The Unautomatablog
Unautomatable Audio
👨‍🏫💭👨‍💻Thoughts in Between Ed and Tech #1

👨‍🏫💭👨‍💻Thoughts in Between Ed and Tech #1

#Unautomatable consistency wk 10/26

Series Introduction!

This week my adventure as Head of Product at FourthBrain began. FourthBrain is a very interesting place to be leading product because the current products are actually cohort-based courses.

What does this mean? What implications does this have?

Well, consider that there is education and then there is “tech” (as folks in Silicon Valley would say). There are service businesses and there are software-as-a-service businesses. This week I started my journey off somewhere between ed and tech; somewhere between service and SaaS. While we’re definitely closer to ed and service today, the scalable path forward certainly leads to tech and SaaS.

There has never been a more exciting time to help build the future of education, and FourthBrain is creating the next level of machine learning education. To boot, the timing feels just right this week, as shortages for machine learning engineers abound.

Having made it to the intersection of digital products and online courses, I believe that there will be value in sharing my learning journey from here. My sense is that many more businesses like the one that we’re creating at FourthBrain will enter the marketplace in the coming years.

This new “Thoughts in Between Ed and Tech” series will become the focus of the Unautomatablog outside of special editions for the foreseeable future. Full disclosure, I totally stole like an artist from Matt’s Thoughts in Between. As an aside, I also kind of like that T-i-B-E-T spells Tibet, which when you google says “Tibet is the highest region on Earth.” Since this is the highest aim that I’ve been able to conceptualize for myself, and this next step in my #unautomatable learning journey has led me to FourthBrain, I feel some resonance there.

The point of chronicling my Head of Product and Courses adventures is to hopefully make some stupid and shareable mistakes so that an up-and-coming 21st-century education builder or two might get where they’re going a little faster, resulting in a little more value created for all of the teachers and learners out there.

In short, we’re building a true ed-tech business at FourthBrain, and it’s going to be a ride.

Come along!

Welcome to the Valley, Officially

As I sit on the final train to Palo Alto this morning, I’m struck by how unexpected fires have been started and put out this week, and how permanent fixes are under construction.

This is not just true with the actual Caltrain tracks (sending thoughts and prayers to the families of the injured), which I only learned about after showing up at the station this morning, but also from a business perspective. I feel that there is something symbolic about this train ride.

🛣️ Lesson #1: The journey that you think you’ll take is never quite the journey that you’ll end up taking.

Train → Bus connection to re-route around the accident to the next station.

At a micro level, when you think it will take 90 minutes, it will probably take 3 or 4 hours. That’s life.

This new journey of mine, where I’ll be helping a small but mighty team pioneer the next level of machine learning education and create meaningful, accessible, cutting-edge AI career pathways, looks from here like it will be an exciting, taxing, stressful, and wild ride ahead.


This is what I’ve been aiming at for the past two years. My aim has been brought into alignment with reality now, one uneasy step at a time.

So here I am, at the intersection of digital product and online courses, working with world-class Silicon Valley entrepreneurs, within an incredible ecosystem that (among many other things) is leading the digital revolution and creating business value at the intersection of AI and advanced manufacturing.

Right up my alley…

This is always where I’ve wanted to be, and it’s somehow fitting that I finally take the time to look around me. I just realized where the valley in Silicon Valley actually comes from. Everywhere you look, there are mountains in the distance.

⛰️ Lesson #2: There’s always another mountain to climb when you’re in the valley.

Without getting too existential about the yin-yang connection to TiBET that’s resonating within me right now, let’s dive into my Head of Product reflections on Week 1.

HoP Reflections on Week 1

The first thing that I’ll tell you is that week 1 was not boring. Not a bit.

I had this image in my mind that I’d get plenty of time to do deep product strategy work (my favorite). Yeah, that didn’t pan out; rather I came out of the frying pan and into the fire.

There are a lot of things to do the first few days in an early-stage startup that you wish you didn’t have to spend time on; paperwork things. But alas, employment verification, stock things, benefits things, and other general administrative things, these may not seem very important today, but they are.

It’s kind of like not doing your taxes. A few days or weeks pass; no problem. But that’s the wrong level of analysis.

🔭 Lesson #3: Be proactive on the things that you must be proactive on to set yourself up for success in the medium to long term.

This lesson applies to more than just paperwork; though. As our product is, in fact, cohort-based courses, we were running courses on Day 1. One of them was actually a new course, too, and on Monday we were having the second session. This was new, uncharted territory for everyone.

Minimum viable course status.

If you’ve ever been an educator, you know that the way you launch a course and set the tone and cadence for the learners is critical to the student experience.

There is nothing like diving in, getting your hands dirty and helping out with a new MVP on Day 1. And there’s also nothing quite like getting feedback from your team like “I’m so glad you’re here" and “great dedication on your first day.”

🥷 Lesson #4: So much for strategy; execution was everything on Day 1.

When I looked up after the first day, I realized that my calendar was filling up really quickly. There were interviews to do, classes to potentially help with or sit in on; regular weekly team meetings, daily tag ups, the 1:1 looking upward, and so on. This was without reaching out to any other person and adding complexity to my own schedule.

Of course, I need to start networking within FourthBrain and AI Fund more broadly, make sure that I take time to meet each member of the instructional staff and do proper intros, work with each member of the leadership team to determine near-term actionable areas of overlap, and ultimately, wrap all of this together in a plan that’s coherent for my first 90 days, hopefully by the end of the week!

After my new computer was set up, most of the admin docs were finished, the auto-scheduled items were on my calendar, and I had a handle - a first cut handle - on my inbox, it was Thursday.

And I had to travel on Friday down to Palo Alto.

Needless to say, I didn’t get as much done as I would’ve liked this week. But heading into the weekend I was reminded of the Naval Ravikant idea that "no one is going to value you more than you value yourself.”

I’ve taken the time to create space this weekend for my family, for reflection and celebration of simply making it to this point, for this Unautomatablog and the rest of my art. The most important things are the things you do every day and every week, and I needed to recalibrate over the past day to make sure that I’m in this game for the long haul, not on some fast-track to burnout.

I want to keep the vibe of meaningful engagement with my work going.

To do so, I’ll need to keep in mind my last lesson of the week:

🕳️ Lesson #5: Figuring out what not to do week-to-week will continue to be critically important to my medium to long-term success as a Head of Product.

I’ll be back with more Thoughts in Between Ed and Tech next week.

Until then!

The Unautomatablog
Unautomatable Audio
This is where I share my thoughts on stuff related to Unautomatability in the 21st century.
I'm currently reading my Unautomatablogs ( in my own voice. I'm a huge fan of audiobooks, and nothing is better than hearing them from the author!