334: Unfair Advantages: How to Find Yours (and 10 of Mine)

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There’s a topic that no one really talks about in entrepreneurship or online business, and that’s the unfair advantages someone had starting out.

Behind every killer case study, every income report, every “overnight” success, there’s a backstory you don’t always hear.

The truth is, no one ever really starts from scratch. We bring our own history, perspectives, and baggage to the table.

We also have the advantage of learning from everyone who’s gone before us. Like Newton said, we “stand on the shoulders of giants.”

In this post and podcast episode, I’ll share some unfair advantages that undoubtedly helped me, and offer up some you probably have working in your favor as well.

how to find your unfair advantage

Common Unfair Advantages

How do you find your unfair advantage? You might not have an immediate answer to that, but one advantage you have is you’re the only “you” out there.

No one else shares your exact experience and outlook.

Here are some common advantages you might have lurking in your back pocket!


Your existing experience and knowledge are unique to you, and probably an unfair advantage you can use in building your business.

I was blessed to get experience in several helpful areas early on, including:

  • Sales – I sold paint jobs door-to-door. A humbling experience, to say the least.
  • AdWords – I didn’t have to wait for or rely on organic traffic; I could profitably buy it from day 1.
  • Blogging – I always enjoyed writing and started a personal blog in 2009, years before I ever thought of Side Hustle Nation. That gave me a familiarity with WordPress, which has come in handy, and tons of practice writing online–even though no one ever read it.

Deep subject matter expertise can be helpful in starting a side hustle, but certainly isn’t required. There are tons of examples of this in the archives, including Chris Schwab’s cleaning business, John Wilker’s pallet-flipping business, and Jessica Larrew’s Amazon reselling business.

On the other hand, if you look at Nikko Mendoza’s 3D printing business, where he’s making digital files for costume armor, it took a certain level of expertise to do that. Or Nate Dodson’s microgreens course. He could teach it because he’d done it himself.

What experience do you bring to the table? What problems or challenges have you overcome in your own life? Could you help others do the same?


“It’s not what you know, it’s who you know,” right? Your existing network, however small, can be a incredibly valuable resource to lean on when starting your business. It’s also something that’s entirely unique to you. No one else has the exact same network.

How this might work is simply telling your connections what you’re up to. You’re not likely to sell to them directly, but by sharing your work, you put yourself in a position to earn referrals. Maybe they can introduce you to someone who could use your help, or to someone who could help you.

We all have a network. It doesn’t have to be huge, it doesn’t have to be famous, it doesn’t have to be this awkward one-sided sales-pitchy relationship. But these are people who already know you, and at least care a little about you, and they’re probably willing to help you out. If it’s a fit. If you ask.


Not everyone is starting on equal ground when it comes to money.

While I didn’t have a huge nest egg (heck I was 22!), I had a little savings from working through school and no debt. I had a job, and a reasonably inexpensive lifestyle. And I had time to build something.

Others approach side hustles with more money than time. This is the Ace Chapman approach — how do I buy cash flow? Or more recently, the Stacy Caprio approach. How can I buy enough cash flow to leave my job?

Being Alive Right Now

How lucky are we to be alive right now? In our pockets, we have access to all the world’s information and connect with people in an instant, even if they’re thousands of miles away.

We have tools and apps and markets that never used to exist. Individual sellers can get shelf space on the world’s largest stores. You have the same digital publishing power that major media companies have. Getting online has never been easier or cheaper.

I get to talk to you every week from my kids bedroom closet! How incredible is that?

The gatekeepers are gone.

I see all today’s technology as a major unfair advantage for entrepreneurs now vs. even just 15 or 20 years ago.

The tools may change, but the fundamentals stay the same: a business is just a problem-solving machine. That’s it.

Who do you help? How do you help them? How do you connect with those customers? How do they pay you?

Answer those questions and you’re off the races.

1. Good Health

Aside from a few random injuries, I’ve been fortunate to be pretty healthy. I don’t have any chronic issues that prevent me from being physically or mentally able to work.

This is also something I work on almost daily, in terms of the exercise I do and the foods I eat.

2. A Good General Education

My parents raised my brother and I in a good school district. We were encouraged and expected to do well in school.

But more important than any particular topic we covered in school, our childhood education instilled the excitement of learning. It taught us we were capable of the most important skill of all: the skill of learning new skills.

There was lots of opportunity to practice reading, writing, and math–things I still use every day.

3. A Solid Financial Education

I wasn’t learning day trading in 5th grade, but I do think I had a few unfair advantages when it came to learning about money.

Earning Money

The first part of my financial education was being encouraged to earn money. That meant mowing lawns, babysitting, selling candy at summer camp, and even trying to sell baseball cards at the end of the driveway. My only customers were my friends, who were equally broke, so that didn’t work out so well. But those types of micro-entrepreneurial ventures were encouraged.

I remember getting all excited about certain baseball cards the Beckett price guide said was worth $10 or $20, and my dad saying it’s only worth that if I could find a buyer willing to pay that much. I didn’t love hearing that at the time, but a little dose of truth was probably good for me.

In high school, we were expected to work, especially summers. My best gigs were shelving books at the library and cashiering at the Mongolian Grill.


In middle school, dad set me up with a brokerage account, and I think seeded it with around $1000. In the late 90s NASDAQ boom, it soon doubled, which got me excited about the market.

Then it crashed, which made me a little more hesitant about the market. Seeing both the ups and downs was important.

In high school, one of my math teachers took it upon himself to teach us the power of compound interest and dollar cost averaging. We were probably learning about exponents and it was a real-life way to work them in. Over time, he showed us, you could amass a pretty good fortune just socking a way a few hundred dollars a month, especially if you start early.

Where he stopped short was the end-game, or the 4% rule for (early) retirement. I don’t know if that would have been motivating or discouraging to a bunch of high schoolers, but I’m certain if I’d learned about it at 17 and not 30, I would have made a few choices differently in between.

Credit Cards and Debt

Mom and dad added us to their credit cards when we were just 12 or 13. It was for emergencies only, but we learned that it wasn’t just a magical device. Whatever we bought, we paid them back.

When I turned 18, they suggested I get a credit card of my own to start building my own credit. That actually came in handy when I went to buy my first investment property.


Looking back, I think mom and dad were more well-off than they let on. Or maybe it’s just that they’re empty-nesters now, or the market’s been good to them, but growing up, they were always really intentional with how they spent their money.

They didn’t buy fancy clothes or drive fancy cars. When we traveled, we usually stayed in time share condos, which was cool because we had more space than a hotel room.

For a kid, that meant not always getting what we wanted; the cool new toy or the shoes everyone else was wearing. That was hard, but it was also important because it showed me it was OK to do without that stuff.

Instead they’d take us skiing (on rented gear of course, until we stopped growing), or we’d go hiking or swimming.

They were always savers, and passed that value along through their actions.

“It’s Only Money.”

I remember one time when we were camping, and pulling out of the campground, dad backed the car into another car that was parked behind him. He was frustrated with his mistake–this being in the days before backup sensors–and the repair was going to cost a few hundred dollars.

Still, he took the attitude that “it’s only money” and “a few days of work” would cover it. That stuck with me. Money isn’t a finite resource like time; you can always make more.

4. Living in America

Being born and raised in America is an unfair advantage all by itself. The biggest reason is that the red tape and investment required to start a business is super low relative to some other spots in the world.

And because many companies and marketplaces are based here, the side hustle landscape is easier to access.

5. No Debt

Entering adulthood debt-free was a huge unfair advantage. I paid for school with a combination of scholarships, part-time work, and help from mom and dad. There’s no question, had I come out with a mountain of debt the way many graduates do, my willingness to quit my job might have been a little different.

It would have just added to the monthly burden I’d have to cover with the business income. Super grateful for not having to worry about that.

6. A Supportive Partner (with a stable job)

Bryn and I just celebrated 20 years together, and yes if you want to do some math on that, that means we started dating when we were 15 and 16.

In addition to being the ultimate productivity hack (a super romantic joke I know I’ve made before)–just think of all the time and money we saved not trying to find someone else — that level of stability and support is a major unfair advantage a lot of people don’t have. I’m really lucky in that sense.

She’s always been thoughtful and encouraging of my various entrepreneurial ventures. I remember a particularly low point where my shoe business wasn’t working; the site was having technical challenges, the ads were getting more expensive, whatever it was, and I actually dug up my old resume file on my computer. It was a major disappointment, the prospect of having to go back and get a real job again. After I’d tasted freedom for a few years, it was a tough pill to swallow.

But Bryn said, “Don’t do that. You’ll figure this out.” And she was right. It just needed a little more time–time we could afford because we were living below our means and had a savings cushion.

7. No Kids (at the beginning)

This one could go either way–as an advantage or a disadvantage–because I feel like I’ve definitely become more focused and effective with my work time since becoming a parent.

But early on, being childless meant lower overhead in both time and expenses. Any move I made was inherently less risky then because I didn’t have any other mouths to feed.

When Tim Ferriss talks about fear setting (great exercise), life’s a lot less scary when you only have to worry about yourself!

Now kids can be a major motivating factor to build a more flexible schedule to spend more time with them, but I’m just happy I started when I did, long before they were even a thought. Obviously I love my boys and can’t imagine life without them, but they do give me a completely new level of respect for all the side hustling parents out there.

8. A Worst Case Scenario That Wasn’t That Bad

What if my original side hustle failed? What if all that effort was wasted?

Well, I would have just kept working my job and tried something new. It was low risk. Like Richard Branson said, “business opportunities are like buses. There’s always another one coming.”

Even after I quit, my worst-case scenario if everything fell apart wasn’t life-threatening.

9. A Job…

It might seem counter-intuitive that having a job was an unfair advantage, but hear me out. In my case, my steady paycheck gave me money to invest in developing my side hustle.

My limited after-work hours made me more focused and productive during that time.

The job also was on the road a lot, and on the other side of the country from most of my family and friends. That isolation probably helped in the early days of building my side hustle because it meant I had more free time.

…I Wasn’t Amazing At

One factor that made it easier to walk away from that job was the fact that I wasn’t amazing at it. I didn’t love it and wasn’t that great at it, and definitely didn’t see myself climbing the corporate ladder. So when the shoe business got to the point where it was paying my bills, that was an exciting moment–the entire day job salary was gravy.

…That Didn’t Pay Exceptionally Well

Naturally, the more you make at your day job, the harder it is to walk away. Golden handcuffs, I think it’s called.

Thankfully my only real corporate job was an entry level position that paid around $50k a year. A bigger salary would’ve been harder to leave, and I know that’s something a lot of side hustlers face.

10. Never Facing Prejudice

Unfortunately and unfairly we still live in a world with widespread racial injustice and inequality. When the average white household has 10x the net worth of the average black household, that’s a problem and it shows we still have a long way to go.

I haven’t had to face the same uphill societal battle that many others have. I’ve never been the victim of prejudice or racism. I can only imagine what that feels like, and I recognize that my starting position in life was one of privilege.

Your Turn

What unfair advantages do you have working for you today? My guess is you have several of the same ones on my list, and if not, potentially a host of others you can use.

Remember, you’re never really starting from scratch!


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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

11 thoughts on “334: Unfair Advantages: How to Find Yours (and 10 of Mine)”

  1. Thanks for sharing these, Nick. Experience is definitely a gold mine. By the way, I laughed out loud because you wrote “being a while male.” You’re right that nobody starts from scratch. Thanks for the reminder!

  2. Nick,
    Just SUPER! One of the best articles that I’ve read indeed. You’ve summary the great/keys points in your article. Many successful people prefer to keep silence about the foundation things. Or they just ignore them.

  3. Hello Nick. We met in Honolulu. I was the guy who told you that you should read The Science of Self Learning by Peter Hollins. I kept stressing how important the book was and how everyone should read it. Couldn’t help but notice the comment above “the most important skill of all:the skill of learning new skills”. Great article.

  4. Thanks for adding the “being a white male” as one of the unfair advantages. You acknowledged it, where most would have just ignored that as a factor. I really respect your effort to do that.

  5. I had to LOL, when you stated “being a white male.”
    1: Thanks for not glossing over that.
    2: Thanks for not harping on that.
    You really hit the sweet spot with the acknowledgement and the delivery.
    While I don’t have that as an unfair advantage, I’m doing what Grandma said, “Play the cards you’ve been dealt.”
    (Card Shark for a Grandma is apparently my unfair advantage.)
    Hustle on!

  6. Nick,
    So many great points and I truly think you’ve been blessed by your upbringing and certainly that comes along with the many advantages you had. I’m not sure if you’re trying to get this type of response but #10 should not be on the list. You go into great detail about each of the others and how that has affected your life and how you came out of it and then to end it with this one and write it off as “I can’t quantify” the advantages but you’re sure they’re there.
    The entire podcast is dedicated to your upbringing, your father’s advice, you’re parents help and lessons learned throughout your childhood. You also go into great detail about how hard you had to work and the obstacles you had to overcome to get there. Don’t throw up your hands and say, “well, whiteness got me here too but I don’t know how.”
    You’ve worked your backside off for the success you’ve had (as I have) as I’m sure your father and mother worked to instill all of the great traits you have that make you, you (as mine did). I’ve been a long time listener I’ve respected the fact that you’ve kept politics out of it but this one almost dropped me.
    Anyways, keep up the great work you do.


  7. Nick,

    Thanks for this episode! I think this point of unfair advantage held me back for years from starting my side hustle. When I would hear stories about people doing this or that I would use their unfair advantage as a reason for them exceeding and an excuse for me not to take on my own business goals. We all have unfair advantages we just need to slow down take a minute and write them down. Thanks for the episode.

  8. Not to start a great debate or discussion, I’m half white and easily pass (like when I worked at McDonald’s as a teen, an angry customer wanted to talk to me, not the other guy). Most of my family cannot pass. I can’t tell you about all the advantages it has afforded me or my relatives (if my mom is involved) to be assumed to have a certain background. I’m talking about being taken seriously when contacting companies or real estate agents. The benefit of the doubt is very valuable and we don’t all get it.
    I also agree that being born in the US is a huge advantage. US citizenship is so valuable and I count myself as lucky to be born state side. The infrastructure and resources this country has to offer its citizens is immense. I appreciate that you, Nick, are doing what you can to help others realize what’s out there and tap into it.

  9. Thanks for this episode! I too had a similar upbringing. I love when you mentioned your parents would not buy you the fancy sneakers because what second grader needs a hundred dollar pair of shoes, you’re going to out grow them in 6 months anyway! That is exactly what my parents said to me and what I just said to my 7 year old yesterday! My parents gave us experiences over material things and taught us to work hard. I learned the value of money early on, and I am teaching my children the same. If you want money, you have to go out an earn it. I am a Registered Nurse, and I am working on starting my own side hustle. I truly enjoy your podcast and the content is helpful for a novice in the business world like myself!


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