Poker is the new golf course

I love the sitcom The Office (both the American and British versions). In an episode last season Michael Scott proclaimed that "Chili's is the new golf course according to Small Businessman's Magazine." When questioned if the magazine indeed said that, he responded, "It will. I wrote a letter to the editor."

A few years back I thought about taking up golf, but it was about the same time that my love for poker was growing. I decided (after my wife decided for me) that I really only had the time for one of the two hobbies. I ultimately decided that I would enjoy poker more, and that I would trade the potential of teeing off with corporate bigwigs for the potential of having Daniel Negreanu chasing his flush against me at the WSOP.

In looking back over the last year, I've realized that there have been a lot of instances where poker's lent a hand in developing my business relationships:

  • Early this year I showed up at a local club for a tournament and ran into two former clients from my Bottled days who I'd lost touch with. We've talked pretty regularly since, played a lot of cards together, and done some work for each other. It's likely that none of that would've happened if we hadn't run into each other.
  • When I setup a new bank account I met with the branch manager and it slipped out that I was headed to Vegas to play in the WSOP. His face lit up as he shared his love for the game, and we proceeded to spend the next half hour talking about poker. As a result, we know each other on a first-name basis, and he pulled a few strings to help me out with my account setup (although it's probable that he would've done this for anyone else).
  • I mentioned the WSOP to one of my better clients this year and he ended up inviting me to his home game along with a few of his friends. I'm pretty certain that the experience of playing cards together helped me stand out from some of the other contractors he's used.

There are a handful of other instances that I could share, but the funny thing is that not one of my business contacts has invited me to play golf.

I don't know that poker is necessarily a better way of relating to people within the business world than golf, but according to a survey I ran across, 65% of CEOs responded that they'd rather spend their day playing poker than golf.

Either way, I can certainly attest that playing poker is a lot more fun than having lunch at Chili's.

Drawing with Microsoft Paint

When we evaluate software, we typically ask someone from sales, "can it do that?" and they enthusiastically respond, "of course!".

What we rarely ask as a follow-up is, "so how easy is it?" or "is it *really *the best tool for me to use to do that?"

We should also ask similar questions to contractors — a software developer who specializes in creating web-based applications is not who you want writing your mainframe accounting system, and vice-versa.

Nobody from the Microsoft sales department is going get an artist to throw out Adobe CS in favor of Microsoft Paint. But after showing the video below, they could probably convince some of their managers that they should.


I finally hired an accountant last week. It's something I'd been putting off, which was certainly a mistake on my part. Of course, dreaded April 15th is still over 4 months away, but it's finally sunk in that the worst time to see an accountant and start thinking about taxes is April 14th.

I've used H&R Block's online tax return service for a few years, and while it may be great if you only need to file W2s, it's not a great solution at all for me as a sole proprietor. The key for me is that an accountant who I can sit down and talk face-to-face with is going to ask me important questions like, "how many miles did you drive last year between your office and Staples to pick up supplies?" The H&R Block form just assumes that you knew you could write that off, and would enter it in line 472C if applicable.

I am by no means an expert in accounting or taxation, and everyone's situation is unique, but I can share a little bit of my accountant's feedback:

Things my accountant didn't frown at

  • I formed an LLC. The benefits of an LLC over other corporation types are mostly on the legal side, but an LLC allows you to be taxed as a sole proprietor, thus eliminating double taxation of C corporations.
  • I setup a separate bank account for the business and only used my debit card for credit transactions. Unfortunately, it took me a few months to get the account established, as I had to wait for my federal tax ID number (and I procrastinated a bit). It's very confusing to try to weed out personal expenses from business expenses when looking at a single bank statement.
  • I used Quicken (maybe I should look at Quickbooks?) to import my statements and track expenses. The cost of the software is well worth the time I would spend figuring everything out on paper or building my own reports in Excel.

Things my accountant almost smacked me for doing

  • Not paying my quarterly estimated taxes. This is something that's burned me in years past, and I know better, but I just don't do it. Since I don't have anyone withholding taxes from my income, I'm supposed to send the IRS 25% of my estimated taxes every quarter or else I get penalized on April 15th. I have to send a couple fat checks to the state and federal government in the next few weeks, but at least it won't be as fat as what I would've had to pay them in April.
  • Not keeping track of my mileage. I can go back and look at meeting dates and locations to figure out those numbers, but in my mind I'd only pictured doing that for longer trips. I'd figured that since most of my clients are located close to me it wouldn't matter enough to keep track of it, but it's looking like I was pretty wrong about that. And as I alluded to before, she pointed out that even my drive to Staples was fair game for a tax write-off. (What about driving to Starbucks?)
  • Not using her in previous years. I thought my 2005 taxes were straightforward enough for me to do on my own, but she took a look at my returns and in a few minutes pointed out ways that I could've saved $400 or so. This was enough to have covered her fees with a little bit left over.

Her best advice: "If you read something on the Internet telling you such and such is the right thing to do, just send me an email and ask about it. Don't believe any bozo with a blog." (OK, maybe I took some creative liberties with that last part).

Retirement party

I spent a few hours this afternoon at a retirement party for my grandfather, Warren Lincoln, who turns 91 in January. I really wish I had the drive and energy he has now — he jogs every morning, has been working full-time downtown in the mail room at the Indiana Department of Workforce Development for the past 10 years, and comes home each day to work around the house. He went to work early every day, and had so much unused vacation time built up (with no intension of using it) that his boss had to practically force him to take 1/2 days off every week to get rid of it.

Even more inspiring than his drive is his ability to develop a rapport with people and make them smile. It was touching to see all the people stop by and wish him well — from current and former Commissioners to the UPS guy. He's known for telling everyone a different joke every day (he calls it the "daily funny"), and almost every single person that came to the party wanted to hear one of his jokes. Being a special day, he had prepared a dozen different jokes. Here's one of his that was quite applicable for the occasion:

Unemployment isn't working

A crew from Channel 13 (WTHR) followed him around for part of the day and a segment will air on the news tonight at 6pm. Channel 8 (WISH-TV) also picked up on the story and came by to interview him for the 5pm news. Tune in if you're in the Indianapolis area. If you're not, I might be trying to figure out how to hack my DVR to get some video up on YouTube.

UPDATE: clips below.

Practice what you love

I recently watched an excellent documentary, Scratch. I highly recommend it for anyone interested in learning more about the world of DJ-ing, turntablism and hip-hop. Below is a video of Roc Raida performing at the 1996 DMC US finals. A clip from this set is featured in the documentary. (Check out the DMC videos page for more recent championship performances. I highly recommend C2C's 2005 set).

One of the interesting things I picked up from in the documentary was how much work each of the DJs put into their sets. Roc Raida and Rob Swift talk about how it took months of practice to complete the set above. Earlier in the documentary another DJ, Steve Dee, talks about how he read in a book, "if you practice for one year and give up everything — women, wine — you'll be the best at what you do." So that's what he did, and he went on to become one of the most innovative and respected DJs in history of hip-hop.

(Part of my awe towards these guys could be attributed to the fact that in college I bought a couple turntables and a mixer and set upon what was probably one of the most feeble attempts ever at learning how to become a DJ.)

A few months ago the authors of Freakonomics recently published another very interesting article in New York Times Magazine. The question it addresses is one that I've been thinking about a lot recently, "When someone is very good at a given thing, what is it that actually makes him good?"

The article presents an answer: people get good through a process of deliberate practice, explained as "setting specific goals, obtaining immediate feedback and concentrating as much on technique as on outcome." The authors argue that people who are the best at what they do become that way because of hard work, not because they're born with that ability. Related to this discussion, the article points out, "when it comes to choosing a life path, you should do what you love — because if you don't love it, you are unlikely to work hard enough to get very good."

As I think about where I am today, the answer posed in the article seems relevant to my experience. Not that I can be compared to Michael Jordan in anything that I can do, but I feel like I'm fairly proficient within my specialties. I know I wouldn't be where I am today if I wasn't blessed with the opportunity to create a career out of something I loved doing.

I had an eye-opening moment about a year or ago was when I was cleaning up some old directories on my computer. I noticed a fully-functional web application I had created a couple years prior that I had completely forgotten about. It was something that I developed as a personal project, with a slight hope that I could sell it to a client someday. As I dug through my archive, it amazed me to see the collection of software that I created on my free time — a web-based email client that I wrote one summer in college, a few solitaire card games that I created for my wife to play (because that's what geeks do for their wives instead of buying flowers), dozens of scripts to automate assorted things (one of which served as the foundation for Ponyfish), open source software that I hadn't touched in a long time (you can still find some here and here), and many half-started or half-finished projects that had been abandoned for one reason or another.

The trove highlighted the fact that I loved creating software products, something that my career was starting to take me away from. It was also eye-opening to think back and realize that the skills I possess today were mostly acquired and developed on my own. I have a degree in Computer Science, but I never had a class that taught me about the web. I've never been at a job that sent me to training to learn to do what I do now every day.

If I didn't love what I do, I wouldn't have spent countless days of free time learning and doing on my own. And if I didn't spend that time, I wouldn't be able to enjoy any of the success I have today.

What if I find my love for software development fading someday? If I don't dust off the dozen business plans I also found, or the short stories and half-finished novel I started in college, maybe I'll get those turntables out of the closet.