I'm Not Good Enough

Run your own race

My second-grade English teacher told me to stick to math. The neighborhood kids skipped me for cricket. The basketball coach left me out of divisionals. My high school principal compared me to my brothers, and my physics teacher wrote me off after one failed midterm.

The pattern followed me to college. An engineering professor suggested dropping out after a C grade. The CS department wouldn't let me take computer architecture classes. Recruiters fixated on my GPA. Each rejection pushed me deeper into understanding what others skimmed.

Then came my career. Startups demoted me before promoting me three times in a year. VCs laughed when I left big tech, calling me too corporate. Enterprise clients scanned the room for gray hair before listening. Even as I grow into investing, “Tier 1” VCs question how I could understand founders without being one.

Even now, my net worth reminds me of different choices I could have made. My family, too loving to say it, probably wishes I'd done more.

At some point, I realized I'd never be "good enough" for everyone, so I stopped letting it define me. Each "no" pushed me to dig deeper. When I found conviction in my research, I went ahead anyway. Rejection freed me to explore, fail, and grow on my own terms.

These experiences shaped how I evaluate everything. Beyond experience, I look for drive. Beyond market complexity, I look for depth. Behind every resume, every pitch, every meeting, there's someone fighting their own battle of "not enough." Those stories of resilience—they're what I seek now.

When young people look at resumes like mine today, they miss these stories. The moments of doubt, the setbacks, the people who said no. Take time to understand the journey behind the highlights, then find your own path. Your story won't look like anyone else's.