Hillside Trends · 2022 to 2025
When the operation has to fit around school
Running five storefronts alone, from sixteen
Hillside Trends was my vintage resale business. I was the whole staff, so I built the small systems that let one person do the work of several.
- Role
- Founder
- Team
- Me
- Timeline
- August 2022 to June 2025
- What changed
- A weekend thrifting habit became five storefronts and 600+ orders shipped
In short
- Resale is where hobbyists go to burn out.
- Mine fit in a few hours a day around school.
The rack and the packing table
Sell a tee: I pull it from the other four storefronts and ship it.
Seven pieces, five storefronts.
The 600+ orders are counted from the storefronts’ order histories; the tees are stand-ins. Photographs by Tolukra (CC BY-SA 3.0), Relicário Multimarcas – Aurora (CC BY 2.0) and Jönköpings läns museum (CC BY 4.0); the hanger by RL0919, the printer by Jiří Sedláček and the mailer by Student joli (CC BY-SA 4.0, as are the cut-outs made from them).
My part
- Builtinventory tracking across all five storefronts, margin and fee tracking, and reply templates.
- Raneverything else: daily listings, sourcing, pricing, photography and shipping, through high school and my first year at Cornell.
Sneakers too
Same system, different box.
Stand-ins again: the box is from the Auckland War Memorial Museum (CC BY 4.0).
The problem
The moment reselling starts to work, the work multiplies. Could a sixteen-year-old with a laptop in Wellsville, New York, run it like a real operation and still get through high school?
Decision log
to build systems before adding a fourth or fifth storefront.
Rejectedgrowing first and cleaning up later.
Whyone sale on eBay meant delisting the piece by hand on the other four.
Resultall five ran in a few hours a day.
to answer customers from templates.
Rejectedwriting every message from scratch.
Whythe same 20 questions arrived every week, usually while I was in class.
Resultcustomer service stopped eating my evenings.
to let the sales data pick the next buy.
Rejectedbuying what I happened to like.
Whythe forecasts showed limited-run luxury tees selling faster, at a higher margin, than anything else in stock.
Resultthe business refocused on them, and the margin followed.
to wind it down and work on Ventura full time.
Rejectedkeeping both going badly.
Whythe systems still worked, but my attention didn’t scale.
Resultit closed cleanly in June 2025.
What it taught me
Every call was mine, with real money on the line, while the lessons were still cheap. I learned to build the tool I needed instead of wishing I could hire someone, and never lost the habit.
