Beginners Again

Tangential Tuesdays #86

It’s been a wild past few days between saying goodbye to San Francisco, packing all of the stuff I’ve accumulated in the past few years, and trying to drive a Uhaul around SF. There were a few hiccups, but… we’re here.

I’ve had a few moments of mild panic throughout the course of today. Up here, we are beginners. Sure, we’ve spent a few weekends up here - but we don’t know how most things work. Even just getting mail out here can be a process.

And that can be hard, or frustrating at times. I probably will not be at my peak work capacity for the next few weeks.

But being a beginner is fun, and I’m sure we will get a lot of hard earned lessons this winter.

I think what I’m most excited for is the way my mind will inevitably change with the change in the environment. The way my roommate put it - “What does this Friday night look like?” It definitely looks a lot different from a weekend in the city. At least until winter, it probably looks pretty quiet. We’re going to bed early, planning a bike or a hike for the next morning. We’re reading and *I hope* being present, enjoying this beautiful spot.

In reality, I actually have no idea what I’m talking about. Maybe it’s harder than I am imagining to break free from mindlessly scrolling the internet. Maybe life won’t slow down as much as I’m hoping 🤷‍♂️.

Regardless, I’m excited to see where the next few months will take me. If I end up hating it… well, I can just move back to SF in the spring. And if I love it? Who knows. At the very least, I will have some very clear memories of the next few months.

In unrelated news - I’m really excited to share the progress that I’ve made with my back over the last year! The top x-ray is from last October. The bottom is from last week. Red is actual, green is ideal. It’s not perfect, but holy shit. What a difference a year can make.

More important than what the x-ray shows, is how much better I feel. I’m a firm believer that the energy you put out into the world is the energy you get back. And since improving my posture, I truly feel like the energy I put out has changed significantly. And with it, my life has improved in basically every aspect.

For those of you that have never struggled with something like this - that might sound like an exaggeration, but at least for me, it is an understatement if anything.

I need to go to bed, some I’m gonna quickly jot down some random bullets that I forgot to talk about last week:

- I turned 25 in August…

- Started reading Life of the Party: Stories of a Perpetual Man-Child

- Wedding Vows Of The Girl Who Bullied You In High School

- Sleep tech 🛌

Goodnight, and have a great week

- Taylor

Breath in, Breath out

I’ve committed the deadly sin of newsletter writing… which is to say that I haven’t published a single newsletter over the past few months.

There are a number of reasons for this. The 1st and probably largest reason is that momentum is super real. Not just in a Physics, Newton’s 2nd law sort of way - but also in life and work. Momentum is at the core of the idea I was trying to get at here.

So I knew when I missed two weeks in a row, it would be brutally difficult to start again. I had built up a lot of momentum (84 newsletters worth to be exact)! And to be honest I’m not totally sure I’ll ever get that momentum fully back.

But explanations a side - here I am. If you’ve forgotten who I am or why you subscribed:

  1. Let me explain

  2. Feel free to unsubscribe 😊

This newsletter is intended to be a public journal for me where I learn in public and share a bit of my learnings with y’all along the way. It is not an insightful business analysis with original ideas or an aggregation of interesting links (do we really need more homework?). It is raw and it has typos and I will probably be wrong a lot 😅.

Yesterday I had quite possibly some of the best wine of my life (Nebbiolo Claré J.C for the curious) watching the sunset from Bernal heights. If you’re looking to do a boujee outdoor picnic in SF, look no further than Gemeni Bottle Co. Yes, I am partial to it b/c it is 0 blocks from my apartment - but is pretty excellent. Also these crackers.

I think this weekend also solidified for me that, despite many people leaving…. I still love SF. It’s hard for me to imagine that “this time is truly different” for SF or NYC.

Ironically I write this, 1 week before joining a movement that Bloomberg titled “The Bay Area’s wealthy tech bros are invading Lake Tahoe”.

By the time I write the next newsletter, I’ll be living with my friends Conor and Jeremy in this house in Truckee.

My 1st ever trip to Tahoe was part of a family reunion I was too young to remember. But my 2nd trip was an idyllic weekend in July when I was interning at Braintree. Since then, I’ve had a dream of one day living there. That dream intensified after renting a ski lease this past year and spending the 1st week of quarantine backcountry skiing before work.

But still, I had no real intention of making this dream a reality in the next ~30 years. When Jeremy approached me with the idea a few months ago, I both knew I had to do it while simultaneously never quite believed it was actually happen until I started packing up and selling all of my stuff this weekend.

And truth be told there are some days where I wish I could take it all back.

My roommate and I have a truly lovely apartment here. I feel like I have only recently found the friendships I spent my first year+ searching for. I have access to epic bike rides that I can do before work. And as I mentioned above, SF is beautiful (!!).

But I also know that this is a bit of a dramatic perspective of moving 4 hours away from SF for ~6 months. The way I think about it, I’m doing a semester abroad in an epic location. And unlike doing a semester in Italy - my friends can come visit for the weekend.

This doesn’t change the fact that relationships and people will change while I’m gone. But have you ever heard anyone say “I really wish I didn’t study abroad?” I haven’t…

🧠 Lil Thoughts

- Going to only do only backcountry / x-c skiing + splitboarding this winter. Goal: Hike 100k vert over the winter.

- There is something special about small communities that does not scale. I recently cold emailed Jordy Leiser, CEO of stella connect (company also playing in the customer service industry). He not only responded, but agreed to have fun with the team at Assembled. Why? We both went to Bucknell.

- Speaking of dope small communities, SF Backcountry skiers. A stranger gave me a pair of telemark skis WITH BINDINGS for free over labor day weekend. And they are like… really nice. Doing my best to pay that forward. Anyone in SF want a used splitboard? Stay tuned to watch me me make a fool of myself this winter.

- Speaking of Assembled, I can’t say too much, but things are going really well. We’re hiring two engineers if you know anyone that might be a fit 😃. Fo

- 📕 I’ve been reading Little History and From Impossible to Inevitable.

- 🤑 I think a lot of Silicon Valley has realized this already, but if you’re ambitious and looking for a job, consider joining Retool. It is one of the most exciting SaaS companies being built right now.

- My new home for the next few months.

- I recently made Smitten Kitchen’s (Cookbook only!) version of street cart chicken rice. And oh my lord it was so easy and so mind blowing. We paired is with some Sparkle Pony beer from Black Hammer Brewing (would recommend).

- I am extremely extremely late to the party, but I finally watched Parasite. It is as good as everyone told me it would be.

- Fun features that seem like they shouldn’t matter in business software, often matter a lot. Slack’s custom emoji feature is a classic example. Usefulness is still key, but fun features that spark joy can drive a lot of growth.

- I appreciate this chrome extension.

- I’ve kinda stopped reading most of the newsletters I get or really anything on the internet. I think it’s part of why I stopped writing this newsletter. I find the world so overwhelming this days, constantly trying to panic us. Between covid, wild fires, protests, political season and SPACs, it’s impossible to keep up. So I use work, food, books, and biking as my escapism. I honestly have no real idea how the world is doing with COVID-19 or with anything else for that matter. In some ways, I think this type of focus and ignorance is good…. but it’s sad that it can feel like a necessity for sanity these days.

- I haven’t gotten a haircut in ~7 months.

- Still rocking the Nokia 3310. It works 100% of the time, 25% of the time 🙃. My biggest problem right now is not being able to use venmo because I don’t have a working smartphone lol.

Quote of the week

“People always tell you, 'Be humble. Be humble.' When was the last time someone told you to be great?” - Kanye West

(I’m sorry, i had to. this thread was too good.)

See y’all in Tahoe 👋

- Taylor

Lassen 😍, the affluent zoom class, buying a car

Tangential Tuesdays #84

Hi 👋 - Feeling excited to dive into this week.

I spent the weekend backpacking in Lassen. It was pretty much a dream from start to finish. I owe so many good things in my life to taking trips like this. Nature == therapy.

Here’s our route if you’re curious! We had to pivot a bit from our original plan due to campsites closed because of bear sightings…. but with a plethora of alpine lakes to choose from it wasn’t too much of an issue.

Affluent Zoom Class

Talking about this magical trip with pretty pictures transitions well into my next point, inspired by this tweet:

This anecdotally rings true for me and many of my friends, and frankly is pretty disturbing.

There is an idea in business strategy that down turns typically make the strong, stronger, and the weak, weaker, even if the aggregate outcome is that everyone suffers in the short-term.

I worry that COVID-19 is doing this on the scale of not just businesses, but human beings. Over the past few months, I’ve heard friends say things like “I don’t want things to go back to ‘normal’”. And I get that. My life has in many ways improved since this craziness began ~4 months ago.

For people my age, this pandemic will almost certainly be remembered as the event of our generation. The problem however, is that it isn’t a shared experience the same way that 9/11 was for the prior generation.

In the same way that 9/11 brought the country together…. I worry that COVID-19 will divide us. The affluent zoom class vs everyone else.

I love the internet as a time capsule. Jessica Livingston (The coolest Bucknell alum the university somehow ignores!) interviewing Brian Chesky and Joe Gebbia in 2010.

Startup Wisdom from NPR’s Car Talk

Posit the question: Do two people who don’t know what they are talking about know more or less than one person who doesn’t know what he’s talking about? (Pardon the un-PC masculine pronoun, but I have found this to be, most predominately, a male phenomenon.)

So if ultimate reality, or learned ignorance, is achieved by two people, they have twice as much learned ignorance than one person, and Andy’s question is answered. Two people don’t know twice as much as one person doesn’t know. While your combined state of learned ignorance is often quite impressive, it is important to understand that to achieve ultimate reality a great deal of meditation and prayer is required


  • Assembled is hiring a Front-end engineer, as well as our first Support and Operations hire (!!). If you, or anyone you know might be a fit - email me. I am more excited about the business than ever.

  • I am officially in the market for a used car. Doesn’t have to be in the bay area. My only criteria are decent in snow and decent gas mileage. Let me know if you know someone selling a car or have any used car buying tips!

  • I swear every week someone pitches me on moving to a new place and every single time I fully descend down the rabbit hole of potentially leaving SF. This week? 2 Bed / 2 Bath in Big Sky

  • Nokia 3310 is working out well so far :)

1 month

Tangential Tuesdays #83

Hi 👋 - I hope you all had a wonderful 4th of July weekend.

Although the fireworks in SF were officially canceled this year, that didn’t stop our neighbors from setting off a massive pile of fireworks until about 1 am 🙃.

My celebrations included:

  • A 30-mile bike ride (Finally got around to doing Hawk Hill!) with a swim at ocean beach in the middle

1 month

I almost deleted this mini-post… but in the end, I decided to keep it. Generally, I think the newsletter is meant to be about talking about things that are not work. But this newsletter is also about my life. And work is a huge part of what is happening and is exciting in my life right now.

It’s been 1 month since joining assembled. Here’s what I’m trying to focus on.

1. be slow to criticize

When I started at Assembled, I immediately noticed a ton of things that were different from what I was used to. Here’s a quick list from the top of my head:

  1. We use a bootstrap theme from most of our CSS

  2. We don’t have a designer

  3. I am my own product manager and copywriter 😳

  4. I don’t have to write PHP 😃

  5. We don’t have a javascript auto formatter or ESLint

  6. We manually run raw SQL on our master database (regularly)

  7. We don’t have an easy way to search our logs (like Kibana)

  8. Our directory structure is different

  9. We have ~25 customers (rather than >25k customers)

Some of these things might not mean much to you all, but for me, it was like stepping into a whole new world. During my 1st month, I sometimes felt tempted to rush to provide value.

I found myself tempted to criticize. I found myself wanting to solve the problems I saw with the solutions I had seen at Thumbtack.

99% of the time, I think this is a mistake.

The first thing to note is that “rushing” to provide value is foolish. When you join a startup, you are entering into a multi-year (hopefully 🤞) relationship. The work that you complete in your first few months will be inconsequential to the work you’ll do in your 2nd and 3rd years at the company.

The 2nd point is that there’s a good chance that the company has a very good reason for not implementing the solution you are thinking about. Now, that reason at many startups might be “we just haven’t gotten around to it”. But don’t assume that’s the real reason! Rushing to provide value in your 1st month means not fully understanding the problem you’re trying to solve.

Lastly, even if you turn out to be right about both the problem and the solution, it is not worth the social capital you will sacrifice to push your solution forward. I cannot stress how important I think this point is.

In some ways, it is a bit counterintuitive: Assembled literally hired me for my expertise in solving these problems. Shouldn’t they want me to get started on that as soon as possible?

The answer is yes… but humans are still humans. For an outsider to come into a company and immediately start criticizing and changing things is jarring. Imagine if someone you didn’t know very well observed you doing your job for a few days and immediately started telling you everything that you were doing wrong. You probably wouldn’t listen.

Building trust takes time and hard work. I personally found it easy to forget how long it took to reach the level of trust I had at Thumbtack when I left.

Don’t rush, sometimes you have to slow down to speed up.

2. focus on relationships

For me, forming relationships with coworkers is probably the most important thing to focus on in the first few months at a new job.

This is something I didn’t appreciate enough over college, and also something that is unfortunately made much more difficult by remote work.

So far, I’ve met 3 out of the 8 people at assembled in person (1 of which was today, biking up twin peaks!)

So for that reason, I don’t have too much to say here….I am still figuring things out.

One thing I will say is that having a consistently positive attitude and being ridiculously optimistic at work goes a long way. Everyone else at the company been heads down working for the past few months/years.

They see all the problems that that company has. They will be tired at times. When you join a company - go out of your way to lift them up and bring fresh positivity. They will appreciate it and naturally want to spend more time with you 😃.

3. look for bright orange extension cords

New hires can see a bright orange extension cord in plain sight.

This is an idea Ryan has continuously pushed me on in the past month.

When I joined assembled I knew basically nothing about enterprise software, the problem we were trying to solve, how the product works, how are customers use us, etc.

This means that most of my ideas about how things should work, or what we should focus on will be wrong. But it also means that I will have wildly different ideas from everyone else that has been working at the company longer than me and knows more than me!

There is value in naïveté.

At the end of my first month, I took an hour to dump all of the thoughts and ideas that I had built up either in my brain or in my notes and then shared them with the company. It’s still unclear how much value this will provide to the rest of the company, but just going through the process of writing all of my naive thoughts down on paper has already proved valuable for myself.

4. immerse yourself

This applies less if you already have a lot of domain-specific expertise related to the company you are joining.

But as I’ve already mentioned - I had the opposite of that when I joined Assembled.

I’m still very much in the process of understanding the problem, the vocab, how to connect with our customers, and the whole world around customer support (it truly is a whole new world).

It’s hard to build something people if you don’t have a deep understanding of the problem you’re trying to solve.

Luckily, there is a ton of great content out there. Here’s what’s been recommended to me:

Customer support

Enterprise SaaS

5. take care of yourself

This one is simple and should be obvious. But that doesn’t mean it is easy. A ton of smart people neglect this.

I strongly believe taking really good care of yourself is one of the most important factors for being good at your job.

This will mean something different for everyone, but I think we all know intuitively when we’re doing this well.

Unequal Growth: The Zero-Sum Games You Don’t See

This is the 1 piece I *highly* recommend this week. It is quite long - so if you don’t want to actually read it, here is my incomplete summary.

In the first decade of the 2000s, the top 2 nations “got” 31% of all the Economic Growth. In the next decade, they doubled that share to 60% of Global Economic Growth.

Readers whose preferred economic mental models are Zero-Sum, will implicitly translate the verb “got” to “Captured”. Readers who default to Positive-Sum models will instead translate it to “Created”. They’d both be right.

Tech people love to talk about wealth as a positive-sum game. And to a certain extent, they are correct! But so are the negative-sum people. It depends on the period of time you are looking at.

GDP growth over the last 20 years is unevenly distributed. Even while the global GDP shrinks during certain periods, the growth of China and the U.S has largely continued.

GDP growth compounds. The more the U.S GDP grows compared to Japan or Germany, the bigger our advantage gets.

2015 marks the largest contraction in Global GDP that the World Bank has data for. If you live in the U.S, you probably did not know this. That’s because the U.S economy grew by $700B in 2015.

Read the article here. [Side note: Conrad has a ton of other great essays. I particularly love The Uncharity of College: The Big Business Nobody Understands]

Things I am feeling excited about

Make it glam

Tangential Tuesdays #82

My friend Abhi called me last week for the first time in a while. After we caught up on what we’ve been working on, he asked a great question:

“What else are you excited about?”

I paused.

“Honestly….I’m excited about human connection”

I think that kind of sums up how I’ve been feeling lately. My deep appreciation for connecting with other humans is unlikely to last too far past whenever life does go back to normal, but for now, I’m happy it is here.

Abhi followed up with the only logical response: “Did you…. get a girlfriend?” Unfortunately not… but I digress.

~make it glam~

There’s an idea that’s been rolling around in my head recently. I call it ~make it glam~

It’s the idea that even if you love your work, most work is boring and fairly mundane. To get really good at any craft, you have to do it over and over again.

I absolutely love being a software engineer, but honestly writing code can be boring. I have a feeling I’m not the only one who feels this way.

My solution? Find ways to glamorize it for myself. It starts with the strong belief that tasks are only as boring or exciting as I make them. It’s up to me to make my work feel exciting each day, even if the reality is a lot of mundane, detail-oriented work.

For me, this permeates my work in a number of ways. 1 is that I enjoy competing with myself and others by looking at Github stats to see who can rack up the most commits or lines of code this month.

To be clear, this is a pretty ridiculous thing to do. Lines of code and commits are loosely correlated to productivity (at best). For example, about 13k of my lines of code are actually from adding prettier to the project.

But we keep it light-hearted and it helps us get things done… so why not?

People say entrepreneurship has been glamorized. But why do we assume this is a bad thing? All jobs have their mundane parts, any job can be made to sound boring or exciting. So we should try to paint jobs as exciting if we believe that the world needs more of them.

Take this as permission to be a little more grandiose when talking, thinking, and writing about your work. You just might trick yourself into believing it.

Slowly…. and then suddenly

“There are decades where nothing happens, and there are weeks where decades happen.” — Vladimir Lenin

People in tech seem to love this quote, and I am no different 🙃.

There has been a ton happening in my life recently. The 1st is that my phone pretty much completely died this week. Those that know me well would probably agree that I don’t treat my phones very well, so this was not a huge surprise.

For the past few months, I’ve been slowly trying to retreat from the distraction the internet provides via my phone. I uninstalled google chrome + all social media.

But this retreat when from slow to sudden this week. When my phone died I immediately knew it was time to try a “dumb” phone. I ended up going with the Nokia 3310. Unfortunately, it’s not turning on at the moment though…. so I’ll be phoneless until I get that sorted out.

For me, it is a good reminder that your life often changes in instants, rather as a result of deliberate planning. Inspiration does have an expiration date.

There are inflection points: Booking a 1 way flight to Bangkok, Moving to SF, Texting someone you want to become friends with for the 1st time. I have no idea if this will be an inflection with my relationship with technology. But I find even the idea that it could be exciting.


Shoutout to Trevor Mckendrick for a great list of his favorite Star Slate Codex Essays.

I randomly chose this essay on class to read… and it did not disappoint.


  • We talk about economic class (how much money you make) and social class (how respectable you seem, education, what kind of family you come from) not enough.

  • Talking about class is taboo because we like to believe we’re a classless society. We talk about income instead and pretend it’s class.

  • 10% of people are in an underclass consisting of “generationally poor” people who may never have held jobs and who come from similarly poor families.

  • “65% of people are in the labor class. They work jobs where labor is seen as a commodity, ie there’s not as much sense of career capital or reputation. They base virtue and success around Hard Work. Its lower levels are minimum wage McJobs, its middle levels are assembly line work, and its higher levels are things like pilots, plumbers, and small business owners.”

  • 23.5% of people are in the gentry class. They fetishize education and career capital. They engage in all sorts of signaling games around “fair trade” and “organic” and what museums they go to. At the lower level they’re schoolteachers and starving artists, at the mid level they’re “professions” like engineering and law, and at the highest level they’re professors and scientists and entrepreneurs.

  • 1.5% of people are in the elite class. Although you can be borderline-elite by getting a job in finance and making a few million, the real elite are born into money and don’t work unless they want to. Occasionally they’ll sit on a board or found a philanthropic association or something.

This essay changed my world view in a very short period of time. I highly recommend.

My Update

  • Hard to believe it is almost July

  • Haven’t been reading 😞

  • Made some bread and hummus this weekend 😍

  • I got my first CSA pickup from Terra Firma Farm. So far - I absolutely love it. This week we got carrots, zuchinni, tomatoes, peacccchesssss 🍑, and potatoes.

  • Working….

- Taylor

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