Shit You Don't Learn in School

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: SYDLISResources:Josh Pigford's project listPieter Levels’ project listPat Walls’ project list

12/29/24 • 81:24

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:Affordable side table lampsMarshall Bluetooth speaker

12/15/24 • 63:21

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 elements8:52 - Morning routine13:24 - Sleep24:30 - Pain and injury31:30 - Supplements38:16 - Mental health39:31 - 80/20++ (blood work, CGMs, fertility, CO2 monitors)Additional Resources:Patrick Collison’s pollution pageCasey Means on Huberman Lab on 7 indicators metabolic health (time-stamped)CGM tracking templateCal’s sleep gear: eyemask, silicon earplugs, pillow

12/1/24 • 77:08

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 articleWant 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!)

11/17/24 • 56:42

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 JapanDon’t forget to look out for takkyubin (luggage transport)!Tabelog for reviewsJR pass calculatorSuica cardAirolo e-simJapanese konbiniReddit recommendations here and hereListicle here (the custard at #7!)Kappabashi kitchen districtMount Fuji hut listNaoshima Benesse HouseRecommended ryokans: YoshimatsuYamanochayaMore city-specific recommendations in the guideThis 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.

11/3/24 • 83:16

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 JapanEpisode on Yayoi KusamaIvy’s post about JapanAkiya websites: Akiya Banks and All AkiyasGlitch coffee shop: Ginza and ChiyodaCokuun coffee omakaseCocktail omakase: Bar CacoiRecommended ryokan: YoshimatsuCattle 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.

10/27/24 • 77:26

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 goodsHot sauce tasting kits Long-duration gifting platformAI-powered collectible evaluatorsThe upgraded ZYN tin!Unrecordable digital spacesMaking friends as an adult workshopBidirectional poll-based newslettersHyper-localized surf guidesImmersive, animal sensory museums

11/5/23 • 50:45

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.

10/15/23 • 37:35

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 wantTap into a rich reservoir of unsolved problems with WikipediaLeverage a sci-fi technology database to dream up the futureLeverage patents to see what companies are investing inResources MentionedWikipedia’s list of unsolved problemsPatent Drop newsletterNot Boring Sci-Fi Idea Bank and further reading on the databaseTwitter 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:1000This 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.

10/7/23 • 54:55

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.

9/30/23 • 62:54

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.

9/24/23 • 57:04

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.

9/18/23 • 40:25

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 PlayingThis 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.

9/9/23 • 33:37

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.

9/2/23 • 59:55

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 (

8/26/23 • 59:07

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.

8/19/23 • 59:28

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.

2/16/23 • 61:06

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.

2/10/23 • 44:37

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.

1/19/23 • 36:29

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 IdeaBest New Life HackBest New ExperienceBest/Worst PurchaseBest/Worst TrendBest Personal Win/Accomplishment#1 Goal for Next YearPrediction for the New YearJumpstart 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.

1/12/23 • 60:55

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 freedivingsecond-hand LEGO marketsthe AI education opportunitylupini beans: the next healthy snack?the story behind the musicusing the full agave plantLet us know if you liked this episode on Twitter. If there's enough demand, we'll continue to run it monthly.

11/30/22 • 41:57

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.

11/25/22 • 44:18

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 avatarCheck out Calvin's new AI-generated avatarLexica prompt databaseNat Eliason's articleMarie Dolle articleProfile Pic AIAvatarAI

11/15/22 • 66:24

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.

11/2/22 • 43:11

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.

10/25/22 • 62:55

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.

10/18/22 • 63:27

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 monogamyWhat animals within the animal kingdom are monogamousThe history of marriage and when marriage started to be associated with loveExplore the concept of love and whether the 37% rule could be applied to itUnderstand the key difference between animals and humansThe importance of travel and exposure to different ways of livingHow narratives drive the adoption of technology

10/13/22 • 35:43

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 recommendsA before marriage list of questions Post-engagement anxiety article 1Post-engagement anxiety article 2Getting engaged made me feel miserableAmanda's "declaration of interdependence"Marissa's elopement video Thank you Amanda and Marissa for joining us! You can find them at...Amanda's personal siteAmanda's TwitterMarissa's personal siteMarissa's Twitter

10/8/22 • 58:15

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 StepsEssay about the nuance of privilegeIf 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.

5/15/22 • 64:16

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!

5/5/22 • 57:09