
The Bootstrapped Founder 421: Why You Should Never Start a Software Business
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Oct 31, 2025 Discover the harsh realities of starting a software business. Explore the loneliness that solopreneurs face and the pressure of being solely responsible. Learn about the challenges of hiring and customer resistance to change. Understand the relentless need for adaptation as markets shift. Get insights on owning problems, even when they're not your fault, and how to mitigate risks through community and automation. Finally, embrace the hardships as learning experiences that foster resilience and leadership.
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Loneliness Is Built Into Software Work
- Building software businesses can be deeply lonely because most time is spent with code, not customers.
- Arvid Kahl combats this by engaging communities, blogging, and podcasting to feel connected.
2am Server Crashes Feel Personal
- Arvid describes a 2am server memory issue that keeps recurring and forces restarts while customers complain.
- He felt like the sole defender of the castle juggling fixes and customer reassurance simultaneously.
Expect Constant Unplanned Priorities
- Early-stage founders become responsible for everything and must handle unexpected priorities constantly.
- Arvid urges becoming a lightning rod: trigger and learn from failures early to harden systems.
