Category Archives: Podcast

Whoop Podcast

Whoop is an excellent biometrics bracelet I’ve been wearing for a few months since my friend Jaime Waydo joined as their CTO. After many years of being very in the Garmin 945 camp, I now do an Apple Ultra for all the smart stuff, and Whoop for all the great sleep, HRV, and recovery information that I use to be aware of my energy levels throughout the day, complemented by the Rise sleep and energy tracker app. This has been my ideal combo.

The founder and CEO of Whoop, Will Ahmed, interviewed me for their podcast, which we covered for a more mainstream audience my passion for open source and creating an open ecosystem for a web, how I got started as an entrepreneur, how Automattic hires, growth mindset and mental clarity, working with Joe Hudson as an executive coach, and day-to-day routine (or lack thereof, sometimes).

Jack Dorsey and Running Two Companies

I had the pleasure of interviewing Jack Dorsey for the Distributed podcast, a conversation that ended up going a bit deeper and longer than previous episodes.

In preparation for the interview I kept coming across people critical about the fact that Jack is the CEO of two companies simultaneously, Twitter and Square, each having over 5,000 employees.

I think what people miss is that at that scale, running a company is not that different from running a large division of a company. No one asks Jeff Bezos how he’s CEO of both a retail company and a cloud computing one (AWS), or Tim Cook how he’s CEO of a hardware business and a services business, and of course with both of those examples the breadth of what the companies cover is much wider. Also as an added benefit, shareholders can choose to invest in Square and Twitter together or not.

All of that said, I think having a CEO-level seat at two of the most influential technology companies today does allow for accelerated learning, as organizational experiments will naturally happen at each company and then the best practice can be shared to the other. Jack wasn’t aware how much peer executives at each company meet with each other to share learnings, but that seems like an obvious win.

Readers of this blog will especially appreciate how much we talked about open source and cryptocurrencies, and his view on the three things he’s responsible for as CEO. Give it a listen and let me know what you think.

Introducing the Distributed Podcast

Distributed podcast

I’ve been meeting with some brilliant people for Distributed, my new podcast dedicated to exploring the future of work. The first episode is a conversation with Stephane Kasriel, CEO of Upwork, about how they built a distributed culture, and how flexible work will shape the future of the global economy.

Unlike Automattic, Upwork does have an office in Silicon Valley (albeit one with a remote receptionist!). It was interesting to hear how Stephane’s teams balance in-person culture with inclusiveness for all employees, no matter where they live. Read more about Stephane’s work at, and subscribe at Apple Podcasts, or wherever you listen to podcasts.