Another New House

January 25, 2021 • #

The Summer of Lockdown last year really made us re-think what we want in a house. It hasn’t quite been two years in our current house, and we like the neighborhood and still love St. Pete, but the life changes induced by the pandemic spurred us into buying a new house that fits better with our reoriented priorities.

Another new house

Four primary motivators:

  • Closer to the family, both Colette’s and mine — we’re already in the vicinity, but closer makes things easier
  • A pool! — we thought this wouldn’t be a big deal, until having to spend a Florida summer holed up with the kids with nowhere to go
  • Closer to (better) schools — our kids are just starting
  • Shift to perma-remote work makes short commute distance irrelevant — this wasn’t even in the mind at all when we bought the current place, so loosening the geographic requirements opened up the market a lot

We haven’t moved yet other than bringing over some easy-to-move things plus tools and gear to get some projects done ahead of the full move.

The list of pre-move projects started with just a few but has expanded as I dug into the first ones. We decided that several of these things would be easier to just bite the bullet and do before we move all the furniture and difficult-to-displace items into the house to have to work around. What started with removing popcorn ceilings turned into also removing wallpaper (one of the rooms has layers on layers that have been textured and painted on top of), painting ceilings, painting walls, replacing fans. The rooms I’ve got done so far look great, and we didn’t have to stumble around bulky furniture or loads of kids stuff to get these messy projects done.

There’s an expanding list of other side projects coming together, but none that will prevent us from getting moved.

One of my focus goals for the year is to devote more time to home improvement and DIY stuff than I have previously. It requires back-seating some other priorities, but there are a few things in the works that’ll be super satisfying if I can make the time to work on them. One I’m most excited about is an outdoor kitchen-slash-detached micro office space. Once we get moved that’s one we’ll be tackling first, planning to document the process and maybe even make some video along the way.

Waypoint — a Raspberry Pi GPS Tracker

January 13, 2021 • #

Books of 2020

January 7, 2021 • #

I’ve gotten a lot more selective about books to read in the past few years. My 2020 reading goal was 30 books, giving me space to absorb them and take better notes, and to permit reading longer stuff I could take my time with.

Here’s my list for the year, with stars next to the favorites.

Brave New World Brave New World by Aldous Huxley Published: 1932 • Completed: January 7, 2020 • 📚 View in Library

I had never read Huxley’s classic dystopian science fiction. It was alright, but to me it’s one of those classics better in its influences than the original source material. Wasn’t bad, but didn’t enjoy it as much as I expected I would.

Zero to One Zero to One Notes on Startups, or How to Build the Future by Peter Thiel Published: 2014 • Completed: January 11, 2020 • 📚 View in Library

On the surface, Zero to One looks like pulpy tech startup how-to book, but it’s better described as an introduction to Thiel’s worldview about business.

Mastering the Market Cycle Mastering the Market Cycle Getting the Odds on Your Side by Howard Marks Published: 2018 • Completed: January 29, 2020 • 📚 View in Library

Investor Howard Marks is well known for his memos that lay out his thoughts and opinions on the current state of the market. This book is sort of a collection of his thoughts on the cyclical nature of markets.

Deep Medicine Deep Medicine How Artificial Intelligence Can Make Healthcare Human Again by Eric Topol Published: 2019 • Completed: February 9, 2020 • 📚 View in Library

A solid read on the state and potential of AI applications in health care. There’s a ton of potential for AI and machine learning in the space, but also a load of hype distracting from its true prospects. Areas like radiology, documentation, note-taking, dictation, and other “mechanical” processes can be moved aside making space for greater unique human connection — things doctors can do that machines can’t. Some fascinating (and often sad) statistics about the methods of modern healthcare.

Where Wizards Stay Up Late Where Wizards Stay Up Late The Origins of the Internet by Katie Hafner Published: 1996 • Completed: February 29, 2020 • 📚 View in Library

A brief history of the formation of ARPA and the evolution of the internet from the early 1960s to the mid-90s. A quick read and solid primer on the players involved in the early days.

The Phoenix Project The Phoenix Project A Novel About IT, DevOps, and Helping Your Business Win by Gene Kim, Kevin Behr, and George Spafford Published: 2013 • Completed: March 13, 2020 • 📚 View in Library

Three writers with engineering backgrounds write a novelization of a devops team encountering and solving dozens of problems from within their broken technology organization. A revival of Eli Goldratt’s The Goal, covering management science concepts like agile development and the theory of constraints. Much more entertaining than it sounds.

The Dream Machine ⭐️ The Dream Machine J.C.R. Licklider and the Revolution that Made Computing Personal by M. Mitchell Waldrop Published: 2001 • Completed: March 14, 2020 • 📚 View in Library

I’ve read a lot about the history of computers, but I didn’t realize the deep influence of JCR Licklider until reading this. This book is nominally a biography of “Lick”, but also uses him as a thread to wire together many of the seminal moments in the evolution of computers and the internet, since he was directly involved in so much of it: interactive computing, time-sharing, IPTO/ARPA, funding research at Stanford, UCLA, Berkeley, Engelbart’s work, Project MAC. This was one of my favorites in a long while. Probably generated 20 new books added to my reading list (a strong signal for an interesting work).

I wrote a thread after I finished it with some of the touchpoints of his career.

The Revolt of the Public ⭐️ The Revolt of the Public And the Crisis of Authority in the New Millennium by Martin Gurri Published: 2014 • Completed: April 9, 2020 • 📚 View in Library

I can measure the “interestingness” of a book by the highlights-to-page-count ratio. Since all of my highlights go to Readwise, it’s funny to look at this number and how accurate that statement is. This book was written in 2014, but reads like Gurri was living in the summer of 2020 when he was writing it. The deep insights into the root causes of dysfunction in institutions, media, and politics show that he was a proverbial Cassandra with the answers to why public outrage, distrust, populism, and social media firestorms have been happening more and more frequently. The book is light on solutions to these problems (Gurri says he “does not make predictions”), but the first step to knowing where to start is to accurately diagnose causes. A phenomenal read. I’m glad to see that Stripe Press reissued it to increase its audience.

Ubik Ubik by Philip K. Dick Published: 1969 • Completed: April 11, 2020 • 📚 View in Library

PKD has a deep bibliography of drug-fueled speculative fiction, and Ubik is one of his most acclaimed. Set in a “future 1992”, it features psychics powers, corporate espionage, reality distortion, time travel — a blitz of crazy sci-fi storytelling in 200 pages.

The Three Languages of Politics The Three Languages of Politics Talking Across the Political Divides by Arnold Kling Published: 2013 • Completed: April 20, 2020 • 📚 View in Library

For a few years I’ve gotten interested in the subject of polarization and why we end up with such steep divisions of opinion on literally every single topic. Jonathan Haidt’s The Righteous Mind is probably the richest analysis of this, picking apart the moral psychology of why people believe what they believe (and why they think so negatively about their “opposition”).

From his appearances on EconTalk, I started following the work of economist Arnold Kling, who wrote this short book breaking down these definitions from a perspective similar to Haidt’s. He posits that when two people hold differing beliefs and disagree, we’re actually speaking different languages, not even understanding the basis for arguments an opponent is making.

See also this interesting discussion between Kling and Martin Gurri on institutional decay.

Darkness at Noon ⭐️ Darkness at Noon by Arthur Koestler Published: 1940 • Completed: April 21, 2020 • 📚 View in Library

Picked this up from a mention on The Fifth Column. Koestler fictionalizes Stalin’s Great Purge, telling the story of an old party member called Rubashov, imprisoned and put on show-trial for treason. It’s told from his perspective as he sits in prison recalling the events that led to the party he helped create eating its own.

A Time to Build A Time to Build From Family and Community to Congress and the Campus, How Recommitting to Our Institutions Can Revive the American Dream by Yuval Levin Published: 2020 • Completed: April 28, 2020 • 📚 View in Library

I’d heard good things about this from interviews with Yuval. There are strong ties from his ideas to those of Gurri in Revolt: the thesis that institutional decay is at the root of many of our modern problems.

How to Take Smart Notes How to Take Smart Notes by Sönke Ahrens Published: 2017 • Completed: May 16, 2020 • 📚 View in Library

Getting into Roam this year got me seriously rethinking my haphazard note-taking habits. Within the #roamcult community, Ahrens’s book is one of the canon works on the “zettelkasten” method, Niklas Luhmann’s approach to decentralized, network-based thinking. It’s helped me immensely in learning and recall, since I now have a more deliberate approach to knowledge capture from the many books I read.

It’s excellent to see the community springing up around continuous learning, writing, and richer note-taking. Tools like Readwise have also helped to take this to the next level.

Check out this interview with the author, which gives a great overview of his work.

Beastie Boys Book Beastie Boys Book by Adam Horivitz, Michael Diamond Published: 2018 • Completed: May 31, 2020 • 📚 View in Library

Music bios don’t make frequent appearances in my reading list, but I had to read this one. The Beasties are one of those groups that have maintained high status in my music rotation for 2+ decades. Rarified air, since most sort of tail off or become tired after long enough.

I have a copy of the fantastic hardcover edition, but I actually listened to this one in audio format. Guest narration from folks like Mix Master Mike, Chuck D, MC Serch, LL Cool J, Spike Jonze, and many more folks from their extended universe. Highly recommended.

Ra Ra by Sam Hughes Published: 2014 • Completed: June 7, 2020 • 📚 View in Library

This one came across through Twitter, a self-published work from writer and programmer Sam Hughes. In the world of Ra, magic is real and studied as a branch of engineering. The protagonist is a practicing mage who ends up caught in a conspiracy. A creative and original work of fantasy/sci-fi.

How Innovation Works ⭐️ How Innovation Works And Why it Flourishes in Freedom by Matt Ridley Published: 2020 • Completed: June 20, 2020 • 📚 View in Library

Innovation is a phenomenon frequently taken for granted in today’s world. Since we’ve seen booming improvements in scientific discovery, public health, industrialization, and economics over the past 3 centuries, no one alive today has ever known anything different. So it’s easy to think that innovation springs forth from the ground, a free and bountiful resource we all get to enjoy the fruits of.

But innovation isn’t automatic — it requires giving creative individuals the freedom to experiment, to drive toward continuous improvement through the relentless application of trial and error.

The front half of the book is full of examples sliced from the history of technology and how innovations we all value today originally came to be: Edison’s light bulb, the Wright flyer, nitrogen fixation, vaccinations, the steam engine. Every innovation we know of was not the result of magical, eureka-like discovery, but rather the slow and steady, compounding progression of building on thousands of prior incremental discoveries.

In the back half (which should be required reading in history classes), Ridley succinctly lays out innovation’s essential ingredients — it’s recombinant, team-based, serendipitous, gradual, decentralized — and many other core principles to define innovation’s evolutionary quality.

One of my top reads of 2020, for sure.

I’m hopeful that the rise of the progress studies movement this year will continue to catch on with more people, spreading the understanding of how innovation truly works to a wider audience.

The Lean Startup The Lean Startup How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses by Eric Ries Published: 2011 • Completed: July 16, 2020 • 📚 View in Library

This is practically required reading for anyone in the startup world, so I don’t know how I went so many years without reading it. Since it’s been built upon in the culture of tech and become a native part of the lingua franca of the industry, there wasn’t much news to me here. That being said, it’s a solid foundational work in the scene, with many core principles still relevant today and beyond.

The Gervais Principle The Gervais Principle Or The Office According to 'The Office' by Venkatesh Rao Published: 2013 • Completed: July 30, 2020 • 📚 View in Library

Venkatesh Rao is one of the most interesting people in the internet writer-verse these days. This one is a collection of long-form essays he wrote, building a theory of business organizations using The Office as a framing device for establishing the nomenclature and examples of his theory, which builds on top of a Hugh MacLeod cartoon from years ago.

It sounds absurd when you start reading it, but continuing through each part you realize how sharply spot-on this analysis of corporate culture is.

The Remains of the Day The Remains of the Day by Kazuo Ishiguro Published: 1989 • Completed: August 5, 2020 • 📚 View in Library

This one is highly acclaimed work of historical fiction. The writing is quality and dialogue is incredible, told from the perspective of an English butler at the tail end of his career. I felt it was sort of slow, but had some interesting moments. Would like to read more of Ishiguro’s other work.

Inspired Inspired How To Create Products Customers Love by Marty Cagan Published: 2008 • Completed: August 27, 2020 • 📚 View in Library

Marty Cagan’s blog has been a resource for me for years as a product manager. This book collects up Cagan’s organizing principles for how product teams should be assembled and work together. Some solid insights here, but if you’ve read the archives of the SVPG blog, you won’t find any revelations you haven’t already seen.

Mythos Mythos The Greek Myths Retold by Stephen Fry

part 1 of Stephen Fry's Great Mythology

Published: 2017 • Completed: October 2, 2020 • 📚 View in Library

For some reason mythologies are fascinating to me. Last year I read Edith Hamilton’s classic Mythology, and before that Gaiman’s revitalization of Norse Mythology and Joseph Campbell’s analysis of myth’s roots in The Hero With a Thousand Faces. Looking at how stories start to form as ways to explain the unexplainable, and how they pass down through culture helps provide a frame for how other ideas coalesce and spread.

Like with Gaiman’s take on the Norse gods, this one is humorist Stephen Fry’s rework of the Greek myths. Compared to other classicists like Hamilton or Bullfinch, Fry’s modern take is far more entertaining and approachable, while still deriving from the same original sources like Hesiod, Ovid, and Homer.

Bonus: Fry’s narration in the audio version is fantastic.

The Psychology of Money The Psychology of Money Timeless Lessons on Wealth, Greed, and Happiness by Morgan Housel Published: 2020 • Completed: October 3, 2020 • 📚 View in Library

Morgan Housel’s blog is a treasure trove of fascinating ideas. I preordered this one early in the year when it was announced, and devoured it in a couple days when I got it. It’s a great primer on how to think about finances, savings, retirement, from a first-principles perspective, readable by anyone with no prior knowledge of investing or finance required.

The Decadent Society The Decadent Society How We Became the Victims of Our Own Success by Ross Douthat Published: 2020 • Completed: October 16, 2020 • 📚 View in Library

Back on the topic of stagnation and institutional decay, this one was New York Times columnist Ross Douthat’s entry on that theme. His basic framework defines “decadence” as a society rife with 4 qualities: stagnation, repetition, sterility, and sclerosis.

I’m not sure I share Douthat’s depth of pessimism about the stagnation hypothesis (which has been well written about elsewhere), but there’s some insightful analysis here about possible root causes to some of this stagnation.

Like with Revolt and A Time to Build, it’s hard to prescribe solutions to the problem, but worthwhile figuring out the diagnosis.

Peter Thiel wrote a good essay on the book earlier this year, if you want to read more about it.

Gut Feelings Gut Feelings The Intelligence of the Unconscious by Gerd Gigerenzer Published: 2007 • Completed: October 31, 2020 • 📚 View in Library

I first learned of Gerd Gigerenzer on EconTalk where he discussed the ideas from this book. If you’re familiar with Malcolm Gladwell’s Blink, this covers some of the same concepts, but in a much deeper and interesting way.

The core idea is that when we use our “gut” to make decisions, it’s not random, emotional guesswork driving the rationale; gut is driven by heuristics, rules of thumb, and complex impossible-to-articulate models of reality that we become programmed with through millions of tiny events and experiences. Gigerenzer draws a coherent picture of the theory with many examples of the counterintuitive power of heuristics.

The Splendid and the Vile The Splendid and the Vile A Saga of Churchill, Family, and Defiance During the Blitz by Erik Larson Published: 2020 • Completed: November 27, 2020 • 📚 View in Library

This one is a great history of Britain through the Blitz of 1940. It mostly follows Churchill and his close circle of family members and advisors as they make their way through from the evacuation at Dunkirk through the German bombing campaign and the eventual entry of the United States into the War. I’ve never read any of Larson’s other work, but he’s a fantastic writer of narrative history. This one reads like a thriller in parts, with the UK perched on a knife’s edge in whether they could withstand the onslaught and successfully fight back.

I wrote a bit about the book in RE 5 a few weeks ago.

Seeing Like a State ⭐️ Seeing Like a State How Certain Schemes to Improve the Human Condition Have Failed by James C. Scott Published: 1998 • Completed: December 2, 2020 • 📚 View in Library

I was tipped off to this one I think originally by a post from a Venkat Rao post, talking about the central theme of the book: legibility.

SLAS centers around a concept Scott calls “authoritarian high modernism”: an approach to organizing society that attempts a planned, centralized scheme for a system — could be a farm, a city, a company, an economic system, or an entire country — with the central goal of making the peripheries more legible to the center. High-modernist designers, planners, or government leaders look at “messy” systems of organization and see a lack of order. Scott’s claim is that this top-down worldview simply ignores or assumes useless what it cannot quantify, monitor, and manage. Complex systems exhibit apparent disorder, but at the lowest levels are often surprisingly rational.

This book is worth revisiting regularly. It was profound to me and connects dots between many other distinct theories and ideas I’ve been interested in.

I went deep on this idea in RE 4. Check that out to read more about legibility.

Competing Against Luck Competing Against Luck The Story of Innovation and Customer Choice by Clayton Christensen Published: 2016 • Completed: December 6, 2020 • 📚 View in Library

Christensen is most renowned for his work on disruption theory (The Innovator’s Dilemma), but he’s been instrumental in developing “jobs theory”, which I find more practical to apply to the day-to-day process of building. In principle it guides you to think about products or services as things your customers are “hiring” to perform a “job”.

If you’re interested in Jobs Theory stuff, I’ve found Ryan Singer’s work fascinating, following these threads for product-building. His newsletter is great.

Kim Kim by Rudyard Kipling Published: 1901 • Completed: December 12, 2020 • 📚 View in Library

I’ve had Kipling on my reading list for years and didn’t know where to start on his works. Kim tells the story of an orphan that finds himself drafted into the service of British intelligence in the “Great Game” of geopolitical influence against Russia.

The backdrop is an interesting tour through the different cultures of the Indian subcontinent.

Thinking in Systems Thinking in Systems A Primer by Donella Meadows Published: 2008 • Completed: December 23, 2020 • 📚 View in Library

Throughout the year I kept encountering this subject of complex systems. Systems thinking is something I found intriguing, and as happens with many books, a perusal of the first few pages of Dana Meadows’s book quickly turned into consuming the whole thing. As the subtitle says, this book is a fantastic primer on the core principles, and lays out the central elements of stocks and flows with clear diagrams.

I went deeper on systems thinking and feedback loops in RE 6 a couple weeks ago.

Sid Meier's Memoir! Sid Meier's Memoir! A Life in Computer Games by Sid Meier Published: 2020 • Completed: December 31, 2020 • 📚 View in Library

While I’m not a gamer these days really, except for time with the kids, my youth was spent playing lots of PC games, especially the ones in Sid Meier’s catalog. Civilization II was absolutely formative for me in more ways than entertainment. I’d credit that game with sparking an interest in history, cementing a deeper one in geography, and was the starting point for a love of strategy games of the era.

I’m still working on what my reading goals will look like for this year. I’d like to be more purposeful about studying specific subjects more deeply rather than the semi-haphazard selections I tend to make normally.

2020 Goals Review

January 2, 2021 • #

I’m a few days late in getting around to reviewing how I did on the goals for 2020, but what’s new there in a year full of challenges? It’s an understatement to say that for anyone that set quantified personal goals at the start of the year had a rude awakening in March. We all encounter setbacks along the progress bar throughout any year, but this one was a doozy, and a protracted one that just kept dragging out.

Luckily here in Florida we’ve been able to have some normal(ish) activities the past few months. Even just taking the kids back to playgrounds again around August was like a weight off the chest. The months of cabin fever dragged down everything for the whole family.

So how’d I do on those goals anyway?

Activity Progress Pace Goal Plus-Minus
Running 650.24 miles 650 miles 650 miles +0.24
Meditation 1070 minutes 3120 minutes 3120 minutes
Reading 31 books 30 books 30 books +1

Here are my original notes from the start of the year with some comments on each.


Run 650 miles — When I set 500 as a target for 2019, I thought it’d be all I could do to hit that. I ended up landing on 615. With consistent effort (it requires an average 12.5 miles per week) I can definitely hit 650. Feels incremental, slightly uncomfortable, but attainable.

With a couple of days left I crested the running target just barely, 2 free days to spare. Throughout the entire year I don’t think I got more than a couple of miles ahead of the pace marker. I procrastinated way too frequently

Run 2 half marathons — Did one last year, will shoot for one in the spring and one in the fall or winter.

For obvious reasons this one wasn’t possible unless I did them on my own, which would be a long shot for me. I may try one this year, we’ll see.

Deeper meditation — In my takeaways on this from last year, I mentioned the lack of depth with short, frequent sessions. This year I’m going to try doing 2 sessions of at least 30 minutes per week. I’ve read from multiple sources that anything shorter than about that length doesn’t get you all the way to the “present” state that mindfulness techniques are targeting. Half an hour will feel like a long time, but only twice a week should be fine.

2020 would’ve been a great year for improving meditation practice. For no good reason I just couldn’t get myself back into the routine to do it. I’m not sure what I’ll do with this in 2021. I’d rather not put a goal up on the board with no real plan to try at the moment. Can always start anytime without an official goal.

Begin strength training — Shooting for 3 days per week. My plan is to get a setup in the garage to do workouts pre- or post-evening run.

Another one I just never got around to. We just bought a new house (which I’m due to write about, more on that later), so when we move I’m hoping to get a zone set up in the new garage and work this in sometime in the morning after everyone’s in school. Easing into it and getting consistent will be the key.

Reading, Learning, and Writing

Read 30 books — I’m lowering the number this year, but have no plans to read less. I want to prioritize more long-form, deeper books that I’ve got on the shelf.

I notched just over this without trying too hard. I even had a few spells throughout the year with very little reading.

Continue daily posts — I’d also like to force myself to write posts on 1 book per month.

I started 2020 with an intent to keep this going. As it was I made it to the 2-year streak mark in mid-October and put myself on hiatus. It was a good move since it’s given me a little breathing room, with time to spin up what I’ve been doing with the newsletter: Res Extensa.

Study finance — With a half-decade of being heavily involved in the business end of a SaaS company, I’ve gotten a “crash MBA” in budgets, finance, and tons more. I plan to spend more time learning about markets, investing, and economics to have a broader understanding.

Didn’t spend much time here, but I did get some personal budget stuff in order. Not quite done yet.


Host Fulcrum Live 2020 — The name of the event is TBD, but we’ll be doing another iteration of our user conference that we last did (with success!) in 2017.

Really want to be able to do this (something) sometime in 2021.

Grow the team — Much of my time this year will be focused on team growth. No hard targets yet, but we have some things in the works that’ll be expanding our team.

We grew quite a bit this year, even with the tumultuousness of shifting to full remote.

Other Things

Share more posts from the blog — When I started the daily posting habit in fall of 2018, I made the intentional decision to just put posts out there and see what would happen organically. No expected plan to drive traffic, just post and leave it be — personal journal out in public. One of my main reasons for doing that was to reduce the friction in getting things out there. The idea that every post was getting tweeted or shared could’ve made me overly attentive to perfection and polishing, something I wanted to avoid not only because it’d take longer on net for each new post, but it could make me hesitant about certain things. This year I’ll plan to share more widely the content for feedback and discussion.

I didn’t do as much of this as I’d planned. Footnote to include this one for 2021 goals.

Take a few local weekend trips with the family — There’s a shortlist of places in driving distance I’d like to take the kids to, like on long weekends.

COVID shut us down here. We did get to drive up to the Georgia mountains for a week in late October. Another one that I hope can be resurrected for an improved 2021. All in all I hit the big primary targets.


December 28, 2020 • #

As little as Twitter has moved as a product in the last several years, the amount of time I spend on it clearly demonstrates that there’s gold there that no other product can replace.

If you curate your following list well, the quality level of the interactions you can have and people you can meet are incredible. I haven’t found another social network as good at finding interesting ideas.

A limiting aspect of Twitter is how biased toward “now” it is1. It’s inherently an ordered timeline. Algorithmic recommendations surface some recent things, but not from beyond a day or so. Much goodness is bound up in the Twitter archives, but it’s nearly undiscoverable. If you find an interesting new person to follow, you only get this extremely recent window into their interests.

I saw this new project from developer Geoffrey Litt, something he calls Twemex: a memex for Twitter. It shows promise to resolve this problem. It’s a simple Chrome extension that layers in some missing features for exposing the historical gems embedded in peoples’ timelines. I’ve been using it for a couple weeks and it’s an excellent addition to the product.

It adds a persistent sidebar for all of the pages on Twitter, which includes different things depending on context.

Firstly it has overhauled search. Since it lives in the Twemex sidebar view, you can live search while you’re drafting a thread, finding similar ideas (and filtering down to your past tweets or people you follow) to quickly link into past thoughts.

Second, there’s a fun “On This Day” feature that shows on the main timeline feed that resurfaces your own tweets from the same day in years past. Always fun to see what you were into. Sometimes it might even provoke you to revisit old ideas.

And third (my favorite), when you visit a user’s Twitter profile, you get a “Best Of” selection of their past posts. At a quick glance it gives you a sense of previous ideas, links, and material a user posts, which helps you select and curate your following lists better. I follow a lot of people on Twitter, but always first peruse timelines to determine if they’re worthy of a follow.

Geoffrey shows searching of likes and bookmarks, highlight curation, and profile notes (to let you annotate why you followed someone). All excellent additions that’ll make Twitter so much more useful. It’s still in private beta at the moment, but I’m sure will be available as a public extension early next year. Follow Geoffrey on Twitter to see its development.

Sometimes you run across extensions or add-ons like this that should just be native product features. Twemex should just be the “Twitter Sidebar.”

  1. Also, as it happens, one of its advantages. Twitter is the best representation of a global water cooler you can find 

Enterprises Don't Self Serve

December 11, 2020 • #

In the wake of Salesforce’s acquisition of Slack, there’s been a flood of analysis on whether it was a sign of Slack’s success or failure to grow as a company. It’s funny that we live in a time when a $27bn acquisition of a 7-year-old company gets interpreted as a failure. I’d consider it validation for their business that a $200bn company like Salesforce makes their largest acquisition ever on you. Broadly, it’s a move to make Salesforce more competitive with Microsoft as an operating system for business productivity writ-large.

One likely driver of selling now vs. later was the ever-expanding threat from Microsoft’s fantastic execution on Teams over the few years. Slack saw Microsoft’s distribution and customer relationship advantage, and that they’d have a beast of a challenge peeling away big MS customers. This sort of “incumbent” position in the enterprise is one of the strongest advantages Microsoft has, and they’ve been savvy in playing their cards to feed off of this position.

As a new entrant to the enterprise software space, Slack’s bottom-up product strategy has been one of their key advantages that fed their hypergrowth since 2014. The relentless focus on product quality drove viral adoption within user groups inside of organizations. Classic land-and-expand: get teams to adopt for themselves, and weave your way from that beachhead into the rest of the organization, with an eventual (often reluctant) official blessing from IT departments. The product-led growth (PLG) model (of which Slack was an early success story) allows new entrants to serve users first and foremost, sliding in under the radar of corporate buy-in inside companies: “shadow IT”, as it’s known.

Within large companies, self-service and a product-led approach can get you a long way, as Slack and many others have demonstrated. But at a certain size you hit friction points with growth inside large accounts. Enterprise customers rarely adopt software with zero engagement from product makers. But Slack and other PLG successes have been able to push deeper than previously thought possible with hands-off, sales-free tactics.

Former founder and now-investor David Sacks wrote a great Twitter thread on this topic (also discussed on the All-In Podcast), reacting to Slack’s lateness to implement a sales organization:

“Enterprises don’t self serve”

There’s no question that product-led is the way to go to get validation, traction, and growth, and that it’s still instrumental to building horizontal customer footprint. Sacks’s point is that Slack didn’t handle the enterprise scaling requirements early enough (they now are).

Bottom-up is great for top-of-funnel customer acquisition (Sacks says “lead gen”), but starts to falter as a growth driver at some scale. The trick in architecting a hybrid product-led vs. sales-led dichotomy is finding where and when in the lifecycle to transition growing customers from one to the other. What the PLG movement has done for SaaS companies is carry customer expansion further into companies than before. The likes of Slack, Atlassian, and Twilio carried themselves to enormous scales on the back of a PLG, self-service strategy.

Why does PLG decelerate?

Why would an enterprise company (or one that’s grown their use of a product to enterprise-scale penetration) not be able to self-serve the larger deployment? Why couldn’t a product company rely on self-service once a company’s usage grows to that point? It seems reasonable that if a customer scaled to a couple hundred users that the continued expansion would be an easy justification; if it’s working, why not keep expanding?

There are a few related reasons why relying on customers to serve themselves slows down at scale:

  • In large companies, individuals are no longer able to make decisions — champions for a product (that may already be using it in their team) need to build consensus across a diverse group of stakeholders to justify expanding
  • Too many cats need to be herded to get a deal done — see item 1, often a stunning number of heads need to be convinced, justified to, and won over; corralling the bureaucracy is a whole separate project unrelated to the effectiveness or utility of the product
  • Rarely no individual “buyer” — user can’t purchase product, purchaser has never used product; incentives for each stakeholder working at cross purposes (one is looking to complete a project, one is looking to cut budget, one is looking to impress the press, etc etc)
  • If you have a champion, they have a day job — And that job isn’t playing politics with accounting, legal, execs, IT, and others; there’s no time for the customer to play this role for you I can speak from experience on all dimensions of this. In the early days of a bottom-up product, landing that big logo and watching them grow looks like this — you’re growing seat count and things look to be taking off:

Bottom-up, product-led growth

Watching it happen is magical, especially if you’ve got an early product and/or small team. You’re building product you think is useful, and you’re being validated by watching it weave its way up into a company with a household name.

But you eventually discover that true enterprise-scale adoption looks more like this:

Moving laterally

The customer you thought you were growing wasn’t truly the whole enterprise, but only a department or division1. In many (most?) national- or international-scale companies, bridging to neighboring departments is effectively selling to a whole new customer. Sure, the story of your product’s impact from adjacent teams’ use cases is helpful, but often the barriers between these columns are enormous.

What you need is some fuel to help jump the gaps.

Enter your sales team

The reason for the sales team is primarily to coordinate and communicate with the stakeholders described above the on behalf of the buyer.

Sales to transition between departments

There are unicorn enterprise customers out there where you’ll find a champion willing to saddle this burden of selling your product to themselves — sometimes a particularly aggressive or visionary IT leader, or exec — but this is a rarity. You can’t and shouldn’t rely on this existing in most organizations.

On the surface this thought runs counter to a lot of recently popular ideas on product-led growth. But what Sacks is claiming in his thread doesn’t invalidate product-led, bottom-up as a strategy — in fact he says the opposite.

What it does say is that the go-to-market shouldn’t be a binary methodology: either you’re bottom-up / product-led OR top-down / sales-led. For many B2B SaaS companies, the ideal system design is optimizing for product-led evolving into a sales-led approach when a customer reaches a certain stage of the lifecycle.

Product-led to sales-led transition

Even for teams that understand the dynamics of both methods, the hard part is finding the right place in the cycle for the methodology to flip. If one set of tactics is largely owned by the product, design, and marketing teams (PLG), and the other owned by sales and customer success teams (SLG), then without proper experimentation, management, and cultural behavior reinforcement, it’s possible that one of those teams leans too far beyond the transition point.

Sales too early stunts investments on super-efficient organic growth techniques with PLG; too late means customers may have slowed expansion because you weren't there for the assist in keeping the growth moving upward Sales too early stunts investments on super-efficient organic growth techniques with PLG; too late means customers may have slowed expansion because you weren’t there for the assist in keeping the growth moving upward

This continuum is, of course, not fixed for all time or all companies. And those transition points are a lot more fuzzy in reality than in a chart.

PLG is growing in effectiveness over time, so the optimum transition stage from PLG to SLG is moving rightward for many types of products. A number of factors could cause this phenomenon. There are more and more companies opting for a PLG approach, but I think this is a response to changes in customer behavior more than it’s a modifier of customer behavior (though those effects move both ways). Things like technical comfort, the prevalence of self-service solutions in consumer technology, ease-of-use as a table stakes expectation, a wider competitive market for tools, and the sophistication level of technology expanding tremendously over the last 10 years are all moving parts that contribute to self-service becoming more widespread.

  1. The more hands-off you are in early usage and ramping up, the less you often know about the specifics of the customer. Is it an intern leading a pilot project? Is it a real, funded initiative? Often hard to tell if you’re “auto-scaling” on a PLG strategy. 

Goal Progress: November

December 1, 2020 • #

We had a hurricane blow up part of a week of productivity around here, but I still limped along with some middling progress on the year’s goals. I’m behind the targets this year late in the game, but I’m still happy with the results. I can still close the gap on the running target, at least.

I’ve been thinking about an idea Patrick O’Shaughnessy wrote about recently on “growth without goals” — setting up systems to be able to pursue and achieve personal growth without having hard numbers on a scoreboard. Using this site as a public accountability tool helps me to keep these top of mind for continued effort. I’ll have to give this some thought as we near the end of 2020 as to how I want to set up my personal growth systems for 2021. I’m thinking an evolution is in order that creates more space for discovery of new interests without interrupting growth in focus areas.

Activity Progress Pace Goal Plus-Minus
Running 588.6 miles 597 miles 650 miles -8.02
Meditation 1070 minutes 2607 minutes 3120 minutes
Reading 24 books 27.53 books 30 books -3.53

Reading seems like one that’s particularly absurd to quantify as num_books_read. The dimensions of depth and breath of a “book” are so all over the place that the metric approaches uselessness as a measurement. I’ve tried to avoid selecting material I choose to read around “managing to the metric”; the last thing I want is to end up reading 11 garbage quick reads just to hit an arbitrary number. The purpose is defeated if I were to fall into that trap.

One idea that comes to mind as I’m writing this is selecting target study areas to read about — something like choosing 4 or 5 topic areas I want to dive deeper in and measure to how many of those subjects I learn more about. A trackable tool to keep me honest would be useful, but I’m conscious of falling prey to simply managing what’s easily quantified.

With the downramp in the previous daily posting regimen, I’ve used that time mostly to catch up on a bunch of new ideas cooking in (and about) Roam, and put out a couple of newsletters, issues 4 and 5 of Res Extensa. (Subscribe here!)

It’s been fun to do so far. I’ve landed on this idea for the last couple of following a theme topic rather than a simple digest of links or interesting things. That could be interesting, but there are a lot of great “curator” newsletters out there already. Issue 4’s theme was legibility, from James C. Scott’s epic Seeing Like a State, and issue 5 looked at alternate timelines from a couple of different angles.

Weekend Reading: Digital Librarians, Tech Trees, and Alternate Histories in Maps

November 22, 2020 • #

📑 Chief Notion Officer

Julian Lehr is onto something here. All modern organizations are plagued with a problem of managing internal documentations. We have ample tools and keep squishing the problem from one place to another: wikis, search, tasks — it’s a game of whack-a-mole to find the right version of a document. He ponders at what size it makes sense to invest in a “digital librarian”:

A friend at Stripe recently suggested – half-jokingly – that we should hire a librarian to organize all our internal data and documentation. The more I think about it, the more I like the idea. Perhaps every company should hire a Chief Notion Officer once it hits 100 employees??

🌳 The Tree of Up

Up created a tech tree representation of their product and roadmap. Genius.

🌍 Intriguing Maps That Reveal Alternate Histories

Speculative maps of alternate historical timelines.

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