Today, I turned thirty-nine.

I celebrated the day with my most favorite people in the world: my wife, my son, and my dog – my “quaranteam” with whom I’ve spent nearly every moment of the past year.

This year was unique not only because of the pandemic, but also because it was a year that I took off from work. It just so happened that my wife did the same. Our decisions to do so were made pre-pandemic and exclusive of each other’s, but the timing was extremely fortuitous for us both.

We’ve lived a lifetime in this past year – time moves differently in lockdown, yeah, but we’ve also been lucky to cram in so much as a family: we “closed up shop” in New York, we quarantined in the Catskills, we drove across the country for the first time (albeit in record time with as few touch points as possible), and we posted up in Southern California. The time away from work allowed us to be present with one another and with our son. I think Miles (our dog) would agree that our bond is stronger than ever.

I don’t know what this next year has in store – none of us do anymore. But, in the meantime, I’m going to continue to pack in as much as I can before my thirties are up.

A New New Thing

It was an early December morning and I had just dropped my wife and son off at JFK. As I watched them pass through the security line, I had a small sense of freedom for the first time in the year since Crosby was born. I decided I would visit the new TWA Hotel and sat alone for breakfast at the bar while finishing the last few pages of Michael Lewis’ The New New Thing. I then decided I wanted a new new thing.

The name of the book itself is enough to inspire one to seek something new, but it was the story of Jim Clark’s lifelong pursuit of innovation that helped light a new fire. His obsessive nature of creating, tweaking, tinkering, both on personal and professional projects is something I’ve always seen in myself – a restless desire to innovate, create, push new ideas forward.

So, I am branching out on my own to start something new.

It’s a hard decision to leave the perfect role in a great company at Expa. When Garrett and I met up six years ago, we sought to create a different kind of startup studio, one that would be the best place for entrepreneurs to bring ideas to life. Now with our six Partners, I’m proud to say that we have accomplished that. We’ve had the honor to work with almost forty teams so far, and nearly 300 colleagues across all of our businesses. I have been more directly involved in helping to build a few of these including Current, Kit, Drip, Reserve, and Input.

Being a Partner at Expa has allowed me to live in all worlds of our industry: to be a founder, CEO, investor, board member, advisor, designer, coder, and educator. I am interested in and take great joy in this breadth of roles. I’ve always sought to be a kind of Renaissance man, a polymath, as one used to be called. But I am an engineer at heart and by training, and the role of the entrepreneur is always where I’ve felt most at home.

Though I am leaving Expa as a Partner, I will continue to be a part of the Expa network, helping our various teams and remaining on the board of Current. Thank you to my partners Garrett, Roberto, Vitor, Hooman, Milun and the rest of the Expa crew for an amazing six years and for supporting my next steps.

But now on to my new new thing. Though it is yet undefined, I would like to eventually start another great company, and will be tweaking and tinkering on personal and professional projects until I get there. While I explore new ideas, I’ll be hanging out at various friends’ offices in the city. And, to honor my wife’s long-term desire to return to LA, I’ll be spending a little time out West to see what might come up.

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Every year that goes by seems to be not only moving faster than the one before it, but packed with larger and larger milestones: meeting Diana, adopting our pup Miles, marriage, house moves, career wins, career losses, sometimes a couple of those things thrown into the same year. (And, in the case of marriage, we threw three weddings in the same year, because why not celebrate ourselves a little?)

This past year, keeping with the accelerating slope, has been the most action-packed yet. It was the one where I learned to become a dad. Me, teaching him all the things I know about the world. Him, showing me what it’s like to learn about life for the first time––a beginner’s mind in its purest form. Me, learning to up my dad joke game. (Truly, having a child is the sign of a groan man.) Him, testing his boundaries and exploring what he’s capable of, and oftentimes, making us laugh out loud in the process.

At last year’s birthday, I was too caught up in the thick of taking care of a newborn to think about what it means to be a dad. At this time last year, I spent most days with Crosby napping on my chest, dreaming of all the activities that I would do with him. This year, I’m doing a lot of those same things dreamt because he’s older, walking, and eager to discover the world around him.

With my wife having more free time away from work for the first time in a long time, and Crosby beginning to really interact with his surroundings, I think this year will mean more time exploring New York and seeing the world around us anew. One cold winter morning, as we were strolling the west side of Manhattan with newly-arrived Baby, my wife (who, let it be known, has long been seeking warmer climes than our brutal New York Januarys) said: “This will mean we’ll get to explore New York all over again.” So, knowing we will move at some point to who-knows-where as our family grows, let’s start with what’s there now in front of us: let’s explore New York all over again.

This past year has been spent trying to figure out how to stop chasing things endlessly – in work, in accolades, in likes, in what others have that I also want but that maybe I can’t quite explain why I want. To be confident in knowing that whatever comes, will come. Some of it was spent thinking “Well, now that we have all this family and kid stuff to work out, we won’t have time for anything else”. Now that we’re chasing Baby, how will we have time to chase anything else? And why, when all Baby wants and needs is us, do we want, or need to chase anything else? But in the past year I’ve learned to view all that time away from the “other chase” as a superpower of sorts. After Baby, I feel I know more now about life and other things I wouldn’t otherwise have. There’s some feeling like I’ve always known these things, but now I know these things. I seek closer, fewer, more meaningful friendships. I seek out books and places that I didn’t before, that give me experience and meaning without wasting time that I could otherwise be spending with family. I’m more mature now. I think of ideas and life differently now. I’d like to think I’ve always treated everyone as I would like to be treated, but I think I’m even nicer to everyone now, especially when I see other parents. A silent “Baby on Board” network no matter where we go.

This past year, I chose to spend most of my time with Crosby and Diana. You won’t get this time back. Time only goes one way.

At thirty-eight, I’m not just thinking of what I’ve done (or not done) in thirty-eight years, but what life will be like when Crosby is thirty-eight. And that, like my own life and my own thirty-eight years, it will all move just too fast. We won’t get this time back. It only goes one way.

This coming year, instead of just measuring age and accolades, I plan to use a different sort of measurement for my life. One that encompasses family, happiness, health, and success alike. I’m reminded of Clayton Christensen’s, How will you measure your life?

In pondering that question, I realized that my success lies not in just what I will achieve in my lifetime, but what my son will achieve in his.

Super wicked stories about a warming planet

After seeing a few people recommend it at year-end, I read The Uninhabitable Earth this weekend. Beyond wanting to learn about the things I didn’t know about carbon emissions and the feedback loop, I was seeking a better way to understand the state of the world we’re in today, and what we can still do about it. (Hint: beyond just acting now, because every day or year that goes by it becomes a bigger problem for us to solve, it’s to elect better politicians and to build more-efficient carbon capture plants and nuclear power plants and move us off of fossil fuels).

One can barely put the book down, because besides feeling a bit of panic as you read it, you think, “why isn’t this constantly in the back of everyone’s minds all the time?” Is it that I’m thinking more about it because of Baby and because I wonder what world we’re leaving for him between now and the 2100s? Is it because there isn’t a clear thing one single individual can do or even know what to do? I’m reminded of a Simpsons episode, where Homer and Marge are having an argument about something which he can clearly solve, but he just asks “What can I do? I’m only one man.”

Above all, one particular part stood out to me most: why is it so hard to tell the story of climate change?

Others call it “cli-fi”: genre fiction sounding environmental alarm, didactic adventure stories, often preachy in their politics. Ghosh has something else in mind: the great climate novel. “Consider, for example, the stories that congeal around questions like, ‘Where were you when the Berlin Wall fell?’ or ‘Where were you on 9/11?’ ” he writes. “Will it ever be possible to ask, in the same vein, ‘Where were you at 400 ppm?’ or ‘Where were you when the Larsen B ice shelf broke up?’ ”

His answer: Probably not, because the dilemmas and dramas of climate change are simply incompatible with the kinds of stories we tell ourselves about ourselves, especially in conventional novels, which tend to end with uplift and hope and to emphasize the journey of an individual conscience rather than the miasma of social fate. This is a narrow definition of the novel, but almost everything about our broader narrative culture suggests that climate change is a major mismatch of a subject for all the tools we have at hand. Ghosh’s question applies even to comic-book movies that might theoretically illustrate global warming: Who would the heroes be? And what would they be doing? The puzzle probably helps explain why so many pop entertainments that do try to tackle climate change, from The Day After Tomorrow on, are so corny and pedantic: collective action is, dramatically, a snore.

The problem is even more acute in gaming, which is poised to join or even supplant novels and movies and television, and which is built, as a narrative genre, even more obsessively around the imperatives of the protagonist—i.e., you. It also promises at least a simulation of agency. That could grow more comforting in the coming years, assuming we continue to proceed, zombie-like ourselves, down a path to ruin. Already, the world’s most popular game, Fortnite, invites players into a competition for scarce resources during an extreme weather event—as though you yourself might conquer and totally resolve the issue.

As Harari wrote, telling stories and believing in myths are what gave us a lot of the social constructs we have now. It is one of the things that not only separated us from the animals, but also brought us closer together as humans and achieved large-scale human cooperation – from tribes to farming to churches to cities. Sure, we have disaster movies, and books like The Uninhabitable Earth and leaders like Al Gore making it easier for all to understand. But all of those just seem…so far away…there’s always bad stuff going on in the world, and there always has been. Not only do they seem like, “What can I do? I’m only one man”, but there’s no way to wrap the story around one’s head. There are no heroes, there are no clear villains, there is no “we will randomly discover some pathogens that will destroy the attacking Martians immediately”.

Telling this story requires a different way to tell a story – beyond just your usual structures like the hero’s journey. As Wallace-Wells writes, we need an alternative: many problems we face now aren’t just one person’s problems where they go out into the world, selfishly solve it for themselves and come back home victorious. Most big problems are hard to define and hard to tell stories about. Global climate change, in particular, is known as a super wicked problem. We just may need some super wicked stories.

AirPods Pro

I got a pair of AirPods Pro as a holiday gift. Unlike previous versions, these have been the first ones to properly fit my ears, especially given the old ones were hard shell only. So, these are the first pair of Apple AirPods I’ve ever owned!

The call quality and noise cancellation are great. I hardly ever have to worry whether the person on the other end can hear me. And, on the go, working in various spaces these days, it’s far better to carry one pair of headphones that can swap seamlessly between iPhone and MacBook. (The Jabras only work on your phone, and not on your computer for some reason).

I still use my Jabra Elite Sport when I walk the dog, because even though the AirPods fit better, I still don’t trust them to stay in during the fast walks we do. The Elite Sport is made for exercise and running and they stay in no matter how much you’re moving around or how much you sweat (probably within reason). I find the Jabras are also better when used in a single ear – the noise cancellation on them when in one-ear mode is just that much better. I prefer to walk the streets of the city like this, as opposed to completely oblivious, because it’s easier to keep your dog and yourself safer that way. Depending on what you do, where you might use them, whether you listen to music while you workout, I would still highly recommend the Jabras to others.

One thing I’ve been wondering: will one ever be able to get custom silicone tips for the AirPods that are form-fit to your ears so that they fit even better than the standard S/M/L tips? For instance, I’m fairly sure my right is shaped differently than the left, because the right always keeps falling out. Given that you can swap the soft tips, it only makes sense that there exists some small market for custom in-ears. There is a custom attach point – see the iFixit teardown of the AirPods Pro – so not trivial for just about anyone to make replacements here, but if there ever was a custom option, I’d be first to get them.

The queen is gone, but she’s not forgotten

My wife Diana closed up her business after a beautiful ten-year run making the best ice cream in the world at MilkMade.

Since she announced she was shutting, I have also loved seeing all the ways in which she touched families, kids and was a part of so many lives in so many ways. From the long lines to people taking pilgrimages from far-off places to “MilkMade Mondays” to “I dreamed of my kids coming here; no point anymore of having any.”

I’ve never seen anyone work harder at their craft than she did. I got a front-row seat to seeing all the ups-and-downs of being a food business entrepreneur in New York City. The stories she could (and will) write someday!

I just made our latest batch of toasted hay ice cream. Yes, hay. Like for horses. Called Haunted Hayride, it is a toasted hay ice cream with gingersnap cookies and it is phenomenal. It has a naturally sweet and nutty taste which is perfectly complemented by the biting ginger and molasses of a gingersnap cookie. You must come and try it.

Toasted hay is perhaps my favorite flavor to make but also one that I dread the most. It’s inventive, it’s surprisingly delightful, and it’s fun to make. But it is such a process. It’s annoying, it’s time consuming, and it can be painful to make. It involves washing, sanitizing, and toasting small bundles of hay at a time. Then steeping and straining and hand-wringing cream out of the hay by the handful. It is, in the truest sense, a labor of love. And I do love it. But this was the last batch of hay ice cream that I’m going to make. Ever! Because MilkMade is closing.

Our shop will close on Sunday, November 3. Members of our ice cream subscription will receive our very last pints the following week, marking ten years since MilkMade’s launch in 2009. 

MilkMade – A farewell note from Diana


As part of a series called superorganizers, entrepreneur Dan Shipper has been talking to people about how they do their best work. Last week, I sat down with him to talk about the tools I use to track, capture and organize things in my life. You’ve heard me talk before about self-tracking and the Quantified Self, my personal API and my love for Asana. But we also got into something I do that I haven’t shared before: keeping a commonplace book.

In the interest of personally capturing it, I’ve put the whole interview here on my blog as well.


Welcome to another issue of superorganizers! We explore how the smartest people in the world organize what they know to do their best work.

If you’re not a subscriber, you can get more interviews like this in your inbox by clicking here.

Naveen keeps track. 

For a while, he had a personal API project where anyone could access basic stats about him like how many hours he slept at night, and how much he weighed in the morning. 

For over a decade, he’s been recording quotes, and images, blog posts, and articles in a digital commonplace so he can always find them later if he needs them. 

He even tracks his family life: recording everything from packing lists, to gift ideas, to potential family outings in an Asana he shares with his wife.

But this theme of tracking extends far beyond his personal life, it also extends to his life’s work.

In 2009 he co-founded Foursquare, the original location-based social network that allowed users to track places they visited. It’s now a $100mm a year behemoth with more than 300 employees. 

In 2015, he launched Kit to allow creatives to keep track of their favorite products, and sold it to Patreon

Now a partner at startup-studio Expa, he’s a peripatetic entrepreneur, hanging out at friends’ offices while he looks for his next thing. (He keeps track of that too, logging people and meetings in a personal CRM he’s created in his Asana.)

He’s cool, in a subtle and compelling way. He speaks softly and carefully, curating sentences like every thought could be permanent. 

Because for someone who tracks things like Naveen, in a way, they are.

We sat down to chat about this theme of tracking in his life, and explore the systems he uses to start companies, and manage his family life.  

In this interview we cover:

– How he uses tracking to set and adhere to goals

– How he keeps a digital commonplace to record things that inspire him

– How he uses his Apple Watch to keep fit, and Streaks to keep his habits up

– What he does when he falls off the wagon

– How he balances his commitment to his family with his work 

– His addiction to Asana to help him plan his personal life and his work life

– The personal CRM he’s built to help him find his next project

Let’s dive in!

Naveen introduces himself

My name is Naveen. I’m an entrepreneur that has started a few companies in the past, including company called Foursquare. Presently I’m a partner in a startup studio called Expa.

I’ve been working in the tech world for almost 20 years now, starting with a couple of big companies way back in the past, like Lucent and Sun before I got into startups. 

When he started tracking things about his life

A lot of these concepts started way back in college, for me, with tracking books. 

Basically, I realized I wasn’t reading enough. I wanted to read more, and I wanted more diversity in my information diet. So I set a goal that I wanted to read 10,000 pages in a year. 

Back then I was just crudely tracking everything in Excel. And I just kept a log of books that I read, interesting passages, even ratings for the books. 

Doing this type of tracking helped me understand how I was doing relative to that goal. So that’s what was valuable about it for me.

But it’s not just about being goal-oriented, there’s another motivation too. I came up in a time when everything was digital, you know. And if everything is digital, and storage is nearly free, and cameras are making it easier to capture everything — I thought, why not just capture everything? It might be useful in the future; you never know. 

So that’s what I started to do. I even kept an archive of my old emails and stuff. Before Gmail existed, our email existed on various servers, and I would just download and keep it because you never know when you’re going to need it or want to look back on it.

He uses a digital commonplace book to keep track of what he reads

I use a commonplace book to keep track of interesting things I come across. It’s an idea that has been around for centuries now. 

My commonplace book is a private WordPress blog just for myself. And that’s where I’ve been capturing snippets of things: quotes, PDFs that are interesting that I might read, a sign that I saw somewhere that’s interesting but wouldn’t post to Instagram, things that I might have heard at work, you know. All that’s got to go somewhere. So I capture it in my commonplace. 

It’s got a live URL, but I don’t share it. I’m not sure how to deal with it. I’ve been asking myself, Should I share it? Should I not? So I’ve just kind of kept it private for now. Someday I might do something with it.

But it’s basically a very simple WordPress blog. I don’t need it to be fancy, right? There’s nothing complicated that needs to go here. I kind of want to redesign the theme a little bit so that actually see the tags and or search on the right side. But for now I just want to capture. 

This is a poem that my wife actually found. She read it at her friend’s wedding this past weekend. This Indian poet, Rabindranath Tagore, wrote it, and it’s definitely shot to top ten best poems on my list. I was like, “How have I not heard this before?” So if I find something like that, I have to keep it.

The beauty of WordPress is that you don’t have to overthink it. It’s open source. They’ve been around for 16 years, they’re probably going to be around for another 16 years. 

Whenever I use a tool like this I’m asking myself, are they going to be around? Is the datacenter going to be around? What is the data format? Who else is seeing my data?

I know WordPress is probably overkill for what I’m trying to do here. But it works. So why overthink it? 

He uses Pinboard as a link-based commonplace

The other thing I’ve been doing along those lines is collecting links into a central place. 

I’ve been doing this for a long time, since 2005. I started with, but right now I use Pinboard. It’s my link-based commonplace. It’s just an easy enough way to log whatever I come across.

I even have it set up to actually auto capture links from my Twitter as well. So anything I tweet or capture snippets of on Twitter automatically gets captured here. 

So using Pinboard I can go back to all of these old areas of my life, and see them. 

I used to work at a startup that got acquired by Sony way back in the day. So I can go back can see all the projects I worked on, interviews I did, the patent we had back then in 2005. All this stuff is just logged here going way, way, way back.

Part of the reason to use it is, you know, we’ve been on the web for what, 25-30 years, right? How many of the URLs that were around 10 years ago are still around? There are so many great sites from the past are just gone. Where are they now?

So Pinboard is my solution to that because it actually saves a snippet of the web page for me. So even if the original page goes away, I can still find it.

He collects startup knowledge into a playbook

The other thing I do is I have a playbook of startup knowledge that I collect. 

Some of that is actually public on Pinboard. So, you know, anything I learn about entrepreneurship, building startups, VC stuff, essays or anything that other people have written, actually go here. 

So if you actually go to the tag, playbook, you can see everything I’ve saved about startups.

I’ve been thinking about making the rest of it public, so you can see everything in my commonplace that’s playbook related. But I haven’t gotten around to it yet.

On what he goes back to look at

I keep a lot of quotes in here that are things I’ve heard from people I know. It’s not just famous people, it could be advice that was given in a particular moment that was said in just the right way. Sometimes you’re having a difficult moment, and there’s a one-liner that really stands out. Those things are captured here, and sometimes I’ll go back and look at quotes like that.

One of my most favorite things that someone said to me a long time ago, “Write your own story before someone else does.” A friend of a friend said it, and it’s something that I’ve gone back and looked at, and even shared with other people. 

So having it captured in my commonplace helps me make sure that I don’t forget it, and helps me go back and look at it when I need to, or share it with someone else if I want to. 

How he uses the Apple Watch to encourage his fitness

One thing I do is just close my rings on the Apple Watch. Really simple. I got it, I think, a week or two after we had our son. You don’t get a chance to do much except stay at home to take care of the baby, so I got really into closing the rings every day, or trying to. 

I think it just makes it fun and it just sends you light reminders towards the end of the day. I’ll be about to go walk the dog, and it says, “Hey, you have 150 calories to go. Just go on a fast walk with the dog and you’ll close the ring.” And that’s really helpful for me to stay on track.

It’s also just helpful now that we have a baby, because I can do things without a laptop or a phone. Often, I’m holding the baby so I can’t get to the phone. Or I don’t want him to see the phone, because I’m very conscious about being around the screen when he’s there in the room. And the Watch makes that much easier to do.

He uses Streaks to help him build habits

Another app I’ve loved more recently is called Streaks. I think I heard about it from Justin Kan

Streaks helps me keep habits. So it’s helpful for my wife and me because we’ve been trying to keep to a vegetarian diet, and trying not to drink. I’ve also been trying to floss and read books every day. The goals I’m focusing on change every few months, and Streaks just provides a simple checklist at the end of the day to make sure I’m on track.

It’s helpful because you just go in the app and check it off, and it records how many days in a row you’ve done the habit. And it does the same thing as the Apple Watch where, at the end of the day, it says “Hey, did you floss your teeth? Did you read 15 minutes today?” And it helps keep me on track.

It costs $5 in the App Store, and it’s so beautifully designed. Totally worth it. 

What he does when he falls off

I drop off all the time. I think the key is to just not let it stress you out too much. It’s going to happen. You can’t always be super perfect. 

Just make sure to get back on the next possible day. Otherwise you’re just overthinking everything. 

I think I’m leaning more on the routine now than ever before. I’ve always been kind of an early morning, get up, get into the groove, get the day going kind of person. Then we got a dog and you have to be even more disciplined. And then we had a baby, and you have to be even more disciplined with your time. 

It feels like, okay, we only have 24 hours, right? Everyone else needs your time. So you have to have a routine. But within that routine you’re like, okay, I forgot to eat vegetarian today. Okay, great. No big deal. Just start over again. 

I think it’s important to have a routine. But I think if you’re too strict, then you’re just not having fun, right? 

How having a family affects his priorities

After I got married, got a dog, and had a kid, I felt simultaneously like, Oh my god I don’t have any more time left. But also at the same time weirdly, I was like, wait a minute, what was I doing before? 

You realize that you wasted so much time before. And now I’ve filled my life with all this love. Now I have less time, but I’m like, wow, we have a unit. 

We have our own family of four. A wolf pack of four. There’s something great about it. It’s weird, I can be in both mindsets: oh my god, I just don’t have enough time to get work done or, you know, clean the house. 

But at the same time, have this feeling of, this is just glorious.

There’s really so much time. 24 hours really is a lot of time to get things done if you use it right.

Why he picked Asana for todos and task management

I am a huge fan of Asana. A lot of people probably use Asana in a work context, but I started using it first actually in a personal context, and then I started having my teams work with it.

I use it because I think it will stick around forever, you know. The idea that our todos are going to go away when a company shuts down; that’s weird. 

Asana feels like a solid choice because it’s built by an ex-Facebook team led by Dustin Moskovitz and they have enough money that they’re going to be around for a long time. They’re going to build it in the right way. So I have more than enough confidence and trust to put everything in there. So that’s why I chose it in the first place and now I’m really addicted. 

It’s also great because I can use one tool. If I think of something right now, I just launch one app. And then I say, is this for work or is it for personal, or is it for something else? It all goes in the same app. So that’s why I really love it. 

I use it with my wife, and we have a project for the baby, and we have a project that’s for us. We use it to help keep track of all the things that we need to share, and talk about, and do. 

So when I’m on the go, whatever I’m doing, I just go here and boom, boom I can input whatever the todo is. Then later on, I can catalog it into projects and teams. 

He uses Asana to organize his personal life

DIESEL is a codename we have for our family. So DIESEL has a board, and anything related to the family goes in here. 

Anything from, we have to get flu shots to we have to buy gifts for our friends and family.

We also have a board for the baby. So, if we think of any interesting ideas they’ll go in here for review later. 

For example, here’s a great idea: there’s a holiday train show at the Bronx Botanical garden that we might want to go to – someone told us about this in passing. So we just log it in the baby project in Asana and then when the time comes we can come back and go see it.

It’s gotten to the point in my addiction to Asana that when we go away on a trip, I’ll actually create a project for the trip. Sounds crazy. But it’s a checklist of like, “Make sure you bring these 17 things for the baby.” Because if we miss one, life is going to be a bit harder on the road.

My friend Eric Friedman actually equated leaving the house with a baby to be almost like going to space: you have to bring all the backups, you have to bring your own oxygen, and you have to bring the duct tape.

And so I have it all saved as a template, so I don’t have to type it every time. I’ll clone the template for each trip and then make some modifications depending on where we’re going. 

And it’s so useful because, you know, I’m going away at the end of the week and I don’t want to wake up on a Thursday morning at 7am and try to remember everything. This helps me make sure you don’t forget anything. 

It’s like that scene in Home Alone where she leaves Kevin at home. And then she’s in the air and she realizes she forgot him: “KEVIN!!

That’s what this helps me avoid. 

Using Asana to find his next project

I’m actually in between ideas right now looking for the next interesting thing to build. And we don’t have an office for a couple months while we’re moving into a new space. So I’m using this time to just wander in different neighborhoods, get into collisions with other people, get excited about new ideas. 

So what I’ve been doing is I actually created this Asana project called, Pipeline Next. It’s an extension of my Asana CRM, nicknamed Pipeline, of great people I know or want to meet. 

So these are about a hundred or so people that I’m either touching base with, or getting intros to, and just jamming on ideas with.

And Asana is good for this because it’s not overkill. I can put everything in here, and just keep it simple. It’s not a perfect CRM replacement, but it does the job of tracking, which is all I need.

Using systems to respond appropriately under stress or time crunch

I think I started writing stuff down because I knew I was going to forget.

And the busier you are at work or the more stressed you are the more important this is. I’ve definitely been in moments where the amount of stress is so crazy that you don’t even remember what you talked about an hour ago. So I think these are habits that I picked up in moments like that. 

The second thing is I’m now a head of household – the team lead.

The dog isn’t going to pack his own stuff. Someone else has to do it. And knowing that I don’t have a good memory or I can be stressed in that moment, and I’m going to forget something, these are systems to help prevent that. And prevent the additional headache that comes with it.

At the end of the day you do forget stuff anyway, and that’s okay. I’m sure almost every trip I’ve forgotten something. This is not foolproof. But with a system you probably forget, you know, half as many things instead of all of them.

I got inspired by one of my favorite short books, the Checklist Manifesto. And it just reminds you that whatever you’re doing, whether it’s packing for a trip, or flying a plane, or preparing for surgery, these basic little systems can help. Make a checklist to make sure you’re doing the right things in the right order. 

Using iBooks to save PDFs

Recently, I started using iBooks to save PDFs. Just decks or research papers. I realized that there’s no good, easy tool for saving and browsing PDFs. There are a couple of crude open-source tools out there, but I’ve found that iBooks captures everything that I’d want to refer back to and has pretty good search – and works on mobile. 

For example, this is an article by Gay Talese at the New York Times about one of the first dog walkers. It’s this guy Jim Buck who used to walk dogs in New York City back in the day. Look at him, dressed all nice.

I wanted to send this to my dog walker, and so I pulled the PDF. Then I saved it here. 

And I have it now because this is going to be hard to find in the future, I think. So now I have it locally on my computer, and I can always find it easily.

The things that Google doesn’t see

I have a concept that I like to call ‘The things that Google doesn’t see’. Companies like Google and Facebook, they’re seeing all of the things we’re posting on social media, the stuff we’re posting on our blog, stuff that we’re getting out in to the world. 

And they make all of this stuff searchable, it’s already out there. But I think a lot about the things Google doesn’t see. For example, it doesn’t see my commonplace book.

But what would happen if we made all of that stuff searchable? 

One tool that’s starting to do this is called FYI. It’s built by Hiten Shah, and I love, love, the stuff that Hiten does. 

It lets you search through all of your cloud files like, Drive, and Dropbox, and Evernote with just one tool. But what I particularly love about it is that they’ve built into the new tab flow of Chrome. 

So every time I open a new tab, I can instantly search through all of my files without having to click anything. It’s very convenient.

Picking simple tools

Basically, my philosophy on everything I use is to pick the simplest, easiest, tool for the job. It’s sort of like, “the best camera is the one you have with you.”

You could spend forever and ever thinking about how to optimize to the right feature-set and this and that. But at the end of the day, you don’t even know if the tool is going to stick around. You don’t know who’s going to update it.

That’s why I’ve said, for the most part, “Okay, let’s not over think this. We don’t need to use any fancy tools. Let’s just use Pinboard. Let’s just use WordPress. Let’s just use Asana. 

They each have a lot of features I won’t use, but that also means I won’t be reaching to find a particular feature when I need it most.” 

Book Recommendation: The Whole Earth Catalog

One of my favorite books actually is not really something I would recommend you sit down and read end to end, but it’s still great. It’s the Whole Earth Catalog

If you go back and do the research, it’s amazing how many people it’s touched and inspired. It inspired Kevin Kelly to go do the stuff you see with Wired Magazine, and then inspired him to go do his project called Cool Tools (which also became a large printed book in a style similar to the Whole Earth Catalog). 

And of course, it inspired Steve Jobs. That line from his commencement speech, “Stay hungry; stay foolish,” came from the last page of the 1974 Whole Earth Catalog.

More broadly, it just touched a lot of people in the Valley. It captures California culture, it captures tech. We needed those types of minds, and that type of craziness. 

And it’s called the Whole Earth Catalog because when it was published in the late 60s, it was during the time when we first went to space. That’s the first time we actually looked at the Earth in its totality with our own eyes.

So it’s this idea that there’s only one Earth. We have to take care of it.

So that’s what’s interesting to me about it.


What I’m reading

A few reads for your weekend.

The One Device [book]

The story of the iPhone and how it came to be and a story that is two decades in the making. The retirement of Ive from Apple earlier this year marked a turning point: he was the last executive from the original iPhone team to leave the firm.

Insta Novels

In August 2018, Instagram followers of the New York Public Library were tapping through their Insta Stories when something unexpected showed up: the full text of Alice’s Adventures in Wonderland, designed for a small screen, with small animations that brought the story to life as you flipped.

“Anywhere people want to read is fine by us,” says Richert Schnorr, the director of digital media at the NYPL. “We’re happy to meet people where they are.”

Four Years in Startups

San Francisco was tipping into a full-blown housing crisis. Real-estate brochures offered building owners enticements to flip. “Hi, neighbor!” they chirped. “We have considered and ready buyers eager to invest in your neighborhood.” There was a lot of discussion, particularly among the entrepreneurial class, about city-building. Everyone was reading “The Power Broker”—or, at least, reading summaries of it. Armchair urbanists blogged about Jane Jacobs and discovered Haussmann and Le Corbusier. They fantasized about special economic zones. An augmented-reality engineer proposed a design to combat homelessness which looked strikingly like doghouses. Multiple startups raised money to build communal living spaces in neighborhoods where people were getting evicted for living in communal living spaces.

There was a running joke that the tech industry was simply reinventing commodities and services that had long existed. Cities everywhere were absorbing these first-principles experiments. An online-only retailer of eyeglasses found that shoppers appreciated getting their eyes checked; a startup selling luxury stationary bicycles found that its customers liked to cycle alongside other people. The online superstore opened a bookstore, the shelves adorned with printed customer reviews and data-driven signage: “Highly rated: 4.8 stars & above.” Stores like these shared a certain ephemerality, a certain snap-to-grid style. They seemed to emerge overnight: white walls and rounded fonts and bleacher seating, matte simulacra of a world they had replaced.

Software margins

If the product is software and thus can produce software gross margins (75% or greater), then it should be valued as a software company.

If the product is something else and cannot produce software gross margins then it needs to be valued like other similar businesses with similar margins, but maybe at some premium to recognize the leverage it can get through software.

Navigating NYC schools

The mood of meritocracy is anxiety—the low-grade panic when you show up a few minutes late and all the seats are taken. New York City, with its dense population, stratified social ladder, and general pushiness, holds a fun-house mirror up to meritocracy. Only New York would force me to wake up early one Saturday morning in February, put on my parka and wool hat, and walk half a mile in the predawn darkness to register our son, then just 17 months old, for nursery school. I arrived to find myself, at best, the 30th person in a line that led from the locked front door of the school up the sidewalk. Registration was still two hours off, and places would be awarded on a first-come, first-served basis. At the front of the line, parents were lying in sleeping bags. They had spent the night outside.

I stood waiting in the cold with a strange mix of feelings. I hated the hypercompetitive parents who made everyone’s life more tense. I feared that I’d cheated our son of a slot by not rising until the selfish hour of 5:30. And I worried that we were all bound together in a mad, heroic project that we could neither escape nor understand, driven by supreme devotion to our own child’s future. All for a nursery school called Huggs.

Apple Maps’ expansion

Beautifully tracked progress of Maps’ latest updates in the U.S.

Working [Caro’s latest; excerpt]

I will never forget that night. It was the first time I had ever gone through files. The official met me at the front door and led me to a room with a conference table in the middle, and, on the table, high stacks of file folders. And somehow, in a strange way, sitting there going through them, I felt at home. As I went through the memos and the letters and the minutes of meetings, I could see a pattern emerging, revealing the real reason that the agency wanted the field to become a civilian airport: executives of corporations with offices on Long Island, who seemed to be quite friendly with the F.A.A. officials, wanted to be able to fly in and out of Long Island on their company planes without the inconvenience of having to drive to Idlewild or LaGuardia. I kept looking for a piece of paper on which someone came right out and said that, but I didn’t find one; everything I could find talked around that point. But between all the pieces of paper I found sentences and paragraphs that, taken together, made the point clear.

There are certain moments in your life when you suddenly understand something about yourself. I loved going through those files, making them yield their secrets to me. And here was a particular and fascinating secret: that corporate executives were persuading a government agency to save them some driving time at the expense of a poor kid getting an education and a better chance in life. Each discovery I made that helped to prove that was a thrill. I don’t know why raw files affect me that way. In part, perhaps, it’s because they are closer to reality, to genuineness—not filtered, cleaned up, through press releases or, years later, in books. I worked all night, but I didn’t notice the passing of time. When I finished and left the building on Sunday, the sun was coming up, and that was a surprise. I went back to the office, and before driving home I wrote a memo on what I had found.

Change of space, change of pace

After five years, I moved out of our SoHo office, 13 Crosby. There was a part of me that didn’t want to, but sometimes you have to shake things up a bit – get a change of pace and perspective. So, we’re going to take a bit of a break from a dedicated space and start exploring ideas in new ways.

As we got closer to the end of our lease, everyone, including me of course, went through their own rollercoaster of emotions. That’s what happens after five years of work in a home away from home. Colleagues, alumni, nearly everyone from our now extended network of 270 people (or so our Slack says) reached out to share an anecdote or something they loved and they’ll miss about it. One friend summarized it best: “That office touched and supported so many! Thank you for you and it supporting me on my own entrepreneurial journey.” No matter how you came through this space, it has no doubt helped shape some part of your work and your future.

We will get another space at some point soon, but in the meantime, I’m trying to get into the open-ended nature of remote work. I think the change of place, the bumping-into-people-in-new-neighborhoods, the serendipity will lead to big, new ideas.

I’ve been hopping between different startup offices. Ideally, I’d like to try to pick a spot that I can hang out in for a week or so (and set up meetings and all that around it for the week). In return, I’m going to try to help the startup there if I can and if it can also help inspire new ideas, then all the better. If you have a startup or founder I should hang with, hit me up! And yes, I’ll leave SoHo. 🙂

Above, an overhead shot of our office.