24 Ideas From Scott Berkun About Tech, Leadership, and the Future of Work

One of the few people who can match Paul Graham as writer is Scott Berkun. They have both succeeded as technologists, Graham in Viaweb + YC, and Berkun in Microsoft and Automattic. They both write thoughtful essays on a wide range of topics, like the Cities and Ambition or Street Smarts vs Book Smarts. If anything, Berkun is a bit more personable and relatable as a writer, he’ll refer to himself a bit more than Graham and use more culturally relevant examples.

I recently finished Berkun’s book, A Year Without Pants, about his experience as something like a product manager for Team Social at Automattic, the parent company of WordPress.com. The title of the book refers to the fact that the company is fully distributed and so you don’t have to wear pants to work if you don’t want to. I’ve written previously about 37 Signal’s book Remote, but this book is different because it doesn’t focus so intensely on the “remote” part. In fact, large swaths of the book are about times where Team Social were working together at an in person gathering.

Berkun primarily uses his experience at Automattic as a platform to offer a variety of other interesting and unconventional ideas about work. Here are 24 of my favorite quotes from the book (which you should read) and my comments. Continue reading…

Distribution is the New Currency

Here’s a thought experiment: What would you rather have: 1,000 dollars or 1,000 engaged followers?

Sure, having cash helps you pay rent and put food on the table. And when you are living paycheck to paycheck, the choice is obviously the former.

But if you’re reading this on a smartphone while on a break from responding to email, you probably have more to gain from the latter. Because real influence is very hard to buy. If you can shoot videos or record podcasts or write essays that capture people’s attention and trust, you have a powerful asset. An asset that probably is worth far more than $1,000.

In October, I released Winning Isn’t Normal and have made a few thousand dollars in sales. But what gets me most excited is reaching new audiences with my book. So I’m giving it away for just $0.99.

Amazon will only let me drop the price for three days: so click here between Jan 24 – 27 for the 87% discount.

Just one favor: if you like it, tell a friend and leave a review. It would make a huge difference.

You can use this button to tweet your support:

Notes on @acroll’s Lean Analytics presentation to Presidential Innovation Fellows

One of the great things about my current gig is that we bring in smart folks from all over to share their thoughts on innovation within government. Recently, Alistair Croll (@acroll), coauthor of Lean Analytics, flew in from Canada to share some of the highlights of his book and how we could apply a metrics-driven mentality to our projects as Presidential Innovation Fellows.

My coworker Sarah Allen and I pair-captured notes on the talk and Alistair’s given his blessing to share them publicly. Having glanced through the book, there is WAY more depth than even these extensive notes cover and I plan to read the whole thing. Enjoy!

alistair croll PIF

Part 1: What is the Lean Movement?

  • Silicon Valley hates failure more than the alternative: making something nobody needs.
  • Waterfall: Building a Nuclear Reactor: the spec is not going to change months from now
  • Spec – Build – Test – Launch
  • Agile: Requirements change before you launch if you are engineering things like software applications today.
  • Unclear how to satisfy requirements
  • problem – build – test, viable? → (yes) Launch
  •        → (no) Adjust
  • Reality: There is no clear set of requirements

Most startups don’t know what they’ll be when they grow up.

  • Paypal (first built for Palm Pilots)
  • Freshbooks (invoicing for a single web design firm)
  • Wikipedia (was going to be by experts)
  • Mitel (lawnmower company)
  • HotMail was a database company, Flickr (massively multiplayer game), Autodesk (desktop automation)

Consumer demand is the biggest risk

  • Kevin Costner (Field of Dreams) was a LOUSY entrepreneur
  • Reverse the idea: if they come, you should build it
  • You should not sell the thing you can make, you should make the thing you can sell.
  • “build just enough to quantify the biggest risk.”

CASE STUDY: Rubber trees

  • social entrepreneurs want to create rubber tree marketplace, couldn’t wait 20 yrs for rubber trees to grow
  • Risk was not “can rubber trees grow?”
  • Risk WAS “can you build the marketplace if you have rubber trees”
  • Focus on where the RISK is — validate that part. Continue reading…

Book Notes: Smart Choices – a Practical Guide to Making Better Life Decisions

Smart Choices a practical guide to making better life decisions cover

Note: this is an extensive set of book notes, clocking in at 1800 words. It’s a more weighty and dense post but (I think) worth the ~9 minutes to read it.

I recently read and finished taking notes on a book called: Smart Choices: A Practical Guide to Making Better Life Decisions (4.5 stars, 63 reviews on Amazon, affiliate link)

Making good decisions and executing well on those decisions are basically the only things that matter in life. I recently shared my book notes on Good Strategy / Bad Strategy, which explains how organizations can develop better strategies. This book is similar but focuses on how individuals can make better decisions, especially for the important aspects of their personal life. The approach is simple and the examples are relatable: buying a house, changing careers, planning an event, etc

Starting Out

The Acronym to Remember

The authors coined this somewhat helpful acronym: PrOACT, which stands for Problem, Objectives, Alternatives, Consequences, Tradeoffs.

The Biggest Mistake

The most common (and most easily avoided) mistake people make when deciding things is that they just don’t think about it. They just go with the gut. For smaller decisions, this isn’t always a big deal, but for bigger decisions, just taking a few minutes or a few hours to carefully think through a decision can make a big difference, especially given how bad our brains sometimes are at making decisions.

Problem Definition 

It’s useful to start off by asking yourself what problem you are trying to solve exactly. Their example is of a family that’s out growing their current home. One problem definition might be “What new house should we move to?” but perhaps a better one is “How can we find a home that fits our family’s needs?” which includes the possibility of renovating the current home.

Thinking about problem definitions is a fuzzy thing but a few other tips include:

  • ask what trigger caused you to consider the problem in the first place
  • question the constraints contained in your problem statement
  • recognize what other decisions hinge on this one
  • develop a workable scope for your problem definition

Digging Deeper


Objectives are what really matter to you in your decision. Before you look at your options, you should first think about what success looks like. What would constitute a best case scenario for your decision? For example, if you’re choosing a new office, your list of objectives might be minimal commute time, low cost, lots of space and fully staffed administrative services.

Continue reading…

Book Notes on [Good Strategy / Bad Strategy]

Good Strategy / Bad Strategy Book CoverI just finished a great book on strategic thinking called Good Strategy / Bad Strategy: The Difference and Why it Matters. It helped me understand what strategy really is both from a conceptual perspective and also concretely with case studies of companies like Apple & Nvidia and organizations like NASA and the US Army that had successfully implemented good strategy.

I highly recommend you check it out because the case studies really bring the concepts to light. But for your benefit and mine, here are some of the key takeways I got from it.

What Strategy is Not

Strategy or “strategic thinking” often refers to the work engaged by leaders of an organization, but just because someone is power is thinking, doesn’t make it strategic. A common mistake is to create goals, visions, budgets and/or “key priorities” and call that strategy.  They are NOT.

Strategy Has Three Elements

All good strategies have what the author calls a “kernel”. They are: a diagnosis of the primary challenge(s) and obstacle(s) faced by the organization, a guiding policy for how the organization plans to approach or overcome the challenge(s) and a set of coherent actions and resource commitments designed to carry out the guiding policy. Continue reading…