Talking things out

In team catchups lately I’ve started to share an insight across multiple team members, one on one. It would be more efficient to put these thoughts in an email, or bring them up when everyone is together in a meeting. Yet I find that the process of talking things out, hearing different perspectives, & iterating serially - rather than seem repetitive - does wonders for clarity of thought.

One on ones can seem procedural. Some people view them as another meeting in the calendar - something to get through them as quickly as possible, or to freely cancel when something else comes up.

It may in fact be the most important time of the week - the best opportunity to craft and refine a company strategy.

The Evolving Story of Brands & Distributors in Travel

One of the key themes emerging over the past decade of travel startups has been the convergence of what it means to be an operator ‘brand’, and what it means to be a travel ‘distributor’. This convergence was articulated well by Ritesh Agarwal, founder of OYO Rooms, in this Skift interview from 2015 (excerpt here):

“Today the brands and distributors are fighting with each other, but in the next five or 10 years, companies are going to be created that are going to be Internet-first and also brands” 

A decade ago, when you booked a hotel on Expedia (classic distributor) and the stay went awry, as a consumer you probably wouldn’t have tried to call Expedia to make it right - you’d walk down to the front desk and plead your case.

The situation is totally different now. The rise of Airbnb & the hotelier of 1 has introduced an entirely different dynamic - the ‘branded distributor’. While it’s not how the legalese is structured (e.g. ‘hey, we’re just a ‘network’, we have no accountability in practice’), clearly the expectation is different. Consumers routinely call Airbnb when something goes wrong, and for the most part their issues are resolved by Airbnb acting as a principal if not possible with host directly.

But what does it mean to be a ‘brand’ when your 'operations’ devolves into a marketplace managed through guidelines and behavioral norms rather than traditional accountability systems?

Clearly as an Airbnb consumer, you are much more attuned to the fact that things can go wrong when you book an apartment rather than hotel stay - it’s now part of the generally accepted risk-reward tradeoff in the accommodation market. As long as these tradeoffs are well understood, extra choice has been great for the overall consumer.

Likewise, a similar trend is playing out in tours & activities. GetYourGuide, historically a tours & activities distributor, launched a new ‘Originals’ product line with the following promise:

World-class guided tours. We took exceptional guides and experiences and perfected them, based on feedback from our customers. More time to explore. Special access and entrances minimize time spent waiting in line. Zero stress. Exceptional guides.

Does this make GetYourGuide a brand or a distributor?

Is the tour development process and consumer promise from a distribution-first business like GetYourGuide really that different from a more traditional brand? More importantly, is the consumer experience, on average, that much different? (for a mass market consumer, I would argue no)

Can traditional brands afford to not build distributor-like distribution capabilities if they hope to scale? (I would also argue no)

Distribution matters, as the rise of Booking.com over the past decade demonstrates. Similarly with the quick traction of early days GetYourGuide.

But brands matter too. The cost of product development - with a smartphone in your pocket & possibility of an Internet shop front in minutes - is incredibly low. Costs this low means noise level are high - there’s never been more choice.

Which is precisely why brands - the ones that really stand for something that’s clearly expressed to the consumer - matter more than ever. Just don’t forget about your distribution.

More communication is never a bad thing

Earlier this week we set up a lunch & learn with our Philadelphia office. Usually lunch & learns are reserved for new learnings or presentations by functional leaders or contractors on a project. In this case the lunch & learn had no special topic - just a rehash of some of the themes at Context over the past few months, and an excuse to break bread together. It was casual and fun, some questions, and good practice for me to present some of our recent insights.

Today I did something similar with email. There was no special news or organizational announcement to share. I summarized a few conversations I’d had this past week about Context with some potential partners, and offered a window into a strategic opportunity I’ve been wrestling with in my head. Honestly I didn’t anyone would be too interested.

Several members of the team replied with warm emails - ‘this was awesome’, ‘it was great to hear what’s on your mind’, ‘thanks for sending’. It led to one new helpful introduction for a partnership opportunity, & another side discussion with a few other team members, We wouldn’t have connected these dots in this way, at this time, if I never sent the email around.

It was a useful reminder: more communication is never a bad thing.

Giving gifts generously

Halloween in NYC is visiting shops instead of houses. One of the shops we visited last night was a fancy new coffee place in Tribeca - nitro cold brew, etc. They gave out homemade Rice Krispie Treats in a lightweight branded paper bag with the name of the shop. Beautiful presentation.

Upon opening the bag, the treat inside was tiny - a fraction of the size of a normal Rice Krispie Treat. It was more like a sample.

I was reminded of one of Danny Meyer’s maxims in Setting The Table:

Some restaurants [during Restaurant Week], unfortunately, offer inexpensive fare and propose very limited menu options as a way to manage costs and do a bit better than break even on a three-course meal. We take the opposite approach. I am convinced that if you’re going to offer a gift, it’s important to give it graciously. We approach Restaurant Week by offering a generous number of choices for the appetizer, main course, and dessert, representing considerably more than $20 worth of food and quality. The point is to make people feel a sense of abundance and value.

What is lost today in the cost of generosity is a fraction of what stands to be gained through the act of that generosity. It’s a rounding-error marketing expense. Customers don’t miss obviously generous and gracious gestures. In fact, as the average major metro retail business is no doubt aware, opportunities for the kind of exposure and new customer acquisition like that of Halloween are rare - a few times a year at most. A few times a year to really bring in new customers who can tell their friends & come back repeatedly. Walking around the city yesterday, it was surprising how few shops appreciated this & did anything to stand out - basically none.

Take advantage of the rare opportunities for new customer touchpoints to put your absolute best foot forward.

Paul & the early spread of Christianity

Christianity is the most successful religion of all time, and arguably the most successful movement in human history. How did it spread so successfully - a legacy of over 2 billion followers and almost 1/3 of the world population today?

Paul: A Biography tells the story of Paul (formerly Saul of Tarsus), a man without whom Christianity would not have had the significance it now has. Paul’s story is a classic founder tale: a moment of insight, relentless evangelizing, & dedication to the mission.

Paul didn’t see Christianity as a different ‘religion’ - indeed, religion was a belief system far more infused into daily life in the ancient world than a separate set of activities. Paul saw Christian beliefs as the conclusion to loose ends at the end of Deuteronomy in the Old Testament. Deuteronomy speaks vaguely of a future restoration of Israel from Jewish exile initiated by the destruction of the first Temple in 586 BCE. Many Jews in the time of Jesus had returned to Israel, the Temple was rebuilt, but with Romans still ruling over the land many Jews were still waiting for more definitive deliverance.

The Book of Daniel (& others such as Isaiah) picked up on the promise in Deuteronomy, introducing the idea of restoration occuring in “seventy-sevens”, or 490 years. Many Jews believed this time was drawing near, which inspired a wave of zealous prophetic leaders (Reza Aslan’s book Zealot covers this topic thoroughly) to descend on Jerusalem and shake off the yoke of Roman rule for a new & restored Israel. Jesus was the most influential of those leaders.

Paul, who was brought up a Torah-fluent religious Pharisee, originally intended to chase down the original followers of Jesus and bring them to justice. Yet on the road to Damascus Jesus came to him in a vision, and he switched sides entirely to dedicate the rest of his life to spreading the news: the Messiah, descended from King David, in a story that began with Abraham, has reached its logical conclusion. The return of God would usher in an era of heaven and earth as one.

There were many ingredients that supported this message to succeed so wildly and change the course of history.

For certain Jews who studied the Torah, this was the conclusion they’ve been waiting for. Deuteronomy left the conclusion hanging, & there was plenty of evidence that the restoration hadn’t yet happened: Roman rule in the holy land, a large Jewish diaspora in Babylon and throughout the near east. Paul, a whip-smart, persuasive, and tireless orator, helped do the convincing. These Jews provided the early momentum to kickstart the movement.

The infrastructure laid by the Greeks & Romans paved the way for a quick spreading. Roman roads linked the far reaches of the eastern empire. Paul spoke Greek as did the broader area (Latin was the language of the elite Romans, Aramaic that of Jesus & the local Semitic population).

The legal infrastructure was conducive as well. The Jews had negotiated a carve-out with the Romans that allowed unique specialize privileges not to worship Caesar - provided that they prayed to their God for Rome & its emperor. Early Christian classification in Antioch as part of the Jewish religion allowed it to spread openly.

Paul was the perfect leader to spread the word. Outside of his personal qualities & tenacity, his deep knowledge of the Torah allowed him to weave together the narrative as few others could. His Roman citizenship allowed him to travel freely throughout the empire, and at least once saved him from persecution by Roman authorities (e.g. “I’m a Roman citizen - you can’t do this to me!”). And he was the most convincing salesperson, perhaps a skill learned from his family’s vocation as itinerant tent makers, comfortable with a wide variety of customers. As Paul says in Corinthians:

“I became like a Jew to the Jews, to win Jews. I became like someone under the law to the people who are under the law, even though I’m not myself under the law, so that I could win those under the law.”

As compared to Judaism at the time, Christianity was far more of a mass market proposition. The Jewish God was mysterious and vengeful - the flood, Abraham & Isaac. Not to mention a critical practical barrier for those drawn to the faith from the outside: you had to get circumsized. It was Paul who negotiated away this requirement to conversion with the inner circle Jesus’s followers in Jerusalem - his brother James & Peter. Without this concession, the proposition likely would not have worked.

As compared to Roman means of worship at the time, Christianity was far easier to follow (one God versus a lot of deities, as well as Caesar). Caesar and the emperors were also of a standard not easy for the masses to relate to - urban, Latin-speaking warrior-heroes. It was easier to relate to a simple man from a small town preaching messages of love and acceptance.

This for me was the major takeaway from Paul. Humans most fundamentally want to me loved, and a religious framework that operates on this basis is more appealing that more complicated ritualistic systems. Christianity was a killer proposition that also benefitted from the right place, right time & right leader following the death of Jesus.

Jewish-rooted ethics & a more scalable approach changed the world and certainly for the better. Christian values in the early centuries AD as initiated by Paul created a tremendous amount of good: more universal healthcare, education, & treatment of women (pagans at the time routinely practiced infanticide for unwanted children - especially girls). Paul’s legacy is largely what is referred to as Judeo-Christian values today - he is one of the great leaders and (co) founders of our history.

The Problem With "We've Tried This Before"

Startups move quickly. Lots of things are tried and tested. Often conclusions are drawn quickly based on the information available at the time. 

Sometimes at startups a new guy enters the room and wants to try stuff that’s already been tried before. As a co-founder of onefinestay, this could drive me crazy. “We’ve tried this before - it doesn’t work” I used to think, & often say. Sometimes I was right, & sometimes we tried again - & had a different result. 

This issue is particularly hard to reconcile. Often “we’ve tried this before” is wrapped up in ego - “if I tried it & it didn’t work, its not like this person will figure it out”. There’s also the desire to always be learning, to not waste time, not make the same mistake twice. 

Yet conditions are always changing. The people around the table are changing, and are always assimilating new information. Organizational priorities change. The market conditions change. Internal capabilities improve. Technology improves. 

We need to recognize that things are always changing. The previous lessons learned can’t be strictly applied to the present time - doing so is a version of fixed mindset. 

So I try to always stay aware of the faulty logic that can be behind “we’ve tried this before”. 

Resisting the itch

One of the features of meditation practice is when I experience discomfort - pain in my knees or back, an itch on my ear or nose - I resist the temptation to move. We’re conditioned to immediately address any discomfort - itch on your ear? Scratch it! Rather than do this, meditation teaches us to first observe what’s happening when we’re uncomfortable - explore what discomfort is - before responding with action. 

The same is often true in organizational contexts. Lots of things happen that feel uncomfortable - growth is slow this month, a particular initiative is taking a while to get off the ground. There’s a natural temptation to react quickly to make ourselves feel better - slash prices! Make the hire - we need to fill that role! Pull the plug on that new product - what were we thinking!? 

In my experience, it's worth staying with organizational discomfort for a little while longer than what feels comfortable. We can observe root causes & real opportunities more clearly, & give appropriate time to let strategic decisions take hold. This can go against the grain of the human tendency to take quick action, but can often lead to improved outcomes.  

Top 5 Books / 2017

1. The 100-Year Life: Living & Working in an Age of Longevity - our kids have a 50% chance of living to 105 at the same time that many historical sources of financial and emotional stability are vanishing - what are the implications for happiness, employment & society?
2. The Agony & the Ecstasy - beautiful historical biography of Michelangelo. He was a true creator, pursuing his passion of sculpting marbles despite innumerable obstacles & irrational incentives.
3. Principles: Life & Work - a phenomenal meditation on self-care and org leadership, & a guidebook for building lasting companies.
4. Homo Deus: A Brief History of Tomorrow - a darker companion piece to the also great Sapiens & 100-Year Life. How will many of us find meaning when routinized work is automated in the next 30 years?
5. One Hundred Years of Solitude - in the 'post internet' world, where any question or image can be answered or discovered in seconds, creating a sense of true wonder can be hard. But as parents, & leaders, this is what we should be shooting for.

Leading from the middle

At a breakfast yesterday hosted by Bleeker, we had an in-depth discussion about leadership, & how to lead others. 

Leadership is a word that means different things to different people. We went around the room and no two people had the same definition of leadership. 

At one point the discussion evolved into style metaphors - e.g. servant leadership, leading from the front, leading from the back. Someone said they prefer to 'lead from the middle'. It's the first time I've heard this metaphor, and it really resonated.

The essence of leadership isn't about, on one hand, making a lot of decisions that cascade down through the organization, top down. Nor is it only supporting the team 'from behind' & getting the most out of every individual. It's both of those things. Leadership emerges out of knowing when to lead from the front, and when to lead from the back. When to employ wartime tactics, and when there's enough relative peace to focus on process. Achieving the right balance at the right time - staying fully present to the exact time and place the organization finds itself in - is leadership. In order to recognize this, you need to be in the middle. 

The same is true for team management. A common scenario that founders or senior team members find themselves in: person x just joined the organization and needs a lot of support. How much guidance should I provide? Should I be directive or much more hands off? 

The answer of course is it depends. Specifically it depends on the unique qualities of the two individuals - the manager and the managed. And the core values of the organization, as well as the specific time and place within its evolution. There are no template answers. In light of this, knowing the right way to proceed is leading from the middle. 

This is the danger of personality assessment frameworks (Myers-Briggs, etc.). These frameworks tend to assume a static environment and static personalities. In my experience the real world is much more complex. As soon as a unique individual is reduced to a box of 16 (or whatever), there's too much temptation to oversimplify how its best to interact with that individual. There are about 7.5 billion boxes in the world today. The best a leader can do is stay fully present to the needs of the individual and organization at that time. As soon as decisions are made based non-context specific rules or frameworks, problems emerge. 

This means that our organizations exist in a state of unending change & complexity. Leading from the middle is the ability to keep in balance the needs of the organization at that specific time - which is always evolving - and the needs of the specific individuals within the organization - who, like the company, are also always evolving. 

September 11

On September 11th, 2001, I had just moved into an apartment on the Upper East Side with three friends from college. That afternoon we were heading to Long Island to collect a couch from my aunt to help fill our empty living room.

I woke up a little late that morning. The first tower had already been struck & my roommates were watching the scene unfold live on TV.  Grief and fear would come later - that morning I only remember disorientation. "I guess I should call my aunt and tell her we're not coming", I remarked. It was hard to comprehend what was happening. As the towers fell, the scale of the tragedy suddenly became clear. 

On the evening of September 11th, we watched George W Bush speak from a packed restaurant - everyone was on the street:

"The search is underway for those who are behind these evil acts. I've directed the full resources for our intelligence and law enforcement communities to find those responsible and bring them to justice. We will make no distinction between the terrorists who committed these acts and those who harbor them."

We cheered. In those days immediately following 9/11, his approval rating shot up to 90%. We didn't process the long-term implications. We were bewildered, scared and angry. 

9/11 was an overnight loss of innocence for an entire generation. Moving into the city was a common goal for post-college kids from the suburbs, like me. Suddenly the city was the epicenter of red and amber alerts, missing person notices on every phone booth, vigils in front of firehouses. These were the days before Facebook - there were rumors for weeks about so-and-so who died in the 9/11 attacks - a friend from camp, a childhood neighbor. Sometimes it was true. The loss was and still is profound and unfathomable. 

I now live downtown. It's a strong and vibrant community - as strong as ever. It's easy to forget when watching my kids run around Washington Market Park, or dropping my daughter off in the school yard, that an unimaginable tragedy occurred at our doorstep 16 years ago. The Freedom Tower is visible from almost every vantage point in Tribeca. 

It's my hope for next generation that even though the innocence is gone, it can be upgraded to something more real. A greater appreciation of life, each other and the broader world around us.