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