Like its competitor Expensify (an app that I reviewed last year), ExpenseBay can automatically import transactions from credit cards. You can also enter cash expenses via your smartphone (using the free iPhone or BlackBerry apps — an Android app is coming soon), and scan or email photos of receipts to attach to expense items. Once your expenses are recorded in ExpenseBay, you can classify, edit, delete and split them as required.

Generating reports is a matter of selecting items to add to the report — you can do this on an item-by-item basis in the attractively designed web app, or by selecting items that match certain rules (for example, you could make a report of all travel expenses from the last 30 days). You can create as many different reports as as you need, and reports can be onetime or recurring. Once your reports are ready, you can preview them before downloading them or submitting them via email to whomever approves your expenses. ExpenseBay can also integrate with several other popular web apps, including Freshbooks, SalesForce, Quickbooks and TripIt (integrations are only available on Premium accounts).

As everything stored in the cloud (if you’re interested in cloud computing, check out our Structure conference in June) and reports can be generated as PDFs, the system is completely paperless — which should be a lot tidier than the “traditional” process of filling out Excel sheets, printing them out and attaching photocopied receipts. As you can record everything as you go using the mobile apps, it should also do away with the end-of-month digging around in the bottom of your briefcase, desperately trying to find the receipts that you need.

While I tried out the service through a demo account, if you want to use data from a credit card, you’ll need to provide your card’s web site login credentials. Despite the assurances on ExpenseBay’s lengthy Privacy and Security page, this makes me nervous. I’d really like to see the equivalent of oAuth for bank accounts, to allow apps like this to access to financial details via an API without providing any other access to the account.

ExpenseBay has a range of pricing plans. The Basic account is free, and will allow you to import data from one credit card, email receipts and generate reports. The Mobile plan ($5/month) adds the ability to edit expense items and attach receipts to expense items using the mobile apps, while the Premium account ($10/month) includes premium expense report templates, and integration with other apps.

Do you use ExpenseBay (or a similar app) for managing your expense reporting?

My first cost-cutting measure is a big one, because I’m looking to free up a significant amount of cash in one fell swoop, and the timing is convenient. My lease is up in a few short weeks, and so I’m already on the lookout for cheaper accommodation. I live in downtown Toronto, and my place is bigger than one person needs because I wanted to have enough space for a home office. My rent is accordingly quite expensive.

Luckily, working from home doesn’t necessarily mean working from home all of the time, so this time around I’m willing to make concessions regarding space (and location) in the interest of saving significantly in terms of my monthly rent. Instead of a one-bedroom-plus-den, which I have now, I’ll be looking for a one-bedroom place, which in this market might amount to as much as $700 in savings, depending on where I end up relocating.

To make up for the lost space, I plan on spending much more time working away from home. I have a three-part approach to accomplishing this, which should ensure that my routine stays varied enough to remain interesting, and has some built-in redundancy to ensure I always have somewhere to go to work that isn’t my own apartment.

Coworking/External Office Space

The first and primary part of my plan is to use a largish portion of the money I save in rent to pay for a membership at a newly opened coworking venture here in the city. It’s called Camaraderie, and it’s conveniently located relatively close to the area I’m looking to move to. Membership fees are $300 per month, which guarantees you a spot during working hours, including free Wi-Fi and hot beverages.

It’s a deal that can’t be matched by renting office space alone in the downtown area, but if you live somewhere that isn’t a major metropolitan area and that doesn’t have a local coworking space, try looking around for office space rentals, and see if they might not be cheaper than maintaining the larger place you’re using now as your living/work space. You might be surprised at how much money you can save this way. Even the savings represented by being able to choose a lower-cost Internet plan for home and savings on tea and coffee spend are significant.

Museum/Gallery/Library Memberships

The second part of my office/house separation plan involves simply maintaining the library, museum and other public space memberships I already have. Library cards are free in most cases (or at least they are here in Canada) as long as you can prove residence, and museum and gallery annual memberships generally aren’t that expensive.

It’s like having coworking space, except you’ll often be the only one working and it’s an interesting environment. There might not be coffee immediately available, though, which is why step three is a great old stand-by.

Starbucks/Coffee Shop

Never underestimate this old time-tested web working buddy. The coffee shop will save your sanity time and time again. If you’re in a dense urban area or have access to a car, this one should be the easiest of the three steps to get a handle on. My advice is to find an independent place with low turnover, because you’ll get the familiarity benefits of an office setting without all the downside of an actual office.

All told, it looks like I might be able to shave between $300 and $400 a month off of my budget, all by accepting a move to a slightly smaller space and adding some coworking to my routine, something I’ve been hoping to do more of anyway; not a bad cost-cutting measure by any means.

Have to tried downsizing your home office to cut costs? How did it work out?

With the self-assessment deadline for the 2008-2009 British tax year looming this coming Monday, it seems like an opportune moment to round-up some useful tools and services for managing your business expenses. Each year, I find that I’m missing a receipt, I can’t account for a crucial purchase or that paper receipts have literally faded.

Though too late to help my preparations for filing my own tax return this year, the selection below is driven by what’s caught my eye lately and my preference for web-based, iPhone and Mac applications. For the 2009/2010 tax year, I’ll certainly be employing one of the following:

Cha-Ching

Midnight App’s beautifully crafted Cha-Ching almost makes me want to do my expenses! With a playful name, Cha-Ching is very much designed with Macs in mind, employing a gorgeous, intuitive interface and integration with iSync (for scheduling bill payment reminders) and an iPhone edition for mobile use.

I found Cha-Ching’s real strength to be the ability to tag individual expenses, and — like iTunes’ smart playlists — create dynamic standing searches that can, for example, pull out anything you bought from tagged as “Apple” and “business expense.”

ReceiptFarm & Shoeboxed

We covered receipt organisation service Shoeboxed a couple of years ago, finding it to be a great solution for uploading, storing and organising your paper receipts, via a mail-in service. In the time since we last wrote about them, they’ve added a DIY “self-scanning & data entry” plan to their service, along with an iPhone app.

More recently, ReceiptFarm has begun to offer a similar Shoeboxed-style service, based here in the UK. Both services are almost identical, feature-for-feature, though ReceiptFarm appears to be slightly more expensive than its competitor. Also, where Shoeboxed is confident their stored receipts meet IRS guidelines for taxes, its not clear whether UK authorities accept scanned copies of expenses.

Expensify & WebExpenses

We reviewed Expensify early last year; it’s a comprehensive solution for managing and tracking expense reporting. The service is oriented around importing expenses, scanning receipts and generating reports. The service’s killer feature is the ability to generate tax authority compliant electronics receipts for expenses below $75. Recently, Expensify also launched integration features with bookkeeping service Outright.

WebExpenses also offers a similar service here in the UK, and with the likes of E*Trade and Heineken amongst its clients, it appears to have traction within large as well as small organisations. Features are broadly similar, though the service offers an innovative SMS expensing feature, which enables users to expense items as and when they occur.

inniAccounts

Finally, recent weeks have seen the launch of inniAccounts, a comprehensive accounting and bookkeeping service designed specifically for UK-based freelancers.

inniAccounts was created by a pair of engineering contractors, frustrated with the minutae of managing their fiscal data using Excel or complex accounting software designed for large organisations.

The service helps manage timesheets, invoices and payroll, but also include some features for compiling, completing and settling tax returns as well as mileage and expense claims. Uniquely, the service also provides a real-time tax calculation, helping users understand their financial position immediately, rather than waiting to the end of the year.

With only five days to the 31st January filing deadline here in the UK, it’s likely too late to adopt and employ any of the applications we’ve covered here, but they may help streamline your accounting for the coming 2009/2010 tax year, with greater productivity and accuracy.

Personally, after tinkering with each of the options above, I’m leaning towards Cha-Ching, simply because of the playful interface (it makes a difference for such a dull task!) and the immediacy of booking expenses via an iPhone app. However, I suspect something like inniAccounts will be a better long term solution, though I’m concerned that much of this space is occupied by startups rather than established companies, raising questions and doubts about the continuity of your financial data if the company ceases to trade.

Do you have preferred services, applications or methodologies for tracking and managing your expenses and receipts?

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Why Bother

One of the most important reasons to separate your business expenses from any personal money is that you can often write off business expenses as deductions come tax season. Just what you can write off depends on whether you’re self employed or not, but there are some deductions available to employees who telecommute, too. A tax preparer can help you find which deductions apply to you — but he or she is going to want to know what money you spent over the course of the last year.

It’s also important to have a good record of your expenses. In some cases, you may find that an employer or client is already set up to reimburse expenses. And if you find that certain expenses are getting out of hand — perhaps you’ve been asked to travel into the office more than you originally agreed to — you may be able to convince an employer or client that reimbursing you is the right thing to do.

Lastly, it’s easy for expenses to get out of hand if you don’t keep a close eye on them. Even being able to budget for work expenses you have to pay out of pocket can make the process of managing your personal finances a lot easier.

The Nuts and Bolts

How you choose to separate out your work expenses from your personal budget depends on what’s easiest for you. Personally, I found that since I’m self-employed, the easiest option was to open a separate business account at my bank — all my work expenses are paid out of that account and all of my income goes into it. From there, I cut myself a pay check into my personal account as I need to.

You don’t necessarily need a separate checking account for your work expenses, especially if most of your income comes from one source. In that case, something as simple as creating a new category in whatever system you use to manage your money is enough. As long as you can quickly sort out which expenses where for work and which were personal, the exact method doesn’t matter. Most software makes categorization easy. Some even allow you to create rules to automatically categorize certain expenses as work-related.

Another alternative is to use an expense-tracking tool. It can be a little harder to manage the record keeping with this approach, but it does provide a simple solution for many people.

How do you keep track of your expenses?

Image by Flickr user shanechambers

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Traditionally, there’s a lot of paperwork that goes along with ending the year and getting ready to complete your income tax return. You might have to bring together information from several different applications, trying to make a mess of information make sense. WorkingPoint’s new features are meant to make use of all the work you’ve done over the course of the year to minimize the effort you have to do in getting ready to either hand your paperwork over to a tax preparer or to do your tax return yourself. While those features are still being rolled out, they should be in place by the end of the year.

If you’re already using WorkingPoint to manage invoices and expenses, you’ll be able to print out tax reports that directly map your business expenses to the IRS Form 1040 Schedule C (the form used to deduct business expenses), as well as calculate your estimated income taxes and print out 1099 forms for any independent contractors you’ve worked with over the course of the year. Other new features WorkingPoint plans on adding include integration with PayPal, banks and other e-commerce tools. The application also plans to add a payroll service gateway. It is important to note that the new features are only available with a premium account.

As a part of the improvements that WorkingPoint is rolling out, the application’s creators have added a second user to free accounts at no additional charge. While this may not seem immediately useful for some web workers — especially freelancers or anyone else working on their own — I’ve already found a good use for it. By giving my CPA access to my invoices and other business information, I can speed up the process of getting my taxes done as well as help my CPA to provide me with relevant advice about growing my business in 2010. With access to my account, he’s able to print off his own copies of tax reports, without any hassle of mailing them in. And since I don’t have to give out my own password for my account, my business’ data is a little safer.

The new developments at WorkingPoint serve to set this application apart from the other online invoicing tools, simply because few options provide easy ways to take all the business data you collect over the course of a year and turn it into an income tax return. WorkingPoint can save a lot of time when it comes to coordinating income, expenses and the various forms that go along with doing your taxes. If you use a tax preparer, you’ll find that you can get a faster turn around and if you do your taxes yourself, you’ll eliminate at least some of the stress.

If you’ve tried WorkingPoint, let us know how it worked out for you below.

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Though I know no one’s immune from a recession, this conversation made me think about my own approach to the financial side of what I do. I started to think about what, if anything, I could do to try to cushion myself from the current (and future) economic turmoil. Here’s what I came up with.

1. I need a savings buffer.

Much of my work is short contract jobs, so I need to make sure I have enough money in the bank. I’ve seen a lot of talk about having a buffer that would last three months if you were out of work. That will be difficult to achieve, but it’s worth aiming for.

2. I need to pay my debts down, if not off.

Sometimes my credit card can get a hammering, so I’ve decided to pay it off every couple of weeks at the moment. This helps me avoid the “how-on-earth-did-I-spend-that-much” moments of truth that can occur if I leave it longer, and makes it easier to track my spending.

3. I need to track my spending.

I find it hard to save money if I don’t know where it’s all going, but I also find it nearly impossible to stick to a budget. I’ve taken to using my budget as a rough template for my spending, and simply tracking my spending against it. This approach allows for the variability of expenses from week to week and month to month, but also lets me work out where my money’s going, and find areas where I could be more frugal.

The budget’s invaluable on a day-to-day basis, but it’ll also help me make decisions if I’m asked to discount my rates or change my pricing structure.

4. I need strategies for finding new work.

I’ve been thinking that perhaps my wait-for-it-to-come-to-me approach to work won’t cut it if I’m out of work this time around. I’ve brainstormed a few ideas for finding work in markets that seem to be doing OK despite the downturn, and started networking with providers of complementary services that seem to be winning work right now.

Since I’ve done this, I’m also finding I’m more alert to potential opportunities and ideas that crop up as I go about my days, and I’ve started to keep a list of these so I don’t lose track of them.

5. I need to stay motivated.

With the constant news of unemployment statistics, redundancies and so on, it’s all too easy to get caught up in the doom and gloom. So rather than worrying, I’m trying to stay focused on the jobs I have coming up, and to feel reassured by my budgeting and any inroads I can make on my savings plan. When all else fails, I tell myself it won’t last forever — and I’m doing everything I can to stay in the game.

What are your tactics for keeping the wolf from the door?

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Expensify, a startup that aims to take the pain out of expense reporting, launches in public beta today. The free service streamlines the process of handling expenses and, thankfully, largely does away with paper receipts. It should prove useful to all kind of web workers, from freelancers to road warriors.

After the simple sign up, you’ll see that Expensify is a three-step service: import your expenses, scan your receipts, and generate expense reports.

Expensify homepage

Import expenses

The first step is importing your expenses. If you have an existing credit card for expenses that you’d like to use with Expensify, you can import expenses from it. Expensify works with 94 percent of all credit cards in the U.S. In order to import your expenses, you have to give it your online banking username and password, which you might not be comfortable with (it’s worth noting that Expensify does have full PCI compliance). If you’d prefer not to do that, or you don’t have a card to use for expenses, Expensify can set you up with a free prepaid Mastercard. This card can be loaded up from your regular credit or debit card and helps you keep business expenses separate from personal expenses.

For cash purchases, you can import expenses via SMS, email or though the web site.

Scan receipts

Expensify eReceipt

Any receipts that you have can be added to Expensify in a few ways.  First, and this is  Expensify’s killer feature, if your receipt is for under $75 you can just toss it in the trash, as Expensify can generate a guaranteed eReceipt from imported expenses. The eReceipt carries just the same legal weight with the IRS as your original receipt, so now there’s no reason to keep it. For receipts with a value over $75, you can use your cameraphone to snap a picture of the receipt and upload it to Expensify (or if you have an iPhone, there’s an app you can use instead). Receipts you get via email can just be forwarded to a custom email address.

Generate expense reports

Once your expenses have been imported and receipts added, it’s just a question of generating your report — Expensify automatically includes the receipts as required — and forwarding it to whoever needs to approve your expenses. The manager has the choice of paying the reimbursement online or through payroll.

Expensify expense report

Streamlined expenses

Although there are other players in this space, most notably American Express’s Concur, Expensify comes at the problem from a different angle. Unlike other tools that are typically designed with the CFO in mind, Expensify targets the requirements of the person filing the expense reports, which means that it’s very easy to use — once it’s set up you can generate expense reports with a single click. Expensify is free, which compares favorably to Concur’s upwards of $140 per month. Expensify CEO David Barratt says that the app is aimed at smaller companies, from sole proprietors to companies of about 100 employees (larger companies usually have other requirements such as integration with complex accounting systems). Further premium options will be added later, but the base functionality should remain free.

Expensify certainly streamlines the process of handling expense claims, and, if nothing else, not having to keep hold of lots of paper receipts is a very attractive proposition. While the design of the beta site isn’t exactly to my taste, the app does seem to do what it promises — expense reporting that doesn’t suck — very well.

What do you use for handling expense claims?

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As a web worker who cares about your career, it’s just plain good sense to do what you can to make sure that your income survives increased competition. Fortunately, WWD has offered plenty of advice on that score over the years. Here are an even dozen of our best articles and tips for supercharging your career.

Manage Your Online Presence

As a web worker, you are who you are online. While you’re unlikely to make the most obvious of mistakes (unlike those poor people who post drunken photos on MySpace and live to regret it when applying for a job), managing your online presence is a proactive endeavor. You need to think about what face you’re presenting to current and potential clients.

Build Your Brand

Your online presence is the sum of all of your activities on the internet, but your brand is both more focused and more diffuse. On the one hand, it’s a subset of your online presence that’s designed to quickly tell potential customers what you offer and why they should pay for it. On the other, good branding extends past online to other interactions with your clientele.

Pursue New Work, and New Types of Work

Now is a good time to review whether you’re trying to get all of the work that you can do. Is your career definition too narrow? Are you doing enough to get the word out?

Keep Your Costs Under Control

If your income stream is looking potentially shaky, the time to take action is now, not when you actually run out of money. In addition to pursuing new work, you can take advantage of the web and the culture surrounding web working to lower your costs of doing business.

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Of course, like just about everything else, you can also track your expenses online. The latest service in this field is expens’d, a simple and free web application. The folks behind expens’d say they were trying to avoid simplicity, and they succeeded: you get instant signup and your own subdomain for free (additional users move you into paid plans), and a way to track name, note, date, and amount for expenses. You can also tag expenses (though I don’t see any tag search yet) and create reports, which can be sent by email to anyone – perhaps the best feature here.

expens’d is entering a fairly crowded field – we looked at Xpenser last year, and more full-featured bookkeeping services like Mint and Freshbooks also offer expense modules. The most promising thing about expens’d is that it’s the first part of a planned suite of SAAS applications – so it’s worth monitoring to see if you can get useful tie-ins to other things.

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