Best of EntrepreneurshipSeptember 2025

  1. 1
    Article
    Avatar of jasonfriedJason Fried·34w

    What to do with $2M?

    A successful entrepreneur advises a young founder who recently sold his business for $2M to prioritize capital preservation over aggressive investment or reinvestment. The key recommendation is to keep the money safe in low-risk accounts rather than pursuing high-return opportunities, emphasizing that maintaining wealth is more important than growing it aggressively at a young age.

  2. 2
    Article
    Avatar of zaidesantonManager.dev·35w

    What's next for manager.dev and for me

    An engineering director shares his 8-month career break experience, exploring entrepreneurship through indie products and startup ventures. After trying to build a parenting app, creating a newsletter monetization strategy, and co-founding a BigQuery analytics startup, he discovered his preference for stability over risk and team collaboration over solo work. He's now returning to full-time engineering management while continuing his newsletter for engineering managers and taking on an evangelist role at a YC startup.

  3. 3
    Article
    Avatar of zaidesantonManager.dev·38w

    Building a $5K ARR Side Project While Managing 9 Engineers

    Taylor Barr shares how he built Delly, a team responsibility visualization tool, reaching $5K ARR and 30+ paying customers while managing 9 engineers full-time. The 18-month journey involved learning new technologies like Svelte, finding initial customers through personal networks, and discovering unexpected business skills. The side project enhanced his engineering leadership abilities and led to a product management role transition.

  4. 4
    Article
    Avatar of sknexusSK NEXUS·35w

    Why So Many Startups Fail

    Explores the primary reasons why most startups fail, with a focus on funding challenges and misconceptions. Covers different types of startup funding and essential knowledge founders need before launching their ventures.