Linked Bankruptcy: Everything I wanted to link to but didn’t (volume 4)

Like similar entries, I have spent a lot of time this year on planes and will spend more time before the year is over and so I’ve read things from my growing Instapaper library that are marked “to blog” and here we are finally linking to them. You all know I’m not a breaking-news lover but instead I like reading long-form stories recapping an event that happened months or years ago. I’m linking to them because they’re worth a read, not because they’re particularly relevant today:

Thank you, Guido via Dropbox’ Blog announcing Guido van Rossum’s retirement. Great piece but it was this that I highlighted for later recollection:

But as the company grew, new engineers who joined couldn’t understand the code. Clever code is usually short and cryptic, written by and for the individual who came up with it, but is hard for anyone else to understand—and nearly impossible to maintain. Guido called this “cowboy coding culture”. He recognized its value in our early stages of trying to implement things quickly, but knew it wouldn’t be sustainable over time, so he decided to speak up in his own quiet way.

I have since adopted Cowboy Coding as my favorite phrase when talking to Early Careers talent about prototyping and how it works early on when you’re trying to prove a concept but doesn’t hold up well when billions of people are relying on a product built with cowboy code.

Larry and Sergey: a valediction by Nicholas Carr. My favorite part because I think this statement is poetry and explains eloquently the culture shift Internet has done to us for better or for worse:

That kind of happiness requires a combination of idealism and confidence that isn’t possible anymore. When, in 1965, an interviewer from Cahiers du Cinema pointed out to Jean-Luc Godard that “there is a good deal of blood” in his movie Pierrot le Fou, Godard replied, “Not blood, red.” What the cinema did to blood, the internet has done to happiness. It turned it into an image that is repeated endlessly on screens but no longer refers to anything real.

Twitter’s future could look a lot like its past by Casey Newton in December of 2019 and this relevant bit about Dorsey’s Blue Sky initiative:

This five-person team, to be known as Blue Sky, will be charged with the project — effectively turning Twitter the platform into Twitter the protocol. In such a world, Twitter would be to tweets as Outlook is to email: one client for reading and writing messages among many.

I expected, like Dorsey, this initiative would be dead but their Twitter account is posting updates as of April and they have this site to show for it – and a Twitter Thread explaining where the project is 2.5 years after Dorsey created it as a Twitter employee project. 

The Sabbatical Experiment by David Sparks (2020)

  • I have been working too hard. I need to get better at building in some more fun time during the usual workweek.
  • My “urgent and material” test for client work needs to continue into my daily routine, even on weeks where I am not slowing down. Too often, I put myself in a pickle by overpromising turnaround times on work that is neither urgent nor material.
  • Hyper-scheduling works. As soon as I removed the blocks from my calendar, my production went straight to hell. That was by design last week, but if I did it every week, I would not be able to pay for my shoes anymore.

Why Are Conservatives Obsessed with Pedophilia Right Now? By David M Schell (2020) who posted a follow up in April of 2022 that links here and he added, “This article from Religion Dispatches, I believe, offers a much more compelling explanation for the current (and very weird) wave of right-wingers referring to anyone who acknowledges that same-sex couples exist as a “groomer.”

How Apple Is Organized for Innovation featured in HBR is just a really good read and even though published in December of 2020, is worth a re-read from time to time.

You Know Nothing, Jon Snow by MG Sielger in November of 2020. As MG’s career progressives and one day he retires, I hope someone will find this quote as one of his best about the business of investing in people versus ideas:

“Talking to entrepreneurs, I find it best to acknowledge that you’re perhaps on a journey together and you have no idea how it’s going to play out. So much of it is luck, but even more of it is timing. Hard work is a prerequisite, of course. But mainly to ensure that your company is in the right position to capitalize on the luck of timing, should it come.”

Nobody says hi in San Francisco by Noah Smith in 2020 adding this on to the long list of blog posts I’ve read about how San Francisco was great before “I moved there” 

Pellet Ice is the Good Ice – New Yorker and I agree. It’s my favorite thing about going to the southern states is finding an ultra sweet sweet tea with pellet ice in it.

Can Matt Mullenweg save the internet? By David Pierce in December of 2021. I think this is a story we need to tell. Matt stands pretty unique among open source builders who created remote first companies that are wildly profitable and successful and companies who are set to withstand all of the ups and downs of tech. Matt is one of the good ones.

On Photo Sharing via

As an experiment, I started sharing photos with individual people, privately, over iMessage. I wouldn’t send them a whole collection of photos, just one at a time here and there. And what I found is that when you send an individual person a photo privately, you actually spark a conversation. You end up relating the photo to something that you did when you were a child or reminiscing about when you and the other person traveled to that location years ago

I’m the first to admit, I really don’t have many people I think are friends and I’m not really social with any of my family. Sending a photo to my dad requires opening, clicking the photo icon, uploading a photo from my desktop I exported from Photos for Mac and then sending it over. That’s how I share images with family but since I rarely ever do it, that’s not really an issue. I am lazy so I tell people if they want to see where I’ve been or what I’m doing, just go look at my Flickr page. That’s good enough but for people who do have friends and family, iMessage is the best place to do it but that shows that maybe there is a better way ,no not another messaging app but something more passive. Shared iCloud Libraries is a start but what if we could make that even more dynamic. No hashtags (thanks to machine learning and location sharing), no selecting photos and uploading them and adding filters. Just think Polaroid with your closest friends. Just a thought.

That broken tech/content culture cycle by Anil Dash in early 2022, this 24 part series on how you destroy the internet was fun to read. Anil nailed it. You think of Facebook when you read this but it can be applied to any content company.

iPhone 13 Pro: The Edge of Intelligent Photography by Sebastian de With took 6 months to publish after iPhones 13 arrived but it was well worth the wait.

The Google Incentive Mismatch: Problems with Promotion-Oriented Cultures by Zach Lloyd published in May. I’ve been thinking a lot more lately about the talent crunch in tech and how we reward contributions. This was an eye-opening piece.I probably wouldn’t do well at Google. 

Protocols, Not Platforms: A Technological Approach to Free Speech by Mike Masonic for Columbia University’s Knight First Amendment Institute (quite a mouthful). This August of 2019 article is one I’ve read twice. I love it. I want to print it off and stick it on my wall and read every day. It’s the kind of article that has re-shaped how I think about what we create and what I do next with my time. We need to build protocols. 

Linked: “Instagram responds to criticism with shocking revelation that it will ‘continue to support photos’”

Via TechCrunch:

Instagram head Adam Mosseri posted a video this morning addressing mounting concerns about changes to the app’s feed and its increasing emphasis on video.

Is it lost on these folks that all of the criticisms of Instagram referenced by TechCrunch are videos? Like you’re going to make a video chastising Instagram for losing sight of photo sharing? It’s like making a video that blogging isn’t dead yet and is a healthy and vibrant publishing medium. Um…why not write it? Or in Instagram’s case, publish a photo? 

I’ve been using Instagram again but via an online social media publishing tool and haven’t once installed the app at least not since Facebook bought it 10 years ago. I guess posting photos is not cool anymore. If Instagram is dead and everything is just video, where does one share photos? 

15 Years of iPhone

A picture is worth a million words…shot on iPhone shortly after release in 2007. I was first in my town to get one at a Cingular store and then first in San Francisco to get a 3G a year later. The 2nd iPhone added 3G and the App Store….the first iPhone started the revolution but the 2nd iPhone secured its place in the history books.

A lot has changed in the world of technology in 15 years but oddly enough, I’m still sitting here at a dual monitor desk blogging about technology. In my life though, a lot has changed. Moved across country twice, got married and grew a lot. 

IMG 0165 2

Life: Post-Pandemic

COVID-19 is not over. I must repeat that to myself every day. As a motorcyclist who rides thousands of miles a year on and off road, at track days and long 1000+ mile days in the saddle, I’m aware of risk assessments. The first motorcycle safety course I took in 2016 began with risk and how each risk you take elevates your chance of injury or death. The choice to drink and ride, forgo a helmet or other safety gear, ride in the rain, ride at night or ride with a passenger. Every choice may increase the risk and the federal and state governments have very little control over how you ride your motorcycle other than you being licensed and maybe wearing a helmet.

This pandemic was a similar exercise in risk. I traveled during the pandemic and I’m sitting on a plane writing this blog post. I went to friend’s homes and went shopping and even sat in a crowded bar before vaccines were available in Moab Utah for a night of live music and drinking with friends. To date, I have not contracted coronavirus, exhibited symptoms, or needed to be hospitalized. Over the last 2 years, I was tested 10 times via a cotton swab shoved in my h nose and 5 or so at home tests when I felt a cold coming on that just ended up being seasonal allergies.

We are leaving pandemic status in the United States and down to an endemic status and masks are not required anywhere except federal buildings and some transit authorities like busses and trains. It all happened exactly 2 years to the date that I went home. Viruses don’t have desk-calendars yet after 750 days of this pandemic, offices around the nation wrote into law return to office plans, mask mandates around the country and on planes were dropped and concert halls, theaters and highways filled up again.

I’m not a scientist so this is not a post where I pretend to be one but, to my surprise, my daily check of the NYTimes COVID-19 Tracker has shown me that we are ticking up again on everything but deaths but not as much as I had thought. A national increase from 30K cases a day to 50K cases a day is nearly a 100% increase over 14 days but when I look around this flight where less than 5% of people are wearing a mask and vaccination rates are stagnant, I expected a much larger surge…again, not a scientist, just my observation seeing numbers that aren’t exploding.

…and in the great state of Vermont who I believe still has the highest vaccination rate in the country, we’re having a mini explosion where Vermont is the fastest growing state in the nation outside of Puerto Rico for COVID-19 cases. Why? My non-scientific hunch is having lived in Vermont (or 1 mile from the border), this state has taken the most precautions of any other state even more than California. I still can’t go grocery shopping without wearing a mask and social distancing and so you have a population that while vaccinated, has not been exposed to this virus in any meaningful way. Population density in Vermont is so low that we can visit the store once a month, go home and not talk to or see anyone. You must drive 30 minutes into town to get within 6 feet of a human. We all know that any vaccine does not guarantee you won’t contract COVID-19, only that you’re less likely to and the symptoms, far less severe. It’s not a cure or inhibitor. So, when you have an old and sparsely populated Vermont population, no matter how many of us have been vaccinated (over 80%), all of us can still catch it and this means that when people began socializing again, it has been spreading like wildfire but with no increase in deaths and very few hospitalizations. People are catching it like a cold, getting tested because that’s just how Vermonters are and then staying in their homes and getting over it. Where everyone I talk to in cities has had it once or twice, there aren’t many Vermonters who have had it and so our surge is happening post-pandemic which is as good as we could have it since 4 out of 5 Vermonters are vaccinated. On the NYTimes COVID Tracker, it looks dire and ripe for riffing. “What, Vermont has 80% vaccinations and is surging?!?! LOL. Libtards!” Yeah, that’s one way to look at it. Florida on the other hand isn’t surging because they had 5 previous surges with every new variant. Everyone caught every one of these, some died, most didn’t, and they went back to doing their thing.

Speaking of that great night in Moab singing and dancing at a bar with my friends in September of 2020, a nurse told me everyone in her team were just waiting for herd immunity. Some states took this approach, and some didn’t. It’s going to take some time for researchers to conclude which was the better choice. Is Florida right or is Vermont? Florida told people that if you want to be protected, stay home, and do what you want but the rest of us are going to live our lives and Vermont and California kept everyone home and shut down which inevitably saved many lives more than Florida’s approach. We’ll let the data scientists crunch the numbers on which way was better.

Like I said, I never had the virus and neither did my wife and that’s for the best. That’s not to say we’ll never catch it and I hope we don’t. We remain cautious and careful but live long enough and your risk of dying gets high enough that it’s just going to happen. Catching a virus is similar. On an infinite timeline, we’ll eventually catch it, and it should be just like a cold…I hope.


1000 words in but I’m going to dish out a double-whammy today and that’s remote work. I worked remotely from 2001-2004 as a Tech Blogger and Photographer. I was in high school, but it was a job and I made money. I once again worked remotely when I co-wrote a book with my friend, and we did it virtually. I was hybrid from 2008-2010 working at 3 different startups where the long commute had me working about 2 days a week from home or a cafe to save myself hours on Caltrain every day to little benefit. From 2010 to 2014, I worked hybrid as well going into our office 2 days a week because my entire team was in Belgium. In 2014, I started going to the office every single day until a day in March 2020 when they sent us home to ‘stop the spread in 10 days’. Colleagues struggled and so did I to a degree not because I struggled with working from anywhere. I can make a PowerPoint file on a plane, in an airport lounge, on a bus or on my back porch but I was worried about what I call “technical serendipity” which is more likely to happen when you’re face to face with another bag of germs in a confined space with little air flow (sorry for that one).

I had 6 interns starting in May, just one month after we all went home, and I did that internship remotely and reduced the team to 4 allowing the other 2 to join us the following Summer or a first right of refusal basically. 2 Interns of the 6 volunteered to defer for a year and we went to working remotely as a team. I had to use new tools such as Miro and we relied more heavily on Slack, and I became more of a stickler about following Agile and Scrum methods and interns had to update their Jira tasks before our weekly meetings where I was more passé about it in the before-times.

This first remote Summer, I noticed everyone was getting their job done and communicating effectively via video chats, but we were indeed missing the technical serendipity. After 4 intern groups in a row, all groups of 4-6 undergraduate CS students, I deduced that there are 2 software teams that need hybrid work to be most effective. They can get the jobs done remotely and I’d argue coders don’t need to work a 40 hour week if they have time-management down as a soft skill because wiring code is already such an efficient operation that saves many trillions of human hours in aggregate that I don’t need to have the most effective teams working for me BUT (sorry for the run on sentence)….the 2 teams would be a group working on a brand new product from scratch where collaboration makes up 50% of your day because you’re fleshing out ideas, drawing on the walls, reading body language, vocal inflection and really getting into the weeds and need to stare them in the eyes and determine just how much your partner really cares about this one feature versus them just assigning it high priority in Jira. The second group is early careers. Again, both groups can function remotely. Writing software is not an office task but young people who are just starting out in a corporate environment with one foot in academia and one foot as a professional and they’re learning not just how to write clean code and do it collaboratively with testing, documentation, and planning sessions but also how to manage a calendar, show up to meetings on time, maintain a personal task list or work on time management skills. These folks, my interns, are effective remotely but they’re more effective when we are all in person.

I feel so strongly about this that I will be in the office full time with a team to guarantee their success. Summer of 2021, our entire team was in person for the full Summer, and it was great. We accomplished a lot. Everyone was super effective and the clarity of what we wanted to build then going and doing it with a clear path of planning to execute woke up my technical serendipity meter daily. Showing up to the office and seeing a heated discussion about how we store catalogued images after processing, discussing pros and cons of different database technologies and seeing an intern speak out loud into the universe “okay, who didn’t secure the S3 bucket? Show yourself!” That sort of collaboration in person was huge and more rewarding. Every remote intern I’ve had, in their exit interview, says they wish we had all been in person.

We then went back to fully remote, and I think our team will remain remote forever until the leaders in my company 2-3 levels above me mandate interns are back to in person which will adversely affect things for me despite all the pros.

First, it requires I only recruit talent who can come to our office in New Hampshire. Mostly that requires they must rent a place as a group, and it costs much more to be in our program because they can’t do it from their parent’s home. So, I’ll need interns who come to us and have reliable transportation.

Second, it will put us at a disadvantage because the industry is moving to remote first and I’m not competing with tech companies in our city but with tech companies all around the country. So, an internship that’s fully remote out of California that pays more will be my competition. That’s the case now but we’re also remote.

What about hybrid? I will follow what my work mandates we do and there’s nothing changing now, but hybrid requires the entire office or at least team agree to the model together. I feel like an idiot when 6 of us are sitting around a laptop because we were getting into a technical discussion that wasn’t scheduled and we have to call up the person in Florida who is with us remotely OR the person who stayed home that day to get a package or wait for a plumber and now we’re all trying to share a laptop and talk to that person and pause to let them speak and they’re only hearing half of what’s being said in the room of people. Conference setups solve this problem but anyone who has built an app in a small team from scratch knows that meetings just happen and aren’t always scheduled. Big decisions get made on the fly. You don’t wait for next week’s risk & issues meeting to review something that’s an issue right now.

The big problem with hybrid is when there’s a complete breakdown of the team and someone misses a big discussion because someone forgot to call them when the ad-hoc team meeting starts and concludes without input from the person we just “voluntold” to do the task.

Therefore, for my Summer 2022 program which includes 6 interns in North America and another 10 overseas will be fully remote. I let the team decide. I tell them our office is open and they can come into the office full time. They can even choose to come in the office by themselves if they flourish in an environment where you physically leave your house and go to a space with a desk and white board. Some people just like going to an office to feel productive. However, if even 1 of the interns wants to be remote, we’re going to be remote as well. Or remote-first. The interns are happier, they’re saving more money working at their parent’s house and they’re able to join early meetings with Europeans because their commute is bed-to-keyboard and they’re happier because they’re home with their family and friends and not stressing about finding a place to rent, finding roommates, a car and getting to the office on time.

I will still stand by the importance of technical serendipity and how early-careers and startup teams do benefit from face time but in my team dynamics, those cons do outweigh the pros.

We’re seeing this nationally with every tech company who puts employees first moving to a remote-first model. There are still office spaces in the big hubs and 2-10% of employees go in a few days a week, but you can do your job from anywhere (with a couple of legal restrictions). My employer allows me to work from home, we have an office I can go to any time, and I can work from anywhere with pre-approval. There are massive tech companies like Apple forcing employees to return to office or RTO. In person work is just in Apple’s DNA as a culture and those against it have already resigned. There are plenty of people in line to replace them. Working professionals that don’t fit into the two groups I outlined above can work remotely full time. I’ve done it for years and have seen the entire world wake up to it.

Matt Mullenwag who should be given credit as the pioneer of distributed work not because he did it first but because he has been the champion of it as a matter of principal but his company, Automattic has evolved and designed their day to day to build a remote-first company that works from the beginning. One area that I want more companies to implement is in-person gatherings. Remote first is fine. I can work remotely with 12 people full time, and we’ll get our jobs done but I’d like a quarterly in-person event where we fly to a central location, grab a co-working office and work together and I want a company all hands once a year for 3 days. Everyone, all 5000 of you fly to one place and get together as a company. Automattic does this and it’s a huge benefit because despite being remote, it gives employees a sense of community. We are tribal and our brains haven’t learned how to form bonds virtually yet. You can get very close, but a handshake and a hug are still seal-the-deal actions that bring us closer together and companies are just professional tribes.

In 10 years, it’s not clear where knowledge work will take place and how. Meta verse is interesting, and we’ll see how it plays out. Every time I hear about our future of work in VR, I think of the film Surrogates with Bruce Willis and think…nah I’m good.

COVID-19 isn’t over but the way we live and work in the tech space has changed forever. I’m signing off from somewhere over New Jersey on an airplane with my N95 mask. It’s not a fun experience but it beats catching Coronavirus. Take care.

Sent from my iPad Pro

Twitter Goes Private

If I had comments enabled on this blog, surely someone would have commented on my now 32 day old post, “Twitter, Nine Years Removed” with “#AgedLikeMilk” and they’d be right except my post wasn’t about Twitter, it was about my usage of Twitter and how I feel the product is looking. I think Twitter is on the right path from a product perspective and a lot of reasons I stopped using Twitter are becoming less of an issue. Twitter has become the moral high ground version of Facebook…maybe not in the user base but in the product and that’s a good thing.

Today, April 25th, 2022, a man who has amassed a small fortune saving companies and making them hugely profitable has purchased Twitter with the deal expected to close in the coming months. He’s taking about 1/3 of his own cash paired with money from banks that are loans against his paper wealth to acquire the entire thing in full. This isn’t the private equity exit we all thought would happen to Twitter. It’s much different. To my knowledge, there have been no billion dollar social media companies purchased by one person. There are news media organizations that have been acquired but a company made up by the thoughts and activities of a few hundred million people to be purchased by the man running Space-X, Tesla and more…it’s quite insane.

Twitter has always felt like a town hall to me and so I spent this afternoon feeling melancholy trying to fight the emotion of Twitter’s journey and its future still ahead. I don’t feel this acquisition is on-the-whole a bad thing. I do think that Elon Musk wants a return on his investment and therefore won’t do anything such as open heart surgery with a hatchet that would negatively impact the daily active users, advertisers or the valuable employees who have been working their butts off the past few years to turn the ship around. Will there be drastic changes? Probably but, to his best ability, Mr. Musk will do what he thinks is right hopefully with the advisement of trusted professionals all looking for their payday when Twitter inevitably is taken public again in a decade or less.

What does concern me is what Twitter will become. Facebook is by all measures, a successful product used by billions of people every day and Twitter never saw that success for many reasons that can all fit on a single powerpoint slide but, aside from what the investors wanted, I never saw Twitter as the Facebook killer. The quaint “What are you doing?” question with a 140 characters answer was never going to be the premiere social network for the entire world. Twitter adopted photos, videos, spaces, audio and communities much too late (most in the last 6 months) to overtake Facebook but being the underdog appealed to many people’s emotions. When Twitter failed to monetize users as much as Facebook, “that’s okay” we all said “It’s Twitter, they can be smaller and we’re all better for it” but the success and removal of President Donald Trump from the service changed the course of Twitter forever. Twitter was the most talked about online property for 4 years and their engagement numbers were through the roof and removal of the President on January 6th from the social media service of choice for him was correct if you review Twitter’s own policies that have been in place for years around harassment, hate speech and bullying which the President and many other people violated leading up to actions taken to remove them in early 2021 but in a polarized and highly politicized world, this upholding of their own policies told the world, “We’re anti-conservative”. That was the narrative Twitter was labeled with from that point forward and since then, the organization has been letting new products showcase where they were going all while fighting the internet-branding that Twitter is the silencer of right-wing voices.

For better or worse, that was their bed. 

I don’t think that would forever be Twitter’s perception to the general public but if you read conservative press, it’s the go-to ideal that Twitter is for the woke.

Like nearly every Tech company on the stock market, Twitter’s market cap was slashed in half starting in January of 2022 and a man, the richest in the world as of this writing took advantage of this and made the shareholders an offer they could not refuse. 

What happens next? I don’t think anyone knows, even Mr. Musk. He’s not an activist investor like Icahn, nor is he a consultant who comes in, shakes things up, causes a blood bath and leaves. I believe that he will do his best and put Twitter on the right path and will it succeed? I don’t know. What I will say as a Twitter user is I hope he knows what he’s doing or that the people he puts in charge don’t screw things up too badly. Putting Twitter on a path to profitability and success is great but don’t make it the next Facebook. 

Alex Wilhelm of TechCrunch (I need to email him. I haven’t hung out with him since that Mashable Party in SF in 2008) wrote a very eloquent post today that I couldn’t have written better myself. My favorite part:

Twitter is not perfect and never has been. I haven’t always agreed with the company’s product choices or policy decisions. But what Twitter has mostly done during its life is keep its time-series feed accessible while working to conserve as much room for speech as possible while working on the spam issue. It’s worked.

I spent my evening on Tweetbot reading tweets from @Ev, @Biz, @Jack, @Netik, @Rabble, @Noah and more are up to and more importantly, what people are saying to them via replies. It was therapeutic to even see a few familiar faces talking @ them on the mentions and asking what they think. It’s a reminder that despite having hundreds of millions of users, Twitter is still this small community mostly of nerds who just wanted a way to make a status update permanent and have a little fun at the same time.

I wish Elon Musk success because, if he fails, a big part of my Internet history and memories goes along with it and if anyone current or formerly at Twitter wants to chat, I’m all ears. I’m rooting for every single one of you because I know, no matter who is in charge, you care deeply about the network and want it to succeed. Me too.