The Big Kahuna: Humanity in Business

After posting a very personal article to LinkedIn last week and not only watching it become the most popular thing I’ve posted but also elicit highly personal responses from others, including complete strangers, I’ve been thinking a lot about humanity in business and in life. I may be writing more on this, but in the meantime, it made me think of this monologue from the movie The Big Kahuna.

“If you want to talk to someone honestly, as a human being… ask him about his kids. Find out what his dreams are. Just to find out. For no other reason. Because as soon as you lay your hands on a conversation to steer it. It’s not a conversation anymore. It’s a pitch, and you’re not a human being, you’re a marketing rep.”

Lavender mums

My Dying Mother, My Startup, and the Best Advice I’ve Ever Gotten

It’s Halloween again. The day my mother died, five years ago.

She died of pancreatic cancer, brutally and mercifully, three months after she initially felt sick, and just six weeks after we figured out what was going on. Brutal, because it was so quick. Merciful, because it was so quick.

I was running a technology startup at the time. I was CEO, which stood for “Chief Everything Officer.”

I was spending a lot of time at the hospital in Richmond, VA, returning to work in DC every few days. I was attempting to spend as much time as I could in both places, and both situations were suffering for it.

Sitting here, five years removed, it’s easy to look at the situation and know what to do. It’s likely obvious to you… Spend all your time with your mother. Of course, right? But at the time, it wasn’t so clear.


On Labor Day 2012, we knew my mother was sick, we just didn’t know how very sick. You read books about people with cancer, and they say things like, “they gave me six months to live.” What you don’t realize is that this is: a) a wild-ass guess; and/or b) not an estimate, but a maximum.

The other thing you may not know, if you’ve never gone through something like this, is how much hope and denial you have in the moment.

Had my mother gone through an unsuccessful surgery and countless other procedures that did little or nothing? Yes.

Was she on massive doses of a complicated narcotic cocktail, including a morphine drip and a patch that fed her a steady stream of fentanyl, the drug getting attention these days about being so much stronger than heroin it kills people? Yes.

Was she transferred to the palliative care wing of the hospital, where they no longer treat the disease, they simply focus on pain reduction? Yes. (Pro tip: When this is good news, you know things are bad.)

But she was also having really good days where she was lucid, or would actually eat something, or would ask to be wheeled outside so she could arrange flowers, or we’d get good reports about her bilirubin, or some other obscure medical topic I had become a micro-expert in at the time.

Hell, maybe she’ll fight this thing into the New Year?

So, you hold on to that, not all the other stuff. You have to.

And you just don’t know. Now I know. Now I know what to look for. What weeks, days, and hours away from death looks like. Back then I didn’t.


The company was at a very fragile stage itself.

We were very small. We had big clients and some big contracts but revenue was uneven, and we were in the middle of completely revamping our product and engagement model.

We were also in the middle of a startup accelerator program. For the unfamiliar, these programs give (or loan) companies tens of thousands of dollars with the expectation, or at least the hope, that they turn it into millions of dollars. The culmination of these programs are “Demo Days,” where you travel the country to present in front of rooms of potential investors. Demo Days for my program were mere weeks away.

We had three employees, one of whom had a child on the way. If you’ve ever been responsible for payroll, you know the pressure of supporting your employees and their families. I had written personal checks to make payroll at times.

People were counting on me to either give, or make, them money. Not only that, the sole focus of my life, indeed my identity, for the last four years, was this company.

If there were bets on whether my mother or my company would die first, I’m not sure which would get better odds.

CEO of Mom’s Happy, Inc.

You’re sitting there rolling your eyes or yelling at your computer. You know what you would do. You have no doubts. That’s because you’re not going through it right now. I needed help making a decision at the time.

Luckily, I had a trusted business mentor and personal friend that was perfectly equipped with the combination of context and confidence to help me sort this out, and we had settled into a habit of getting together for drinks during my stints back in DC.

I had a decision to make. I couldn’t keep splitting my time. What should I do?

The advice my friend was: Your job right now is to be CEO of Mom’s Happy, Inc.

No regrets

I spent the last three weeks of my mother’s life with her.

I didn’t respond to a single work email. The only calls I made were to tell my employees and investors that I would not be at the first Demo Day presentation. (I would be at the subsequent ones in San Francisco, NYC, and Boston, a week later.)

I don’t regret it for a single second.

I love you, mom. Happy Halloween. (My mother loved Halloween.)

Tree with exposed roots

We’re On The Same Team

Years ago, after one of those silly arguments all couples get into, my wife and I made a rule for ourselves. No matter what the disagreement, we must always keep in mind that we are on the same team.

We may vehemently disagree with the other about the topic at hand, but fundamentally, we are in this together and reaching for the same goals. We are both trying to improve the relationship and push our shared goals forward, even if the way we do it may differ or if we make mistakes along the way.

We’re on the same team.

This creates a foundation of understanding and trust, a lens through which to view flare-ups and screw-ups, and a way to move forward together.

That escalated quickly

Years later, I had a situation at work that could have used this foundation. A person on my team screwed up. I don’t remember exactly what the incident was, but it was minor.

The Account Executive on the account stormed into my office claiming that both I and my direct-report who had made the error were sabotaging the project, that my direct-report should be fired. To top it off the AE questioned my abilities as manager (this person had never managed a team).

I didn’t know where to begin. I was angry at the accusations and the mountain-out-of-molehill nature of them, but knew I had to find a way to calm this person down (they were on the verge of tears) and make progress on resolving the issue in the short-term and keeping an effective working relationship long-term. This wouldn’t be the only project we worked on together.

Root cause

I couldn’t help but be reminded of the arguments my wife and I had gotten into. The AE wasn’t concerned over the actual mistake, she was expressing a much deeper concern. I took a deep breath, asked the AE to calm down, and told them the story about me and my wife (with more detail than I did above).

First off, this took us both out of the heat of the moment so we could calm down and gain some perspective. Second, I was sharing a personal story; opening yourself up emotionally is always disarming. Third, it gave us a productive way forward and allowed us to address their concerns.

Most importantly, it addressed the root cause. This was not about a missed deadline, a website error, an unsent email, or whatever the actual mistake was. This was a trust issue. The true problem, that would continue to come up if unaddressed, was that the Account Executive did not think, did not trust, that we shared their goal.

I reminded them that no matter what happens, even if someone screws up, we have to go into every discussion with the trust that we’re on the same team, we all want the same thing: a happy, successful client.

We’re on the same team.

Trust + shared goals = happy client, happy team

Unfortunately, this wasn’t the last time this happened with this Account Executive. I, and others, had multiple tear-soaked run-ins where minor mishaps were turned into catastrophe and career questioning. Now we all had a useful shorthand to diffuse the situation and remind everyone what was important. It became our mantra:

We’re on the same team. We’re on the same team. We’re on the same team.

Photo courtesy of Wikipedia

Kandinsky abstract art

Empathy & Ego: What I Learned During Six-Hour Art School Critique Classes

All sophomore photography majors at the School of Visual Arts are required to take a six-hour critique class. From 9am to 3pm every Thursday, with brief breaks for snacks and smokes, a steady stream of aspiring Avedons tack their work to the wall one by one and defend it against the jaded questioning of the thirty or so others in the class.

The six-hour critique format was brutal and by design.

If you were lucky enough to present during the first hour, before the coffee had kicked in, you could expect to get through the proceedings without too much trouble. Hour two would bring raised voices and lots of, “But whyyy did you choose to do that?”

Yelling was to be expected by the pre-lunch hour, when people were fully caffeinated and starving for calories and cigarettes. By hour four, the gloves were off and tears weren’t uncommon.

Ego is an Impediment and an Imperative

Great artists figure out their best work is an extension, a reflection, of themselves. It is quite a trick to both be and create that mirror (a mirror, not a movie, big difference).

This is why it is so hard to hear thirty caffeine-fueled, nicotine-starved self-proclaimed artists rip apart, sometimes literally, the work you put on the wall. It is not a piece of paper up there, it is literally you on that pockmarked wall, crucified by thumbtacks.

Eventually, we learn we must put all of ourselves into the work and then separate ourselves from it.

We learn our ideas aren’t sacred.

We learn we are a work-in-progress.

We learn others can help us improve.

We learn ego is an imperative and an impediment.

This is as true for the artist as it is for the entrepreneur or the designer, the intern or the CEO, the husband or the wife, the student or the teacher.

Empathy is a Superpower

Empathy, the word, is adapted from “einfühlung,” a German word coined by an art critic, imagine that, looking for a better way to talk about and understand art. In order to do so you must project your yourself into the art. Einfühlung translates as “into feeling.”

Empathy then is not simply sharing or understanding the feelings of another. The Oxford English Dictionary contains this early, fantastic definition:

The power of projecting one’s personality into (and so fully comprehending) the object of contemplation

You catch that? Empathy is not an emotion, it’s a power. It requires you to not only understand the object, but crucially, empathy requires that you understand yourself.

Two Key Lessons

I didn’t become a professional artist, but the lessons from this marathon class arise almost daily in my professional life as a marketing / product development executive, team leader, and mentor.

  1. Put your best work out there, but understand that no idea is sacred. You must accept the fact that your idea can be, will be, improved by revealing it to others.
  2. When giving feedback, fully understand both what the creator is trying to achieve as well as what you are bringing to the discussion.

None of these things were in the syllabus. Wisdom only comes with time.


Thanks to Fawn Potash, the professor of my sophomore critique class. 

Thanks to Jon Budington, for originally exposing me to the word einfühlung and the true meaning of empathy.

Why I Love The Wirecutter

I am an over-researcher of even the most mundane purchases. Whether it’s a travel coffee mug that costs less than $30 or a pair of audiophile-grade speakers that cost more than most people make in a month, I spend more time pouring over online reviews, product manuals, photos, and price comparisons than most spend picking a name for a child.

I am also the type of person who, once I do all this research and eventually make my purchase, will tell everyone who is (un)fortunate enough to mention that they too are in the market for an [insert product here] everything I learned in my weeks or months of research, god bless them. I will often follow up with an unsolicited email of links and information, because, well, I did all the research not just for me but so I could pass it along to others.

This makes me what author and pop sociologist Malcolm Gladwell would call a “maven.” Someone who “people … rely upon to connect us with new information,” is “almost pathologically helpful,” and as a helpful Wikipedia author put it, “start ‘word-of-mouth epidemics’ due to their knowledge, social skills, and ability to communicate.”

At one point, years ago, this proclivity manifested itself into a website that I edited and wrote with two friends called, “Degeeked: Simple answers to tech questions.”

Tired of product advice and review sites giving multiple choice answers to simple questions like, “I have $200, what camera should I buy?” or giving explanations of how the entire Internet works in response to “how do I setup my wi-fi router?,” our answers were aimed squarely at, well, the types of people who ask questions like this. These people are looking for answers, not an associates degree.

Degeeked never fulfilled its destiny as the end-all be-all product advice site on the internet. That designation, at this point, has to go to The Wirecutter and its sister site The Sweethome. The only proof you need is that The New York Times bought them for more than $30 Million in 2016.

As a compulsive visitor to the site (if I enter “t” into my browser, guess what website is at the top of the autocomplete list), I wanted to explore what about The Wirecutter makes it so great.

The Wirecutter autocomplete


1. Authority

The cornerstone of The Wirecutter’s success is that you trust its recommendations. Without authority, nothing else matters.

The fact that the site is owned by The New York times and was started by a former editor at Wired and Gizmodo offers credibility, but that’s not quite authority. They know this and put a “Why you should trust us” section at the top of every review.

Let’s check out a couple of these to demonstrate the lengths to which they go in order to provide authoritative information. Here’s the “Why you should trust us” section for “The Best Exercise Ball,” a $40 product:

In addition to surveying the peer-reviewed literature on the effects of exercise ball use on muscle activation, posture, and pain, we consulted several experts with more than 50 years of collective hands-on experience. We spoke with Marilyn Moffat, PhD, a professor of physical therapy at New York University and former president of the World Confederation for Physical Therapy; personal trainer Grace DeSimone, editor of the American College of Sports Medicine’s Resources for the Group Exercise Instructor; kinesiologist Danielle Fournier, co-founder of the Ballon Forme exercise program and author of Ballon Forme Couples Method: Guide to using the birthing ball during labor and delivery; and Brian Lowe, PhD, a research industrial engineer in the National Institute for Occupational Safety and Health’s Applied Research and Technology division.

This one is by far my favorite, found in a review for banana plugs. Banana plugs.

I’ve reviewed audio gear professionally since 1990, and I’ve been doing laboratory measurements of audio gear since 1996. I have thousands of hours of experience at the test bench, and I keep a full suite of audio-test gear in my home. Just as important, I’ve been building audio gear since about 1975. For decades, I’ve been making my own speaker cables, usually with pro-grade cable and banana plugs I put on myself. I’ve also held two jobs in electronics-assembly factories, where I often spent hours a day terminating cables. As an audio reviewer, I’ve tried innumerable brands and types of banana-plug–tipped speaker cables in innumerable speakers and amplifiers, so I’ve seen what works and what doesn’t.

And here’s where it gets weird: I’m a longtime connoisseur of banana plugs, having sought out cool new designs in markets around the world, including Tokyo’s Akihabara district, Seoul’s Yongsan district, and New York City’s Chinatown, as well as on numerous websites. Even before I undertook this project, you could probably have found at least a dozen types of banana plugs if you dug through my lab.

See what I mean? This dude has spent more time learning about banana plugs than you or I have spent eating food, and you didn’t even know what banana plugs were 30 seconds ago!


2. Utility

The Wirecutter is just plain useful. And for everyone.

Unlike most sites of this ilk, they aren’t category-specific or geared toward one type of audience. There aren’t just techie gadgets, or just home theater products, or solely things for red-headed mothers of twins who practice yoga.

A quick sampling of the items highlighted on their home page: wireless earbuds, dishwashers, hiking first-aid kits, cheap laptops, baby bottle warmers, dog nail clippers, cell phone plans, and DNA testing kits.

All that variety—there are over 156 items listed on their home page, not counting stuff in the sidebar—could be overwhelming, but for the site’s excellent categorization scheme. Those 156+ items are neatly organized into 25 well-chosen categories and sub-categories. Here’s a sample:

The Wirecutter categories


Their on-site search functionality is a let down most of the time, but like most people, I use Google to search their site.  Just like I do when I’m trying to find something on Wikipedia, my default search pattern when searching for product recommendations is now, “[product type] wirecutter.”

And because of their authority, Google rewards The Wirecutter by reliably returning their pages in search results:

The Wirecutter google search


As you can see, The Wirecutter’s on-site search doesn’t fare as well:

The Wirecutter search results


We all need something to strive for to make us better.


3. Transparency

How often have you read a product review and wondered if there’s a quid pro quo going on between the site and the product manufacturer? Sure, site’s are required to disclose these payola arrangements, but they often do so in barely visible ways.

At the top of every single page on The Wirecutter, is an explanation of how they make their money:

When readers choose to buy our independently chosen editorial picks, we earn affiliate commissions that support our work. Here is an explanation of exactly what we do, and how to support our work.

Transparency = trust.

The Wirecutter makes money when you click on the links they provide and buy the products they recommend, which seems only fair and completely reasonable. At this point in the commercial internet’s history we know that no one would actually pay for a service like this no matter how useful or valuable, which is shameful and insane but the reality, so this seems as close as we’re going to get to direct payment for services provided.

Yes, The Wirecutter does have ads, but you have to look for them, and they don’t do anything shady to trick you into clicking them or increasing their impression counts.

Then there are the lengths to which these crazy people go during their own first-hand testing.

For the banana plugs (it’s fun to type, what can I say) they started off with 18 different kinds. The aforementioned exercise ball experts started off with a list of 80 products! A separate set of compulsives spent 150 hours testing cutting boards, which… what?!

The Wirecutter cutting boards

Each recommendation is accompanied by a few sections that ratchet up the transparency even more. In addition to the “why you should trust us” section, there are: how we picked, how we tested, the competition.

Just like in math class, sometimes how you got the answer is just as important as the answer itself.


4. Respect

The above are all an extension of The Wirecutter’s respect for its audience. Respect for me, the visitor, is what keeps me coming back almost daily.

This respect is palpable as soon as you land on their home page.

Almost every single product review site makes you click into the article to find out what their recommended product is, and because of The Wirecutters authority and utility, no one would fault them for doing this. But I wouldn’t be talking about them in such glowing terms if they did.

Right on their home page, for the main featured item as well as every one of the other 156+ “best” products listed, they tell you which product they recommend. If that’s all you need to know, no further clicking required.

The Wirecutter home page
Quick, what’s their recommendation for best cell phone plan?


Once you dive into a review detail page, the magical synergy between their business model and their respect for the visitor aligns comes into full view.

Most places bury their recommendation at the bottom of the page, that way they can serve you more ads. But The Wirecutter makes money when you click on links to their recommended products and buy the products they recommend.* So, it behooves them to put those links, and the supporting information, in front of you as quickly as possible.

Burying the lede may work for their parent company, but it’s not The Wirecutter’s style.

The Wirecutter earbuds


Mission accomplished

At the top of every page on The Wirecutter and The Sweethome, is their simple mission:

The Wirecutter and The Sweethome … are lists of the best gadgets and gear for people who quickly want to know what to get.

Through the synergy of authority, utility, transparency and respect, mission accomplished.


Note: While this post was being written, The Wirecutter announced that they would be combining their two sites into one under a single name: Wirecutter. In the announcement, they include their differentiator:

What differentiates Wirecutter from other review sites is the rigor of our review process, the transparency we provide to our readers about that process, and our reader-centric, useful approach to recommendations.

Sharp-eyed readers will see that these values line up nicely with my points above, just in a different order: authority, transparency, respect, and utility.

You’ll have to trust me that I wrote the outline for this post months ago. For my part, it tickles me pink that this post so directly aligns with their editorial team’s thoughts.


* The Wirecutter actually makes money on anything you buy at an affiliate’s site for a certain amount of time. In the case of Amazon, I think it’s the next 24 hours. 

Images are screenshots of TheWirecutter and The Sweethome.