Making "More is More" true

"Less is more" is a popular insight to the point of being trite.

We reference it when designing products. We use slightly different language when invoking it for group decisions ("too many cooks in the kitchen") or personal obligations ("priorities").

We as individuals and groups do best when working within constraints. Sometimes the constraint feels like pressure (only having so much financial runway), sometimes its just an intellectual tendency of restricting the field of possibilities (dichotomies when combinatorics are possible).

Ultimately while I'm a believer in the notion "less is more", I can't help but wish we could achieve "more is more". It's feels like a deficiency that we can't make that work, particularly at the group level.

While I believe a smaller group can better cooperate & make smarter decisions, shouldn't one of the major programs of the future be about inventing ways to scale group size without sacrificing these qualities?

Take politics. It's no surprise that a ~500-person body is dysfunctional. I'd bet it would work better with just 5 people. But there's understandable apprehension in moving in that direction. So how do we make 500 people work together better? Or better yet 327 million?

I think many new developments be they in crypto, remote work, communication, or open source are working in this direction but I haven't seen it framed quite like this.

Making "More is more" true has to be one of the more impactful things we can work on.

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Purpose & Partnership

Putting down into writing "what it is we want" is a difficult exercise. Life generally does not require such precision.

How we live, succeed, and fail is, to a large degree, dictated by the random collisions of people and circumstance. We do not know who or what will influence us next. Often we fill in the narrative as we go. We take what life has dealt us, or what we have half-consciously taken on and we build the best story around it that we can.

Human beings excel at this skill. We can convince others, and more importantly ourselves, that each step we take is the right one and fits into some master plan. Given our mastery of such a skill, it may seem unnecessary to plot the dots in advance; to etch out in rigid form where we seek to go. A person can get away with a lot when going at things alone. He can stumble through life. But when partnerships are struck, be they in love, friendship, or business a heightened sense of responsibility must emerge.

This is the power in partnership. It forces us to form and articulate a sense of purpose. Put two wanderers together and the first serious question that undoubtedly arises is: "Where to?"

Written in 2011. Finding it very relevant as the team forms for the new company I'm building.

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Staying Weird

I'm about four weeks into working on my next thing. In the first three weeks I was very productive and heads down, mostly coding and writing. This past week though I've been more stagnant, doing a lot of thinking and second-guessing. This precipitated largely because I've had a lot of meetings in the last week.

Talking to people about what you are working on is important as so many in startupland evangelize these days. I'm not going to cover all the benefits, because so many already have. However, one of the side effects is that it gets you into problem-solving mode.

Now maybe that's not a side effect, maybe thats the whole point, but when you're early on your idea is going to have a lot of "problems". Your business model is unclear, the customer you are serving isn't well-defined, the product feature set isn't thought through, the launch strategy is rough, the retention play is non-existent. These are all important things to solve, but when you hear all these things at once, the tendency is to try and work through all of them, ASAP. I've noticed a bit of anxiety in myself as I suddenly felt frenzied to figure this all out.

Last night I took a deep breath and realized that in trying to answer all these things so quickly, my idea was becoming a bit derivative. You see we all praise speed in startups, but speed can often lead you to safe, pattern-matching thinking – especially when you have so many things to work through. I realized that while its important to know the problems you face, real breakthrough requires you to ignore most of them and focus on just whatever you think is most critical. Weird ideas need space to branch out and evolve. I'm partial to the Jonny Ives quote on this point:

while ideas ultimately can be so powerful, they begin as fragile, barely formed thoughts, so easily missed, so easily compromised, so easily just squished.

Two other posts helped me in get my thinking straight here:

So today, I'm memorializing my new found insight (and confidence) in this post and getting back to coding, letting my curiosity lead the way.

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Decision-Making Styles: Fists, Numbers, Words & Demos

One way to think about organizations is that they are decision-making machines.

An organization's mission constrains the things they make decisions about, and an organization's culture dictates how they go about making these decisions.

I believe there are a limited number of styles we bring to decision-making. Each organization can be thought of as a certain blend of these decision-making styles.

Here are the four styles I think pervade tech. Perhaps there are more but a blend of these four does a decent job of capturing decision-making culture.

  • Fists: "The most experienced person makes the call"
  • Numbers: "Let's decide objectively."
  • Words: "The best argument wins."
  • Demos: "The best experience wins."

For example, following the popular characterizations of the big companies it seems that Apple is Demos & Fists. Google is Numbers. Microsoft is Fists. Amazon is Words & Numbers. Companies almost always have a bit of each of these styles, but they will have a dominant style (or two).

Here are my own views one each of these styles:


By its very name and our strongly ingrained societal mistrust of authoritarianism there seems to be a lot wrong with using "fists" in your culture. I'm not going to waste space on that side of the argument – I hope they are already obvious. Instead let me defend why fists can be good.

In many decisions, no matter how talented the team and exhaustive the exploration of the decision, there will remain real ambiguity on the "right" path. If you're like me, you have found by now that for many decisions, you can argue persuasively on both sides of an argument. Organizations often need a tie-breaker. A person that sticks their neck out and says we are going to go this way. This is an example of "fists" as the ultimate rationale for why they chose Option 2 over Option 1 is simply "because I said so."

You should be part of an organization where you believe your leaders are better than random at making these calls. If you're not comfortable with "fists" being used at times it seems to suggest you don't have confidence in your leadership.


This is the most incongruent style in my opinion. While the others styles demonstrate some degree of direct conflict or assertiveness, "numbers" at its purest avoids debate altogether. A "numbers" person would argue that all forms of debate are flawed and subject to numerous biases. Better to agree on sound experiments and then let the data decide. At its worst it shows up as 41 shades of blue, but at its best it can drive compounding growth.

The biggest drawback to this style in my opinion is its hard to see how you can make big leaps with your product with a pure "numbers" outlook. Often a breakthrough relies more on an insight or demo that is hard to quantify in terms of impact. Also, I wonder on team morale when things are too often abstracted to KPIs (the mission gets lost to a pure performance-oriented culture).

That said, I think if you can couple "numbers" with a style that encourages debate it can shine. I love it as a secondary style but question it as a primary.


I would group Ray Dalio and his idea meritocracy in this style. Here you believe in the power of rational argumentation and want to create a culture where concrete ideas are considered on their own merit. In the extreme, you don't believe in the notion that there can be ambiguity on decisions like the "fists" like to claim. Every decision has a rational right answer, and its about making investigations as thorough as possible through recruiting good people and good processes.

I believe this style is underutilized in tech. We, of course, have Amazon and its six-page memo as a prime example but frankly writing is hard and time-consuming, and so we often punt to "fists" or "numbers" to avoid a grind it out back-and-forth. That's the argument for why we should be doing more with "words" – in a way I'm saying we're being too lazy.

That said, there are limits to "words". As Ken Kocienda describes in his book "Creative Selection", often these arguments end up looking like two people debating whose imaginary puppy is cuter – you can only get so far with words. The point being that we don't build and sell arguments,  we sell products. And a high percentage of a product's success is determined in its experience (ie., how it works).


Demos in a non-obvious way are a close sibling to "numbers". They both are uneasy about conference rooms – the province of "fists" and "words". Demos however instead of going all-in on objectivity, heads the other way and puts emphasis on subjectivity. The thinking here is that the act of building reveals the critical details about a decision. Moreover by embracing building, and thinking and debating in successive approximations of your product you never lose sight of how your product works. This experience is arguably as critical to the adoption of your product as the merits of the idea itself.

Taken to an extreme though, a Demos organization builds a wonderfully designed widget without much of a market. Some healthy amount of "numbers" and "words" can help pressure test if things are on the right track. And effective "fists" here should be strong editors with impeccable taste.

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How neutering Facebook helped me kick the habit

The idea of deleting your social media profiles has been around since the days of Friendster and MySpace but in the last year or two it has really picked up steam in light of many disturbing revelations on privacy and influence.

While I'm still a heavy Twitter user, and a moderate Instagram user, I have successfully stopped using Facebook for about a year now. For me it's been a low value network for some time as friends increasingly used it to share third-party content instead of life updates. Still, even though I've felt this way I found it very hard to kick the habit. I thought about quitting cold turkey and just deleting my Facebook but something always held me back. It also felt overly dramatic.

So instead I very gradually weaned my way off. Here are the steps I took, roughly in sequential order:

  1. Turned off all push and email notifications: Facebook is a very noisy app and they are always finding new things to alert you about. Don't let them suck you back in.
  2. Moved Facebook off my phone home screen: I was shocked when I realized how often I take out my phone because I'm just bored in the moment without a plan. Almost always I just stare at the app icons on my home screen and launch one out of boredom. As soon as I moved Facebook off to another page, a swipe or two away, I probably killed off ~30% of my app sessions. Crazy how even the smallest friction can do that.
  3. Deleted Facebook off my phone: After the first two steps, I had already found myself much less absorbed with Facebook. That made this step not as big of a deal as it might have been if I had started with it. One day I just deleted the Facebook app altogether, and just like that I wasn't a Facebook mobile user.
  4. Installed News Feed Eradicator on Chrome: At that point my Facebook habit was limited to just my laptop. But I found that I still checked it quite often. Facebook started as a website and in many ways its still my preferred way to use it. What I realized is that the biggest attraction to Facebook for me was something about its slot machine effect. Each time I log in, I have no idea what I'm going to find in the news feed. And that spontaneity ends up being very addictive. So one day I found and installed News Feed Eradicator for Facebook and my Facebook now looks like this:

As you can see my newsfeed is completely missing and in its place is a quote inspiring me to stay off Facebook. With this extension in place plus the steps I mentioned earlier I am no longer active on Facebook anymore.

Still, you might be wondering. Why not just delete my account altogether at this point? For me I found that my current setup is much more preferable for me. Here's a couple of benefits for my setup:

  • Log in with Facebook still works: I have signed up for several services using my Facebook account as my login, and its very convenient to continue using my Facebook to authenticate going forward. On my phone I am logged into Safari in order to keep using this feature. Technically I could get sucked back in by visiting Facebook on mobile web – but I never do.
  • Keeping your Facebook friend directory: I still find that Facebook offers some good utility. Occasionally, for example, I'll wonder about a friend I haven't talked to in a long time, and I'm still able to look them up or message them.

Essentially, what I've done to my Facebook is turn it into a pure utility. It's my identity when I want it to be to seamlessly use other services, and its something like my phone book when I want to check in on someone. The point is that its content and newsfeed are no longer a part of my life. So instead of the finality of #DeleteFacebook maybe just think about neutering it.

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Just-in-Time Education

Just-In-Time Directions

Remember good old encyclopedias? Back in my (childhood) days, if you wanted to look up a fact like the capital of a country or the biography of Abraham Lincoln you'd flip through the pages of Encyclopedia Brittanica. It was a slow, manual process and for most of us required a trip to the library.

Given how slow this process was, schools emphasized route memorization of facts. Nowadays, of course, we have Google and Wikipedia so we can look up anything we're curious about pretty much instantaneously. As such, we're increasingly rethinking how important it is know certain facts. Do I really need to know the exact year Lincoln was assassinated or do I just need to know how to quickly look it up?

This shift from studying/memorization to just-in-time information has also played out in the world of navigation. Gone are the days of carefully mapping out your route before starting a road trip. Today we punch in an address into Google Maps or Waze and let it mindlessly direct us. Even more than Google and Wikipedia, Maps goes a step further and works in close concert with your own actions; make a wrong turn or hit some traffic and Maps seamlessly course corrects.

When it comes to Education, many see the future as online courses and MOOCs. People point to Udacity and Udemy as the kinds of institutions the next generation of kids will attend instead of traditional universities. While I agree that these sorts of online video courses will continue to grow (I in fact built a couple of these types of companies :), I think the future of education will actually look more like Google Maps than Udacity. You see, the shift online is not just about taking a classroom and putting it online, it's about getting rid of the concept of a class all together. Instead of slogging through dense coursework in preparation for a future occupation or skillset, we'll immediately get started on a new task and technology will nudge us towards our goal as we go.

This shift will come about as more and more of today's complex tasks become increasingly deskilled. Driven by technologies like computer vision and AR, computers will gain a fuller sense of our environment, how we're operating within it, and can deliver timely intuitive instructions just when and where we need it.

When you step back and think about it, it's remarkable that driving automobiles has become so easy that practically the entire adult population can achieve mastery of this skill. Similarly when you look at fast food operations, someone in minimal time and with no required cooking skills can learn how to make hundreds of different dishes.

In the future, the same will be true of such activities as performing CPR, speaking a foreign language, performing handiwork around the house, producing and editing media, programming, and more. You won't need to take classes to start using these skills or even watch a video off of YouTube. Instead, in the moment, you will be presented with step-by-step instructions just like Google Maps does with navigation today.

On one hand this sort of future is frightening. You may say, this isn't education at all; we're not actually learning. To me this is similar to arguments over the future of work. As a society, we're going to be grappling with the fact that much work (not just blue-collar) can be automated. We'll need to ask ourselves which things are worth learning because doing so enriches us – and which things are we currently doing simply because there is a job-to-be-done? It seems to me that the latter category is ripe for automation.

On the other hand this future is incredibly exciting and even inspiring. You can look at just-in-time education as raising the baseline skills of every human being*. We will each be capable of doing at least the basics in previously impenetrable fields. From there its up to us to develop our mastery further. And I imagine as we work towards mastery there will always be some frontier that depends on more traditional practice or education.

For more on this trend see Tim O'Reilly's post on Gradually, then suddenly. My post was mostly a riff on what I picked up there.

*Actually, if I'm being a bit sensational, I should say every cyborg (part human, part computer). This future depends on us increasingly augmenting ourselves with computers. Note: We are already cyborgs as we walk around with our phones all day.

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Taste the burnt rice

Yesterday was one of those rare clear, sunny winter days in Seattle so we headed out to the beautiful Madison Park neighborhood for some sunshine.

We ended up having lunch at a Korean restaurant and ordered the Bibimbap. When the waiter put down the sizzling, hot stone bowl he suggested waiting a while so the rice burns.

Now I’ve known about the Korean appreciation for crispy rice for some time. When I first learned about it I was amazed because Iranians have a similar obsession. We call this rice “tahdig” — and it is often the most treasured part of the meal. I was a very finicky eater as a kid, so I would usually pile my plate with several portions of tahdig and maybe a little khorest to appease my mom.

Thinking more about my amazement over the fact that both Koreans and Iranians have discovered crispy rice, I think I know why I find it remarkable. Crispy rice is surely one of those creations that happened purely by accident. I like to picture some ancient Persian hundreds of year ago accidentally burning the rice and while throwing out these parts decided to maybe have a taste. I’m completely making up this origin story by the way, but I can’t imagine tahdig not being an accident.

The remarkable thing in such a discovery is that this person kept their senses open and explored the situation after making a mistake. So often, when something goes wrong we tend to shutdown. We label the situation a failure and move as quickly as possible to clean up our mess.

It’s like jumping off the wrong subway stop in some foreign city. You can beat yourself up and anguish over the next 15 minutes you’ll have to stand on the platform waiting for the very next train. Or you can say “Well I’m here now. A corner of the earth I know nothing about. Is there something worth seeing?” You may find that you are in some non-touristy neighborhood and end up at a restaurant where you have the most treasured meal of your trip. (I share such a detailed story because this in fact has happened to me)

The point I’m making is that an optimistic orientation to the situations you face allows you to make counter-intuitive discoveries. In this orientation try to think about how rare a scenario is for yourself or even for all of mankind.

So it’s not “damn I got off the wrong subway stop”. It’s “I’m on vacation, there’s no rush, and I’m somewhere tourists never go, maybe there’s an adventure here?”. In reality more often than not, there’s not something there. But occasionally you find something and those things often are the most valuable discoveries.

How many cultures just blindly throw out burnt rice because no one has yet slowed down and explored the situation?

How many incredible discoveries are right in front of you unseen?

Taste the burnt rice!

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Content beats Process: Making leaps in Product

If you're into product development and haven't watched Steve Jobs: The Lost Interview before, I highly recommend it. It's currently on Netflix.

One part that especially jumped out for me was this 90 second clip on content beating process. I suggest you give it a watch before continuing reading.

Watching Steve Jobs you realize how contrarian his thinking was versus much of the conventional views in product development today. Today entrepreneurs are pushed to “get out of the building” and talk to your customers. Steve Jobs famously said "people don't know what they want until you show it to them" – and generally ignored things like customer research and validation.

So who’s right? Both I claim, but I think Jobs has the more fundamental truth that real breakthroughs come from deep thought and sweating the details. This truth is especially profound these days as so many entrepreneurs and companies have leaned too far into process.

Today so many of us have fallen under the spell of Lean Startup thinking. Here ideas and details are discounted if not outright denigrated. When I see people under this ideology work towards breakthroughs they spend an hour thinking up as many ideas as they can onto sticky notes and then it’s about “getting out of the building” and seeing what sticks in the face of customers. There is this back-and-forth between building and validating that emerges but the building part is consciously minimized. You rush through building quick sketches of your idea so you can get back to the real gold: feedback.

Steve Jobs would call people who think like this “bozos”.

I’ll take a more balanced view but if I'm more in one camp it’s towards Jobs. Now I think building-validating cycles are valuable, but we have the weighting backwards. We should be spending more time internally debating and fleshing out an idea and exploring the intricacies that only reveal themselves as you build. The gold is in the art and craftsmanship that is brought to building.

Now the Leaners will say that the Steve Jobs way is risky for your company's prospects. I think there's truth in this because having reliable intuition about new products is exceptionally rare. Most of time when you think you have it, you probably don't. But let’s state another truth which is that entrepreneurship is fundamentally risky. Any process that claims to remove risk comes at a cost. My suspicion is that Lean-thinking leads to derivative products. It helps raise the likelihood that you don’t outright fail, but by following what your customers tell you, you give up a shot at breakthrough. At times this tradeoff makes sense, but you need to think about your goals. Sometimes you need to over-index on process (don't fail) and other times you need to focus on content (real breakthroughs).

For product people that want to be more like Steve Jobs, skip the black turtlenecks and watch the interview above. Also I can recommend a fantastic book I'm reading called Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs. Finally, spend some time learning about Allen Zhang, the founder of WeChat, who seems to be a Jobsian.

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Transitioning out of your Startup as a Founder

In tech we call our companies "start-ups" which I think is an apt name because a lot of the sweat and tears occurs in this stage of just figuring things out. For most companies the act of starting up actually takes years and is filled with many reformulations and relaunches until things start working. It's feels a lot like you are tinkering away in a toolshed, building a machine, hoping that your work will lead to it actually booting up.

Less discussed is the stage of voluntarily moving on from your startup and have it continue without you. This is clearly not a stage everyone faces, but I think enough do that it's worth sharing my experience.

Yesterday, was my last day at Cody /Alo Moves, a company I co-founded seven years ago. Believe it or not this whole process of moving on kicked off nearly a year ago. It takes a long time for a founder to unwind him or herself from a company. I wanted to share some of the steps I took as part of this process.

Before I jump in a little context about our company: We were acquired about 1.5 years ago by Alo Yoga. As part of the acquisition, we kept our HQ in Seattle and increased our team headcount from about 20 to 25 FTEs. Our acquirer is an apparel company and we're a tech / media company so there was some, but not full overlap in our respective disciplines.

So with that context, here's how the whole thing went down:

  • Talk early with your co-founder(s): Before my mind was really made up on moving on I had a series of chats with my co-founder, Paul. I made sure to have these talks outside of the office, in the evening, away from the usual hustle and bustle of the office. I felt like a calmer environment was critical to just have an open voicing of where I was at – particularly since I wasn't sure what I wanted.
  • Plan out your org chart for the transition: Once it became clear what I wanted to do and Paul and I digested it, we turned our attention to the org chart. My responsibilities spanned product (which I directly managed), marketing (we had a lead but I was heavily involved), and operations (HR, office, accounting, legal). After listing out all my responsibilities, we realized we needed at least 2, and ideally 3 people to replace me, as well as shifting some of my other responsibilities to existing team members. This is pretty common for founders. We tend to do many disparate things and given our understanding of the business can do them efficiently.
  • Back into a timeline: Given where we needed the org chart to go, and that some hires should be sequenced we decided that 9 months would give us enough time to make this transition with high-confidence. This also got us through the holiday / new year season which is our biggest and most intense. By leaving in March, the business would be better situated to deal with any bumps. This turned out to be just enough time so I'm glad we picked a long runway. On the otherhand, I have to say that personally dealing with such a long period of transition ended up being draining for me. More on that later.
  • Determine a communication plan: Once we knew my timeline, we had to think through who to tell and when. What we quickly realized is that there would be a lot of questions from opening some of the job roles we had earmarked so we should communicate early. We decided to tell the team in September that I was leaving in March, so a six-month heads up. Partly we felt that such a long heads up would emotionally dampen the news. I decided to do this communication in the days just before our annual retreat, to give me plenty of time with the team afterwards to work through the news. We anticipated it being unnatural to share this news and then just get right back to the regular work week. So on a Tuesday afternoon, I called the founder of our parent company and shared my intention. The next morning I sent an email to the entire team, and held an all-hands a few hours later to talk through it face-to-face. The next day we went on our retreat and I had a number of 1:1 chats during all the fun. All in all, this rollout went very well.
  • Strategically disengage: This was probably the hardest thing I did, and I'm not 100% sure it was for the best. Even before I communicated to the team, I made the decision to increasingly take a backseat in the org as this transition unfolded. My thinking was that rather than suddenly disappear one day, its better if the team just learns to push on their own while I'm still there. This was really hard as I tend to be pretty vocal and hold strong views in meetings. Suddenly I was holding my tongue constantly. In time, I started not attending almost all my regular meetings other than our weekly leads meeting and the product meetings. I can say for sure this made the transition a smooth one, as when I left the teams were already self-sufficient but it was hard for me to be so passive for the last 6-9 months. If I had to do it again, I would've started this process maybe with just 3 months to go.
  • Take a supportive role in recruiting: One of the areas that was especially awkward in this period was figuring out how to best be involved with recruiting. As a founder, I was traditionally very involved and had multiple touch points in the pipeline. But now it felt weird as I didn't want to hold back on the fact that I was months away from leaving. So in the end I decided that I would be involved only in the middle of our process. This is where we give folks a project to do and review over the phone. Candidates would work with other team members for the initial phone screens and in the final interview loop at the office. In this way, I still could gauge the skillset of the candidate and give my opinion but I wasn't a "face" of the organization that they had spent a lot of time with.
  • Spend your last month completely away from the office: While yesterday was my last day, we actually had my farewell party and all last month. With a new product manager on board, Paul and I agreed that it would be best for me to just get out of her way. So after three weeks together, I stopped going into the office. For the past few weeks I've been helping Paul with transition, mostly just doing calls and meeting up with him outside the office. This has been nice as many things only come up only after you're gone. Also, on a practical matter there were several services and payments that I hadn't fully transitioned that we caught during this phase.

I hope this was helpful. If anyone is starting down a path like this and wants advice please feel free to reach out.

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Microdosing on Entrepreneurship

I've recently taken to blogging again, and tweeting more and its amazing just how much it feels like a miniaturized version of the early days of a startup.

There's the joy in crafting your vision and a sense of inevitability that what you have to share is going to be quickly adopted by anyone in its path.

Then, almost always, there is the crash that hits you as your launch is met with indifference. You open your eyes to the struggle for attention and that you have to give at least equal thought to distribution as to the product itself.

Suffice it to say that I haven't been getting much engagement on my posts (literally just a couple dozen visitors over the course of 6 blog posts). It's to the point that when I check Google Analytics my own visits significantly skew my metrics.

This feeling isn't new to me. I lived and breathed it everyday in the early days of Cody and Magoosh. Much of entrepreneurship is dealing with indifference and how to keep making progress in the face of it. You end up needing to experiment a lot and get out of your comfort zone. You end up feeling ridiculous quite a bit. But somehow you wake up each day with renewed energy to try again  – that's when you know you're on the right path. I know that eventually you can breakthrough, and its largely persistence that will make it so.

With Twitter and blogging, I'm feeling those same things again. But here I am only spending minutes or hours crafting something. With entrepreneurship you are spending months and years, so this whole cycle gets amplified to an extreme.

Still, the next time someone asks me how entrepreneurship feels I know my answer. I'd say spend some time crafting the wittiest tweet you can, post it, and deal with the fact that you have zero engagement.

That right there is a microdose of entrepreneurship.

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