Back in late 2010, I had a dilemma. I was wondering whether to have a comfortable lifestyle business or the big payout. I’m pleased to say that 12 years later, I’m still happily running Financial Samurai as a comfortable lifestyle business.
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. 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 Comfortable Lifestyle Business Or The Big Payout
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. I 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.
What Did They Choose?
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.”
Start Your Own Comfortable Lifestyle Business Today
If you feel you’re not getting paid what you’re worth and want to boost your income, start your own business online on the side! It used to cost a fortune and a lot of employees to start your business.
Now you can start it for next to nothing with a hosting company like Bluehost for under $4/month. They’ll give you a free domain for a year to boot. You can learn how to set up your site with my step-by-step tutorial.
Brand yourself online, connect with like-minded people, find new consulting gigs, and potentially make a good amount of income online one day by selling your product or recommending other great products.
The easiest way to make money from home is with a blog. Not a day goes by where I’m not thankful for starting Financial Samurai in 2009.
Lifestyle Business Updates
Update 2016: I penned a new post called, Blogging For A Living: How Much Can You Really Make? This is a 3,000 word post that goes into detail on who is suitable to build an online business, and how much you can actually make after so many years. I’ve included four detailed charts from bloggers with different traffic levels and experience years. You will be surprised at how much one can make online if one sticks to things long enough. This post is a culmination of seven years working online!
Update 2023: I’m now on my 13th year blogging on Financial Samurai and couldn’t be more pleased with the decision. FS attracts over 1 million visitors a month and generates a very healthy revenue stream. I feel like I have the best of both worlds. But most of all, I still enjoying what I’m doing! I get to spend time raising my two kids under three and do what I love.
That said, the global pandemic has also worn me out. After everybody I know is inoculated, I’m going to retire again.
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