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Do What You Love: The Fantasy Sports Entrepreneur

Do What You Love: The Fantasy Sports Entrepreneur

Ever dream about finding a way to do what you love for a living? In my "Do What You Love" column, I ask people who've done it to tell me their secrets. Here's hoping they inspire you to do the same.

Taylor Caby had a knack for poker, but he also had a desire to be an entrepreneur. So, the self-taught player  decided to turn his millions in winnings into two profitable online poker companies … that is, until the Department of Justice cracked down on online gaming. Caby’s companies, CardRunners and Hold'em Manager, took a major hit and Caby decided it was time to regroup.

In September 2011, Caby launched DraftDay, a fantasy sports site that lets players pick a new team every week as opposed to being stuck with them for a whole season. The site launched with NFL games, but now offers NFL, MLB, NBA and NHL teams. Caby, 29, explains how he ended up doing what he loves for a living and offers advice on how you can, too.


Taylor Caby

BusinessNewsDaily: Explain you what you do for a living.

Taylor Caby: I guess the best way to describe me is an entrepreneur. In various ways, I have been self-employed since I graduated college in 2006. Right now, I’m building DraftDay, a fantasy sports website that lets you play fantasy sports games that last for one day at a time (instead of an entire season).

BND: How did you end up doing this for a living?

T.C.: I paid for my college by playing online poker, and towards the end of school, I started a website with a friend that helped aspiring professional poker players learn how to win at poker. In 2005, we built a website, CardRunners, and learned on the fly about running a small business. We were able to turn it into a successful company, so I was able to move on from playing poker for my primary source of income. In 2009, we purchased an educational poker software product called Hold’em Manager that has become successful as a standalone business. I spent a year or so fairly heavily involved in that business before deciding to build DraftDay. The progression has been pretty smooth, all things considered. I’ve always had an interest in online gaming and all of these companies are related in that way.

BND: What was the crucial decision you made (age, place, reason) that led you to this place in life?

T.C.: Finding online poker definitely changed my life. I always loved poker and was pretty good at it, but really learning how to win at online poker really showed me what is possible when you work hard at something. Because I had made enough money to be financially comfortable, it opened up the ability for me to pursue things I thought were interesting. Thankfully, for me, one of the things I’m most interested in is finding good business opportunities, learning about business, and making money. My financial freedom and the “aha” moment that it really was possible was what led me to where I am today.

BND: What did you want to be when you grew up?

T.C.: I didn’t really know. I always thought I would be involved in business in some way.

BND: Why do you love your job?

T.C.: I love that it’s hard and that I have no idea where it’s going to be in six months, two years, 10 years, etc.

BND: What's the biggest misconception about your job?

T.C.: That it’s not a lot of work. Most people don’t really understand all of the little details that go into running a business. Logistical stuff as simple as finding office space or setting various company policies, it’s not glamorous at all and a lot of it doesn’t have anything to do with what the primary function of your business is. For example, as an entrepreneur, a big part of your job is networking and learning about new trends. You can’t just wake up one day and say “I’m going to start a new business,” it takes hundreds if not thousands of hours of sifting through things that won’t work until you find something that’s worth doing.

BND: If you didn't do your job, whose job would you like to have and why?

T.C.: There’s no other job that realistically I could get that I’d want to have right now. If I had to say something, it would be the general manager of the Chicago Bears.

BND: Do you think having a job you love has made you a better person in other areas of your life?

T.C.: In some ways, yes, and in some ways, no. Part of the job is that there is almost always a lot to be done, sometimes I don’t have as much free time for friends and family as I would like. But I’ve also been able to help a lot of people that I care about through things I’ve been able to learn about because I have a job I love so much.

BND: What's your best advice to other people who are trying to pursue their career dreams?

T.C.: People probably aren’t going to like this, but you should be realistic. You should absolutely dream big, but you have to start small. Sitting around trying to think of the next billion-dollar idea (for example) just isn’t likely to happen. Start by thinking about where you hope to be someday and then take 10 steps backwards and think about where you can realistically be in a month or so. Set a small goal that is related to your career dream that you can spend one hour a day on for a short while. See where that gets you and then re-evaluate after you’ve had a chance to accomplish something small. Success builds on itself and its just impossible to predict out too far into the future, so don’t think that way.

Jeanette Mulvey has been writing about business for more than 20 years. Know someone who loves what they do? Tweet me @jeanettebnd with the hashtag #dowhatyoulove.

Jeanette Mulvey

Jeanette has been writing about business for more than 20 years. She has written about every kind of entrepreneur from hardware store owners to fashion designers. Previously she was a manager of internal communications for Home Depot. Her journalism career began in local newspapers. She has a degree in American Studies from Rutgers University. Follow her on Twitter @jeanettebnd.