America, Interrupted


This post is by M.G. Siegler from 500ish - Medium

The end of Donald Trump. For now…

Photo by Luke Stackpoole on Unsplash

Yesterday was a fantastic day. A needed one. I fully believed in this outcome and even when things were looking dire to many, with flashbacks to 2016 illuminating left and right, I trusted the process and the process prevailed. After a year more brutal than any in memory, let’s celebrate this day and hope this is a turning point.

But I also want to be realistic and honest. And I think we all should in order to remain vigilant. Joe Biden got more votes than anyone in the history of our democracy — 75 million and counting — which is amazing. At the same time Donald Trump got the second most votes of anyone in the history of our democracy in losing. And I fear that if it were any other candidate other than Biden, who Trump-hating Republicans were comfortable voting for, Trump would have won again.

So if there’s a victory the Democrats should celebrate today, it’s that they made the right choice in picking a candidate. Everyone else who was in the running late would have been disastrous. And so let’s be very clear and again, honest: the Democrats didn’t win this election, Donald Trump lost it. The Democrats simply allowed him to do so.

70 million people voted for Trump. 70 million. 70 million. Say it a thousand more times. After what we’ve all been through the past four years, and especially the past year of complete and utter incompetence and buffoonery. Four years ago, I wondered if this country was going to have to learn a lesson the hard way in the election of Trump. And now you could argue that we’ve learned a few lessons in such a manner, but certainly COVID is top of mind as the key hard lesson, with so many lives lost.¹ And yet, looking at these results, it seems as if no lesson was learned at all.

The hope today is that the past four years of Trump has been a blip on the radar of our democracy. An interruption, a distraction, and now we’re back on track. The fear is that this election is the blip. And I don’t mean that in the sense that Republicans will win again — I sincerely hope that at some point in my life they put forward a candidate I’m excited about voting for — it’s that Trump or his literal ilk will be back. You can take it to the bank that they will try in 2024, the question is where America will be at that point.

And so I’d say to the Democrats celebrating this win today, look inward. Result at the top of the ticket aside, it’s clearly time to reboot the party, much as it is on the Republican side. We all need to make the most of these next four years. To make America great again, as it were.

I am so, so, so happy that my young daughter no longer has to grow up in a world where a morally corrupt con man is President of the United States. That’s what I keep thinking about today. And why I’m so thrilled with this outcome. I take solace in the fact that she won’t remember the shitshow that was the first couple years of her life. Now we need to make sure that the country going forward is worthy of her memories.

Photo by frank mckenna on Unsplash

¹ And while you certainly can’t blame Trump for COVID-19 itself, nor can you for the majority of lives lost, I believe you absolutely can blame him for some subset of lives lost, as America has performed badly below and beyond comparable countries. Is that number in the thousands? Tens of thousands? Hundreds of thousands? More? It’s impossible to know. But even if it’s just one. If just one life could have been saved if Trump and his administration had taken the virus and the response to it seriously, that would have been worth having a different president in office. Just to save one life. Obviously. This isn’t a statistic, it’s a life. And it was lost because Trump was incompetent. Or just didn’t give a shit. Or both. Or whatever. Good riddance.


America, Interrupted was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

America, Interrupted


This post is by M.G. Siegler from 500ish - Medium

The end of Donald Trump. For now…

Photo by Luke Stackpoole on Unsplash

Yesterday was a fantastic day. A needed one. I fully believed in this outcome and even when things were looking dire to many, with flashbacks to 2016 illuminating left and right, I trusted the process and the process prevailed. After a year more brutal than any in memory, let’s celebrate this day and hope this is a turning point.

But I also want to be realistic and honest. And I think we all should in order to remain vigilant. Joe Biden got more votes than anyone in the history of our democracy — 75 million and counting — which is amazing. At the same time Donald Trump got the second most votes of anyone in the history of our democracy in losing. And I fear that if it were any other candidate other than Biden, who Trump-hating Republicans were comfortable voting for, Trump would have won again.

So if there’s a victory the Democrats should celebrate today, it’s that they made the right choice in picking a candidate. Everyone else who was in the running late would have been disastrous. And so let’s be very clear and again, honest: the Democrats didn’t win this election, Donald Trump lost it. The Democrats simply allowed him to do so.

70 million people voted for Trump. 70 million. 70 million. Say it a thousand more times. After what we’ve all been through the past four years, and especially the past year of complete and utter incompetence and buffoonery. Four years ago, I wondered if this country was going to have to learn a lesson the hard way in the election of Trump. And now you could argue that we’ve learned a few lessons in such a manner, but certainly COVID is top of mind as the key hard lesson, with so many lives lost.¹ And yet, looking at these results, it seems as if no lesson was learned at all.

The hope today is that the past four years of Trump has been a blip on the radar of our democracy. An interruption, a distraction, and now we’re back on track. The fear is that this election is the blip. And I don’t mean that in the sense that Republicans will win again — I sincerely hope that at some point in my life they put forward a candidate I’m excited about voting for — it’s that Trump or his literal ilk will be back. You can take it to the bank that they will try in 2024, the question is where America will be at that point.

And so I’d say to the Democrats celebrating this win today, look inward. Result at the top of the ticket aside, it’s clearly time to reboot the party, much as it is on the Republican side. We all need to make the most of these next four years. To make America great again, as it were.

I am so, so, so happy that my young daughter no longer has to grow up in a world where a morally corrupt con man is President of the United States. That’s what I keep thinking about today. And why I’m so thrilled with this outcome. I take solace in the fact that she won’t remember the shitshow that was the first couple years of her life. Now we need to make sure that the country going forward is worthy of her memories.

Photo by frank mckenna on Unsplash

¹ And while you certainly can’t blame Trump for COVID-19 itself, nor can you for the majority of lives lost, I believe you absolutely can blame him for some subset of lives lost, as America has performed badly below and beyond comparable countries. Is that number in the thousands? Tens of thousands? Hundreds of thousands? More? It’s impossible to know. But even if it’s just one. If just one life could have been saved if Trump and his administration had taken the virus and the response to it seriously, that would have been worth having a different president in office. Just to save one life. Obviously. This isn’t a statistic, it’s a life. And it was lost because Trump was incompetent. Or just didn’t give a shit. Or both. Or whatever. Good riddance.


America, Interrupted was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

A November to Remember


This post is by M.G. Siegler from 500ish - Medium

Some thoughts on turning 39…

Photo by Tarik Haiga on Unsplash

As is the case with all of us who were born in early November, sometimes my birthday falls on Election Day.¹ I’m very glad it’s not on Election Day this year, but rather the day before, so I can reflect with somewhat of a clear mind. Well, as clear of a mind as anyone could possibly have in the utter chaos soup that has been 2020.

Today, I’m 39 years old. One day before an election. One year before 40.

Reading over my thoughts from a year ago now read like a totally different world. I used the word “quiet” and “still” over and over again. Can you imagine? For this past year, I would choose the exact opposite words. I referenced how we were supposed to be living in Blade Runner — and then the world quite literally started looking like Blade Runner.

In many ways, this past year has seemed a bit like a nightmare from which we can’t awaken. Certainly since COVID lockdowns started in March. And yet at the same time, it feels like it’s hard to complain too much since my family is healthy and relatively happy on a day-to-day basis. There are so many people who have it far, far worse. So I find myself thankful that this year has only been a nut kick and not a gunshot wound.

I don’t necessarily believe in karma, but I do believe in some level of equilibrium. And it just feels like the tide has to turn at some point on all of this. That the last year of my 30s can be remembered as a year where we stared down the endless abyss but were able to turn things back around. That we’ll all benefit from knowing what bad times look like and do what we can to make sure we never get back here.

It sure feels like that starts tomorrow.²

¹ It actually did in 1999, when I turned 18 years old. So I could vote the very day I was legally allowed to. Though it was the year before a crazy election. One which four years ago put to shame. And hopefully tomorrow does not.

² If you haven’t already, vote!


A November to Remember was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

A November to Remember


This post is by M.G. Siegler from 500ish - Medium

Some thoughts on turning 39…

Photo by Tarik Haiga on Unsplash

As is the case with all of us who were born in early November, sometimes my birthday falls on Election Day.¹ I’m very glad it’s not on Election Day this year, but rather the day before, so I can reflect with somewhat of a clear mind. Well, as clear of a mind as anyone could possibly have in the utter chaos soup that has been 2020.

Today, I’m 39 years old. One day before an election. One year before 40.

Reading over my thoughts from a year ago now read like a totally different world. I used the word “quiet” and “still” over and over again. Can you imagine? For this past year, I would choose the exact opposite words. I referenced how we were supposed to be living in Blade Runner — and then the world quite literally started looking like Blade Runner.

In many ways, this past year has seemed a bit like a nightmare from which we can’t awaken. Certainly since COVID lockdowns started in March. And yet at the same time, it feels like it’s hard to complain too much since my family is healthy and relatively happy on a day-to-day basis. There are so many people who have it far, far worse. So I find myself thankful that this year has only been a nut kick and not a gunshot wound.

I don’t necessarily believe in karma, but I do believe in some level of equilibrium. And it just feels like the tide has to turn at some point on all of this. That the last year of my 30s can be remembered as a year where we stared down the endless abyss but were able to turn things back around. That we’ll all benefit from knowing what bad times look like and do what we can to make sure we never get back here.

It sure feels like that starts tomorrow.²

¹ It actually did in 1999, when I turned 18 years old. So I could vote the very day I was legally allowed to. Though it was the year before a crazy election. One which four years ago put to shame. And hopefully tomorrow does not.

² If you haven’t already, vote!


A November to Remember was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

The Gold Rush for the Exits


This post is by M.G. Siegler from 500ish - Medium

It’s the end of California as we know it…

An actual picture I took a few weeks back amidst fire and smoke…

I’m writing this with the windows sealed in our home in San Francisco. The air purifiers are on full-blast. We now have six of them. The air quality hit 200 again today and is hovering around 150 right now. But it could be worse — much worse. We could be up north where the fires are actually burning down trees and homes and cutting down lives. Such is the state of California in 2020.

I moved to California 16 years ago. After a handful of years in the southern part of the state, I made my way up north to the Bay Area and found myself. I’ve thrived both personally and professionally here. I now have a family here. This is my home.

And yet here I am effectively preemptively writing the cliched “Why I’m Leaving San Francisco” Medium post, even though I’m unlikely to leave for at least a few years. But I think this will help me clarify my own thoughts and answer questions I get asked a lot these days.

You’ve undoubtedly heard the rumblings or read the trend pieces that some combination of San Francisco, the Bay Area, or California itself is over. These will continue. They are similar to the posts about New York being over, but have their own unique properties. The main one being that there is some amount of truth to the California varietal.

The thing is: our region isn’t “over” because of COVID, or homelessness, or taxes, or fires, or even the tech scene. But it is just the right combination of all of those things which is causing many to take a look inward and at their surroundings and to wonder if it’s not time for a change.

And if not now, when?

Six months in, COVID has obviously been a nightmare. A surreal one. But California, and the Bay Area in particular, has seemingly done a pretty decent job managing it (relatively speaking). And while the virus has put a spotlight on some of the problems with living in a city, this will all pass.

The pandemic has also highlighted the concept of remote work — a trend which was already underway thanks to newer tools like Slack and Zoom — and has now been forced upon all of us. But this too shall pass. Well, not exactly pass, but we’re already feeling a bit of pushback against the all-remote workforce. For some companies, it works. For others, they’re making it work. For most, it’s going to be a hybrid model when the dust settles. Many people in centralized offices, most of the time. But not all the time. And some employees and functions will be fully remote. New companies will be formed built this way from the ground up. A shift towards centralization will be hard (but necessary) for some. But not all.

The key is that this situation has highlighted to all of us that it is possible to work remotely. Perhaps it’s more effective in some ways and undoubtedly less so in others, but we can and have made it work. It will take a while once things are back to “normal” to find the right balance, but we will.

And again, part of that balance will be people not needing to be in the office, in the Bay Area, all the time. And for some roles and functions, perhaps not even most of the time. Or even any of the time.

At the same time, this sounds enticing to people because the Bay Area, and San Francisco in particular, is expensive.¹ This has more or less always been the case, but if it’s shown that you may not need to live here to work here, why would you? There are actually reasons, of course.² But they are less good reasons than they were six months ago.

And this is especially true now because our entire region — and really, state — is constantly under a literal cloud of smoke. Some of it is bad forest policy. Some of it is climate change. At the end of the day, when you’re sitting in your boiling hot San Francisco home with your windows sealed and air purifiers running to protect your family, does it really matter?

California seems sadly fucked in this regard. This is only going to get worse. And so per the above, why you would choose to live here if you didn’t have to is… well, now a real question! Again, for some people it will still make sense. For most, even, I imagine, for a while. But for some…

A lot also gets made of the fact that California has the highest income taxes in the country. This is both very true and very secondary. This has basically always been true, but the reality is that it used to make sense to pay such a fee to live here when all of the above issues were not true. Now that they are… you’re essentially paying a massive fee to work in the heart of the tech scene, but you can’t go to an office. And you’re paying to live in a beautiful place with the great outdoors at your doorstep, but you can’t go outside.

And even if you could, those high taxes are paying for… a whole range of befuddling and complicated municipal issues. Namely, an intense and sad homelessness issue. It’s entirely unclear what that looks like post-pandemic, but it’s hard to see a world in which it’s any better than it was. And there are many ways to see how it’s worse. Again, this is not new, nor is it alone a reason to leave, necessarily. But all of these things together…

Let me try to put it more succinctly. We live in a state that offers fantastic career and life opportunities. But the pandemic has negated many of those opportunities. They will be back, but it has also highlighted that many of those same opportunities are available elsewhere or remotely. At the same time, when not avoiding a virus, we have to avoid poisonous smoke or deadly fire on an ever-increasing basis. So when the pandemic is over and we can go out and about as we once did — we still probably won’t be able to at all times. And yet we pay a premium in terms of rent and mortgages and taxes to live here. Taxes which have yet to solve some of the very real and very sad issues within our cities.

I mean, I won’t go so far as to say it’s becoming a no-brainer to leave San Francisco or the Bay Area or California in general. But I won’t not go there either given a long enough time horizon.

If I had to predict what will happen, it’s this: the pandemic will be under control at some point next year. Around the same time, there will be a full-on backlash against work from home, and people will be ready and willing to go back to the office. And it will seem like a bounce back — but it will be more of a dead cat kind.

Many who moved and/or were hired remotely will stay working in that regard. New companies will start this way. And a hybrid model will become the norm. This will slowly but surely ease the strain on Silicon Valley. It will still be the “tech capital” of the world, but it will stop growing at such a rapid clip. Other hubs will become far stronger as a result. This is a natural and good thing and was already happening, but all of the above will accelerate it.

Meanwhile, the deceleration of the Bay Area flywheel will also make it easier for people to leave the region, thus eroding the foundation of “home”, causing others to question their commitment. And others to never come here in the first place. And the environmental issues will only further pump the breaks. And once again the gold rush will be over.

Photo by Shreyas Malavalli on Unsplash

¹ It is also, of course, expensive for companies to pay employees high enough salaries to be able to live in the Bay Area. The regional pay scale topic is already a bit of a thorny and complicated issue with people relocating during COVID, but it too will get sorted out with time.

² The travel-for-work element is also going to be fascinating to watch over the next few years. Presumably there will be more “internal” travel to get remote teams together in the same space from time-to-time. But there may well be less “external” travel as Zoom and the like have proven themselves invaluable (read: cost-saving) tools for meetings all around the world. Who needs to get on a plane, most of the time? We’re going to find out!


The Gold Rush for the Exits was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

What the Hell Just Happened?


This post is by M.G. Siegler from 500ish - Medium

Blogging in the time of COVID

Will Leitch, best known as a sports writer (founder of Deadspin, etc), has started writing on Medium with an interesting, and very different goal:

As I embark on this new Medium project, for which I’ll be writing regularly every week. I am trying to capture the madness of living through this moment: Not just the political fights, not just the idiots marching through Target, not just the whole American West on fire, not just everything we think we think about everything crumbling around us at every moment. It feels like we are at a pivot moment in history, and it affects every aspect of American life: Schools, churches, entertainment, car pools, grocery shopping, all of it. That’s what I am going to try — and likely fail, but I will still try — to capture. The day-to-day experience of surviving 2020 … and what we’ll tell our children about it. If there’s a world left for them to ask it in.

I think about this a lot as well. Our daughter is about to turn two. This past year has certainly been the most surreal of her young life because it has been the most surreal of my almost-39 year life. The difference, of course, is that she won’t remember any of it — well, one can only hope! Still, I imagine a not-too-distant future where we’ve escaped the clutches of COVID and she learns about it and asks about it. I’m not sure I’ll know where to start.

Documenting it in real time makes a lot of sense. In a way, this has always been what I’ve liked the most about having a blog: the ability to put down your thoughts to look back upon later. Oh, and it’s nice when people read such thoughts as well 🙂

I actually thought about this two years ago as well when our daughter was just about here. What if I wrote down my thoughts each day to document her early life? But that idea, as nice as it sounds, quickly got swept away in the tides of parenthood.¹ It’s hard enough to keep up with writing one blog, let alone several. So instead my ever-aspirational goal is to get back to writing daily where ever I can. And I think some of Medium’s new changes make it more likely than ever. Hence, posts like this one. Not everything has to be a polished gem of insight and analysis. Just thoughts.

Anyway, back to Leitch:

There is something about being in the middle of history that is uniquely disorienting. Watching Ken Burns’ and Lynn Novick’s epic “The Vietnam War” in 2017, it was staggering for me to imagine what it must have been like to be alive through the experience. I was born in October 1975, three months after North and South Vietnam officially unified. In the span of time between his high school graduation and my birth, my father joined the Air Force, watched close friends die, met my mother, married her during a weekend furlough from his base in Virginia, started a career as an electrician, bought a home, buried a son and then gained another. He did all this, of course, during one of the most tumultuous periods in American history. But every time I ask him what it was like live through all that, the protests, the civil rights movement, Watergate, man walking on the goddamned moon, he can never quite describe it. “I was too busy trying to figure out my own life and my own family,” he says. “I didn’t quite realize what was all happening until it was all over.”

I think in many ways we can only live through times like these by not stopping to think about them. It would be too much. And it often is. You put on blinders and keep going and then someday, when it’s over, you look back and say “what the hell just happened?” And posts like the ones Leitch is trying to write will help us remember what we’re trying so hard right now to forget. And you talk about those times, ideally over drinks with family and friends in person.

Photo by Egor Myznik on Unsplash

¹ Still, I do write her a weekly email about her life, which I send to an email account we set up to give her access to in the future.


What the Hell Just Happened? was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

Are You Spending Your Weeks The Way You Want To?


This post is by Valet from Feld Thoughts

Amy has a birthday coming up. We spent some time this morning talking about her next year. Since the two of us are together all day every day, we also discussed how I’m spending my time over the upcoming year that begins at her birthday.

A few hours later, I stumbled upon Your Life in Weeks on Wait But Why, one of my favorite blogs. The following are the number of weeks (measured in boxes) that a typical 90-year-old human has on this planet.

Think you have all 90 years worth of boxes? Here’s some perspective.

Don’t want to think in weeks? Ok, let’s scope it down to months.

When you look at it this way, there aren’t that many. Go back to the weeks. When you look at the upcoming week, are you happy about how you are spending your time? How about this month (yeah, we are almost halfway through September already.)

Fortunately, Tim (who writes Wait But Why) sells a handy-dandy Life Calendar (by weeks), so you can sit down and sketch your own out thoughts. I just bought several and expect I know what Amy and I will be doing together for some of next Saturday.

The post Are You Spending Your Weeks The Way You Want To? appeared first on Feld Thoughts.

‘Home’ Has Moved Away From Us


This post is by M.G. Siegler from 500ish - Medium

The rapid transformation of San Francisco

Where are we now?
I’ve got to let you know
A house doesn’t make a home
Don’t leave me here alone…

The above is a lyric from U2’s 2004 song “Sometimes You Can’t Make It On Your Own” which pops into my head from time to time. Tonight again, while reading Om Malik’s post about the feeling of being “home alone” in San Francisco during the pandemic, the most recent wild fires, and people seemingly just leaving in general. As he notes:

I didn’t think of San Francisco as Home at that point, but fast forward to today, unbeknown to me, it is home. This past week, three of my favorite neighbors have moved out. Another close friend has packed up and moved out of San Francisco. Slowly, I am starting to lose people and places that gave life some context. Life is the context friends, and places provide us.

Many of my favorite places are shutting down. Reality has a porous quality to it now. And like the ash falling from the sky, it is sprinkling a sense of loss. I wonder how many others feel this social disruption that is happening around us.

I definitely feel it. While the history of the city has seemingly been written, quite literally, by the “Why I’m Leaving San Francisco” posts, this time feels different. Perhaps that’s because it’s happening more acutely. But I also feel as if in my dozen+ years in San Francisco that I’ve seen a few of these waves. And again, this one just feels different.

And I think Om hits on why. It’s because we’re still here, but what has made San Francisco feel like home is in flux.

That is to say, “home” has moved away from us.

Part of it is the virus, part of it is the fires, part of it is the quality of life, part of it is the cost of living. But the bigger part is the ramification of all of these things: it’s driving people and their businesses away.

And so San Francisco truly does feel less like home on a near daily basis. I’m sure this is true in many other cities as well, but I happen to live in San Francisco. And I’m sure San Francisco will be back. But I’m also sure that it will be different. And I think that’s probably a good thing. But I’m also quite sure that it will no longer be home. Because a house doesn’t make a home.


‘Home’ Has Moved Away From Us was originally published in 500ish on Medium, where people are continuing the conversation by highlighting and responding to this story.

Why Being a Founder is the Most Challenging Thing You’ll Ever Do


This post is by Elizabeth van Rooyen from Startup Grind - Medium

And why seeing the big picture is the most important.

How to Thrive as a Remote Worker Amid Coronavirus Spread


This post is curated by Keith Teare. It was written by Vanalli. The original is [linked here]

The coronavirus pandemic means millions of office workers around the world may be forced to work from home — many for the first time. If working from home is something new, you may have concerns about how you’re going to cope. Will your creativity go out the window? Will productivity and collaboration suffer? Will you forget how to express empathy? Kevin Roose’s recent NYT article, Sorry, but Working From Home Is Overrated, may have filled you with dread, but I want to present an alternative view as someone who’s flourished as a remote worker for the past two years.

I initially wrote this as a Linkedin article, but have brought it up to date as remote work is being widely discussed at the moment.

There are pros and cons to working from home, but my hope is that after reading this article you’ll see there are enough pros to make the upcoming weeks or months bearable (and perhaps even a little fun).

Pro number 1? I don’t get dressed for work. I mean literally. I wake up at about 7.30am, walk downstairs in my pyjamas, open my laptop and start work. My mornings are normally filled with video calls and catchups with colleagues, all of which I take in my pyjamas (sometimes boxer shorts). My colleagues don’t know this, of course; to them it just looks like I’m wearing regular clothes with a T-shirt.

The takeaway here is that remote working is ideal for people who don’t want to wear trousers.

There’s more Continue reading “How to Thrive as a Remote Worker Amid Coronavirus Spread”

Passion Isn’t Enough


This post is curated by Keith Teare. It was written by Anthony Scott. The original is [linked here]

Photo by Ian Schneider on Unsplash

I’m not saying that being passionate is bad, but it certainly isn’t enough.

In fact, passion can sometimes be the very thing that is hindering you from accomplishing your goals.

“Well, is this something that you are passionate about?”

The notion of having to be passionate about the project that you are currently working on is short-minded. Although having some type of emotional investment in your work is beneficial to the work itself as well as your mental health, it is a double-edged sword.

I have watched “passion projects” crumble and bring adults to tears.

But first, we need to define ‘passion’.

In his book “Ego is the Enemy”, Ryan Holiday describes passion as “unbridled enthusiasm, our willingness to pounce on what’s in front of us with the full measure of zeal”. I’m defining passion in three words “motivation through emotion”.

Passion does not have a negative connotation and it shouldn’t.

The struggle that many of us deal with is passion become our main driver through a project. Therefore the phrase “follow your passion” has become a more frowned upon phrase.

It is setting you up to engage in an area, project or profession where you will one-track minded and predisposed to be illogical.

Passion is exhaustible.

We are constantly thinking.

Whether it is about our work, our relationships, or the new season of Bojack Horseman we watched last week. No matter how much we try to not multitask, we are switching where we give our attention Continue reading “Passion Isn’t Enough”

A Quiet Place

Some thoughts on turning 38…

It’s quiet. Too quiet. Honestly, too quiet. So quiet that it feels weird, quiet. So quiet that I’m distracted.¹

I’m writing this at one of our favorite places on Earth, overlooking the Pacific Ocean.² The water is so clear that I can see the sea floor in places, even though I’m a couple hundred feet above it, on a cliff. The sun is shimmering on the water. The weather could not be more perfect. Still, it’s weird. Still, it’s quiet.

We’re 150 miles away from home — a quick trip — yet light years away from home. Because our daughter Maisie is back at home. In great hands, mind you. So there’s nothing to be worried about, and we’re not. Still, it’s strange to be away. This is the main thing I’m thinking about on my 38th birthday.

Last year was a whirlwind. The best tornado imaginable. But

Continue reading “A Quiet Place”

Book: Reboot: Leadership and the Art of Growing Up

Jerry Colonna has written a “must read for everyone on planet earth book” titled Reboot: Leadership and the Art of Growing Up.

Seriously, go by it right now. I’ll be here when you return.

Regular readers of this blog know that Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud), Matt Cutler (who we still work with as CEO of Blocknative). I won’t repeat the story of Brad, Jerry, eShare, and NetGenesis, but it makes me incredibly happy to reflect on 23 years of friendship, which nicely lines up with

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Down the memory lane

148476702 52ca5604f2 oI couldn’t sleep so I started cleaning up my photo library and decided to upload some photos to my Flickr account. And while there, I ended up looking at some old photos. And I stumbled onto this one — with me, Paul Kedrosky and Matt Mullenweg. Mathew Ingram took that photo. I went to the conference hosted by Mathew in Toronto, a reporter, and I came back, an entrepreneur. I chucked away the security of a big media job and started my adventure. It all seemed so long ago! Ironically, I have not been back in Toronto since!

Just Keep At It

Just Keep At It

Just Keep At It

Just Keep At It

Be Careful Not to Lose Twice

There are times to fight.

No great startup has been built without getting one’s knuckles bloody at times. This is especially true because incumbents now know how much is at stake when they let a startup get a huge head start in a market.

So if you’re in a battle, if you’re right, if you feel confident you can win and importantly if the prize for winning is worth the fight — then go for it. But you should feel confident that all of these conditions are met before fighting and you should try hard to make your fight as unemotional as possible.

There are times to give in and compromise — even when you feel you’re right.

Perhaps the costs of “winning” the battle aren’t worth the consequences. This happens sometimes in lawsuits where as unpleasant as it sometimes is you have to chalk up some situations as “not worth fighting.” I have seen this in cases where a fight would take the CEO’s time & attention away from important business dealings or where the cost of not settling is huge (as in, inability to raise more capital until the dispute is resolved).

It might be that you assess the situation and realize you can’t win if you were to carry on the fight. This sucks because even when you feel “wronged” — there are times where you still aren’t going to win if you engage in battle. I’ve had this at times in dealing with big companies like Facebook and Apple where we realized that going against the machine was going to be counter-productive. It’s a Hobbesian world and the sooner you realize this the better equipped you are to know how you fit into it.

The key in life and business is to know the difference of when to fight and when not to and not to confuse situations due to emotions or self-righteousness.

I like to tell people …

“If somebody has wronged you AND you let it eat you up then YOU LOSE TWICE.”

If you decide that your current situation isn’t worth fighting then I recommend you come to emotional peace with that and move on. When you decide give in, do so graciously. Take the high road. Act and feel zen.

Back when I ran my first company I fought a lot. It seemed the world was always on fire and there was some skirmish to be had. I fought with landlords (when the real estate market crashed), venture debt providers (who wouldn’t take a hair cut when everybody else had to), the board (over compensation), our competitors (over everything) and any service provider who didn’t live up to our perceived contract (recruiters, accountants, sales lead companies, web hosting companies).

The longer I was

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The Legend of Mike and Mary

I was at dinner several weeks ago with Amy and two close friends who are 20 years younger than us. We were talking about what they were currently doing and they categorized their activities as “adding to” or “not adding to” the legend of mike and mary. I’ve anonymized them, but you get the idea.

The legend they were referring to was their internal legend as a couple. Neither of them could give a shit about the external legend, or what the world thought of them. This wasn’t about fame, ego, recognition, or acknowledgment. Fame and fortune didn’t play into the construct.

Instead, it was about their life together. Their journey. What they did together. It was the label for their narrative as a couple against the backdrop of a finite amount of time on this planet. Many of the activities in their legend where individual ones, but supported by

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Spring Break Should Be A National Holiday In The US

 

I’m a fan of spring break. I’m a believer in regular vacations. I love it when people I work with get away and disconnect. And, I do it at least four times a year.

Spring break feels like it has gotten out of control. Rethinking it could be interesting. This year, at least 50% of the people I work with regularly are on spring break this week. I think the other 50% go on spring break next week. Easter seems to be the pivot point for this.

Unlike the week before Christmas, which moves around every year, if Easter is the pivot point for spring break, life would be better if everyone in the US decided the week before (or after – I don’t care) Easter was spring break. Then, the rhythm of work in the US would slow (or at least change) for that week, just like it

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It Gets Better Than Better

It Gets Better Than Better