My First Million · Episode Brief
The Side Hustle King: 11 Easy Businesses Anyone Can Start
Chris Koerner runs through 11 businesses he would start today — and the most interesting ones involve porch pumpkins, sport courts, and trampolines.
Chris Koerner is an operator who has started or invested in a large number of small businesses across categories most people wouldn't think to look at. His frame for finding opportunities is consistent: look for services with recurring seasonal demand, low technological barrier, high word-of-mouth potential, and a market that hasn't yet been organized by a professional service provider.
The porch pumpkin delivery business is the episode's most memorable idea for how simple it sounds and how specific it actually is. The insight isn't 'deliver pumpkins' — it's that there is a large, underserved market of people who want seasonal decor and don't want to source it themselves. The recurring component is important: you deliver, install, and retrieve the display, which creates a subscription-like relationship out of what looks like a one-time purchase.
Sport courts (backyard basketball, pickleball, tennis) and trampolines follow the same logic: families want recreational infrastructure but don't want to manage installation, maintenance, and removal. The businesses that win in these categories aren't just selling the product; they're selling the complete service that removes all the friction from ownership.
The robot manicure and dollhouses-for-men ideas are the episode's most speculative — but they're speculative in an interesting direction. Both are bets on markets that exist (nail care, miniatures/display cases) but are either served by a dramatically different demographic or haven't been repositioned for their actual potential audience. The RV park investment thesis is the most capital-intensive idea in the group but arguably the most defensible — real assets with recurring income and a demographic tailwind.
Key Ideas
- →Koerner's template: find services with recurring seasonal demand, low tech barrier, high word-of-mouth, and a market that hasn't been organized by a professional service layer yet.
- →Porch pumpkin delivery: the real product isn't pumpkins — it's the complete service of sourcing, installing, and retrieving seasonal decor, which converts a one-time purchase into a recurring relationship.
- →Sport courts and trampolines: families want recreational infrastructure without the friction of ownership — the businesses that win are selling 'just appears and disappears when I need it.'
- →RV park investment: real assets, recurring income, and a demographic tailwind from an aging population that wants affordable extended travel — more defensible than most of the other ideas on the list.
- →The robot manicure and dollhouses-for-men ideas are bets on repositioning existing markets for different audiences — the thesis is that the category has a large latent demand it's not currently serving.
Worth Remembering
Koerner explaining the porch pumpkin business with enough detail that you could actually start it — the operational specifics, the pricing, the seasonal cadence.
Shaan's reaction to the dollhouses-for-men idea — genuine disbelief turning into genuine curiosity as Koerner walks through the actual market size.
The sport court segment: Koerner explaining how the maintenance and retrieval component transforms the unit economics relative to a pure installation business.
The moment Koerner lists all eleven businesses in sequence and the pattern becomes clear — he's not looking for the next tech startup; he's looking for the next organized version of a messy market.