Shit You Don't Learn in School

Shit You Don't Learn in School

Formal schooling does a terrible job of preparing you to thrive as an adult. The Shit You Don't Learn in School podcast exists to make up for this societal failure. In this show, Calvin Rosser and Steph Smith share stories, insights, and resources designed to help you improve the quality of your personal and professional life. If all works out, you'll be at least 1% better at navigating the waters.


September 24, 2023 57 mins

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 ...

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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 pas...

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September 9, 2023 33 mins

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:

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September 2, 2023 59 mins

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 termina...

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August 26, 2023 59 mins

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 wh...

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August 19, 2023 59 mins
After years of being nomadic, we embarked on an experiment of living in Encinitas. That experiment lasted 3 years, but provided us with a clearer view of what we wanted next.

But could we get past the multi-year stand-off around location and find a place that fit both of our needs? Listen in to find out.

This episode is not affiliated with Steph's work at a16z and is for informational purposes only;...
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February 16, 2023 61 mins

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 thi...

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February 10, 2023 44 mins
One of the most important decisions in life is who you choose to spend your life with, yet it's also one of the hardest things to get right.

Inspired by a recent conversation with a friend that may have unrealistic expectations, Cal and Steph discuss the data behind dating, but also their own very different approaches to it... and if they ever ended up back on the market, how they might do things differently in a...
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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.

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January 12, 2023 60 mins

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 yo...

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A few weeks ago, Steph and Cal had a locksmith come in. It cost $185 and was shockingly quick... just 10 minutes! Little did they know it would also be the fodder for one of Steph's most popular tweets of all time.

Perhaps it shouldn't be surprising people love learning about new opportunities. That's why they decided to record this (hopefully) recurring segment where they share various opportunities they&...

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November 25, 2022 44 mins

There has been a wave of recent cheating scandals, from chess to poker to fishing. But cheating is not new, nor is it a rare occurrence. In fact, some articles sport stats like "75 to 98% of college students have cheated" or "over 46% of respondents in a monogamous relationship said they had affairs."

In this episode, Cal and Steph discuss when if ever cheating is okay. They even share their own exp...

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November 15, 2022 66 mins

For years, people thought that artificial intelligence would wipe out repetitive tasks, but leave the creatives untouched. But recent developments have left many people surprised and taken the creative world by storm. 

Tools like DALL-E, Midjourney, and Stable Diffusion gave anyone with a keyboard and a wifi connection the ability to spin up images from text prompts, far earlier and higher quality than many imagined. 

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November 2, 2022 43 mins

It's human nature to worry about the things that can go wrong.

But often overlooked is the mentality of attraction instead of detraction, or in other words focusing on what you can bring to the table instead of what you can prevent from happening.

While so many companies signal they want entrepreneurial candidates yet don't allow side projects, want out of the box thinkers yet expect them to work in a bo...

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October 25, 2022 62 mins

Money is a leading cause of problems in relationships. It’s not just not having money, it’s conflict around money, lack of alignment, and the downstream effects of that.

Money is complicated because it’s influenced by your direct circumstances, but also by your childhood, psychology, and trajectory. It's also complicated because so few people talk openly and honestly about money.

In this episode, Steph and Cal open up ...

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October 18, 2022 63 mins

In part 3 of our 3-part series, Steph and Cal discuss how they planned a wedding in 10 days, what they did (including traditions kept and scrapped), and the pros and cons of taking a less conventional approach to marriage.

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October 13, 2022 35 mins

In part 2 of this 3-part series, we decided to re-air part of our most popular episode, #35: Does Marriage, Retirement, or the 40-Hour Work Week Still Make Sense?

In this segment, we share:

  • How humans are actually not wired for monogamy
  • What animals within the animal kingdom are monogamous
  • The history of marriage and when marriage started to be associated with love
  • Explore the concept of love and whether the 37% rule could...
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In part 1 of our 3-part series, we're joined be Amanda Natividad and Marissa Goldberg two friends of the podcast to discuss the traditions that surround love.

After getting engaged last year, Steph found herself in a place she didn't expect and with emotions that she didn't feel entitled to have. That led her down a deep rabbit hole of questions, ultimately ending up in a bunch of societal narratives.

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May 15, 2022 64 mins

In this special episode, Cal and Steph answer audience questions across a wide range of topics including writing, relationships, finances, and even death. Listen in to find out.

Next Steps

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Steph has some exciting news to share in today's episode! Listen in to find out.

In this episode, Cal and Steph also cover the rise of the creator economy -- both its promise and pitfalls.

They breakdown why the heightened attention toward creators, whether we can expect a creator "middle class" anytime soon, the importance of IP, and even explore what it truly means to be a "creator"...

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