, and other "involved netizens" do to curtail the damage?

I'll often be talking to people about this and they'll say the same things: "I don't have time to balance a checkbook." "I'm too busy." "It's not that important." "I have faith in my bank." I think people look at managing their money as this huge task that will take hours a week to maintain. In reality, I spend maybe 15 minutes each week entering my receipts and looking at my bank statements and jiving my entries.

I think it's the job of everyone who truly knows how easy it is to manage money to tell other people and get this preconceived notion — that finance tracking is a huge nightmare — out of the way. I think most people who use my site don't spend more than a few minutes each day on it, entering and updating their accounts. At the end of each night or each week, simply take your receipts and enter them into the site. Every week or two, check with your bank statements and make sure everything matches up.

The more people realize how easy managing your money actually is, the more they'll do it, and the more they'll save.

If the internet went away next Thursday, what would you do with yourself after that?

I hate to admit it, but often do, that I really wish I didn't have to work with computers every day. The down side to this is that most of what I know how to do (at least in skills related to getting a job) revolve around the computer. If it did suddenly shut down and we went back to the 19th century in terms of technology, well, I've always wanted to be a geologist. During high school I was in several earth-science-related competitions. I could name off hundreds of rocks and minerals just by examining them. When I applied to Purdue, I actually applied to the Earth Sciences department, but switched to Computer Science (then later again to Computer Graphics) the summer before my freshman year.

You graduated from Purdue in late 2005. With that degree in Computer Graphics Technology, you obviously know what you're doing when it comes to handling computers and cyperspace. But what did college teach you about money?

College taught me a few things about money. The first: No matter how much money you have, you could always use more. With books, courses, partying, rent, food, and all the rest, it seemed like as soon as you got some money, it was gone.

The second thing: Having a girlfriend in college means you also need to get a job. You don't really think about how much money you spend on dating until your money starts to run dry. You don't want to look even more poor than your typical college student when you're trying to impress a girl. Having a 15- or 20-hour-per-week job during college was a great way for me to get the extra spending cash I wanted ... but still have time to study and do well in my classes.

Next week you'll find out that one of the folks you used to deliver newspapers to left you $3 million in her will. What will you do with yourself and your money?

I probably wouldn't change too much about myself. I know the first thing I would do is pay off my student loans. Since I don't have any debt other than that, there's nothing else to pay off. With the rest of the money I would invest it and probably continue to live as I am now. Freelancing on the side of a full-time job. I don't think I'd be able to quit working all together; I'd get way too bored.

Aside from maybe buying a new computer, I don't see myself going overboard and buying a huge house and a yacht or anything crazy like that.