When GitHub was acquired for $7.5 billion by Microsoft in June, friends texted Rachelle Gupta, an early GitHub recruiter, to congratulate her on what they assumed to be a windfall from her stock options.

She told them she didn’t have any options. She had unknowingly let her stock options expire, because she wasn’t aware that she had to exercise them within 90 days of leaving the firm in 2015, when she joined the White House’s U.S. Digital Service. She estimated her earnings would have been hundreds of thousands of dollars. “I recruited all these people [who] are millionaires now or have life-changing amounts of money. I have nothing.”