The Toughest CTO Decision in 2022

For an organization with more than a handful of development teams, the hardest decision in technology right now is to decide where the cutoff between your platform teams and your software teams should be. As with most things in the world today there are loud people making loud claims on both side of the debate but the real answer is somewhere in the middle.

In one camp there are those that are screaming “developers just want to code”. They recognize that every member of the product team is expensive and they don’t want them spending hours selecting and troubleshooting infrastructure that they aren’t expert in. They also recognize the efficiencies possible if the infrastructure team creates standards.

In the other camp there is a really solid argument for self-sufficient product teams. We have all seen software product teams that know more about what infrastructure they need than the infra team trying to work with them. This is how shadow IT starts. Creating true DevSecOps teams that are responsible for everything their app needs also allows the organization to more easily invest in (or divest of) individual product teams.

How much will I sound like a consultant trying to make a few bucks if I say, “the answer is somewhere in the middle and really needs to be determined on a case by case basis”? Let me try to reward you for reading this far by breaking down a few of the things worth considering as you make this decision:

  • Are the products that your software teams are creating infrastructure dependent (e.g. low latency, require GPUs, edge, etc…). In this case, lean toward creating product teams that build their own infrastructure. Avoid the temptation to create single workload platforms.
  • Public cloud (and a willingness to commit to one cloud instead of attempting to maintain the ability to deploy any workload to any cloud) is a short cut in this debate. They allow you to build platforms that product teams can leverage simply through IaC and GUIs that would be cost prohibitive to create on premise.
  • Consider the use of “paved roads”. Make it really easy for app teams to “just code” without taking away the ability to customize the infrastructure if required.
  • If you’re going to try to change your organization’s focus from one side of the continuum to the other, do NOT underestimate the cultural inertia.
  • The absolute worst thing you can do is to not make a decision on this. You’ll end up with platforms that are over specialized and dev teams that don’t know how to use them. You must pick where you want to land on this continuum and make sure both your dev and infra teams are funded and motivated accordingly.

Dev Teams are Blocking Infrastructure

I recently took the job within Kyndryl of helping to establish and expand our Application and Data Consulting Practice. Kyndryl is known as an infrastructure company, there’s no way around that and I got lots of questions about why anyone would want to run the software portion of a company so focused on infrastructure. The truth is, for the first time in decades, the developers need the help!

In considering whether to take the job, I recalled a moment a few years ago while I was still working for a big bank with thousands of developers. I had made the switch from working on the software development side of the house to running the implementation of this bank’s Kubernetes clusters. I distinctly remember a morning when a young engineer and his manager came in to my office with a question about a support ticket they had received. One of the application teams had entered a ticket for our monitoring team to install a performance monitoring agent on a particular container. They gave the container’s full name and included approval from their management team for us to log in to the container for the install.

The application team had the ability to modify their own docker file to install the agent. Further, the fact that the application team wanted to software installed meant they had missed that containers were immutable by design and the value of having their container image and dockerfile stored and versioned. I realized then that the tables had turned. For the first time since punch cards gave way to Cobol and Assembler, the infrastructure teams were not holding back the development teams.

Of course it’s not universally true. The most advanced dev teams at most companies are still constantly challenging the infrastructure and security teams (even the cloud providers themselves) to provide more tools and technologies faster. However, there are a lot of software development teams that are not ready to make use of the advanced infrastructure that’s available to them. There are several reasons for this:

  • The teams aren’t trained on and don’t understand how to use infrastructure as code, horizontal scaling, asynchronous communication, and so many other things that are required for them to unlock the power of the infrastructure they’ve been given.
  • They are working with workloads that are stuck on legacy infrastructure like the mainframe.
  • The code they are working with is too ingrained in legacy development models.
  • The data is too disorganized and not secure enough to move to the cloud.
  • ERP or COTS workloads won’t allow them to leverage more advanced infrastructure.

My new team in Kyndryl is focused on helping your development team overcome these challenges and unlock the value of the infrastructure now available to you.

Machine Learning Holiday Project Part III: Using the Model to Predict Games

In this post I’ll cover creating the actual machine learning model to predict bets and how it worked for the fist slate of games. If you haven’t read the background on this project, I’d point you back to my first post in this series where I described the point of the holiday project.

Creating the Model

The first step is made miraculously easy by AWS Sagemaker. I needed to run the data I described gathering and cleaning in the previous post through AWS Sagemaker’s AutoPilot. I took a beginner course in ML at the beginning of the holidays before embarking on this project, and I learned enough to know that it would take me a year to do the data transformation, model building/testing, and model tuning that AWS SageMaker can do in a couple hours. I simply pointed at the problem and let AWS try 100 different models for each of the four questions (should I make an Over Bet? Under Bet? Bet on the Home Team? and Bet on the Away Team?) with data from all of the games from this season.

The winner in all four cases was an XGBoost algorithm. I’ve included both the model details and the metrics I got back above. As you can see, the F1 score for the classification got to .994. In a model designed to measure something so luck intensive, this is an obscenely high score. I think it can be explained by the fact that I had to duplicate some of the data since I didn’t have enough data to meet SageMaker’s minimums. The model almost certainly over tuned itself to criteria that aren’t actually as predictive as you’d think. If it manages to pick 99.4% of the games, I’ll be retired soon.

Deploying and Running the Model

Based on the lack of online literature on how to actually deploy/use models in SageMaker, you’d think it would be the easiest part. I did NOT find it to be easy. It’s the kind of thing that once you’ve done it a few times, I’m sure it becomes simple. However, for me, on my first time creating an AI it was anything but.

The main problem I ran in to was on deploying a model I could actually use later. I knew from the beginning that I was only going to want to use the model periodically and so I wanted to deploy it in a way where it could run cheaply. When I discovered that “Serverless Endpoints” were available I was excited! Imagine if I could deploy my model in such a way that I’d only be charged to use it the 15 times per week I actually need it without spinning up and shutting down instances! I looked at the picture above labeled “Details on the Model” and noticed that it had three different containers to be provisioned. I picked the middle one since it’s input/output was CSV and created a serverless endpoint. For under bets and home games this gave me gibberish results. Instead of picking 1 or 0 (bet or don’t) the model returned decimals. The other two models didn’t work at all. I tried recreating the models, redeploying the models, looking for information on how to interpret results. All of this assumed I was messing something up somewhere along the way. What I finally realized is that the three containers that made up the model weren’t “options” but all needed to work in concert. I gave up and decided to just rack up a high AWS bill and deploy the models from the “Deploy Model” button in the SageMaker AutoPilot results. This finally worked. If you’re curious, I kept my code for deploying a serverless model… I still think it’s an awesome feature.

Another few hours wrestling with formatting the input data correctly (all the same data I collected for the training data needed to be found for the games I wanted to predict). You can find my code for formatting this data on my git repo. While the code is written in a Jupyter Notebook, you’ll notice I’m using the AWS parameter store to retrieve my login for my score provider, the notebook has been written to only predict games that start in the next 30 minutes, and the playbook actually adds the bets directly to my database. This was all done because I am going to be turning this in to a Lambda function later in the week so that the BOOK-E can play in the league without any human intervention. More on this in another blog post.

I did get a few games where I got conflicting results. For example, places where I should place both a bet on the home team and on the away team. Whenever this happened, I just chose not to make a bet (you can see this in the python code). I only got the model running just before the 1pm games, so I could only make one prediction (on the Titans). In the 4pm games I had the algorithm running and WALL-E’s picks looked like this:


How Did BOOK-E Do?

Actually pretty good. Overall he was 6-2. There’s an almost 15% chance that a coin flip would have been that good in only 8 games though. You’ll just have to let me keep you posted.

Machine Learning Holiday Project Part II: Loading the Data

If you’ve done any reading on AI/ML you’ve probably heard someone say that the real challenge is collecting and organizing the data. That discussion is usually about finding good data, but I can tell you that it’s also a bit tricky to get data that you have access to organized enough for ML algorithms to run. This is especially true when you’re learning Python and Panda for the first time. Since this is just a learning experience for me, I cut myself off at about 10 hours of data gathering and sorting.

The big decision I had to make before creating the data is what should I make the “target” value. I could have either taken a direct path and asked the model to predict whether we should make a particular bet or I could take an indirect path and ask the model to predict what the score in the game would be and then derive whether the bet would be smart. I chose to take a direct path. I will explain this further below, but I have some data that relates to the actual bets and not the game. For example, I have data on how many people from my league have made a particular bet.

Another problem/issue with my data was that in order to create this “MVP” I used only 2021 data (data for previous seasons is harder for me to obtain since I delete most of the data out of LTHOI at the end of the season). This means that through week 16 I only have 208 data points. The SageMaker AutoPilot requires 500 data points. In order to solve this, I logged each game that I had three times. While this trick will let me process the data, it will make things like which two teams are playing a little bit too predictive.

As I am writing this the AI models are currently running, so I have no idea whether any of these have proven useful. Here are the data points I’ve given the model, how I gathered them, and what I’m hoping to get from them. When the model is done running, I should be able to add information about how actually predictive it is. I have also posted the Jupyter notebook that I used to gather the data to my git repo. In the notes below I tell you where in the code I gathered the data. At the bottom you can see the graph that AWS provides of how each field impacted the inferences both for over bets and bets on the home team.

  • The teams that are playing in the game came with my base data. When you watch shows about gambling you’ll always here statistics like, “The Steelers have never failed to cover when more than 5 point underdogs.” I am highly skeptical that individual teams help predict outcomes of games independent of their statistics. However, with the duplicative data I expect this to end up being a key indicator.
    • Source: This comes with the base data about the games from
    • Section of Jupyter Playbook: 3, 4, 5
    • Actual Impact: Because
  • Which team is the home team. Since I have the data in front of me, I can tell you that on average home teams win by 1.2 points this season. I assume that will play in to the model in some way. I could also see with the previous data point that certain home teams have a bigger advantage than others.
    • Source: This comes with the base data about the games from There is also a field that contains information about whether the home team is actually playing at their home field. For example when the NFL played a game in London. Technically there was a “home” team, but the venue did not have allegiance to the home team.
    • Section of Jupyter Playbook: 3, 4, 5
    • Actual Impact:
  • The line and over/under line that I used in These are produced by the oddsmakers and are designed to make the game 50/50. The line is in terms of the home team, for example if the home team is favored by 8 points I will have an 8, if they are 8 point underdogs I will have a negative 8. The lines continue to shift over time, but in order to make less confusing, I freeze the lines at midnight the night before the game. I doubt this will have much impact on the outcome, but I could imagine that sometimes bookmakers have tendencies that could be exploited.
    • Source: This is retrieved from the database of my LTHOI game. I used the boto3 SDK to access that database and pull the information.
    • Section of the Jupyter Playbook: 5
    • Actual Impact:
  • The average points scored and points against for each team. I calculate this by cycling through each team’s previous games and adding them up. There might have been some fancy data science way to get these together by combining spreadsheets, but I’m still more of a developer than a data scientist!
    • Source: This data was pulled from the statistics API.
    • Section of the Jupyter Playbook: 6
    • Actual Impact:
  • The number of people in my league who made each type of bet (over, under, home team, away team). I am thinking there may be something interesting here in the wisdom of crowds. Also, if there is news or injuries that the model doesn’t capture this will capture part of it.
    • Source: This data is available from the LTHOI table on bets. Unfortunately, I use a dynamodb and a very flat database so there’s a lot of expensive querying in here. If I keep using this AI model, I may have to add an index that will allow me to query this more cheaply.
    • Section of the Jupyter Playbook: 7
    • Actual Impact:
  • The final line for the game at kickoff. Since freezes the line at midnight before the game starts, there are sometimes factors that cause the line to move significantly (a player is injured or sentiment shifts). Some of the people in my league like to focus on this and others like to ignore it. We’ll let the artificial intelligence decide whether it is important.
    • Source: This data is available from the ODDS feed of mysportsfeeds.
    • Section of the Jupyter Playbook: 8

After creating this data, I used a separate Jupyter notebook to create the actual training data. It’s not as exciting as choosing which data to use, but you can find it on my github here. I decided to make the AI have four separate models that will make a binary choice on each bet. My intention is then to interpret the results and only place a bet if the models agree.

Machine Learning Holiday Project Part I: Overview

Why do a Big Data Project over the Holiday?

In 2021 the machine learning market was a little over $15B. That is projected to increase 10x between now and 2028. It’s the fastest growing area of technology (think mobile 10 years ago) and therefor it is top of mind for my clients. In addition, the sophisticated (read as expensive) hardware, software, and staff required to do on-premise, original Machine Learning is cost prohibitive for many current companies. I believe that, increasingly, “access to the hardware and off-the-shelf software that are provided by the hyperscalers” will become one of the primary reasons clients begin or accelerate their cloud journey. Right alongside “closing a datacenter” or “decreasing time-to-market” or “increasing availability.”

I’m certainly not new to creating cloud environments to support machine learning. I have created several kubernetes clusters and cloud environments across multiple clients with the explicit goal of supporting their AI/ML or Big Data efforts. In spite of that, I had little knowledge of what actually happened in those environments. With that in mind, I decided to embark on building an AI based “player” for the fantasy/gambling app that I already use to keep my hands-on skills sharp.

Introducing Book-E the robot gambler.

As many of you know, I currently run an “app” that lets my friends and I keep score on our football predictions. It’s described reasonably well on the homepage ( The TLDR version is that it allows players to chose wagers that should have even odds (they are coin flips) and then forces each of the other players in the game to take a portion of the other side of the wager. So, our AI/ML “player” in the game will have to pick which over/under and spread position bets they want to make each week. In order to have some fun with this, will call our AI/ML player “Book-E”

Book-E (assuming I can finish the project) will do a few things:

  1. Keep an up-to-date data set of all of the relevant football games and the data about them.
  2. Use machine learning to create a “model” of what kinds of bets will win.
  3. Evaluate each game just before betting closes (to have the best data) and pick which bets (if any) to make.

What tools/training am I going to use?

I’m going to have a lot to learn to complete this project! I will need to gather the data, to process the data in to data set(s) that can be used for machine learning, to create and then serve a machine learning model, and (finally) to integrate that model with my current game so that we have a new “player”.

Given my focus in 2021/2022 on AWS, I’m planning to focus on AWS technologies. I plan to leverage all of the AI technology in SageMaker for capturing the data and creating/serving the machine learning model. Also, since my application is AWS based (a set of lambdas, dynamodb tables, SQS queues, and an API Gateway), I will be adding a few lambdas and cloudwatch triggers to make the AI Player actually place “bets” and update models without the need for human intervention.

For the aggregating of the data, I am going to be using Python and Jupyter Notebooks as my workspace. Since I’m planning to be very AWS dependent I’m going to use the AWS Sagemaker Studio as my IDE. The data will come from existing tables in my application (which I will access using the AWS SDK known as boto3) and from the company I use to provide my scores/data for the game (which I will access through the Python wrapper they provide).

For creating and serving the actual machine learning model, I plan to use AWS SageMaker. Specifically, I’m really excited about the AWS Autopilot functionality which will select the best machine learning model for me without me having to be a data scientist.

This is going to require some training! At the onset of this project, I do not know much about AWS Sagemaker, AWS Sagemaker Studio, Python, the AWS SDK for Python, Jupyter notebooks, or machine learning! I identified the following Udemy courses that I plan to go through:

  • AWS SageMaker Practical for Beginners | Build 6 Projects – This is my primary course. It does a great job introducing the concepts of machine learning, the different types of models, and the ways to evaluate models. Even better, it does this using AWS Sagemaker and Sagemaker Studio as the tools.
  • AWS – Mastering Boto3 & Lambda Functions Using Python – This course was a great way to get started with both Python in general and with Boto3 (which is the AWS SDK for Python). If you’re a bit of an idiot (like me) and jumping in to this project without background in Python, let me HIGHLY recommend chapter 5 which covers a lot of what you need to know about Python generally in 58m. This would probably only be a sufficient overview if you have a decent amount of programming experience.
  • Data Manipulation in Python: A Pandas Crash Course – This course was great for an introduction to Pandas (a library in Python that’s useful for data manipulation/review) and Jupyter notebooks. While these are both touched on in the first course I mentioned above, if you’re going to actually do some of your own coding, you’ll need a more in-depth review.

Clever Idea: Serverless, Cloud Native CI/CD

If you’ve met me for more than a few minutes you’ve heard me talk about my passion project, Leave the House Out of It ( If you’ve really paid attention to my blog posts you’ve caught that a couple years ago I rearchitected the app to move to an event-based, serverless architecture on AWS. After a year of not doing very much with the project I’ve had the itch to make some upgrades (more on this next year). Before I did, I wanted to upgrade the CI/CD pipeline I use to manage the code.

While I had moved away from containers/EKS, I did keep the containerized Jenkins that had been deployed alongside my code on the EKS cluster. I got an EC2 server, installed docker, and deployed the image there. Unfortunately, on an EC2 server Jenkins quickly became both disproportionately expensive and pretty slow. The cost was due to the inefficiency of running a Jenkins server for an app you deploy infrequently. In fact, because the app was all serverless and low volume, I was actually paying more for my Jenkins server then for all of the rest of my AWS charges combined. In spite of the cost, the performance was pretty terrible. Jenkins lost access to deploy agents across my cluster and instead churned away on an under powered EC2 server. This caused larger runs of the pipeline to take upwards of 9 minutes.

Over the last few weeks, I’ve taken the final step to the AWS native world and adopted CodeBuild, CodeDeploy, and CodePipeline to replace my Jenkins CI/CD pipeline. My application has 5 Cloud Formation stacks (5 separate Lambda functions along with associated API gateways and DynamoDB databases) and an S3 bucket and CloudFront implementation that hosts the Angular UI. I ended up with 6 separate CodeBuild projects, one to build and unit test each of the lambdas and one to build the UI. The one that builds the UI I took a shortcut and simply used the build service to also deploy. For the 5 lambdas, I wrapped them in a CodePipeline along with AWS CF Deploy jobs for each.

The only tricky part I found was that I did not want to refactor my lambdas in to an “Application” so I could not use AWS CodeDeploy out of the box. That made it difficult to use the artifacts from AWS CodeBuild. The artifacts are stored as zip files meaning I can’t directly reference them from the CloudFormation for Lambda which is expecting a direct address of where it can find the .jar file (I wrote the Lambdas in Java). I got around this by having two separate levels of “deploy”. In the first one, I use an S3 “action provider” to unzip the build artifact and drop it in an S3 bucket that I can reference from the CloudFormation. The resulting code pipeline looks like this:

The results are compelling on several fronts:

  1. I was able to shutdown the EC2 instance and all the associated networking and storage services. It should save me a total of ~$50. It looks like on normal months I’ll be in the free tier for all of the Code* tools. So it will literally be $50/month right in my pocket. I expect all but the biggest software development shops are going to better with this model than with dedicated compute for CI/CD.
  2. In my case, I also sped up the process considerably. I had been running full build and deploys in around 9 minutes. This was due to the fact that I was using one underpowered server. AWS CodeBuild, is running 5 2 CPU machines for build and running my deploys concurrently. That has dropped my deploy time to about 1.5 minutes. (note: In fairness to Jenkins, I could have further optimized Jenkins to use agents to deploy the AWS stacks in parallel… I just hadn’t gotten around to it)
  3. The integration with AWS services is pretty nifty. I can add a job to deploy a particular stack with a couple of clicks instead of carefully copying and pasting long CLI commands.
  4. In addition, this native integration makes it easier to be secure. Instead of my Jenkins server needing to authenticate to my account from the CLI, I have a role for each build job and the deploy job that I can give granular permissions to.

There are very few negatives to this solution. It does marry you to AWS, but if you have well written code and a well documented deployment process it wouldn’t take you long to re-engineer it for Azure DevOps or back to Jenkins. It’s definitely going to be my way forward for future projects. Goodbye Groovy.

Book Review: Thank You for Being Late, by Thomas Friedman

The word “optimist” in the subtitle is very well earned here. Friedman’s book explains why/how someone can hope that the same technologies and macro-trends that are leading to hyper-nationalism, extreme divisiveness, and massive pollution might actually be harnessed for good. He tells that story with his typical great story telling and insightful anecdotes.

As usual I found a bunch of tidbits interesting and had a few realizations while reading the book that I’ll just list here:

  • One of the points that’s made over and over again that resonated with me is how fast technology is moving and how slow our institutions (particularly laws) are adapting to it. Especially since those technologies are contributing to the gridlock that’s keeping us from effectively regulating them (let alone adopting them for public purposes).
  • I found interesting that Friedman suggests his hometown in Wisconsin as a place well suited to adapt to the new world, mostly because of the strong community and the small size enabling a single suburb to really make it theirs. I understood the argument, but couldn’t help thinking that I’m glad I live in New York City… the combination of wealth and bright people I think will help push our leaders to adopt new advances more quickly in spite of our large size and less than community feel.
  • We’ve all heard Moore’s law, but I thought this explanation of just how fast computing power has grown to be compelling: “If a 1971 Volkswagen Beetle improved at the same rate as microchips did… In 2015 that Beetle could go 300,000 mph, get 2,000,000 mpg, and would cost $0.04.”
  • He makes a compelling argument for us entering the “cognitive” era of computing. While I still think this will be slower to take hold than people expect, it is fascinating that we have enough compute power now to just throw a bunch of data at the cloud and let the computers sort out if it means anything and what it means (as opposed to old school computing where you gave it an algorithm to make sense of the data with).
  • Since the book is optimitistic it makes the point that while artificial intelligence will do a lot of what we do for jobs today, that is likely to actually lead to more jobs. He brings up the example of automation in the textile industry. It actually caused MORE people to be employed making clothes because the price dropped so far that individuals owned more (far more) than one set of clothes.

Takeaways From 2021 State of DevOps

If you were trying to get a gist of the overall maturity level of an IT Ops and Infrastructure organization by asking only one question, I think you’d be hard pressed to beat the question, “How mature is your DevOps?”  I’d prefer that to “How do you use the cloud?” or “How fast can you provision a server?”.  The reason is that DevOps is the only industry buzz word that has a built-in “why”.  We get better at DevOps for a specific reason… to lower the friction for agile development teams.  There’s lots of reasons to go to cloud and a lot of reasons to automate things… some of them are good and some of them are bad, but if you’re always seeking to make dev teams more agile, you’re likely on the right track.

That’s why I’m always so enthusiastic to read the “State of DevOps” each year (a report commissioned by Puppet).  It helps you see where high-performing DevOps organizations (ones that can deploy to production regularly) are differentiating themselves from lower performers.  This can help prioritize your strategic goals and initiatives.

This year I had three key takeaways from the report:

  1. Automation and cloud are key to DevOps, but definitely not the only keys.  62% of companies stuck in “mid-evolution” on their DevOps Journey say that they have high levels of automation.  65% of those “mid-evolution” companies are on public cloud, but only 20% using it effectively.
  2. The DevOps Journey is something we’ll be focusing on for a while.  From 2018 to 2021 only 8% of companies graduated to high performing DevOps teams (going from 10% to 18% of all companies).
  3. Platform Teams are becoming key.  This is something that I’ve been working with my customers at Kyndryl on for the last couple years.  Platform teams are highly correlated not only with high performance on the devops scale, but also with employees feeling like they know their role.

Check out the report here and let me know if you think I missed something.

Book Review: Mindset by Carol Dweck

I can usually tell by 15 pages in to a self-help book whether it’s going to resonate with me; usually, it’s not going to. I can’t stand being told about how much I can get done in the morning if I start at 3am or that if I work 10x harder than everyone else it will pay off. These are obvious, hard work usually pays off (although if you think it automatically does, you should read Peak by Anders Ericson).

Dweck’s book is entirely different. It suggests that if you want to find fulfilling success, you should look at the world a little differently. You should stop asking yourself if you are successful and start asking what you can do to grow. I have to admit that 15 pages in to this book, I thought the idea was too simple to be useful. The more I read though, the more I liked the way it challenged me to think about life.

I’ve always been one to enjoy my successes with a little pat on the back (or more likely a celebration scotch). What I considered a success though was often what the rest of the world would view that way. For example, if my team at work won a new big project I would celebrate. If we had a month where we didn’t get a new project, I’d feel bad. It always felt a little cheap celebrating when the project win was just lucky and it was always tough to feel too bad when we made a great pitch to a customer that I knew would help them in the long-run, but that got scuttled when a key stakeholder retired. This book gave me a better way to look at these projects than pure outcome based success or failure.

Dweck would have us focus on “growing”. In the above example, the team clearly grew in our capability to identify and sell key projects by making that presentation (maybe we also learned how to identify clients we shouldn’t bother with). Dweck points out that it’s not that luck doesn’t exist; it’s just that you don’t want to let let your luckiest moments be the way you define yourself. This construct has given me a more consistent way to approach my days. Even on a bad luck day I start thinking about what I can learn from the situation and the best possible way I can move from here. If I’ve done my best and learned, I feel content and even more ready to take on the next day.

Book Review: Invent and Wander (collected Jeff Bezos)

Jeff Bezos built a company that’s worth about the same on the stock market ($1.67T) as the entire circulating supply of Pakistani Ruppees ($1.68T). That means you could BARELY trade every Pakistani Rupee in existence for all the stock in Amazon. I guess I’ll read some of his wisdom and see what he has to say.

I found the book pretty interesting. It’s not exactly a page turner and there are parts that are a little repetitive (the guy has clearly practiced telling his life story), but you can leaf through those parts quickly and be back in good material.

It starts with a republishing of all of his shareholder letters as CEO of Amazon (the last one you’ll have to find on the internet until they publish a new edition). They’re a fantastic read. It’s almost a retelling of the whole internet. From an optimistic Bezos reporting that Amazon had “established long-term relationships with many strategic partners, including America Online, Yahoo!, Excite, Netscape, GeoCities, AltaVista, @Home, and Prodigy.” in 1997. To a one word title of “Ouch” in 2001 after he saw some 90% of the value of Amazon wiped out. To explanations of how Amazon refuses to take a short-term perspective, even in a world where quarterly earnings are analyzed so heavily. To discussions of how, being a big company allows it to make big bets like the Fire Phone (dud) and AWS (clear winner) that it might not always win. To the mentality of “customer first” that Bezos uses to push employees because customer loyalty only lasts until your competition shows your customer something they never knew they wanted.

The remainder is a collection of Bezos’ speeches. This got repetitive with stories of how he admired his grandfather for being resourceful on a remote farm and sticking up for his mom when she was a pregnant high school. You should feel free to skip around, but don’t miss the speech on Blue Origin (his space company). The company is endeavoring to build the “infrastructure” for future generations to reinvent industries in space. He talks about the need to have big Lunar landers to send enough equipment to the moon so that the natural resources on the moon can start to be used for construction of more items in space (this makes sense since it’s much more efficient than trying to launch HEAVY things out of earth’s gravitational pull). It’s a fascinating way to choose to spend a personal fortune that is roughly 2,000,000 times larger than the average American’s.

Because of where I am professionally (with Kyndryl about to break off of IBM and provide me the opportunity to really grow the size, number of services, and the value we can provide the customers of my Cloud Advisory Service practice), I found the 2016 shareholder letter the most impactful. He talks about techniques for always staying in Day 1 because “Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it’s always day 1.” Resisting the urge to just get what you can from customers and instead keep innovating for customers, is the energy we’re going to need at Kyndryl.