Shit You Don't Learn in School

82. Creating 6-Figure Projects Online (With a FT Job!) Dec 29, 2024

Technology has enabled more people than ever to support their lives via online side projects. Steph is one of the people who understands this world well, having created multiple six-figure projects over the last few years.

In this episode, Cal interviews Steph about her perspective on bringing an idea to life, managing your psychology, maintaining a reputation, how to price projects, and doing all of this while working a full-time job.

Check out Internet Pipes: https://internetpipes.com/
Discount Code: SYDLIS

Resources:

81. Sprucing Up Your Space (Without Busting Your Budget) Dec 15, 2024

You probably spend more time at home than anywhere else. And how you feel about that time is heavily influenced by the design and functionality of your space.
But how do you create a space that you truly enjoy? Unless you're an interior designer or have the resources to hire one, you may not know where to start and default to keeping things the way they are. That's okay, but what if you could make a few simple, affordable changes to enhance your experience at home?
In this episode, Cal and Steph discuss how a trip to Japan inspired them to spruce up their home after years of not giving this topic much thought. You'll learn about what they did, how they made decisions in a world of infinite choices, how much it cost, and other ideas that may give you a head start if you take on a similar project.
Items Mentioned:

80. 80/20 Experiments in Health Dec 01, 2024

You’ll be hard-pressed to find someone who doesn’t say their health is paramount, yet you'll be just as hard-pressed to find someone who knows what to do to "get there". While every person’s health journey is going to be unique, in this episode Cal and Steph share their experimentation across many of the major categories – from sleep to supplements and beyond.

Of course, this podcast is for information purposes only and is not health or medical advice. Always consult a healthcare professional for any medical concerns or questions.

Topics Covered:

6:53 - Foundational elements
8:52 - Morning routine
13:24 - Sleep
24:30 - Pain and injury
31:30 - Supplements
38:16 - Mental health
39:31 - 80/20++ (blood work, CGMs, fertility, CO2 monitors)

Additional Resources:

Patrick Collison’s pollution page
Casey Means on Huberman Lab on 7 indicators metabolic health (time-stamped)
CGM tracking template
Cal’s sleep gear: eyemask, silicon earplugs, pillow

79. Running Toward a Healthier Life Nov 17, 2024

Everybody warns you that your body slows down with age, but that deterioration so sneaky, we continue to convince ourselves that we’re doing just fine.

At least, that’s what happened to Steph over the past decade, going from an athlete in her youth to waking up one day without the fitness she once remembered. This episode is a walk through that story, but more importantly, how she got back on track and just ran her first half-marathon. This year, she’ll surpass over 500 miles and next year, the aim is 1000+.

The best part is? This cornerstone of all our lives – health, that is – is possible for all of us to turn around.

Steph’s training modeled after this article
Want to join Steph on her goal for 1000 miles next year? Join this Strava group. (No need to be in SF, Strava just forces me to choose a location!)

78. Navigating the Best Country in the World Nov 03, 2024

In part 2 of our series in Japan, we dive into the how behind planning a trip there, from what is worth seeing, how to navigate the epic train system, their unintuitive review system, and more.
After traveling to 40+ countries each, we’ve found Japan to be a unique beast, and hope this helps you navigate one of the best countries in the world.
If you missed part 1, start there!
Resources discussed:

Full list of Japan recommendations (in different cities) 📌
Pico Iyer’s Beginner’s Guide to Japan
Don’t forget to look out for takkyubin (luggage transport)!
Tabelog for reviews
JR pass calculator
Suica card
Airolo e-sim
Japanese konbini
- Reddit recommendations here and here
- Listicle here (the custard at #7!)
Kappabashi kitchen district
Mount Fuji hut list
Naoshima Benesse House
Recommended ryokans:
- Yoshimatsu
- Yamanochaya
More city-specific recommendations in the guide

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.

77. The Good, Bad, and Weird of Japan Oct 27, 2024

We’re back with a whole new season. In our first episode back, we discuss everything from the wonderful to the wacky of Japan.
You'll hear about an epic art island, specialty coffee and konbini (AKA convenience store food), 100+ year-old businesses, the philosophical ideas that make Japan such a distinct place, and much more.
In our next episode, we get tactical and break down exactly how we would plan a future trip to Japan, in case that's something you've got on the horizon.

Resources discussed:

Full list of Japan recommendations 📌
Pico Iyer’s Beginner’s Guide to Japan
Episode on Yayoi Kusama
Ivy’s post about Japan
Akiya websites: Akiya Banks and All Akiyas
Glitch coffee shop: Ginza and Chiyoda
Cokuun coffee omakase
Cocktail omakase: Bar Cacoi
Recommended ryokan: Yoshimatsu
Cattle tracking website (need ID to use)

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.

76. The Half-Baked Business Idea Roast: Sensory Museums, Zyn Tins, Unrecordable Spaces, and Much More Nov 05, 2023

This is the 10th episode back for SYDLIS, so if you want us to continue creating new episodes for the podcast, let us know by leaving a review at ratethispodcast.com/learn.
In this episode, Steph and Cal bring a medley of half-baked business ideas to the table. They introduce the origin story of each idea, rate it on a scale of A-F, discuss modifications that would make it better, and most importantly, roast each other when the idea is a little too half-baked.
This episode is a part of the broader nudge Steph and Cal push for everyone to see that there are endless ideas to pursue when you learn to see them in the world.
Business ideas covered:

Marketplace for premium goods
Hot sauce tasting kits
Long-duration gifting platform
AI-powered collectible evaluators
The upgraded ZYN tin!
Unrecordable digital spaces
Making friends as an adult workshop
Bidirectional poll-based newsletters
Hyper-localized surf guides
Immersive, animal sensory museums

75. Identity: The Strongest Force in the World Oct 15, 2023

There is something out there that can make one person more productive and kind, while another inharmonious -- even resentful. That thing is identity.
And while we passively adopt parts of identity, we often forget that much of our identity is left up to us. In this episode, Cal and Steph explore the depths of identity and how being intentional around what parts of your identity you adopt, shed, or embrace can lead to a more fulfilled life.

74. Opportunity is Everywhere: Using Twitter, Wikipedia, Patents, & Niche Databases to Discover Trends Oct 07, 2023

The internet has a treasure trove of information that you can use to generate business ideas, spot trends, and understand what the future will look like before everyone else. But to benefit from the internet's wealth of knowledge, you need to learn how to use it in the right ways.

In this episode, Cal and Steph discuss four unconventional ways that you can use the internet to find good ideas for businesses and products that people actually want.

You’ll learn how to:

Use Twitter searches to discover products that people want
Tap into a rich reservoir of unsolved problems with Wikipedia
Leverage a sci-fi technology database to dream up the future
Leverage patents to see what companies are investing in

Resources Mentioned

Wikipedia’s list of unsolved problems
Patent Drop newsletter
Not Boring Sci-Fi Idea Bank and further reading on the database
Twitter Searches
- "request for product" min_faves:200
- "someone please build" min_faves:200
- "I’d pay for" min_faves:200
- “why doesn’t this exist” min_faves:100
- "business idea” min_faves:1000

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.

73. Writing to Save Your Life Sep 30, 2023

Writing is one of the most powerful tools on Earth. But few have mastered the craft.
Perhaps because success in writing often actually veers you off course, leading you to a life of talking instead of living -- the very thing that drove the quality of your writing in the first place.
One man -- (who has written several novels, thousands of poems, and hundreds of short stories) has some merciless takes on the art of writing. And although merciless, many ring true.
In this episode, Cal and Steph dive into the mind of Bukowski and the key lessons we can learn about creating art that truly shakes you alive.
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.

72. Inside the Early Days of Digital Nomadism Sep 24, 2023

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.

71. The Most Influential Artist You've Never Heard Of Sep 18, 2023

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.

70. What Do You Want?! Sep 09, 2023

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:

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.

69. Tipping Culture: Have We Gone Too Far? Sep 02, 2023

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.

68. The Cost of Excellence Aug 26, 2023

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.

67. The Long Road to San Fransisco Aug 19, 2023

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; 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.

66. The AI Debate: Where Do You Sit? Feb 16, 2023

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.

65. Finding a Life Partner Feb 10, 2023

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 an era dominated by apps.

64. The Weight of Things – From Physical to Digital Jan 19, 2023

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.

63. The Best Sh*t We Learned in 2022! Jan 12, 2023

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

Best New Idea
Best New Life Hack
Best New Experience
Best/Worst Purchase
Best/Worst Trend
Best Personal Win/Accomplishment
#1 Goal for Next Year
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.

62. Opportunity is Everywhere: Lupini Beans, Niche Sports, and More Nov 30, 2022

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've found in everyday things and how they're crafted a curious lens with time.
In this episode, they discuss 6 business ideas:

niche sports like freediving
second-hand LEGO markets
the AI education opportunity
lupini beans: the next healthy snack?
the story behind the music
using the full agave plant

Let us know if you liked this episode on Twitter. If there's enough demand, we'll continue to run it monthly.

61. Is Cheating Ever Okay? Nov 25, 2022

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 experiences of being caught in the act and how it's shaped their perspectives since.

60. Generative AI: The Next Big Thing? Nov 15, 2022

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.
So what comes next for the artists... the writers... the musicians...? No one knows for sure, but in this episode Cal and Steph discuss the exciting new world of generative AI. They discuss what it is (and isn't), the tools they've played with, how culture and trust are shifting, who "wins" in this new world, and what they think might be on the horizon.

Check out Steph's new AI-generated avatar
Check out Calvin's new AI-generated avatar
Lexica prompt database
Nat Eliason's article
Marie Dolle article
Profile Pic AI
AvatarAI

59. Be a Magnet, Not a Jail Nov 02, 2022

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 box (office), and vow they only hire top talent yet pay below market rate... there's power in thinking through whether you're truly focusing on attracting the right people or just trying to prevent wrong behavior.
In this episode, Steph and Cal discuss the mentality of being a magnet instead of a jail, originally inspired by this tweet of Steph's.

58. Money x Relationships Oct 25, 2022

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 the kimono and explore how they deal with and think about money in their relationship. They share their current working philosophy on money and stories about the things they struggle with and are still working on.

57. [Part 3] How to Get Married in 10 Days Oct 18, 2022

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.

56. [Part 2] Love, Marriage, and Monogamy Oct 13, 2022

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 be applied to it
Understand the key difference between animals and humans
The importance of travel and exposure to different ways of living
How narratives drive the adoption of technology

55. [Part 1] The Narratives Behind Love with Amanda Natividad and Marissa Goldberg Oct 08, 2022

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.
She discusses them here with Amanda and Marissa, as they share how they navigated the narratives that underpin love, from engagement to name changes to family involvement and more. Without giving too much away, all three women have found their own unique way forward.

Resources:

The Gottman Institute (for fantastic research-based marriage advice)
Harvard grad speech on committing
A name change service that Marissa recommends
A before marriage list of questions
Post-engagement anxiety article 1
Post-engagement anxiety article 2
Getting engaged made me feel miserable
Amanda's "declaration of interdependence"
Marissa's elopement video

Thank you Amanda and Marissa for joining us! You can find them at...

54. Ask Us (Literally) Anything May 15, 2022

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

Essay about the nuance of privilege
If you liked this episode, make sure to subscribe and leave a review.
To receive the latest updates, follow The Sh*t You Don't Learn in School on Twitter.

53. The Promises and Pitfalls of the Creator Economy May 05, 2022

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"...
Is it the things they build?
Is it the audience they have?
Is it the money the make?
They also cover upcoming trends that they expect to hit this growing "creator economy" including the rise of digital influencers, content automation, crypto, and gaming.
If you'd like to ask Cal or Steph a question for an upcoming AMA episode, we encourage you to submit your questions here!

52. Deciding Where to Live with Endless Choice Apr 13, 2022

We all know that where you live is one of the most important decisions you can make, but it may be more important than you think. And with more people working remotely, there is no more freedom than ever in deciding where you call "home."
In this episode, Steph and Cal discuss how to think about where you should live, why it matters more than you think, and how you can make a decision when it involves two people who have different desires from a location.
In one of our next episodes, we'll be answering listener questions! You can ask your questions here:
Next Steps

Paul Graham's essay: http://www.paulgraham.com/cities.html
If you liked this episode, make sure to subscribe and leave a review.
To receive the latest updates, follow The Sh*t You Don't Learn in School on Twitter.

51. The Life You Could've Lived Mar 28, 2022

Life feels like a bunch of micro-decisions, yet a few macro-decisions often end up determining how you spend most of your time.
Perhaps one of the most significant are the degree you choose and the first job you take. The decisions that follow those are inevitably pulled by their inertia.
In this episode, Cal and Steph discuss the importance of exploring the diversity of jobs out there and how many people become fixed in a singular path.
If you liked this episode, make sure to subscribe and leave a review.

50. Making a Difference During Wartime Mar 19, 2022

We believe that the desire to give is universal, but is just as much a skill as anything else in life. In this episode, Cal and Steph discuss the how you can make a difference during your limited time on this earth, with the limited resources you have -- especially during times like these.
They dive into...

Creative ways that people have supported Ukraine
Striking a balance between hedonism and altruism
Making difficult problems tractable
A breakdown of the gender pay gap
Impact starting with small actions
WTF is effective altruism?
Whether charities should be structured differently

If you'd like to join us in giving back, we're giving to givewell.org.

49. The Hidden Power of Language Feb 19, 2022

Language is one of the most powerful tools that humans have accessible to them.
Don't believe us? Consider the fact that someone could walk up to you and say something that could immediately change your mental state.
Nothing around you has changed, other than the words echoed through the air.
In this episode, Cal and Steph discuss the power of words and how language can shape the way we think. They use untranslatable words to convey these concepts and share how language has been shown to impact anything from our impression of time, space, or even emotional regularity.
If you're interested in digging into this more, Steph has built a directory of untranslatable words (Eunoia, which itself is an untranslatable word) and has written an article about the topic here. Send us a message with your favorite "untranslatables"!
Liked this episode? Make sure to subscribe and leave a review.

48. It's Time to Leave the Casino Feb 11, 2022

The allure of getting rich quick is intoxicating.
It's even more intoxicating when you're trapped inside and it seems like all your friends have cashed in big.
In this episode, Cal and Steph discuss Cal's experience with active investing over the last 20 months and ultimately, why it's time to walk away from the casino.
If you liked this episode, make sure to subscribe and leave a review. You can also read Calvin's article on the topic here.
And if you're also stuck in the casino, don't be afraid to reach out to Cal or Steph on Twitter. We'd love to hear your story.

47. What Can Happen in 300 Years? Feb 05, 2022

"The only constant is change", they say.
In this episode, Cal and Steph discuss just how drastically the world has changed and will continue to change.
From the iPhone... to the Internet... to antibiotics... to human flight... to to the sequencing of DNA... to perhaps the most important fact that humans now live more than double as long... these developments all happened within the last 100 years.
Given that things within a single lifetime can go from being inconceivable to ubiquitous, it's mind-blowing to imagine what might be come.
They use the remainder of the episode to explore what might be to come, whether it be proactive medicine, computer-brain interfaces, printed food, digital warfare, and much more.
If you liked this episode, make sure to subscribe and leave a review.
Resources:

46. The Life Lessons You Shouldn't Ignore Jan 24, 2022

There's an endless sea of advice online.
Whether it's from a vague Twitter thread or a clickbait blog post, the advice sounds catchy, but if we're honest... often holds little water.
However, we all know from experience that the right lessons, sometimes even sitting in plain sight, can genuinely change the trajectory of one's life.
In this episode, Cal and Steph discuss the few pieces of advice that they think matter most and shouldn't be ignored.
Love this episode? Give it a review at https://ratethispodcast.com/learn
Resources:

Calvin's article: https://calvinrosser.com/40-pieces-of-advice/
Josh Pigford's project page: https://joshpigford.com/projects
Doing Time Right: https://doingtimeright.com/

45. Are You Playing Russian Roulette With Life? Jan 15, 2022

In this episode, Cal and Steph discuss the hidden side of risk: the infrequent, often unpredictable events that make the biggest differences in our lives.

If you look around, rare, high-impact events are everywhere.

A small number of days in the stock market drive the bulk of the returns.
Large businesses like Google, Amazon, and Best Buy have tested thousands of products, yet have a single profit puppy.
Insurance companies make money on most customers, but have to pay out very large claims to a few people.
A handful of people have had more of an effect on the future than the other 7 billion people combined.

This episode is all about navigating tail risk and tail opportunity. You'll learn how to better avoid the catastrophic events in life, and on the flip side, to take advantage of the life-enhancing opportunities with asymmetric upside.
Love this episode? Give it a review at https://ratethispodcast.com/learn

44. The Best Sh*t We Learned in 2021 Jan 08, 2022

In this episode, Steph and Cal break down the best of 2021. You'll find out the...

Best New Idea
Best New Skill
Best New Life Hack
Best New Experience
Best/Worst Purchase
Best/Worst Investment
Best/Worst Trend
Best Podcast
Creator of the Year
Best Personal Win/Accomplishment
#1 Goal for Next Year
Prediction for the New Year

Jumpstart 2022 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.

43. Technology that People Feared Dec 28, 2021

What do airplanes, railroads, and jazz music have in common? They were all innovations that people feared.
In fact, if you look into any key technology shift from the past, you'll find a wealth of fear, uncertainty, and doubt surrounding it. And while this shouldn't be surprising, we can still learn from the skeptics of the past.
We can learn just how difficult it is to predict what's to come and look toward our future with a humble perspective, an acceptance that we probably will get it wrong again.
In this episode, Calvin and Steph talk through how people viewed inventions seemingly as innocuous as the bicycle or teddy bear, what we can learn from these stories, and how to stay open minded and capitalize on opportunities as technology takes us into the future.

42. Special Episode: Finding Meaning in Sudden Death Nov 29, 2021

Death is universal part of the human experience. During our lives, we often must confront the painful reality of death around us, and eventually, we face that reality ourselves.
What's odd is that despite death being at the core of the human experience, many people avoid talking or thinking about it. So when people pass away or we face a health scare that brings us into contact with the fragility of life, we often don't know what to do.
In this episode, Calvin shares his experience with the death of two close loved ones: his mentor and his mom. He dives into the depths of those experiences, whether it's choosing to take his mother off life support or the psychedelic experience that helped him process his guilt. And most importantly, he shares what he's learned from years of grieving.
We hope this episode serves as a jumping off point for people to speak more openly about death and to connect with the many people that have lost a close loved one.
As a disclaimer: If you are unable to listen to difficult topics like suicide, mental health, or sexual abuse, please do not listen to this episode.
Resources:

41. The Future of Work: What Comes Next? (Part 2) Nov 16, 2021

In the second part of this series on the future of work, Steph and Cal dive into new products and services, alongside macro trends that they predict are in full flux.
These include mass migration, global tax infrastructure, opportunities for services to specialize, increased isolation, UBI, and of course... the metaverse. :)

40. The Future of Work: What Comes Next? (Part 1) Nov 09, 2021

People say that COVID was an accelerator, forcing trends that may have taken decades to develop, to instead take hold in much less time. Remote work was one of those trends. But we're not done yet!
The future of work is constantly evolving and it doesn't just impact whether you can Zoom without pants. :)
In this episode, Cal and Steph discuss the second and third order effects of the remote revolution and what's to come. And in part one of this series, they discuss how this equation impacts the individual and companies. In part 2, they'll talk about new products and services, and macro trends to come.

Resources:

Printable user manual prompts: bit.ly/user-manual-questions
Steph’s user manual: bit.ly/steph-smith-user-manual
Calvin’s user manual: bit.ly/calvin-rosser-user-manual

39. 80/20 Habits, Beliefs, and Products Oct 14, 2021

The information age gives us access to so much advice that it can be hard to see through the noise.
4AM morning routines that don't make sense for you. Productivity hacks that hardly move the needle. Hindsight bias cloaked as success stories.
Most advice is well-intentioned, but rarely translates to improvements in another person's life. So this week, Cal and Steph took a step back to ask the simple question: what are the 80/20 habits, beliefs, and products that had an outsized impact in changing their lives.
While many of their answers aren't revolutionary, they're universal and can be adopted by anyone.
If you find yourself looking for an 80/20 episode that cuts through the noise, this one is for you.

38. Open Salaries and Solving for an Equitable Workforce Sep 30, 2021

With the exception of a few companies like Buffer and GitLab, 99.99%+ of companies opt to keep their salaries closed. This closed nature creates information asymmetry and at times, inequity in the workplace.
Lack of transparency gives companies a hall pass to not develop a robust compensation system, but at the same time, sharing salaries openly isn't without its pitfalls, including privacy and the tendency for people to over-compare themselves to others.
In this episode, Steph and Cal debate whether companies should share their pay methodology or even fully open up their book. They share a range of studies, including results from Norway, a country that has shared their tax returns publicly since 1863.
If you've felt the information asymmetry in the workforce or are considering how you can get more out of your career, this episode is for you.
Love this episode? Give it a review at https://ratethispodcast.com/learn

37. Should Billionaires Exist? Sep 19, 2021

Wealth inequality has been increasing for decades, and recently, there has been a heightened focus on billionaires as we debate what to do about the concentration of large swaths of wealth in a few hands.
In this episode, Steph and Cal discuss whether or not billionaires should exist, common proposals for dealing with billionaires, and a few policy proposals for how we can start thinking about tackling wealth inequality.
Whether you find yourself saying, "billionaires are evil and don't deserve all that money", "billionaires deserve what they have earned", or "I don't care about billionaires, but I care about a world with more equality of opportunity," this episode is for you.
Love this episode? Give it a review at https://ratethispodcast.com/learn

36. The Psychology of Pricing Sep 12, 2021

In this episode, Cal and Steph discuss the subjective nature of pricing. They explore how a value extends beyond utility or the physical nature of an asset (think luxury items, NFTs, etc) and use these ideas to explore new pricing models, including tiered, retention-based, and completion-based pricing.
They also explore how our own psychology can inhibit use as consumers to spend on what's most meaningful and the importance of unlearning certain spending habits.
If you find the psychology of money as fascinating as we do, give this episode a listen.
Love this episode? Give it a review at https://ratethispodcast.com/learn

35. Does Marriage, Retirement, or the 40-Hour Work Week Still Make Sense? Sep 04, 2021

In this episode, Steph and Cal dive deep into traditions, the societal defaults that shape how we think and act in the world. They start by exploring the origins of the 40-hour work week, modern alternatives, and how we can rethink the idea of retirement. In the second half of the episode, they explore how the ways in which commonly held beliefs about monogamy, love, and marriage may not set people up for the life they want to live. If you're interested in questioning the norms and designing a life that works for you, this episode is worth a listen.
Love this episode? Give it a review at https://ratethispodcast.com/learn

34. Rethinking Productivity & How You Spend Your Time Aug 07, 2021

The big failure of most productivity advice is the focus on efficiency – getting things done more quickly. We should be focused on effectiveness – making sure we're doing the right things. In this episode, Steph and Cal explore how we can rethink productivity to get more out of how we spend our most valuable resource: time. They cover a variety of topics, including many practical ideas about getting more out of every day, including the Eliminate, Automate, Delegate, and Iterate framework from their new course: Doing Time Right.
You can dive deeper into the concepts discussed and learn more about the course here: http://doingtimeright.com/.
Love this episode? Give it a review at https://ratethispodcast.com/learn

33. Digital Security – Are You Safe? Jul 05, 2021

We're all familiar with how to increase physical security – locking our doors, paying attention to our surroundings, putting valuables in a safe, etc. – but what about our digital security?
With an increasingly digital world comes a less perceptible risk – the risk of having your information hacked and exploited by someone with whom you will never see or interact.
In this episode, Steph and Cal explore the basics of digital security, the risks involved, where many people go wrong, and what you should consider doing at a minimum to move from "at-risk" to "safer" with your digital information.
See if you've been hacked: https://haveibeenpwned.com/.

32. Are We in a Bubble? Jun 28, 2021

At a time where several asset classes are at all-time highs, there's a lot of talk about whether we're in a bubble. That, coupled with crypto assets falling to ~half of their highs, prompted Cal and Steph to dive in to try to answer this question.
In this episode, they discuss the markings of past bubbles, the innovation hype cycle, the difficulty in profiting from nascent innovations, the importance of educating yourself and building your own conviction behind your decisions, managing your psychology (offense vs defense), the cyclical nature of market cycles, and of course... the burning question of whether they think we're in a bubble today.
They also share how they've fared in crypto and how they're thinking about investing moving forward (including Cal's foray into de-fi)
Recommended resources include the books "The Simple Path to Wealth" and "A Random Walk Down Wallstreet", as well as economic indicators like the Shiller PE ratio: https://www.multpl.com/shiller-pe
*** NOT FINANCIAL ADVICE *** :)

31. Surprising Travel Hacks From Visiting 70+ Countries Jun 17, 2021

Travel is fun, but it becomes even more enjoyable once you know how to do it well. Collectively, Steph and Cal have visited over 70 countries while working remotely, learning a bunch of useful tips for better travel along the way. In this episode, they share some of the most useful learnings, including:
- How to avoid getting scammed
- How to choose a location and plan a trip
- How to choose an accomodation that's suitable for work
- How to interact with a place
- How to get the most out of visiting different countries
- How to optimize your personal finances
- And more...
Episode Resources

Nomad List - Find a cool location to visit.
Message to Airbnb host to ensure good wifi - Make sure you have good wifi.
Schwab Bank High Yield Investor Checking - No foreign ATM fees.
Chase Sapphire Reserve Credit Card - All around great travel card.
Priority Pass - Access airport lounges worldwide.

30. Was 30 Pods in 30 Days Worth It? Jun 09, 2021

30 days ago, Calvin and Steph set out to record 30 pods in 30 days. Today was the final episode of their challenge, where they reflect on what went well, what didn't go so well, and if they plan to continue recording.

29. Grappling with Unintended Consequences Jun 08, 2021

The world is run by incentives, but what happens when those incentives go wrong? In this episode, Calvin and Steph talk through the Cobra Effect, a phenomena incentives designed to improve society actually end in negative consequences, often resulting in actions counter to the original goal. They discuss several examples of the effect and how people can not only be more aware of it, but also how they can design better incentive structures moving forward.

28. How to Quit Drinking Alcohol and Still Be Happy Jun 07, 2021

Drinking alcohol is embedded within the social fabric of society, but how do we take control of our relationship with alcohol? For all of the fun it supports, alcohol is a poison that causes unnecessary physical, mental, and emotional harm for many people. In this episode, Steph and Cal interview Taylor Platt, a Princeton graduate and NBA strategist who went sober 3 years ago. Taylor shares why he made the decisions, how he did it, the challenges he faced, and what he learned that might be helpful for you. If you're at all interested in reducing your alcohol or reconsidering your relationship with it, this episode is worth a listen.

27. Earning the Trust of Your Team Jun 06, 2021

Whether we'd like to believe it or not, age is a signal that people judge others by. In a professional setting, it can signal your level of experience and for that reason, it can be difficult to earn the trust of a team, if they happen to be older than you. In this episode, Calvin and Steph talk through their experiences managing at a young age and what tips they have for effective leadership.

26. The 3X Rule and When You Should Splurge Jun 05, 2021

In recent episodes, Calvin and Steph have discussed lifestyle creep and how when you make more, you have the tendency to spend more. In this episode, they brought on a friend and colleague Ethan Brooks, to discuss in what circumstances it does make sense to splurge. In particular, they discuss their experiences in hostels and when it was time to upgrade.

25. How to Make Your Stuff Work For You, Not Against You Jun 04, 2021

We all accumulate possessions throughout our lives, but how often do we evaluate whether or not all that stuff is helping or hurting us? In this episode, Steph and Calvin talk about what they learned from living out of backpacks for 4 years, how expensive items carry a psychological burden, and how to think about what you buy over time.

24. Overcoming Imposter Syndrome Jun 03, 2021

No matter how talented you are, you'll inevitably be a victim of imposter syndrome. But, there's a flipside to every coin and for imposter syndrome, it's the compulsion to always be better. Is is possible to get the upside and limit the downside?
In this episode, Calvin and Steph discuss how they've managed imposter syndrome and balance their ambition to improve, with the tendency to compare yourself to others.

23. Is the World Actually Getting Worse? Jun 02, 2021

Most of us walk around thinking that the world is getting worse. But is this actually true? In this episode, Steph and I walk through a quiz that shows us just how wrong our instincts are about the state of the world and why we consistently believe that things are far worse than they actually are.

22. The Importance of Tech Literacy Jun 01, 2021

As technology becomes more ingrained in our daily lives, the question must be posed: how important is it for people to “keep up” technologically. In this episode, Steph makes a case for the importance of tech literacy and how she believes that with time, technical literacy will be viewed in a similar vein to written and oral literacy today. Calvin and her walk through how people can start dipping their toes into technology, why it matters, and discuss what skills may fade with time.

21. What is Financial Freedom and Are You There Yet? May 31, 2021

Whether we'd like to admit it or not, finances have such a significant impact in our lives, both in micro and macro decision making. We also can't ignore how people have different relationships with their wealth, even at the same level of income.
In this episode, Calvin and Steph talk through the concept of being "post-economic", how they think about their "f*** you money" number, and how they manage their relationship with money.

20. Will FAANG Be the Dominant Companies Forever? May 30, 2021

Facebook, Amazon, Apple, Netflix & Google (FAANG) have dominated and become integrated parts of all of our lives in the software era. But if you look at history, time and time again, the leading companies of the present aren't the leading companies of the future. In this episode, Steph and I explore the areas of innovation that might produce companies that displace FAANG and how those companies may approach attracting the best talent.

19. How the Fundamental Attribution Error Impacts Your Relationships May 29, 2021

Among the many biases that we can fall prey to, one of Calvin's favorites is the fundamental attribution error. The bias, sometimes known as the "correspondence bias", is your tendency to assume that someone's behavior is due to the "kind" of person they are, rather than the circumstances impacting them.
In this episode, Calvin and Steph discuss the cognitive bias, why it matters, and how we can combat it.

18. What Does it Take to Become World Class at Something? May 28, 2021

With 7 billion people on Earth, it's incredibly hard to be at the absolute top of any field. In this episode, Steph and Calvin discuss what they learned from their brief stints of being "world-class" in chess and golf, respectively. They also dive into the 10,000-hour rule, mastering skills in adulthood, and managing your psychology along the way.

17. The Individual Contributor vs the Manager May 27, 2021

In most companies, there are two major role types: individual contributors and managers. The career track goes one way and not the other; IC upleveling to a manager. But is that the best way? Calvin and Steph share their stories as both ICs and managers, and think through how companies can get the most from their uniquely talented individual contributors.

16. Will People Rush Back to the Office? May 26, 2021

As a follow up from episode 14, Calvin and Steph debate what work life will be like post-pandemic. Will people rush back to the office? Or will they bask in their newfound flexibility?
Listen in to find out how they think both companies and individuals may progress over the coming years!

15. What is Integrity & Why Does it Matter? May 25, 2021

Codifying and living by your values is one of the most important skills of adulthood. Values are the guideposts that help you make decisions that align with who you want to be, especially when you're confronted with difficult situations. In this episode, Steph and Calvin dive deep into integrity, how to think about values, and what this means for individuals and businesses.

14. Lessons from Years of Location Independence May 24, 2021

The pandemic resulted in hundreds of millions — if not billions — of people moving their work online. These rapid changes mean that so many people now have the freedom to work and live from where they want. Calvin and Steph had the privilege of being location independent since 2016, so in this episode, they break down the most important lessons they’ve learned about being happy, productive remote workers.

13. How to Say No More Often May 23, 2021

Even if we’d like to wish otherwise, our time is finite and zero sum. If we spend time on one thing, we’re not spending time on another. But even though it’s our most scarce resource, we often don’t protect it by saying “no”.

In this episode, Calvin and Steph discuss why it can be so difficult to say no and how we can develop the muscle to say no more often.

12. When is it Okay to be Late? May 22, 2021

Some people are never late. Others are late consistently. Why is there such a difference in people’s relationship with time?

In this episode, Steph and Calvin talk about chronically late insane people (CLIPs), a term coined by Tim Urban. They talk through when it’s okay to be late, when it’s not, and why some people can’t seem to be on time, despite feeling bad about it.
Steph also shares her experience as a CLIP and they discuss the four different types of chronically late people, along with how this behavior may differ around the world.

11. The Pitfalls of Zeroism May 21, 2021

The pandemic has been a fascinating case study in problem solving, yet remains a topic that parts of the world is deeply divided on. Just like other controversial topics, understanding that there is no perfect solution is both accurate and freeing.
In this episode, Steph and Calvin explore the idea of zeroism, or said otherwise, the pursuit of perfection. By identifying the tendency for humans to strive for perfection, they highlight the ways that thinking in absolutes can hinder our ability to make progress.

10. How Your Relationship with Money Influences Your Investing Decisions & Strategy May 20, 2021

We all need money, but formal schooling fails to teach us how to make decisions based on our unique relationship with money and investing. In this episode, Steph and I openly explore the challenges we've had with investing our money and the many pitfalls we've tried to avoid in our pursuit of building sustainable, long-term wealth.

9. Navigating the Complexities of the Modern Era May 19, 2021

We have access to more data and opportunities than ever before, but it's hard to separate the signal from the noise. In this episode, Steph and Calvin discuss navigating information overload, how to avoid being left behind, what we can learn from the past, and how we can better prepare for an uncertain future.

8. Staying in Touch with Friends and Family in Adulthood May 18, 2021

Friendship, family, and community are indispensable to living a good life. But as we get older, it becomes more difficult to stay in touch with the people we care about. Life seems to always get in the way. In this episode, Steph and Calvin chat about the challenges of staying in touch with people, some tactics for doing a better job, and the importance of prioritizing this part of your life.

7. How to Build a Rewarding Career & Minimize Regret May 17, 2021

It's hard to make career decisions. What industry should you work in? What should you optimize for? When should you quit your job? In this episode, Steph and Calvin talk about how they've thought about navigating the endless nuances and ambiguities of building a rewarding career.

6. Learning How to Give Back in Ways That Resonate May 16, 2021

Like everything in life, giving back is a skill and a habit that takes time to learn. In this episode, Steph and I talk about how we define giving, the ways in which we've experimented with giving back, and how you can get started giving even before you're ready to give.

5. Mastering the Art of Learning New Skills May 15, 2021

We all want to learn new things, whether it's how to cook, speak Spanish, write, code, or surf. But how often do you follow through and actually make progress on learning the skill you say you want to learn? Not often enough. In this episode, Steph and I discuss how we approach learning new skills and how you can get better at translating your desires into reality.

4. Should Remote Companies Pay People Based on Location? May 14, 2021

With more companies going partially and fully remote in the wake of the Covid-19 pandemic, Steph Smith and I tackle the difficult question: Should companies pay everyone the same salary, independent of their location, or should salaries be adjusted based on your location?

3. How to Think About Improving the Quality of Your Sleep May 13, 2021

We all know sleep is important, but how should you think about sleep and investing in improving the quality of your sleep? In this episode, we explore how we're approaching sleep, thinking about how to improve it, and measuring the results.

2. How to Deal with Comparing Yourself to Others May 12, 2021

We all compare ourselves to others, but when you compare, you despair. In this episode, we explore the origins of comparing yourself with others, the specific ways in which it can manifest in your life, and how to mitigate the harmful effects of comparing yourself with others in life and business.

1. Don't Let Bad Days Become Destructive Days May 11, 2021

Everyone has bad days. You may be tired, stressed, or dealing with a difficult time. That's human. But if you want to succeed in the workplace, a meta-skill is ensuring that these bad days don't snowball into destructive days. While you can shake off a bad day, a destructive day can have lasting damage and is totally avoidable.

How to Retain and Apply Lessons from Nonfiction Books May 30, 2020

In this episode, I discuss a system you can use to better understand, retain, and apply the information you read in nonfiction books. If you want to expand your knowledge, solve problems, or deepen your understanding of the world, this system will help you do so.

Costly Investing Biases & How to Avoid Them May 23, 2020

A rational investor maximizes his wealth within the constraints of his risk tolerance. Most investors are not rational - they're driven by greed, hope, fear. That is, they're human.
To invest smartly and avoid loses money unnecessarily, you need to learn how to manage the natural weaknesses in your psychology. This episode explores 5 common biases that plague investors. It also explores how to mitigate the risk of falling victim to these biases.

Crush Your Next Job Interview - 6 Insider Tips from a Hiring Manager Apr 25, 2020

In the last 5 weeks, 26 million people have filed for unemployment. As someone who regularly interview candidates for jobs, I wanted to share 6 insider tips to help you crush your next interview. I explore how interviewers think, common mistakes candidates make, and practical advice about how you can stand out from the crowd.

What the hell is going on with COVID-19? Apr 14, 2020

In this episode, I speak with Steph Smith (@stephsmithio), the Senior Analyst for the popular tech and business newsletter, the Hustle. In our wide-ranging conversation, Steph shares her thoughts about the COVID-19 pandemic and what we can expect over the coming months for life and business.
We also discuss the complex nature of the virus, why the entire world missed its window to react, how these “black swan events” lead to second and third-order effects, why many people may default to optimism, and what data we should pay attention to.
You can find the show notes, which include a bunch of Coronavirus resources, at https://calvinrosser.com/podcast/

Black Beans, Seneca, and Practicing Poverty Apr 11, 2020

In this episode, you'll learn about what eating black beans out of a can has to do with your life. Whether you feel like you're living in abundance or you're just "getting by", this short talk will help you learn how to enjoy living with less.
For all show notes: https://calvinrosser.com/podcast/
For a helpful weekly newsletter: https://calvinrosser.com/newsletter

Coping with the Uncertainty & Helplessness of a Pandemic Apr 10, 2020

In this episode, you'll learn about two drivers of the heightened fear, stress, and anxiety during the current pandemic - uncertainty and helplessness. You'll also learn about how you can reduce your fear and anxiety by focusing on activities within your span of control.
For all show notes: https://calvinrosser.com/podcast/
For a helpful weekly newsletter: https://calvinrosser.com/newsletter

Quarantine Morning Routine - Reduce Anxiety and Increase Energy in Uncertain Times Apr 08, 2020

In this episode, you'll learn about a short and simple morning routine that will help you increase your energy, reduce your anxiety, and feel more relaxed during uncertain and difficult times. You can find the written out routine, in addition to the resources mentioned in the article, at calvinrosser.com/quaratine-morning-routine.
For all show notes: https://calvinrosser.com/podcast/
For a helpful weekly newsletter: https://calvinrosser.com/newsletter

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