From 2001 to 2009, I worked at a private company in various roles, from marketing manager to director. Over my eight years there, I gained stock options from my hire date in January of 2001, to my last option grant in the fall of 2008. In addition, I purchased stock as an individual in 2005 and 2006. While we filed to go public in 2007, we eventually had to withdraw this plan, and the company never did see those options become public.

Last fall, after I joined Google, the company was finally acquired, for cash. I was given some payout from my time there, and separate investing, but due to many different rounds, up and down, numerous stock splits, and the CFO position being a revolving door, getting critical details, such as how many options came from which purchases, and the dates of the acquisitions have been almost impossible to figure out.

As you can imagine, this is big problem when it comes to filing taxes. TurboTax, or any reasonable tax professional, will need to know the details of when stock sold was acquired and for how much. But the third party company that managed working with stockholders doesn't have any records of acquisition dates or prices - only the number of shares per person and value of those shares. The CFO and financial team at the company (since acquired) doesn't have access to it either. My own records, mental or otherwise, aren't a perfect match, as the stock I acquired subsequently was reverse split and diluted, so the shares I purchased don't match those I was paid out on.

So this is a fun detective game of sorts, walking through my bank records (ever try to find a check for a certain amount from 6 years ago on Wells Fargo or eTrade?), and even emailing the law firm (Wilson Sonsini) which might have this data somewhere. All in the name of trying to be as truthful as possible so I can have the benefit of paying the IRS a good chunk of money which they are owed.

Had the company been a startup acquired in its first two or three years of life, like some you often read about, you wouldn't have the complexity of multiple rounds of stock, reverse stock splits, and the changes in financial team leadership. Had it been a public company, stock purchases would be easier to find, as would the stock prices. But the meandering road of a company that fought hard for a decade, before getting purchased, makes for messy records.

I am hoping I don't have to end up filing an extension (having never done so), but the deadline to file is fast approaching, and I still have gaps. It sounds like I should have made solid marble copies of those checks I made out to the company when buying my shares and locked them away in stone. If only everything was as easily searchable in the cloud as it should be.

/via my Google+ Profile

It may only be the beginning of March, but our home's taxes are already done. It's a yearly tradition of sorts to head online, capture all relevant data, and trick Uncle Sam into giving us a refund in time to blow it all on the Final Four (not really). That's due to my leveraging TurboTax online, which gets easier every year, considering how it comes pre-linked to the prior year's data. Now, with Intuit also owning the personal finance site (and awesome iPhone app) Mint.com, the same company keeps my data organized all year round - and with tax time being a good opportunity to look backwards, I thought I would highlight some of Mint's more interesting options.

While much of Mint.com's focus has been on trying to find ways for you to save money, for example, by switching from one credit card to another, or finding a new brokerage firm, I have been watching my Mint activity to help see whether we have been breaking even this month, if our family is within budget, or through getting alerts on high expenditures and deposits. Mint has become one of my most frequently-used iPhone applications and Web sites, especially as I've managed starting the new consultancy in the middle of last year, transitioning from my full-time role with a more stable income.


As you know, doing one's taxes helps to bring clarity into the last twelve months. It gives you a sum total of what you earned, what you took home, what you were able to deduct, and how much you gave to the government. But it doesn't show you details on your spending. Mint does.

If you are a Mint user, you can walk through your spending history, and if organized well, you can see where your money is going - to your house, to your groceries, utilities, car, or entertainment, to name a few categories. After logging into Mint, click Trends, and choose Spending By Merchant.


I selected the 2009 period, and found, unsurprisingly, that 5% of our home's expenditures went to Safeway. What was a surprise is that we had more than 100 transactions at Safeway, which meant either my wife or I was going to the grocery store every 3 or 4 days (some days had multiple charges). The most we ever spent at Safeway was $208.32, and the least was a mere $5.49. In contrast, expenditures at Apple just exceeded 1% of all spending last year, less than 2 percent overall. Meanwhile, no doubt the result of having twin toddlers, and their being invited to other baby showers and friends' birthdays, there were more than 20 expenditures at Toys R Us, good enough to have gotten me a brand new MacBook Pro with all the fixings.

Just like you no doubt do when you look backward at your previous year's investments, there are purchases on my Mint.com history that make me cringe - as I look at air travel to events that proved less than useful, or wonder about whether I should have given so much money to Adobe, or raise my eyebrows at the more than $1,100 spent at Chevron in 32 separate transactions. But the more I look at the data, the smarter a consumer I become, as I use the information to change my behavior, and constantly look at Mint to see if I am on track.

Everything I have heard from my occasional talks with people at Intuit is that Mint.com's being set to replace Quicken Online is that Quicken was seen as a tool for the last generation - the one who balanced their checkbooks to the penny. Mint.com isn't yet integrated with TurboTax, but I would assume having the two properties under the same roof offers plenty of potential. The question is, can you take advantage?

No matter how many iPhone applications I have downloaded over the last year or so, I have known there has always been a big gap - that of a dedicated eTrade application, set up to let me trade stocks, transfer funds and check balances while on the go. But eTrade, until now, has stuck with an exclusive contract with BlackBerry (which we discussed in March), leaving those of us with iPhones on the outside looking in. But in the quiet shadows of Apple's iPhone 3.0 operating system release, eTrade finally rolled out their app - and even though the markets were closed tonight, my testing of the application shows it delivers exactly what I would expect, in a clear and intuitive way.


eTrade's iPhone App Highlights the Market and My Accounts
For most traders, sites like eTrade offer an important combination of both company news and trading activity. The iPhone application is no different, featuring near real-time stock prices for the markets at large, and the top news for those stocks any time you query a specific ticker symbol.


eTrade's iPhone App Lets Me Highlight Stock Charts and Trades
eTrade's iPhone application gains me access to all of my account data, from my stock portfolio to my checking account, showing balances, gains and losses, and of course, making it very easy to make stock trades - off which eTrade makes good money.

Just like on the standard eTrade site, I was able to set up alerts that would notify me if individual stocks reached a certain milestone. I could check individual stock charts for durations of days, months and years, and I could place trades from any quote.


I Can Get Detailed Quote Data and Set Up Alerts
Placing a trade on the iPhone is very easy. Testing with Apple, Google and others, I could make a bid for a stock at a limit, and could enter the number of shares of stock, assuming I had available funs to see the trade execute. I could even set up my quote data to be streaming, which I assume will push the real time upticks and downticks straight to my iPhone.

eTrade's iPhone application is one that I've personally been calling for since the first day I got my iPhone. Now that it's here, I can be ordering stock trades from my phone as easily as sending an e-mail.

As Apple's iTunes application store continues to grow, it is becoming an increasing rarity to find needs unmet by the company or its wide array of third party developers. But one clear vacancy is in the real-time stock information and trading department. I've been waiting for eTrade, my broker of choice, to develop an application for the iPhone for quite some time, but the company hasn't publicly made any strides to meet my needs. In fact, after rolling out a specialized application for the BlackBerry platform in June of 2008, we've had nine months of silence, and I'm left to believe the company is sticking with Research In Motion as their partner for the long haul.

The stereotypical image one has of today's Wall Street movers and shakers has evolved beyond the neatly pressed suits and ties, and sharp shoes, to include a hyper-obsessed BlackBerry addict, who can't look up in fear of missing an e-mail. But beyond the trading floor, consumers far from New York and other bustling metropolises are making updates to their portfolios - even in times of recession. And what eTrade has done by partnering up exclusively with BlackBerry on the mobile side is shut out the very real growing population who have selected other platforms, be they the iPhone, Google's Android, or even the Palm Pre.


eTrade Highlights Its Exclusive BlackBerry Deal
Today, using eTrade on the iPhone is barely passable. One simply has to log in through the standard Safari browser and use the non-optimized interface. It's good enough to get a near real-time update for portfolio holdings and balances, but too limiting to do much else. I'm certainly not using the Web site on the iPhone for researching stocks, reading news, making trades or seeing real-time updates.

I'm not saying the iPhone will kill the BlackBerry and render eTrade's move an abject failure, but even with BlackBerry's latest models, they don't seem to have the inside track on growth and innovation. They seem to have lost the swagger that made them a market leader for the last five or so years, while Apple and Google (to a lesser extent) have taken their place.

The iPhone is growing up to the point it's not just a game platform or a music device. I use the Mint.com application to see my up to date financial numbers, aggregated from many accounts. And Apple helpfully offers a basic stock price app. But they're no substitute for real trading.

An eTrade application for the iPhone should include:

• Real-time stock quotes
• Porfolio updates including gains and losses or trends
• Stock trading
• Company news and information
• Market overviews

For a company like eTrade, which is so broad in terms of its reach to consumers, to limit itself to a single mobile platform, especially one that seems to be on its way to being eclipsed by more nimble competitors, seems wrong. As an eTrade customer, I know I would use this application, and regardless the cost for it to be developed, eTrade would make up the amount in very little time, from the hordes of iPhone users who could start making trades on the go, from anywhere.

eTrade, your own stock is barely over a buck. I know you have other issues on your mind. But every day that goes by where I don't have an eTrade application on my iPhone means less revenue for you. Call BlackBerry up and tell them you want to see other people.

Tap... Tap... Is this thing on? (Reloads)

At the end of 2008, my #1 prediction for 2009 in the world of tech was that the real-time Web was going to grow in awareness and importance - and that a growing number of early adopters and fast followers were going to turn to sites that delivered instant updates, without waiting for filtered analysis. But there are other aspects of the Web that seemingly should be instant, and are nothing but. Brick and mortar institutions that have moved to the Web still have the delays common with their offline institutions. Pure online plays can't manage to update their data as months and years change. And the result is frustrating. As I find some services doing a fantastic job of updating instantly, it's those that lag that drive me absolutely nuts.

Back in 2006, when this blog had maybe three total readers, myself being counted twice, I encountered an issue where eTrade took seemingly ages to send from my account to a third party bank. As the two posts on the matter, from August 20, 2006 and August 24, 2006, show, a simple process of selling stock, converting it to cash and shipping it to Bank of America, that should have happened practically immediately, took about a week. While at the time I was mostly just annoyed, near the end of the year, in what looked like an instant replay, I actually bounced checks for this very reason.

As I've written about a few times on the blog, I opened up a checking account with eTrade near the end of 2007. Given the crisis at many financial institutions in 2008, it seemed a good move to have some of my cash at Wells Fargo and some at eTrade, in case one had issues. But at the end of 2007, I had to write a check that exceeded the amount of my holdings at either bank, but was less than the total amount between the two. So, planning ahead, or so I thought, I transfered money from Wells Fargo to eTrade. Days later, I wrote the check, knowing I had enough cash to cover it. But days later, I got notification my check had bounced, and eTrade did me the favor of charging me a $25 overdraft fee.

Meanwhile, I substituted the old check with a new one for the same amount, and resubmitted, as the deposit made its way through. But instead of the second one going through, and the first begin canceled, eTrade billed me a second overdraft charge, saying now that the first check had passed through, and the second had bounced. Freakin' brilliant.

So... we're dealing with that. Meanwhile, with my eTrade bank account in a thinned-state, the mortgage came due, automatically debiting from my wife's B of A account (we're working on closing that out). I wrote her a check to cover the amount, while at the same time, selling stock on eTrade's brokerage side to transfer to the checking side to give the appropriate cushion. That was done at the end of last week, but only just tonight did I get the chance to transfer the funds to the right place. Annoying. The last thing I wanted to do was bounce, yes, a third check, and then have my wife bounce her own account and have us in trouble with the mortgage company, when in fact, we did have the money, but just didn't have access to it.

I know financial institutions have these old-fashioned rules that allow a certain number of business days to make funds available, and that things aren't as easy as simply dragging and dropping money from one account to another, but given the seeming simplicity of the Web, I've got to believe there is a better way. Why should I have had to check in with eTrade first thing every morning, multiple times during the day and again at night to see if their system would let me have access to my own money? The Web should remove the restrictions not just of physical limitations, but of time as well. Just get it done.

Which gets me to my next item...

It's January 7th, right? So why, oh why, is there any reason that Compete.com's data still stops at November of 2008? Are they still waiting for those year-end reports to trickle in from December? It makes absolutely no sense. At 12:01 a.m. on January 1st, I could have given you the exact statistics for this site. Sitemeter just checks in with real-time data, and it keeps going. But Compete.com, the Web's easy way out when it comes to getting comparative traffic stats, is asleep. Call Alexa all the names you want, but at least they show December and the first part of January. Ridiculous.

But those services aren't alone...

Web digerati from Steve Gillmor to Gabe Rivera have been slamming FeedBurner's slow pickup of news and translation to RSS. RSS is practically the lifebood of today's connected, always updated, mobile content world, and the Google-owned property has put innovation on hold by hitting the snooze button.

I've seen this many times myself, as I go through Google Reader, seeing posts that took place hours and hours ago. I used to blame Google Reader for the issue... (See: Warning: Google Reader Congestion of Up to Five Hours) but now it's clear the offender is FeedBurner. If FeedBurner is destroying the capability of the real-time Web, there needs to be an alternative. There's really no good reason with so much technology at Google, and on the Web in general, that we can't find a real real-time solution.

I could keep going... but I am going to reward those services and companies that get the real-time instant Web right. There's no reason I should have to wait for my money, my data, my feeds, or any of that. I'm done with waiting.

In January, amid some scorn, I admitted one of my yearly traditions has been to zero out my stock holdings in eTrade at the end of the calendar year, primarily to simplify that April's tax returns. Not having to span investment holdings over multiple years makes tabulating my profits or loss the following year that much easier, and also gives me a chance come January to start over with stocks I believe are primed for a big year. (See: My Empty Stock Drawer)

But as has been mentioned here several times, and in every media you prefer to consume, 2008 has been very, very different, and I just couldn't stomach the idea of selling some of the stocks I own at their near-historic lows this time around. While I certainly could use the write-off, instead of clearing the deck as 2008 comes to a close, I am standing pat. Part of me says it's because I'm sure these stocks will eventually rebound, and another part admits it is pure numbness and potentially the equivalent of being in shock. Maybe instead it's post-traumatic stress syndrome.

Of course, holding on to stocks this low doesn't guarantee they won't go even lower. If you had asked me 30, 60 or 90 days ago about some stocks, I'd have remarked they couldn't possibly dip further. But nobody is an expert when it comes to what we are seeing in the financial markets today, and I don't claim to be one at all. I am even lowering my own expectations.

2008 broke a tradition of the financial markets practically making sense, and we're breaking our own tradition as well. We're either going to have a nice bounce in 2009, or we're going down with the ship.

When Mint.com first integrated the tracking of investments alongside bank records and credit cards this May, I was really excited to have a one-stop destination to see all my activity. But now, my weekly e-mails coming from the site are nothing short of a cross between a thrill ride and horror film, as one line stares me in the face: TOTAL. And peeking at the last three weeks' worth of updates shows that if I were to lose the average amount of money I lost each of the last three updates, my net worth would hit zero sometime in January of 2009. (Not on a percentage basis, but on an absolute value basis)

While I don't believe every stock I own will hit zero, and that I will have emptied all of my accounts, taking on more credit card bills than my actual assets, what was once trivial is eye-opening. While many say the smartest thing to do during this trying time is to not look at all, for me it's like a horrible accident on the highway. You can't help but slow down and take a peek. But unlike most of those accidents, there's actually more blood than expected.


My Holdings Are a Complete Disaster this Year (FriendFeed Discussion)
After a mild Spring and Summer that had my investments slightly trending downward, we all know what happened next - a massive cratering that has seen nearly everybody's financial situation turned upside down. 401ks and mutual funds that used to be stable and trusted are actually performing worse than the very worst individual stocks I've picked. One of the funds I am in dropped 24 percent last week, and another fell by more than 17 percent.

In six months, names that used to have the word "Trusted" next to their name are anything but. Fidelity. Citibank. Washington Mutual? Lehman? And yes, we know other companies in the news were less safe - General Motors, Sirius, eTrade itself... but as my own holdings are plummeting, it seems there is no safe place to turn, no "safe" investment to hold the money until things improve, be it in six months, two years, or more. Forget about Web 2.0 companies being shaky. Everybody's shaky.

For me personally, in years past, in the occasional case where I've needed to spend more money than I've had in my Wells Fargo Account, whether it be to pay year-end tithing for church, or to pay taxes, I've always known I can dip into my eTrade account and move money around as a backup. Now, that safety net has been eroded to the point I don't know that I can do that if I need to. I don't believe I'm going bankrupt, whether Mint.com thinks so or not, but unless something changes soon, we're definitely going to be putting off purchases, getting more frugal and settling for something less than we really want a whole lot more often.

And maybe I won't be logging into Mint.com all that often just to prove how bad things are.

The go-go days of the 1990s stock market, combined with the ease of online brokerages like eTrade, brought the world of Wall Street home for many people who previously saw it as a world outside their own, with high-priced brokers and a busy exchange floor. Along with the debut of CNBC, and the consumerization of financial news, including TheStreet.com and CBS Marketwatch, the potential world of day trading was brought home for millions. While the dotcom crash killed off many people's hopes at retiring rich from behind their computer monitors, most everyone has at least a passing understanding of the stock market, and many see themselves as experts - offering advice to any who will listen, even as we enter what looks like a scenario never seen before in our history, a time that will bring new challenges. Some "tried and true" solutions could work again in this trying time, and others will undoubtedly fail.

Today, after using the same methods I've used in the last seven years following the dotcom crash, I saw my personal portfolio take a hit of almost eight percent in one trading session. I've always typically invested in stocks where I feel I know the companies well, which typically sees me overweighted in the technology sector - Apple included. Of course, Apple took more than its fair share of the dive today, losing almost 20 percent of its value - which didn't help matters.

• To some, today's dive marks yet another milestone in a long, steep drop downward. The word "depression" is even being thrown around.
• To others, today's dive is a buying opportunity, giving you a chance to get stocks for cheap, down ten or twenty percent from where they were just a few short weeks ago.
• To some, buying stocks on the way down constitutes trying to "catch a falling knife", a move fraught with risk.
• To others, buying falling stocks allows them to "average down".

So now, we get advice from all sides. Buy stocks before Congress passes any version of the bailout bill, which is sure to raise stocks. Sell all your stocks and go to cash, as it's the only "safe" place. Get your cash out of the bank and into gold. You name a theory, and it's out there.

After being bitten by holding stocks long term around the beginning of the decade, I changed my methodology, holding stocks for days, or only weeks, tops. While others worried about taxes for short-term sales, I just tried to make a small portfolio larger. Often, this trading has worked, like it did when I bought AIG at $3.10 on September 16th and sold it for $4.84 on September 22nd, or when I bought Sirius Radio for 74 cents and sold it for 95 cents on those same dates. But, many other times, it hasn't, as the expected bump hasn't taken place. My bull-headedness typically sees me holding onto those losers for way too long, until those losses approach the accumulated gains from winning trades. So, despite my experience, I know I'm no expert. And the current market situation is unprecedented.

The fact that so many factors are coming into play at one time means that no single person has all the data. It's not clear who will be bailed out when, how much it will cost, how the presumed crisis will effect consumer or enterprise spending, and how it will change things in the short term or the long term. But it's not too uncommon for people to give advice without qualifications. You can see it when they say "buying on the way down will be profitable in the long run", or "get ready to buy, buy, buy" or that "smart investors (will) clean house and get ready for this amazing buying opportunity". I've seen every single one of these comments just on FriendFeed alone - which in theory wouldn't be where I'd head for investment advice.

The very tenets of what many of us have used to guide our buying and selling should always be in question. Even the concept of making a profit on every single trade is flawed, as it could make sense to sell one lot of shares at a loss to free up cash to make even more on another stock. And while I look at today's portfolio and see a bunch of red, it's not clear if tomorrow will be the beginning of a turn-around, or more of the same. With twins now, and my wife not working, at least this year, the idea would be to accumulate as much cash as I can, to prepare for tomorrow's expenses, but when I see an entire year's college tuition evaporate in a week, it's got me thinking I need to start making new approaches to guide my behavior in a time when nobody has the rule book. This could be a long learning process for all of us.

When the raging bull markets of the late 90s and early part of this decade ended, they fell with a tremendous thud. With the Web 1.0 boom turning to bust, combined with heightened fears over terrorism and world instability, the idea that one's investments would forever increase was dashed almost overnight. In 2008, we have a situation that's arguably even worse. Housing prices and demand for homes has plummeted. Energy prices are sky high. Financial institutions, having made many bad bets, are declaring bankruptcy and getting government bailouts. And unfortunately, the only near-guaranteed part of trickle-down economics is that the individuals at the bottom always feel the pain - and few are immune, myself included.

I've been lucky enough to hold down the same job from before the first recession through today. I saw Silicon Valley freeways go from being a gridlocked mess to easy driving, and back to a mess again. I saw billboards go from being plastered with dotcom ads to being "Available", only to return with a wider variety of advertising. And I've seen personal investments go from guaranteed profits to nearly pulling it all into cash, and later, getting back in, but trying not to be too exposed.

This ebb and flow is reaching a low point again. The entrance into our complex of condos is littered with "For Sale" signs, and more than one has a note of "Reduced Price", signaling the owner's desperation to move out and move on. Popular area lunchtime restaurants that used to have long lines out the door can now be visited without too much concern for parking. And, yes, my stock portfolios are bleeding out, seemingly getting worse by the day.

I thought I learned from some big losses the last time around, to not be invested in companies I didn't feel I knew very well, and not to hold stocks for a long time. I've become much more of a "flipper" who holds stocks for days or weeks, looking for what could be momentum. And at times, this has worked great. I recently played TiVo stock for a few days, and made enough profit to buy a new fridge we needed. At times, I've played Apple stock around earnings, essentially keeping me in Cupertino gadgets for free. And earlier this year, I even invested in some of the energy stocks, making money on them as the price of gas continued to climb.


eTrade Shows the Q1 Losses Are Keeping Me in the Red
But, despite these wins, right now both my personal portfolio on eTrade and my 401k are pretty hosed. On my 401k, I've lost more than half the money I've added through donations this year. And on eTrade, I've accumulated enough losses in the stocks I'm holding now that the total deficit would essentially represent lost months of work.


The 401k Says My Rate of Return is In the Cellar
Now, we're not bankrupt. And we haven't made any big purchases of late (aside from that fridge). We don't have credit card debt, and we're paying our mortgage. So we're doing quite well, compared to others who have much greater problems.

But there seems to be an air of uncertainty and discontent that comes with having less money than you had just a few months ago, and knowing what you do have isn't going quite as far. It feels like people's fuses are shorter and they're more stressed. And at times like these, it's hard to think what's going to change things. Alternative fuels? A massive change of heart in the stock markets? Probably not. This just could mean we're in the beginning of needing to buckle down, hang on and be even more judicious about what we do with our money, before things get worse.

I've been a loyal eTrade customer since February of 2000, and during the height of their instabilities last fall, I actually went against the grain, moving my checking account to the service, away from Wells Fargo, and even flipping their stock a few times for short-term sales when many thought they were headed to zero. But that's not to say the relationship is perfect. Over the years, there have been occasional annoyances, and today, errors on their part make it look like I'm about to file for Chapter 11.

This morning, Rackspace went public, the first technology company to IPO in quite some time in what's been a quiet year. And while, so far, their debut hasn't been all that amazing, I did manage to get some shares through gaining early access via my eTrade account, a usual sign that the stock would be headed down and not up, given my spotty track record.

(See also: Top Eight Worst Stock Moves I Ever Made)

But the fact Rackspace hasn't gone through the roof isn't the issue. The bigger issue is that prior to 5 a.m. this morning, I not only received confirmation from eTrade that my bid was accepted, but I received confirmation six times in the space of two minutes. And checking in with my account online, eTrade, despite only allocating to me the shares I had requested, actually looks like it withdrew the total amount of the stock buy for each confirmation. This means that instead of being cash-positive in my brokerage account, I show a deficit of more than $36,000.


eTrade Confirmed I Received Shares. And Again. And Again!
While I tend to believe this will be sorted out without any intervention on my part, I'm sure that this "glitch" will impact my ability to make trades if I wanted to. Not only is the actual cash I believe I should have unavailable, but if I sold other stocks in the account, I wouldn't have that cash available for different trades, as it would undoubtedly look like it was being used to pay down my debt.


eTrade Tells Me I Owe Them Some Serious Dough
eTrade doesn't get to participate in IPOs all that often, and it looks like they haven't quite gotten the process down. I just hope I don't start getting notice after notice that my account is "on margin" or that I get locked out. It's happened before due to stupid clerical errors like this, and I'm not interested in playing that game again. So eTrade, please get your act together and give me my money back. Thanks!

At the end of the calendar year, we have a little tradition when it comes to the stock market. Sell everything, and go completely into cash as the calendar switches from December 31 and starts again with January 1st. This year was no exception.

The reason behind my annual sell-off isn't the result of some chart-reading that tells me the market usually takes early January off (though sometimes it does). It also isn't because I have an innate need for a challenge, and see the move as starting the new year from scratch. Instead, it's simply that I do my own taxes every year, and don't want the hassle of tracking down individual trades that bridge a calendar year.

By making sure all my stock trades both begin and end in the same year, Intuit's TurboTax service can easily tabulate the gains and losses for each trade, and doesn't force me to dig through my eTrade records to see when a particular stock was purchased. Also, as I often buy and sell a single stock symbol multiple times in a year, I'm not left scratching my head and guessing where I should appropriately report I paid commissions. After all, if I have confusion, it's likely someone in the IRS will have confusion too, and might later ask me to clarify... leading to pain.

Clearing out my stock drawer (so to speak) also helps clarify what went well and what didn't over the year. There's no ambiguity as to whether one trade hasn't panned out yet or not.

So how'd we do?

Index	Q1	Q2	Q3	Q4
Me	+2%	+4%	+8%	+35%
NASDAQ	+<1%	+8%	+4%	-2%

That looks pretty good on its face. We were up more than 50% on the year. But if I dig deeper, it's clear I could have done significantly better if I completely ditched my quick trade strategy and had instead put all my money into Apple and slept on it.

Index	Q1	Q2	Q3	Q4
Me	+2%	+4%	+8%	+35%
AAPL	+8%	+31%	+26%	+29%

Being such an Apple guy, you'd think I'd have done the right thing, the smart thing, and given all I had to Cupertino. But I didn't. And while others have no doubt made out like bandits, I've ended up looking pretty silly, as the Mac and iPod maker more than doubled its market cap on the year.

I think a lot of people are looking pretty silly when it comes to AAPL. Even the most aggressive, pro-Mac guys, like me, couldn't have anticipated the kind of success Steve Jobs and team have delivered. But now, with Macworld approaching, and having cash on hand, maybe, just maybe, I'll do my part, and get back in the game. If I do, I promise I'll let you know.

Also See:

2005 Taxes in the Bag
The Stock Market Is Bleeding Us Dry
I Bet Wrong On AAPL, Again
Apple Stock Pays for AppleTV, New Airport Extreme
Taxes Completed Online, As Always
Top Eight Worst Stock Moves I Ever Made
Two Hours Of Apple Stock Plenty Profitable

It seems nary a day goes by without getting a new story from Silicon Alley Insider or another financial pub commenting on eTrade's woes. While the company's recent struggles have been well documented, many are waiting for the other shoe to drop - the declaration of bankruptcy, the report of massive losses, or a stream of customers heading for the exits. (See: E*Trade Tries to Instill Confidence, Fails)

Amid the din of bad news, I've already said I'm not leaving.

In fact, I'm doubling down, not only by staying with the firm on the brokerage side, but in a new development, I've opened up an account with eTrade's bank as well. Now, from one institution, I can have my stock activity, as well as checking and savings. And I've picked eTrade.

Why? It's actually quite simple. eTrade offers 4% or greater interest in checking, while my Wells Fargo account counters with 1/2 of 1 percent - eight times less. Also, instead of waiting days to transfer money from my bank to the brokerage, it should take minutes. And with eTrade, I don't have to pay ATM fees anywhere. Effectively, every ATM on the planet is now my bank's branch. No more hunting down Wells Fargo and avoiding Bank of America, or requesting cash back at the supermarket.

Essentially, my money is now easier to get to, easier to move and easier to see grow. While eTrade takes its time to sort out its own financial issues, I've got mine solved.