'Here goes. Day One.'
Something I wrote about the founder of Scary Mommy.
I don’t know where this newsletter fits in Elisabeth Kübler-Ross and all that. But there should be a stage of grief when:
You want to mourn someone, but you also don’t want to position yourself as the main character in their story.
You don’t want to imply that you were closer than you actually were because it’s now opportune—or even pretend you never had disagreements and saw everything eye-to-eye, because you didn’t.
But you still mourn them and pray for them.
That’s this post. Exhibit B-for-Bill.
It’s about Jill Smokler. If you never met her, you missed out. She died recently at age 48.
Of all the things, I am extremely annoyed that she did not make it to 50.
The first time I remember talking to Jill was in 2014 on speakerphone in a tiny conference room in the Chelsea section of Manhattan. We were trying to get her to write for our new digital media startup — and hopefully bring her popularity, her reach, maybe some of the people she worked with.
Long story short, we wound up buying her entire company, instead: Scary Mommy.
She came aboard, and brought her whole crew, and together we expanded, hired more people, saw massive reach, brought others …
Here’s how I remember Jill:
Smart, funny, driven, kind, acerbic, confident, vulnerable, talented, worried, proud, insecure, skeptical, second-guessing.
I think part of her really enjoyed that she was able to keep her life and her family in Baltimore and come up to New York City all the time to run her part of the combined company.
I think another part of her was wistful about what might have happened if she had never sold, and kept control of the entire Scary Mommy empire.
She was not the first entrepreneur to wonder about that choice. I’m confident we did right by her and built something pretty great. But again, I’m trying not to be the main character here.
Maybe if she could have just pressed rewind on the great Gen X VCR of life …
Who among us hasn’t wished for that once in a while?
First off all, there is no rewind.
Second, on the big thing — glioblastoma — it seems it would not have helped.
Jill would have hated that I am now quoting an AI summary to put this in context … but here’s the context:
Glioblastoma is an aggressive form of brain cancer. While early detection allows for faster intervention and extends life, it is generally considered incurable.
Median survival is 12 to 18 months, though aggressive treatments allow about 5% to 7% of patients to live five years or more.
Anyway, that’s what she had, and it killed her.
She leaves behind three children who were the love of her life — the real, honest kind of love, which Scary Mommy made clear: the kind of love you can feel while also being “super-human,” but not “superhuman,” and wondering at times what the heck you got yourself into.
Jill carried a lot of other stuff, too.
I’m not going to put it all in an obituary-style post, especially because some of it quite literally wound up in People magazine.
Just remember: “Everyone you meet is fighting a battle you know nothing about.”
Anyway, back to making this all about me.
I am glad to be able to say that I did a bit of the work and tried to keep in touch with Jill after our Some Spider/Scary Mommy days. Fun one —
Fri, Aug 17, 2018: “Hi Jill, How’s it going? How’s retirement? Have you moved to Florida and become a Republican yet?”
(Narrator: Bill knew it was HIGHLY unlikely she was ever going to become a Republican.)
We had a few Zoom calls over the next few years, the last of which was in June 2023. That was a year before she was diagnosed.
Again, I don’t mean to suggest that Jill and I were close. We were colleagues, and I enjoyed working with her. She was a good person and an inspiring entrepreneur.
She affected my life, and I am very happy with how my life has turned out — and how I hope it will keep turning out.
And, every once in a while, I see a post where someone is mourning a friend or a colleague.
They do a nice job, and at the end I think: I know the writer, not the friend — but if the friend inspired someone to write that kind of post about them, then they must have been a remarkable person.
Sometimes it inspires me to Google that remarkable person and learn more about them, even if we never met in real life.
Here’s your search link: jill smokler
That’s this post. Exhibit J-for-Jill.
Other things worth knowing …
NYT: A federal judge ruled Monday that President Trump’s lawsuit against the IRS was an improper exercise in self-dealing and barred him from claiming that the extraordinary tax protections he received were part of a legitimate settlement agreement. In a 56-page order, U.S. Judge Kathleen M. Williams also referred the lawyer who brought Trump’s case to the Florida bar for potential disciplinary proceedings.
AP: An Immigration and Customs Enforcement agent fatally shot a motorist in Maine on Monday — the second time in a week that ICE has used deadly force and at least the ninth death since 2025. ICE said in a post on X that “fearing for public safety, an officer discharged his weapon.”
Politico: FBI agents grilled deceased Sen. Lindsey Graham’s neighbors Monday about what they saw the night he died, as speculation swirled following his recent visit to Kyiv and his criticism of the Iran war. Separately, Graham’s younger sister Darline Graham Nordone will serve the remainder of his term in Washington.
The Guardian: Meet the New York nurses replaced by AI: “It should concern every patient who cares about quality of care.”
CNBC: These are America’s 10 worst states to live in for 2026. Crime rates, air quality, healthcare access, worker protections, and civil rights laws are among the factors that can hurt a state in quality of life rankings.
NYT: The federal government has approved plans by a startup to test a satellite that would use a 60-foot mirror to reflect sunlight back to Earth after dark, to power solar farms, provide light for rescue workers, and illuminate city streets. The company plans to deploy its test satellite this year and eventually wants to send as many as 50,000 mirrors into space.
Fast Company: Play-Doh’s first set for adults is peak “kidulting”: Blooms by Play-Doh gives your favorite childhood toy an adult-centric glow-up.
Thanks for reading. I wrote about Jill at Inc.com. See you in the comments.