Driverless Cars and the Great American Road Trip

Photo by Doug Kerr via Flickr

I went back to Williams this past weekend for a rugby reunion. Lately when I go back, I like to fly into Boston or New York (vs. Albany which is closest), and tack on an extra day to see friends. In theory this is about making the trip from the West Coast worth it by seeing more people, but in reality it’s just as much about the drive.

The Taconic is one of my favorite stretches of road. The first time you drive it you can’t quite place what makes it feel so different from other roads. Then it hits you: there are no shoulders. Two feet to the right is a curb, and then grass. It makes for an incredible feeling when driving, so little separating you from nature.

Something amazing happens when you take a drive like this. Your mind has to focus just enough on the road and how fast you are driving (because OMG the Taconic is cop city!) that the rest of your mind is free to wander. To drift off into neglected corners, resurface long-forgotten memories, and offer up weird ideas, steered only by the sights out the window, the soundtrack playing, and sheer freedom.

And it got me thinking: what does a driverless car future mean for the Great American Road Trip?

I have taken dozens of road trips throughout my life. The cross-country trips during college from Massachusetts to California and back. The trip that only lasted 10 miles before my Jeep’s engine melted in a freeway-side fire. Down and back up the East Coast visiting friends. The trip where we spilled a bottle of cleaner the first day, ensuring that our Vanagon smelled Fantastik® the whole week. The 15-hour trip from Chicago to my summer internship in Florida where I needed to drop off my stuff at an apartment then get to the airport to fly to a Williams reunion, only to miss my flight by ten minutes. I-40. 70. 80. 90. And I swear I will do the 10 at some point.

“It’s about the journey, not the destination” is often applied elsewhere as a metaphor, but in the case of the road trip, it’s literal.

It’s about stopping to check out the miniature donkeys you just saw a sign for. It’s about finding that great local diner. It’s about just once admitting when checking into a motel that you really have six people, not four – and they offer you a room with three queen size beds side by side!


And when it’s just you, it’s about putting your playlist on shuffle and letting each song unlock and replay an old memory.

So, as much as I’m excited for the time when driverless cars mean I don’t have to sit in traffic or endure a tedious commute, I don’t want to lose the magic that only a long drive can bring.

There is value in letting your mind wander. There is value in spontaneity. And there is value in being present for the actual, literal journey.

How to Explain Machine Learning to an 8-Year-Old

apples Photo by Holly Mindrup via Unsplash
Photo by Holly Mindrup via Unsplash

Loved this question I got at a recent interview: “How would you explain machine learning to an 8-year-old?” Here is my take on it:

Machine learning is about teaching computers to work more like our brains. What’s so cool about our brains is they have the ability to combine information to come up with new ideas.

Let’s say one day in school you learned all about apples.

And the next day at school you learned that if you steamed and mashed the apples you could make applesauce.

And the next day at school you learned about bananas.

Your brain might then get the idea “hey, if I mashed up the bananas I bet I could make bananasauce!”*

Your brain didn’t need to be taught that idea. It combined information it had to come up with that new idea.

Machine learning is about teaching computers how to do just that.


*not a mainstream dish, but tasty nonetheless


Building a Ruthless Culture


Anneke Jong of Reserve gave an epic masterclass on building a great culture at the LAUNCH Festival last week. Wanted to capture the essential takeaways here.

Ruthless Welcoming – all about onboarding and consistency

  1. Everyone meets the foxtato
  2. Make docs for everything – if you find yourself repeating things, write it down
  3. Playbooks for every role – at Reserve, a GM for a new city is given a playbook outlining what their first 3 hires and 25 restaurants should look like

Ruthless Sharing – share the wheel vs. reinvent it

  1. Role-specific national summits
  2. Role-specific weekly video hangouts
  3. Role-specific emails lists and Slack channels

Ruthless Camaraderie – one team, one dream

  1. One-hour values & vision session with each new team member during onboarding
  2. Monthly all-hands town hall – remind everyone of the shared North Star, not just what’s changing but what hasn’t changed
  3. Standardized, easily accessible KPIs sent out weekly (Reserve uses Looker for the dashboards)

Many of these are very simple, straightforward things to do, but when you put them all together they add up to more than the sum of their parts. They help create habits that reinforce the culture you are trying to build, and they help maintain that culture as you grow and bring on new people.

And if you ever get a chance to see Anneke give a talk, do it – outstanding presenter, hope to see her back at the LAUNCH Festival again next year.

4 Ways Freshpep Can Improve the Shopping Experience

Organic grocery delivery startup Freshpep features beautiful-looking produce and nicely highlights the savings its passing on to the customer, but there are several confusing points a first-time shopper will encounter.

Here are four ways Freshpep can improve the shopping experience for its customers:

  1. Remove menu overload confusion
  2. Remove unit/quantity confusion
  3. Remove savings confusion
  4. Remove checkout confusion

Let’s dive in a little more on each area.

#1 Remove menu overload confusion


The first thing you notice after getting past the home page (more on opportunities there another time, perhaps) is that you land on a page with multiple menus. Across the top it’s very clear you are in the vegetables category, but the left nav is less clear (broccoli is considered “Greens” but asparagus is buried in the “Vegetables” catch-all).


In fact, a lot of staples like tomatoes, avocados and brussels sprouts are grouped into the “Vegetables” catch-all, only to be found by super-scrollers or ones committed to using the search bar.

Suggestion: Add some sub-descriptor text to the left nav with additional keywords to help people find what they are looking for. Also, the entire experience can be overwhelming – you may want to consider offering an option for people to get a sample basket of some of your most popular items, kind of like what CSA services offer. Could also explore integration with recipe sites as their backend fulfillment – anything that makes it easier for customers to put together combinations of goods without having to search/click a million times.

#2 Remove unit/quantity confusion


When viewing the smaller listings, it’s often hard to tell what the unit of measurement is. And if you just click the “+” three times thinking you are adding 3 onions to your cart, you might be surprised by what you actually get.


For example, I thought the onion listing was $1 each, but in reality it’s by the pound. For items like onions and peppers, normally I would go to the the store intending to by three onions, 2 peppers, etc.

Suggestion: The smaller card listing view should include the unit of measurement; some items should be switched to be listed as “$x/each” rather than by the pound; for items sold by the pound, ideally there would be an indicator of how many that is (e.g. 1 lb is 2-3 peppers).

#3 Remove savings confusion

The savings for each item are clearly communicated, but there’s a volume savings message that’s getting lost.


Suggestion: A simple way to improve this (and also increase sales) would be to show the escalating percentage savings in the quantity drop-down menu.

#4 Remove checkout confusion


After adding some items to my basket, I went to see what the checkout experience was like. After reviewing the items in my basket and clicking “Checkout” I was asked to login or create an account. Ok, pretty standard so far.


But after creating an account I was taken to the “My Account” page. It didn’t remember at all that I was trying to checkout. Frustrating to have to work harder to give you my money.

Suggestion: Never get in the way of someone trying to give you their money! The system needs to recognize when someone creating an account is in the checkout stream and take them to the next step in that process.


This is part of an ongoing series where I explore marketing ideas and web usability improvements and/or trends for companies in the Food Tech space. My full Food Tech Landscape deck is posted on Google Drive if you are interested.

Point/Counterpoint: On Grabbing Life by the Horns

“Most men lead lives of quiet desperation and go to the grave with the song still in them.”
– Oliver Wendell Thoreau 🙂 [I know that’s not a real person, the above is actually a misquotation blending a Thoreau passage and an Oliver Wendell Holmes line]
I am not throwing away my shot
I am not throwing away my shot
Hey yo, I’m just like my country
I’m young, scrappy and hungry
And I’m not throwing away my shot
– from Lin-Manuel Miranda’s Hamilton

Why some of us don’t have one true calling

I just watched Emilie Wapnick’s TED talk on multipotentialites – people who have always struggled to answer the question “What do you want to be when you grow up?” because there was never just one answer.

I love the way she frames up three multipotentialite superpowers:

  1. Idea synthesis
  2. Rapid learning
  3. Adaptability

Love it because as I try to course correct on my career to get back to something I’m passionate about, these are exactly the same three strengths I keep coming back to time and again. I’ve often described it as connecting dots others don’t see, or being given the messier problems that more linear thinkers can’t deal with because of a quick learning curve and ability to deal with chaos and ambiguity.

Big thanks to Bernadette Cay’s Medium post and list of resources on this topic.

5 Marketing Ideas for Zesty

As I try to make the move to an early-stage startup, one of the areas I am loving diving into is the Food Tech space. This is part of an ongoing series where I’ll explore marketing ideas and web usability improvements and/or trends. My full Food Tech Landscape deck is posted on Google Drive if you are interested.

Zesty is a company I’ve gotten to know a little more lately – awesome, down-to-earth people, and seems like they are really emphasizing culture as they grow. Here are 5 (mostly) quick wins that I think could help them grow.

  1. Test a shorter form asking for less information
  2. Build a Slack app to engage people where they work
  3. Feature top CTA in top nav and remove clutter
  4. Update main page text with How it Works copy/cues
  5. Give people outside of SF a way to get notified

Let’s dive in a bit more on each of these.

#1 Test a shorter form asking for less information

Ten fields (and having to scroll down to complete the form) may ensure you only get serious leads, but may also cause many to abandon the form (and it’s a missed opportunity to build pipeline and nurture companies that are somewhat-interested). Trim it back to just what you really need to get the conversation started.


[Update: Looks like they have done this since I originally put this together in January. Much better with only six fields!]

Screen Shot 2016-02-18 at 4.41.39 PM.png

#2 Build a Slack app to engage people where they work

As Slack continues to grow (especially among the startup community), it becomes a natural place to engage people where they work. But it doesn’t look like any competitors are there yet, my searches for “food” and “lunch” came up empty. I would need to know more about your operating model and order cutoff times to think more about how this slack bot would actually be used, but happy to brainstorm with you! It could also be used as feedback mechanism, or be connected with other healthy eating services/trackers in the digital health space.



#3 Feature top CTA in top nav and remove clutter

What’s the most important thing people are here to do? Let’s make it easier for them to do it.


#4 Update main page text with How it Works copy/cues

You lead with the benefits, which is great, but the details of how it works may be getting lost. Many food tech websites feature content like this as a How it Works blade, almost all the How it Works examples I’ve found (some below, more analysis to come on that later) include “1, 2, 3” visual cues to convey simplicity.


#5 Give people outside of SF a way to get notified

Your form makes it clear you are only in SF, but doesn’t invite people to be notified as you grow (maybe if they fill it out they are added to a list, but it’s not clear). It’s a missed opportunity to build email list, and could also act as an indicator of where to expand to next. Below is a nice example from Sprig of simple prompt for email address if outside of their service area.


That’s all for now, let me know what you think!

Hey UrbanSitter, how about a White Flag button?

It usually hits on a Sunday. Whether you’ve just hit max on your whining threshold, or have been flying solo because your partner has had to work all weekend, all of a sudden a wave crashes over you.

Fuuuuuck. Why didn’t I line up a sitter?

It’s that moment when you would give anything to have a sitter show up and take them off your hands for a few hours.

You want to wave the white flag and surrender.

So how about it, UrbanSitter?

How it could work:

  • After you’ve used a sitter, you mark in your profile whether or not you want them added to your White Flag list (sitters also opt in/out for White Flag alerts)
  • When desperation sets in, you open the UrbanSitter app and hit the White Flag button
  • A notification goes out to all the sitters on your White Flag list
  • If a sitter is free and wants the immediate work, they can reply to accept the job
  • May want to geo-bound the list to an area where a sitter could get to a White Flag job within 30 minutes
  • You could also do the notifications in reverse, with a favorite sitter throwing parents an optional lifeline

Instant relief for parents. More jobs for sitters. And from a business perspective, it acts as an incentive for parents to post more jobs in order to build up a big enough list to make this killer feature work for them.


Key Takeaways from the NewsCred #ThinkContent Tour SF

I’m a little delayed on this, but wanted to capture and
share some of the best takeaways from this awesome event.

The New Consumer: How Understanding Consumer Behavior Can
Help Connect You To Your Audience

Cenk Bulbul, Head of Strategy & Insights, Ads Marketing,

  • Consumer needs are…immediate, purposeful,
  • Content should be…informative, authentic,
  • Model for thinking about how your content maps
    across the customer journey:
    • Hero – entertain and inspire
    • Hub – regularly updated destination with
      valuable content
    • Help – answers to consumer question
  • Good to know: lots of data available at

Speaking To Millennials: Why It Matters & Strategies For

I initially wrote this session title as “Speaking with
Millenials” which in retrospect probably would have been a more accurate
participle to choose. Anyway, this was a panel discussion with Hamilton Brown
from Taco Bell, Eric Toda from Airbnb, DJ Capobianco from Twitter, Annie Lee
from Pinterest, and Eric Oldrin from Instagram, moderated by Sarah Frier from

  • Don’t encourage them to story tell, encourage
    them to story make (have adventures) – Eric Toda, Head of Global Social
    Marketing, Airbnb
  • You don’t want to walk into a party and just
    talk about yourself – Eric TodaThink about grouping users by ethos, not by age
    – Airbnb has Identity Voyagers, Pioneers, and more
  • Let people have fun with your brand and poke fun
    at it – Pinterest highlighted and celebrated “Pinterest fails” Halloween
    costume attempts
  • Real-time = a great opportunity to deliver value
    to your users, and capture great everyday moments that can be turned into
    future content – Airbnb sent a helicopter for a stranded user whose lodging
    fell through

The Era of Amplification and Personalization

Jason Miller, Senior Manager, Global Content Marketing
Solutions, LinkedIn

Highlight of the day for me. Beyond the great content
marketing advice, this was a master class on how to give a kickass presentation
while also cementing a distinctive personal brand. His blend of content
marketing expertise with metal/rock gods (exploding pie charts, anyone?!?) was
memorable, valuable and fun. Some choice takeaways:

  • When did we all forget to be interesting?
  • Be the best answer to the question on your
    customer’s mind
  • Content marketing is easy; being interesting is
  • Repurpose content like leftover turkey – start
    with a Big Rock, then lift/repurpose to create turkey slices

Big Things Happen When Content Meets Data

Peter Krmpotic, Senior Product Manager, Adobe Experience

This was primarily a discussion about how channel
proliferation drives a need for tools to help manage it all. Biggest takeaway
for me was a model for thinking about making messages channel-specific.


How to Plan & Build Your Content Marketing Strategy

Liz Bedor, Content Marketing Strategist, NewsCred

A great walkthrough of their model – you can check it out on
SlideShare, so just a few points here.

  • Love this quote: “We need to stop interrupting what people are interested
    in and be what people are interested
    in.” – Craig Davis
  • Content is currency, something you can give
  • Calculate the cost of unused content, steal
    budget from underperforming content
  • Go back to basics and answer your customers’
    questions – be helpful! A good slide/framework for working through this:
    • Persona –> Stage –> Questions/Concerns –> Keywords
    • Then evaluate if you have content that answers
      those questions and will rank for the corresponding keywords – and if not,
      build it

Redefining the Rules of Marketing

Shafqat Islam, Co-Founder & CEO, NewsCred

I’ll just wrap with one takeaway here, which pretty much
sums it all up:

“If you think your product is the thing you sell, you will
be disrupted. Your product is the customer experience.”

Great event – if you are in London or Chicago see if you can
request an invite to their upcoming stops on the #ThinkContent tour!