Matt Inouye

Beyond Vibe Coding: Agent Onboarding and Orchestration

2026-03-04T00:00:00+00:00

Like many people in tech, I’ve enjoyed the vibe coding era over the last year. I built dozens of applications, everything from Chrome extensions to full-blown web apps. It’s been a lot of fun working with programming languages and stacks I’d never touched before, and getting to sample tools like Lovable, Bolt, Replit, and Cursor.

Now with Claude Code, it’s remarkable how easy it is to one-shot entire applications. If anything, some of the magic feels gone because there’s no real prompting craft left to it. Even for more complex agentic coding workflows, getting a single agent to onboard to a codebase, write incremental code and tests, and open a PR feels like a pretty trivial skill at this point.

I think the next evolution in AI-driven development is going to be around agent onboarding and orchestration.

Agent onboarding as I imagine it, is the art of quickly getting an AI employee up to speed on what you want it to accomplish. It means giving it full context, objectives, and goals, and creating the preconditions for one-shotting complex tasks. For coding agents, this is already fairly straightforward. But for other functional areas like marketing, data analysis, and legal, the onboarding piece can be time-consuming and complicated. Being an expert at onboarding means your agents produce better quality output, faster.

Orchestration is the next frontier beyond that, where you move from having a single agent working for you to dozens of agents working in parallel. The mental models and harnesses for managing orchestration at that scale are still pretty immature today, but I think they’ll develop significantly over the rest of this year. The end-state skills that I believe will matter most for orchestration are, interestingly, the same ones that matter for managing people in an organization:

Being a clear communicator
Being able to delegate tasks effectively
Setting organizational structures that are well-suited to getting goals and objectives accomplished

By the end of the year, someone who’s great at onboarding and orchestration could build a massive company of one person with thousands of AI employees. This is probably already happening to some degree, but will become more common. I’m not sure exactly how it all takes shape, but it’s helpful to imagine some ways it could manifest itself.

AI employees communicating across thousands of email accounts, creating a record of work streams just like in a real company.
Slack-like chat environments where agents collaborate asynchronously.
Detailed onboarding protocols optimized to give each new agent exactly the right context and depth of training for the complexity of the tasks they’re being given.

The amount of leverage that’s going to be possible is truly mind-boggling.

Self-publishing is Easy with Claude Code

2026-01-07T00:00:00+00:00

I’ve had a personal website for a decade and I post maybe once or twice a year. The worst part has always been trying to remember how to actually get my content live. My workflow is relatively simple, but there is a ton of friction when I try to recall the details of committing changes, where to create new posts, and the conventions for my specific static site generator. I usually end up making a simple mistake or spending 5-10 minutes trying to load up all that context into my brain.

Claude Code solves this problem completely. I just describe the publisher process, and then add it to the project’s claude.md file. Then anytime I want to create a new post, I can simply ask Claude Code to create a simple template using my conventions, and then commit, deploy, and build a new version of my site when I’m done.

It’s a really magical experience.

The best part is it means that static site generators get new life. You don’t need to worry about the specifics of Jekyll or Hugo. Once Claude understands your stack its smooth sailing. And everything can be hosted for free on a service like Netlify or Cloudflare.

Now I just need to figure out the writing piece…

Clarity Over Completeness

2025-06-10T00:00:00+00:00

Olga et Paulo: la Soupe (Maternité) by Picasso

In tech, we love to mythologize the six-page memo. I’m certainly guilty of it. It’s been the gold standard for a thoughtful, thorough document that distills complexity and invites structured debate.

But here’s the truth: no one’s reading it.

Not because people don’t care, but because they literally don’t have time. Back-to-back meetings. Slack overload. Multi-tasking, upon multi-tasking. The long-form memo gets forgotten, skimmed, and at worst, misunderstood. What actually moves things forward isn’t depth or thoroughness. It’s clarity.

A single slide. A sketch. A paragraph. A usable prototype or mock-up. The simplest possible artifact that allows a team to start reasoning about a problem or a solution and react in an honest and genuine way. This kind of tool turns into a collective compass for a group. As long as it generally points north, it can help you find a way to a decision or path forward.

One of my favorite paintings is a Picasso line drawing of a mother feeding her child. There’s very little to the picture, but so much of the scene comes through as you gaze at it. The picture starts the conversation about the emotion and the characters and lets you continue much of it in your head. But the little details that are there are very clear.

So it is with a lot writing on the job–you don’t need 1,000 words when the right 20 will do.

So here’s the shift: Write and create to advance the conversation, not to perfect the document or artifact. If it gets people thinking, aligning, or building — it’s done its job.

Simple is clear. And clarity brings alignment and speed.

Vibe Hosting

2025-04-22T00:00:00+00:00

Writing code with AI is a lot of fun.

Yes, debugging is painful. And it’s easy to get stuck in endless loops. But being able to think up something and watch it materialize in minutes is magical.

One of the under-appreciated aspects of vibe coding is how easy it is to host projects with the many platforms out there. My preferred host today is Cloudflare Pages. Hosting a site on Cloudflare is free and you get a nice *.pages.dev subdomain. Deployment is as simple as uploading a folder or a zip file via the browser. You can also connect your site to Github directly for automated deploys.

Let me walk you through how simple it is to go from idea to hosted app.

—–

I came up with an idea for a simple joke app for my daughter. I want to show a joke in big text, and have a button to reveal the answer. I mocked up something quickly and then fed a simple prompt to Cursor.

Simple app mockup.

Prompt I fed into Cursor.

After some back and forth–I ran into some react compatibility issues–I finally got a working protype.

Here's what Cursor came up with (using Claude 3.7 Sonnet)

I was going to use ChatGPT to generate a big list of jokes and then feed that back into Cursor–but the jokes from the intial prompt were great so I just went with that.

Then I just built the React app and uploaded the build directory to Cloudflare.

Free hosting on Cloudflare pages

And now you can see the finished product at bigjokes.pages.dev.

All in under 20 minutes. Magic.

Defaults Matter

2023-09-14T00:00:00+00:00

Defaults are like drugs.

We underestimate their influence and we overestimate our ability to avoid them.

For product designers, defaults are particularly dangerous–they provide license to manipulate user behavior in a guilt-free way. By providing choice, technically a user could opt-out of a strong nudge. But in practice very few will.

Google is currently spending millions to convince a judge that defaults aren’t actually all that important. There is ample research to disprove this. But the argument speaks to something deep inside us that wants to believe that we aren’t so easily manipulated. It doesn’t feel good to think that just because we get anchored on something, we’re too lazy to change or to think for ourselves. Especially if defaults are used by big corporations to maximize profits or preserve monopolies.

However awareness alone can lead to two good outcomes:

We push back. We cancel, unsubscribe, opt-out, and choose alternatives.
We exercise restraint. We think twice before using defaults in a manner that manipulates, knowing that the average user will stick with the base settings.

I’m curious how the discourse around defaults changes as a result of this Google case. I hope it will spur a lot of good discussion. I do think that it draws serious attention to Apple’s bundling strategies. Those seem at risk in the coming years.

Thoughts on Google from someone much smarter than me.

The Courage to Explore, the Commitment to Stay

2023-02-25T00:00:00+00:00

Life is about trade-offs. Trade-offs mark decision points that can have long-lasting effects on your career, your family, and your happiness.

One of my favorite articulations of the tension between trade-offs is, The Courage to Explore, the Commitment to Stay. This came from an interview with Sebastian Junger–most famous as the author of The Perfect Storm. He’s asked, what advice his 70-year-old self would have for him, and this was his response:

The world is this continually unfolding set of possibilities and opportunities, and the tricky thing about life is on the one hand having the courage to enter into things that are unfamiliar but to also have the wisdom to stop exploring when you’ve found something that’s worth sticking around for. That’s true of a place, a person, of a vocation. In balancing those two things, the courage of exploring and the commitment to staying, it’s very hard to get the ratio, the balance of those two things right. And I think my 70-year-old-self would say just really be careful that you don’t err on one side or the other because you have an ill-conceived idea of who you are.

There are seasons in life where exploration is a natural, almost expected behavior. In those periods, little courage is necessary to seek new experiences, environments, or vocations.

There are also times when commitment is a normal outgrowth of life-stage–the urge to “settle down” and plant roots. I think I’m thoroughly there today. For someone in this mode of life, doubling down on the stable parts of life is extremely comfortable.

What I love about Junger’s framing is the courage aspect. It takes a certain amount of bravery to move out of one’s default mode. There’s a certain amount of risk involved. Swing too far the other direction and it can result in decisions that bring significant regret. Courage isn’t about payoff maximization. It’s about conquering fears of failure and understanding who you are as a person.

More and more, I think that this understanding (of oneself) is the key–or at least a prerequisite–to a happy life.

Shutting Down Side Projects

2022-10-23T00:00:00+00:00

I finally shut down a website I had been running since 2009–over 13 years.

It was hard. The site was still generating income. And it felt like a huge inflection point was just around the corner. I’d had that feeling for many years–that I was one small change from huge growth.

But the reality was it hadn’t been growing for a long time and required a non-trivial amount of attention and upkeep. Every month I had to pay bills, taxes, stay on top of alerts and broken scripts that kept the site up to date.

By far the biggest cost was the way the site absorbed my creative energy. Whenever I had a spare moment, my thoughts frequently gravitated towards how I would improve the site: design a new feature, rearchitect a component, or driving a new growth tractic. When I actually set about to implement those ideas, my creative thoughts were dominated by them until they were completed, which often took weeks at a time.

Now that I’ve finally flipped the off-switch, I feel like I’ve opened up a huge expanse in my head. It feels liberating. I wish I had done it sooner.

Cost of Carry

There’s a concept in software engineering called the “cost of carry”. Every new feature brings along with it additional complexity, and makes adding features in the future more expensive. I believe that every personal side-project has a cost of carry. The most obvious and impactful cost is the opportunity cost of the project. What else you could be thinking about and making progress against? Your brain has limited slots for Work-in-progress (WIP). Filling that finite space isn’t something you should take lightly. You should also reevaluate what deserves that space on a regular basis.

For long-running side projects this cost of carry can be quite high. But in the moment, all you can think about is “I’d be crazy to pull the plug! What would my users think?”

Certainly not all side-projects are bad. Especially those that have very minimal cost of carry. I have a chrome extension I haven’t had to touch for years and it provides a nice service to hundreds of users (including myself). I’d love to have a portfolio of those.

Power of Elimination

Shutting down a side-project is really about being honest with your priorities, and being comfortable with ruthless elimination.

There’s an interesting story about Warren Buffett teaching his pilot about prioritization¹. He asks the pilot to write down his top 25 goals, and then review the list and circle the top five most important ones. This all sounds straight-forward, except then Buffett tells the pilot that the remaining 20 goals are the “Avoid-At-All-Cost list”. You don’t do anything with those until you acheive your top five.

That’s painful advice to follow through on. It means you need to kill off some of your goals, because they’re important, but not important enough.

Time and focus are limited. So sometimes you really do need to pull the plug.

https://jamesclear.com/buffett-focus ↩

Bystander Businesses

2021-05-30T00:00:00+00:00

As large platforms consolidate attention online, they are incentivized to launch new products that feed on that growing attention. Sometimes these products are a hit, and grow into their own standalone offerings that serve a unique customer need. However, most of the time they limp along, surviving on the residual traffic that is diverted their way by the core business.

I call both of these types of businesses—the hits and the mediocre—bystander businesses.

A bystander business is one that has no real distribution strategy to start. It’s sole vehicle for growth is the large amount of traffic spun off its way, from the larger and more successful business. Facebook Marketplace is one example of this. In the early days, you might not have headed to Facebook to sell your couch, but since your attention was already there, it was easy for Facebook to divert you to their Marketplace.

Another example is Google Shopping. Few people start their shopping journey on Google Shopping, but simply pass through as Google launches searchers into the Shopping experience based on their queries. Google Shopping isn’t a real destination, its just “selling bottled water at the stadium gates”. The fact that they sunset their mobile app this month seems to confirm this.

Why is it important to identify bystander businesses? Because the rules they play by are fundamentally different from most of their competitors. First, they don’t need to to be self-sustaining—they can feed off of the core businesses, and thus the economics don’t need to reflect product-market fit. Second, they can have incredibly long time horizons for finding success. It really depends on the level of patience in the organization. Finally, they may not even be in a market that is sustainable as a standalone business. Their existence may, instead of pointing to a secret that only Google knows, actually just reflect an excess of cash, talent, and traffic.

Copying a bystander business could be one of the worst moves you could make. But there are some slim glimmers of opportunity. Bystander businesses have far less optionality in terms of modifying the fundamentals of their business. There may be ways to compete that are hard for incumbent bystander businesses to replicate. However, if the incumbents sole goal is to commoditize the product space, then startups should be worried.

Amazon's Marketplace Problem

2020-09-04T00:00:00+00:00

Amazon is the unquestioned leader of selling stuff online. Over half of US adults are Amazon prime members.¹ They are US ecommerce for many shoppers.

And yet there is a growing problem with shopping on Amazon. It isn’t as simple or easy as it has been in the past. Shoppers are now flooded with choices that are difficult to sift through.

Shopping on Amazon is not an enjoyable experience. For the most ‘customer centric’ business, this seems like a growing problem. Paradox of choice and poor peer reviews compromise the user experience.
— Post M. (@Post_Market) September 3, 2020

As several smart people in the thread above point out, Amazon doesn’t have the best shopping experience, but it does have the best buying experience.

However, focusing on buying at the expense of shopping has presented a major risk. Shoppers are finally figuring out what Amazon really is. A marketplace.

The Buy Box: A Market Where the Consumer Wins

Over the past decade, the Amazon marketplace has been hidden from consumers through the ingenious “Buy Box”.

Amazon abstracts away seller choice. And it doesn't necessarily prioritize itself. In the above example, all three sellers (including Amazon) are offering the same price, but "The Music Zoo" wins out.

The Buy Box is an opportunity for Amazon to create a mini-market inside of every product page. Through a complex system that factors in price, reviews, inventory levels, and dozens of other factors, they dynamically select which seller’s product gets purchased when a shopper clicks the “Buy Now” or “Add to Cart” buttons. Over 80% of the time, the default buy-box merchant remains selected ². Because of this stickiness, winning the Buy Box is essential for sellers. They need to provide good service and low prices to ensure they stay on top.

While this drives sellers crazy ³, it’s a huge win for shoppers. Despite the dozens of potential sellers offering the same product, complex choice is cleanly abstracted away. Since Amazon slowly layered this on over time, it’s generally imperceptible to shoppers. And best-in-class logistics like Fulfillment by Amazon (FBA), made their strategy impossible to replicate.

By hiding seller choice behind the *Buy Box*, Amazon created a great buying experience.

Looking to the future, mobile only accelerates this trend. You have less real-estate to even see and compare the other seller options.

SKU Proliferation: The “Retailer” Myth Crumbles

Since Buy Box competition is high, the primary way to differentiate as a seller is through the creation of new products. Why compete against other sellers, when you can create your own products, for which you own the Buy Box 100% of the time?

This is a big problem for Amazon. It means that suddenly you have a huge increase in the number of unique products, with little competition on each product page. Amazon can’t leverage their Buy Box magic for a shopper. Instead shoppers are forced to wade through the messy market themselves.

With more 'unique' products, Amazon can't abstract away choice.

If you want proof of this, start at the Today’s Deals page and perform searches for some of the products you see promoted. There are hundreds of similar products across a variety of categories that look nearly identical.

Searches for "percussion massager" and "beach blanket". See a difference?

As the number of unique saleable goods increases, sellers are no longer hidden behind competition on individual product pages. And shoppers for the first time start seeing search results that look a lot like eBay.

Shopping Isn’t Customer Centric.

Amazon has further painted themselves into a corner because they’ve intentionally chosen to monetize the shopping experience through ads, deals, coupons, and promotions. Sellers can spend money to improve their visibility and Amazon will willingly take it.

You can see the effect that this has on search results. Many of the results you see are paid, and even the organic results have coupons or other paid add-ons to tempt shoppers.

While label’s like “Amazon’s Choice” are occasionally helpful, these seem like overly subjective and ultimately weak signals.

Sales and coupons are advertisements paid for by the seller, in addition to the discount.

What Now?

Amazon appears to have two paths forward. The first is to drown out the noisiness of the marketplace. Amazon is approaching this through a constant series of bets around discovery (e.g. experiences like Amazon Live) and iterating on search result layouts. They’ve also pushed agressive redirection on product pages, in the event that a user landed on a product that wasn’t the “best choice” (in their estimation).

"Similar Item to Consider" units are placed on product pages above the Buy Box

The second option is a large-scale culling of underperforming and low-quality sellers and inventory. It seems inevitable that they’ll need to take some action here, if only to address some of the counterfeiting issues they’ve faced in the past.

In the absence of truly threatening competition, major action seems unlikely. But as a Prime member, I hope they invest in making shopping a significantly more enjoyable experience. Left unchecked, this gap could turn into an existential risk.

As of December 2019, 112M Americans are Amazon Prime members. ↩
https://www.bigcommerce.com/blog/win-amazon-buy-box/#wrap-up ↩
There are dozens of businesses dedicated to helping sellers reprice their products and win back the Buy Box (e.g. Repricer). ↩

Battles of Inches or Miles

2020-06-28T00:00:00+00:00

h/t to @sriramk for this idea.

There are some product efforts that are battles of inches. The goal is to generate a tiny incremental improvement in a high-leverage system–for example, a percentage point increase in a KPI that yields millions in incremental revenue.

These battles of inches require rapid iteration and testing with lots of metric-driven experiments. The numbers guide the outcome, and you can test your way to a win.

There are other product efforts that are battles of miles. These are major bets that are driven more by product sense and deep knowledge of the market and customer. Metrics and experiments are important, but ultimately intuition guides the outcome.

It is critical to know what type of product battle you’re engaged in. Bringing a purely analytical toolkit to a battle of miles will spell trouble. And conversely so will bringing pure product sense skills to a battle of inches.

The worst possible strategy is to engage in the wrong battle from the start. A battle of inches over low-leverage territory means you stay busy, but accomplish nothing. A battle of miles where the ultimate prize is small means you accept a tremendous amount of risk and cost for very little reward.

So carefully assess before engaging. And then bring the right toolkits.

The Curse of Excess Information

2020-06-13T00:00:00+00:00

In the age of endless information, what if more information isn’t actually a good thing?

In The Black Swan, Nassim Taleb asserts that additional information can actually be an impediment to forming knowledge. Instead of deepening our understanding of an issue, it can falsely deepen our confidence in pre-existing ideas and opinions. He describes this type of information as “toxic”.

One of the most striking examples of this phenomena was a study run by Paul Slovic with horse handicappers, the odds-makers in horse-racing¹. Each handicapper was given access to 88 variables, and then asked to choose five variables to judge 40 different races. They were then given an additional opportunity to select 10 variables and judge another 40 races. This was repeated with 20 variables, and finally 40 variables.

Common sense would lead you to believe that accuracy would improve with more information. However, Slovic observed the exact opposite. Inconsistency increased as the handicappers were given access to more information. And even worse was the fact that the confidence of the handicappers increased as their access to information increased. More information increased confidence, without increasing understanding.

Another study referenced by Taleb, looked at the confidence levels of psychologists as they received more information about a case ². The psychologists were gradually given more information about a young man and were asked to share confidence in their clinical decisions as they received the additional information. Much like the horse-handicappers, their confidence in their own judgements increased as they received more information, while the actual accuracy of their predictions quickly hit a ceiling.

Both examples show that judgemental accuracy is bounded, but confidence in one’s judgements are unbounded.

More information can increase our confidence, without improving our predictive power.

This poses a truly challenging problem. The more of an expert we become on a topic, the more overconfident we become in our own opinions and judgements. Instead of using more information to broaden our understanding, we simply shoe-horn it into our own pre-existing mental models. Any information that is inconsistent with these models is ignored or incorrectly weighted.

We’d like to think that our brains are capable of easily synthesizing multiple pieces of information into a coherent whole. However we ultimately use much less information than we think we do to make judgements. And we are often wrong about how we weigh these pieces of information in our head.

So what are we to do? I think awareness is perhaps the only tool we have to combat these biases in ourselves and others. Here are some things to constantly keep in mind:

Recognize the limitations of your own judgments
Be skeptical of the confidence of experts
Seek out and ponder information that contradicts your beliefs
Beware of your own confidence, and watch for rapid increases in confidence

Five Rules to Read More Books

2020-05-25T00:00:00+00:00

Reading a book is a big ask. Not only is it a large time commitment, the payoff is unknown. Sometimes it’s a big win. Occasionally it’s a waste.

As I’ve struggled to read more over the past four years, I’ve developed five rules that have helped me to dramatically increase my reading output and overall reading enjoyment.

Read physical books
Acquire indiscriminately
Read spontaneously
Read several books at once
Quit early

These rules have helped me to both read more, and to read more broadly. By matching books to topics, questions, and areas of interest that are top of mind, I’ve been able to sustain a high level of reading pleasure, while tactically educating myself on topics of personal and professional relevance.

Read Physical Books

I’ve gone through stints of reading on the Kindle or listening to Audiobooks. Unfortunately, I’ve found limited success with both. There is something incredibly powerful about the tactile feeling of a physical book and I find that being able to flip through pages to gain context, make notes, and highlights in the margins, and physically see a book’s presence in my apartment make them superior to digital alternatives.

I’ve also found that my retention has significantly increased with the switch to old-fashioned books. It’s unclear the root cause, but I did have multiple experiences listening to books where I could barely remember the title at the end. It was sort of like trying to recall the landscape on a train ride–I could remember that I had seen it and that it was sriking, but I couldn’t pull any details from memory.

One major downside of physical books is having to lug them around in a suitcase when travelling. But that tradeoff is worth the retention upside.

This Van Gogh biography isn't exactly portable.

Acquire Indiscriminately

Obtaining a wide-variety of books for your personal library, can be a big commitment–both in terms of cost and storage space. But the dividends can be massive.

Several years ago I started lowering my filter on what books I bought. Whenever I received a half-decent recommendation, I immediately purchased it. When I went to used book stores, I bought books in a variety of domains that inspired me. Books started piling up on shelves.

One of the immediate side-effects was the constant reminder that I had a lot to learn. There is so much knowledge in the world and a stack of unread books is the perfect symbol for that.

Nassim Taleb popularized this Umberto Eco quote about unread books in The Black Swan:

Read books are far less valuable than unread ones. [Your] library should contain as much of what you do not know as your financial means, mortgage rates, and the currently tight real-estate market allows you to put there. You will accumulate more knowledge and more books as you grow older, and the growing number of unread books on the shelves will look at you menacingly. Indeed, the more you know, the larger the rows of unread books. Let us call this collection of unread books an antilibrary.

Personally, I think these stacks of books are less menacing and more inspiring. But they certainly weigh on your mind. And given a choice between watching TV or chipping away at a stack of books, their physical presence tips the scales in favor of reading ever so slightly.

Read Spontaneously.

After acquiring a large number of physical books and spreading them throughout your home, the real magic can begin to happen. You start being exposed to books in the periphery of your daily life–dozens of times every day. This is the true power tsundoku.

Walking through my apartment, I’d pass by stacks of titles, some of which I’d be exposed to hundreds of times before opening them. I was free to pick up a book, flip to a random page, and test the waters. And very often a certain title would match my mood or frame of mind or a random interest I had been mulling and it was like a lightning strike–I was able to devour titles through that combination of repeated exposure and serendipity.

This spontaneity made finding the right book feel like a treasured discovery–the perfect match for a mood or a problem at hand. Negotiation, relationships, art, philosophy, fiction–no subject was too arcane, provided my library had enough breadth.

Read Several Books At Once

Reading multiple books at once allows you to explore spontaneously, but in a more constrained manner. Your whole library isn’t at play, but a handful of works can be weighed each time you have a spare moment. Time of day, mood, and energy-level will all influence what speaks to you. This also makes TV less of a distraction. If you’re reading only one book that calls to you in certain moods, it makes the pull of TV or mindless internet browsing that much stronger.

By reading several books, you are cultivating light-weight hunches about what will be interesting to you. You are able to skim, scan, and sample before making a full-blown commitment that makes quitting early difficult. And then when you find a hit, you can dive deeply.

Quit Early

This final rule is the one I struggle with the most. If you start reading and the book isn’t landing the way you thought it would, you need to give yourself permission to stop and try something else. It’s a challenge to overcome the sunk-cost fallacy, and in some cases I feel almost a weird sense of betrayal. I committed to read something and then decided to walk away? How dare I!

This is one of the true super powers of reading. Being able to quit early frees one up from the frustration of slogging through books that either aren’t of sufficient quality, or aren’t a good match for your current headspace. This ensures reading is instilled with a constant feeling of excitement. Because if you aren’t “feeling it”, you can reset and reorient.

A Note About Cost

Unfortunately, a lot of this system is predicated on spending money. To which I’d first say, there are a lot worse things you can spend your money on.

However, there are ways to “acquire indiscriminately” on the cheap. There are many places that sell used books for very affordable prices–thrift stores, library book sales, and used-book sellers on Amazon. Oftentimes these used books have an additional character that makes them even more interesting to pick up and peruse. I’ve even noticed that really old works of fiction are sometimes cheaper to purchase on eBay than a brand new copy.

I bought this copy of "The Sea Wolf" on eBay for $9, shipped. It's over 100 years old.

Your public library is also a fantastic resource. I am ruthless about checking out dozens of books from the Los Angeles Public Library. Strangely, there will often be massive queues for digital versions, and several copies of physical books on the shelf, waiting to be checked out. And if you’re interested in a random topic (say Japanese woodworking), odds are in your favor that most titles are gathering dust on shelves.

So that’s it. Build your library, wait to be inspired, and quit when things don’t feel right. And remind yourself everyday how much there is to learn and how little you know.

The First Ten-Thousand

2020-05-19T00:00:00+00:00

There’s something sticky about the number ten-thousand. When you need to pull a large but not-impossibly large number from thin air, ten-thousand fits nicely.

A million dollars? No way. Ten-thousand? Sure.

Creatives seem to gravitate towards the number too.

The first 10,000 pots are difficult, and then it gets a bit easier.
― Warren MacKenzie, celebrated potter

Your first 10,000 photographs are your worst.
― Henri Cartier-Bresson

We all have 10,000 bad drawings in us. The sooner we get them out the better.
― Walt Stanchfield

Whether you’re making pots or taking photographs, you need to get in your reps. How many? A lot. So many that most won’t make it. But not so many to deter those with sufficient persistence.

I was chatting with a friend last week about the trade-offs between quantity and quality in creative output. He described the empowering benefits of a clearly articulated project–you can dive in and move straight for the finish. The opposite is frustrating. Lots of iterations, false-starts, and discarded work. However, the latter can actually be the most beneficial. When we lack clarity, sometimes the most important thing we can do is just start. And the faster we start, the more reps we get in.

When I think about publishing a new post here, I want to have a truly original topic and bullet-proof structure. I need to have the perfect turns of phrase, sources, and pacing. However a bar that high makes it impossible to get to ten-thousand, or even a couple dozen posts for that matter.

But that doesn’t mean that you put out low-quality work either.

I love a story that James Clear shares in Atomic Habits about a college photography class. One half of the class was graded on the quantity of their output–the more photos you took, the higher your grade. The other half was graded on quality–they only needed to take a single photo, and were graded on the quality of that photo.

Guess who had the best photos in this probably apocryphal story? The quantity group. Why? They were getting closer to their ten-thousand.

A key point to emphasize is a rep isn’t just a mindless completion of a task. In the above example, it isn’t sitting on the couch, repeatedly pressing the shutter on your DSLR. It’s engaging in deliberate practice–practice that pushes you a little, stresses you just a bit, and moves you towards a larger goal. Ten-thousand reps of deliberate practice leads to true mastery.

Over the past week I’ve engaged in a little thought exercise about work outputs. What would my skills look like if I did the following:

Wrote out 10,000 product spec documents
Created 10,000 designs in Figma
Wrote 10,000 complex SQL queries
Sent 10,000 persuasive emails (getting close here)
Completed 10,000 interviews (both as an interviewer, and a candidate)
Built 10,000 Google Slides Decks
Drafted 10,000 Strategy docs

There’s obviously a little hyperbole here. But for some of these, they are actually achievable.

Perhaps the takeaway for me is with each thing that I create, that pushes and stretches me, that’s one more rep closer to the goal of ten-thousand. And even if the doc isn’t read, the pot is destroyed, or the photograph is deleted, the practice itself is what is enduring and changes you me the better.

Writing Memos

2020-03-23T00:00:00+00:00

Although I’ve never considered myself a writer, I set a goal in January to become better at “using my words”.

As I’ve struggled through a couple of blog posts, some longish docs at work, and even an online writing class, I’ve grown particularly interested in corporate cultures where long-form writing is integral to the way decisions are made and information is shared.

Amazon is one of the most legendary examples I’ve come across. Their use of internal memos is both prolific and puzzling. It’s an incredible system, but how many other companies could make the necessary changes to support it–without facing internal revolt?

Fortunately, for those not in such cultures, the act of memo writing can be of tremendous personal value. Even if no one else reads them, they clarify thinking, expose gaps in logic, and lay bare facts that can’t otherwise be hidden.

Killing Powerpoint

In 2004, Jeff Bezos killed off Powerpoint at Amazon.

Meetings had been centered around the common practice of presenting a deck, and talking through slides full of bullet points. Bezos found the whole practice deeply unsatisfying. As Brad Stone chronicles in The Everything Store, he decided to put an end to it.

Amazon employees had been using Microsoft’s PowerPoint and Excel spreadsheet software to present their ideas in meetings. Bezos believed that method concealed lazy thinking. “PowerPoint is a very imprecise communication mechanism,” says Jeff Holden, Bezos’s former D. E. Shaw colleague, who by that point had joined the S Team. “It is fantastically easy to hide between bullet points. You are never forced to express your thoughts completely.”

Bezos announced that employees could no longer use such corporate crutches and would have to write their presentations in prose, in what he called narratives. The S Team debated with him over the wisdom of scrapping PowerPoint but Bezos insisted. He wanted people thinking deeply and taking the time to express their thoughts cogently.

These narrative memos were to be read at the beginning of meetings by all attendees, with time reserved at the end for questions–essentially creating a corporate group study session.

The change was not easy and there were growing pains switching from a presentation culture to a memo culture. There were initially no page limits, leading to unreasonably long papers. And many had probably not written anything of substantial length since college.

But over 15 years later, the practice is still in place.

In his 2017 Amazon shareholder letter, Bezos mentioned narrative memos as a practice that helps them continue to have high-standards. It still sounds very similar to what was launched and refined in 2004.

We don’t do PowerPoint (or any other slide-oriented) presentations at Amazon. Instead, we write narratively structured six-page memos. We silently read one at the beginning of each meeting in a kind of “study hall.

The Value of Memos

So what exactly is the value of sitting down and writing out prose?

Writing out prose is hard because it makes gaps in thinking obvious. Written reports require more precision and care than verbal presentations. They impose a level of discipline and raise the bar on the thinking required to create a cogent, and cohesive output–free of inconsistencies that become obvious when putting an entire report to paper. Missing data, unanswered questions, and unaccounted for complications are easy to hand-wave away during a presentation. In a memo, they ring-out like alarm bells.

Memos force well-structured thought. There is really no way to write a great one without clear, structured thinking.

And a great one can’t just be whipped up in an evening. Bezos said in the same shareholder letter that really exceptional ones might take over a week or more to complete.

To me this is the primary benefit of the memo: clearer, more disciplined thinking for the writer. Whether hyperbole or not, Andy Grove writes in High Output Management that “reports are more a medium of self-discipline than a way to communicate information. Writing the report is important; reading it is often not.”

Another benefit is the way that memos can quickly ramp up a group of people on very complex topics, with which they might be unfamiliar. Getting everyone in a meeting the necessary context, background, and data to make good decisions is typically impossible. The fact that Amazon has instituted the narrative memo practice for so long leads me to believe that it is incredibly effective.

How to Use Outside of Amazon

Outside of a company like Amazon, it is unlikely that you will get a group of busy people to silently read your six-page memo.

But I think that’s beyond the point. The process of clarifying your own thinking is a prerequisite for creating any other kind of presentation medium that matches your company’s communication culture. The memo can provide the raw ingredients for a deck, talk, or email.

And ultimately, the end-medium is actually irrelevant. It’s the tip of the iceberg, while deep-thinking forms the ice under the surface–anticipated questions, corner-cases, and data to support positions and hypotheses.

So keep writing even if others won’t read it. And if they will, then make sure you bring the A team memo¹.

A harsh Bezos burn from The Everything Store: [After reading a narrative.] “This document was clearly written by the B team. Can someone get me the A team document? I don’t want to waste my time with the B team document.” ↩

This Is Water

2020-03-18T00:00:00+00:00

I was shuffling through some papers yesterday and came across a copy of David Foster Wallace’s Commencement Speech at Kenyon College. If it’s new to you, I think it’s well worth the 20 minutes to read or watch it. Especially this week.

Like many commencement speeches, it starts off with a silly story.

There are these two young fish swimming along and they happen to meet an older fish swimming the other way, who nods at them and says “Morning, boys. How’s the water?” And the two young fish swim on for a bit, and then eventually one of them looks over at the other and goes “What the hell is water?”

The fish are oblivious to one of the most obvious facts about their reality–to the water that literally surrounds them. DFW’s point is that we’re no different. Sometimes the most glaring truths are ones that are the most difficult for us to see.

These past few weeks, I’ve honestly felt a little scared. But I’ve also been so focused on the news, buying groceries, and staying on top of the next data-filled tweet that I haven’t stopped to really see what’s going on inside me and around me.

I don’t feel like I’m alone in that.

This speech helped me to break out of my default programming just a little, and recenter on things that I choose to think are important.

Default Settings

Our default setting is the way we’re hard-wired to live our day-in day-out lives. It’s a heads down, one-foot-in-front-of the other programming that doesn’t promote taking time to pause and self-reflect, or even question our thinking about ourselves or others.

We have these default settings because daily life can be really hard. Even before the events of the last couple of weeks, days were full of commuting, child-care, health problems–the list goes on.

But these settings are not good for us. We can easily go through life without really choosing what we think about, just constantly reacting with our default programming. I think DFW’s point on the whole matter is that this is no way for us to truly live.

Freedom Through Education

The way to shake us out of our trance is through gaining an education. Since this is a commencement speech, DFW talks about how this happens at a University, but I think it can happen in many places–on a job, through a friendship or new relationship, or even as the result of an impactful event or experience.

An education is not about increasing our capacity to think. It’s about teaching us how and what to think about. It gives us freedom over our thoughts, and an awareness of ourselves and the world around us.

Most importantly, it allows us to decide how to pull meaning from our experience. This is freedom. And many people don’t have it.

There are other side-effects from having this freedom. We can choose to be less arrogant and less self-centered. We can trade being a “lord of our tiny skull-sized kingdoms”, for viewing those around us in a new light. New-found awareness can also lead us to realize how often we’re wrong about things we once thought were certain. Ultimately there’s a humility that can begin to grow if we are free to control our thoughts.

What Will you Worship

With this freedom of thought, we can even change who or what we worship. DFW argues that everyone worships something.

Everybody worships. The only choice we get is what to worship. And the compelling reason for maybe choosing some sort of god or spiritual type thing to worship…is that pretty much anything else you worship will eat you alive.

Money, power, intelligence, or beauty are all aims that can “eat us alive”. I don’t think this is new or even controversial advice. But DFW’s most critical point is that most people don’t realize that they worship these things. Objects of worship are packaged up deep inside our “default settings”.

Freedom of thought means we can realize what it is we worship, and we can decide to worship something else. This doesn’t mean that we need to worship a god per se. But for me, I’m choosing to worship the importance of each person around me. I hope this specific kind of worship leads to more compassion, willingness to sacrifice, and an altering of that lens by which I see the world.

The point is for the free, you can choose. So make a conscious choice. And choose wisely.

This simple awareness–that we have the freedom to control our thoughts, to find meaning from our experience, and to worship what we choose–is so obvious, that you might ask yourself so what?

DFW can explain that much more eloquently than I can:

In the day to day trenches of adult existence, banal platitudes can have a life or death importance, or so I wish to suggest to you on this dry and lovely morning.

And so (speaking to me most of all) be aware, choose how to think, and worship consciously and wisely.

And of course always remember, “This is Water”.

Lessons From Range

2020-03-07T00:00:00+00:00

I just finished David Epstein’s amazing book Range, and have been thinking about it non-stop for the past week.

Range serves as a counterpoint to the “standardization covenant” that is pushed upon us–the idea that it’s better to pursue a rigid goal with a head start, than a winding path of self-exploration. It also dives into how to be a better thinker in environments where feedback is limited or deceptive. Epstein calls these “wicked” environments, and once you start looking, you find them everywhere.

Although I had listened to multiple interviews and even attended a live event where Epstein talked about the book, the concepts didn’t really land until I dug into the book for myself. Perhaps there’s an embedded lesson about great books. Yes, the bad ones can be summarized with a TED talk. But the great ones need 300 pages to adequately share the meat of their message.

The World is Wicked

My favorite concept from Range is breaking the world down into kind and wicked learning environments.

Kind environments provide immediate feedback and allow us to rely on pattern recognition to succeed. Sports like golf or tennis, or structured games like chess are examples of kind environments. You can swing a club, or make a move, and get immediate, non-deceptive feedback.

Wicked environments provide delayed or misleading feedback and have an inconsistent set of rules. Using past experience in these domains will lead to failure. Poker, fire-fighting, and entrepreneurship are all wicked learning environments.

The real world is full of wicked environments–it’s generally not a chess game, or at least not a chess board. The hyperspecialization that is increasingly common today is not the antidote for thriving in a complex world.

Categorical Thinkers Thrive in Wicked Environments

To succeed in wicked domains we need range.

This means we can’t just follow a set of pre-defined procedures and hope for success. Following rote procedures can deceive us into mistaking complexity for cause and effect.

We need to focus on learning and training across a variety of domains. By learning something in multiple contexts, we create more abstract models of concepts. These abstract concepts can then be applied in a larger variety of situations. The more contexts, the more abstract models employed, the more applicable they are across multiple problems. This can be referred to as “categorical thinking” or “conceptual reasoning”.

Although Epstein doesn’t go into the tactics of how to get this breadth of training, the implications are clear. We need to expand our sources of input, the people we talk to, and the domains from which we can acquire knowledge from.

Maximizing Knowledge Acquisition

Even if we are exposed to a broad set of domains, that doesn’t guarantee that we will be able to derive usable knowledge.

The most valuable knowledge is both durable and flexible. Durable means it is sticky. Flexible means it can be applied to many new problems, even in entirely new domains.

Building durable knowledge is a slow process, but spaced-repetition and interleaving (mixed practice) can help with long-term retention. Oftentimes we mistake early success for true learning, when it actually means we are overly relying on procedures to make quick gains, but our performance will flatten out over time. There don’t seem to be many shortcuts here.

Flexible knowledge comes from struggling on our own and seeking to make connections, not memorizing a set of procedures. By decontextualizing concepts, we can form building blocks that can easily be combined with ideas captured in other places.

Ultimately, this helps us to become more T-shaped people: we have a speciality where we feel most confident, but we also draw on learnings from a wide variety of areas that can be applied at will to any problem we encounter.

Now What?

Given that we live in a wicked world that rewards conceptual thinkers, we need to level up our patterns of thought and the way we identify and explore opportunities.

Here are several tactical pieces of advice that I gleaned from the book (either directly stated, or inferred from broader concepts):

Seek a wide variety of inputs - books, people, hobbies, projects, media, and jobs. Remember that “Breadth of training predicts breadth of transfer”.
Maximize your output - you’ll fail more, but you’ll have more opportunities for runaway success.
Become a T-shaped person - great ideas come from T-shaped people, who integrate knowledge from many domains.
Test and Learn - undertake many life experiments and update plans based on learnings from those experiments.
Make short-term plans - don’t stress about not having long-term plans, as long as you are incorporating learnings from your tests.
Don’t feel behind - Just keep experimenting in pursuit of match quality.

Is An MBA Worth It?

2020-02-25T00:00:00+00:00

When people find out I have an MBA, I’m almost always asked about it’s value.

Prospective MBA’s are curious if they should actually go back to school. And nearly everyone else is wondering if an MBA is in reality, a massive waste of time and money.

In my mind, there are two groups of MBA’s, with some fluidity between groups. The first are hill climbers. Hill climbers go to business school to move forward on an existing or predetermined path. They are trying to move up in their same industry, build a network of professional connections, or even switch careers, but in a very prescriptive way.

Random walkers view an MBA as an option with lots of upside. They go back to school to gain new experiences, get exposure to new ideas, and interact with new people. The path it leads them on and the detours they might take are unexpected and often times, unknowable. And the value they get extends far beyond just the narrow focus of a career or vocation.

Hill climbers are often disappointed because their goals are so specific. If they don’t get the bump in title they’re looking for, or find the depth of professional connection, the entire experience can feel like a waste.

Random walkers on the other hand are able to find an incredible amount of value from an MBA. It’s just not always predictable.

As a random walker, although I spent tens of thousands of dollars on tuition, and more importantly, traded away two prime working years, I was able to have many near impossible-to-replicate experiences and change who I am and how I think.

It was absolutely worth it.

The Random Walk

In August of 2013, I was winding down a company with one of my best friends. We had spent nearly the last two years working together, but had realized that it was time to move on from the business and preserve our friendship.

Unfortunately, I had no idea what was next.

Instead of diving into job-hunting, I began toying with the idea of going to business school. Things got real when I bought the serious-sounding “MBA Admission for Smarties” guide on Amazon. Four months after that purchase, I had studied for and taken the GMAT, applied to a handful of schools, and was accepted at and decided on UCLA.

Choosing UCLA created the first big detour that I encountered, even before enrolling in business school. I had to uproot myself from the Bay Area and relocate to Los Angeles, where I had spent almost zero time, knew basically no one, and honestly, had never pictured living. 6 years later, I’m fully committed to LA like I’ve never been to a city before. I met my wife here, started a new career, and love this city. I doubt that I would have been pushed to move, without the forcing function of going back to school.

Before, during, and after starting my program, there were many other detours that I took that changed the way I think and the way I see the world:

I hiked the 200+ mile John Muir Trail with a good friend in the months I had off before school started. Over 23 days I deepened an important friendship and developed an extended love of and appreciation for the outdoors.
I spent two weeks in Shenzhen, China, exploring electronics malls, prototyping a hobby device I had dreamed up, and meeting interesting people. It changed my perspective on China and manufacturing broadly.
I was able to travel throughout Southeast Asia on work-study trips. I visited auto part plants in Thailand, walked through clothing factories in Vietnam, and saw business in the developing world through entirely new eyes.
I spent spring break in Hawaii with a great friend where I hiked to the top of a volcano, got stung by a sea urchin, and strengthened my love for reading.
I was able to intern at Twitter where I met amazing people, and worked on a really fun project.

Sure, none of these detours were impossible to take while having a normal job, but the act of going back to school provided so many opportunities to have these unexpected, and life-changing experiences.

Self-Awareness by Chance

My second year of business school, I took a class that really unlocked how I see the world called People in Organizations. It is consistently one of the most difficult classes to get into. The format is simple–for a semester you sit in a circle with 10-15 of your peers and answer questions like, “How did your parents make you this way?” or “What are you not getting from your significant other?” Essentially, it’s group therapy for many who have never gone through therapy in their lives.

This class changed the way I view myself, the way I analyze my behavior, and lens through which I view the world. As an example, I previously struggled with an intensely strong desire to be liked by others and was constantly worried about what others thought about me. I’m now able to identify these thoughts of worry, put them in proper context, and not let them throw me off as I go about my daily life.

Becoming a Self-directed Learner

During winter semester of my second year, I was driving from LA to San Francisco and was listening to an audiobook to pass the time. When I arrived, I stopped the book and had a horrible realization: I had been listening for 5 hours and I couldn’t remember a single thing. I couldn’t even remember the exact title of the book (Thinking Fast and Slow). This was an ephiphany moment.

Fortunately, it was the catalyst that changed how I consume and capture information.

I spent the remaining months of school reading voraciously and setting up a system to save insights from the things I read. I started reading physical books, printing out assigned papers and cases, and collecting ideas in Evernote.

This system has allowed me to read over a hundred books since then, take careful notes, and share my learnings with others. While this breakthrough didn’t need to happen in the context of business school, I don’t think I would have had the mental space or time, to both identify a new learning system, and put it in practice.

New Models of Thought

While changes of thought are hard to quantify and difficult to identify when manifest, I feel like my strategic thinking skills have improved.

What do I mean by strategic thinking? To me it’s a combination of consulting frameworks, game theory, and fundamental analysis. It’s viewing business or organizational problems with a new set of tools, and providing structure and a repeatable process around that thinking.

Running through business school cases helped me a lot. Cases can be dangerous because you can easily fall into a bad habit of quickly jumping to conclusions without reconsidering fundamental assumptions–businesses aren’t deterministic simulations, and running one isn’t as simple as following a formula. However, being able to quickly assess the strengths and weaknesses of a business or tactic has significant value.

I also had some fantastic professors that modelled both critical and original thinking: Keith Chen, Derek Alderton, Terry Kramer just to name a few. Interacting with good thinkers is something that is difficult to do with the busyness of day-to-day life. I feel very fortunate to have been exposed to so many wonderful teachers during my time at UCLA.

Meeting Great Friends

Finally, I was able to make some truly wonderful friends–people that are genuine, smart, and inspiring.

It’s challenging to make friends after college, or even a first job. Being in a place with hundreds of other people your age, many of whom have just relocated just like you, makes establishing new friendships natural and unforced.

I believe that good friendships are so hard to come by that any process to cultivate them is deeply valuable.

In short, I gained so much value from MBA, I can’t imagine wishing for an alternative path.

The hill-climber, random-walker lens helps me make sense of the many people who question whether the decision to go back to school was a good one. And helps me process my own personal experience that was so overwhelmingly positive.

While everyone’s journey will be different, if you embark on the random walk of an MBA, and embrace the randomness, you won’t be disappointed.

Read to Write, Write to Learn

2020-02-09T00:00:00+00:00

[Originally posted on Medium]

Four years ago, I had a reading epiphany. I realized I wasn’t retaining anything from the books I read or listened to and decided that drastic action was necessary. I came up with a process that I thought was sure to make my reading more productive: I started reading physical books, began bookmarking and highlighting liberally, and most importantly, turned those highlights into hundreds of pages of typed notes that I saved and shared with friends. Collectively, I’ve spent thousands of hours on that process. And last week, I realized that my process was failing me.

The catalyst was a short, self-published book called How to Take Smart Notes. This book provides a detailed system on how to read, take notes, and write using the Zettelkasten (slip-box) method developed by German Sociologist Niklas Luhmann. Luhmann used this system to generate prolific, high-quality output during his lifetime.

While the technical specifics of the slip-box system are interesting, the higher level principles were what truly resonated with me — perhaps because I’ve spent so much time doing things wrong, and this system clearly articulated my shortcomings. Fortunately, it focuses on the same goals I’ve always been seeking: using reading to improve my thinking and expand my ability to learn.

The goal of reading is writing

While I didn’t connect the dots previously, the biggest break-though idea for me is that writing should be the output of my reading. Writing demonstrates understanding. It is the ultimate medium and facilitator for research, learning, and study. You can’t think systematically without writing.

Completing a book feels good and hitting your Goodreads challenge for the year seems like a nice accomplishment, but without turning that reading into tangible output, you’re effectively running in-place — expending a lot of effort, but not making any forward progress.

Writing is the natural end-state of book notes. If notes aren’t to be used for writing, collecting them becomes a pointless chore.

Good notes are essential for great writing

You can’t really know anything if you just remember isolated facts and try and bang ’em back. — Charlie Munger

Taking good notes is a prerequisite for great writing.

Over the past several years, I’ve made the mistake of copying down long quotes and passages. I thought that getting as much raw material into Evernote was going to benefit me in the long run. It seemed that by hoarding as many quotes as possible, I’d always have the perfect one, ready at hand.

Unfortunately, copying down someone else’s words doesn’t make them your own. The key to taking good notes is capturing ideas in your own words, and unlocking them from the context of their specific usage.

When you copy down quotes, you skip the step where you actually need to think about what something means. Rephrasing in your own words helps unlock the idea from that specific context, and ensures that you understand the topic. If a note isn’t decontextualized, you can never think beyond it; it’s cemented into that context forever and you can’t do anything to it. Copying quotes leads to a patchwork of ideas — not well-developed thoughts.

When notes are stripped of context and put into your own words, they can be elaborated upon by meaningfully connecting one idea to another, sometimes in novel or unexpected ways.

Notes belong in an external thinking system, not an archive

Once you take good notes, they need to go into an external thinking system. An external system (or external scaffolding) to think and organize your thoughts is critical; it overcomes the limitations of our brain, which is subject to the constraints of our memory and our ability to retrieve ideas. The external system becomes your idea factory where notes and thoughts go in, and ideas come out. There is also a powerful compounding effect because as we add more ideas, there are more possible connections, and more possible output.

It’s important that only high quality notes get put into this system. If you over-capture, you dilute the good ideas with insignificant ones, and never attain a critical mass of notes. This system is a tool for thinking, not an encyclopedia, so completeness doesn’t matter. Don’t build up an archive of isolated encyclopedic facts; build a network of ideas.

Otherwise, you’ll just have a pile of notes in an archive that are only useful in a single context — essentially a “graveyard for thought”.

Write bottoms-up, not linearly

Since writing is an open-ended process, it isn’t something you can be overly prescriptive about. If you pick a topic and then try to find evidence for it, you’ll inevitably ignore or dismiss any disconfirming ideas.

The beauty of the external thinking system is that topics can organically form as notes and ideas begin to cluster together. These topics and questions can then be analyzed and answered in the whitespace of daily life. And they can be further refined as we add more content and notes to our thinking system. This helps to avoid confirmation bias. It also helps us to come up with novel and exciting new ideas.

The best part of this system is that clusters of notes can be used to build out a rough draft. So that when you write, you can avoid the dreaded blank page.

Embrace the virtuous cycle

This process is a self reinforcing one. By becoming better at identifying good ideas from reading, we increase the quality of our notes and writing. This elevates our thinking and ultimately expands our learning opportunities. Which makes us better readers, with increased capacity for thought.

Instead of just accumulating knowledge, we can become truly different people.

Which to me, is the promise of reading fulfilled.

Reflections on Reading in 2018

2018-12-28T00:00:00+00:00

Developing a better reading practice was a huge accomplishment for me in 2016, and I’m happy to still be going strong two years later. I ended up reading 24 books this year (vs. 21 in 2017 and 37 in 2016). I know that counting books read is a silly metric, but there’s something satisfying in seeing proof that I’m still prioritizing reading in a meaningful way.

My note taking process didn’t evolve too much this year—I experimented with a new note-taking app, but ended up using Evernote again, writing up notes and sending them out to friends and family. My personal commonplace book is expanding nicely.

For 2019, I’d like to start a personal project around reading that doesn’t require me to read more to scale. This means no writing detailed reviews, posting things read to Instagram, or blogging. Ultimately this could look like some kind of app, focused on improving book discovery. I’ve got a couple of good domains sitting around, so my chronic domain hoarding may finally starting to pay off…

On to things I learned:

Information mediums influence the way we think, at a biological level.
The importance of memorization.
Sleep is one of the most important drivers of good health, and we fail miserably at getting enough of it.
When it comes to usability, don’t make me think.
“If you’re going to eat shit, don’t nibble.”
Use temporal landmarks to help you focus on the big-picture and achieving your goals.
You are the CEO of your own career and you need to “cultivate a habit of constantly questioning your work situation.”
“The beauty of a notebook is that it indulges provisional thoughts, half-finished ideas, unpolished sketches, and drafts for treatises not yet refined.”
“Put more wood behind fewer arrows.”
Time is not fungible—”all our activities are equivalent or interchangeable once they are reduced to the abstract currency of clock time” is an untruth.
“To be great, one must be a great writer.”
“Chicken is boring. Chefs see it as a menu item for people who don’t know what they want to eat.”
The Anna Karenina Principle - “success actually requires avoiding many separate possible causes of failure.”
Embrace boredom and “learn to see [it] as an opportunity to find something interesting within yourself.”
“Embrace regular, thoughtful conflict as the basis of effective negotiation.”
“Nothing fails like success.”
Attention is precious and we should not part with it “as cheaply or unthinkingly as we so often have.”

2018 Reading List

The Shallows: What the Internet Is Doing to Our Brains by Nicholas Carr
Desert Solitaire by Edward Abbey
Digital Gold by Nathaniel Popper
The Hard Thing About Hard Things by Ben Horowitz
Why We Sleep by Matthew Walker
Don’t Make Me Think by Steve Krug
We Should All Be Feminists by Chimamanda Ngozi Adichie
When: The Scientific Secrets of Perfect Timing by Daniel H. Pink
Only the Paranoid Survive by Andy Grove
Conspiracy by Ryan Holiday
12 Rules for Life: An Antidote to Chaos by Jordan Peterson
Leonardo da Vinci by Walter Isaacson
Levels of the Game by John McPhee
Red Notice by Bill Browder
Shop Class as Soulcraft: An Inquiry into the Value of Work by Matthew B. Crawford
Ogilvy on Advertising by David Ogilvy
Guns, Germs and Steel by Jared Diamond
Measure What Matters by John Doerr
Kitchen Confidential by Anthony Bourdain
Reclaiming Conversation: The Power of Talk in a Digital Age by Sherry Turkle
Tortilla Flat by John Steinbeck
Never Split the Difference by Chris Voss and Tahl Raz
Crucial Conversations by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler
The Attention Merchants by Tim Wu

Square Cash vs. Venmo

2018-09-04T00:00:00+00:00

I recently saw these tweets by Keith Rabois:

Assuming this was investor hyperbole, I did some more digging and was surprised to learn that Square Cash is doing incredibly well. And since both services are offering physical cards I decided to request both and test them out.

I received the two cards on the same day. Each envelope contained a debit card attached to a single sheet of paper. I scanned both sheets of paper side-by-side to highlight the stark contrast in approaches.

Click image to view a larger version

Square limits itself to 12 words to drive users to activate their card. Venmo uses a wall of text, and includes details around how to use the card, how to reload it, how to track usage, and even what to do if you lose it. The activation details are hidden in the first bullet.

Given the incredibly high cost of getting users to order a card, delivering the card, and the subsequent increase in customer LTV post-activation, high activation percentage (number of activated cards over number of cards mailed) has to be an critical metric.

The distinctly different approaches leave Venmo feeling more like a traditional bank, with Square Cash looking more like the upstart. Venmo has clever copy, but seems to miss the point of the mailer entirely. I could completely be missing a critical insight—for example, longer form copy could lead to higher activation rates—but that feels unlikely.

Venmo has had a huge head start. But Square Cash seems poised to continue to chew away market share.

My Best Reading Year Ever

2017-01-01T00:00:00+00:00

2016 was the year that I really discovered books.

It wasn’t that I didn’t read before. I read in the usual places–on planes during cross-country flights, on trains while commuting, and at home in bed, knocking out a couple of pages while half-awake. And of course I listened to my fair share of audiobooks. All of that reading (and listening) gave me a great deal of satisfaction, which manifest itself in ego-boosting, affirmations like: “You’re a smart guy. You read books.”

But things changed early in the year. I had just finished the long, round-trip drive from Los Angeles to San Francisco and had spent the entire 12 hours in the car listening to Thinking Fast and Slow. The book had come highly recommended and listening while driving made me feel productive. I was using my time efficiently!

However, after returning home, a discouraging reality set in. I had listened to a good portion of the book, and I couldn’t tell you a thing about it. Nothing. Major themes, key ideas–I couldn’t even tell you the title without half-wondering whether I had butchered it beyond recognition. The words had flowed in one ear and out the other, barely pausing to register on what sits between. I was the ultimate passive reader, just checking off titles instead of truly weighing and considering.

Anytime I’ve made a change in my life, I can usually pinpoint the source of motivation. But determining what gave the motivation its intensity is more difficult. I can tell you I was really bothered by my sorry state of reading and the motivation to change this was profound.

I went to Barnes and Noble and purchased a physical copy of Thinking Fast and Slow, because I wanted the book that day. If audiobooks didn’t work for me, then I was going to go full analog, back to paper and ink. Shortly afterwards, I went on a week-long vacation to visit my friend Jeff in Hawaii, and over that week, I read carefully and methodically. I looked up words I didn’t know. I marked concepts and ideas that both interested and confused me. I reread passages to ensure I fully grasped concepts, premises, and findings. I deconstructed the book and made it my own. At the end of the process, multi-colored sticky notes were exploding from the pages.

I went through thousands of sticky notes this year.

Once I was done reading, I started writing. I wrote down quotes that I liked. I wrote down thoughts that impressed me and definitions that I wanted to remember. I summarized each chapter and then summarized the whole book. I even recorded an audio summary that I uploaded to YouTube, with the thought that I could listen to it when my recall of the book began to fade.

And the whole crazy process seems to have worked.

Thinking Fast and Slow was the first book I’ve read in years, where I could tell you what the basic premise was. I could tell you the difference between quick gut-reactions, and slow, more methodical reasoning. I could cite examples and quotes from the book I found valuable. I could explain the various cognitive biases listed in the book. In short, the book was mine. I had made it a part of me. I weighed and considered, and took what I wanted and pondered what challenged my thinking.

Since that week in March, I’ve read 37 books, all physical copies. For each book, I took detailed notes and recorded an audio summary. While I’m happy I’ve read a lot this year, I’m most proud of the fact that my new reading process has proved repeatable. I can approach a subject I’m interested in or a work I want to understand, throw myself at it, and come out with a deep understanding. Even areas that were intimidating and honestly, that I thought were beyond my understanding, now seem within reach.

So what did I learn in 2016?

I’ve learned how to truly read books again.

I’ve learned to make my life more antifragile.

I’ve learned how to better identify errors of judgement and choice.

I’ve learned the value of educating myself.

I’ve learned the importance of standing on my own legs.

I’ve learned the value of meaning.

I’ve learned that everything that happens in life is the best possible thing (or that I wish that to be true).

I’ve learned that history is not determinstic.

I’ve learned about the dangers of cargo cult thinking, and the importance of being curious.

I’ve learned about the chaos of the mind, and the power of finding flow in all aspects of life.

I’ve learned about the marvels of hard work.

I’ve learned how to better manage my time, capture thoughts, and free up room to exercise creativity.

I’ve read some amazing memoirs.

I’ve learned a thing or two about writing.

I’ve learned about negotiation, game theory, and optimal stopping problems.

I’ve pondered questions of life and death.

2016 was my best reading year ever. And I’m commited to make 2017 even better.

Rethinking The Personal Narrative

2016-06-18T00:00:00+00:00

If I had never dropped out, I would have never dropped in on this calligraphy class, and personal computers might not have the wonderful typography that they do. Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backward 10 years later.

— Steve Jobs, 2005 Stanford Commencement Speech

We’re all familiar with the narratives around famous entrepreneurs. Every experience it seems, no matter how insignificant (like a calligraphy class), led to the great success they see today. These stories are told and retold and began to crystalize into a mythology about how someone’s life unfolded.

But what happens when we can’t suspend disbelief, when the story just seems too clean, too linear? Whether it’s hearing someone talk about “how they got here” in an interview, or listening to a business leader “talk about their background”, the crisp connection of events, jobs, and choices have always made me feel like there’s something missing. I notice myself fighting against feelings that the speaker is being disingenuous or even deceitful.

I think this stems from an incorrect assumption about the role of the personal narrative. A personal narrative is not a personal history, because experience can be framed in innumerable ways. A personal narrative is a tool for one’s own use, a way of marshaling our energies towards the goal in front of us and calming the chaos of our mind. It is not an objective recounting of facts or a retelling of our resume. A personal narrative is a way of telling a story that puts structure around our entropic lives and careers.

When a personal narrative carves a path that ends in our current job or endeavor, it helps to provide incredible resolve. The “why” of where we are today is an answered question. That clarity is something that frees the mind to focus on more pressing problems, instead of constantly trying to justify why we belong.

This means that a personal narrative can be fluid. Provided we make reasonable decisions, it’s a way to accept our current situation and to find opportunities for flow in whatever we are engaged in. This isn’t to say that there shouldn’t be periods where we seek to objectively evaluate where we are in life and whether or not we need to make course corrections. But we shouldn’t be reticent to edit our past as we age and gain more experience. The subjectivity of the narrative is what makes it so powerful — we can use it to frame ourselves in ways that we might not yet be, but that we can grow into.

Life is full of uncertainty and unlimited choices. Maybe all paths lead to the top of the mountain, but there are a million ways to get there. If we view our lives as a connection of random events it can be overwhelming. Mainly because it makes our existence seem devoid of meaning. A sense of purpose is an incredibly powerful way of coping with this uncertainty.

As I’ve thought through narratives, I’ve resolved to celebrate the personal narrative. Now instead of trying to poke holes, I want to ask the following question: “How does this narrative serve to support you in your current goals, and what does it tell me about how you want to see yourself?” Certainly this is a question that I should ask myself first.

I don’t yet have a satisfying personal narrative. Sure, I can rattle off where I’ve worked and what I’ve done, but there are periods in my life that I struggle to put into context. It’s liberating for me to think that this is totally fine. And knowing that I have control over both how I “tell my story” and how I change it in the future is something that is truly empowering.

Can we speed-listen and still understand?

2016-06-02T00:00:00+00:00

[Originally posted on Medium]

Over the past couple of years, I’ve started to consume more and more information through spoken audio — the explosion of new podcasts and the production of great audiobooks has made listening to that content an irreplaceable part of commuting, exercising, or relaxing.

Very early on in my listening journey, I encountered a temptation that all podcast junkies are forced to face: the speed slider. In Overcast, I can increase the speed to a blistering 2x. The Audible app supports 3x speed, which is approaching “Motormouth” John Moschitta territory. For podcasts, I now hover around 1.7x and normal speed has become nearly unbearable.

Pick your poison

As I’ve grown accustomed to higher speeds, I’ve wondered if the typical listener of audiobooks/podcasts can listen at greater than 1x speed without significant comprehension loss. At what point are speed-listeners short-changing their comprehension? Based on the research I was able to find, not only is it possible to comprehend spoken audio at significantly higher-than-normal rates of speed, the average person can train themselves to improve comprehension and actually prefers listening at a rate of speed that is higher than normal.

We are amazing listeners

Starting in the late fifties, researchers began experimenting with time-compressed speech and measuring the ability of subjects to comprehend material at high rates of compression. They determined that the average adult can readily comprehend spoken audio at 2X speed or at a compression rate of 50% [1]. This roughly corresponds to 275 words per minute. Although compression rate is a more helpful guide, words per minute is a good proxy that keeps things simple. Given that the typical conversational speaking rate ranges from 140–180 words per minute, we usually are able to comprehend even the fastest talkers [2].

Now how does this translate to audiobooks and podcasts? A middle value of 150 wpm seems like a reasonable estimate for the average audiobook, and aligns with the research I did. However, because podcasts are more tightly edited and are much more conversational, my hunch was that the wpm rate would be on the higher end. This was proven out through analyzing transcripts for several podcasts I listen to. I selected several episodes on YouTube that have automatic captions enabled and then wrote a ruby script to parse the subtitle files. Here’s a graph for Dan Carlin’s Hardcore history:

I calculated WPM rates for each minute throughout the podcast — I’m sure there’s a better way to do this.

We see that episodes hover in the 140–190 wpm range. At a 1.5x speed, we’d see roughly 240–285 wpm which is close to the 275 wpm ceiling. Provided that the material being listened to isn’t overly complex (e.g. a conversational podcast), it is well within the average person’s ability to process a typical podcast at 1.5x speed.

We can improve our listening comprehension

Another remarkable discovery is that our ability to listen and comprehend at high rates of speed is a highly improvable skill. According to time-compression research, with as little as 8–10 hours of training, we can comprehend material at “substantially higher speeds” than 2x [3]. While I’m not clear on the specifics of what kinds of training would facilitate significant improvement, it seems reasonable that listening to one season of Serial (or any enjoyable podcast) at faster than 1x could yield increasing comprehension benefits for the listener.

This is further emphasized in a study that looked at blind students and their preferred rate of listening to college lectures. Researchers found that their preferred rate ranged from 236–275 wpm [4]. Given their focus on listening as a primary sensory input, they were able to comfortably process information far faster than most people can comfortably speak. Presumably this was a learned skill, based on necessity.

We have a natural preference for speed

Finally, it is comfortable on some level to listen to spoken audio at a faster than normal speaking rate. In the last study I mentioned, sighted students were also tested and their preferred rate of listening was 212 wpm (82% compression). Once we realize we can “increase the communication capacity of the ear”, it becomes pleasurable and natural to listen at a higher rate of speed.

What now?

Given that speed-listening is a valid way to increase our learning per minute spent, we can view it as a valuable tool at our disposal. However, when comprehension or pure enjoyment are ultimately the goal, the speed with which we listen should be adjusted to meet our own personal objectives. To modify a line from Mortimer Adler’s How to Read a Book:

“Every [podcast] should be [listened to] no more slowly than it deserves, and no more quickly than you can [listen to] it with satisfaction and comprehension.”

This quote is a great guide as I choose what to listen to and how to listen to it. It’s in the back of my mind when I play Never Let Me Go at an enjoyable 1x speed. And it clears my guilt when flying through Marc Maron, Tim Ferriss, or Ben Thompson at 1.7x. And most importantly, it’s what causes me to sometimes stop the audiobook and pick up a good old fashioned paperback.

Sources

[1][2] Cognitive Factors in Auditory Performance : Context, Speed of Processing, and Constraints of Memory — Arthur Wingfield, Journal of Audiology (1996)

[3] Microsoft Research: Time-Compression: Systems Concerns, Usage, and Benefits

[4] Techniques, Perception, and Applications of Time-Compressed Speech — Barry Arons, MIT Media Labs

Thoughts on China and 15 things I learned in Shenzhen

2015-09-22T00:00:00+00:00

For much of this year I’ve been fascinated with Chinese technology companies. This first started when I saw MyIdol, a quirky Chinese app for building funny avatars, made it into the top ranks of the US app store, without being localized. In other words, an app with no English instructions, menus, or content was so compelling that everyone from Miley Cyrus to John Mayer was talking about it and using it. In the past couple of months, there has been much more interest in WeChat as a platform, DJI as a global brand, and Didi Kuaidi as the goliath that will prove to be to much competition for Uber to handle.

My sense is that Silicon Valley grossly underestimates China’s ability to create transformative consumer products that will be adopted in the West. WeChat is a great example–the discussion is more about how their platform approach shapes Facebook’s Messenger strategy, and not about why WeChat could be the next WhatsApp. Tech journalists acknowledge the success of Chinese companies, but fail to accept the extent to which they can be competitive in the US (e.g. Barrons bizarrely comparing Alibaba to a struggling eBay).

With these ideas in mind, I was able to spend the last two weeks in Shenzhen, China (my first time in mainland China!). Shenzhen borders Hong Kong to the North and is the 5th most densely populated city in the world, with a population of over 10 million people. It serves as a massive manufacturing hub and is the site of “FoxConn city” and the Huaqiangbei electronics market. Here are some observations (mainly for me), about what I learned and what I saw:

1. The smartphone supply chain is incredible - with hundreds of millions of devices being sold each year, the cost for memory, chips, sensors, cameras, and all sorts of components are coming down due to massive scale.

Smartphone cameras at Huaqiangbei

2.There is huge opportunity for companies that can tap into existing supply chains - in the same way that portable chargers seem to have capitalized on cheap lithium ion 18650 batteries, or that selfie stick remotes capitalize on cheap bluetooth chips, the opportunity seems to be around tapping into the economies of scale that have been created by other larger companies.

The remains of bluetooth remotes I bought on Taobao.

3. Prototyping a product in Shenzhen is great, but ‘making it’ is tough - with many factories and suppliers close by there are fewer delays and prototyping can happen much more quickly. However the expectation that you can show up with a rough sketch and get something built quickly for large scale manufacturing is unrealistic.

In roughly a week, I was able to print a PCB, order components on Taobao and get a simple board assembled for a little hobby project I found on Github.

4. People know what circuit boards are - people are familiar with electronics and nobody is going to confuse a PCB with some wires with a bomb.

5. eBikes and and eTrikes change last mile delivery in a dense city - electric vehicles are everywhere all the time and made deliveries through the city simple and fast.

6. WeChat simplifies communication (and pretty much everything else) - everyone uses WeChat. There is no confusion around how to connect with friends or businesses. WeChat also changes to B2C communication. It’s realtime, unlike email which is much slower.

This vending machine lets you pay with WeChat or Alipay using a QR code

You can connect to Wifi at the Shenzhen airport using WeChat (add the airports official account to get a Wifi access code messaged to you).

7. Taobao is incredibly powerful - Taobao is Alibaba’s C2C marketplace (similar to eBay). You can buy nearly anything on Taobao with fast shipping and incredible prices.

Some Taobao purchase I made

8. The Firewall is a huge issue - Yes you can VPN around to get access to blocked content, but there is never a guarantee that your VPN will work 100% of the time.

9. Western services generally offer a second-class experience - given the issues with VPNing, it makes much more sense to use China-based equivalents to Gmail, Dropbox, and Hangouts.

10. Bing search is a joke - I haven’t used it in a while, but since it’s not blocked in China I gave it a try for the couple of weeks I was there. Never again.

11. Baidu is always incredibly fast - every time you think the Internet speed is horrible, you can load up Baidu and see how fast other services could be. This may be one of the reasons so many Chinese developers were hit with Xcode malware recently. Downloading Xcode binaries from Baidu has to be far faster than going through Apple’s servers.

12. Cheap shipping presents massive opportunity - given the low costs of manufacturing, if you can ship product globally for a reasonable price there’s lots of potential (e.g. Wish)

13. Lots of construction, but exceeds demand - tons of buildings going up, but many remain vacant.

14. Translation apps are getting pretty good - Baidu translate is almost good enough for most situations. Live audio translations work decently well.

15. China is very ethnically diverse - many people assumed I was Chinese, which really surprised me (I’m half-Japanese). Many different types of people.

Reddit's tax on Amazon purchases

2014-09-08T00:00:00+00:00

Yesterday I saw the following sponsored ad on the reddit homepage.

The link leads to the following Amazon product page (with an affiliate id in the URL):

Having done a bit of reddit advertising in the past, I thought it was pretty clever–;a thumbnail of a hapless lobster and intriguing copy, begging for a click. The real surprise was seeing 334 comments on the post. That kind of engagement is incredibly rare for reddit ads, so I dug into the comments to see what was going on.

Sorting posts by date, it became clear that this ad had been running for a while (since July) and that it was using reddit’s Amazon Associates ID (for Amazon’s affiliate program).

Now here’s the craziest part, the actual product is over $1400. The conversion rate on this product is guaranteed to be 0%, barring a very, very drunk shopper. However, by creating a catchy ad, reddit is able to cookie tens of thousands of Amazon shoppers. This means that reddit will be credited with an 8% commission on purchases made by those users in the next 24 hours.

I’m certainly not faulting reddit for trying to make money, but these types of campaigns are just bizarre. They make absolutely no incremental revenue for Amazon and are essentially taxing Amazon for the purchases made by redditors that mindlessly click on the ad.

Reddit could do commerce so much better, especially with Amazon. This is barely a step up above cookie stuffing. I hope that with the new raise, they’ll be able to focus more on how to integrate commerce with their amazing content. It won’t be easy, but attempts like this just make it feel like there is little direction to current efforts to monetize on the ad side.

Why Messages in iOS 8 will make driving safer

2014-06-03T00:00:00+00:00

Messages in iOS 8

I just downloaded the iOS 8 beta and after playing around, I can’t help but feel that audio messages will be a huge deal for a lot of people. Yes it’s a feature that’s existed in many messaging apps, but I think that including it natively will really encourage strong adoption, especially where it matters a lot: when driving.

Obviously driving and texting isn’t safe, but I see it every single day. With audio messages, it’s a simple two taps (tap and hold to record, and then tap to send). Reading messages is still a danger, but hopefully replying by voice will make the roads safer for everyone.

CA Lottery: Play Responsibly

2014-03-09T00:00:00+00:00

The Mega Millions jackpot just hit $309 million, and it’s great timing because March is National Problem Gambling Awareness month!

The design of the Mega Millions ticket is interesting: it deceptively features a “Play Responsibly” banner down the side of each ticket, but by not clarifying what that means, they can simultaneously (1) claim they are warning consumers about the danger of their product, and (2) maintain ticket sales, by making the warning as unclear as possible (and thus non-alarming).

For Your Security

2014-01-22T00:00:00+00:00

For your security, we may ask you these security questions to verify your identity.

Security questions don’t make me feel more secure. Many times, the answers are either a simple Google search away, or they don’t even apply to me (although I wish I did have an older sibling and that they had a charming nickname). Most of the time, I’ll forget what I entered, if the answers are case-sensitive, and who exactly was my favorite pet.

I’m sure there’s research that supports using security questions. I’m sure that security questions can improve internal KPI’s around compromised accounts and show that support time spent goes down when they are used. But they don’t make me feel more secure.

As a public service, Capital One has compiled a highlight list of bizarre security questions–and built it into their product!

Google+ vanity URLs make me like Google+ less

2013-10-30T00:00:00+00:00

I just received this email from Google+, informing me I can get a custom URL for my profile:

Clicking the Get URL button took me to my profile with this modal:

In case you can’t tell, the URL is not changeable–my custom URL has been “preapproved”.

If you meet the eligibility requirements, you can get a custom URL for your Google+ account or page. This means **you can choose one of the custom URLs Google preassigns to your Google+ profile or page**. Depending on the preassigned custom URL, you may also need to add a few letters or numbers to make it unique to you.

via: Google+ Help

Facebook, Twitter, and LinkedIn all let users customize their vanity URL. Unfortunately by adding a feature where choice is eliminated, this change feels less like an improvement and more like a constraint. They managed to put a negative spin on a potentially positive (and much needed) change.

Pay with Amazon in the Wild: The Clymb

2013-10-27T00:00:00+00:00

I’ve been very interested in online payment systems as of late–with the Braintree acquisition by PayPal, international expansion by Stripe, and the launch of Cash by Square, the space is definitely heating up.

In particular, Amazon’s new(ish?) Login and Pay with Amazon product seems to provide merchants with some great benefits: a simplified checkout process that leverages a user’s existing Amazon account information, mobile-optimized flows, and access to Amazon’s fraud prevention. However, merchants who adopt Pay with Amazon are implicitly letting their customers become Amazon’s customers, in effect helping to further support the stratospheric growth of ecommerce’s Goliath.

I recently came across a company using the Login and Pay feature (The Clymb), and wanted to take a closer look at the mechanics of the integration. Side-note: If you aren’t familiar with The Clymb you should really check them out–they are doing awesome stuff with outdoor gear/apparel.

To start, I selected some shoes, added them to my cart and headed to the checkout page. Keep in mind that The Clymb requires users to be logged in to view sales, so I already have a Clymb account.

Since I’ve never made a purchase before, I’m greeted with a wall of inputs–billing address, shipping address, and payment information. Beneath all that is an expandable option for “Checkout with Amazon”.

Clicking the “Pay with Amazon” button brings up a pop-up to sign-in to my Amazon account.

After signing in, I’m greeted with a much friendlier checkout page:

All of my addresses and payment methods are preselected for me to review. All I need to do is confirm and then place my order.

It’s a really fantastic process, and I’d imagine it would work great on both smartphones and tablets. Again, this is my first purchase on The Clymb and the process couldn’t have been easier.

However, I think the most telling part of the checkout process is the email confirmation.

This is a standard Amazon email receipt–no mention of The Clymb or the fact that I purchased from a 3rd party (other than the fact that it came from Amazon Payments). If nothing else, this reinforces that although merchants are getting great benefits from using Amazon for payments, the customer’s ties to Amazon are further strengthened. If I want to return my shoes, I might even go to Amazon first because that’s where the email receipt came from.

Like all online merchants that choose to do business with Amazon soon realize, the company makes for a strange bedfellow. I think The Clymb strikes a good balance here–not overly focusing on the Amazon option, but providing it for customers a secondary option. It would be great to see some internal numbers on how this impacts cart abandonments, repeat purchases, etc.

Overall, I can see some strong benefits for online retailers. As a consumer, I hope to see more options to checkout with Amazon in the future–as far as I’m concerned, the fewer companies that need to safeguard my payment information, the better. As an observer of online retail, I hope that businesses are able to intelligently use this service to complement their existing checkout flows–improve their conversion metrics, while at the same time making sure they cement me as their customer and not just another of Amazon’s 200 million strong flock (…of which I am a happy member)

Update:

I just received an email confirmation from The Clymb–looks like they’re doing their part :)

The pain of two clicks

2013-10-15T00:00:00+00:00

I’m an active user of Google apps and I spend much of my day inside of Gmail. I grew used to having a dark navbar at the top of the screen, containing direct links to other Google services, particularly Calendar.

With a recent redesign, those links were placed in a drop-down identified only by a confusing grid icon. The Calendar link is placed in the bottom right of the app grid, beneath other, less-popular products (I’m not sure if this positioning varies between users).

For some reason, this change really frustrated me. I mean, it’s only an additional click right? There are variety of workarounds from bookmarks, to keeping my Calendar constantly open in a browser tab.

I think my frustration boils down to the way this change was messaged by Google:

Welcome to the new way to find your favorite Google products.

A casual reader might incorrectly assume that new implies more efficient, more convenient–a better experience for the end user. From what I can tell, all this change accomplishes is freeing up space for a large icon to be placed next to each Google product. Maybe there is some end-user benefit to associating logos/icons with products. If there is, I have yet to discover it. However, I can respect that there are trade-offs between design and usability.

Perhaps more frustrating is their use of the word favorite. Google+ is not one of my favorite Google products. The Google Play store isn’t particularly useful since I don’t own an Android device. And Google Search and YouTube? Chrome makes going to the Google homepage seem silly. In this context, favorite actually has no connection to my preferences–it’s a selection and ordering of products that match Google’s business objectives.

One extra click isn’t that big of a deal. I mean it requires maybe an extra second or two of work. But every time I have to make that extra click I’ll be reminded that Google makes changes that aren’t going to help me. And those clicks add up.

How LinkedIn penalizes its users

2013-06-21T00:00:00+00:00

The more I use LinkedIn, the more I’m baffled by the way that they deceptively encourage people to pay for their premium service. Case and point: today I was researching a freelance videographer. Here’s his profile when I’m logged into my LinkedIn account:

Uh oh! Apparently full profiles are only available to premium account holders. Let’s check the same profile in an incognito window:

Like magic, his entire profile is visible. What’s happening here? Everyone without a LinkedIn account can view this users full profile. The only people who can’t are LinkedIn userswho aren’t paying them $24.99 a month. I’m being penalized for having an account (and tricked into thinking I need to pay for information that is a Google search away).

While its true that some people hide information from their public profile (making a premium account useful to some people), I think it’s incredibly deceptive for LinkedIn to hide information that users have stated should be shown to everyone.

Why Amazon Fresh is about more than groceries

2013-06-04T00:00:00+00:00

According to Reuters, Amazon is planning on rolling out it’s grocery delivery service to several new markets: LA and SF this year and potentially up to 20 additional markets in 2014.

This is an absolutely huge deal and an opportunity that extends way beyond groceries. I’m convinced that this is going to be one of Amazon’s most successful business units and here are 7 reasons why:

1. Amazon has tested this for 5 years

Amazon has been testing Amazon Fresh for the last 5 years in the Seattle area. This has given them ample time to work out potential problems with processes, scaling, and business economics. They are not racing to follow a competitor–they are fully aware of the challenges they’ll face. Given that Internet sales tax laws seem imminent, the timing seems perfect to start expanding (tax nexus no longer matters for them).

2. Amazon owns its own fleet of trucks
Amazon doesn’t appear to be leveraging courier services or hiring drivers to use their own vehicles. This gives them incredible control over their delivery fleet and a flexibility that will be tough for others to match.</p>

3. Amazon controls its own inventory
Amazon is not selling for someone else. Unlike Instacart or Google Shopping Express that piggyback off of existing grocery/retail locations, Amazon has their own warehouses and stock. By disintermediating the grocery store, their margins will always be better than what a 3rd party can offer.

4. Inventory is managed based on the delivery model
Amazon’s former head of global fulfillment technology, Nadia Shouraboura, has argued that anyone not managing inventory based off of a warehousing paradigm, will not succeed:

Logistics experts, including Shouraboura, argue that such a strategy will never work if same-day delivery takes off. Stores are organized according to a different logic than warehouses, they say. If same-day orders start pouring in, stores won’t be able to keep up — and in-store customers could get trampled. http://www.wired.com/business/2013/04/store-of-the-future/all

Again, this hurts anyone who needs to piggyback off of existing stores (i.e. pretty much anyone not at Walmart/Amazon scale).

5. Amazon can delivery non-grocery items
Amazon can easily bundle non-grocery items, with deliveries. Each grocery delivery becomes an opportunity to upsell the customer on goods that a grocery store does not carry. Delivery times can be dramatically reduced for items that would normally be shipped from a distant warehouse.

6. Amazon is solving last-mile delivery
There is no good last-mile delivery option in the US. If Amazon succeeds with Amazon Fresh, they will be building incredibly valuable infrastructure that they can leverage across their other businesses. Imagine a future where the Amazon driver is a more familiar face in your neighborhood than the UPS guy.

7. Amazon can run this at a loss
Like their hardware businesses, Amazon Fresh can be run with very aggressive economics because of the positive impacts it can have on their other businesses. Perhaps only Walmart would be able to compete here.

If I were involved in this space (Google, Walmart, eBay), I would be very nervous. They will need to move incredibly fast to stay relevant.

A quick redesign thanks to Twitter Bootstrap

2013-05-09T00:00:00+00:00

My friend Tito has a small biotech hardware company he’s run on the side for several years. He wanted to do a quick refresh of the website so we took a crack at a redesign and after a couple of hours of work, here are the results:

Before

After (the redesign)

What really blew me away was how powerful Bootstrap is for whipping together a simple, static website. Basic layout, buttons, cross-browser compatibility, modals–most major components just work and are bundled for easy use. Tito had been using Wordpress to manage the site but it was way to bloated and overly complicated for his use-case.

I wonder if Wordpress will adapt to create a more lightweight version to serve a lot of the smaller, single-author projects being produced, or if another tool will eventually supplant them? Maybe Weebly?

Direct Mail Optimization: ING DIRECT

2012-11-02T00:00:00+00:00

I’ve received two pieces of direct mail recently from ING DIRECT, inviting me to open an online checking account. It’s interesting to see how optimization of direct mail parallels web optimization.

While the majority of the text is similar, the value propositions are very different.

Craigslist testing mobile and tablet versions

2012-06-25T00:00:00+00:00

Hell hath frozen over. Craigslist started testing mobile and tablet-optimized formats of their website starting last week.

On account pages, you can see the following links at the bottom of the page:

Clicking one of the options sets a cookie that dynamically modifies the page source whenever you visit a Craigslist page (this means that the classic version is visible briefly, before the elements are rearranged).

What’s the verdict? The mobile version actually looks pretty useful–more readable text-sizes, better layout and navigation on a small screen (scrollable images, etc.). However the tablet version is awful. They try to use panels to break out category navigation, search results and listings, and the result is pretty much unusable. Hopefully it will go through a couple more iterations as I could see it being very helpful going forward. I’d have to imagine that there is a pretty large contingent of Craigslist users who browse exclusively on mobile devices/tablets. If you have any feedback, be sure to let Craigslist know:

https://forums.craigslist.org/?forumID=8374.

And if you want to explore some more of the technical details, here’s the Javascript they’re using to modify the page source:

http://craigslist.org/js/formats.js

Now on to the screenshots…

Mobile Home Page

Mobile Search Results Page

Mobile Listing Page (Inline in search results)

Tablet Homepage

Tablet Search Results Page (Only 5 listings visible at a time–hooray!)

Tablet Search Results Page (Ok, a little cooler when you’re actually looking at a listing)

Tablet Browsing (Portrait)

Tablet Optimized Posting Flow (sorry iPads, no pics)

How many emails do you send a day?

2012-06-04T00:00:00+00:00

How many emails do you send in day? If you use Gmail/Google Apps Mail, you can now easily find out detailed usage stats. There’s currently two methods for quickly pulling out stats: (1) Google’s Account Activity Dashboard or (2) the Gmail Meter.

Google Account Activity Dashboard

To get a high-level overview of your inbox habits, simply go to your Google Account Activity Dashboard to opt-in. You’ll get a report sent to you by email that summarizes your sends, emails you’ve received, and top contacts. It provides a nice summary of your activity. If this feels insufficient (as it did to a data nerd like me), you’ll need to graduate to Gmail Meter.

The Data Dump (i.e. Gmail Meter)

Two weaknesses with the Account Activity Dashboard are you can’t really get access to the data used to generate the report, and the time ranges for the report aren’t easily customizable. These shortcomings are both addressed with Gmail Meter, an awesome Google Apps script that processes all of your email for a given time range.

For instructions on how to set it up, check out the following tutorials (it only takes 5 minutes max and is as simple as setting up a Google Docs spreadsheet):

After you’re done with setup (and wait a while for processing–5 minutes for every 100 emails processed), you’ll have a spreadsheet with the date sent, subject, to/from/cc fields, word count, and label information for every email sent or received in the time period. You’ll also have some great summary stats, which are used to produce a report that gets automatically mailed out every month. Here’s some sample graphs:

I was pretty surprised by my pathetic email output. For some reason I feel like I send a lot more email than I actually do. Maybe others are like me? I’m hoping to increase my output over the upcoming month–having automated reports is definitely going to make holding myself accountable much easier.

How to have personality: Lessons from Trader Joe’s 1.4 million price tags

2011-05-06T00:00:00+00:00

Trader Joe’s knows marketing. They don’t want you to know this however. Their displays, signage, and advertising (including their kitschy “Fearless Flyer” newsletter) all convey the message that Trader Joe’s is just like the simple grocery store of yesteryear–healthy food, friendly staff, and a store that has a personality.

Nothing demonstrates this better than the beautifully hand-drawn price tags that adorn every product display in the store. That’s right folks–in this era of nearly ubiquitous digitization, Trader Joe’s hand-draws every single price-tag. Keep in mind it’s not just numbers and text, but often artistic elements, depictions of food, and other designs. They are amazing.

Based on some numbers sourced by Fortune Magazine, there are roughly 4000 SKU’s (stock keeping units) in a typical Trader Joe’s store. As of April 2011, there were 355 Trader Joe’s locations across the US. That means that there are over 1.4 million hand-drawn price tags–price tags that will change and need to be recreated based on season, promotion, and price fluctuations.

Who makes them?

According to an employee I spoke with at a San Francisco location, there are 4-5 artists on staff for that given store, who work full-time on producing artwork. I had a friend ask for a job application, and the manager said they were on the lookout for artists that do good, fast work. Wait. Trader Joe’s is actively looking for artists? Isn’t the job of creating in-store art best left to a graphic designer at TJ’s headquarters?

Why hire artists?

One of the key elements of any Trader Joe’s location is it’s strong ties to the local community, which furthers it’s ‘small-town grocery’ feel. Artists are able to incorporate depictions of local geography, places of interest, and subtleties that an employee in Monrovia, California (Trader Joe’s HQ), would have never heard of.

Having a personality is part of the plan

Trader Joe’s is a Fortune 500 giant. They generated sales in excess of 8 billion dollars in 2009. However, you don’t get that feeling inside a store. The illusion is a cleverly orchestrated masterpiece. I don’t say this as a critique of their model, because I am a loyal customer that eats up every bit of their marketing. They could clearly afford to follow every other major grocery chain, but their decision to hire local artists is an expensive, conscious, and brilliantly astute one.

Now back to you: Does your company have a pulse?

If a company with 5500 employees can feel human, then your startup of 10 or 5 or maybe just 1 person needs to feel human too. I don’t think that customers necessarily want to find new friends through the businesses they work with or shop at, but they certainly want to make sure they see signs of life. If you want some more examples of online companies that do this well, here’s a brief list:

Zappos - a joke of the day over the phone. Just call (800) 927-7671 and follow the prompts.
Woot - pretty much any writing they do is the best. For a stellar example see Woot Minions.
Groupon - before they did Super Bowl commercials, they did this.

Any more suggestions? Post a comment or send me an email.

AvantLink Stats Chrome Extension

2011-03-24T00:00:00+00:00

AvantLink is an Affiliate Marketing network–think an intermediary between merchants who want to have an affiliate program and publishers who want to make money off of their content. If you need some more context about affiliate marketing, this video may provide some further clarification. As a long-time affiliate on the AvantLink network (i.e. somehow who makes affiliate commissions through merchants working with AvantLink), I’ve grown religious in checking my stats. Thanks to an Android app, I can see my daily commissions whenever I have 10 seconds to pull out my phone.

While AvantLink has made some cool tools for Firefox users, I primarily use Google Chrome, and there wasn’t anything to allow me to get my stats fix while I was on my laptop (other than actually disrupting my workflow to login to the AvantLink site). I spend a night whipping up a Chrome extension and figured that since I got some good use out of it, I might as well improve it to the point that others can use it too.

FEATURES

Here’s a basic rundown of what it does:

Your daily sales are overlaid on the extension icon
The daily sales icon-overlay updates every 15 minutes
You can view all the stats you can view with the AvantLink mobile app simply by clicking on the extension icon.

INSTALLATION

You can install the extension by visiting the following crazy URL: https://chrome.google.com/extensions/detail/hkbnfcfgobgepemjabhnfkhnllnphodc

You’ll need to enter your Affiliate ID and API Authorization Key to configure the extension, but both are stored securely on your local machine and are never logged externally. Also keep in mind the that AffiliateReport API module (which the extension uses) has a limit of 1000 calls per day. If you get a little click happy, you may find your access temporarily disabled (I’ve spent a while debugging the extension–read clicking many times–and haven’t yet run into an issue).

If you find this useful, or have any feature requests, please let me know and I’ll try and add them in a new release.

San Francisco's Tsunami Risks: The Facts

2011-03-20T00:00:00+00:00

Due to several sensational news articles in recent days (most prompted by the tragic events in Northern Japan), friends and family (read my mom) have asked me about the dangers of living so close to the coast, and particularly about the risk of a giant tsunami. I currently live a little over 2 miles from the Pacific, and wondered exactly what the possibility was that my apartment would be taken out by a giant wave. I was also tired of all the hearsay about the risks. After sitting down for a couple of hours and doing some serious googling, I decided to write down what I found–hopefully others in San Francisco and even California will find it useful.

FIRST, MY FINDINGS

Yes, San Francisco is at risk. No, I (living in the Sunset) do not face any inundation risk. Continue reading for the details.

WHAT IS A TSUNAMI

Let’s start here because although slightly embarrassing, my knowledge of a tsunami up until recently consisted of the following facts: (1) Tsunamis are giant waves, (2) they can be deadly. Not too impressive.

Typically, a tsunami is generated by an underwater earthquake, where one plate is subducted, and another is pushed upward, causing a large wave. Local tsunamis can also be generated by strike-slip faults (where plates slide left-to-right), where underwater landslides result in large waves, although this is less common (the San Andreas fault is an example of a strike-slip fault) [2]. Waves generated by tsunami’s are obviously much more powerful and are shaped differently than normal, wind-generated waves [1].

Source: http://www.seismic.ca.gov/tsunami.html

CALIFORNIA TSUNAMI HISTORY AND GEOGRAPHY

California is no stranger to tsunamis, as it faces risks from both local and distant tsunamis. In the state’s recorded history, there have been 82 possible and confirmed tsunamis that have reached California shores. Nearly two-thirds of those events were the result of distant sources [4]. In the San Francisco Bay, 51 tsunamis have been recorded since 1850 [5]. The worst tsunami event in California occurred in 1964 as the result of a magnitude 9.2 Alaskan earthquake. The ‘64 quake produced waves between 10-16 feet along the California, Oregon, and Washington coasts and killed 12 people in Northern California. [1] [4]

California’s greatest risk is from the Cascadia Subduction Zone, the fault between the Juan de Fuca and North American plates. Located off the Northwest coastal US, a Cascadia earthquake would create giant waves that could hit the coast much faster than waves generated from distant events. There would be less time to warn those at beaches and in low-lying areas. The last Cascadia earthquake occurred in 1700 and resulted in waves of 15 feet reaching Japan (which is similar to the height of waves that reached African shores after the Sumatra earthquake) [1].

Source: http://www.usgs.gov/science_impact/risk.html

There is a lot of seemingly conflicting information about the potential and probability for tsunamis generated by a Cascadia earthquake. Wikipedia states that the probability of a large Cascadia earthquake occurring in the next 50 years is between 10-14% but I had a hard time pinning down reputable sources. Needless to say it poses a significant risk.

COMPUTER SIMULATIONS

In March 2010, the NOAA Center for Tsunami Research published a special report, modeling forecasted tsunami impacts on the City of San Francisco. In case you were wondering, NOAA stands for the National Oceanic and Atmospheric Administration–a government body that also oversees the National Weather Service and that is basically tasked (among other things) with keeping the general public safe from weather related disasters. The NOAA has actually published many reports for dozens of cities along the western and eastern coasts of the United States (you can find a report for you specific city at http://nctr.pmel.noaa.gov/forecast_reports/ in an easy to navigate Google Map).

The report uses existing tsunami data to create an inundation model for San Francisco–basically, what size waves will reach the shores of the city. The model was calibrated with data from historical tsunami events, and then dozens of scenarios were analyzed. The report found the following:

Sensitivity study results show that the San Francisco Bay area is at greatest risk from a tsunami generated in the eastern portion of the Aleutian-Alaska-Cascadia Subduction Zone. A maximum wave of 7.6 m is predicted for a tsunami generated in Aleutian-Alaska-Cascadia segments 29–38…Tsunami waves from the northern portion of the Kuril and Japan subduction zones and those generated along the southern portion of Chile pose a signiﬁcant risk to the San Francisco area with waves greater than 1 m predicted. [6]

Different Scenarios Tested along the Aleutian-Alaska-Cascadia Subduction Zone:

Potential wave heights

This report shows that maximum wave heights actually reaching the shores of San Francisco would be generally no greater than 3-4 meters. It also confirms that that the Cascadia Subduction Zone poses significant risk (unfortunately, a scenario was not tested which simulated a quake occurring directly on the Cascadia fault).

INDUNDATION MAPS

In recent years, California has produced inundation maps that show potential water levels in a tsunami event. Unfortunately they seem rather unscientific–according to the California Geological Survey, “We used one elevation for the whole state. We just drew a line at 30 feet up from sea level.” Fortunately, most wave surges wouldn’t come close to this level. [7]

To view inundation maps for your area, you have two options:

If you discover that you live in an inundation zone, you’ll need to make preparations for what you’ll do in the event of a disaster and plan an escape route. Fortunately is looks like the Inner Sunset (where I live), is incredibly safe at roughly 200 feet above sea-level (to see elevation levels for where you live, you can use MyTopo’s interactive maps).

IS SAN FRANCISCO AT RISK?

The short answer is definitely yes. However, only a few portions of the city face inundation, even from a massive wave. Although you should exercise caution when near the shore, and should definitely have an evacuation plan in place if you live in an inundation area, destruction from land-shaking earthquakes is a much larger concern for most San Francisco residents.

HOW TO PREPARE

There are many resources available online for preparing yourself in the event of a tsunami. The USGS has produced an informative video on tsunami preparedness specifically for Northern California (go to 4:58 for some particularly fine acting):

You can also use the following helpful resources:

AlertSF - Sign-up for SMS alerts based on the San Francisco neighborhood you live/work in
72hours.org - Find instructions on what to do in various disasters and what to include in an emergency pack/go-bag (translated into 5 different languages)
Surviving a Tsunami - Read an interesting USGS report, which uses lessons from past tsunami’s to instruct those at risk on how to survive in the event of a tsunami

I’m sure I haven’t covered all of the resources out there, so let me know if I missed something (or especially if I made a factual error).

SOURCES

[1] http://www.seismic.ca.gov/tsunami.html [2] http://quake.abag.ca.gov/tsunamis/ [3] http://quake.abag.ca.gov/wp-content/documents/ThePlan-C-2010.pdf [4] http://www.seismic.ca.gov/pub/CSSC%2005-03%20Tsunami%20Findings.pdf [5] http://www.baycitizen.org/disasters/interactive/mapping-risk-tsunami-plans-ba… [6] http://nctr.pmel.noaa.gov/forecast_reports/final_reports/03_SanFranciscoCA_33… [7] http://news.discovery.com/earth/california-tsunami-threat.html

Setting up an Amazon EC2 instance: A beginner's guide

2011-02-24T00:00:00+00:00

I recently decided to move a project onto Amazon’s EC2 from a dedicated box I’ve been running for a couple of months. Although it was initially intimidating, there are a wealth of blog posts, tutorials, and guides that really hold your hand as you get used to Amazon’s setup.

I heavily consulted the following three guides (keep in mind that I decided to go with an Ubuntu install)–strangely the second post is quite similar to the first.

These tutorials walk you through the process of setting up an EC2 account, installing EC2 command-line tools, authentication, and loading an AMI (Amazon Machine Image) onto your instance. Since the tutorials do a great job of taking you through the above tasks, I’ll leave the majority of the explanation to them. However, I will give you a high level overview of each task so that you can get a feel for the roadmap.

Create an EC2 account

Simple and straight-forward—sign up for an AWS (Amazon Web Services) account, and then create an EC2 account. The process is very easy–note however that you will be asked to complete phone verification before your account is setup.

Setup Authentication

You’ll need to create an X.509 certificate and download both the resulting private key file and the X.509 certificate file to a safe place on your local machine. No passwords are exchanged—to learn more about how authentication works with EC2, be sure to read-up on Public-key cryptography.

The only gotcha’s I had in the entire process had to do with how I named my private key files. For the sake of simplicity, follow the Ubuntu guide as far as naming and locating your private keys.

Install the EC2 command-line tools

A simple install will allow you to interact with your EC2 instances from the command-line. There is a web-based GUI you can use, but the command-line can help you control your instances much more quickly.

Choose and load an AMI

Loading an Amazon Machine Image is surprisingly simple, especially if you decide to go with Ubuntu. Ubuntu maintains a list of official AMI’s–I went with 10.04 LTS, and the AMIs can be viewed at http://uec-images.ubuntu.com/releases/10.04/release/. Loading your selection is as simple as locating the AMI ID and installing it from the command-line.

SSH into your instance

After opening a port for SSH on your instance, you should be able to successfully access your instance from the command-line, and interact with it like any other remote machine.

That’s it! At this point, you can either press forward by either assigning a static IP and further configuring your instance, or by terminate your instance—both are explained clearly in all three guides. The whole process is surprisingly simple, and most of the legwork is a one-time deal. Once the basic setup is out of the way, creating new instances can be done in a matter of minutes.

URL Structure for Usability and SEO

2011-02-18T00:00:00+00:00

Maybe it’s my love for all things organization, but well-formed URLs are just plain satisfying. Unfortunately for me, I’m revisiting an old project and my half-baked URL structure is quite the Frankenstein monster. Rehabing it hasn’t been fun, but I’ve learned a bit about what I’d like to do going forward, when I start a new project.

Properly formed and descriptive URLs are important for three primary reasons:

They will help users find and share the content they are looking for
They will improve your SEO (and thus help users find your content more easily)
They will help you sleep better at night. Seriously, a well thought out URL design will allow you to make changes and additions later on without fear of disaster or confusion

In planning out my new URL structure I’ve identified several points that should help anyone looking to acheive the three aims above.

Keep URLs short and sweet

Short URL’s force you to be as descriptive as possible, removing extraneous words. Short URLs will help users to better share your content and otherwise navigate your site. Think that adding a couple of extra words into your URL will help boost your SEO? The days of using keyword stuffing to improve search engine rankings are over. Matt Cutts advises that 4-5 words is a “natural” length and that any more words diminish the value of the additional words. I don’t think Google could make it any more clear when they state, ”a site’s URL structure should be as simple as possible.”

Words & Numbers

Words are always going to trump numbers, so don’t put them in your URLs when possible. Compare the following links for the same backpack from two different online merchants, REI and Backcountry.com:

Confusingly, the REI link tells the user that they will be viewing product "795624”, while the Backcountry link clearly shows the shopper what product they will be viewing. Although the REI link is a bit cleaner, don’t forget big G’s recommendation: “When possible [use], readable words rather than long ID numbers”. Enough said.

Reduce directory depth

Directory depth refers to the number of directories beneath the root URL that content exists. An example of a directory depth of 1 would be http://yourdomain.com/sub-directory/. Rand Fishkin said it best: "A URL should contain no unnecessary folders (or words or characters for that matter), for the same reason that a man’s pants should contain no unnecessary pleats. The extra fabric is useless and will reduce his likelihood of impressing potential mates.“

Measure twice, cut once

Modifying your URL structure after the fact will result in pain, frustration, and frequent face-palming. Before embarking on nearly any project, you’ll need to sit down and give serious thought to URL design. Some even feel that URL design should be the, "first discussion of any startup directly after the idea is solidified.”

YOU MUST give serious thought to your URL structure–do your research, look at what competitors are doing, and make a concious decision about how your URLs will be structured. Don’t rely on a framework, or decide to just back into one option. If you do,you’ll regret it.

Some final fine tuning

Use puncuation in your URLs–hyphens are better than underscores
Don’t use upper-case letters. Rand Fishkin recommends that, “If you have a lot of type-in traffic, you might even consider a 301 rule that sends any incorrect capitalization permutation to its rightful home.”
If you use many parameters in your URLs consider eliminating non-essential parameters and making them as descriptive as possible. Also be sure to modify your robots.txt file to prevent the GoogleBot from indexing all of the variations of URLs with parameters attached.

Remember, a wise man once said, “If you fail to plan [your URLs], you plan to fail.” Don’t forget to give serious thought to URL structure the next time you start a new project–you won’t regret it.

How to form a California LLC by yourself (Part 2)

2010-08-18T00:00:00+00:00

[Disclaimer: I am not a lawyer, nor do I aspire to be one]

I’m excited to finally be able to write this follow-up post. I submitted my Articles of Organization at the end of April, and received back filing confirmation in mid-July. It was a long wait and unfortunately, there are still a couple of more steps to complete. The good news is however, I’m almost there!

Ground to Cover:

Complete the Statement of Information (LLC-12)
Obtain an EIN from the IRS
Pay the Franchise Tax
You did it!
Additional resources

Complete the Statement of Information (LLC-12)

In the documents that I received back from the Office of the Secretary of State, there was an addressed envelope and a copy of FORM LLC-12, the Statement of Information. The instructions for completing the form are included and it is pretty straight forward. You’ll need to enter the name and address of the office of the LLC, the CEO of the LLC, and all of the managers of the LLC. You’ll also need the name and address of the Registered Agent (what you entered on the Articles of Organization). Keep in mind you’ll need to send this form within 90 days of the initial filing (of the Articles of Organization) to avoid a $250 penalty. Given the slow turn-around time, this doesn’t give you a big window in which to file this form. Complete it quickly and include a $20 check when you mail it off.

Obtain an EIN from the IRS

Before you complete the next step (pay the Franchise Tax), you’ll need to get an EIN (Employee Identification Number) from the IRS. This is surprisingly painless. You simply go to the IRS website (http://www.irs.gov/businesses/small/article/0,,id=102767,00.html) and click Apply Now. You’ll be directly through a series of questions and you’ll be able to get your EIN instantly. Navigating through the questions took me less than 10 minutes.

Pay the Franchise Tax

By far the most painful part of forming an LLC in the state of California is paying the hefty Franchise Tax. Each year, you’ll need to pony up $800 for the privilege of doing business in California. You’ll need to pay this by the 15th day of the fourth month of your taxable year (April 15th if you are operating on a calendar year). In the year that your LLC is formed, you’ll need to pay by the 15th day of the fourth month after the LLC commenced business. To pay the the tax, you’ll need to complete the LLC Tax Voucher (Form FTB 3522). To fill it out, make sure you have both your Secretary of State (SOS) file number and your newly acquired EIN handy. Once you complete the voucher, mail it in along with a check for $800.

You did it!

Well it took a couple of months, but that’s pretty much all there is to forming an LLC in California. If you are forming an LLC with multiple members, you’ll still need to adopt an Operating Agreement that has been reviewed by a lawyer. If you are operating a single-member LLC, you should be good to go.

Additional Resources

How to form a California LLC by yourself (Part 1)

2010-04-30T00:00:00+00:00

[Disclaimer: I am not a lawyer, nor do I aspire to be one]

I recently decided to take the plunge and incorporate–partially so I can have rad business cards, but mainly for legal and tax reasons. While operating as a sole-proprietorship has worked well so far, I run the risk that I could be held personally liable in the event of a nasty lawsuit. It also forces me to comingle my personal and business finances (which makes accounting and taxes difficult).</p>

Ground to Cover:

Why an LLC?
Where to incorporate?
Should I pay LegalZoom $150 to mail a letter? No.
Prep. work
Completing the Paperwork
Pay your fees and send
How long will it take?
Next steps
Additional Resources

Why an LLC?

After some research both online and offline, I finally settled on a single-member Limited Liability Corporation (LLC). For me (a single founder), an LLC was a great choice for several reasons:

LLC’s provide me with sufficient legal protection–as long as I’m smart about how I operate, I will face no personal legal liability
Pass-through Federal tax treatment—my taxes will remain doable and I won’t be doubly taxed (i.e. only once at the personal-level, and not at the corporate level)
Since I don’t intend to seek VC funding (or any sort of significant outside funding for that matter), the shareholder restrictions of an LLC aren’t onerous enough for me to consider a C-corporation.

Where to incorporate?

Once I decided on an LLC for the business structure, I had to decide which state to incorporate in. Since I am a resident of California and am doing business there, I decided to register in California. Before doing research, I was contemplating registering in Delware—as far as I know, for California residents, this is a bad idea and will not prevent you in any way, shape, or form from paying franchise taxes and fees to the California state government. Bottom-line: if you live in California and are registering an LLC, do it in California.

If you are unsure at this point if an LLC is the right choice for you, I highly recommend consulting the book, The Entrepreneur’s Guide to Business Law. Chapter 4 is devoted to the pro’s and con’s of each type of business structure. It is a great resource for pretty much any serious startup founder (or startup employee for that matter).

Should I pay LegalZoom $150 to mail a letter? No.

Robert Shapiro would have you believe that you need his help to register your LLC. In fact he will do this for the low, low price of $150. Why this service thrives is beyond me. You will only need to file 2 forms and you can do everything in less than an hour. Please, do not use LegalZoom–you can do all of this by yourself.

Prep. work

Before you start filling out forms, you’ll need to answer 3 questions:

What will you call yourself? You’ll need to do a search to ensure that your company name hasn’t already been registered. The State’s website has a search function at http://kepler.sos.ca.gov/. Although it is pretty limited, it should be sufficient for most purposes—I picked a name for which I also own the dot-com and that made me feel a little bit more sure that it was unique.
Who will serve as the Initial Agent for Service of Process? This basically means, who will receive all legal communication for the company. The registered agent must be a resident of the state and have a physical address in the state (no post office boxes). While you can use yourself, I would strongly advise that you go with a registered agent service. This service is provided by companies who will collect documents on your behalf and forward them to your home address. I went with InCorp Services, but there are numerous options to choose from. The service should run you around $100 a year, and save you the hassle of changing your address if you move. You’ll need to sign-up beforehand so you can get the company’s address to use when you file the registration paperwork.
How many owners the company will have? If you’re a one-man show like me, this should be simple :-)

Completing the paperwork

The paperwork to register an LLC was initially intimidating—the instructions provided on the state’s website aren’t the best. While there are many books written to guide you through the process, it honestly isn’t that complicated. Let me restate that—it is surprisingly simple.

The first form you’ll need to complete is FORM LLC-1. The form along with instructions can be downloaded as a PDF from the California State Government website. There are only several places on the form that you’ll need to enter information—the instructions do a thorough job of covering what you’ll need to fill out.

Box 1 – Enter the name of the LLC you’ve decided on. Remember that you’ll need to add the proper ending to the name of the company (e.g. Limited Liability Company, LLC, or L.L.C.)
Box 2 – You can ignore this
Box 3 & 4 – Enter the name of your registered agent. If it is an individual (such as yourself), enter your full name in box 3, and your address in box 4. If you are using a registered agent service, enter the complete company name in box 3 and leave box 4 blank (the address for the company should be on file with the state)
Box 5 – Indicate how many managers your LLC will have
Box 6 – You can attach additional documents if you’d like to. I did not.
Box 7 – Date and Sign

Pay your fees and send

Once you’ve completed and signed FORM LLC-1, wipe the sweat from your brow and make a couple of copies—the state will certify up to two copies without charge. Write a check out to the Secretary of State for $70, and put the check and FORM LLC-1 along with the copies in a stamped envelope and send it to the address specified on the instructions.

How long will it take?

Unfortunately, at the time of this post the turnaround time on Articles of Organization filings are about 40 business days (or nearly 2 months). This is not normal and you can thank government furloughs for the delays. There are options for fast-tracking your filing, but this can potentially be very expensive.

Next Steps

Once you have successfully filed your Articles of Organization you’ll need to do the following:

File FORM LLC-12 within 90 days. Failure to do so will result in a $250 fine.
Pay a franchise tax payment of $800! Yes I know, it’s steep, but it’s the cost of doing business in California.
Adopt an operating agreement. For a single-owner, this isn’t as critical, but if you have multiple owners, this is a must. This document does not need to be filed with the Secretary of State–you can consult an attorney or use a boilerplate operating agreement, however the former would probably be most advisable.

I am still waiting to hear back on my Articles of Organization, so I’ll cover these three points in more detail in an upcoming post.

[UPDATE: The second post is now finished]