First Time Dropshipping? Here’s My Honest Experience & Lessons Learned

I still remember my first experience with dropshipping like it was yesterday, though it's been decades now. I had just lost my job, was desperate to find a way to provide for my family, and like so many others, I turned to the internet for answers. After weeks of research, two options kept popping up: dropshipping and affiliate marketing. I went back and forth for what felt like forever before finally deciding to take the leap into dropshipping. Let me tell you, it was far from easy. It was confusing, stressful, and full of mistakes that nearly cost me everything. But it also set the foundation for everything I've built since.

This post is the first in a multi-part series where I'll walk you through my entire journey, the wins, the losses, and the countless lessons learned over the years. If you’re standing at that same crossroads I once faced, wondering whether to start with dropshipping or affiliate marketing, or you’re just beginning to explore what it really takes to start a dropshipping business, this series is for you. My goal is to give you the real story, not the hype, just the truth about what works, what doesn't, and what I wish I had known from day one.

I'm not here to sell you anything or paint a perfect picture. I'm here to tell it like it happened, raw, real, and honest. If there's one thing I hope you take away from this series, it's that Dropship Business was built to help people like you build or scale a real, sustainable online business.

So, let's rewind to where it all started...

Challenge #1 | Getting My Business Off the Ground

Before I could start dropshipping, I had to tackle the most obvious problem: I needed products to sell. That meant finding a real supplier who actually offered dropshipping. At the time, I was a self-proclaimed tech geek, I loved electronics, so I figured I'd start there. This was back in the Yahoo days (Google wasn't really a thing yet), so I fired up a search and found a few wholesalers.

I picked up the phone and started calling. "Do you guys allow dropshipping?" I asked. The first company said, "No, we don't." The second one? Same thing. Finally, the third said, "Yes, we do, but you'll need a reseller permit to open an account."

My first thought was "this is not going to be as easy as I was hoping!"

"Okay," I said, "how do I get one of those?" Their answer: "We don't handle that part. You'll need to talk to a CPA."

So, I went back online and searched "how to get a reseller permit." I was flooded with offers like:
"Start your business for $999!"
"Let us get all your legal documents, only $749!"
Page after page, all saying basically the same thing.

Finally, buried about fifteen pages deep, I found a simple post that said:
"Don't pay a business formation service hundreds of dollars to do what you can do for free. Just go to the official .gov sites yourself."

That was my first big lesson in business: always go straight to the source. If the website ends in .gov, you're in the right place. If it ends in .com or .org etc, chances are you're paying a middleman to fill out the same forms you could've done yourself, for free.

It was a hard-earned piece of wisdom, but it saved me a lot of money (and frustration) down the road. Everything you need from the LLC, Reseller Permit, EIN can all be obtained from various .gov websites.

Challenge #2 | Choosing the Perfect Business Name

Seems simple enough, right? Yeah, not even close. There's nothing easy about picking a business name. If you don't already have one in mind, something you've dreamed about for years, you'll quickly find yourself stuck in an endless loop of frustration.

Ask yourself this: if I told you to name your new company right now, what would you call it? You might have a few ideas at first, maybe even a favorite, but then you go online to see if someone else is already using it. Nine times out of ten, it's taken. And that feeling? It's like hitting a wall after hours of excitement and brainstorming. You start over, think of a new name, ask your friends and family for their thoughts, check again… and it's taken too. Back to the drawing board, again and again.

After days (sometimes weeks) of this mental tug-of-war, you finally land on that one name that just clicks. The moment you hear it, you know it's the one, it fits your vision perfectly, feels right, and sounds right. You rush to make it official, filing all the paperwork and getting the necessary documents to bring your business to life.

When I started my very first business, I made the classic beginner mistake: I set it up as a sole proprietorship and ran it under my own social security number. At the time, it seemed easier and faster, but later on, I learned just how costly that decision could be. I'll cover that lesson in more detail later in this series, but for now, here's the takeaway:

If you're starting a business, even if it's just you, do yourself a favor and form an LLC. It gives you legal protection, credibility, and peace of mind. And while you're at it, get an EIN (Employer Identification Number) from the IRS. It's free, and it keeps your personal and business finances separate, something you'll be very thankful for down the road.

Challenge #3 | Inventory Management

I was now the proud owner of a legitimate business, legal documents in hand and ready to take on the world. Woo-hoo! Time to get rich, right? Not so fast. It didn't happen nearly as quickly or as smoothly as I imagined.

After getting my business paperwork in order, I contacted the supplier, filled out their application, uploaded my reseller permit, and waited. And waited. Days felt like weeks. Finally, the email I'd been hoping for arrived: "Congratulations! You are approved for a wholesale account with our company!"

"Congratulations! You are approved for a wholesale account with our company!"

I was beyond excited. I immediately called them and said, "I just got approved! How do I get your products listed on eBay?" They chuckled and replied, "We offer a spreadsheet with all our product data, you'll have to figure out how to get it to eBay from there. We don't assist with that part."

In my head, I was thinking, *"Man, you guys haven't been much help so far."* But instead, I politely said, "Okay, I'll figure it out."

After hours and hours of research that only led to complex, confusing solutions, I decided to do it the hard way, manually. The supplier's spreadsheet had around 800 products. I listed about 30 products a day, one by one. After about five days, I had roughly 150 active listings. And then it happened, my very first sale.

I'll never forget that moment. If I could have bottled up the joy and excitement I felt, I could have sold that feeling and retired right there. The product sold for $170, and my cost was $120, my first real profit from dropshipping!

Determined to fulfill the order quickly, I jumped onto my supplier's website, typed the SKU into the search bar, and… there it was, those dreaded words: "Out of Stock." My heart sank. I immediately started checking every single product I had listed to make sure the same thing hadn't happened elsewhere. It took me five days to go through them all, and that's when reality hit me: this wasn't going to be easy.

During my first month, I had around 90 successful orders, but also 20 "out of stock" cancellations and another 15 orders where I lost money due to price changes or shipping miscalculations. Some buyers were understanding when I had to cancel; others weren't, and the negative feedbacks started rolling in. Eventually, I ended all my listings until I could find a better way to manage inventory.

Next Post In Series

I hope you have enjoyed this post and maybe even picked up a thing or two. In the next post I will be going over the following topics:

• Losses Due to Pricing Miscalculations
• Better Inventory Management
• Expanding My Inventory

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