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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.)

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