Schlep

Hello {{first_name|dear builder}}! Happy Sunday and Happy March.

In an interview with Ezra Klein last week, Anthropic co-founder Jack Clark said “Often the impediment [to the AI taking on more labor from humans] is organizational schlep rather than any limiter in the system.” It made me grin - I hadn’t heard those two words put together before¹, and schlep was an unexpected word delivered from the voice of a Brit living in San Francisco. I wonder where that word entered YOUR training data, Mr. Clark.

Schlep is a Yiddish word, from the German slepen - to slip or drag. Think of harried downtrodden Eastern European Jews dragging their bags.

I happened to be listening to this podcast while walking out of the Denver airport on Wednesday evening, having just returned from a two-day onsite with our new client: the Dallas Jewish Community Center. Organizational schlep landed in my ears as exactly the right way to describe so much of what I had seen and heard from this team, who told us about the extensive manual labor involved in managing their technology.

There is someone whose whole job is to do the billing manually for a registration system that doesn’t talk to their Salesforce. There are still workaround spreadsheets and even paper forms because the team didn’t know there is a feature they could flip on in their Salesforce that could do that for them. There are four different people who have to be consulted every time a new registration form is made, and those conversations happen in a series of emails back and forth.

Schlep city.

But schlep doesn’t just sprout randomly - it has roots, and understanding those roots is part of our method at OpenTent for figuring out where to take our clients next. I asked the leadership team:

How did we get here?

Salesforce isn’t working for us. It’s a mess.

Why?

When we implemented Salesforce we tried to cut costs. We spent only the bare minimum. We didn’t fully invest the way we needed to.

Why?

IT reports to the CFO.

What?

So does HR.

Why???

20 years ago our organization was nearly insolvent. We had to create a culture that monitored and controlled costs rigorously. We’re still living inside that culture even though now we are in a much more healthy financial place.

Ah. The bag this team is schlepping has roots in an organizational trauma from two decades ago.

Back in my hotel room after dinner with the client team, I had a couple open hours before falling asleep. What to do with this toddler-free alone time?

I fired up Claude Code, of course. I got to work on my “better software for synagogues” idea. I asked Claude to make an implementation plan, and then we workshopped it. I asked: What are you missing? How can you make this simpler? What would an experienced CRM architect say about it? Or a software security researcher? What would make them use it every day? Why would people not want to use this?

We ended the evening with a brilliant and detailed planning document. Another astonishing AI agent experience that made my head spin with the implications.²

In the morning I went back to the JCC, and the contrast in schlep factors was surreal. Listening to staff describe how they work now, I couldn’t help but think (to myself): the agents will just devour this.

Except they can’t. Not yet. Not for lack of interest - the new CEO of the JCC told me his appetite is “voracious” for using AI to help them work more efficiently. But first there is the organizational schlep to contend with: culture, habits, trauma, personalities, the context held inside individual brains for decades.

This is why AI headlines feel like a split screen these days — impending society-level transformation on one side, “95% of AI implementations fail” on the other. Over two days in Dallas, going from agents to organizational schlep and back, I felt like I could see both sides of that split screen. They are both uncomfortably real.

After our last meeting, I had just enough time before my flight for some additional client context gathering: working out at the fitness center. It was warm and cozy like you’d hope for from your local community center. In the locker room a very old and very naked man gave me the meanest stare I’ve ever received when I inadvertently put my backpack in front of his locker.

I’d take this quirky humanness over a cold fancy Equinox any day of the week.

Refreshed, I packed my stuff and walked out of the building. The sun was a pink setting hum in the warm air.

I was lost in thought until my eyes landed on a stone memorial that startled me to a stop.

After a day of spreadsheets, dashboards, metrics, budget lines, my head was full of numbers. And then here were numbers of a whole different emotion, engraved in stone. I felt a lump in my throat.

Those harried downtrodden Eastern European Jews. Schlepping their stuff and speaking their Yiddish until their stuff and their Yiddish were taken and destroyed.

If they were still here, how many more members would the JCC now have?

How did we get here?

How did I get here?

The answer felt as solid as the memorial stone:

I am here to help communities I care about free themselves from schlep work.

Less dragging. More joy. Less slipping. More relationships.

Now is the time.

This observation is an extremely deep cut, understanding that zmanim are the holiday beginning/end times and that Conservative/Reform communities might not care about this as much. Made my jaw drop to see it.