The side hustle from hell

Original Article ↗ Hacker News Discussion ↗

Overall reaction to the story

  • Many readers found the narrative painfully familiar: “classic dead-end startup” with obvious red flags in hindsight.
  • Several saw it less as a cautionary tale and more as a formative rite of passage—especially valuable in one’s early 20s.
  • Some said they couldn’t imagine writing about their own similar failures without bitterness, and praised the humorous, self-aware tone.

Common failing startup pattern

  • Repeated pattern identified:
    • Multiple non-technical founders.
    • Outsourced MVP built cheaply and badly.
    • Founders focused on pitch decks, competitions, and “vision” rather than customers.
    • Relentless scope creep and belief that “one more feature” will fix everything.
    • No real go-to-market plan, especially dangerous in a marketplace model.
  • Marketplace startups noted as particularly hard: must build two sides at once, often requiring deep subsidies and capital.

Learning vs warning

  • Disagreement over how much others can “skip” the pain:
    • One camp: you can’t really transfer experience; people mostly need to get burned themselves.
    • Other camp: stories like this can at least shorten the pain or stop people from working unpaid or sinking their own money.

Side hustles, careers, and burnout

  • Strong warning that unpaid or underpaid side hustles can quietly sabotage a day job and stall promotions.
  • Others countered with examples of very successful side hustles that were carefully walled off to nights/weekends and validated early with real customers.
  • Advice: if you want safety and clear growth, focus on your main career; if you want risk, accept that most startups fail and equity is likely worthless.

Technical execution & outsourcing

  • Multiple anecdotes of outsourced apps delivered with bizarre limitations and rigid interpretations of specs.
  • Consensus: outsourcing your core product is a major red flag unless you can closely manage quality and are deeply involved.

Contracts, equity, and NDAs

  • Emphasis on solid contracts, clear exit clauses, and avoiding “phantom” equity or vague promises.
  • Split views on using LLMs to analyze contracts: some see them as a helpful aid; others insist on a real lawyer.
  • Strong advice to avoid signing NDAs just to hear someone’s “next Twitter” idea and to treat unpaid “CTO/cofounder” offers with extreme skepticism.