From Rock Bottom to Reselling Boss: 10 Things I Wish I Knew Before I Started

There’s a moment every reseller remembers, their first spark. Mine? It happened in a dusty storage unit, surrounded by mismatched chairs, a tub of vintage Tupperware, and a broken karaoke machine. Not exactly a Pinterest dream, but something about that chaos lit a fire in me.

Hey there, I’m Kelsey, or K.K. to most. I run a solo reselling business where I dig through forgotten treasures, flip what I find, and hustle across platforms like Whatnot, eBay, Poshmark, Mercari, and Facebook Marketplace. These days, I’ve got repeat buyers asking when my next Whatnot show drops, a streamlined packing station, and a growing online following.

But before all that? There was survival. And a whole lot of chaos. (Okay, let’s be real, the chaos never really goes away.)

🔄 Let’s Rewind

I didn’t set out to become a reseller. Like most people, I had a closet full of stuff I didn’t use and a vague idea that “someone on eBay might want this.” During a particularly aggressive spring-cleaning binge, I listed a few things on Facebook Marketplace. Within hours, I had a few DMs, a couple lowball offers, and my first sale.

It was a pair of old Converse. I made $15 and thought, “That was way too easy.”

Cue the rabbit hole.

I stumbled across a local storage unit auction online (Storage Treasures, if you’re curious). I had $150 in my checking account and spent $40 on a unit full of mystery. Inside? A mix of junk and gold, unopened kitchen gadgets, old electronics, costume jewelry, and a box of vintage horror VHS tapes. I bundled the tapes and listed them on eBay. They sold for $75 in two days.

And just like that, I was hooked.

💔 The Turning Point

I started small, just dabbling. But everything changed when I hit rock bottom. I couldn’t afford a place to live or food to eat. My infant son and I bounced from one temporary spot to another. I remember clutching his tiny blanket in the backseat of our car, wondering where we’d sleep that night. My stomach growled louder than the silence around us.

I was scared. Not just for me, but for my baby. I had no idea how we’d make it through the week.

That’s when reselling stopped being a hobby and became a lifeline. It pulled me out of a desperate situation and gave me the means to care for my family. From scavenging for diapers to shipping out orders with pride, reselling didn’t just change my finances, it gave me hope, dignity, and a future.

💡 Why Reselling Works for Me

I fell in love with the thrill of the hunt. The weird, beautiful chaos of never knowing what I’d uncover. I also loved the control. I could work when I wanted, list how I wanted, and build something that was 100% mine.

No boss. No meetings. Just me, some inventory, and a label printer.

Over time, I learned what sells, what flops, and how to streamline everything from sourcing to shipping. My photos got sharper, my titles got tighter, and my packing station went from “hot mess” to “efficient operation.” But the journey was full of stumbles.

💬 Real Talk Before the Tape and Bins…

Whether you're just dipping your toes into reselling or already knee-deep in inventory piles, chances are you've already learned that this hustle is no joke. There’s the good (first sale excitement!), the bad (lowball offers), and the ugly (accidentally shipping the wrong item and realizing it too late... oops).

🧭 Before You Start

Reselling isn't about luck—it’s about learning, experimenting, and showing up. Don’t wait to feel ready. You’ll figure it out one listing at a time. Let’s break it down...

🛠 The Beginner’s Blueprint: 10 Things I Wish I Knew Before I Started Reselling

When I started, I thought I just had to post a few cute items, make them look pretty, and voilà, sales. Yeah… not quite. So, to save you from some of the chaos and help you thrive, here are the 10 things I wish someone had told me before I started this journey.

If you’re thinking about diving into reselling, here’s my no-fluff, honest blueprint to get going:

1. Start at Home - Don’t overthink your first listings, look around. Those shoes in your closet, that kitchen gadget you never use, the books you’ve already read, start with what you’ve got. It’s free inventory and the best practice you'll get. Every listing teaches you something. Plus, if you mess up, no big loss, it was just your stuff anyway.
2. Pick a Platform - Once you’ve sold a few things, it’s tempting to list everywhere. Don’t. Pick one platform and learn it well. eBay is a great all-rounder, Poshmark thrives on fashion, Whatnot is lightning-fast and live, and Mercari is beginner-friendly. Start where your items make the most sense and get to know the ins and outs before adding another. You’ll save your sanity and make more sales.
3. The Truth About Selling on Whatnot -Whatnot is not just live selling, it’s a whole performance. You’re not just a reseller, you’re a host, an entertainer, a community builder. I learned fast that to stand out, you need to show up as you. Be consistent. Be genuine. Engage with your audience like they’re sitting across from you. Also, tech issues will happen. Items won’t sell. Trolls may stop by. But the more you show up, the more you learn what works for you. Want help setting up your live space? Check out Day 4: How to Set Up a Killer Live Auction Space.
4. Research What Sells - Before you buy anything, do your homework. Just because something looks cool doesn’t mean it’ll move. Check sold comps on eBay. Scroll through Whatnot replays. Browse trending tags on Poshmark or TikTok. See what’s flying off the digital shelves and what’s collecting dust. The more you research, the fewer regrets you’ll have when it’s time to list. Trust me, knowing what your audience actually wants gives you a major edge. Don’t guess. Strategize.
5. Find Niches You Enjoy - Let’s be real, you can’t (and shouldn’t) sell everything under the sun. The resellers who succeed long-term usually specialize in something: vintage tees, toys, beauty bundles, collector cards, home décor, you name it. Find what excites you and what sells. Your niche becomes your identity, your brand, and your customer magnet. When buyers know what to expect from your shop, they’ll keep coming back for more. Plus, focusing makes sourcing, pricing, and marketing way easier. So, find your zone and own it.
6. How to Set Up a Killer Live Auction Space - Your setup matters. Lighting, angles, sound, it all plays into whether someone sticks around or scrolls past. When I finally invested in decent lighting and got a mic that didn’t sound like I was underwater, my engagement doubled. And no, you don’t need to spend a fortune. A couple of ring lights, a clean background, and a quiet space go a long way. Want to make that space really work for you? I share my must-have setup gear in Day 7: My Live Sale Starter Kit.
7. Where to Source Inventory That Actually Sells - Thrift stores are just the beginning. Think estate sales, local auctions, storage units (my personal favorite!), online liquidation sites, even yard sales in the right neighborhood. The trick is not just grabbing what’s cheap but grabbing what will flip quickly. I break down my top sourcing strategies and secret spots in Day 5: Where to Source Inventory That Actually Sells. You don’t want to miss that one.
8. Be Willing to Learn - Reselling isn’t passive income, it’s a skill. And like any skill, you get better the more you do it. You’ll make mistakes. You’ll underprice a gem or overpay for junk. It happens. I’ve been there. I remember running a live auction with $1 starting bids because it felt like that’s what everyone else was doing. One of those items, worth so much more, sold for just a dollar. I was sick over it. But you know what? That moment taught me something: just because it’s popular doesn’t mean it’s right for your business. Learn the lesson, adjust your strategy, and keep moving. Every “oops” gets you closer to “I’ve got this.”
9. Celebrate Small Wins - Your first sale? Celebrate it. Your first $100 month? Screenshot it and do a little happy dance. Reselling is a rollercoaster; some days you're on fire; others you're refreshing your apps wondering where the buyers went. If your last live show was a flop, you're not alone. It happens to all of us. Use it as a learning moment. What didn’t click? What can you tweak? Don’t be afraid to ask your viewers for feedback. The best resellers don’t just list and hope, they adjust, improve, and keep going. Ride out the slow days, because the good ones are always around the corner. And trust me, they feel even better when you’ve earned them.
10. Systems = Sanity - Inventory chaos will break your soul. Label everything. Use spreadsheets or apps like Vendoo or Airtable to track your items. Have a system for listing, shipping, returns, and live show prep. You don’t need to be a Type A robot, just stay organized enough that you’re not wasting hours digging through bins for a missing Funko Pop.
11. Burnout Is Real - You love this, but it can still burn you out. Packing orders at 2 a.m., sourcing in 100-degree heat, dealing with flaky buyers, it adds up. Schedule breaks. Batch tasks. Don’t compare your progress to someone else’s highlight reel. This is your hustle. Take care of yourself like you would your business.
12. Keep Showing Up - There will be slow days. Crickets. Cancelled orders. Lost packages. You'll want to give up. Don’t. The consistent sellers are the ones who win long-term. Even if the algorithm isn’t showing you love right now, your people will find you, if you keep showing up for them.

💬 Final Thoughts

I never thought a dusty box of random items, or falling on hard times, would lead me here. But it did. I didn’t just survive; I built a business that now supports my family. Reselling gave me freedom, creative energy, and a surprisingly supportive community.

If you’re reading this and struggling, know that you can rise too. One listing at a time.

You don’t need a fancy setup, thousands of dollars, or a warehouse. You just need curiosity, hustle, and the guts to try. And if you ever feel lost, I’ve probably been there. And I’ll probably blog about it.

👇 Drop a comment:

Thinking about reselling? Ask me anything. Already a reseller? Share where you got your start or what you’ve learned.

You’ve got this. And the more you learn, tweak, and grow, the better it gets. 💪

Want more behind-the-scenes and real talk like this? Make sure to check out tomorrow’s post: “Where to Source Inventory That Actually Sells”.