Favorite things, day 5: Alaska Airlines


What’s not to like about an airline that more or less runs like the good old days of air travel? Courteous staff, clean planes, great terminal facilities at San Francisco and Seattle, where I travel the most. Their social media support is great as well.

Unlike any other carrier I’ve flown, they proactively try to make things better when things go wrong.

A few of the highlights:

  • $25/2,500 mile baggage guarantee. If your bags don’t show up within 20 minutes of reaching the jetway, you get your choice of $25 credit or 2,500 frequent flier miles. (Pro tip: always take the miles. They’re worth more than the $25.)
  • Once when I had an extended mechanical delay, I received an apology email and a voucher before the plane touched down. I didn’t even have to ask.
  • In weather delays, gate agents have organized games in the gate area to keep passengers occupied.

The frequent flier program is the best in the industry. It used to be that frequent flier programs existed to reward loyalty of members. Most airlines now view them as short-term profit centers. Every opportunity to make money off the loyalty program. they jump at.

Alaska still has a traditional program that is based on miles flown. The underlying economics that Alaska has chosen build loyalty for the long term versus extracting as much revenue as possible in the short term. (A very quaint philosophy in today’s business world.)

I just finished up a round-the-world mileage run just to get top tier elite status on Alaska. I flew Mumbai-Hong Kong-San Francisco-London-Johannesburg-Victoria Falls and then the reverse to San Francisco.

I wouldn’t have done that on any other carrier.

There are elite benefits that are unheard of. MVP Gold and MVP Gold 75k can change paid tickets without any fees. That flexibility has a lot of value for me. (Southwest allows anyone to do this, but that is an extreme outlier; Southwest doesn’t have a route network that works for me.)

The Achilles’ Heel in Alaska for me is that their transcontinental flights do not have lie-flat beds, unlike American, Delta, jetBlue and United. But I’ve gotten to the point in my travels that flying 6 hours coast-to-coast is old hat.

Especially if you’re on the West Coast, Alaska should be your pick.



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Favorite things, day 6: First Republic


I had somehow left my card in Hong Kong and was on my way to Zimbabwe. ATMs are common, but few businesses take credit cards. So I needed cash. I emailed by banker and she offered a couple of options.

She said, “If you need cash now, we can work through the Visa network and get you a bank that can give you cash today … or we can get new ATM cards printed and sent to you at your hotel in Zimbabwe. Pick which is best for you.”

“I can wait for the card. Please send it. Can you also send some water bottles? I keep losing those things.”

“Let me check.”

“They’re worried that the water bottles will slow things down because they’d have to go through customs. We printed the cards, here’s the tracking number. We’ll get you those water bottles when you’re back home.”

This has been a typical experience for me at First Republic. It’s one of the few large institutions I work with where I feel like a person, not a number. I never have to provide an account number. My banker knows me. Not having to deal with annoying phone menus is reason enough. In 2019, who calls to get their bank balance? But many banks make you say representative four times.

You never have to deal with an automated system here. Stop by the bank and chat with your banker, or email or call your banker. If you stop by, you can get fresh-baked cookies. Not sure if you have to be a customer to get free cookies, but I don’t think they’ve carded me for cookies. (I opened my account in Oregon, so I do most of my transactions by email.)

First Republic has treated me better when I had $5,000 on deposit than Chase or Wells with more than $500,000.

The star account here is their ATM Rebate Checking. A $3,500 minimum average balance gets you a solid checking out with unlimited worldwide ATM rebates. Some months, when I’ve been traveling extensively, I’ve received more than $30 in rebates.

There’s a detail buried in that sentence that illustrates the philosophy. Most banks use the minimum balance, not the minimum average balance when calculating fees. That means that if at any point in the month, you had a balance of $3,499.99 or less, you’d get hit with the monthly fee. Because FR uses the average, dipping below for a day won’t trigger the fees.

Instead of the gotcha, they play fair.

I’ve also never had to pay for things like cashier’s check or notary services.

Whenever I get service this good, I’m always suspicious. I know some companies have me flagged in their CRM systems as an influencer. (I had amazing service from Comcast!) But the feedback I get from friends who are also First Republic customers is that they also get similar service.

First Republic’s slogan is, “It’s a privilege to serve you.” That sounds like one of those made up slogans which falls apart when given any scrutiny.

This is a rare case when it isn’t.

Deadweight loss quotient: This should only be a gift to yourself, or spouse/significant other with their consent. Though I’m sure that if you want to give a CD full of money, the deadweight loss there would be zero.

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Favorite hotels from around the world

Here’s a list of my favorites.

St Regis Vommuli Resort


This is in a class by itself.

St Regis New York

St Regis Princeville, Kauai (now the Princeville Resort)

St Regis Dubai (now the LXR Habtoor Palace)

St Regis Deer Valley

St Regis Florence

Ritz Carlton Kuala Lumpur

Andaz London

Gritti Palace, Venice (Sadly, seriously damaged by recent flooding in Venice.)

The Gwen, Chicago

The Nines, Portland

Fairmont Orchid, Big Island, HI

Ritz Carlton San Francisco

Fairmont San Francisco

Manele Bay hotel (Now Four Seasons Resort Lanai)

Andaz Maui

Fairmont Maui

Royal Hawaiian, Honolulu 

Moana Surfrider, Honolulu

Park Hyatt Sydney

Kimpton Canary Hotel, Santa Barbara

Hotel Bristol, Vienna

Convento do Espinheiro, Portugal

Tambo del Inka, Peru

Loi Suites, Iguazu Falls, Argentina

And here are some, that despite the brand name, are just blah.

Four Seasons Austin

Andaz Wall Street

Waldorf Astoria NY

Waldorf Astoria Grand Wailea Maui

And, sadly, I stayed here, but fuck em. It’s a terrible property, far from the strip and no casino. There are so many better options, like The Cosmopolitan, my favorite in Vegas.

Trump Vegas


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Let’s not call Goldman Sachs evil (yet, and for this potential infraction)


Goldman Sachs is the company everyone loves to hate. I’m among them. They perpetuated the financial crisis by creating financial instruments no one understood; they bet against their own customers; they benefited enormously from a government bailout; they will continue to push every line. Watch The Big Short for more on this.

Closer to home, they (along with other investment bankers) extract large amounts of money for little value add when it comes to IPOs. Money that should rightly go to the founders, employees or the company gets skimmed off and put into the hands of their preferred clients. VC extraordinaire Bill Gurley has written extensively on this.

The point of the last two paragraphs is to let you know that I’m by no means a shill for Goldman. I consider them the ExxonMobil, Monsanto, Koch Industries of the financial world.

BUT, we need to have some intellectual honesty here. We have one data point from one blogger and the Internet blew up. This was followed by another data point from Steve Wozniak. Then we have baseless speculation around it.

I have consulted for the largest players in credit cards and payments. I can’t tell you why it happened. (Yet.)

I can tell you what didn’t happen. Goldman doesn’t have an algorithm that says “IF male, SET credit to 4X female.”

If anyone at a large company made a decision based on a few data points, they’d be (rightly) fired.

Credit decisions are made by complex algorithms. Unless you’re applying for a mortgage, no one is looking at your application individually. (There are some edge cases, but not relevant to this discussion.) A bunch of data about you is crunched based on historical risk models. Out of that comes whether you are approved, what your credit line is and what your interest rate is. Then there’s the bank’s own risk profile.

We don’t know what algorithms are going to spit out. Because they’re based on historical models and trained with existing data, it’s likely that they will reflect gender and racial bias. Amazon designed an AI algorithm to make hiring less biased against females. It turned out it did the opposite, based on the assumptions that went into it.

These algorithms are regularly updated based on new assumptions. FICO 9, which is being rolled out, is much better than the widely used FICO 8. Banks and credit card customers get data from various credit agencies. (You actually have 3 credit scores!) Although FICO algorithms are widely used, credit card issuers and banks often use additional data from other sources.

For many years, Google thought that you needed a computer science degree from a top-tier university to be a successful product manager. Google analyzed the data and found that neither were useful signals and have theoretically abandoned them.

There’s a way we can predict algorithms: use test data and see how they respond. It doesn’t happen often enough, but I don’t know if Goldman did this.

Google Photos had a massive fail a few years ago, when it tagged some African Americans as gorillas. Clearly they didn’t do enough testing.

But I do know that the Internet loves a data-free pile on. Something that fits the narrative will drive clicks. This reinforces the common view people have of Goldman (the same view I have). The only potentially worse co-brand partner for Apple in this would have been Wells Fargo.

I’ve been on the other side of an Internet pile on. A company I worked for put out highly misleading information about me on Twitter. Because what they said fit a common and sensationalist narrative, it took off. No one waited to see what actually happened.

We don’t even know if there is a problem. It’s possible that the Goldman algorithm gives higher credit limits to women than to men. We don’t know. It’s possible that it gives roughly the same credit limits. We don’t know. It’s possible that it gives men higher credit limits than women, which is what is alleged. We don’t know.

Perhaps the biggest problem with the claims so far: American Express, Chase and Citi don’t even ask for gender on their applications. (I already have an Apple Card, so I can’t verify whether this is true for the Goldman card.)

So I’m going to wait until the facts are in to say whether Goldman is evil. For this one thing.




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5 things Andrew Yang must do for the next debate

As a lifetime product guy, I pay attention to substance, style and marketing. Yang has the first one nailed. He’s talking about two issues that will make or break the country and the world in the next decade: income inequality and climate change.

Yes, we need health care reform. That is a big problem for the country. But these two are more important.

So here’s a game plan:

  1. Name check other candidates.
  2. Pick a message.
  3. Tell a story.
  4. Practice what you preach.
  5. Think different.

Game the game – Name check other single digit candidates

The design of the debates is to give the top candidates the most airtime. The rich get richer. Moderators will always go the highest polling candidates; that’s the nature of media. They have a hard time thinking beyond two. In one of the earlier debates, CNN’s Don Lemon asked a question about income inequality – but didn’t direct it to Yang.

The rules of the debate are that if someone is mentioned, they get time to respond. Right now, what happens is that Biden, Bernie and Warren talk about each other, so they get more airtime.

Turn those your rules to your advantage. Yang, Booker and Harris should name check each other, thus getting more time.

YANG: Sen Harris represents California, a state where you have people with tens and hundreds of millions of dollars living a mile from people shooting up in the streets. What have you done on income inequality.

HARRIS: You’re a techie who made a lot of money. Your UBI is a bad idea.

Don’t talk about Biden, Bernie or Warren. This gives them more air time, which is what provides oxygen for enthusiasm and dollars.

Think of it as a game of debate keep away. That may sound cynical, but them’s the rules. You’re already playing it, you just don’t know it. Biden, Bernie or Warren are holding the ball.

Obviously, this would require working with your fellow candidates to pass the ball back and forth.

Pick a message and stick to it

There should be one key message. Warren and Bernie focus on Medicare for all. Biden focuses on the fact that he’s an old white guy who is friends with Obama.

You’ve got too many messages. Pick one: UBI. Legalizing pot is great and should be done. But it distracts. You could put that messaging out in other channels. Facebook probably has an ad targeting group of “potheads.” Use those tools for the sub message.

But keep it easy to remember. The last guy had one message: white power. brown people are bad and they’re responsible for everything that’s wrong in your life.

Your message is better: it’s the robots, not the immigrants. This would also be a way of getting at Trump’s core message.

Tell stories, not stats

As tech guys, we focus on numbers and stats. Booooooooring. Tell stories of real people, people you’ve met on the trail. Here’s a good one.


Here’s another:

They’re good stories because it’s a real person talking about what they’ve been though, but also what they’re thinking about. They also happen to be 100% true.

You could easily turn those into 30s or 60s. (Just don’t piss away ad dollars on TV — that’s a whole other conversation.) The story can shrink or expand to fit the time slot. Have a 6 minute block on CNBC and the anchor wants you to talk more, you can.

Practice what you preach, avoid the gimmicks

The one family thing last debate was a gimmick that fell flat, as I’d expect. It’s almost the kind of thing a huckster like Trump would do. (Except that he wouldn’t because he does give out money unless you’re a porn star.)

You could give your staff their own freedom dividend. Every full time staffer gets $1,000 a month. That will generate a lot more stories. When staffers are talking to media, they can then relate what they’ve done with their $1,000 dollars. Real people talking resonates; abstracts do not.

Think different

Too many people in politics hire experienced consultants who’ve been roaming the halls of DC forever. (Don’t know if this is the case with your campaign.) Like with the core issues of income inequality we talk about, technology can make politics more efficient and winning elections easier.

This is an email I sent to a high-profile VC in 2016 about an idea I had:

Screen Shot 2019-10-07 at 10.37.29 AM

Three months before the 2016 election, I suggested that Facebook could be used effectively to win the election. This would have been a perfectly legitimate way to do this. I couldn’t get anyone’s backing. But we all know what happened…

Politics isn’t really that different from designing products. You have to understand human psychology, address a distracted audience and get the right product in front of them.

So, think different. You’ve got a tech community that wants to see you win.



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My personal environmental footprint


It’s a trend in corporations (at least those outside the extraction industries) to do a self analysis on your environmental effects. I wanted to think deeply about mine.

I recently mailed a mercury thermometer to a friend where she has a safe disposal facility; I don’t and I didn’t want to throw it in the trash given all of the toxic effects of mercury.


  • Don’t eat much meat.
  • Use public transit primarily. Easy to do in Manhattan.
  • Walk a lot. Pretty much a requirement in Manhattan.
  • Live in a densely populated area.
  • Recycle a lot.
  • Try to use a reusable water bottle as much as possible.
  • Combine shopping trips (in rare cases I’m buying in store and have to drive).
  • Use Alexa to turn off lights and control temperatures in other rooms.
  • Limit printing. When possible, I use mobile boarding passes for flights or mobile tickets for events. When not possible, I print on the backside of something else.
  • Use a duplex printer.
  • Reuse backside of paper.
  • Don’t read newspapers in print. That’s a lot of paper that is 1) cut down from trees 2) heavily processed with chemicals 3) big rolls are transported cross country 4) completed product is printed and then transported across town 5) read (or unread) papers that are then transported for disposal.
  • Use Nespresso capsules.


  • Use the AC (mitigated by using Nest to reduce energy consumption).
  • Fly a lot. A lot of it is work related, but there are still plenty of personal trips.
  • Buy too many electronics. I’ve really cut back here for two reasons: there is so much electronics waste (much of it with heavy metals) and so much of what is made today is utter garbage.
  • Prefer triple ply.
  • Still get paper statements for everything. The banks and credit card companies all use different logins and have different processes and restrictions. It’s just a lot easier to go to the mailbox. If there were a way to get the statements sent to my Gmail and made it just as easy as going to my mailbox, I’d do it in a heartbeat. The security concerns that used to exist for this don’t exist anymore, but no one seems to be working on it.
  • Use a lot of napkins (Indian food is messy).
  • Drink too much canned soda.
  • Drink Mexican Coke. Real sugar in a glass bottle versus high-fructose corn syrup is SO much better.
  • Don’t unplug chargers, printers and other low power devices. These things consumer energy, but the amount is so tiny that it’s not worth it for me.

Of course not all of these things are equal. The heaviest consumers of energy are transportation, lighting and climate control. But the primary cause of climate change is cattle raised for beef.

What am I missing?

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FAANG + Microsoft market matrix

Here’s my quick take on the current state of the technology market and assessments of Amazon, Apple, Facebook, Google, Microsoft and Netflix.

What did I miss? What do you disagree on?



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Thoughts on this week’s suicides and how you can help

Help is just a call awaySuicide and mental health get the public’s attention when you have notable deaths like those this week. But there are thousands that go unnoticed every week.

One of the dirty little secrets of Silicon Valley is the high percentage of entrepreneurs who have mental health issues, which is 3-4x the U.S. average. Constantly hearing about people with exits in the tens or hundreds of millions of dollars doesn’t help; even people who are millionaires can feel like failures in the bubble that is Silicon Valley.

Here are some things that you can do if you feel someone you know* at risk.

  • CALL or SKYPE or do something other than posting a status message or email.
  • Don’t worry about whether you’re “close enough.” It doesn’t matter how close you are.
  • Don’t assume someone else is doing something. (Unless you are talking with them and coordinating.)
  • If you say you are going to be there, be there. This is NOT the time for hollow promises. 
  • If you aren’t local, find a mutual friend who is local and express your concern to them. If you don’t have a mutual friend, look through their friend list and find someone who is. If things look urgent, call the local police and ask for a “welfare check.”
  • Your friend might need professional help, including medication. Help them find it. Sometimes talking isn’t enough. If you don’t know where to turn, contact me.
  • Don’t publicly comment on the topic, especially with names or pictures. No blog posts, no tweets, etc. Google is forever. Unfortunately, most people aren’t enlightened on the topic and it can have negative consequences down the road.
  • Don’t go away after you think something has subsided. Keep in touch.

* I specifically did not say “if a friend is at risk.” If you know someone is at risk, you should take action.

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Autonomous vehicles are going to affect a lot of jobs

3692201862_ea517d2565_bAutonomous vehicles will change society in more fundamental ways than most imagine. Yes, there are the obvious ways that everyone talks about: driverless Ubers, automated trucks, cities without private vehicle ownership.

But there is a large ecosystem of occupations that benefit from bad driving.

  • Police officers. Most people probably won’t shed any tears over this. But there are a lot of cops whose role is traffic enforcement. With self-driving cars, they will be programmed to obey the rules.
  • Paramedics, flight nurses, ER doctors. Fewer car crashes mean fewer trips to the emergency room. I have a friend who is a flight nurse. Her job is to get in the helicopter to rescue people by the side of the road. There will be less need for that. In 2010-2011, there were 3.9 million annual visits to the emergency room because of car crashes. 43% of those arrived by ambulance.
  • ER doctors, radiologists, trauma surgeons. Of the people arriving in emergency rooms because of a car accident, 70% had imaging done, including X-rays (59%) and CT scans (30%).
  • Insurance agents, insurance underwriters order, claims examiners, personal injury lawyers. There is an entire ecosystem of people who benefit from the financial aftermath of car crashes. Car insurance in the U.S. is a $100 billion business. There’s a reason you see that gecko everywhere; car insurance companies are perennially among the largest advertisers. That’s just personal insurance. Commercial is billions more.
  • Tow-truck drivers, body shops, mechanics. Someone needs to clean up cars after the crash. Fewer crashes will mean fewer repairs. Body shops alone are a $40 billion business. 180,000 people work at body shops. The median salary is $40,000. That’s a nice lower-middle class job.
  • Parking enforcement officers (meter maid), parking meter collectors, driver license examiners. More of life’s little annoyances. Vehicles will nearly always be in motion; no worries about finding a meter to park at. No meters mean no parking enforcement needed. That also means no coins. (Other aspects of technology will chip away at the collections jobs. More on that later.) In NYC alone, parking tickets generated $565 million in fines. Camera violations were another $100 million.

These are just the second-order effects. There will be plenty more. There a lot of other industries like roadside motels, truck stops, restaurants and more that will feel third-order effects.

It will be one of the biggest changes to the transportation infrastructure since the Eisenhower interstate highway system was built beginning in the late 1950s.

Despite the challenges, autonomous vehicles provide a net societal good. We should minimize human suffering. We should be thrilled that air will be cleaner because fewer accidents mean fewer traffic jams.

But that’s cold comfort to those who lose their middle-class jobs.

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How technology chips away at jobs

Subway token booth

We may still call them token booths, but none of them have tokens anymore.

Many in the technology world are dismissive of notions that technology costs jobs; part of that may be because jobs don’t disappear overnight. We hear on the news about mass layoffs; we rarely hear about steady declines caused by adoption of new technologies.

Just look at the fare technology of the New York subway system.

New York had subway tokens since 1953. (Before that, the turnstiles used coins.) About 50 million tokens were in circulation. Tokens required a lot of manpower. People had to create the tokens; people had to sell the tokens; people collected the tokens; people put them back in to circulation. The last subway token was sold in 2003, at 50 years old.

In an obituary for the subway token, the New York Times wrote:

Handling all those tokens — emptying them from turnstiles, delivering bags of them to token booths, counting them out to riders — is cumbersome and expensive, and transit officials have long looked forward to the day when most of their business with riders would involve exchanges of electrons, not metal and paper.

The token’s demise (and that of many of its handlers) was the result of technology. The MetroCard was introduced in 1994. It allows subway riders to load money on to reusable plastic cards. You can go up to a machine, insert your money and get a card with $40 on it. Instead of carrying a bunch of tokens in your pocket, it’s something small you can put in your pocket. There’s nothing nostalgic about it (at least for now), but it is simple and efficient.

It still requires people to maintain the giant fare machines. People are needed to take out the cash and put in more blank MetroCards. But as credit card usage increases, the machines need to be emptied less often.

Even the MetroCard is already slowly being replaced (with a bigger shift coming). With my EasyPayXpress, my MetroCard renews itself whenever my balance runs low. I no longer need to stop by a machine. Less wear and tear on the machines.


The MetroCard that fills itself.

MetroCards themselves are an endangered species. Increasingly, magnetic stripe cards are becoming a rarity for transit systems around the world. The mag stripe is giving way to contactless payments. Most systems use a proprietary card; some, like Chicago’s, can use any credit card (or phone) that has NFC capabilities.

With contactless payments and mobile phones, the people who print and distribute the blank cards will be in danger.

None of these changes will happen overnight; it took 10 years to phase out the subway token. It’ll be at least 5 more before the MetroCard is phased out. (The MetroCard is expected to die at the age of 30; the token lasted until 50.)

Every step has increased the convenience for most riders. Less time waiting. Fewer things in your pocket.

But your convenience is someone else’s paycheck

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