Are Startup Stock Options Like ‘Lottery Tickets?’ A CEO and Former Employee Discuss. And My POV.

Hunter Walk
3 min readMay 11, 2024

The good stuff on the Internet really does occur in the comments!

  1. I shared a post by Ben Werdmuller where he details that a company he used to work for had a recent repricing/restructuring of their stock to better reflect the current state of the company and provide incentives for the team going forward.
  2. Ben’s general POV is that stock options are like lottery tickets and that in most cases it’s a losing proposition for the average employee to exercise them — in fact, he’s never bought his options at any company. He recommends just saving your salary instead.
  3. As you can guess I disagreed (stock options are an important part of startup incentives and over the course of a career, can be quite valuable for employees), but with three reminders/caveats
  • Don’t behave as if they’re worth anything until they actually are
  • Don’t over-extend yourself to exercise them in scenarios which put your financial well-being at risk
  • Remember founders and investors will often find ways to protect themselves that employees/common stock cannot
AI generated image

I thought all that would happen is a few ‘likes’ and a comment or two. But then a CEO jumped in to point something…



Hunter Walk

You’ll find me @homebrew , Seed Stage Venture Fund w @satyap . Previously made products at YouTube, Google & SecondLife. Married to @cbarlerin .