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JACOBS

TABLE OF CONTENTS
2025.02.09-On-Overengineering
2025.02.02-On-Autocomplete
2025.01.26-On-The-Automated-Turkey-Problem
2025.01.19-On-Success-Metrics
2025.01.12-On-Being-the-Best
2025.01.05-On-2024
2024.12.29-On-Dragons-and-Lizards
2024.12.22-On-Being-a-Contrarian
2024.12.15-On-Sticky-Rules
2024.12.08-On-Scarcity-&-Abundance
2024.12.01-On-BirdDog
2024.11.24-On-Focus
2024.11.17-On-The-Curse-of-Dimensionality
2024.11.10-On-Skill-as-Efficiency
2024.11.03-On-Efficiency
2024.10.27-On-Binary-Goals
2024.10.20-On-Commitment
2024.10.13-On-Rules-Vs-Intuition
2024.10.06-On-Binding-Constraints
2024.09.29-On-Restrictive-Rules
2024.09.22-On-Conflicting-Ideas
2024.09.15-On-Vectors
2024.09.08-On-Perfection
2024.09.01-On-Signal-Density
2024.08.25-On-Yapping
2024.08.18-On-Wax-and-Feather-Assumptions
2024.08.11-On-Going-All-In
2024.08.04-On-Abstraction
2024.07.28-On-Naming-a-Company
2024.07.21-On-Coding-in-Tongues
2024.07.14-On-Sufficient-Precision
2024.07.07-On-Rewriting
2024.06.30-On-Hacker-Houses
2024.06.23-On-Knowledge-Graphs
2024.06.16-On-Authority-and-Responsibility
2024.06.09-On-Personal-Websites
2024.06.02-On-Reducing-Complexity
2024.05.26-On-Design-as-Information
2024.05.19-On-UI-UX
2024.05.12-On-Exponential-Learning
2024.05.05-On-School
2024.04.28-On-Product-Development
2024.04.21-On-Communication
2024.04.14-On-Money-Tree-Farming
2024.04.07-On-Capital-Allocation
2024.03.31-On-Optimization
2024.03.24-On-Habit-Trackers
2024.03.17-On-Push-Notifications
2024.03.10-On-Being-Yourself
2024.03.03-On-Biking
2024.02.25-On-Descoping-Uncertainty
2024.02.18-On-Surfing
2024.02.11-On-Risk-Takers
2024.02.04-On-San-Francisco
2024.01.28-On-Big-Numbers
2024.01.21-On-Envy
2024.01.14-On-Value-vs-Price
2024.01.07-On-Running
2023.12.31-On-Thriving-&-Proactivity
2023.12.24-On-Surviving-&-Reactivity
2023.12.17-On-Sacrifices
2023.12.10-On-Suffering
2023.12.03-On-Constraints
2023.11.26-On-Fear-Hope-&-Patience
2023.11.19-On-Being-Light
2023.11.12-On-Hard-work-vs-Entitlement
2023.11.05-On-Cognitive-Dissonance
2023.10.29-On-Poetry
2023.10.22-On-Gut-Instinct
2023.10.15-On-Optionality
2023.10.08-On-Walking
2023.10.01-On-Exceeding-Expectations
2023.09.24-On-Iterative-Hypothesis-Testing
2023.09.17-On-Knowledge-&-Understanding
2023.09.10-On-Selfishness
2023.09.03-On-Friendship
2023.08.27-On-Craftsmanship
2023.08.20-On-Discipline-&-Deep-Work
2023.08.13-On-Community-Building
2023.08.05-On-Decentralized-Bottom-Up-Leadership
2023.07.29-On-Frame-Breaks
2023.07.22-On-Shared-Struggle
2023.07.16-On-Self-Similarity
2023.07.05-On-Experts
2023.07.02-The-Beginning

WRITING

"if you have to wait for it to roar out of you, then wait patiently."

- Charles Bukowski

Writing is one of my oldest skills; I started when I was very young, and have not stopped since. 

Age 13-16 - My first recorded journal entry was at 13 | Continued journaling, on and off.

Ages 17-18 - Started writing a bit more poetry, influenced heavily by Charles Bukwoski | Shockingly, some of my rather lewd poetry was featured at a county wide youth arts type event | Self published my first poetry book .

Age 19 - Self published another poetry book | Self published a short story collection with a narrative woven through it | Wrote a novel in one month; after considerable edits, it was long listed for the DCI Novel Prize, although that’s not that big of a deal, I think that contest was discontinued.

Age 20 - Published the GameStop book I mention on the investing page | Self published an original poetry collection that was dynamically generated based on reader preferences | Also created a collection of public domain poems with some friend’s and I’s mixed in, was also going to publish it with the dynamic generation, but never did.

Age 21 - Started writing letters to our hedge fund investors, see investing.

Age 22 - Started a weekly personal blog | Letters to company Investors, unpublished. 

Age 23 - Coming up on one year anniversary of consecutive weekly blog publications  | Letters to investors, unpublished.

You can use the table of contents to the left or click here to check out my blog posts.

Last Updated 2024.06.10

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On Optionality

2023.10.15

Lindy Expectancy: 32 Weeks

I tried writing a note simplifying my decision making process, but there are still many variables there that I am trying to understand better myself; communicating it right now seems like a fool's errand.

Instead, this one is brief. I settled on sharing one decision making heuristic I rely on quite heavily: optionality.

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Not Lottery Tickets

Here, we think of options as things that have a bounded input and an unbounded output. You can do a thing and you won’t lose any more than your initial outlay to do that thing, but you stand to gain a whole lot more.

An option is what makes you antifragile and allows you to benefit from the positive side of uncertainty, without a corresponding serious harm from the negative side.

  Nassim Taleb

Don’t think of ‘options’ just in terms of financial options, though, you don’t even need to know what those are. Think of it more broadly in terms of having more literal options in a wider range of situations.

You never know what’s going to happen; possessing a greater number of (quite literal) options can often be beneficial, particularly if you’ve started to hone in on a similar range of likely outcomes. Then, you can begin to identify one or two decisions that greatly increase your wellbeing or success in most of those situations.



Caption: The magnitude of the worst part of this graph isn’t that bad compared to the magnitude of the best part.

Going to the Gym

When I was younger, I realized that going to the gym was a great bet.

You exercise, and, assuming good form, all you lost was your time and the cost of the gym membership.

However, being more fit could make you live longer, protect you from ailments that would otherwise be debilitating, and possibly even help you win a fight, or, more likely, outrun a fight. Moreover, at some point you start to enjoy working out, so that time “cost” starts to feel like additional benefit.



Caption: 15 yr old me valued his time, but he also intuitively knew that there was an asymmetry in weightlifting that the video games he was regretfully playing didn’t posses.

And, of course, when I was 15, I was convinced that going to the gym was the best way to get girls to talk to me.

Analysis Paralysis

Running a start up presents you with an infinite set of ways to allocate your (and others) time. You can spend your time doing, quite literally, anything. How do you make decisions given so many different possible choices?

Startups don’t starve. They drown.

  Eric Ries (another oft quoted phrase with no easily discernible definite source)

I’m still learning how to do this, let alone how to do it well. One principle I feel confident operating on, however, is contingent on a thought out bias towars optionality.

The principle is not about maximizing your number of options in all situations, not at all; that can lead to immobility and getting stuck dead in the water. Rather, it’s looking at the range of likely outcomes in the direction you’re headed and determining what actions you can take that will put you in the best position regardless of which of those outcomes happens.

Decision making with Uncertainty

With Ultima, we’ve explored a number of different use cases for the tech we’ve built; we took the journey of building a solution that we thought was cool, and now are tasked with retrofitting it as a marketable solution to a problem.

The technology is quite good at finding and presents information about publicly traded companies to the user in the form of a daily briefing delivered via email. Obvious uses of this are for traders & investors, and this is where I thought our first dollar would come from. Less obvious uses are for knowledge workers like consultants or marketers & salesmen who need to know much about their clients.

About a month go, I started manually editing the content that our software curated before we send it out everyday. Doing this, I realized that one of the highest impact things I could do was improve the quality of our content.

Chance favors the prepared mind.

  Louis Pasteur

Why? Because no matter who we ended up selling to 3 months from now, better, less redundant information would most likely be essential. In most outcomes, increasing the value of the content itself has a high return.

Sure enough, we got our first paying customer the other day–he’s in sales. That is not at all what I was betting on; still, the principle engineering task I’ve been working on translates to direct value add for this customer.

The Philosopher’s Stone

I was effectively wrong; I did not think that the person who paid us was going to be our first customer, nor would I have bet on it. Still, I was able to make a decision that accounted for that possibility relatively well.

That’s why Nassim Taleb calls optionality the Philosopher’s Stone; it’s an incredibly useful heuristic for hedging against the fact that you know so little.

If you “have optionality,” you don’t have much need for what is commonly called intelligence, knowledge, insight, skills, and these complicated things that take place in our brain cells.

  Nassim Taleb

All that’s to say I still haven’t thought of an outcome for which staying fit and healthy puts you in a worse position, so you can still catch me at the gym.

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Again, optionality isn’t a license to not make decisions; it’s a heuristic to help you make decisions when you don’t have perfect information, which is always.

What can you do today to put yourself in a better position, regardless of what tomorrow looks like?

Live Deeply,