299: Trading Up: From $8.65 an hour to “Retired” at 25, Plus the Next 10 Years

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Remember the Red Paperclip Guy from a few years ago? In 2005, an out-of-work Kyle MacDonald started with a single red paperclip and traded his way up to a house in Kipling, Saskatchewan.

Remarkably, this barter adventure took only 14 trades and was completed in less than a year. Kyle started out small, each time seeking something “bigger and better” in exchange.

For example, his first trade was the red paperclip for a pen shaped like a fish. Then he traded the fish pen for a doorknob, and on and on up the ladder.

The story certainly has some feel-good elements to it, and after a while the media attention definitely helped speed the process along, but I think it’s worthwhile to revisit because we’re all trying to “trade up.”

By “trading up”, it’s important to note I’m not necessarily talking about acquiring a bigger house or a better car, but more along the lines of making bigger impacts and living better stories.

I was reminded of the red paperclip story by last week’s episode with Rob “The Flea Market Flipper” Stephenson. He talked about a challenge inside his community to start with something small and keep flipping the profits into bigger deals to see how much you could trade up over the course of a year.

I think we all have a red paperclip story. Like Kyle, even starting with almost nothing, you can make big things happen with a little initiative and a little help from others along the way.

red paperclip house
Kyle, in front of his house.

(image source)

Perhaps you “traded” 4 years of school for a good job upon graduation. Perhaps you traded the money saved up from that job for a year traveling the world.

This episode is about connecting the events that got you to where you are today, and thinking about where you want to go tomorrow.

What’s the next trade you’d like to make?

In the spirit of the red paperclip story, I’m going to use my own entrepreneurial journey to illustrate this; and similar to Kyle, I’ll use a series of 14 key decisions or trade points. But unlike Kyle, this took me a lot longer than a year!

Starting Position: Trading Hours for Dollars at the Library

My Red Paperclip story begins with my first real job: shelving books at the library for $8.65 an hour.

Working part time at the library, I managed to save up some money. In my first year of college, I had the opportunity to apply for a “management internship” with College Works Painting. Basically they put you in charge of a territory and you have the spring and summer to build up a residential painting company from scratch.

This ended up being one of several ways I made money in college.

Trade #1: Buying a Truck

Even though I had no idea how to paint a house, I accepted the job and made my first “trade”; exchanging my book-shelving money for a cheap used pickup truck. It was about $3500.


It was a scary risk to take at the time, blowing half my net worth on a car, to try my hand at a business that, in all reality, had a pretty high likelihood of failure. But it was an important trade because it marked my first steps down the path of entrepreneurship.

The painting business was at once the most stressful and most rewarding work I’d done up to that point. For adults to entrust their biggest investment over to inexperienced college kids with paint sprayers hit me with a heavy burden of responsibility not to screw it up.

And there were definitely screw-ups.

College Works was my first introduction to the rush of entrepreneurship, making cold calls, closing sales, and delivering results. It was also an eye-opening and challenging experience like no other.

I came into the internship with a cocky attitude (typical of college freshmen?) that I was going to be #1. I left extremely humbled, having learned I was far from being the best salesperson, the best manager, or even the best painter.

This was a great side hustle for teens.

The Light Bulb Moment

In that way, the truck led to probably the most important realization of my life: you’re not that great.

You’re not that smart.

You’ve still got a lot to figure out.

I always say I wish I was half as smart now as I was when I was 16, and painting played a big role in putting my ego in check, and turning me into a life-long learner; striving to improve every day.

But in the end, thankfully the happy customers outnumbered the unhappy ones, and over the course of two summers I sold enough paint jobs to cover the cost of my truck several times over.

It was my first taste of working for profits, not wages, and may have scarred me for life. And not just because I fell off a ladder!

Trade #2: Joining a Business Fraternity

For much of freshman year, college at the University of Washington was like an extension of high school. In fact, it seemed like half our graduating class ended up enrolling there.

In part to force my introverted self to meet new people, and in part because I was still concerned with building a resume, I pledged the co-ed business fraternity Alpha Kappa Psi in the fall of my second year.

For me, AKPsi was an amazing community of like-minded individuals. It gave everyone the opportunity to practice real-life leadership skills in a safe environment, as well as to develop lasting friendships.

Softball team

I count joining the fraternity as a pivotal moment because it was me stepping out of my comfort zone and making meaningful connections that were valuable then, valuable later, and I’m sure will continue to be valuable into the future as well.

Now if college is a distant memory for you, how can you apply this one?

It’s really about shrinking an overwhelming environment into one that’s more manageable and relevant. It’s about finding your people.

I know I talk about the importance of mastermind groups a lot, and even though we didn’t call it that, it was a similar concept. You could do the same in your local community with meetups or events, or starting your own, or finding your people online. 

Shameless plug: The Side Hustle Nation Facebook group is over 10,000 strong now.

Trade #3: Buying an Investment House

Back at school, my roommate insisted I read Rich Dad Poor Dad, which got me interested in real estate investing. With the majority of the painting profits sitting around in a low-interest savings account, I began seeking out investment opportunities.

This was an important step too, because it represented the first shift from the Employee/Self-Employed side of the Rich Dad Cash Flow Quadrant, to the Business/Investor side.

With the help of some real estate professionals, I eventually located and bought my first investment property at age 21. In those glorious early-bubble years, you could buy a house with just 5% down and no income verification!

Looking back, this was an incredibly risky move that probably only could have been accomplished with a 21-year-old’s foolish sense of invincibility. Luckily for me, it worked out better than OK and I was able to sell the house for a very healthy gain before the market crashed.

I say “luckily,” because there was honestly not a lot of business savvy on either end of this deal.

You know the saying, “Sometimes it’s better to be lucky than good?” This was one of those times.

Trade #4: An Ecommerce Internship

After retiring from painting, my roommate pointed out an ad in the college newspaper’s classifieds for a marketing internship.

(You may be noticing I owe a lot to my roommate; he was even the officiant at our wedding!)

At the time, I really wasn’t looking for a job but this one sounded interesting so I submitted an application and was invited in to interview. Since I wasn’t necessarily in the market, I figured I had nothing to lose.

The company was an online footwear retailer and hired me to be their part-time marketing intern.

This was really another important step for me because it was my first introduction to ecommerce, search engine optimization, pay-per-click management, and affiliate marketing. All of those things would of course become crucial skills down the road.

This is as close as I ever came to Taylor Pearson’s apprenticeship model we talked about in episode 129. He argued you should quit your side hustle, and instead accelerate your entrepreneurial education by taking an apprenticeship directly with someone in your desired field.

Trade #5: Turning Down a Job Offer

At the end of my internship the company offered to keep me on board, with the implication I might have a place there after graduation. However, with perhaps an inflated sense of self-worth, I wasn’t happy with their offer and declined.

Sometimes I think back about how life might have been different if I’d stayed with them, stayed in Seattle, and gone down that path. This is one of those forks in the road that, looking back, definitely had a profound impact in my direction.

Applying what I had learned at work, I began dabbling in affiliate marketing in my spare time while back at school. I formed my first company (probably unnecessary for the dollar volume I was doing, but it felt cool) and remember seeding the business bank account with $500.

At that level of investment, it was just a fun experiment; a hobby on the side to try and earn some beer money. If it didn’t work out it wasn’t going to be the end of the world. And that was my first real side hustle.

Trade #6: Traveling to Costa Rica

By accumulating some course credit from AP classes and taking a heavy course-load most quarters, I was able to graduate from college one quarter early. While everyone else was still attending classes, I was a free man.

Thanks to a graduation present from mom and dad, I had the opportunity to travel to Costa Rica to participate in a Habitat for Humanity building project and to explore the country. This was my first time traveling by myself and it was a great experience.

I learned even though you’re traveling by yourself, you’re never really alone. You meet fun and interesting people everywhere you go. You figure things out and survive. My time in Costa Rica was pretty brief, but I loved the pura vida lifestyle and getting by on my gringo español.

costa rica

I’d traveled a decent amount before, but this is the trip that hit me with the travel bug for good. On top of that, my fledgling affiliate business was still chugging along even when I was away from the Internet for days at a time.

I remember stopping by an Internet cafe every few days to login and check email and check commissions from the business. 

It was my first taste of that elusive passive income!

Related: Want to travel for free? Check out me free course on Credit Card Rewards.

Trade #7: Moving Across the Country

Through AKPsi, I was introduced to the Seattle regional manager for Ford. He invited me and several of my “brothers” out to Detroit to interview for jobs.

For us West Coast kids, Ford was about as relevant as the Mariners in October (which is to say, sadly, not at all). Still, we figured if nothing else we’d at least get a free trip out of the deal.

As you might have guessed, I was offered the job and accepted. The interesting thing about Ford at that time was you didn’t know where you’d be working until right before you started. You just knew you were going to move, and that it would probably be far away.

The theory was, if they put you far away from your friends and family, you’ll be more focused on your work and your Ford co-workers will become your friends and family. Sure enough, I was assigned to the Washington DC region all the way on the other side of the country.


Part of me liked the adventure of it, and thought it would be worthwhile to leave Seattle and see what else was out there. I’d lived there almost my entire life and had been with my girlfriend since high school. This was an important step for getting out of my comfort zone again and seeing if we had real staying power once there were 3000 miles between us.

I’m happy to report everything went OK and we’re coming up on 20 years together.

Trade #8: Having my First Website Built

In DC, three factors collided to form a perfect entrepreneurial storm.

  1. I didn’t know anyone aside from my co-workers, so I had a lot of free evenings — especially on the weeknights.
  2. I was looking for ways to scale my miniature affiliate marketing business. It was still a fun and profitable side hustle, but it would take some major re-thinking to turn it into something bigger.
  3. My investment property sold, leaving me with a windfall of cash. Considering it had all started with a cheap pickup truck a few short years ago, I was ecstatic.

shoesrus logo 200x200

I decided to use a portion of the proceeds to build a website and try and make a real run at affiliate marketing as a viable side hustle business. I posted my vision for the project on the freelance site Guru.com, and found a qualified developer who actually lived just a half an hour away from me in Northern Virginia.

The original site was called ShoesRUs.net, and cost around $10,000 to develop. The project took twice as long to finish as it was supposed to, had an ugly design, and was missing several critical features.

Still, it was the best investment I ever made.

This was the vehicle that led to Trade #9…

Trade #9: Quitting my Job

I worked my butt off to make Shoes ‘R Us a profitable side hustle.

It was not an overnight success. It was three years of nights and weekends.

But finally I got to the point where basically having 2 full-time jobs didn’t make sense, and I got up the nerve to “retire” from Ford and focus on the business 100%. My side hustle turned into my main hustle, and I was excited and nervous to be a real life entrepreneur.

The decision to focus my energy and attention was an important one; revenue more than doubled the year following my “retirement.”

Trade #10: Hiring my First Virtual Assistant

As the “shoe biz” was growing, I found my days overwhelmed with the routine work of maintaining the site.

It was rewarding because I could see an immediate impact of my efforts on the bottom line, but I was very much a victim of the entrepreneur’s trap described in the E-Myth Revisited — I was working in my business rather than on it.

I knew I needed help but didn’t know where to look. I didn’t want to deal with the hassles of hiring a local employee, so I began researching virtual assistants.

Eventually I found a VA with a company in Pakistan who was great. It was a really interesting experience working with someone from such a different culture, and helped me learn new skills in training, process documentation, managing a remote employee, and most importantly, letting go.

My business had always been a one-man show so there was definitely a mental hurdle to overcome in opening the doors to an assistant and exposing my strategies and “secrets”. But for me and for every other entrepreneur, hiring your first employee (whether virtual or not) is a big leap for the mindset of growing the business and being smarter with your time.

Trade #11: Starting a Blog

I started blogging in 2009, mostly because it seemed like a fun creative outlet. The blog never gained the traffic or attention of a wide audience, and didn’t really earn any money, but it was a useful venture nonetheless.

I learned how to use WordPress, which is software I use now almost everyday. WordPress powers this site and millions of others so it is an essential tool to understand for anyone working online.

And equally important, blogging got me in the habit of writing on a semi-routine basis, which I think is a healthy exercise for my mind — even if very few people ever actually read it.

Related: Check out BlogStarterCourse.com for my free guide on getting your blog up and running.

Trade #12: Building Other “Affiliate Sites”

I’d made several attempts at branching out from the world of shoes, but most of those flopped.

However, the most successful of the projects from this era is still around. It’s a directory and review platform for outsourcing companies called Virtual Assistant Assistant.

This new project allowed me to experiment with a ton of new marketing tactics, including starting my first email list, reaching out to visitors on Twitter, guest blogging, recording my first YouTube videos, adding a custom “recommendation engine” survey tool, and even writing my first book.

This was also an important step for me in putting the “expert enough” theory into practice. That is, if you know more about a topic than the average visitor, you’re an expert in their eyes. What could you be an expert in?

Trade #13: Starting a Podcast

In 2013, the shoe business was still my main focus, but as I’d been doing for several years, I always had side projects.

And by far the best side project I started was The Side Hustle Show podcast. I had no idea what I was doing, the first episodes are super embarrassing, but despite that, I started to see some traction.

And it was fun, so I stuck with it, and it’s been a truly life-changing trade.

For the ideas, for the connections with guests and with listeners, and for building a community, I think a podcast is tough to beat. 

Obviously I’ve learned a lot about podcasting over the years and try to make a better show every week, but it was that act of starting – not really knowing what it would entail or what I was committing myself to — that was the most important thing. 

Trade #14: Having Kids

Becoming parents was probably our biggest lifestyle and business shift. 

We’ve decided that parenthood amplifies life; the lows are lower, but the highs are higher, and it hopefully all averages out.

As I talked about in the episode with Noah Kagan, I feel like our kids are good at helping us figure out what’s really important. I’ve become less productive, but more efficient, if that makes sense.

It forced me to be more efficient and more intentional with where I spend my time, knowing that time is more limited.

Case in point: Business has more than doubled since our first son was born. It wasn’t about working more; it was about working smarter.

Final Thoughts

It’s fun to see how all these little decisions and connections give shape to your life and to your work.

There are a couple overarching “themes” I think are worth calling attention to.

The Hustler’s Mindset

The first theme is about attitude.

Side hustlers take the stance that the world is full of opportunities, and it’s just on them to pick one and execute. It’s a mindset of abundance and optimism.

Naysayers will complain that all the good ideas are already taken or come up with a hundred reasons not to pursue an opportunity. Ignore them.

Taking Calculated Risks

The second theme is about taking risks. If you want to make something happen you’re going to have to take some risks. Now I consider myself a pretty risk-averse person; I don’t gamble, I don’t play in the stock market; and I don’t do any crazy high-flying skiing stunts.

(To be fair, I have been skydiving a couple times though:)


The ability to take calculated risks has been absolutely critical. I like to think of certain business or investment risks as experiments, maybe because it makes me feel more science-y.

The word “risk” sounds dangerous; an “experiment” on the other hand gives you the opportunity (there’s that word again) to learn something new — no matter what the outcome.

In each case above, I had to ask myself, “What’s the worst thing that could happen?” And in every case, the downsides were never life-threatening. We tend to overstate the impact of failure, when the truth is we’d just dust off and move on.

I’ve made dozens of bad bets, but I never made a bet I couldn’t afford to lose.

Even if you don’t a have a side hustle right now, your journey into entrepreneurship is already years in the making. Think of the decisions and events that brought you to this day. How can you leverage those into something valuable?

Life is the accumulation of experiences. I’m confident you can make something happen with what you’ve already got.

Your Turn

I’m curious, what big events or decisions in your life would you credit toward getting you to where you are now?


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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.

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