Many startup employees do not recognize the sheer litany of ways that a founder can screw you over without you even knowing. Founder trust is one of the most important things to look at when you’re joining a startup.
From cutting you out of M&A, screwing your retention pool, overdiluting your equity, firing you before your cliff, not having attractive options exercise plans, poor 409a price management, not telling you about QSBS / early exercise, blocking you from participating in secondary, obscuring company performance and many more.
Many many decisions that are made in rooms you are not in as an employee where the only thing that matters is: “does the founder have your back?” Great startups with untrustworthy founders lead to poor outcomes and often good startups with trustworthy founders lead to great outcomes.
Pick wisely.
This is crucial advice. I was lucky that as a young engineer attending startupschool in 2011 I got to meet many awesome startups.
I had received this particular advice directly from @billclerico who was himself a first-time founder then.
He and @RichAberman were extremely trust-worthy founders vs. many move-fast types I met. I ended up joining and buying options. And NOT getting screwed when WePay got acquired by Chase.
Sep 4, 2026 · 4:48 PM UTC