Should Is A Terrible Word

I’m not sure who taught me this originally. As with all things I can’t source back, I assume it was my awesome and supportive parents who unconditionally loved and encouraged my wacky and zany child self to develop into this effusive and certain blogger (?) or whatever I am now.

Anyway, something I learned growing up at our house was that:

should is a terrible word.

We should not be in the habit of telling anyone what they should or shouldn’t do. :)  It’s really rude almost 100% of the time when using the word should. You sound hypercritical using it in common vernacular. You (almost always) sound as if you know something that the other person does not and you are trying to enlighten the path for him/her. Even in very specific instruction - i.e. yoga or dance instruction - where there is a commonly agreed upon placement of the parts of the body. “Right elbow to the outside of left knee to twist” -- this can (and should!) be said without a twang of ‘should.’ Should is ableist in this context: it implies one way of doing something. Should is limited and finite; it doesn't leave room for possibility. 

Even if you’re speaking to yourself. Think of the internal dialogue: “I should stop procrastinating and go to the grocery store.” Be kinder to yourself. How about something like: “If I want to eat a healthy meal for dinner tonight, I will go to the grocery store in the next 20 minutes.”

When working with start-ups and founders, I resist the urge to use the word. No matter what I think they should or should not be doing, I try to get them to just talk out their reasoning and logic for making their decisions.  I tell them how I learned something - how I got to a conclusion -- but not what they should do. Some of the best business (and otherwise!) decisions come not from a place of should but from a place of if. Less lacking, more possibility. Less grasping, more optionality.  

By the by, I just looked up what should means -- here it is:

Yeah, fuck should. 

Nonetheless, I like to sit around and think of business ‘should’s’ for big companies. Because it’s fun to dream with limitless potential and with a very wide aperture about what could happen in a free and open world.

Here are some of my shoulds -- let me know yours!! Respond below or Tweet me!

Start ups that Uber Should Acquire

Bird, Lime, etc.

Postmates, Grubhub/Seamless,  AND the top 5 - 10 restaurant chains in each city (byChloe, Sweetgreen, Chipotle, etc.)

Local Messenger Services in cities

Tuktuk’s and Pedicabs Everywhere

Companies that Facebook Should Acquire

All the media companies - starting with the big ones

Production Studios

Sponsorship Model for Talent

Partnerships that Twitter Should Do

News Companies - LOCAL, LOCAL, LOCAL

PR Firms  - breaking news should always be on Twitter - ‘real time verification’

Bloomberg + any other live live financial news

Sports - any other live live sports news

Technologies that Amazon Should Deploy

Basket Technology for crowd-sourced pricing and  Best-Of lists

Those are my 'should's' in today's business landscape -- what are yours?!

Teacher Appreciation Day

My college asked me to write about my favorite Professor as he's receiving a Distinguished Faculty Award this year. Since he's recently been promoted to Interim President of the school, I'm fairly certain he's too busy to read this in between now and when it is published :) so here's a copy for you, in honor of National Teacher Appreciation Day.

It was the greatest fortune in my academic experience to have Professor Pat McGuire as my advisor, my mentor and my teacher.

McGuire brought to life all of the facets of economics in ways that were tangible, lifelong and multidisciplinary. Today, when I walk through the streets of New York City, I see the “ballet of the city sidewalk” in my every step - “never repeating itself from place to place…(and) always replete with new improvisations,”* because he (and Jane Jacobs) taught me to see it that way. He and Professor Spates even took our class to meet Jane! We sat on her porch in Toronto on a beautiful crisp Spring day - what a great honor - and a memory that we will all cherish for our lifetimes.


Because I was his student, I see that companies need diverse representation in boardrooms and in design rooms because, like cities, “(they) have the capability of providing something for everybody only because, and only when, they are created by everybody.”*  He encouraged us to bring our individual backgrounds to our economic studies and the world around us -- because, in fact, the world needs more diversity in thinking, building and dreaming.

2009-08-10 19.48.38.jpg

Prof. McG was the very first teacher I had who challenged the status quo - only after he taught it to me. A memory of this was in Urban Economics -- a difficult class that required quite a lot of work, we were discussing the week’s reading - a controversial book about white flight and the changing American City. Professor McG led an open discussion and after we talked through the various elements of the book, he pondered aloud “well, isn’t anyone going to ask me what I thought about the book?” So we asked, what did he think of the book? “I hated it!” he exclaimed. (Dramatic pause!!!) This was shocking to me - the first (and maybe only) time a teacher ever pulled a bait and switch - in Economics class, no less! He went on to give us good reason to doubt the entire ‘gentrification’ (and underlying racism) that the book espoused. Flash-forward to now, as a 10+ year, very happy resident of America’s largest city, I’m so glad that Prof McG showed us it was possible (and critical) to think differently.

jane jacobs.jpg

I could go on and on about the things he taught us, the ways he ingrained complex topics into our developing minds - the multiplier effect, his laugh, “feel the power” at the Federal Reserve, his intense love for Alan Greenspan, the macroeconomic flow chart, his ability to be my teacher for four years but when election time came, I had no idea who he was voting for. His camaraderie and banter with Jim Spates (and so many other colleagues). Again, the laugh.

2009-08-23 10.16.14.jpg

Besides the things he taught me, though, he believed in me. His great faith in me has propelled me throughout my lifetime. Knowing he is rooting for me and encouraging me - both while I was a student and in my career has been the greatest gift from my time at Hobart and William Smith. For this, I am most grateful.

** With homage and gratitude to Jane Jacobs for many lessons - particularly those in quotes above - and especially the ones learned on her porch.**


Snap to acquire Smule (a big bet)

Have you guys heard of Sing by Smule?  It’s this incredibly sticky karaoke app that’s got a steep subscription model (at $45 a year, it’s 3x the price of The Economist!)


Featuring a huge song catalogue, and a gamified model - singers can sing together and ‘battle’ for singing all the notes correctly - the app is incredibly addicting and also a huge time drain. One song, averaging 3 minutes, might take 3 or 4 tries to get right before you publish it on the app. The whole process can easily eat up an afternoon. (They have also evaded legal issues by having users upload the MIDI tracks of many of the songs - so they’ve relied somewhat on an open source model to build the business.)

My big bet is....

that the next time Snap experiences negative user growth, they will buy a company like Smule. Not for its attractive revenue model. (Although it is an attractive recurring revenue biz). Nor for its audience (I doubt these are unduplicated users to Snap, anyway)...

...But, for time spent on platform metric.

a measurement that, I believe, will increasingly become the only valuable one on social media.


We’re past the scorched earth stage of the internet. The pioneers have gone West - the Lewis and Clark’s have laid claim to each eyeball that has the internet on a phone or a computer. Everyone who is going to be on the internet, is. [At least in America, anyway. (And not babies...yet.)]


We’re now in the new land grab: the one for attention. Only the strong will survive this next frontier - can your content be more compelling than content on any other platform? How much time can you get your users to spend with you? The longer you have them, the more ads you can show them. (See also: Twitter content partnership announcement at NewFront’s 2018).

If you can’t create great content, you’ll have to acquire it...somehow.

Watch this space.

The Green Revolution Will Be Televised

My big bet: There will be a healthy(ish) fast food look-a-like in the late 2020s/early 2030’s. Look to early contenders like by Chloe, sweetgreen, and Quick Fish to set the pace in towns and small cities nationwide. Places like San Francisco, Southern California, Portland, Seattle, Austin and Boston will embrace this experience first...both for their sprawling metropolises and for their high density of young families in the semi-outskirts of the downtown areas. I believe this fast-food company will be ubiquitous - like McDonald’s or Burger King.

Envision a world in which a dad goes to a drive-through for green smoothies on his nap-ride with his 18-month old and a mom picks up a vegetarian-heavy dinner for the family of four on the way home from work. Remember when you were growing up, when you’d stop for a Burger King or McDonald’s on the way home from soccer or a dance recital? It actually felt like a wholesome experience! This will too.

The closest thing to what I’m describing that I’ve know of is Amy’s Drive Thru  -- a drive thru North of San Francisco, in Sonoma County, self described as a restaurant “returning to the roots of American Fast Food, serving lovingly handcrafted food to nourish hard-working citizens, busy families and road weary travelers.” I’m liking this description and might need to make a Sonoma/Napa trip this summer to check Amy’s out in person!

Midweek munching at its finest. #RunsOnLove #AmysDriveThru #PlantPower

A post shared by Amy's Drive Thru (@amysdrivethru) on

Change is a coming - I can feel it, can you? It’s happening to convenience stores, to fast-casual dining, (see also: Sugarfish, Bamboo Sushi, Sardella, Hillstone, etc.) and will be coming to a fast-food restaurant near you.

P.S.  Because this audience is easily affected by gamification strategies, it is wise for these chain restaurants to use a rewards-based system nationwide - like sweetgreen’s - where loyalty to the brand pays of in the form of free food.

Big Bets Volume 1 -- April 21, 2018

The big bet:

Incumbent Airlines will be acquired by Big Banks during the next financial crisis….

Here are my predictions:




(they’ve actually already laid the consumer-facing groundwork + branding for this!)

United + Chase

Delta + American Express

American Airlines + Citi

(*Note - not talking about ‘disruptor’ airlines like jetBlue, Southwest, Virgin, etc. That’s another Big Bet, for another time)

During the next recession, the service industry will get crushed like it always does. In a race to protect margin and keep discretionary spending fueling their credit card business, banks will take extreme measures. Airlines, already operating at close margins, are increasingly incurring unforecastable expenses, (things like TSA delays, costs associated w/ rescheduling customers, vacillating price of oil, regulatory changes, union demands) will be challenged like they always are.

But this time, the government won’t save the airlines like they did after 9/11. Here’s why:

  • competition - upstarts like Southwest, jetBlue, and Virgin keep nipping at the profit margins of the incumbent airlines. The upstarts won’t need a bailout because they run a different and leaner ship.

  • It’s a dog eat dog world out here -- we are operating in a MAGA society where it’s hard to imagine that the Federal Government would bail out commercial airline companies. Welcome to capitalism in 2018, friends.

Enter big banks who have deep financial relationships with aforementioned airlines….they are already trading money for miles! Ponder that for one moment -- by issuing credit cards with mileage points associated with the amount of money a consumer spends on the card, the banks get a pretty healthy insider focus group with which to understand the airline industry….and their acquiree’s business.


Keep your friends close and your potential acquisitions closer, is, I guess, how the old saying goes.

Big Bets

I’ve been making future predictions for as long as I’ve been a walking / talking / breathing human. My poor mother has been listening to these ideas since I was able to formulate them…some early hits include: “in the future, there will be a microwave but for COLD things!” and “there should be a way we could rent a dog for an afternoon!” Other behaviors I embraced from a young age (that mapped to society’s evolution) also included a vegetarian lifestyle and stretching as a form of exercise :)

Along the way, I’ve realized I have other ideas that aren’t so far-fetched. Maybe it’s my process of looking at the past to help predict the future that enables me to observe natural evolutions in products, human behavior and systems. Maybe it’s my intense curiosity about the world we live in.

However they come, I’m starting to canonize these “Big Bets.”

I want a place to archive all these random big bets I, rather than call my mom with all my latest predictions, I’ll put a time stamp on them and throw ‘em up often as I have them. And I’d love to hear your Big Bets! It's more fun to try to predict the future together!


My mother

(the aspirational inventor)


P.S. I attribute 100% of this ‘big bet’ thinking to my mother -- who was the original inventor (and not creator) behind such big ideas as the drive-thru pharmacy.

"It's not like you're going to get a chance to put a pretty bow on it." (...and other reasons to blog)

It all felt too serendipitous this week.

Let me first begin by trying to explain the unexplainable: I met some new friends on Friday night at Bevan’s going away party. Last weekend felt like Bevan’s re-birth: she was off to LA with a kick-ass job and some blonde, blonde hair. It was Easter weekend and I kept thinking my dad would love this re-birth of Bevan.

He never even knew Bevan but I know he’d love her.

Bevan’s friends all came out to say goodbye and Ashley and I really connected with two other girls -- Kate and Jenny. Kate brought a new guy and throughout the night, the talk meandered around Springsteen’s new show, Jenny’s dating life, and Bevan’s big move and Matt - the guy Kate brought - he was a semi-pro baseball player! In between all this, we learned Kate had recently endured hip surgery and she had another surgery coming up soon.

We exchanged numbers with the gals and Ash and I texted the next day with Jenny and Kate - re-affirming our group gut check on Matt: we liked him!! Kate was so happy - they talked about an upcoming hip surgery and she was excited that he was already supportive of her and it.

The next day was Easter and it was cold but promising, like it always is. I kept hearing the bible verse my Dad always quoted - over and over again in my head...

“be not conformed but be transformed.”

The week started like any other one does. Nothing remarkable. On Tuesday morning, we learned our new friend Kate died in her sleep on that Saturday night.

The night after we were all together.

After that and a number of other clear signs from the universe to move - with haste - in the direction of my dreams, I’m writing a blog again. I’ve got some topic terrains I’ll post about regularly (People I Admire, What I’m Reading / Consuming, Big Bets, Yoga Playlists, and Yoga Thoughts) and some random musings along the way.

Please make it a conversation and interact with me - I look forward to hearing your thoughts about my thoughts!


Some inspiration below -- for you to leave your legacy, too:


Bevan, Ashley and me at Bevan's going away party.

Loved this from mother-daughter duo, Hallie Bateman and Suzy Hopkins, "What To Do When I'm Gone."

Our friend Kate's brilliant music blog, NYC Melody - where she featured great playlists, fantastic top 10 lists and prescient obits after musicians died. Heartbreaking to read and realize this great mind is no longer with us.


NYC Melody by 

Katherine Wilson

Hope you'll stay in touch as I begin to write about the world around me and my observations of it.

<3 G

some great content for your weekend...

Patti Smith on the BBC yesterday... "Loss is something we never get over."

Barb Corcoran speaking the truth!! (Lo Siento if you too are exposed to the espanol ad before the real content!)

loved this (second ever!) New Yorker podcast with Amy Schumer & Jorge Ramos. hosted by New Yorker editor, David Remnick on WNYC. loved the part where Ramos says his yoga breathing helps him keep his calm in stressful on-camera situations :) 

i find this kind of thing amusing and proof that we are still in such an early-early internet landscape. we are just barely toddlers - learning to police ourselves and things like copyright law are hard to find relevant in the digital age.  and the beat goes on.

dynamically stable systems -- my tribute to Jane Jacobs


I've always been inspired by Jane Jacobs' observation of cities and economies. Her thesis in her work, The Nature of Economies was around dynamically stable systems and how they avoid collapse.  

Efficient ecosystems do four things, she said:

  • bifurcate
  • create positive feedback-loops
  • ensure negative controls
  • adapt to emergency

It occurred to me after hanging with my friend (and Summit roommate!) Leyla Acoroglu:

^^ my awesome Summit roomie


...that we all live in many independent and efficient ecosystems everyday.  Our world, of course, the largest and most common denominator ecosystem that we all share.

The environment, atmospheric conditions, our garbage production and carbon emissions we know and collectively acknowledge affect us now and will affect us in the future.


We're each individually members of concentric circles - institutions of learning, groups of friends, people bound by shared interest or property.  They are, though, not as independent as we may think they are.  They need common denominators to function, people to bind them.

They are, in fact, more like interconnected concentric circles with multiple points of crossover and connection.


Bifurcation happens when we begin to identify in different circles or groups...technologist, teacher, athlete, mom...our individual identities (chosen and unchosen) begin to allow us to see similarity and difference in each other. My friends who are having babies are joining a new group 'mother' - which will now be an identity they share with mothers all over the world.

When we receive positive feedback that these groups are working (mommy groups, lobbying groups, athletic endeavors like a marathon), we double-down. Technology is like this too: we find a market-segment need and solve for it.

With regard to technology, Uber is a perfect example of these first two steps in Jane's theory.  Bifurcation occurred when Uber's co-founders observed a need in the market: a cab to their location in Paris. The trial runs for Uber perfectly mimicked the market conditions we'd hope for: since Uber's founders basically disregarded the established Taxi and Limousine Commissions that govern local taxis, they were able to receive positive feedback fairly quickly validating this was a worthy idea. The positive feedback loop was validation enough to continue to grow this emerging company...Thusly, ensuring negative controls were in place. By the time the government and regulating bodies came to call, Uber was a profitable company - able to hire the talent they need to keep Uber in major cities.  Therefore, adapting to emergency has become second nature to this company that seemingly can know no bounds...

Back to mommy friends, the groups we create for ourselves in small and large help us to create dynamically stable systems...and ones that we feel safe in.