Lisbon, Portugal

My first thought when flying into Lisbon, Portugal was, “Where am I?” It looks just like San Francisco.


Turns out the 25 de Abril Bridge was built by the American Bridge Company. The same company that built the Bay Bridge and it is painted the same color as the Golden Gate Bridge - International Orange.

After my initial disorientation, landing and making my way to Lisbon was super easy. Made easier, I hate to say, by Uber. Yep - Uber is available in Lisbon and inexpensive. As a result, I didn’t have to even change money or speak Portuguese, for that matter.

I landed first thing in the morning and made my way to my hotel, the dreamy Memmo Alfama Hotel. This was my view. I should add - I had perfect weather on my trip. :)


I arrived so early that I wasn’t able to check in but the people at the hotel couldn’t have been lovelier. They gave me a space to clean up and stored my luggage. I then headed out on a walking tour I had booked. It turned out to be the perfect way to get acclimated and fight off jet lag!

One of our first stops was a tribute to the great Fado singer, la diva du Fado, Amalia Rodrigues.


We winded our way throughout the many small corridors of the Alfama district until the afternoon. My guide, Emanuele, was wonderful and made me feel so welcome.


After a quick stop at the hotel I then decided to head out on foot to Belém, Lisbon, about a 2 hour walk. The people at the hotel thought I was crazy, but I knew I needed to keep moving to stave off sleep. Plus, if you know me, you know I was driven by something else:


I admit it’s a tourist destination, but after some very scientific sampling of pastries throughout Lisbon (see also Manteigaria (Chiado or Time Out Market) and Pastelaria Batalha (also in Chiado), I can say that Belém really did have the best Pastel de Nata (basically an egg custard tart).

Oh - Belém also has a palace with a changing of the guard you can check out, too.

In fact, Lisbon had a plethora of great food options. I also recommend the Time Out Market (super crowded but like the San Francisco Ferry Building - lots of gourmet food stalls), Mar Ao Camo (seafood just off a delightful square), Ponto Final, and Cervejaria Ramira (where I had the best lobster of my life - see below) (thank you dear Lobster). Note: if you really want to go to the source, go to Farol - it’s where the fishermen go and it’s just a ferry ride to Cacilhas.


After a full day of walking and eating I returned to my hotel and passed out. My plan was to get up early the next day and check out Sintra, a town just outside of Lisbon with lush gardens and several palaces.

I did manage to get up early but missed the first train out. So naturally I called an Uber!

I had a fantastic driver who took me straight up to the Palácio Nacional da Pena. I recommend starting there as it’s the highest part of Sintra and then you can easily walk down to the other palaces and the old town.

Also, pro tip: you only need to pay to access the park (about 7 Euros) and not the palace. The palace ticket is for an inside tour which I heard from others was not worth it. FYI.


And if you go first thing in the morning, you’ll be rewarded with beautiful, unobstructed views.


After scouring the Palace and gardens, I walked out and turned left towards the Castle of the Moors. You can check out that Castle or just keep walking on the trail that winds alongside it down to Old Town. It’s an easy walk that only requires tennis shoes/sneakers.

Old Town has a nice big square with views for days.


And of course, lots of nearby food options. Sintra has its own pastry, called Queijadas. They’re tarts made with cheese or milk.


I spent the day in Sintra and then headed back to Lisbon for an evening walk through town and then headed to a Fado show. These are typically very touristy and can require cover charges that include dinner. Fado’s roots are in Alfama, but if you just want to hear up and coming singers and have a drink, I recommend heading out to ___.

Other places people recommend: Tasca do Chico (only certain nights), A Baiuca, and Viste Allegre. 


Sigh. I miss Lisbon and Portugal already. There’s more to tell. Claramente! But this is where I’ll leave you, because I left Lisbon for a bit to visit Marrakech!

Late People

If you've ever taken a class with me, you know I insist on being on time. To me it's a sign of respect. A sign that you're taking the experience seriously. And, frankly, I'm communicating that I take this experience seriously.

Invariably, though, when I'm giving my little speech promoting on-time class starts, a few people arrive late. 

I'm instantly reminded of comedien Mike Birbiglia.

What late people don’t understand about us on-time people is that we hate you. And the reason why we hate you is that it’s so easy to be on time — you just have to be early. And early lasts for hours. And on time lasts a second. And then you’re late forever.

— Mike Birbiglia, Thank God for Jokes

At Bat

Remember when you learned to play baseball? I do. At the beginning baseball was my only option. There were no girl teams until I was older. No matter. The revelation to me was learning how to hit the ball – to connect.

The first time I did it by accident. It was an eye-widening, giddy moment. The coached yelled at me as I rounded the bases – “Remember!” he yelled, “remember that feeling!”

At my next at bat I tried to find it again. The vibration in my arms, the open sky feeling in my chest. My body looked for that feeling – the passageway to connection.

Of course, I had to swing and swing to find it again.

That’s what I’m looking for now. That feeling when you connect. There’s almost a perfect stillness before it happens. A quiet that portends success. And then after hours in the batting cages and several at bats, without any thought, your body just knows what to do.

You swing and you make contact with a force that wants to pull you off your feet. You follow through and let the bat fall from your hands as the perfect clang of an aluminum bat (hey this was little league) hangs in the air and the ball rises so high and travels so fast you think you imagined it.

Then you celebrate – your body free, you run, you dance around the bases.

I remember that feeling. Which means I can find it again.

I am in the batter’s box, waiting for the pitch.

Advice for Founders

I recently hosted a Founder Friday for Women 2.0. You missed it? Well, you missed out! On meeting fabulous entrepreneurs and entrepreneurs-to-be.

I was honored to be able to speak about my journey and offer a few bits of advice. Here’s what I shared:

When I reflected on what I could offer from the lessons I’ve learned from working in venture capital, founding and running a company on my own and selling it, I came up with three items to consider.

1. The word entrepreneurship comes from the French and means “to undertake.” Which I think is a lovely definition. It’s also a term not necessarily owned by Silicon Valley’s interpretation. Still it gets thrown around a lot and I don’t think enough people stop to ponder it. If language makes up our thoughts and thoughts create our experience, then I believe it’s a word worth questioning. It’s important then to step back and ask yourself why. Why are you pursuing “entrepreneurship”?

Is it because you want to play the game? This game is incubators, accelerators, generators, VCS, funding, hackathons, hacking houses, etc. This is a game and that means it’s not always fair; it’s stacked – there is an in group, etc.

Is it because you want to build a business? This is about the money making opportunity. It’s about hustle and not necessarily the next great technology. Building a business is not about getting venture financing; it’s about finding customers and making money.

Or is it because you want permission to do something else? Something other than what you’re doing right now, even if you don’t know what that is?

Ask yourself why and then own the answer. Embrace it. Play the game or focus on the P&L or do a lot of experimentation. One is not better or worse than the other. But if you’re honest with yourself about what you’re in it for, you’ll make better decisions for yourself and won’t find yourself stuck or down a path that ultimately is not where you wanted to go

2. Sara Blakely, the founder of Spanx, and one of the very few self-made female billionaires in the world has some great advice – don’t let your good ideas get killed too soon. She cautions sharing them. I agree, but don’t get too black and white about this. You have to be selective about how and with whom you share your ideas.

One thing I’ve noticed is that the whole “lean” methodology that is touted so much in the Valley right now is being taken too far. People feel pressure to put their babies out there and then see how consumers interact, etc. I think this is great if you’re testing an incremental idea, but when you’re testing a truly innovative idea, you can get your vision squashed harshly and needlessly.

I also see this with teams scrambling to put up profiles on Angel List before they’ve even launched products. They think go fast, get it out there, minimally viable product! But they forget that investors, regardless of what they may say, are fundamentally about financing. They want to see a return on their money. Which often means they’re pretty linear thinkers. They are less forgiving. You really only have one good chance to make an impression on them. I know there are a lot of articles written on the pivot, but when people are choosing whom to back, they’re looking for confidence and togetherness. It’s okay to not be ready. Don’t go out too soon.

3. Finally, you’ll be the most successful when you are true to yourself. You’ve heard that all before. But what does that mean? It means you stop yourself when you use the word “should”.  When you tell yourself “I should do this” or “I should do that” you aren’t in touch with what is authentically you. So how do you be true to you?

First, you need to invest in self-awareness. Self-awareness is the the ability to identify, express and manage your emotions. You do this by paying attention to your body. Often your body will be communicating something you haven’t let your conscience know about.

When you talk about a particular subject do your shoulders scrunch up around your ears? These are physical signs pointing you to how you’re really experiencing something.

Next, get in touch with your feelings. Not sure how you feel? Start by regularly asking yourself – how do I feel? 

Even if you can’t answer the question clearly, the very act of asking is an act of mindfulness. Asking will start to bring emotions to the forefront of your consciousness where it will be easier to identify them and then deal with them.

Then, check your thoughts. Once you’ve identified a thought, it’s important to question it. Is it true? Is it helping? Doing this will help you to detach yourself a bit from your thoughts and recognize that thoughts come and go.

There you have it. Some advice. Take it or leave it, but no matter what you do, I hope you enjoy the journey.

When Books Find You

I’m not a terribly superstitious person, but for some reason I believe that books find me exactly when I need them. What I’m reading always seems to mirror what I’m going through. It’s as if my inner knowing guides me to titles that will help to illuminate the way.

Most recently, this happened when I picked up a book I’ve had on my shelf for a long time but never bothered to read. Henry James’ The Jolly Corner.

It starts out like a ghost story, but turns into an epic battle between a man and the man he might have been. An excerpt:

He found all things come back to the question of what he personally might have been, how he might have led his life and ‘turned out,’ if he had not at the outset, given it up.

“It comes over me that I had then a strange alter ego deep down somewhere within me, as the full-blown flower is in the small tight bud, and that I just took the course, I just transferred him to the climate, that blighted him for once and for ever.”

“And you wonder about the flower,” Miss Staverton said. “So do I, if you want to know; and so I’ve been wondering these several weeks. I believe in the flower,” she continued, “I feel it would have been quite splendid, quite huge and monstrous.”

“Monstrous above all!” her visitor echoed, “and I imagine, by the same stroke, quite hideous and offensive.”

“You don’t believe that,” she returned; “if you did you wouldn’t wonder. You’d know, and that would be enough for you. What you feel – and what I feel for you – is that you’d have had power.”


I’ve been thinking about all the ways I learned to keep myself safe and how in the end, they didn’t keep me safe at all.  In fact, my behavior has posed the biggest risk to me that I’ve actually known.

In my search for answers, I uncovered an old essay by Malcolm Gladwell entitled, Big and Bad, that drives home my discovery [emphasis below is mine].

Ostensibly it’s about S.U.V.s, but like all good writing it’s about so much more.

Some excerpts:

“But that’s the puzzle of what has happened to the automobile world: feeling safe has become more important than actually being safe…

‘The metric that people use is size,’ says Stephen Popiel, a vice-president of Millward Brown Goldfarb, in Toronto, one of the leading automotive market-research firms.   ‘The bigger something is, the safer it is.   In the consumer’s mind, the basic equation is, If I were to take this vehicle and drive it into this brick wall, the more metal there is in front of me the better off I’ll be.’

This is a new idea, and one largely confined to North America.   In Europe and Japan, people think of a safe car as a nimble car.   That’s why they build cars like the Jetta and the Camry, which are designed to carry out the driver’s wishes as directly and efficiently as possible.   In the Jetta, the engine is clearly audible.   The steering is light and precise.   The brakes are crisp.   The wheelbase is short enough that the car picks up the undulations of the road.   The car is so small and close to the ground, and so dwarfed by other cars on the road, that an intelligent driver is constantly reminded of the necessity of driving safely and defensively.   An S.U.V. embodies the opposite logic.   The driver is seated as high and far from the road as possible.   The vehicle is designed to overcome its environment, not to respond to it…” 

Jettas are safe because they make their drivers feel unsafe.   S.U.V.s are unsafe because they make their drivers feel safe.   That feeling of safety isn’t the solution; it’s the problem…”

‘There are unexpected events that at any moment in time can come out and impact them—an oil patch up ahead, an eighteen-wheeler turning over, something falling down.  People feel that the elements of the world out of their control are the ones that are going to cause them distress.

Of course, those things really aren’t outside a driver’s control: an alert driver, in the right kind of vehicle, can navigate the oil patch, avoid the truck, and swerve around the thing that’s falling down… The trouble with the S.U.V. ascendancy is that it excludes the really critical component of safety: the driver

In psychology, there is a concept called learned helplessness, which arose from a series of animal experiments in the nineteen-sixties at the University of Pennsylvania.   Dogs were restrained by a harness, so that they couldn’t move, and then repeatedly subjected to a series of electrical shocks.   Then the same dogs were shocked again, only this time they could easily escape by jumping over a low hurdle.   But most of them didn’t; they just huddled in the corner, no longer believing that there was anything they could do to influence their own fate.   Learned helplessness is now thought to play a role in such phenomena as depression and the failure of battered women to leave their husbands, but one could easily apply it more widely.   We live in an age, after all, that is strangely fixated on the idea of helplessness: we’re fascinated by hurricanes and terrorist acts and epidemics like sars—situations in which we feel powerless to affect our own destiny.   In fact, the risks posed to life and limb by forces outside our control are dwarfed by the factors we can control.   Our fixation with helplessness distorts our perceptions of risk.”

By Any Other Name

Habit loops. Behavior change. Change models. Seems there are a number of ways we describe the very human phenomenon of laying neural paths. New ways to say the same thing seem to pop up every day. Here are a few:

Charles Duhigg: Cue, Routine, Reward

BJ Fogg: Trigger, Ability, Motivation

My friend’s model of change: There’s Aware; Then aware after the fact; Then sometimes catch yourself; Then eventually stop

John B. Arden: Focus, Effort to change, Effortlessness, Determined to stay in practice

Kurt Lewin: Unfreezing (getting ready to change); Change/Transition; Freezing (or refreezing)

James Prochaska: Precontemplation, Contemplation, Preparation, Action, Maintenance and Termination

Feedback Loop: Data, Relevance (the context of the behavior), Consequence, and Action

Martha Beck: Death and rebirth; Dreaming and scheming; The hero’s sage; The promised land

What is striking about these models is that they all seem to be reinterpretations of classic models.
The story-telling model: Once upon a time there was ___. Every day, ___. One day ___. Because of that, ___. Because of that, ___. Until finally ___.
Or said another way: stasis, trigger, the quest, surprise, critical choice, climax, reversal, resolution.
Or frankly, the hero’s journey (paraphrased and abbreviated): call to adventure, refusal of the call, supernatural aid, first threshold, belly of the whale (bottoming out), road of trials, limited success, temptation, atonement, success, return.
The difference is that these classic models seem to acknowledge the complexity of change and the journey change requires whereas the more modern adaptations look more like quick fixes.

Life Fitness

The benefits of exercise are well-documented, but they tend to focus on the physical. Exercise can also help you with problems in life. It's a "keystone" habit that makes a difference in so much more than your waist line.

The often overlooked but perhaps most powerful thing it does is teach you to be uncomfortable, to confront pain. In How Exercise Shapes You, Far Beyond the Gym, Brad Stulberg breaks it down. 

In a world where comfort is king, arduous physical activity provides a rare opportunity to practice suffering.

The Hedgehog and the Fox

"A fox knows many things, but a hedgehog one important thing." The Greek poet Archilochus

Phil Tetlock, a psychologist, suggests that the fox and hedgehog are examples of different cognitive styles and most MBAs seem to favor the hedgehog - she's considered more of the decisive visionary, while the fox is more nuanced. 

This seems to reduce all of humanity to a binary distinction once again. Seems like a very hedgehog thing to do. 


Laurie Santos looks at evolution by looking at how primates view the world. Now remember these are not our direct ancestors, but a proxy.

Often her work is asking the question, are these other primates as smart as us? For example, primates can count. They also know some simple Newtonian physics.

She's interested not only in how smart we are, but also the downsides of our abilities. Why are we irrational? Can we see seeds of our own economic biases in primates?

We're all walking around with a set of biases, per Daniel Kahneman. For example, we set different reference points - we frame decisions based on how we start; and loss aversion - the pain of loss outweighs the pleasure of gain. These biases are everywhere. 

So she tested monkeys to see if they exhibit some of the same biases that humans do. Turns out that monkeys play it safe like humans and avoid loss, too. Monkeys are often as irrational as we are, but they didn't fall for the pricing effect (when for example people say they like a wine that is more expensive). Monkeys do understand price - they respond to sales. But in her experiments they selected expensive versus cheap food at random. 

What more we can take from this remains to be seen. 

In the meantime, can we change these biases? It's difficult to shut off our intuitions. But Santos and the research shows that setting up different kinds of situations that protect us from ourselves do seem to work - these are nudges. To battle your biases you need to set up your environment to counter-act them. 









On Empathy

Paul Bloom argues that empathy has its drawbacks. It's biased, innumerate, concrete, and myopic. Don't believe it? Consider the reactions to the Newton mass shooting as compared to shootings in Chicago.  It's called the identifiable victim effect. We're drawn to some individuals more than others. We respond more empathetically to people like us. And because empathy is focused on individuals and insensitive to numbers, it's more susceptible to bias.

Okay empathy can be misguided, but isn't it better than nothing? He believes that's mistaken - because he argues that it's focused on current costs at the expense of future costs. 

What's an alternative?  Peter Singer has started a movement called Effective Altruism - it involves both the head and the heart.


Additional reading:

Daniel Batson - Altruism in Humans

Frans De Waal - The Age of Empathy

Simon Baron-Cohen - The Science of Evil


Leslie Jamison - The Empathy Exams







Mental Models

One of my challenges when teaching digital marketing is to convey the importance of a framework for thinking through digital marketing. The foundation can be difficult to pay attention to when there are all these cool shiny marketing tools to play with.

But Charlie Munger puts it best when he says:

... the first rule is that you can’t really know anything if you just remember isolated facts and try and bang ‘em back. If the facts don’t hang together on a latticework of theory, you don’t have them in a usable form.

You’ve got to have models in your head. And you’ve got to array your experience both vicarious and direct on this latticework of models. You may have noticed students who just try to remember and pound back what is remembered. Well, they fail in school and in life. You’ve got to hang experience on a latticework of models in your head.

What are the models? Well, the first rule is that you’ve got to have multiple models because if you just have one or two that you’re using, the nature of human psychology is such that you’ll torture reality so that it fits your models, or at least you’ll think it does…

It’s like the old saying, “To the man with only a hammer, every problem looks like a nail.” And of course, that’s the way the chiropractor goes about practicing medicine. But that’s a perfectly disastrous way to think and a perfectly disastrous way to operate in the world. So you’ve got to have multiple models.

And the models have to come from multiple disciplines because all the wisdom of the world is not to be found in one little academic department. That’s why poetry professors, by and large, are so unwise in a worldly sense. They don’t have enough models in their heads. So you’ve got to have models across a fair array of disciplines.

You may say, “My God, this is already getting way too tough.” But, fortunately, it isn’t that tough because 80 or 90 important models will carry about 90% of the freight in making you a worldly wise person. And, of those, only a mere handful really carry very heavy freight.

Jobs and Degrees

I saw the headline and had to click: LinkedIn CEO thinks U.S. cares about college degrees too much. The text of the article supported the headline.

Which led me to go look at all the jobs descriptions of open positions at LinkedIn. Every single one lists a BS degree in a technical field as a basic qualification.

I'm tired of all these Silicon Valley CEO pronouncements. You think something should change? Start with your own god damned company.


Learn to Change

To do more than survive you have to learn. But the question is how do you learn when you're surviving? Learning also requires that you be vulnerable - open to what others might be able to teach you.

Survival doesn't allow for vulnerability. In our country vulnerability is seen as weakness. The options are fight, flight, or freeze. There's no "learn" in there. No get quiet and listen. No get curious.



This quote from a high income liberal white male in Silicon Valley is the worst [emphasis mine]:

On a related note, I think Trump is a misogynist, and his comments during the campaign were even worse. I am sad Hillary didn't win. But I don't think Hillary lost because she is a woman, and am very optimistic that we will have a female president soon. In fact, I would be surprised if at least one of the parties don't select a woman the next time.


Really? I think his dismissal of the idea that her gender could have played a role is part of the problem. It's like failing to see your shadow side. That just makes it more likely to emerge. 

Marketing and Communication

Want to know where digital marketing is going? Follow the communication trends.

For example:

Mobile phones initially only had text messaging and ringtones. Advertisers found both.

Then smartphones emerged with rich messaging (emojiis) and apps (Instagram/Vine). Advertisers followed.

Now everyone has a smartphone with multi-media messaging (gifs, videos) and several messaging platforms (Snapchat, WhatsApp, Facebook). Notice that apps outside of messaging apps have fallen away. Advertisers are currently trying to understand how to ride this wave.


The Education Thought Process

Here's what I tend to see out there in the education space when it comes to lower socio-economic, mostly minority students:

let's get them to graduate high school --> that's not working so school is not for them

let's get them into college -- > that's not working so college is not for them

let's get them to graduate college--> that's not working so college degrees are not for everybody

let's get them to graduate college and get jobs with their degrees --> no one thinks this way


Music to My Ears

Music affects the emotional centers of our brains, sometimes leaving deep grooves we can reference in the future to feel how we felt when we first heard it. Music works like language does to communicate with the listener - basically sound and dynamics - and even synch with others.

From the Greater Good on why we love music:

“If I’m a performer and you’re a listener, and what I’m playing really moves you, I’ve basically synchronized your brain rhythm with mine,” says Large. “That’s how I communicate with you.”

"...when people listen to unfamiliar music, their brains process the sounds through memory circuits, searching for recognizable patterns to help them make predictions about where the song is heading. If music is too foreign-sounding, it will be hard to anticipate the song’s structure, and people won’t like it—meaning, no dopamine hit. But, if the music has some recognizable features—maybe a familiar beat or melodic structure—people will more likely be able to anticipate the song’s emotional peaks and enjoy it more. The dopamine hit comes from having their predictions confirmed—or violated slightly, in intriguing ways."

College Drop Out Solutions

What Can Stop Kids From Dropping Out: "...passing an introductory course in a student’s major isn’t as good a predictor of graduation as the actual letter grade. The student who earns a B in first-year political science has a 70 percent probability of graduating in that field, while a classmate who gets a C has only a 25 percent chance....Instead of waiting for undergraduates to show up, academic advisers reach out at the first hint of trouble — poor grades, spotty attendance or not registering for the right class — holding 50,000 meetings with students annually....Data showed that first-generation and low-income students were less likely to reach out for help from their professors, so the university hired upperclassmen as tutors....About a thousand Georgia State undergraduates were dropping out every semester because they couldn’t pay the tuition. When a closer look revealed that many were short just a few hundred dollars, the university started awarding small just-in-time grants and financial counseling....higher education institutions should receive public dollars based not only on how many students they enroll but also on how effectively they help students earn a degree"

College Loans and Graduation

It's not what you think. 

The student loan debt crisis is overblown. The real problem is college completion rates. "Dropouts are almost three times as likely to default on their loans as graduates are. It is this subgroup’s debt that ought to be driving the conversation, not the debt of the "average" college student....Free tuition is no solution to the most serious problems we face...College students are not ending up working as baristas"

The Scariest Loan Number "...the typical for-profit student is a 24-year-old from a first-generation family earning less than $40,000, who eventually drops out of school. The completion rates for two-year and four-year for-profit institutions is about 40 percent and 25 percent, respectively....In the final analysis, declining state support for public college fed the rise of for-profit schools, many of which served as factories for dropouts with relatively small amounts of outstanding student debt. These are the people most at risk of default—not the college graduates with $100,000 loan burdens, but rather low-income students who took on a few thousand dollars in debt and didn’t even get a degree." 

Is the Student Loan Crisis Fact or Fiction? "The problem is that we have a lot of people actually borrowing small amounts of money, going to college, not completing [a degree] or completing credentials that don't have labor market value."