How I Started Our First High-Ticket Drop Shipping Business and Became A Digital Nomad

I started this blog because I wanted to inspire you to break free of societies chains and live a life full of freedom and adventure too.

This is a short version of my story from when I just got started with an online business.

My life has been a roller coaster ride since I became an entrepreneur. I started an online business in 2010, got fired from my office job in 2013, and sold all our stuff in 2015 so we could become digital nomads.

In 2016, we started traveling the world and haven't looked back since.

Nobody ever said this lifestyle is easy, but it’s worth it.

It all started in the summer of 2010. After a week or two backpacking in the woods of the North Cascades National Park, I had an epiphany. I wanted to finally break free of the chains of the normal day job life and start my own business to become my own boss.

I had all the reason in the world to do it and, although it wouldn’t be easy, I had all the motivation to break free of my chains.

Upon my return, I settled back into my office sales job. I worked at a Utah-based lock supply company in Los Angeles helping locksmiths every day, providing them with solutions to their problems, and learning how a physical products distribution business works from the inside out in a complicated industry like lock and security hardware.

I started talking to some of my business clients about my ambitions to start a business and one of them really liked it.

He saw something in me others didn’t see.

He saw a leader.

I wanted to start a skateboard brand and he knew a little about internet marketing, so he offered me a website domain in exchange for a partnership.

I had nothing else going for me and the unexpected arrival of a mentor was an amazing opportunity I couldn’t pass up, so I was in.

The skateboard brand grew slowly, so we decided to try our hands with drop shipping.

We looked for skateboard suppliers and found a website that offered drop shipping services.

They look legit, but they charged $99 for access to their catalog and price guide, a huge red flag.

We proceeded with caution and when I found out the prices were too low to make a profit, we dropped them and got a refund.

They are now out of business.

We continued our look but had no success, so we changed our niche.

My business partner chose the new product and found a real wholesale supplier that offered big discounts to dealers.

He negotiated a deal to set us up as a dealer if we purchased a minimum amount of stock for our first order.

They agreed, and we had a supplier.

I then had to find a website building program so I could list their products for sale online and sell them.

I didn’t want to do Amazon or eBay at first because their fees would eat most of our profit margin.

I kept looking and found a free website building and marketplace service called eCrater, much like eBay, but they didn’t charge a fee to list or to sell.

They are still around and I highly suggest using them if you are just getting started with drop shipping as they are free to start.

Using eCrater, I created a website, listed the products, wrote my own sales copy, and started running free ads on Craigslist to drive traffic.

It took a couple months of running ads and adding product listings, but we got our first sale in February of 2011.

It felt amazing.

I actually made a clean $30 in net profit after all the fees and shipping expenses on one sale.

At that point, I knew I could make real money online doing drop shipping and that we had found a niche that worked.

Entrepreneurship isn’t a straight line, but more like a crazy path of taking a step forward and then two steps back, but then taking 5 steps forward and you start really getting somewhere.

Here’s what comes to mind

We went through a lot of ups and downs since then.

It’s been over 7 years and I’m still learning, making mistakes, breaking things, and creating income online by helping people find solutions to their problems.

Some major milestones of this business were in January of 2013 when I quit my day job. I actually was trying to get them to lay

I actually was trying to get them to lay me off instead of having to quit and it worked out perfectly.

I was able to file for unemployment and get half my pay sent to a debit card every Friday for a year.

This really helped get me past the tipping point.

In January of 2014, the online business really started to take off.

I had done a lot of work with content marketing and getting backlinks, so Google started ranking our product pages near the top of the first page of the search results.

Sales started coming in like crazy through my website and I also started selling aggressively through eBay and Amazon, almost doubling our sales numbers.

I made some huge mistakes that same year.

One of which was opening a physical retail brick-and-mortar storefront in Chatsworth, California to sell the goods I was drop shipping online and get new suppliers that required a storefront to establish an account with.

This plan didn’t work out at all.

I was expecting to get on board with these name brands easily, but they required huge upfront investments of over $10,000 each, something I didn’t have and wasn’t willing to take out a loan to get.

We did what we could to sell the products we already sold online, but the profit margin couldn’t support the retail location.

We closed the shop 6 months later in January of 2015 and luckily we found someone to take over the 18-month lease.

Moving back into my apartment to work on the business again was a huge relief.

We finished the accounting for 2014 and the gross sales amount was just over $550,000 from all the sales channels, with net profit of just under $50,000.

With an established business that had a year of high sales to show, I started researching online to see what my business was worth.

Right around that same time we got kicked off Amazon and eBay because of upset customers who had damaged merchandise.

This was a huge loss for us, but I knew I would at least be able to sell the website and get a great sum of money for it.

I decided to list it on Flippa with the intention of receiving around $50,000 at the minimum but hopefully more.

Within a week, I received an email from an interested buyer in Canada with an offer that met my minimum price.

I knew the dire situation we were facing, so I decided to accept that offer and sell the business.

That’s when everything began to change.

We were living in an overpriced 2 bedroom apartment in the valley with two cars and all the living expenses of three people (it was my wife, me, and her little sister).

We also had way too much stuff we didn’t need, some left over from the retail store we couldn’t return to the distributors.

I went to work selling everything I owned but didn’t need on Craigslist and within a few short weeks, it was mostly all gone.

I came up with a plan to get out of our apartment lease, sell my car, and downsize our life from around $6,000 a month in expenses to less than $2,000 a month.

It worked.

I sold my car using an online car buying and selling service called Shift.

We downsized everything we owned to fit into my wife’s car.

Her sister found a place to rent at a friends house where she still lives and attends college in LA.

We drove two days up to my mom’s house in Idaho.

My plan was to spend the summer there, have some fun, save some money, start a new online business, and then come back to LA in the fall.

It didn’t quite work out the way I thought it would.

We spent two weeks out there trying to help them downsize, but my mom didn’t want to sell any of her stuff, so we had to leave.

This was a blessing in disguise because she was able to keep our cats for the summer as we road tripped back down the Pacific coast that summer.

The trip ended in LA where we stayed with a friend in his spare room and prepared for our wedding that was coming up in August.

The wedding was amazing, and we spent our honeymoon in Cancun, Mexico for 10 days, followed by a month-long road trip from LA through Utah, to Yellowstone, Idaho, and Washington, where we boarded an Alaska cruise for 10 days.

It was the most incredible time of my life.

After the honeymoon, we drove to Idaho to pick up our cats and take off back down to LA to start working again.

We spent most of the money we had gotten for the business by then, so we started driving for Uber and Lyft to stay cash flow positive.

This worked out for a little while before we had to find our own place.

We found an apartment on the other side of LA in Long Beach, California, down the street from the beach and from a skatepark, it was my dream-come-true.

We spent the following 10 months there.

During that time, a lot changed.

The biggest thing was that I took on my first and only freelance client who hired me to build a website for him and do some marketing online.

He was a locksmith business owner client of mine at the lock supply company where I used to work.

It went well at first, but I couldn’t work with him beyond the website build because he wanted me to become an employee of his and work at his shop.

Around the same time, I decided to make an investment in education so that I could learn how to start a new drop shipping business again.

I signed up for the online course called Drop Ship Lifestyle and went through the training within a week.

For some reason, I just couldn’t figure it out still.

After a lot of trial and error, I learned some really important lessons by taking the Drop Ship Lifestyle course that I use to create profitable niche sites to this day.

Then, something miraculous happened.

The guy that bought my business wrote me to tell me that he was considering selling it.

I didn’t have the funds to buy it back from him, so he sold it to someone else.

After he sold it, I asked him if the non-compete agreement was void, and he said yes.

Since I knew the niche was perfect, I jumped right back in.

With my prior experience, I was able to start this new site in less than a week and start making sales the first month.

In May of 2016, we made the decision to sell all of our stuff and start traveling the world as digital nomads.

We made our first destination Chiang Mai, Thailand because of the community of established digital nomads and expats.

We lived there for almost 8 months before beginning our nomadic travels around Southeast Asia and the rest of the world.

We are going to go back there again and again because the cost of living is so low, it is very safe and people are very friendly, the wifi is great, the infrastructure is well built, and there are tons of people and things to do there.

We’ve learned a lot of lessons along the way and I’ve taken some online courses that have taught me how to hack travel rewards programs to get free hotel stays and free flights all over the world just from using credit cards for everyday business purchases.

Between October 2016 and May of 2017, we traveled to 4 countries (Thailand, Indonesia, Malaysia, and the Philippines) along with the countless cities, islands, and neighborhoods in between.

Summer of 2017 we traveled through Europe. It was an awesome trip filled with lots of skateboarding, topless beaches, incredible food, and stunning old architecture.

We ended the Summer in good ol' USA, visiting friends and family.

Today, we continue to travel the world, starting and growing online businesses and making passive income online while helping people like you do the same.

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