AS Thoughts + Links

Small experiment. Mostly covering investing, IT infrastructure, and business models.
About Me

March 22nd, 2020
"I have personally found that the healthiest relationship between a board director and the CEO is one that is peer-like"
"To some extent, yes, but it’s actually the board’s job to encourage and allow the company to think long-term."
"Peter will almost always leave the ultimate decisions to the CEO he’s working with, but he has a way of using compelling examples from the many successful companies he has been involved with as anecdotes to help steer the CEOs to the right decisions."
"One of the beauties of rich networks is that they often provide access to the person that is best suited to give the best advice to the entrepreneur."
"The master of the universe of networks is Reid Hoffman."
"Particularly with VC-rich boards, I have found that all-too-often we enjoy hearing ourselves talk perhaps a bit too much."
Andy Rachleff ー 1 or 2 insights per board meeting

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"What has changed though, is that the community is not as involved as it used to be in the actual coding of the software projects."
"By the time the open source software gets to production it is rarely, if ever, displaced."

March 21st, 2020
March 20th, 2020

Joe Weisenthal thought experiment on short selling and business model disruption ー Matt Levine

"I suspect we see the same sort of dynamic with information on social media in particular; there is very little motivation to create misinformation about topics that very few people are talking about, while there is a lot of motivation — money, mischief, partisan advantage, panic — to create misinformation about very popular topics."

March 19th, 2020

"I've fired myself five times at Zapier: from my original role as a frontend engineer, from my role running our early platform, as a design manager, as a product manager, and most recently as Chief Product Officer."

March 17th, 2020
March 16th, 2020

March 15th, 2020
The Leverage Cycle - John Geanakoplos
"The crash always involves the same three elements. First is scary bad news that 3 increases uncertainty, and so volatility of asset returns. This leads to tighter margins as lenders get more nervous. This in turn leads to falling prices and huge losses by the most optimistic, leveraged buyers. All three elements feed back on each other; the redistribution of wealth from optimists to pessimists further erodes prices, causing more losses for optimists, and steeper price declines, which rational lenders anticipate, leading then to demand more collateral, and so on"

Time stamped thoughts
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March 14th, 2020
Claims that they were first company with "three pillars of observability"
"The ended last quarter (30-Jun-2019) with 8,846 customers across 100+ countries."
DataDog is self-serve
Core offering is the infrastructure monitoring tool
42 paying over $1M ARR
"In the first 6 months of 2019, ~60% of Datadog’s increase in revenue was attributable to growth from existing customers."
"In 2019 Datadog signed an agreement with AWS where they are required to purchase at least $225M of cloud services from AWS through April of 2022."
"1) enterprise sales team focused on large business 2) high-velocity inside-sales team focused on new customers 3) a customer success team focused on customer onboarding and expansions in the current base and 4) a partner team that works with resellers, distributors and managed service providers."
up and coming APM tools: Instana, Lightstep
"Datadog got their start in infrastructure monitoring, has moved “up” the stack towards APM and “down” the stack towards logging, and is continuing to bolt on products that customers are paying for, as evidenced by their high dollar-based net retention rates and multi-product sales growth."

Olivier (DataDog) and Shardul (Index)
Good thoughts on organizational design

"Superset is an enterprise-ready analytics application for data exploration, data visualization, and dashboarding."

Lol → Have you ever tried to install/setup Superset? The chances of you completing this task fall somewhere between "Next to impossible" and "Not going to happen".

"Moreover, Mulesoft’s exploitation of open source is now complete, giving ownership to a group that takes from open source without giving back commensurately."

Guess who? Like a McDonald's All American

Apple is a software company
"revenue per active user is the core metric of any internet company."
iOS app store
Payments and financial services

March 13th, 2020
"The sad reality is, no one actually wants to read your runbook documentation."
When do you developers use Google Docs and when can those instances turn into products?

Armon is a beast

March 11th, 2020
It does feel as if from has been on the money recently. Lean into self-serve if you can and focus on product development / build mode for the next few months.

"In the people business, relationships still matter, and I'm glad that's the business we're in." ー Nick Chirls

👀"When it comes to managing money, three is better than one."

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March 10th, 2020
Consumer Internet companies are built with the technologies of enterprise IT companies. Enterprise IT companies can now be built with the principles and strategies of consumer companies.

Which businesses have been built off package registries or managers?
was an OG.
- package manager for Kubernetes
- plugins for Serverless framework

March 9th, 2020
Interesting sentiment:
"Certainly, the greatest diffusion of open source projects appears to be in settings where the end users are sophisticated, such as the Apache server installed by systems administrators. In these cases, users are apparently more willing to tolerate the lack of detailed documentation or easy-to-understand user interfaces in exchange for the cost savings and the possibility of modifying the source code themselves."

(~8:00 ー heads down, do the work)


“I have pointed out that any superior record which we might accomplish should not be expected to be evidenced by a relatively constant advantage in performance compared to the Average. Rather it is likely that if such an advantage is achieved, it will be through better-than-average performance in stable or declining markets and average, or perhaps even poorer-than-average performance in rising markets.” ー Warren Buffett, 1960

March 8th, 2020
What are some debates / questions to pay attention to in software and IT infrastructure?
Can companies building stand independently? Some devs just view this as a marketing thing, not a real piece of technology.
Are tools for local Kubernetes development too opinionated? Examples include , , , ...
continues to emerge in enterprise security. Have an exciting bet in this space.
Is there going to be a data replication and backup company built for event streaming architectures? Rubrik emerged because traditional vendors in the space couldn't scale across clusters.
is cool. Other applications?
Are people confusing observability and application monitoring messed up? Is the difference semantic or real?

Peter Fenton on open-core software (~20:00 onwards)

Key bindings eat MFST Office
Excel: ??
PowerPoint: ??
SharePoint: ??


"Yes. One of the theses behind my research is that at the moment we rely too much on servers and centralization. If you think about how the Internet was originally designed back in the day when it evolved from ARPANET, it was intended as a very resilient network where packets could be sent via several different routes, and they would still get to the destination. And if a nuclear bomb hit a particular American city, the rest of the network would still work because it would just route around the failed parts of the system. This was a Cold War design. And then we decided to put everything in the cloud, and now basically everything has to go via one of AWS’s datacenters, such as us-east-1 somewhere in Virginia. We’ve taken away this ideal of being able to decentrally use various different parts of the network, and we’ve put in these servers that everything relies on, and now it’s extremely centralized. So I’m interested in decentralization, in the sense of moving some of the power and control over data away from those servers and back to the end users."
Peter Levin from A16Z has similar thesis

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