Category: Leadership

Leadership Moment: Championship Football For the first time since 2018, the Boston Renegades are not the champions of the Women’s Football Alliance. Falling short 30-27 to the St. Louis Slam, the Renegades will start 2025 in a new position: trying to get back on top. It’s easy to denigrate sports teams when they don’t win…

Leadership Moment: Playing Your Cards Right Last week, I was in New York for a CISO dinner with two of our portfolio companies, Valence Security and Aim Security. Yoni Shohet (Valence CEO) pulls me aside before the dinner and says, “I brought you a gift.” Now, I often get a lot of swag from companies…

Leadership Moment: Shields Down Talking with a startup CEO recently, they shared the story of one of their principal software engineers who had just left to join an even earlier stage startup. On the surface, it seemed like a reasonable career choice: after learning that they had what it took to be a key contributor…

Leadership Moment: Choice isn’t Frozen There are times when an organization wants to demonstrate bold leadership on as issue, as the Paris Olympic Committee did when it decided to use geothermal cooling systems instead of more effective air conditioners. Unfortunately for the POC, they didn’t anticipate the entirely predictable consequence: that many countries would bring…

Leadership Moment: Asymmetric Communication Checking into hotels has become increasingly automated. For a recent hotel stay, I received a WhatsApp message from the hotel asking me to provide some pre-checkin information, to smooth the check-in process (reading between the lines: reduce the cost to the hotel to check me in with a human). After a…

Leadership Moment: Product-Led Growth Via SwiftonSecurity (who else), we’re reminded of Bloomberg’s fascinating “get fired” perk: paying customers who lose their job can request a free Bloomberg terminal to bridge them over and maintain currency in the trading network while they seek a new job. In addition to the brilliance of this move (ensuring brand…

Leadership Moment: Firing At the Student Last week, police in Burlington, VT surprised students in a forensic class with a mock mass-shooting simulation. Unsurprisingly, students and parents were decidedly unamused with this event, which was poorly thought through (although the pedagogical goals are interesting: an aim to demonstrate to the students after the event how…

Leadership Moment: D-Day As we observe and celebrate the 80th anniversary of D-Day this week, there’s also a solemnity: this may be the final “interesting” (numerically) anniversary in which living veterans of D-Day participate. As usual, France has rolled out the red carpet for the heroes who through themselves into harm’s way, by sea and…

Leadership Moment: Constraining Authority The Daf Yomi is the practice of studying the Talmud, in a page a day. This last week, the daily page included Bava Metzia 59, one of the key moments in legal leadership in the history of humankind. It starts out really boringly: an argument between the rabbis about whether an…

Leadership Moment: The Perfect is the Enemy of the Now It’s been a crazy month here, and despite some great plans for the newsletter, I kept failing to execute on them – and there’s a leadership lesson right there: sometimes, you build up your own requirements for success so high that, in failing to meet…