In the early days of Posterous, I focused on external factors like features and funding, unaware that my inner struggles were silently sabotaging the company.

I learned about the golden shadow the hard way during the rise and fall of my first startup, Posterous, where my hidden traits both dark and golden influenced the company's fate.

I gave my co-founder the chance to be CEO at Posterous, but I realized I had the potential to be a visionary CEO myself.

In 2010, despite two years of rapid growth, I failed to accept that our startup's growth had plateaued, which ultimately led to our downfall.

I invested in Twitter after Evan Williams returned money to investors from his failed startup, Odio, showing his integrity and commitment to his investors.

In early 2018, I reached out to Pinterest CEO Ben Silbermann to discuss the future of Instapaper, as I felt it was on a trajectory towards shutdown.

After the acquisition, Reddit struggled to attract the right talent and resources, leading to my departure to start Hipmunk, while Alexis pursued a career in investing.

The acquisition of Twitter was challenging due to significant debt and operational issues, likening it to being teleported into a nosediving plane.

The decision to shut down was influenced by the realization that our initial hypothesis about the business model wasn't panning out as expected.