David Pilo's Bloghttps://davidpilo.com/https://davidpilo.com/blog/post/can-you-make-it-uglier.mdhttps://davidpilo.com/blog/post/can-you-make-it-uglier.md"Can you make it uglier?" That's my favorite question to ask when a teammate presents a new design. Humans are wired to love beautiful things. That's not a flaw—it's biology. But in software design,...Thu, 05 Feb 2026 00:00:00 GMThttps://davidpilo.com/blog/post/fire-managers-promote-mentors.mdhttps://davidpilo.com/blog/post/fire-managers-promote-mentors.mdWhen we were a dozen or so at Walcu, I knew that one day, if things went well, we'd grow and eventually need a hierarchy. I dreaded that part. I'd seen this movie too many times: companies whose man...Thu, 22 Jan 2026 00:00:00 GMThttps://davidpilo.com/blog/post/no-business-plan.mdhttps://davidpilo.com/blog/post/no-business-plan.mdUntil Today. One thing that always struck me as outright wrong is to spend time on creating detailed business plans and financial reports/predictions early on when starting a SaaS company. I've seen...Thu, 15 Jan 2026 00:00:00 GMThttps://davidpilo.com/blog/post/head-of-cs-left-last-week.mdhttps://davidpilo.com/blog/post/head-of-cs-left-last-week.mdOur Head of Customer Success left last week. On her way out, she handed us a gift during the exit interview. She said, very calmly, that our biggest problem was that we were doing too much work for o...Tue, 27 Jan 2026 00:00:00 GMT