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.)

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.