Few waves have hit the world quite like remote work; a wave impacting billions of people overnight due to a worldwide pandemic.

But in reality, this wave was brewing for decades and thousands of nomads had long been proving there was a different and viable way to work. Calvin and Steph were two of those people, starting in 2016.

Now that the world has caught up, they decided to reflect back on what was so special about that period and what, in retrospect, they might've seen then that much of the world had still not (and in some ways still hasn't) understood.

Listen in for a look inside the early days of digital nomadism.

This episode is not affiliated with Steph's work at a16z and is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. For more details please see a16z.com/disclosures.

Few people inspire us more than Yayoi Kusama.

Cal recently discovered this 94-year old's work while at the Guggenheim in Bilbao. Like many others, he was immediately gripped by her art – enough to be the only artist he looked up after his visit. Little did he know she was one of the world's most successful living artists, had been creating thousands of pieces across nearly a century, and has quite the storied past.

In this episode, you'll learn about this incredible artist, from her long-time struggle with mental health (she has been living out of a mental facility for 50 years!) to her alienation from the art community and Japan, and how she ultimately succeeded beyond all of that noise by continuing to create a gobsmacking amount of art. A true hero's journey. 

It's truly a wonder that we hadn't heard of Yayoi earlier. We hope this episode leaves you just as astounded by her as we are.

Many people waddle through life without asking themselves a simple, but important question: What do I want? 

In this episode, Steph and Cal discuss how to figure out what you want and avoid some common traps that take you down unhelpful detours.

The episode is based on two of Cal's recent articles, which you can read here:

• What Do You Want?
• Calvinball: The Only Game Worth Playing

This episode is not affiliated with Steph's work at a16z and is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. For more details please see a16z.com/disclosures.

Some people argue for tipping. Some people argue against. But the one thing that unites most people with an opinion on the topic is a lack of understanding of where the practice came from in the first place.

In this episode, Cal and Steph walk through the history of tip culture, how that led to vastly different norms around the world, and the confusing place we're left in today – especially in an era of Square terminals and where tipping seems to be infiltrating the unexpected.

Has tip culture gone too far? Listen in to find out.

This episode is not affiliated with Steph's work at a16z and is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. For more details please see a16z.com/disclosures.

The Master Somm test is widely recognized as one of, if not the hardest test in the world. Only 273 people have passed it since it was incepted in 1969, also making it one of the rarest distinctions out there (<0.00001% of the world!)

In this episode, Steph and Cal discuss some of the hardest human feats, from athletics to intelligence to, and whether a healthy ambition can lie behind them.

They also discuss where they've taken things the furthest, and where they're still driven to do more.

This episode is not affiliated with Steph's work at a16z and is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. For more details please see a16z.com/disclosures.

ChatGPT broke records in adoption, hitting 100m monthly active users in a matter of months... faster than any other web platform prior. Even faster than TikTok!

But with fast adoption comes equally swift resistance, surfacing  questions around how this technology is changing the wider world. Should AI models be allowed in schools? How about the courtroom? Do stock image photographers have a fighting chance?

In this episode, Cal and Steph step into the shoes of many people tackling these difficult questions right now. From the middle school teacher to the college admissions officer, to the owners of a stock image sites, or even the head of the Bar Association... how would you respond? What questions would you be asking? 

Listen in to hear Cal and Steph's takes.

This episode is not affiliated with Steph's work at a16z and is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. For more details please see a16z.com/disclosures.

Have you ever looked around your home and thought, "Where did all this stuff come from?!"

Cal and Steph are currently going through this exercise, as they go through their first move in years.

It turns out they're not alone in this feeling of overwhelm and is shared by many others who used to be nomads. The need for *things* is universal, but so is the slippery slope to acquiring too many.

In this episode, Cal and Steph explore why weight of stuff – both physically and mentally – and how our decisions are often unconsciously driven by phenomena like the Diderot and Endowment effects. They also explore how our digital lives, although seemingly benign, can also turn into weights on your life and what simple frameworks they're using to change behavior.

Each January, Steph and Cal sit down to reflect on the prior year and this one is no different. You'll find out their...

1. Best New Idea
2. Best New Life Hack
3. Best New Experience
4. Best/Worst Purchase
5. Best/Worst Trend
6. Best Personal Win/Accomplishment
7. #1 Goal for Next Year
8. Prediction for the New Year

Jumpstart 2023 by doubling down on the best activities and avoiding the worst. It's going to be an awesome year.

PS: If you liked the sound effects in this episode, we found them here.

PPS: Since Steph now works at a16z, please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. For more details please see a16z.com/disclosures.