How to Live & Lead a Rewarding Career (Podcast Interview)

Earlier this summmer I did an interview with David Nebinski for a new Seth Godin podcast fellowship project "Portfolio Career." In it, I shared my thoughts on what it means to have a rewarding career and how you might think about optimizing your pursuit of one. I also talk a little about my own career, … Continue reading How to Live & Lead a Rewarding Career (Podcast Interview)

How to Learn Strategy (When Everything is Strategic)

I happened to be on Quora the other night and noticed a poster asking the question: "What's the best way to learn strategy?" I thought it was a cool (and somewhat daunting) question, so I chimed in and wanted to share my answer here. It also occurred to me that learning strategic thinking has two … Continue reading How to Learn Strategy (When Everything is Strategic)

On Fascism, Identity, Cryptoassets and the Future of Censorship

Today, more people around the world have the ability to exchange ideas and value with one another than ever before. Yet even at this historic height of connectivity and interconnectedness, we live in increasingly complex and alarming times when it comes to free speech, trust and censorship. In the past week alone: The US Federal … Continue reading On Fascism, Identity, Cryptoassets and the Future of Censorship

What Happened When I Called Out 300 Russian Propaganda Trolls on Twitter

They make liberal use of cat photos and emojis, drape themselves in American flag iconography, and go by handles like "Saving America," "4GodandCountry," and "ROCK ON OHIO." And yesterday, scores of them started attacking me online. @ChrisBolman Check out this turd burglar must be sniffing the methane off his dildo's before he types his rants. … Continue reading What Happened When I Called Out 300 Russian Propaganda Trolls on Twitter

Strategy: How to Develop, Structure and Shape a Winning System

Hi, welcome, and yes, I realize the title of this is a bit heavy-handed. While it would be inaccurate and egotistical of me to claim this is any sort of authoritative piece on strategy (if such a thing can even be written), my goal here is to pull together a comprehensive, actionable view of strategy, … Continue reading Strategy: How to Develop, Structure and Shape a Winning System

The Simple $100 Million Dollar Product Strategy

Product strategy is usually hard. Product-market fit is elusive, organizations are complicated, competitors move fast, and culture and technology evolve constantly, forcing strategists to continuously test and refine their work to stay ahead and eke out advantages.   But every once and a while though, a startup comes along that nails product strategy with beautiful, pristine simplicity. … Continue reading The Simple $100 Million Dollar Product Strategy

How to Build a Growth Team: Lessons From the Front Lines

I joined a growth roundtable at First Round Capital last week, which included trategyome really sharp thinkers like Gina Gotthilf from Duolingo and Ashley Berman from Birchbox. It ended up being an enjoyable and illuminating conversation about growth strategy, acquisition and retention tactics, and org design. While it was a closed session -- so I can't share … Continue reading How to Build a Growth Team: Lessons From the Front Lines