My Simple Philosophy For Achieving Financial Freedom In 5 Years Or Less

If you ever see me at a casino, you’ll often find me playing cards at the Pai Gow poker table. Now Pai Gow is definitely NOT the sexiest game at the casino, nor is it one that draws a huge crowd.

But those who appreciate Pai Gow enjoy the game for its simplicity, its longevity and its potential for a large payout.

In fact, I’ve learned to love the game so much that I use the principles of Pai Gow to model my entire strategy for financial freedom.

The simple plan that I’m about to describe has allowed me to create multiple 6 and 7 figure side hustles and achieve financial freedom.

Both my wife and I no longer rely on a day job for income and barring any major catastrophes, we are essentially financially secure.

Editor’s Note: In case there’s any misunderstanding, my financial freedom plan does not involve gambling at a casino:)

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How To Achieve Financial Freedom – A Video Overview

The Rules Of Pai Gow And How They Apply To Financial Freedom

Pai Gow

Now before you can understand the lessons that I’ve learned from Pai Gow, you must first learn how the game works.

Below is a quick 1 paragraph description of the rules of the game.

You and the dealer are dealt 7 cards. And with these 7 cards, you create 2 poker hands, a 2 card hand and a 5 card hand. Both of your hands then go up directly against the dealer’s 2 hands.

If you win both poker hands, you win the bet.
If you lose both, you lose.
And if you win one and lose one, you tie and no money changes hands.

Here’s the thing.

More than half the time, you end up tying with the dealer and no money changes hands.

In fact, I’ve literally sat at a Pai Gow poker table for hours before and not won or lost a single dime!

Now given the slow nature of the game, how can you possibly win money if you’re pushing with the dealer more than half the time?

How the heck can you hit the jackpot playing such a boring game?

The Fortune Side Bet

The secret to Pai Gow lies with the fortune side bet.

Whenever you play a hand of Pai Gow, you are offered the chance to put some additional money in a side pot that pays out like a slot machine depending on what hands you’re dealt in the regular game.

For example if you happen to get a straight flush, you win a large sum of money.

Even hands as low as 3 of a kind still pay out a decent multiple of your bet. And as if that weren’t enough, you can still win even if a “different player” at the table gets a good hand as well.

Therefore, even though you push with the dealer more than half the time and you rarely make any money on the regular game, you always have the chance to win a huge payout.

How The Different Facets Of Pai Gow Apply To Your Finances

Pai Gow Quit

Now the regular game of Pai Gow is super slow and boring but the advantage is that you can play for a long time without losing money.

And it turns out that Pai Gow is an excellent analogy for your day job.

A regular day job is great for paying the bills and making ends meet but you will NEVER ever make life changing money by working for someone else.

Even if you were to go above and beyond and make your company a lot of money, your potential upside is capped by your steady salary.

On the other hand, the fortune side bet is where it’s at. By placing a small side bet on the table, you have the potential to make a thousand times the money you would make otherwise.

But the catch is that you have to risk a little money to play.

In real life, your fortune side bet is starting your own business. You might not win on your first try but the longer you play, the more likely you will succeed.

But if you languish on the sidelines and stick with the regular game, you’ll never get anywhere.

One of the reasons I love the game of Pai Gow is that I can go to the casino and play all night without losing all my money.

And my ability to last a long time gives me enough runway for a chance to hit the jackpot!

A More Conservative Approach To Entrepreneurship


One of the questions I most often get asked is whether you should quit your job cold turkey to pursue your business full time.

And I almost always reply hell no!

Ideally, you should keep your day job until you’ve had a chance to fully validate your business idea BEFORE taking the plunge.

After all, running a business is challenging enough as it is and you definitely don’t want financial stress to cloud your judgement.

Even though you might hate your day job and you can’t stand your boss, think of your day job as a way to stay in the game.

Use your salary to buy yourself some extra time until you can grow your business. Stick with something steady until your side project gets off of its feet.

Overall, there are no guarantees with any business. But one thing is for sure. The more time you have to validate your business idea, the more likely that you will eventually succeed.

The best and safest entrepreneurial strategies involve creating a safety net and having the freedom to take small calculated risks.

The Truth About Entrepreneurship


The biggest misconception about entrepreneurs is that they are all inveterate gamblers.

But at this point, I’ve interviewed well over 200 successful small business owners on my podcast and not a single one of them has ever struck me as a big time risk taker.

And I don’t know if the media is to blame but there seems to be this crazy myth that successful entrepreneurs like to take wild chances. But nothing could be further from the truth.

Almost everyone that I’ve interviewed so far has taken a methodical and conservative approach to starting their businesses. And to put it succinctly, here’s what they do…

They take small calculated risks. They don’t bet the farm and they iterate on their mistakes.

When my wife and I first started, we both worked our full time jobs while crafting our ecommerce store on the side.

And while we were worried about failure, running through the worse case scenarios helped to temper our fears.

  • Worse case scenario – Our business flops and we both continue to work at our day jobs.
  • Realistic case scenario – My wife works full time on the business while my day job supports the family.
  • Best case scenario – Our online store takes off big time and we sip margaritas on the beach for the rest of our lives.

How did things end up turning out?

It took a little while, but today our online store is making 7 figures. My wife and I no longer work a regular job and we spend most of our time with family.

Related: You can read my various income reports by clicking here.

In any case, I don’t want to paint the wrong picture. We are definitely not rich and we still have to work. But the nature of our work is much more flexible and rewarding.

And what’s cool about running your own business is that success begets success.

Once our online store started bringing in a steady income, I set aside some of the cash to start on the side.

Within 3 years, started to take off so I invested some money to start my ecommerce training course.

Once the ecommerce course started making money, I took some money off the table to start my podcast.

From there, my podcast led to an ecommerce conference. And today, I’m in the process of starting 2 new businesses as well!

My latest project is called Go Brand Win which is a service that helps small businesses build their email lists for FREE.

In fact if you have an ecommerce brand, I encourage you to join.

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My other new project is called The 5 Minute Pitch which is a Shark Tank like show where we’re giving away $50,000 to one lucky company.

Now I don’t project that either of these companies will make much money at all for the next few years and that’s ok.

My other businesses will finance these projects until they get off their feet.

Key Takeaways

If you take away anything from this post, it’s that you will never make life changing money unless you play the fortune side bet.

And in real life, your fortune side bet is your business.

But starting a side hustle doesn’t have to be risky.

If you decide to take the plunge, then make sure you have a backup plan.

Stay at your day job until your side hustle can you support you. Then, build upon your existing successes until you have a portfolio of income streams.

Further Reading: How Long Does It Take To Start An Online Business?

Editor’s Note: If you are interested in playing the fortune side bet and learning how to start your own ecommerce store, then consider taking my FREE 6 day ecommerce mini course.

I’ve been told that this free course is better than most paid courses out here.

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About Steve Chou

Steve Chou is a highly recognized influencer in the ecommerce space and has taught thousands of students how to effectively sell physical products online over at

His blog,, has been featured in Forbes, Inc, The New York Times,  Entrepreneur and MSNBC.  

He's also a contributing author for BigCommerce, Klaviyo, ManyChat, Printful, Privy, CXL, Ecommerce Fuel, GlockApps, Privy, Social Media Examiner, Web Designer Depot, Sumo and other leading business publications.

In addition, he runs a popular ecommerce podcast, My Wife Quit Her Job, which is a top 25 marketing show on all of Apple Podcasts

To stay up to date with all of the latest ecommerce trends, Steve runs a 7 figure ecommerce store,, with his wife and puts on an annual ecommerce conference called The Sellers Summit.  

Steve carries both a bachelors and a masters degree in electrical engineering from Stanford University. Despite majoring in electrical engineering, he spent a good portion of his graduate education studying entrepreneurship and the mechanics of running small businesses. 

16 thoughts on “My Simple Philosophy For Achieving Financial Freedom In 5 Years Or Less”

  1. Kayvee says:

    Dear Steve

    I just want to acklowdge you for giving the world so much value in knowledge and in tools.

    You are an inspiration to all of us.

    Please, Keep doing what you are doing.


    1. Steve C says:

      Thank you so much Kayvee!

  2. Ree Klein says:

    I love your analogy and advice, Steve. This line in particular struck me:

    “The best and safest entrepreneurial strategies involve creating a safety net and having the freedom to take small calculated risks.”

    Having a surplus of money and no debt creates choice. Having the ability to make choices (like to quit or keep a job) = FREEDOM.

    Because I had already paid off my debt (including my mortgage) and saved a nice emergency fund, I was able to move in with my mother and take care of her in her last year of life. She passed last week and I’m so grateful that we were able to have the time together that we did. It wouldn’t have been possible had I been a wild risk-taker or lived on credit.

    Wise advice, my friend.


    1. Steve C says:

      Hey Ree,
      I was on vacation so I didn’t see your comment until now. I’m so sorry for your loss and wanted to express my sincere condolences. I’m glad that everything is set for you financially

    2. Jennifer says:

      I am so sorry for your loss Ree. What a blessing it must have been for her to spend so much time with her daughter her last year of life.

      1. Ree Klein says:

        @Steve and @Jennifer ~ Thank you for your thoughts about my loss. I can’t imagine how tortured with regret I would have been had I not had the financial resources to be with her over the last year. If for no other reason, gaining financial flexibility on any level is so important because it gives you options.

  3. Gen Y Finance Guy says:

    Very sage advice.

    I totally subscribe to mastering the work/side business blend until you can eventually make a clean break.

    Take advantage of the cash flow from your JOB to test, tweak, and validate your idea.


    1. Steve C says:

      Thanks Gen Y!

  4. Jennifer says:

    Great post as always Steve! I have been saving this in my inbox for a while, wanting to read it and it was just what I needed this week!

  5. happy wheels 247 says:

    And as if that weren’t enough, you can still win even if a “different player” at the table gets a good hand as well.

  6. Moji says:

    Every single one of your posts is so valu packed. Thanks for all that you share Steve. Bless you!

  7. GreenDollarBills says:

    Hey Steve, I love poker but I’d never heard of Pai Gow – what a fantastic analogy to life. Simple concept but really hits home. It either takes serious balls or stupidity to quit your job without having even started. The side hustle is the way forward….now where do I find a Pai Gow table again??? lol

  8. Neetu Kumar says:

    I am very enjoyed for this blog. Its an informative topic

  9. Jack Jon says:

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  10. poonam says:

    Thank you for sharing this article

  11. Blissmarcom says:

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