What I Learned Trying to “Sell Items to Make Money” (For Real)

What I Learned Trying to “Sell Items to Make Money” (For Real)

How It All Started (and What I Got Wrong)

I still remember the exact date: April 9, 2020 — peak lockdown.
Like millions of others, I cleaned out my closet and decided to list a few items online. A pair of Levi’s jeans, a vintage camera bag, and some sneakers I barely wore. My first sale came through Poshmark less than 24 hours later. I was hooked.

But here’s where it gets interesting…

After that early win, I hit a dry spell. No sales. No messages. No movement. I thought reselling was supposed to be easy — list, wait, get paid. Turns out, there’s way more to it if you actually want to consistently sell items to make money.

Why “Sell Items to Make Money” Isn’t About Random Listings

If you’re casually listing a few things, luck might carry you. But if you’re looking to build an online resale business side hustle, you need a strategy.

My biggest early mistake? Posting without thinking about demand.

I listed a stack of Zara blazers in August 2020, thinking fall buyers would love them. Except, I listed too early. Traffic didn’t pick up until mid-September — when I’d already lowered my prices out of panic.

That one mistake cost me about $300 in potential margin. Timing matters more than people admit.

Platforms I Tried (and Which Ones Actually Worked)

Over the past four years, I’ve listed on almost every major resale platform. Here’s my honest take.

Platform Best For My Avg. Sell Time Notes
Poshmark Fashion, shoes, accessories 3–7 days Easy to use but volume-driven. Great for flipping trendy items.
eBay Electronics, collectibles, shoes 2–5 days More competitive but better for higher-value items.
Facebook Marketplace Bulky goods, local deals 1–3 days Fast sales, but you need to deal with flakes.
Tradsey Designer apparel, handbags 5–14 days Slower sell-through but higher ASP.
Depop Vintage, Gen Z trends 7–10 days Visual-first. Great if you can photograph well.

By 2022, I realized that listing everywhere manually was eating up hours. So I started experimenting with listing management tools like Vendoo, List Perfectly, and eventually Closo. Once I centralized my workflow, my active listings grew from 40 to 180 in under two months.

And yes — my weekly sales more than tripled.

What I Learned About What Actually Sells Fast

People always ask me: “What items actually move?”
Here’s something everyone wants to know: it’s not just about what you list — it’s when and where you list it.

My top 5 fastest-selling categories from January to June 2023:

  1. Branded sneakers (Nike, Adidas, Hoka — especially in women’s sizes 6–8)

  2. Vintage Levi’s jeans and jackets

  3. Tech accessories (MagSafe chargers, iPhone cases, refurbished earbuds)

  4. Light jackets and windbreakers in early fall

  5. Unbranded home décor items with clean photos

Notice what’s not on this list: random bulk clothing or mall-brand tops. I used to list those heavily early on and watched them sit for 90+ days.

The Power (and Pain) of Pricing Strategy

Here’s the tricky part: pricing is more emotional than people realize.

I once listed a pair of limited-edition Vans for $130. Crickets.
Then, I dropped the price to $99 and got three offers in 48 hours.

Why? Because price anchors — and perceived “deals” — matter.

Tools that helped me get better at this:

  • Closo (AI pricing recommendation)

  • eBay Terapeak (historical comps)

  • Poshmark trending pricing insights

  • Google Trends (for seasonal demand)

  • Keepa (for Amazon items)

My current rule of thumb: list at 15–20% above your target so you have room to accept offers. That one habit alone added around $2,000 to my 2023 profit.

Honest Failures Along the Way

Not everything was smooth. And I think it’s important to be real about that.

  • Failure #1: Sourcing the wrong items.
    In 2021, I bought 22 “hot” fashion pieces from a liquidation pallet. Only 6 sold. The rest ended up being donated back to Goodwill.
    Lesson: don’t buy trends you don’t understand.

  • Failure #2: Underestimating logistics.
    When I hit 100+ active listings, shipping became chaos. I missed three shipping deadlines in a single month.
    Lesson: build your shipping system early.

  • Failure #3: Burnout from manual listing.
    I used to photograph, list, and cross-post one by one. I hit a wall by week 5.
    Lesson: automate earlier than you think.

Building a Real “Online Resale Business Side Hustle”

If your goal is to actually make money and not just declutter, you need to treat it like a business — even if it’s part-time.

Here’s my basic setup today:

  • Closo for listing and price automation

  • PhotoRoom for clean backgrounds

  • Google Sheets for inventory tracking (still old-school here)

  • Pirate Ship for cheaper shipping labels

  • Slack reminders for daily tasks

And — this is big — I work in batches. I photograph everything on Sundays, list on Mondays, price-adjust Wednesdays, and ship daily. That rhythm is what turned chaos into structure.

I use Closo to automate listing and repricing across Poshmark, eBay, and Tradsey. It saves me about 3 hours weekly — time I now spend sourcing.

👉 Explore Closo Seller Hub

Common Question I See: “Is It Worth Starting If I Only Have a Few Things?”

I used to think I needed hundreds of items. Not true.
I started with just 6 listings. It’s less about volume at the beginning and more about learning the rhythms of each platform.

With just a few listings, you can:

  • Learn platform culture (eBay vs Poshmark feels very different)

  • Understand what sells fast in your niche

  • Experiment with pricing without big risk

Many of my seller friends started with less than 10 items and scaled from there.

Common Question I See: “How Do You Stay Consistent?”

The short answer: systems.
The longer answer: realistic expectations.

I’ve had slow weeks where I sold nothing. And I’ve had record weekends where I cleared $1,200 in profit. What matters is setting routines — not chasing one-off wins.

Here’s my weekly structure:

  • Monday: list 10–15 items

  • Wednesday: adjust pricing + offers

  • Friday: cross-list lagging inventory to new platforms

  • Sunday: photograph & prep

Consistency beats hustle every single time.

My Favorite Tools That Actually Helped Me Scale

If I had to restart today, I’d only use these:

  • Closo – cross-listing, pricing, automation

  • eBay Terapeak – pricing intelligence

  • PhotoRoom – product photos

  • Google Trends – demand timing

  • Pirate Ship – discounted shipping

Everything else is a bonus. These five alone got me to ~$3,500/month profit.

Final Thoughts

When I started trying to sell items to make money, I thought it was about finding a few things to flip. Now I know it’s about building structure around how and where you sell.

Yes, there will be slow weeks. And yes, not everything will work. But if you stay consistent, pick the right tools, and keep learning — it can genuinely become a meaningful income stream.

For me, this side hustle now pays for my rent and health insurance. And more importantly, it gave me control over my time.

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