My Biggest Failure: The Long Overdue Story I was Too Ashamed to Tell

Turn back your mental clock to April of 2012, when Facebook acquired Instagram for the eye-popping price of $1 billion. It was a big story, with headlines all over not just the tech press but mainstream outlets like CNN, Newsweek and the nightly news– who could have imagined a company with barely over a dozen employees commanding a 10-figure valuation?! Like most of you, I watched the story unfold like some kind of tech fairy tale, amazed at what the crew at IG had accomplished so quickly. But my amazement was tempered with shame and regret, because in a not-so-different world, it would have been my company in the headlines. My phone was blowing up and I did my best to patiently answer the barrage of emails, texts, and calls (Yes, I saw the news about Instagram and yes, I know it could have been us).  I laughed it off, but it stung in way that took me a few months to reconcile. It was emotionally draining, because – in large part – my thoughts kept going toward what could have been– and how I let a few simple mistakes throw shade on what proved to be billion-dollar (or maybe … Continue reading My Biggest Failure: The Long Overdue Story I was Too Ashamed to Tell