The Naive Optimist, We work a 4-day week and just raised $4.75m

We work a 4-day week (M-Th, 9-6) because we think that information work isn’t like manufacturing. Another hour at the MacBook won’t yield another $1,000 in profit. We believe that smart folks can get five days of work done in four days. Simple as that.

There are so many benefits to working less it’s hard to list them all, but here are the major ones:

  1. Recruiting is easy (we still pay full salaries and offer a very generous benefits package).
  2. Retention is easier. One of Team told me he regularly gets emails from Facebook trying to win him over and his answer is always the same: “Do you work a 4-day week yet?”
  3. Morale is boosted. On Mondays everyone is fresh and excited – not jaded from working over the weekend.
  4. I get to spend 50% more time with my kids then almost all other dads (three days versus two). Fifty percent. It’s insane. For those on the Team without kids, they get to spend this extra 50% on their hobbies or loved ones. (Hat tip to its_so_on for correcting my math and making it even more awesome :D)

I love reading stories like this. I can only imagine how terrifying and difficult it would be to setup a company with rules and a culture like this. It’s so against the grain, so unbelievable that I’m sure any dip in business, any down period, results in internal and external questioning of the policies.

I love that it is challenging the real common strategy to dealing with the startup anxieties: the grind. Both myself, and others I’ve worked with in startups all have at one point “taken on” moments of anxiety by throwing more time at it, or trying to grind through it. Looking back, this is incredibly ineffective. When you deal with your anxieties by trying to work harder, you end up with poor work and being completely spent. I wonder if by taking away time (a day in the week) you take away that strategy, and force people to deal with the anxiety and pressures differently.

And I can only imagine what having a culture like this does for recruiting and employee retention…everyone wants to work there, and no one wants to leave. A powerful combination.

Inspiration and Chai

It is very important to try and honour at least some of your dreams along the way. From the moment that you lose your health, it is too late. Health brings a freedom very few realise, until they no longer have it.

Amazing post made by a Palliative care nurse, looking at the greatest regrets people had when dying. I have to say that I’m not all that surprised by what shows up on the list, yet there’s a great deal of power to the list. It begs an evaluation of where you are, and how you’re spending your time.

I have some regrets about not having a conversation like this with my mom in her final weeks. I was so set on having positive thoughts, in hoping for a fix, or even just more time that I really didn’t want to have a conversation about life, death, lessons and regrets.

Island at the center of the world

The Island at the Center of the World: The Epic Story of Dutch Manhattan and the Forgotten Colony That Shaped America [Paperback]

I’m in the middle of reading this book, The Island at the Center of the World, which is a detailed look at the Dutch colonization of New Amsterdam (essentially present day NYC, and up the Hudson river valley). I must say I’m really amazed at how much of the “American spirit,” was evident even in those first waves of Dutch explorers. They were very tolerant of a mixing of cultures, religion, and had a strong belief in an upwardly mobile society. But As a history nerd who thoroughly enjoys reading accounts of the true paradise that was Manhattan, I already love this book. There detailed accounts of the bounty of the forests, the abundance of nut trees, schools of salmon and tuna welcoming Hudson, and the fields and fields of wild strawberries scattered around what is now Time square. As I sit and look out on to the “concrete jungle,” it’s truly hard to imagine what this place would have been like, but it does sound wonderful.

This morning as I walked I had a thought: It would be really cool to have those first waves of Dutch settlers here now to see what has become of the once wild island. My first assumption was that they would be in awe, and also very excited. But then I had to wonder..maybe not? Maybe they would have been horrified about the dense forests being replaced by streets. (don’t get me wrong, I’m very lucky to have been born when I was born, and to live in the city I live in).

Central park

Taken at Central Park – The Pond

“Success comes quickly…”


I was having breakfast this morning with a friend and experienced entrepreneur who recently sold his company.  He told me one of the big lessons he’s taking from his most recent experience is that success comes relatively quickly.  At first this sounds at odds with my recent quoting of this post from Chris Dixon which talks about the myth of the overnight success, but I think it actually supports it.  

My friend has learned that once you find something that clicks, it will take off relatively quickly.  He described it as adjusting a magnifying glass in the sun.  You often have to try the magnifying glass from many angles to find the right one, but when you do find that spot, it’s incredibly powerful.  This perspective clicked for me.  He’s basically saying you shouldn’t be spending your time trying to force something to work, but instead spend your time working on focusing the mangifying glass.  That is to say, set some feedback loop system and schedule, define the “sun in focus” moment, and go to work making adjustments into you’re in focus.  When you’ve got the feedback to know that angle is not working, you go to another, and another.  Don’t ever assume one angle is the right one, the one you must make work.  There’s another way, and it may be a tweak away from what you’re doing.  It may take many attempts, it may take a long time, but when it clicks it will really click…and with that “success comes quickly.”  

It’s Not What You Sell, It’s What You Believe – Bill Taylor – Harvard Business Review

What do you promise that nobody else in your industry can promise?

What do you deliver that nobody else can deliver?

What do you believe that only you believe?

The organizations that can answer those questions crisply, clearly, and compellingly are the ones that win big and create the most value.

Ahh spring

Taken at Flatiron Building

The myth of the overnight success – Chris Dixon

Angry Birds was Rovio’s 52nd game. They spent eight years and almost went bankrupt before finally creating their massive hit. Pinterest is one of the fastest growing websites in history, but struggled for a long time. Pinterest’s CEO recently said that they had “catastrophically small numbers” in their first year after launch, and that if he had listened to popular startup advice he probably would have quit.

Just had a discussion along these lines earlier this week. I’m amazed at how many successes there are that people assume were overnight. I’ve witnessed quite a few that were in fact nowhere near overnight, yet praised as such when they finally got noticed. It’s a misleading and harmful belief.

Icy trees on the road

Taken at 76 east