Category: Leadership

Leadership Moment: Looking in the (gym) mirror I spent last week at the Blackhat security conference, walking the vendor floor, taking notes about what booth designs worked (or not). I had the opportunity to chat with a number of folks, and when I commented on the lack of appeal of some of the themed booths,…

Leadership Moment: Getting Caught Every parent knows that there are two indicators that your child is doing something they shouldn’t. The first is when they go completely silent, to stop drawing your attention to them. The second? When you stumble across them, and they panic, trying to hide whatever they were up to. Your quick…

Leadership Moment: Fickle Elmo If you weren’t paying attention, you might have missed the brief window last week when Elmo’s Twitter account posted vile, antisemitic content. It was ostensibly an account hack, and in one sense, Sesame Street is also a victim here. But they’re a victim who then victimized a lot of people. Usually,…

Lessons from Media: Bad Shabbos First off, a quick review: amazing movie. If you’re Jewish, or know Jews, this should have you in tears of joy. I strongly recommend it; if you’re in Boston, it’s currently playing at The Coolidge. Now, on to some leadership lessons, without giving away the plot entirely. The movie is…

Update: Departed YL Ventures I’ve now officially left YL Ventures. Technically, I was done on June 27th, but I wanted to wait until after July 1st (the company’s annual vesting date for carry, in case there was a change of heart on the other side) to give the update about what I’ll be doing next.…

Leadership Moment: Don’t Re-Blame the Victims As hostages are (finally) being released from Gaza, a friend noted the terms of the deal (30-50 convicted terrorists freed from prison for each hostage), and asked, “But won’t the hostages feel guilty about that exchange rate?” Let me first lay my bias out: I dislike almost everything about…

Leadership Moment: Switching Leaders The New England Patriots ended their season, and within hours had terminated their first-year head coach, Jerod Mayo. Days later, they’d hired Mike Vrabel, the former head coach of the Tennessee Titans. While there are a lot of nuances to this transition, today we’ll simply focus on the dangers of setting…

Leadership Moment: Know Your Environment I recently attended a leadership breakfast with a few notable New England Patriots personalities, and a few comments really stuck out, emphasizing the difference that environments have. Head coach Jerod Mayo noted a difference between the business world, where there might be a wall of text highlighting a companies “core…

Leadership Moment: Veterans/Remembrance Day Today is the eleventh day of the eleventh month. One hundred and six years ago, World War I ended at the eleventh minute of the eleventh hour, and Armistice Day was born. Observed until World War II, it then became Remembrance Day in the Commonwealth of Nations, while the United States,…

Leadership Moment: Elections Have Consequences With the US election around the corner (tomorrow!), it can be a useful opportunity to practice a skill leaders need: the ability to predict the future, and then evaluate later to see what they can learn from. Organizations are often faced with a choice—sometimes one path, sometimes more—and they have…