Hey, I'm Jeff.
Maker-of-trouble, stirrer-of-pots. I'm the co-host of What the AI?! and I write about AI, technology, and policy.
Latest Posts
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Regulators Make Bad Product Designers
At long last EU regulators are going to do something about the horrific slate of cookie banners that have descended on the web due to poor EU regulations (that have done nothing to protect privacy, best I can tell).
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Models Aren't Defensible
There’s a lot of AI news this week — but much of it kept bringing me back to the reality that ultimately models aren’t going to be defensible. That’s not to say that aren’t incredibly valuable and hard to design. But while models may ultimately create a lot of value, I think it will be hard to rely on creating a model to capture that value?
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AI: Car, Bus, or Road?
The conversation around public AI is messy and often unproductive. Part of the problem is that we don’t have a clear framework for thinking about how to govern AI. We end up with vague calls for government to “do more,” without clarity on what “more” actually means or where it makes sense.
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The Path Forward for AI in Education
We don’t yet know the destination, but we do know the path forward. At least, we know how to start walking it.
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A Simple Mode for Google Docs
I’ve been a fan of Google Docs for years. The collaboration features are unmatched—being able to edit documents together, leave comments, and see changes in real time has fundamentally changed how I work with others. It’s one of those rare tools that genuinely makes teamwork easier and better.
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AI and Work: The Blurry Line Between Augmenting and Replacing Humans
Many people who discuss the future of work in a world of AI talk about using AI to “augment and not replace” humans. Indeed, it’s one of the core principles of the Stanford Human-Centered AI Institution (HAI): “AI should be designed to augment human capabilities, not replace them.”
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3 Levels of Business Metrics
I’ve had a lot of conversation about OKRs — and I’ve even written down my thoughts on the subject a few times. I’ve also spent countless hours debating what the right OKRs for a company or team are. As I’ve reflected on the struggle to capture the right OKRs, I realize there is really a significant tension between metrics that are measuring very different kinds of things.
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Arc Browser
As an avowed gadget geek, one thing I’ve enjoyed about moving on from my role at Upstart has been the freedom to install whatever tools I want on my laptop, without having to negotiate with IT and InfoSec folks (you guys know I love you, but it’s true…) . I know I could have done this earlier with a personal laptop, but who wants to manage multiple laptops?!?! So, I’ve been playing with some new toys recently and there is one I want to share — the Arc Browser. I spend most of my time on my computer in the browser, so I was excited to see someone come out with a truly fresh take on how it should work. Here are my favorite features:
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Don’t Underestimate Narrow AI
created by DALL·E 3 through ChatGPT interface.
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Writing to Think
I recently announced that I was stepping back from my full-time role at Upstart. It was sad for me to go, but I tend to be someone who looks forward and not backward — so I’ve been enjoying all the questions about what I’m going to do next. And the honest answer is, I don’t have any substantial plans right now.
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User Experience as a Moat
I have a habit of creating a photo book every year for our family — and also an individual one for any larger family trips we take. We just returned from a large family trip — and I finished the photo book for this trip in about 2 days. Most people will consider that a bit crazy (and it probably is). But I think there is also a lesson about product design that can be learned from my experience — one that will be applicable to the coming onslaught of AI companies.
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Book Review- A Promised Land
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Visions of a Brighter (Calendar) Tomorrow
Automated Calendar Tetris
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Running Docs
I’m not sure what the right term is for people like me, but there should be one. I tend to keep iterating through different productivity tools and methods constantly. Some of this I think is a healthy evolution as I learn new things and try to get better at managing myself and my tasks. And some of it is probably a bit unhealthy. I know there are others like me — who just have to try the latest tool / technique — I’m just not sure what they’re called.
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Faster (and better!) golf with fewer clubs
Almost a year ago, a friend of mine mentioned “speed golf” to me. For those not familiar, it is a version of the game played competitively where your overall score is your number of strokes plus your time in minutes. Speed golf players typically play with smaller bags and reduced sets of clubs — and often finish 18 holes in under an hour and a half.
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Better (simpler) golf stats
I’ve come to a hole-in-one (so far…)
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The Power of Re-Framing a Tough Question
One summer during college, I ended up working at a small startup. There are so many great stories from that experience, one of my favorites of which is when my Mom thought I had dropped out of college to work there (I hadn’t). But none of those stories are the subject of this post — this post is about my compensation.
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A Better Frame for the Google Anti-trust Case
I found the anti-trust case against Google extremely under-whelming. There have been plenty of detailed analyses done on the case and the merits, so I’m not going to do a deep dive on that here (I’m still partial to Ben Thompson’s analysis on Stratechery). However, I do want to make a comment about framing — because I see many observers using what I think is the wrong frame when discussing this issue.
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Don’t Fail — LEARN
I’m not the first person to say this, but I really hate the “fail fast” mantra. The whole concept of being okay with failure doesn’t make any sense to me. I don’t know anyone who thinks failure is a good thing or something to aim for. We are all looking to succeed.
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OKRs and the Rule of 3
Many companies (and individuals) in Silicon Valley leverage OKRs as an effective way to set goals for their companies and themselves. After being properly trained (or brainwashed) in the ways of OKRs at Google, I continue to use them in my work at Upstart and in my personal life.
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How Asking Basic Questions is a Superpower
I was having a conversation with a colleague recently and I gave them some advice that I thought might be useful more broadly — ask the dumb question. I honestly think this is one of the best superpowers you can have — and luckily it requires no skill except for a bit of confidence and a lack of ego.
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My Favorite (Current) Productivity Hack
These headphones are my favorite productivity hack at the moment. For some reason, when I put them on (with the right type of music) I am substantially more productive. This is true even when I’m working from and no one is going to interrupt me whether I have them on or not. There’s just something about blocking out the world in general that helps me really focus and just power through a long list of action items. I find this has been particularly helpful during the pandemic work-from-home environment as there is just more noise to block out.
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Input vs Output OKRs
I’ve written about OKRs before and I think they’re a great tool for individuals, teams, and companies to set clarify their important goals and focus on clear, specific metrics for success.
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I think of a task as anything I can complete in one sitting.
I think of a task as anything I can complete in one sitting. If it takes longer than that - it’s really a project. I typically think of projects as relatively defined sets of tasks. Say, creating a blog post for my company. It might take a draft, copy editing, review, and legal approval. Pretty well defined. An objective is usually more outcome oriented and less well defined. For instance, lose X pounds. Even though it’s clearly defined - the required actions to achieve the objective are not entirely clear.
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Collaborating vs Copyediting
As an EARLY user of GSuite’s collaboration suite, I’ve been a big fan of their ability to increase collaboration for a very long time. In particular, love the collaborative editing features of Google Docs. The ability to have multiple editors is a huge win for anyone working collaboratively on a document, presentation, or spreadsheet. I also think the comment feature is well through through and a huge value for teams (though why comments work so poorly on iPad, I still don’t understand).
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Become a Power User
Many people today spend an incredible amount of time using a variety of collaborative technologies. It seems that for many employees today, the core of their job is really communicating and collaborating with both internal and external partners. Whether that means email, Slack, Google Docs, Sharepoint, Zoom, Skype or some other tool, we all seem to spend a lot of time in the middle of technology-mediated collaboration.
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5 Considerations for Managing Credit Through a Crisis
We are living through unprecedented times and financial institutions are a critical piece to bringing stability to their customers’ lives. That being said, financial institutions still need to take prudent measures to ensure that they are managing risk. Upstart is quickly managing through many of the same challenges as we work with our bank partners, and I wanted to share 5 considerations I am thinking about for how to navigate this environment in the short term that will pay off, both for the company and for the borrowers we serve, in the long run.
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Double-Opt-In Intros
Many people have written about the concept of the double-opt-in introduction, so I’m not the first to this concept ( just google it) and you’ll find plenty). The basic idea is that both parties need to agree before an introduction is made. I think the benefits are pretty clear, and it’s really the only way I made introductions these days Usually, one party has inherently opted in since they asked for the introduction and that’s what I want to talk about in this post — the right email asking for the introduction.
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Practical Education
There is a lot of debate and consternation over the quality of the educational system in the United States. While we have a higher education system that is the envy of the world, we seem to struggle in the K-12 arena on a number of international comparison metrics.
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The Great Hack
I just watched the new Netflix documentary The Great Hack. It’s really a deep dive into the Cambridge Analytical scandal and how it impacted both the Brexit campaign and the 2016 Presidential election in the United States.
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Changing Things Up (Again)
I wrote a while ago about how I like to change the design of my desk on occasion, really just for the sake of changing things. The spice of changing things up just seems to help re- invigorate me from time to time.
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See One, Do One, Teach One
When my wife attended medical school, there was a simple mantra about learning that I thought was very powerful: “see one, do one, teach one.” To really understand how to perform a given procedure you must first see one done, then do one yourself, and finally, teach someone else to do one.
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Consolidation in the World
I recently saw this graph in the Economist describing the number of publicly- traded companies in the US. The chart surprised me some. I really didn’t have a preconceived notion of what trend to expect for the number of public companies, but I was surprised to see the relatively rapid decline.
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Book Review - Range
I recently finished Range — Why Generalists Triumph in a Specialized World. It was a fascinating exploration of whether or not deep and early specialization is a key driver of ultimate success. As is fairly evident in the article, the author concludes that in fact having a broader set of interests to explore early in life, early in a career, and over time can actually be key drivers to greater success and more innovative thinking. There were two reasons this book really resonated with me.
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Apollo 11
I have greatly enjoyed watching the various celebrations for the 50th anniversary of the Apollo 11 mission. I watched the recent Apollo 11 documentary with my family as well as seeing the traveling Apollo 11 show that was in Pasadena. My kids have found it somewhat interesting, but I have been mesmerized by the history of that accomplishment.
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My Bullet Journal Method
If you’ve read my previous posts, you might have noticed that I am a bit of a productivity nut. I have used more task management apps than any rational person would ever know exist. If you’ve heard of a task management app, it’s a virtual certainty that I’ve tried it out. I’m not sure if my consistent switching is due to a short attention span or real efforts at optimizing my workflow. Or maybe I just haven’t found a system that really works for me (yet…).
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Can Slack become the one communication tool to rule them all?
I was an early and vocal fan of Slack. I helped bring it into Upstart and have even set it up for a number of one-off use cases. I had high hopes that a new tool would give us a chance to fix some of the issues that have plagued email. We are now a few years in, and the results are decidedly mixed. I don’t blame Slack here, but I think we are all struggling to figure out how to manage our technology tools to be more productive — and avoid having them become non-stop distractions.
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Productive Procrastination
One of my favorite professors at Stanford was a philosophy professor named John Perry. I took several classes from Professor Perry and I loved that he viewed it as his role to challenge our thinking. After one particularly animated debate, I remember Professor Perry leaning over and telling me “I actually agree with you, but they don’t pay me to agree with you.”
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Iterating on Forecasts
I recently wrote about the issue of building models that cause us to focus on precision sometimes at the expense of accuracy. In building models to predict or forecast future outcomes, it’s important to focus on accuracy over precision — particularly when you first start making forecasts.
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Precision Inside of Accuracy
Many people use the words -precision- and -accuracy- more or less interchangeably. However, they do have specific and quite different meanings.
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Sphero RVR
I really believe that the best way to get kids to engage with engineering topics is to have fun, engaging projects for them to tackle. All theory and no play makes for a dull experience and glossed over eyes. It’s part of my belief that we should have more top-down learning, and less bottoms-up learning — especially in complex areas like hardware and software engineering.
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Changing things up
For some reason, about every 6 months I feel the need to change the way my desk is set up. Generally, this means I either add back my external monitor, keyboard, and mouse or I put them into the closet for another six months and have a much emptier desk setup. This week felt like time to put them away again and move back to the simpler setup. Here’s what my desk looks like now (thanks to my wonderful wife for giving me the bamboo to bring a little life to the room).
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Data Moats
I’d like to think that over the last 6.5 years at Upstart I’ve learned a little bit about machine learning. I’ve even built a very simple neural network that performed pitifully in a Kaggle competition. One thing I’ve heard repeatedly is that a mediocre algorithm with great data will beat a great algorithm with mediocre data. Of course, having great models and robust data is obviously the best options…
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My “Uniform”
A while ago I decided to simplify my work attire. I was probably inspired by some combination of articles on Steve Jobs and Mark Zuckerberg always wearing the same thing, discussion of decision fatigue, and general laziness. I decided that I would just adopt a navy polo and jeans or khakis as my typical work attire. It seemed like a decent, simple look and was something that I mostly already owned.
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HP Chromebook x2 — Great Device for Kids (and maybe adults too)
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2018 Reading Goal
Last year I set a goal of reading 50 books. It was pretty bold for me as I typically read many fewer books than that. However, I wanted to spend less time on the news and more time reading longer form content. I’m happy to say that I managed to read my 50 books in 2018. It was a great experience — and I read a lot of great books (you can check them out on my Good Reads account).
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Make the Audience Your Hero
I was recently watching a few presentations which reminded me of one of the key aspects of a good presentation: make the audience the hero of your story!
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Damn Right! Behind the Scenes with Berkshire Hathaway Billionaire Charlie
I just finished this biography of Charlie Munger. It’s bit outdated (originally published in 2000), but still a very interesting read. I increasingly find myself drawn to biographies and histories in my reading.
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Top Down Learning
I recently wanted to learn a little bit more about machine learning. Given how important ML is to our work at Upstart, I wanted to add to my conceptual knowledge with a little practical work. So, I set out to go through some of the coursework at Fast.ai. I enjoyed the coursework. I didn’t finish all of it, but I did manage to build a few simple machine learning models that helped me understand the underlying concepts much better. At least for me, doing some real hands-on work is crucial to developing a deeper understanding of any topic.
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Beautiful[AI] — Presentation software done right
This weekend my wife introduced me to Beautiful[AI], a new presentation tool she had used to build a recent talk she was giving. She mentioned how much she enjoyed it, so I had to take a look. It turns out, she’s right! (I already knew she’s much smarter than I am, so this didn’t surprise me). It is a wonderfully designed piece of software.
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Pixel3 First Impressions
When I left Google 6.5 years ago, I decided it was time to ditch Android and try an iPhone instead. I’ve been a massive fan of pretty much all my iPhone and iOS in general since then. Since our phones are our primary cameras now, I tend to upgrade frequently to have the best camera I can.
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Voting in CA — Direct Democracy
Over the weekend I sent in my mail-in ballot for the Election this week. (PSA: If you haven’t voted, make sure you vote on Tuesday!). I feel that voting is a critical responsibility for all citizens in our democracy. It’s not just a right or a privilege, but an obligation we all take on to become educated about critical issues and make our voice heard.
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The Law of Unintended Consequences
It’s not a law that’s taught in school — or really anywhere. Typically this law we can learn only through experience. However, it may be one of the most important and under-rated laws anyone can understand to succeed in life.
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My Favorite Way to Structure Presentations
In my line of work, I end up building a lot of presentations. While different venues and formats often call for different styles, there is one general format/structure that I find almost always works well for any type of presentation.
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Slick Integration - Slack + Google Drive
I’m constantly impressed with Slack’s execution, particularly around integrations. They are very good at executing the little things that really make for a delightful customer experience. One grat example of that is their integration with Google Drive.
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7 Minute Workout
When I posted a while ago about my Morning Routine, I was running pretty regularly on the treadmill. If I’m being honest, I have found that a struggle to maintain. Running is hard for me to get into first thing in the morning — and by the time I’m fully awake there often is not enough time left to fit in the run. There’s also the issue that I usually need to take a shower after running — and that eats up more time in the morning. While I do get up early enough to have the time — it’s hard to fit in things like the shower once my kids wake up and start occupying my time.
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Taking notes on paper
I see this advice a lot of places, but I really enjoy taking notes on paper. I know people point to research about how writing engages a different part of the brain and helps increase long-term retention. I feel like every day or two I read a post about that topic. That certainly seems reasonable to me, but I honestly haven’t read any of the research. I find taking notes on paper helpful for a few different reasons:
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Sharing Slides Between Decks
As someone in an external-facing role, I spend a decent amount of time in Keynote / PowerPoint / Google Slides building presentations. I give lots of presentations to external audiences and I often build custom presentations for each audience. Sort of.
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Reflections on Science and War
The
Enola Gay B29 that dropped an atomic bomb on Hiroshima, Japan. -
Slack Customer Service
Slack is a company that has always impressed me with how they handle customer service. They take a customer friendly approach to a number of areas that traditional enterprise software companies handle very poorly.
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Checklist Manifesto
I recently finished Atul Gawande’s book The Checklist Manifesto. It was a fascinating look into the adoption and success of checklists in a variety of industries from construction to aviation — and of some places where checklists aren’t used as widely as perhaps they should be (for instance, Gawande’s chosen profession of medicine).
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DC Capital Bikeshare
My wife and I recently spent a few days in Washington, DC. Nearly a decade ago we spent 3 years living in the DC, and it has become one of my favorite cities in the country. I always loved how open, green, and flat it is for a real metropolitan area. Living close to the office and downtown, we used to walk around the city a lot and I enjoyed how easy it was to get around without a car.
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The power of the pen
Stop buying cards and start writing them!
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Poor Design- An Example
Why you have to think about how people actually use your product
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My Travel Tech Stack
I’ve heard from a lot of people that they enjoyed my post iPad Pro: My Travel Computer. I thought it might be useful to break down what my travel tech stack looks like. I’ve been using this kit for a while, and it works remarkably well for me. I’m a big believer in travel that less is more — so this isn’t a huge list; but it works very well for me.
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Flying Drones with Google Assistant
I’m glad so many people enjoyed my post on Flying Drones with Code. A few people at Upstart enjoyed the post and asked me to come and present the drone coding experience at one of our lunch ‘n learn sessions in the office. This turned out to be a lot of fun (you can see a quick video of our final result here…). However, one of my colleagues said she was bringing her kids in to see the project — and that they already tried the basics but wanted to “learn from the pro.”
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Color Free — Moving to a Grayscale Homescreen
As I recently wrote, I have begun listening to more podcasts. On a recent episode of the Ezra Klein Show I heard guest Tristan Harris mention that he has his phone home screen in a grayscale mode. The basic theory is that the color in your phone is part of what draws you in and psychologically causes you to engage with the apps on your phone. There’s no question that our phones are well (and intentionally) designed to attract our attention — perhaps demand is a better word. I do find this overall “addiction” that we experience unhealthy, so I was interested in this idea.
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Intermittent Fasting
Late last year I had my annual physical. In general I’m in good health, but my doctor did point out that my cholesterol is high. Not incredibly high — but higher than it should be at my age. I also have a family history of heart disease and high cholesterol. He gave me a year to get my cholesterol down before he was going to put me on medication.
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My News Diet
We live in a world of over-abundance of information. It is remarkable how many different media outlets, social networks, news sources, and random mobile apps compete for your attention. It is easy to get overwhelmed by all the different options — and to waste an incredible amount of time sifting through them all with little value to show for it.
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Rocket Emoji
I love finding small apps that make my life better. This has led me to try I can’t count how many task management apps (my current one is Things, if you’re interested). Many times I eat up cycles for little or no reason.
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Echo Spot — my new alarm clock
My house was already pretty well “connected” with two Amazon Echo Dots and one Google Home (though to be fair, the Google Home has spent the last few weeks in a drawer, sorry Rishi…). I can’t say there was any obvious reason that I needed a new “smart home device” (and I hate the phrase), but I was intrigued by the new Amazon Echo Spot and some of the positive review it received, so I recently got one of those for my bedroom.
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No Twitter January
For a few years now I’ve done a “no alcohol” January. I started that after a particularly long New Years Even when I just felt the need to “detox” a bit. I actually enjoyed doing it and felt quite good afterwards. I also found that after totally giving up alcohol for a while, I reduced my overall consumption moving forward. And I lost a few pounds!
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My New Podcast Habit
In the last 6 months or so I have started listening to podcasts. I had alway wondered how people found time for podcasts and I found sitting and listening to podcasts a bit awkward. However, I’ve started listening to podcasts and I’m really enjoying it. I generally learn something really interesting and useful from the content and it’s a very engaging format. I’ve been really surprised by how much I enjoy podcasts.
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Flying Drones with Code
I have been trying to get my son more interested in coding. He is very interested in engineering and building (we have more Legos than I can count), and has expressed interest in learning to code; but each time he actually gets into coding itself his interest seems to wane. I think it’s just hard to get excited about something that only happens on the screen for him. He’s 8 years old and loves to interact with things in the physical world. So, when I saw in his school newsletter that another Dad had come into the 5th grade science class and flown a drone through Python, I reached out to see how. What could make coding more exciting than having your code fly a done?!?!
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Smart Speakers
I love new gadgets and I have high hopes for voice interfaces in the future. So, I’ve been trying a Google Home and two Amazon Echo Dots along with Siri on my iPhone. I’ve had most of these devices for a while now, but figured I would share my experiences.
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50 Books — My reading goal for the year
favorite reading option — Kindle Voyage
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iPad Pro - My Travel Computer
I’m writing this piece from NYC, where I’ve traveled from CA for two days with only my iPad Pro (okay, I brought some clothes too…). I bought a 10.5” iPad Pro a few months ago and it has really become my go to computer for almost any time I’m out of the office. I find it to be the ideal device when I’m on the go — whether I’m out meetings customers, attending a conference, or just working from a coffee shop; it’s usually all I take.
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My Best Marriage Advice
Pick Fewer Battles
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MY IDEAL BANKING EXPERIENCE
I have had in my mind a simple concept for a banking service — one that I would love to use. After talking to a few friends about it, I thought I would put it down in writing.
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The Challenge with Chatbots
I continue to notice the conversation around machine learning and artificial intelligence (ML/AI) in the finance sector to be driven in large part by the concept of chatbots specifically, and conversational interfaces (eg Amazon Alexa, Google Home) more broadly I find this a bit of a mystery as I think there easier and more impactful areas in finance to apply machine learning. Why the skepticism about chatbots? Here are my reasons:
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Advice for new parents
Be flexible and don’t beat yourself up.
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Three Critical Questions Every Pitch Must Answer
To be successful, every sale must answer three questions for your customer. Clearly this is a simple model of how a sales process works, but I have found it very useful to think of my customer’s asking these three question, in this order. Answering each question effectively and in the right order is crucial to an effective sales process or pitch. Here are my three questions:
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Morning Routine
I’ve never found anything that helps me approach each day with energy and enthusiasm like a morning routine. When I finish everything on my list before my kids are even up I feel like I’ve already won the day. I also feel in control instead of just responding to whatever comes my way first. It’s a great feeling and really kick starts my day!
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Giving Great Presentations
An east five step process
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Why I Love Golf
“A good walk spoiled” is how Mark Twain once described the game of golf. I know many people who would agree with that assessment — and when I can’t seem to find my swing I have been among them. The appeal of the game is a mystery to many who find it to be silly, boring, and overly time consuming (my wife would generally agree with this point of view). However, golf has been a large part of my life for two and half decades now, since I first started pleasingly regularly at the age of 10.
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A Quick Tip
I love quick and simple tricks that help solve real problems. I also love keyboard shortcuts and I’ve recently run across a slick one I wanted to share. I often have small snippets of text that I need to add into emails or calendar invites. For example — my UberConference number or my Calendly scheduling link. And I have found a new, very easy way to access them — through 1Password Mini!
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Golf Statistics
A better way to track and improve your golf game
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You gotta ask the question
The best advice I ever received
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The Circle Theory of Knowledge
I had a math teacher in high school named Mrs Zavastitsa who once explained to the class her theory of knowledge as a circle. You can represent everything you know as a circle, she explained. Every time you learn something new, the circle gets bigger. But even as the circle grows, its size is always eclipsed by what is outside the circle. More importantly, as the area of the circle grows — so does its circumference. Her message was simple — the more you learn, the more you realize what you don’t know.
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My Top Gmail Tips
We all spend more time than we might like (and often more than is reasonable) in email. People are constantly complaining about how broken email is, and I can’t seem to go a week without running across some new email client or killer. However, I’m surprised by how few people have really spent the time to get their email experience set up in an efficient way. I’ve had several people ask me for my email tricks (and having worked for year on Google Apps, I have many). Here are my top tips(somewhat specific to Gmail).
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My Apple Watch Experience
After debating it for a while, I ended up buying an Apple Watch a few weeks ago. Almost everyone who sees it on my wrist wants to know what I think of it (and really if I think they should buy one). My general reaction is that I find the watch as it exists today pretty ‘meh’. I think it is a fundamentally compromised device that does a few things well, many things poorly, but points the way to a compelling future.
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Divergent vs Convergent
Divergent vs Convergent
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“Cutting out a lot of people”
“Cutting out a lot of people”
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Live Debt Free
Live Debt Free
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Intro v Rapportive
Intro v Rapportive
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Reclaiming control
Reclaiming control
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Can you answer these 3 questions?
What’s really going on in your customer’s mind
