Upper Hand

5Money Talks

I left tens of thousands of dollars on the table when I landed my first role at a new startup company.

After we'd agreed upon my salary (which I'd failed to negotiate), the company offered me stock options. It was the first time ever in my career that I'd been offered equity, and while I understood that it meant I'd have a relatively small ownership stake in the business as I helped to grow it, I was truly out of my depth as to what that looked like from a compensation perspective.

My family was a family of pension plans and 401(k)‐matching programs. We were not a stocks‐and‐bonds or investment strategy–driven family. My peers and friends from undergrad were working for startups of a different sort—having also never experienced being offered equity as part of their total financial package. So my understanding of the equity offer was limited to what I could find on Google, and with the urgency to onboard me as quickly as possible, I said yes to what ultimately reduced my ability to put that forsaken money into long‐term wealth‐building tools.

As co‐workers whispered about the possibility of the company going public as early as the following year, and discussions about what they'd do with their newfound riches arose, I sat silently at my desk, embarrassed that I'd played the game entirely wrong.

I was college‐educated, had read the books by several financial gurus, but when it came to understanding the mechanics of the tech world and its financial structure, there ...