It took almost six months for my former company IronPort’s acquisition by Cisco to close and it seemed like forever. Although I was still the CEO by name, I was essentially running a “puppet” government with every hire, major expense and strategic shift needing explicit approval from my soon-to-be-overlords. Since Cisco was a functionally organized…
More »“There are a bunch of aggressive, ivy-league educated, high IQ people working in Bentonville whose careers are going nowhere because they never learned how to connect with other people.” — Lee Scott, (now former) CEO of Walmart, circa 2008. During my short tenure at Cisco, I attended a leadership offsite where Lee Scott was…
More »I have so much respect for people who fought online criminals for eBay and PayPal. There hasn’t been a set of websites more highly targeted by cybercriminals and fraudsters. The founders of Silver Tail, Mike Eynon and Laura Mather, were colleagues on the anti-fraud team at eBay/PayPal for three years and had a front row…
More »As a first time CEO, there were times when I would sit at my desk and think, “What should I be doing today?” This feeling was especially strong after every financing round closed. After our seed round, we had defined the product and the engineers were coding it. I didn’t code. After I hired the…
More »My father, Alfred “Bud” Weiss, owned a car dealership—“Bud’s Cadillacs” of Miami, Florida. When I’d drop by the office, he would usually pepper me with bits of business wisdom, but as a kid, I wasn’t very receptive. My father and I are pictured here: My head was usually buried in a comic book, only half…
More »When I was a kid, I read tons of superhero comic books. I fantasized about superpowers, but the storylines about heroes with massive Achilles’ heels really held my attention the most. They saved the world but had screwed up personal lives, made lots of mistakes, and often acted like complete assholes. In retrospect, l related…
More »In 1950, my Uncle Ed Kalin opened a small designer furniture store. After years of hard work, he saved up and opened a larger one. Growing up working there, I’d observe him doing things that, at first, were hard for me to understand. First of all, when he walked around the store, he was constantly…
More »I had a real struggle preparing to be a public company CEO. And it had little to do with having scalable internal systems or making the quarterly numbers… I just couldn’t keep secrets from my employees. As CEO of IronPort, I wanted to be completely transparent with my entire team but my board of seasoned…
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