Ali’s Wacky Business Ideas | Upside #105

Strategy

29 Sept

Al's Wacky Business Ideas, Episode 3: Four Weekend Side Hustles

Episode three of Al's wacky business ideas, where Al and the host pitch four low-cost, weekend-sized side hustles to each other while Leon judges from behind the camera: a commission-based resale service for other people's clutter, a grocery automation app, geography-targeted print-on-demand t-shirts, and a seasonal house decoration business.

In this episode: Four side hustle ideas that need little to no upfront cash, each pitched, questioned and stress-tested for whether it could actually work in a weekend.

Key takeaways

Reselling other people's unwanted items on a 50/50 commission split needs zero cash upfront, but only works at real volume, since most people's "valuable" clutter isn't actually worth much.
Automating grocery shopping around the cheapest basket across multiple supermarkets is a genuinely validated idea (a version of it already exists), with meal planning and macro tracking layered on top as the differentiator.

Print-on-demand works best paired with hyper local, geography-specific designs targeting smaller towns, since the ad bidding is cheaper than targeting major cities.

Timestamps

00:00 Introducing episode three of wacky business ideas
01:12 Idea 1: resell other people's unwanted stuff for a 50/50 commission
06:53 Idea 2: an app that automates grocery shopping around the cheapest basket
12:39 Idea 3: geography targeted, print-on-demand humour t-shirts
17:13 Idea 4: a seasonal house decoration installation and takedown service
21:20 Wrap-up: which idea Zamir would actually fund

The detail

The first idea is a resale service for the stuff sitting unused in people's houses. You start by selling your own unwanted items online, then expand to reselling for neighbours or friends on a 50/50 split, eventually scaling into a drop-off centre that cleans, tags, photographs and dispatches items. The pushback: it needs real volume to be worth it, since a lot of what people think is valuable clutter isn't, and there's a related model related to this on Side Hustles, Trend Products, and Testing Fast.

The second idea is a website or app that lets you select your preferred supermarkets and a shopping list, then automatically finds and orders the cheapest total basket across them each week, with meal planning and fitness macro tracking layered on top over time. It turns out a version of this already exists as a basic price comparison tool, though it struggles when individual items are out of stock, which is where the more advanced, AI assisted version could compete.

The third idea is print-on-demand t-shirts with designs built around small town or city pride ("Tokyo, New York, Paris, Stoke"), using AI to generate designs quickly and targeting cheaper, less competitive ad bids in smaller towns rather than expensive major cities, then scaling up whichever designs and locations actually convert.

The fourth idea is a seasonal house decoration business: pitching neighbours a package to decorate their house for Halloween, Diwali or Christmas, then returning at the end of the season to take it all down, buying decorations wholesale once enough people commit, and reusing the stock in future years.