New job, new adventures

Tangential Tuesdays #77

Hii! Writing this from the Oregon coast.

Last Thursday was my last day at Thumbtack.

I made the tough decision to leave Thumbtack and join Assembled. It’s a seed-stage startup. I start next week and will join as employee #9.

I’ve written in the past about why I think taking risks is admirable. And I’m happy to say that I actually took my own advice… even if that means that I might be out of a job in a year 🙃

I could not be more excited. I expect the next few weeks of onboarding could be a bit crazy. If the newsletter doesn’t go out - I assure you that I am alive and (hopefully) thriving. Aside from that, I plan to continue writing this short letter to you all each week.

I have learned a ton from writing this each week - and I suspect my learning will only need to accelerate while starting this new adventure.


Whenever major events occur in my life - I enjoy peeling back the layers of luck and serendipity that somehow led the universe to create this life-changing event.

For example, I got my job at Thumbtack through a combination of Airbnb and Bumble… but that’s a different story.

To understand how I ended up at Assembled, you have to go all the way back to July of 2017. I was interning in SF (not even going to go into the amount of luck that created that!) and of course, writing obnoxiously about my internship (yes i was that kid).

My friend, Zack (from high school!) reached out and told me I should try meeting Jordan Gonen.

So… I threw a dart and reached out in a slightly cringeworthy email.

My roommate Daniel (also absurdly talented) ended up coming along as well.

We met Jordan for dinner at Uber shortly after. Even back then - it was obvious he had what it takes to start a company.

At this point - you may be thinking: “why are we talking about Zack, Daniel, and Jordan? I thought this story was about Assembled”. Be patient, I will get there :).

Since then, Jordan and I have stayed in touch in various ways. He also runs a great newsletter.

Now - let’s fast-forward to ~2 months ago. I messaged Jordan and told him I was interested in joining an early-stage startup.

Here’s the convo:

First - let’s take a moment to acknowledge that Jordan literally sent me 1 and only 1 company. The probability of:

me interested in the company x company hiring x pass phone interview x pass onsite x still love the company x offer I’m excited about

is extremely low (!!!)

But… I’m getting ahead of myself.

Jordan recommended the company, but he doesn’t actually know anyone there. Luckily, my friend Edwin happened to know a few people at Assembled and was kind enough to make the intro.

And if that wasn’t ridiculous enough: I only know Edwin from a random DM I sent via twitter to Sar Haribhakti over a year ago. Sar was kind enough to respond and later invited me to drinks with Edwin and a few others. We became friends after a few dinners together and here we are 🤷‍♂️.


To summarize this weird and rambling story:

  • Throw a lot of darts 🎯

  • Silicon Valley is small

  • Luck is real

Special shoutout to my bois:

  • Subscribe to Jordan’s Newsletter and share his company: Compound, with anyone you know that works in tech.

  • Give Edwin a follow if you want to see some beautiful bread

  • Give Sar a follow on twitter for some snarky content

  • Read Zack’s writing here and checkout Dual School


Why Join a Startup?

The next logical question is “why would I do this?”

I’ve had to answer this question a lot in 1:1s at Thumbtack the past few weeks. And at times I’ve struggled to answer it well. Here is my best attempt at distilling it down.


I got interested in coding because of the ability it gave me to create new things.

Not because I was fascinated with how databases work or how you could optimally calculate the shortest path between two points using code.

Now, I’ve been a professional software engineer for ~2 years.

Somewhere along the way - I realized I was not actually getting better at building things. I was getting better at building on top of what other people had built before me.

I came to the conclusion that if I want to optimize for creating *new* things - it probably makes sense to join a small company.


Why Join Assembled?

*disclaimer*: my views are not those of my future employer.

The current product focuses on scheduling for customer support teams: How to meet the incoming demand for customer support, with the correct amount of supply in terms of staffing.

It’s a pragmatic solution to a very clear problem. I find this particularly refreshing in a world of AI hype and companies raising absurd amounts of money before launching a product.

More broadly, Assembled is built off the thesis that customer support can be a competitive advantage. Our goal is to build out the infrastructure to help teams scale a great customer support experience.

Moreover, I’m obsessed with this idea of a “boring” business.

The idea is stolen from Charlie Munger:

There’s a rule of fishing that’s a very good rule. The first rule of fishing is “fish where the fish are,” and the second rule of fishing is “don’t forget rule number one.” And in investing it’s the same thing.

Some places have lots of fish, and you don’t have to be that good a fisherman to do pretty well. Other places are so heavily fished that no matter how good a fisherman you are, you aren’t going to do very well. And in the world we’re living in now, an awful lot of places are in the second category.

Artificial intelligence is a big fishing hole…. but it’s also really crowded.

The logistics of customer support however? It’s that sleepy, mid-sized fishing hole that not too many people seem to be interested in.


On top of all this - there are the people I’ll be working with. I’ve spent a good amount of time getting to know the team over the past two months, and there is very little doubt in my mind that these are high integrity people that I want to work with. I can confidently say I will be joining as the dumbest person in the (zoom) room 😃.

As with all startups - there is a high chance of failure. That being said, I truly believe we are going to do really well over the next 10 years.


Remote Work Goes Mainstream

In other news, Thumbtack announced that employees will not be required in the office before July 2021 (!). Twitter, Facebook, Square, Shopify, and many more companies announced that they will allow employees to work remotely forever.

It cannot be overstated how large of a deal this is.

Many people in tech have designed their lives with the assumption that they will be living in a major tech hub until they either retire or decide to stop focusing on their careers.

This assumption is no longer true. It will take time for the world to rearrange itself based on the assumptions of a remote-first world…but it is happening.

And for some of my friends, it could happen extremely quickly. If I was still working at Thumbtack, there is a decent chance I would be trying to figure out how to sublease my apartment and convince my best friends to move to Idaho for a year with me.


Even after saying all of that… I remain bullish on San Francisco remaining as the best place to build your career in tech.

Zoom is not the same as in-person interaction. I think we can all agree that zoom happy hours don’t quite do it for us in the same way that dinner and drinks with friends do.

I’m all for remote work as a viable option. But personally? I’m excited to get back into the office as soon as I’m allowed.

We also tend to underestimate how difficult network effects are to disrupt. Silicon Valley started with NASA in 1957 and slowly built into what it is today. Networks are not built in a day. And they do not disappear in a pandemic.

Do I think this is a catalyst that will lead to the fall of Silicon Valley? Yes… but I think it will take 30+ years to fully play out.


How do you market yourself?

1. Sales is a lot like golf. You can make it so complicated as to be impossible or you can simply walk up and hit the ball. I've been leading and building sales orgs for almost 20 years and my advice is to walk up and hit the ball.

2. Sales is about people and it's about problem solving. It is not about solutions or technology or chemicals or lines of code or artichokes. It's about people and it's about solving problems.

Great thread.


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My Update


Thanks for reading!

- Taylor

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