Here’s what the Airbnb ads could have looked like

Read this post on Medium.

Left, photo credit: Martha Kenney / Facebook via AdWeek, Right, fabricated ad: Winnie J. Kao

Disrupting a static industry is hard. It’s even harder when the city you’re headquartered in hates you.

People are angry with Airbnb for recent billboards and bus shelter ads in San Francisco. The ads were a cheeky way to allude to Proposition F, which is up for voting in the next few weeks. The messages refer to the estimated $12 million in hotel taxes that Airbnb paid to the city in the last year.

But the campaign came across as passive aggressive and smug. Social media erupted, and Airbnb is taking the posters down.

This isn’t simply a local issue.

The public’s opinion of big tech companies has a tangible impact on how much leeway startups have to operate. Especially when legislation is involved.

Here’s why the ads failed, and what Airbnb should have done instead.

1. Flaunting money is a bad idea.

An Airbnb spokesperson said: “The intent was to show the hotel tax contribution from our hosts and guests, which is roughly $1 million per month. It was the wrong tone and we apologize to anyone who was offended.”

What is a hotel tax contribution? The average person is not going to research this topic.

They will, however, take the billboards at face value. Whining about $12 million dollars in taxes leaves a bad taste in everyone’s mouth.

As one user on Twitter said, “$12 million is nothing for a $25 billion company.”

2. People already think tech startups are arrogant and elitist.

This issue has been heavily reported on in recent news, and confirmation bias kicked in.

All of the following mental associations pop up: tech startups taking over the city, Dropbox tech bros kicking teenagers off a soccer field, a changing city landscape, gentrification, evictions, tech bubble.

These ads intensify the “us versus them” rift.

If you want to defend Airbnb, you are now forced to choose: are you a rich tech kid in a Google bus, or part of the diverse fabric of San Francisco?

3. Don’t joke about topics where you are considered part of the problem.

When running ads, every tech executive, startup founder, and head of marketing should ask themselves these questions:

“Are we trying to be funny? Are people going to take this the wrong way? Are we amplifying a sore subject? Are we giving our opponents ammunition against us?”

Other brands have gotten into trouble when they approached touchy subjects: Lululemon about their CEO getting fired, and McDonald’s about it taking 796 years for an employee to make a million dollars on minimum wage.

Humor is tricky. When in doubt, stick to poking fun at yourself.

What could Airbnb have done differently?

Airbnb could have started with a gracious attitude.

They could have emphasized being part of the city, rather than separate from it. They could have mentioned how lucky they are to contribute tocommunities within San Francisco, instead of whining about taxes.

I’m not one for critiquing without offering a few suggestions. In the spirit of this, I’ve re-created what the ads could look like if they built goodwill.

Left, photo credit: Eric Eberhardt / Instagram via SF Weekly, Right, fabricated ad: Winnie J. Kao

Before: “Dear Parking Enforcement, please use the $12 million in hotel taxes to feed all expired parking meters.”

After: “Dear San Francisco, we’re proud to host friends from around the world. And we’re thankful to call this home.”

Left, photo credit: Martha Kenney / Facebook via AdWeek, Right, fabricated ad: Winnie J. Kao

Before: “Dear Public Library System, we hope you use some of the $12 million in hotel taxes to keep the library open later.”

After: “Dear Public Library System, Thanks for creating a space for learning. We’re honored to do our small part to support this big city.”

Left, photo credit: Kevin Antonio Sorlano / Facebook via SF Weekly, Right, fabricated ad: Winnie J. Kao

Before: “Dear Public Works, please use some of the $12 million in hotel taxes to install more electric vehicle charging stations.”

After: “Dear Public Works, Our friends light up when they visit. Thank you for keeping San Francisco beautiful, for all of us.”

Is it difficult, or just dramatic?

“I quit.”

Those words are dramatic.

I used to think that quitting your job was the craziest, bravest thing you could do. Then I did it twice, without anything lined up after, and realized that it’s not that crazy or hard.

More importantly, over the years, I realized that walking away isn’t always the bravest option.

Our culture certainly glorifies the idea of a dramatic exit. We can confuse the act of getting up and walking out as being the hardest part.

But what if the difficult part is speaking up while there’s still a chance to fix things?

Something or someone is bothering you, and it keeps festering, festering, festering. Until you just can’t take it anymore.

Maybe a coworker was disrespectful for the eleventh time.

Maybe your boss, yet again, dismissed your hard work.

Maybe your mother used that tone of voice that triggers you, and has for years.

In the moment, it’s easy not to speak up for a few reasons:

(a) Confronting the person means conflict. Conflict is uncomfortable. It’s easier to convince yourself that it’s really not that bad, and there’s no reason to exaggerate.

(b) Suffering in silence feels like you have the moral high ground. You’re being the bigger person by letting it go. You’re absorbing it all.

(c) If things really get bad, you daydream about how gleeful it will be when you walk out. You’ll have the last word, and oh boy, they’ll be sorry when it’s too late.

It’s easy to imagine a triumphant, declarative, dramatic exit.

When you’ve experienced death by a million cuts, the decision is easy: you let go because you no longer care. At that point, there is so much evidence that the person has obviously wronged you… How could you do anything else but walk away?

But there’s another option, and sometimes, it’s the harder choice:

You can choose to speak up when there is still time to change the dynamic. When you still have the psychological bandwidth to want to change things.

While you still care.

Now there’s a new dilemma.

You now have the responsibility to deal with the anxiety of having to figure out how to have this conversation. How to talk to your coworker, how to approach your boss, how to bring up a tricky topic with your friend.

That’s not easy. There’s no guarantee that it’ll work.

But something happens when you commit to trying to figure it out, bit by bit. When you decide that it’s worth speaking up and learning how to express what you want to say.

You begin to create an environment for dialogue and honesty that deepens bonds between people.

Regardless of what the outcome is, when you do the hard work of getting through to another human being, you grow.

Why incremental polish is a waste of time

You’ve made up your mind 90%. But sometimes, right at the end, the remaining 10% veers uncontrollably into a black hole of overthinking.

“I just want to tweak it to make it a little better. It’s almost ready. I just need a bit more information. Once I have that, I’ll know for sure.”

I’ve come to the conclusion that spending a lot of time adding incremental polish is not helpful.

Why do we feel the urge to do it in the first place?

It seems to happen especially for decisions that seem high-stakes.

You want to do it right.

You want to give yourself the best shot possible.

You want to avoid re-work.

This one is big for me: You want to really understand the situation to prevent avoidable, expensive mistakes down the road.

All of those are legitimate concerns.

It seems like more time and more thinking is the solution to arrive at CERTAINTY.

This idea of incremental polish doesn’t just apply to applications, it applies to anything you ship.

An important email.

Picking which vendor to use.

Preparing for a meeting that might be uncomfortable.

Deciding on a strategy.

Even writing a tweet.

There’s a pull toward incremental polish, the nagging whisper that keeps saying: “I just need a bit more time to work on this.”

Whenever I catch myself thinking this way, I have to stop.

Will that extra information help you decide? Or will it just help your ego feel better because you subjected yourself to internal agony? If that internal agony didn’t actually get you closer to a smart decision, perhaps you could skip that part altogether.

It requires admitting two things to yourself:

1. No one is certain of the outcome. It might work and it might not.

2. You alone are responsible for making the decision.

As Seth says, “You don’t need more time, you just need to decide.”

PS altMBA applications close tomorrow at lunch time in NY.

For marketers and non-technical people: basic explanation of Twitter authentication


A couple weeks ago, I wrote a blog post about how Medium’s Twitter authentication process could be a bit confusing for users.

Medium kindly responded to my tweet, and pointed me to their FAQ. Their FAQ indeed says that Medium doesn’t post to Twitter on the user’s behalf. It didn’t explain the “why” behind it, besides linking to the Twitter developer site, which was confusing for a non-engineer.


I ended up asking a few friends, and wanted to share what I learned. If you know of other simple explanations, let me know and I’ll link to your post from here.

My friend Chris Poyzer, a senior software engineer at Hinge, explained it here:

“What you’re investigating is an OAuth (open standard for authorization) authentication process. It’s doing two things for the application.
First, it shows the application to verify the user through the third party service. In this case, it is Twitter.
Second, it opens up access to services allowing the app to act on behalf of the user on the third party.
The process is designed in a way that all this is possible without the app knowing the user’s password on the third party service.
For example, Hinge uses a similar process to register users through Facebook, but the app never knows the user’s Facebook credentials.
So when you sign in on the third party, you also need to authorize the app that you want to use on your account.
And at the same time, the app needs to ask for any and all permissions that it needs in order to work.
First, if the app is to tweet at anytime for any reason (with your permission or not), it must have access to post tweets on your screen.
So the app is asking Twitter if it can tweet for the user, and that is the permission that you are being presented with.
But there’s a second part.
Once the app has that permission from Twitter, what does it do with it?
In Medium’s case, they are telling you that they will not abuse this permission — that they will only tweet when you tell it to.
It’s a social contract of trust between you, Medium, and Twitter.
Now, some apps never actually post on the user’s behalf, but still ask for the permission.

This might be because of a couple of reasons. One might be because they are planning future features that require the permission, so they’re asking for it now because requesting new permissions will de-authorize the user requiring them to login again; or, more likely, it’s sloppy programming.”

Can people change? My thoughts on the altMBA

Can people change? This seems like such a debated age-old question, it might not even be worth asking. But I think it’s important to consider.

Today is the last day of the altMBA September session, and two days ago, we opened applications for our January 2016 session (Seth’s blog post here).

I’ll admit, I wasn’t sure what to write about in this post.

This is ironic, because we have our students publish their work 3x per week, and because I think about altMBA 24/7. So you would think I could easily find something to write about here.

But much of my writing is behind the scenes. Feverishly drawing out assertions, drafting strategies, writing drip emails, creating training guides, posting in Slack.

And more importantly, nothing felt like it could capture the magic of what it was like sprinting with this current class, and the inaugural class before it.

The momentum, the fast pace, the feeling of inspiration. Meeting cohorts of amazing people who pass the “Would I want to be stuck at an airport with this person?” test.

People you want to get to know more. People you’ll be in touch with for a long time to come. Weekly coach calls with all 7 coaches where it felt as if we were all physically in the same room on Fridays at 11am, even though we were in 3 different time zones on 2 continents.

The truth is, I care very much about the altMBA.

I’m sure our students know this, and the coaches know this… but sometimes it’s hard to say out loud.

Because when you say out loud that you care, and that you believe change is possible, you’re a little more on the hook.

When I was deciding what to write here, I wanted to go back to the idea of change. Whether people change. Whether organizations change. Whether cultures change.

My answer is yes.

Change can be slow, it can be unpredictable, it can feel futile. But it is possible.

People change every day.

They change their minds about trivial things. I thought I wanted chicken, but I’m going to order beef.

They change their minds about more important things, like their worldview. I realized that I’m the kind of person who does things like this.

They change what they consider they might do. I told myself I’d never do that, but now I’m open to it.

They change their behavior. I wasn’t a runner, and now I am one.

They change what they notice. I didn’t see it that way, but now I understand what you mean.

Change can be frustrating. Even if the end goal is much-needed, sometimes you think, “Is it worth it? Is it better to just not try?”

The world can break your heart when you try. At what point is it easier to say, “The status quo isn’t so bad. I wouldn’t have made a dent anyway. It would have been a waste of time.”

A waste of time. What does that mean? I believe that you should only do things if you’ll enjoy the journey as much as the destination. If you get to work with smart and kind people along the way. If there’s joy in knowing that you attempted.

But mainly, it’s not a waste of time if you believe that someone needs to be stepping up to make this change. When you decide to stop trying, it’s a sad day. It’s a day when one good person stops fighting the good fight.

If you don’t try, then who will?

The Venn Diagram of people who are (a) smart, (b) capable, and (c) who give a shit is really small. If you fit in this category, maybe you have a responsibility to try.

But it comes back to people. If you can change yourself, one other person, two people, four, eight, sixteen…if you can change a group, you can change a community, you can change an organization, you can change a slice of culture.

It’ll be hard until the day it happens, and then everyone will say, “Well of course it was going to happen.” It will seem inevitable, but only because you helped it to become so.

I just realized that I believe more deeply in change being possible, because I saw it happen…to myself.

I’m a different person from who I was when we were thrashing on the nebulous idea that would eventually become altMBA, when we launched, when we ran the first session, when we were running the second session.

I noticed it, and my peers noticed it. I’ve changed.

I was talking to an altMBA alum recently, and she said, “It’s like realizing that there’s another color that you didn’t know about. And you think, ‘What? This has been here the whole time? And I’m just now seeing this?'” We had one of those “RIGHT? ME TOO” moments where you feel understood and can barely contain yourself, because someone finally gets you.

I think people say that things don’t change, because it lets you off the hook. There are an infinite number of tactics about how to create change, but none of those matter if you don’t believe deep in your core that change is possible.

If you think you can do it better, you might be able to. So decide if you want to be that person. If someone will end up changing people’s minds, it might as well be you.

The world changes when people change. If you’re up for it, so am I. Want to leap together?

PS If it might be the right time for you, we just launched two new sites to share more about the altMBA. Let me know what you think if you check them out, and