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Honest operator notes on building, leading & life. 36 and counting.

AI · Trust · #ChipChats

The Gap Is Closing. It Can't Touch the Part That Matters.

I write these with AI — a neurological condition took my typing, and AI gave my output back. The cost of sounding competent has collapsed, even at the top of the ladder. When everyone can produce a sharp answer, the answer stops being the differentiator. What's left is older and simpler: trust, presence, judgment — the one layer no model can reproduce.

July 16, 2026
Perspective · Gratitude · #ChipChats

The Earth Kills Us by Accident.

A fault line has no god. A wildfire has no flag. Nature erases us without malice — Pompeii, Tanis, the next asteroid. Then I read the rest of the news: wars that won't stop, borders drawn in someone else's blood. That part we choose. Perspective isn't detachment — it's caring about the right things, harder, while we still can.

July 13, 2026
Gratitude · Perspective · #ChipChats

I Was Born in America. I Didn't Do a Thing to Earn It.

A UN headline put a number on the other side of the birth lottery: roughly a quarter of a billion people need urgent humanitarian help right now. Same kind of parent, same hopes for their kids — just a different line on a map. Most of my comfort is luck. The least I can do is not waste it being ungrateful.

July 8, 2026
Leadership · Space · #GetCentered

The Most Complex Thing We Ever Built, We Built Together.

Watching Jared Isaacman on Face the Nation brought it rushing back — the ISS, the most complicated machine humans have ever built. It didn't have to be international. In 1993, Dan Goldin invited a forty-year rival in, and that choice saved it. If we could do that up there, don't let anyone tell you what we can't do down here.

July 5, 2026
Founder Life · Perspective · #ChipChats

I Gave Four Years to a Deal That Fell Apart in an Afternoon.

Twelve months at the table, down to minor redlines — and then it was over. For a while it felt wasted. But that collapse is the only reason we pivoted, and the pivot became a three-way international merger: the proudest deal of my career. The failure didn't cost me the win. It was the door to it.

July 3, 2026
Gratitude · Perspective · #ChipChats

I'm Celebrating an Unfinished Country.

A documentary on the birth of America, watched from Boston. The founding wasn't clean — the best of us and the worst of us have always lived in the same body. I'm not celebrating a finished country this Fourth. I'm celebrating an unfinished one, and the people on the road who are the whole point.

July 2, 2026
Partnership · Entrepreneurship · #ChipChats

Two Kids. One Dinner. No Idea What Was Coming.

A photo in my friends' Boston office. Eighteen years ago Seth Burr and Darrin Lang bet on each other and started LABUR — their two last names stitched together, no daylight between them. I've watched founders chase the exit. These two chased the work. Different game.

July 1, 2026
Mental Health · Legacy · #ChipChats

What Do You Regret?

One of twelve questions in Rabbi Steve Leder's For You When I Am Gone. Your regrets aren't a confession of failure — they're a roadmap of what you learned. Don't wait for a deathbed to answer the hard questions.

June 13, 2026
Founder Life · Leadership · #ChipChats

Four Startups. All Four Exited.

Combined enterprise value north of $100 million. I could stop there and let it sound clean. It was not clean. Across all of it, the throughline was never the outcome. It was the people.

June 12, 2026
Perspective · Stoicism · #ChipChats

You Are a Crew. Be a Good One While You Can.

What do a Tuscan vintner, the crew of Artemis II, and Marcus Aurelius have in common? They tell the same story. From that far out, you cannot see a single border — just one blue thing holding everyone.

June 10, 2026
Risk Management · Leadership · #GetCentered

I See Risk Before I See Anything Else.

Blame law school. Two cases from first-year Torts never left me. One taught me to price the downside. The other, that I only own the risks I can foresee. Different leaders, different chapters — every one of them taught me the same throughline.

June 2, 2026
Perspective · Gratitude · #ChipChats

Completely Unrelated Things, All Pointing Me the Same Direction.

A space stat and a 2002 movie. Both dragged me back to something I wrote last year. There are eight billion of us on one planet. The only things that have ever felt big up close are the people and the moments.

June 1, 2026
Gratitude · Perspective · #ChipChats

I'm Embarrassed by It.

Within the last few days, I've said "Happy Memorial Day" and "enjoy the long weekend." The day very obviously isn't about a three-day weekend. It's about people who didn't come home, and families who've carried that weight ever since.

May 25, 2026
Founder Life · Perspective · #ChipChats

The Moment Isn’t Coming. This Is Everything.

We sold our company eighteen months ago — after twelve years of building it from nothing. I waited for the moment that was supposed to come after. It didn't. Marcus Aurelius. Brunelleschi. Michelangelo. Every one of them is dead.

May 26, 2026
Leadership · Stoicism · #ChipChats

2am in Rome and I’m Thinking About Marcus Aurelius.

Stood in front of him today. The most powerful man in the known world. What survived him is a journal he never meant anyone to read. Performed strength ages badly. Honest reflection compounds.

May 19, 2026
Team · Gratitude · #GetCentered

Some Appreciation That’s Long Overdue.

Kay Cameron was the third person in the office at ATIS. David Estes helped us scale ATIS too. You don't build multiple businesses with the same people unless those people are the reason it worked the first time.

May 19, 2026
Board · Employee Ownership · #ChipChats

Honored to Join the Board of Ascend Safety Collective.

Vertical transportation is one of those quiet industries where safety, compliance, and service legacy compound over decades. What drew me in: the commitment to broad-based equity for the Team.

May 19, 2026
Family · MESH · #ChipChats

What If Kids Learned Early That Bravery Isn’t the Absence of Fear?

When Dustin Hejna and I started talking about Friendever, the thing that kept pulling us in wasn't the product roadmap. Turns out the version of "brave" we picked up as kids isn't bravery. It's armor. And armor gets heavy.

May 12, 2026
Leadership · Accountability · #ChipChats

Good People Have Sunk Companies with Good Intentions.

Not bad actors. Not lazy ones. People who genuinely meant well and told themselves the right story. A culture of accountability isn't harsh — it's clarifying. We talk about what happened, not what we meant to happen.

May 12, 2026
Leadership · Psychological Safety · #ChipChats

Gossip Is a Mirror.

One of the most revealing moments in any room is the moment someone leaves it. What gets said in the next sixty seconds tells you everything — not about the person who walked out, but about the people still sitting there.

May 12, 2026
Private Credit · Advisory · #GetCentered

Two Camps on Private Credit. Ignore Both.

The private credit conversation has split into two camps and middle-market operators should ignore both of them. Neither framing helps the operators weighing whether to sell, recapitalize, or refinance into the next cycle.

May 12, 2026
Leadership · Vulnerability · #ChipChats

She Cried at the Press Conference.

She wasn't falling apart. She was feeling the weight of what she was doing — standing between vulnerable people and the thing that hurt them — and her humanity showed through. Guilty on 17 counts. Proud husband.

April 12, 2026
Mental Health · Loss · #ChipChats

This One Is Different.

A man I know just ended his life. We weren't close. Never met in person. But we wrote chapters in the same book. His was called "Strength Through Surrender." I can't stop thinking about that title. We cannot keep losing people to silence.

April 11, 2026
Perspective · NASA · #ChipChats

It’s 3:30am and I Can’t Sleep…Again.

This is my NASA badge from the Dan Goldin era. I was 22 years old and had absolutely no business being in that building. Yesterday, four astronauts flew farther from Earth than any human in history. Victor Glover said it simply: seeing Earth from that distance is a reminder of humanity's shared identity.

April 7, 2026
Spirituality · Faith · #ChipChats

I Wear a Cross and a Crucifix. I Also Think I’m an Atheist.

Make of that what you will. The crucifix belonged to a great friend who gave it to me because he thought I needed to find Jesus. Neither makes me Christian — they make me someone who understands that symbols mean what we need them to mean.

April 2026
Perspective · Grief · #ChipChats

Death. What a Shitty Topic.

I think about it often. It started in eighth grade when I lost my first grandparent. Bad memory in general — but I can vividly recall the circumstances around that evening and every single loss since.

March 30, 2026
AI · Advisory · #GetCentered

The Knowledge Gap Is Closing. Here’s What That Means for Your Advisory Team.

For decades, professional services solved complexity through specialization. AI is changing that equation — and we built Centered Partners around what comes next.

April 2026
AI · Advisory · #GetCentered

Everyone Is Talking About AI Replacing Experts. They’re Asking the Wrong Question.

The real problem in professional services was never a shortage of expertise. It was a shortage of connection between it. Here's what AI actually does — and what it doesn't.

April 2026
Sobriety · Mental Health · #ChipChats

Everyone Has Skeletons. Everyone.

I'm writing a book. My Skeletons Are Better Than Yours. The real point isn't competition — it's that we're all dragging something around and burning enormous energy keeping the closet door shut.

March 29, 2026
Mental Health · Noise · #ChipChats

The World Appears to Be on Fire

Wars. Elections. AI. Emotional entropy. And yet — my calendar remains full. I am personally struggling with the scale of what's happening out there and the smallness of what we're asked to care about in here.

March 2026
AI · Founder Life · #ChipChats

What Focal Dystonia Taught Me About AI

Writing was once one of my greatest strengths. AI cleared away the friction between having an idea and executing it — and gave me back the most valuable thing any of us have: time.

February 2026
Marriage · Gratitude · #ChipChats

Next Time Corporate Feels Heavy

My wife has been an assistant prosecuting attorney for 18+ years. She handles the cases most attorneys wouldn't want to touch. She carries weight that doesn't clock out.

February 2026
Founder Story · ATIS · #ChipChats

Some Things Really Do Get Believed Into Existence

My dad, brother, and I started ATIS from scratch in late 2012. I will never forget sitting in my basement and filing the articles of organization. A vision. Weekly Sunday morning visits on my parents' porch.

January 2026
Centered Partners · Founder Story · #ChipChats

The Opportunity I Couldn’t Ignore

Smart people. Real businesses. Real risk. Being served by advisors too narrow, too transactional, too focused on their own product shelf. That's the gap Centered Partners was built to fill.

March 2026
Centered Partners · #ChipChats

He Fiddled. I’m Scheduling Zooms.

Someone in the comments said it perfectly. "That's what Nero said." The answer to the noise isn't paralysis. It's building things worth building — and making sure the people around you are better off for having worked with you.

March 2026
Family · Music · #ChipChats

My brother wrote a song called Heaven to Me.

Austin Grimm is a St. Louis-based musician — former frontman of Roots of a Rebellion. He's also my brother. And somewhere in his journey he wrote a song that stopped me cold.

March 2026