Over poker one night, we got to talking about what we always talk about: entrepreneurship. Out of a table of 10, four work at start-ups, three are at Google, one is a high-tech lawyer, one works as a medical correspondent for CNN, and then there’s me, a hybrid. I had just got done working on Yakezie.com for three hours after working an 11 hour day, and needless to say, I was a little bit tired.
I love going to Friday night poker mainly because I get to bounce ideas off of really smart and incredibly hard working people. When I hear stories of one start-up player working from 7am to 3am every night for two weeks straight to launch a product offering, I get pumped. When the Venture Capitalist player recounts his firm rejecting a pitch by Tim Westergren, Pandora’s founder in 2008, I wince, but daydream in amazement.
THE LIFE AND BUSINESS QUESTION
Down about $185 for the evening, I started lamenting what the money will cost in side hustling. A couple hours of work at least, I thought. How depressing, thanks to my opponent’s King on the river against my pocket Queens! I quickly shifted to more pleasant thoughts about the future of start-ups and posed this question in between hands to my fellow sharks:
Would you rather make $15-000-$30,000 a month and “work” only 2-4 hours a day? Or, would you rather make minimum wage working 12-18 hours a day for two years with a 25% chance of selling your business for $100 million dollars and netting yourself a cool $25 million? If you don’t, all you are left with are your experiences.
I purposefully left the question open-ended to see what the various responses would be. Already, one was doing math equations of what the capitalized value of $15,000-$30,000 a month would be based on an expected life expectancy compared to the expected value of the big payout. After all, we calculate expected value all the time in poker. Instead, I encouraged my fellow players to stop calculating and go with their gut.
Surprisingly, or perhaps not to be unexpected, every single one of them chose option 2: the big potential payout. A couple of the entrepreneurs have a $100 million dollar buyout goal in mind, which I find somewhat delusional, but maybe not with Zynga, Youtube, and a host of other companies getting valued in the billions!
As the night wore on, I finally heard someone take the other side after losing $690 in a $2,600 4-way pot when his straight got flushed out.
“Well, $30,000 a month for working only a couple hours a day isn’t so bad. I think I’ll go with that.”
STARTING AN ONLINE BUSINESS
It’s been over six years since I started Financial Samurai and I’m actually earning a good passive and active income stream online now. The top 1% of all posts on Financial Samurai generates 31% of all traffic. In other words, after putting in the hours to write some very meaty content over the years, 10 posts consistently generate a monthly recurring income stream that’s completely passive.
I never thought I’d be able to quit my job in 2012 just three years after starting Financial Samurai. But by starting one financial crisis day in 2009, Financial Samurai actually makes more than my entire passive income total that took 15 years to build. If you enjoy writing, creating, connecting with people online, and enjoying more freedom, see how you can set up a WordPress blog in 15 minutes with Bluehost.
You never know where the journey might take you! I spent four weeks traveling to Cambodia, Taiwan, Korea, Vietnam, and Malaysia while working on my business in 2015 and plan to work overseas again in 2016. The freedom and reward for creating something on your own truly is priceless.
Updated for 2016 and beyond.