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?!

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.