Money as MacGuffin: Playing the Tech Lottery Game
James Sherrett reflects on a career largely shaped by the “tech lottery game” of compensation: salary plus stock options. He spent his early work years in late-1990s online finance media, then in roles helping companies adapt to the internet, then six years running a startup that failed. What did he learn? He declines to disclose his Slack earnings. A number is less interesting than understanding how the game works. Then he describes how outcomes of the Tech Lottery Game vary based on factors like teammates, investors, fundraising strength, and especially cap tables (share counts, ownership distribution, liquidation preferences, and complex clauses). He compares Slack’s cap table and $27.7B Salesforce acquisition with Mobify’s tangled cap table. He concludes that money is a startup “MacGuffin.” Day-to-day motivation came from teammates, customers, and doing quality work.
00:00 Money And startups
01:25 Salary plus options
02:15 No upside to sharing numbers
03:29 Learning the Tech Lottery Game
05:09 Spotting rocket ships
06:07 Cap table basics
08:06 Comparing two acquisition outcomes
09:23 Champagne Problems
10:53 Money as MacGuffin
12:43 What really motivates
14:50 Thank you very much
