Tangential Tuesdays #43

Deep Laziness, Ode to managers, Regulating Emotions: The most important skill no one bothered to teach you

Hi team, I hope your week is off to a good start!

Work has been a bit of a grind lately, some I’m excited to take a much needed vacation (starting tomorrow 😃). Spending some time with my fam back in NH.

As a result, there won’t be a newsletter next week. Trying to take advantage of the tail end as much as possible.

What I’m listening to

🧠 Deep Laziness

As complex as life seems, a typical human’s behavioral repertoire is made up of a small number of behaviors. These few behaviors make up life; they determine feeling and meaning, moment to moment, day to day. While these few behaviors are intricately connected with each other, resisting legible top-down plans, the system is small enough that it’s tractable.

If you ever meet me in person and want to put me at ease, ask me about running or knitting. These are two of my behaviors, my behavioral centers, and one indication of that is how much I like talking about them specifically. I do feel that there is something special about them, and that they connect to my nature on a fundamental level. In my heart, I think everyone should do mountain running and knitting, because they are the best things.

Read the article here.

😃 Regulating Emotions: The most important skill no one talks about

For the bast 6 weeks, I’ve been going to therapy for 1 hour every Monday.

I’ve told almost no one (until now 😊). For whatever reason, I’m at least slightly embarrassed.


  • I have problems, like all humans

  • I have always hated the idea of therapy but been unable to articulate why. Whenever this happens, I take it as a signal that I should try whatever thing I’m questioning

  • I get 6 weeks of free therapy through my job!

Read the article here.

👷‍♂️An ode to managers.

Corporate managers don’t get enough respect. Their image in the popular culture is still based on the one from the 1950s: A conformist drone doing life-draining work, the man in the grey flannel suit—even if he’s a woman and/or gets to dress down on Friday.

To take the most unpleasant example, have you ever fired someone? In Washington there are people who have fired rockets—and many who have written articles urging others to fire rockets—but have never fired a human being. The natural tendency is to think, “I’m much too nice a person to do that sort of thing”—and to feel superior to anyone without such scruples. Yet in an organization of any size there are going to be people who need or actually deserve to be fired. It is hardly the nicest solution to leave that job to someone nasty enough to enjoy it.

👨‍💻 The rise of “No Code”

I’ve been thinking about the recent flurry of “No code” tools. Tools that allow people to create things on the internet without writing code.

There’s bubble, webflow, zapier, airtable, shopify, voiceflow, boundless, and so many more.

I want to love these tools. They lower the barrier to becoming a maker!

But count me as a skeptic. No doubt at least part of my skepticism is some cognitive dissonance due to the fact that some amount of my self worth is tied up in knowing how to code, a skill that no code tools could eventually make significantly less valuable.

For this reason, I’m hoping to dive into the space in the coming weeks to explore if there’s any truth behind my skepticism. I’ll definitely share my much less fabricated opinions with the newsletter once I’ve actually built a few things 😅.

That’s all for this week. As always, thanks for reading.

See you in 2 weeks 😘

- Taylor

Tangential Tuesday #42

The flywheel of life, Shoes, Thumbtack's future, Money !!

In light of me getting back into piano. Some morning tunes.

Lots of exciting stuff to talk about this week. Let’s get into the newsletter 😃🚀.

💸 The flywheel of life

I wrote a thing! In college (and before) my life was mostly planned for me. Many of my high school friends were made before 3rd grade.

College is probably one of the easiest, low effort places to make friends with interesting, ambitious people.

But now I’m in the real world.

Moving to a completely new place where I essentially started with no friends has made me think a lot about how I need to design my life to be happy and successful. Whatever the hell “successful” means 🤷‍♂️.

This article is what came out of all of these thoughts / experiences.

I think you’ll really enjoy it. It’s an idea I’ve never seen expressed in this way.

Read the article here

😅 Blood, sweat, tears and fundraising.

Thumbtack just raised 150 Million Dollars.

I don’t think companies, especially our size should be particularly proud that we needed to raise even more money.

That said, it is certainly validating. 125M came from Sequoia, arguably one of the greatest VC firms ever.

Despite the fact that there are still so many problems to solve, we are in a really good position to capture a large chunk of an absolutely gigantic market.

“This market is multiple times the size of Uber’s market”

This leads me to my 2nd point which is that optimism is extremely valuable. Working at Thumbtack I’ve often found that the engineers and designers are the most critical of the product. When you are heads down grinding on something every day, it’s really easy to forget the bigger picture.

The bigger picture is that we are a 100M+ revenue generating company, in a market with a huge opportunity. Although many people hate our platform, many people also love it. Products like this are incredibly rare. Knowing where your product needs improvement is important, but not letting this fact make you cynical about the future is incredibly important.

I’m excited to see where we go…

Read the article here.

👟 Shoes.

This new luxury brand popped up and it’s super interesting.

The premise: Luxury goods straight from the manufacturer.

I mostly included this in the newsletter but it’s the first thing in awhile where their marketing made me super tempted even though I have never owned (or seriously considered buying) a pair of white shoes.

I also find them interesting because luxury fashion and affordability are not 2 things that often go together. A large part of fashion is based off of exclusivity, either by price , or severely limiting the quantity. Fashion is not rational. People camp overnight in parking lots for a chance to buy certain models of Nike’s. Not because Nike’s are clearly the best quality for the price, but because of the brand Nike has built.

Because brand is so important in fashion, I’m curious to see if italic can cut through the noise.

Atlas Shrugged

I’m ~400 pages into this so far. I’m actually enjoying it way more than I expected.

It’s hard to explain but it’s definitely changed the way I observe the world around me. If you squint a bit, Elon Musk starts to look a lot like Hank Rearden in the modern world.

It reminds me of The Elephant in the Brain where after reading it you can’t help but notice all of the ways people try to signal themselves as “virtuous” or “cultured”.

“So you think that money is the root of all evil? [...] Have you ever asked what is the root of money? Money is a tool of exchange, which can't exist unless there are goods produced and men able to produce them. Money is the material shape of the principle that men who wish to deal with one another must deal by trade and give value for value. Money is not the tool of the moochers, who claim your product by tears, or of the looters, who take it from you by force. Money is made possible only by the men who produce. Is this what you consider evil?”

If this passage seems outrageous you, just remember The Power Of Hyperbole.

I love this rant because it captures how much baggage all of us have about money. If you grew up in the U.S, you likely heard the phrase “Money is the root of all evil” at some point growing up. By the time you actually understand what money is, you have a bunch of preconceived notions about whether it’s good or bad, ethical or unethical, etc.

Many of us forget to ask the question: “Why do I believe the things I believe about money?” Don’t get me wrong, crony capitalism takes place every day. The world is far from a meritocracy. Life is not fair. BUT it’s hard to blame this money.

Ideas from my brain

The idea of a “Full-stack” academy is an idea I’ve been mulling over in my brain a lot. It started with an article I saw about Duo-lingo. Everyone from Bill Gates to refugees in turkey is using Duolingo for language learning. That’s incredible.

But why is this not the case for the rest of education? Why is there still such a gap in opportunities? What would I want higher education to look like if I was designing it from the ground up?

I also know many people who know they want to start a company, but also know they are not ready yet. They want to know what they should be doing now, to set them up well in the future (this is basically me everyone around me in SF).

I think something like this could be taught similar to the way FreeCodeCamp works today. Largely self-taught, mostly project based, and with a firm curriculum in place.

Going to be playing around with this idea in the coming weeks. Let me know if you have thoughts, suggestions, ideas, hopes, dream…

Andrew Yang in Newmarket!

I love this article mostly because it takes place extremely close to where I live, in a bookstore I know very well.

Andrew Yang is also interesting. I don’t buy into most of his ideas, but I’m still a huge fan.

“Yang likes to say that Trump got all the problems right but offered the wrong solutions.”

Read the article here.

More to check out

Compound <— props to Jordan + Jacob on 1st launch!

Billionaire’s 2005 ‘Almanack’ of sage advice finds an audience in S.F. tech world

An Elite Athlete’s Real-Life Training Plan

Thanks for reading. Time for bed 🛌. Have a spectacular week.

- Taylor

Tangential Tuesday #41

Specialists v Generalists, Platforms v Aggregators, Online dating, How to train for knowledge work...

“Every living thing must grow. It can’t stand still. It must grow or perish”

What I love about this newsletter is that it forces me to publish every week. No matter what. It also forces me to reflect on the past week. If I’m not growing it’s painfully obvious.

Here’s to a week of growth ahead. Let’s get into the newsletter.

👫 When a Dating Dare Leads to Months of Soul Searching

“At 2 a.m., two blocks from Chinatown, Sarah ended our first date by telling me that my race might be an issue.”

This is a beautiful, heartfelt piece.

She gave a halfhearted laugh. “I’m sorry. It’s not that I don’t like Asian things. I love all Asian food, even stinky tofu. It’s just that I’ve never really been attracted to Asian men. I think it’s because there weren’t a lot of Asians in my small Texas town. All the Asian men I knew were either my friends’ dads or like nerdy brothers to me.”

Favorite thing I read this week. It even has a happy ending :)

Read the article here.

This chart is wild. It’s been shocking how ubiquitous dating apps have become since moving to SF. I wouldn’t be surprised if percentage of couples meeting online is >50% here.

One thing I think about a lot is whether dating apps are good for society. Dating and relationships are complicated. There are likely 2nd order / long tail effects of dating apps that we have yet to see or fully observe.

Do dating apps make us more risk averse? Do they make us worse at talking to strangers? What impact do they have on the divorce rate? What about our happiness?

I don’t have any answers. I suspect there are at least a few very large negatives that we will run into by fundamentally changing the way that humans find mating partners.

But I also know that whether we like it or not - dating apps are fully happening. They are unstoppable. And I think that’s almost certainly because they are doing more good than bad.

📕 The Best Books By Age (From 1-100)

This is a neat idea. Especially because so much of what makes a good book is timing. A great book at the wrong time might just not resonate or be interesting.

Ironically, I recently started reading Atlas Shrugged (before reading this list) which is recommended for age 24. Looks like I’m about a month early.

I’ve read a decent number of other books on the list and they are all excellent.

Read the article here.

🧠 The career arc of specialists and generalists

I really like the framework of the martini glass:

At least at some point in your career, it seems really important to go deep in a relatively narrow skill or combination of skills.

This is the easiest way to clearly differentiate your and build your “career moat”.

Although this is a great framework to structure your career growth - it skips over the hard part. How do you know when you’re ready to transition between phases? How to you avoid staying general too long, or going specialist too early?

These ideas are top of mind for me right now as I think about transitioning into a iOS/Android engineering role at Thumbtack. If you have any thoughts, I’d love to hear them!

🏀 Learn like an Athlete

Brilliant post by David Perell. Posts like this make me realize how early we still are. Knowledge work is still in its infancy.

Athletes train. Musicians train. Performers train. But knowledge workers don’t.

Knowledge workers should train like LeBron, and implement strict “learning plans.” To be sure, intellectual life is different from basketball. Success is harder to measure and the metrics for improvement aren’t quite as clear. Even then, there’s a lot to learn from the way top athletes train. They are clear in their objectives and deliberate in their pursuit of improvement.

Knowledge workers should imitate them.

Tyler Cowen posted a follow up covering How I Practice at what I do.

I appreciate how he also covers what he does not do.

My current list looks like:

  1. Meditate for at least 5 minutes every day.

  2. Read every day.

  3. Writing this newsletter

  4. Don’t bring my phone to work ~3 / 5 days per week

  5. Sleep + Exercise

I am far from perfect at all of these things. And there is likely so much more that I could be doing!

One of the most interesting parts of knowledge work is figuring out how to leverage technology to help us do our jobs better, and offload some of our knowledge to these tools. Building a 2nd Brain is probably the most interesting approach I’ve seen thus far.

🛍️ Shopify and the Power of Platforms

Amazon is where brands go to die. Shopify is where brands go to start building their brand.

At first glance, Shopify isn’t an Amazon competitor at all: after all, there is nothing to buy on Shopify.com. And yet, there were 218 million people that bought products from Shopify without even knowing the company existed.

The difference is that Shopify is a platform: instead of interfacing with customers directly, 820,000 3rd-party merchants sit on top of Shopify and are responsible for acquiring all of those customers on their own.

Ben Thompson articulates the differences between a platform and an aggregator better than anyone else I’ve read.

Although a lot of successful tech businesses thus far have been aggregators rather than platforms, I’m increasingly bullish on the power of platforms.

Platforms enable individuals to build their own differentiated business. Aggregators commoditize supply (at least to some degree) which leads to a race to a bottom.

But because many times you don’t even know you are using a platform it can be difficult to capture the value you create.

In the context of Thumbtack, I find the platform v aggregator debate even more interesting. In the case of Thumbtack, many service providers are differentiated. Your wedding photographer or home contractor is absolutely not a commodity in the same way that your Uber driver is.

I can’t help but wonder if a more platform approach that enables small businesses to build their business on their own would actually be a better approach.

Building out good scheduling tools, ways for customers to review, and offering SEO services for the websites of some of these pros would be incredibly valuable and empowering.

If you know anyone that’s building something like this I would love to hear about it.

More to Check Out

“10x engineers”: Stereotypes and research

Friendships Run Along Subway Lines

Wage Stagnation: Much More Than You Wanted To Know


- Started reading Atlas Shrugged. This book is a classic and so controversial that I felt like I couldn’t not read it. I’ve been surprised by how approachable it is. It’s even a bit funny at times. Would I recommend it? You’ll have to wait and see. Who is John Galt ..?

- I watched Higher, a snowboarding movie ft Jeremy Jones. A funny aside is that Jeremy Jones summited (and shredded) Mt. Shasta just a few days before we were up there. The movie is great - especially if you’re already dreaming about the coming winter like me. It’s much more about the adventure than the actual snowboarding. Ironically the climax of the movie is when Jeremy finally summits a ridiculous 65 degree face in the Himalayas only to discover that the snow is absolutely terrible and it’s all he can do to get down.

- I will be back in New Hampshire for the 1st week in August! If you’re in the area I would love to see you 😊.

Thanks for reading. See you next week (#42 !!)

- Taylor

Tangential Tuesday #40

Sort by Controversial, Philosophy, Medicine, Gen-Z, The art of resting, Costco...

Hey team, I hope your week is off to a good start. I finished reading Better: A Surgeon's Notes on Performance this morning.

It’s a beautifully written book - and I would recommend it just for that. And though it mostly focuses on medicine, Gawande also articulated better than I could have why I write this newsletter:

“Most of all, by offering your reflections to an audience, even a small one, you make yourself part of a larger world. Put a few thoughts on a topic in just a newsletter, and you find yourself wondering nervously: Will people notice it? What will they think? Did I say something dumb? An audience is a community. The published word is a declaration of membership in that community and also a willingness to contribute something meaningful to it.

So choose your audience. Write something”

This resonated so strongly with me. I have no plans or ideas for how to grow this newsletter. Some weeks I am not entirely sure why I write it. Some weeks I am not particularly happy with the end result.

I often find embarrassing typos when I read my posts the next morning. But this newsletter forces me to hit publish every week, and for that I am grateful.

Regardless of your job, it’s easy to feel like you are just a cog in massive machine. Writing is one small way to combat this feeling:

“Writing lets you step back and think through a problem. Even the angriest rant forces the writer to achieve a degree of thoughtfulness”

It doesn’t have to be much. Just a few paragraphs. You don’t even have to publish it anywhere. Write something.

😮Sort By Controversial

This is a highly entertaining, dark story of tech dystopia.

“This starts in September 2017. I was working for a small online ad startup. You know the ads on Facebook and Twitter? We tell companies how to get them the most clicks. This startup – I won’t tell you the name – was going to add deep learning, because investors will throw money at anything that uses the words “deep learning”. We train a network to predict how many upvotes something will get on Reddit. Then we ask it how many likes different ads would get. Then we use whatever ad would get the most likes. This guy (who is not me) explains it better. Why Reddit? Because the upvotes and downvotes are simpler than all the different Facebook reacts, plus the subreddits allow demographic targeting, plus there’s an archive of 1.7 billion Reddit comments you can download for training data. We trained a network to predict upvotes of Reddit posts based on their titles.”

Read the article here.

Destroyer of worlds: The 8CHAN Story

Speaking of dark tech news… I’ve got another one for you.

This profile covers the creator of 8CHAN arguably the most dangerous sight on the internet today. After reading this article I had to briefly checkout the site myself.

I have to admit, it was pretty terrifying. This site has known links to a number of school shootings and well as white supremacy. The creator? born in 1994 in upstate New York when he was still a kid.

This paragraph in particular struck me regarding the immense power of the internet:

Because of the way it’s structured, chan culture has immense power to create memes: they spread from the site’s users via pseudonymous communities like Reddit out to Twitter and beyond into the mass cultural consciousness. The /pol/ boards on both 4chan and 8chan have become home to far-right politics. One now-infamous meme that featured Hillary Clinton next to a Star of David sign made its way from its original posting to 8chan’s /pol/ board via anonymous Twitter accounts to Trump’s Twitter feed in a matter of days.

Read the article here.

😎 ‘True Gen’: Generation Z and its implications for companies

It’s always fun thinking about generational differences. Of course, broad differences regarding an entire generation will never be 100% accurate, but there’s DEFINITELY huge trends and differences.

In the past, I think geographic/culture differences were more of a driving factor in your actions, world view, etc. With the rise of internet and acceleration of technology, these differences are shrinking - but generational differences are becoming more and more obvious.

A few broad takeaways re Gen Z:

  • They value individual expression and avoid labels.

  • They mobilize themselves for a variety of causes

  • They make decisions and relate to institutions in a highly analytical and pragmatic way.

I found it funny that the article as well as this NYT article both speak very positively about Gen-Z… I guess the internet was tired of all of those articles ripping on millennials for buying too much avocado toast 🥑. Such is life.

Overall though, my personal experience at Minds Matter lines up with these broad take aways. These kids are way less addicted to their phones than most millennials and much more analytical in their decision making than I was at that age 🤷‍♂️.

Read the article here.

🛌 The Art of Resting

This something I personally struggle with. My mind is always moving 100 times a minute. And the sad thing is this mind actually serves me well a lot of the time.

But eventually - especially living and working in a city like San Francisco, this will run you down.

Often times, you think you are “resting” by scrolling social media or watching YouTube. This is not a rest for your brain.

“Recognize TV, movies, video games, porn, etc. for what they are – artificial over-stimulation.

The human brain did not evolve to be able to handle the constant stimulation and variety that high-speed internet can provide.

The human brain gets “hacked” by the stimulation that high-speed internet and media provide – use them in limited quantities and use them primarily for productive purposes.

Remember, your brain is also a muscle – it needs to rest. If you constantly bombard it with stimulation, it will throttle itself to a lower intellectual level.”

Read the article here.

🧠 Why You Should Study Philosophy

Ryan Holiday is back again with another fantastic article.

“If you told someone you had discovered an operating system for being a good human being — how to solve the problems of life, how to manage our tempers, where to find meaning, and how to think about death — most people would perk up and lean in. Of course they would. Who isn’t interested in being a better person and living a better life? That’s what we’re all struggling to do, day in and day out, with this random quirk of existence we’ve been given.

If you told that same person that what you’d discovered had a name, and it was “philosophy,” all the excitement and possibility that perked them up initially would leave their body like air out of a balloon. They’d almost certainly turn back to whatever they were doing before you interrupted them. And who would blame them for this aversion? Almost anything is better than talking about philosophy.”

This is something I really want to devote more time to in the 2nd half of 2019. Reading philosophy means reading slower and thinking more. It means discussing books with your friends.

It’s doing the hard work to read books above your level. But the fact that we even have access to these books is pretty amazing!! Expect some of my ramblings on philosophy I’m struggling to understand in future newsletters 😃.

Read the article here.

More to check out

- Why America’s New Apartment Buildings All Look the same

- Goldilocks Zone of Personal Finance

- Paradox of Ambition

Quote of the week

“Any momentary triumph you think you have gained through argument is really a Pyrrhic victory: The resentment and ill will you stir up is stronger and lasts longer than any momentary change of opinion. It is much more powerful to get others to agree with you through your actions, without saying a word. Demonstrate, do not explicate” - Robert Greene, 48 Laws of Power


Thanks for reading.

- Taylor

Tangential Tuesday #39

Education, iPhone, Facebook, Libra, Load Management, Robo Real Estate Investing..

Hey 👋 - Welcome to July. Hard to believe we are half way through 2019.

This weekend something special happened. I met someone at a party, completely randomly, no mutual friends (that I know of) that had read this newsletter and was excited to talk to me about it! The internet is cool sometimes

I actually write this newsletter almost purely for myself, but it’s always nice to hear from readers in real life. Writing online is still so underrated!

☎️ The iPhone Is a Breakthrough Handheld Computer

“The iPhone’s most controversial feature, the omission of a physical keyboard in favor of a virtual keyboard on the screen, turned out in our tests to be a nonissue, despite our deep initial skepticism.”

“We have been testing the iPhone for two weeks, in multiple usage scenarios, in cities across the country. Our verdict is that, despite some flaws and feature omissions, the iPhone is, on balance, a beautiful and breakthrough handheld computer.”

This is a fun look back on the original iPhone - published in 2007. It’s absolutely insane how much the world has changed since then. When I think about that, it’s hard not to get excited for what humans will do in the next 12 years 😊🚀.

Read the article here.

🧠 A Model for the Future of Education

This article is full of ideas which I love - but I have learned to be cautious when it comes to criticizing education. Rome was not built in a day, and neither were K-12 public schooling systems.

There’s a lot to be critical of with the current system, but all things considered it’s pretty amazing how good public school systems are. I can also acknowledge that they are extremely variable in quality, but my High School experience was probably one of the most intense learning periods of my life.

With that disclaimer, I’m SO excited to see how we can make things better.

“An average of 7,200 students drop out of high school each day, totaling 1.3 million each year. This means only 69 percent of students who start high school finish four years later. And over 50 percent of these high school dropouts name boredom as the number one reason they left.”

“When I think about the skill that has served me best in life, it’s been my ability to present my ideas in the most compelling fashion possible, to get others onboard, and support birth and growth in an innovative direction. In my adult life, as an entrepreneur and a CEO, it’s been my ability to communicate clearly and tell compelling stories that has allowed me to create the future. I don’t think this lesson can start too early in life. So imagine a module, year after year, where our kids learn the art and practice of formulating and pitching their ideas. The best of oration and storytelling.”

Read the article here.

🤑 Facebook, Libra, and the Long Game

Hopefully you’ve been able to avoid the recent flurry of news coverage on Libra, a cryptocurrency backed by Facebook.

There’s been a ton of media outlets publishing hot takes on this announcement, and quite frankly most of them are very bad.

As usual, Ben Thompson from Stratechery publishes a rationale and well thought out article. I still think people are very correct to be skeptical of this project, but there’s a fine line.

Many people have been quick to dismiss the currency all together, but Facebook is not stupid. They have an absurd network advantage. I still think the probability of the project gaining significant traction is relatively low, but we’ll have to see what happens.

Read the article here.

⚖️ Load Management

“As NBA stars stand to make tens of millions playing and even more in big media markets, and as the seasons get longer, they and their management teams are growing more conscious of the idea of “load management,” such as limiting “back to back” games, having allocations for playing minutes per game, and so forth in an effort to preserve the body both for a longer post-season (to stay fresh) and for long-term career prospects.

Yes, I’m tying this back to the startup ecosystem.”

I like this short article a lot. It can definitely be tempting to sacrifice the long-term for the short-term at times. It also makes me slightly concerned that Elon Musk seems to have absolutely no concept of load management.

Should we be more concerned that one of the most incredible entrepreneurs and scientists of our generation appears to be working himself to death? I’m not sure..

💰How Discount Brokerages Make Money

This probably sounds like a super boring article - but hear me out. Have you wondered how companies like Robinhood, E*Trade, Charles Schwab actually make money?

This article explains the entire landscape in an easy to understand, jargon free way.

He even adds a little spice 🌶️:

“And then there’s Robinhood, which is a discount brokerage whose marketing and product decisions probably do not assist their users in achieving successful outcomes.”

Read the article here.

Meet the A.I. Landlord That’s Building a Single-Family-Home Empire

“Sean Dobson, Amherst’s CEO, is an imposing Texan data savant who dropped out of college to get into mortgage trading. A decade ago, he made a killing shorting shaky debt during the housing crash. Today he’s adding 1,000 homes a month to his empire with the help of artificial intelligence, using data modeling to make dozens of offers a day on potentially profitable houses.”

Read the article here.

More to check out

As always - thanks for reading! Happy 4th of July 🇺🇸

- Taylor

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