How Meetings Got Cheap & What That Cost Us

There was a time when calling a meeting was an act of accountability.

You had to book a room, you had to get people to physically show up, and you had to have something worth saying, because if you didn’t, everyone in that room knew it. The friction wasn’t a bug. It was a filter.

Then Zoom happened.

This isn’t a critique of Zoom. It’s an observation about what zero-cost anything does to human behavior. When meetings became free to call, people called more of them. “Let’s jump on a quick call” replaced thinking the problem through. The default answer to ambiguity became a calendar invite.

Calendly finished the job. Suddenly you didn’t even need a conversation to schedule a conversation. Two strangers, on camera, 48 hours from now, no agenda, no context, no real idea why either of them is there.

COVID made all of this feel like it was working. Everyone was at a desk, everyone was available, and the assumptions the system was making briefly held (that you’d be present, that you’d be focused, that the call was the most important thing happening).

Then the world opened back up, and the system quietly broke.

People started taking calls while walking to lunch, while driving, while doing something else entirely. We've all felt that mismatch when you've set up properly for a Zoom meeting and the other person joins from the car. If they'd just said 'I'll call you then,' it would have been fine. It is Calendly-enabled scheduling mayhem. Then the phone call made a quiet comeback, not as an upgrade but as a concession. If nobody is going to be present anyway, at least the phone doesn’t pretend otherwise.

For a long time, my meeting volume was my KPI. Not formally, not written down anywhere, but if you’d watched how I operated, you’d have seen it. A full calendar felt like signal. It meant I was connected, relevant, in the flow. In venture especially the logic seemed defensible: the network is the asset, keeping relationships warm is the work, and the only way to keep relationships warm is to show up. So I showed up. Constantly.

I built a homemade CRM in Airtable to track all of it. Every meeting logged: the person, the category, the date, notes. Portfolio. LP. New investment. Recruiting. Network. Admin. There was a small dopamine hit every time I added a row. A record of effort. Proof that I was doing the thing.

I would come back from a New York trip and announce, with genuine pride, that “I did 30 meetings in 4.5 days… and one of the days was a Sunday.” I said it like I’d won something.

Then a friend and coach, David Rust, suggested I add one more column to the tracker. Was the meeting energizing or draining? Regardless of the category, time of day, or mood, I would meditate for the five seconds after each meeting and record how I actually felt. Then at the end of the week I could ask myself which of the non-energizing meetings had actually been accretive.

It was a small ask. One additional field. But it changed everything about what the data was telling me.

When I went back and started tagging, the pattern was uncomfortable. A lot of the meetings I’d been proudest of, the high-volume days, the packed NY trips, the Sunday calls, were draining. Not all of them. Some were genuinely generative. But the volume I’d been optimizing for had almost nothing to do with the quality I actually cared about. The category cut made it worse. Portfolio time was almost always energizing. Some of the network sprawl was not. I had been celebrating the average and ignoring the mix.

The truth is that wanting to actually show up focused to that many meetings is exhausting, and something has to give, either the focus or the volume. Portfolio and LPs are always number one, and everything else is in service to that. So I started using my junior investor to deflect new investment screening meetings and pushed admin to other members of the team.

I had built a system to measure quality and then used it to celebrate quantity. The metric had eaten the goal.

I looked up from the spreadsheet and asked myself what I’d actually moved forward that week in New York. No revelations to share. No notable quotes. Just a bunch of nice conversations.

This is the textbook pseudo-productivity trap. Cal Newport named it in Slow Productivity: the substitution of visible activity for actual output. Meetings are the purest form of it for deal-driven knowledge work. They look like work, they feel like work, they get scheduled, attended, and recapped like work. Most of the time, they are not work.

And here’s what changed once I started cutting. The meetings that survived the filter got noticeably better. More engaging with LPs, more empathetic with founders. The connectivity between those two groups is fundamentally my job and how I accomplish long-term goals, and protecting the energy for them turned out to matter more than I’d realized. The fewer rooms I was in, the more present I was in each one.

The deeper problem isn’t that meetings got easier. It’s that we never added the real accountability back.

Meetings used to require agendas because they were expensive. When they got cheap, we skipped the agendas but kept the meetings. We got the worst of both worlds: the volume of frictionless scheduling with none of the preparation that friction used to force.

This hits relationship businesses hardest. Venture, sales, recruiting, business development, fundraising. These are industries where the entire model depends on the quality of human contact, on whether someone trusts you, believes in you, wants to work with you. And quality and quantity in relationship work aren’t really in tension, they’re incompatible. Every low-quality meeting crowds out a high-quality one, not just in time but in attention and energy. You can’t give someone your best in the seventh call of a day when you didn’t need to be in the first six.

Peter Drucker said “what gets measured gets managed.” It’s usually quoted approvingly. But there’s a harder version of that idea that nobody says out loud: what’s easy to measure gets measured first. So be careful what you make easy to measure.

Meeting count is easy to measure. Dopamine-hit easy. Row-in-a-spreadsheet easy. The quality of what happened in the meeting, whether it moved something forward, whether it was worth both people’s time, whether it left you more capable or less, that’s harder to quantify. So it gets measured less. And what gets measured less gets managed less. Enter AI-powered meeting note takers and the engagement floor drops to zero. You don’t even have to think in real time and process what’s going on, the AI will catch it in the notes. While facts like metrics and names are great for AI to capture, the important thing is to think and engage, and it’s just too easy to slip into not paying real attention when you have that crutch.

The energizing/draining column was the forcing function I needed. It made the harder thing slightly easier to measure. Once I could see it, I couldn’t unsee it.

One of my rabbis taught me what intentional friction actually looks like in practice. He spends his days dealing with some of the hardest problems in the broader Jewish community, and his time is, by any reasonable measure, scarce. So how does he filter? Before he will meet with you, you have to send him a typed fax laying out the full detail of what you’re dealing with.

A typed fax. In 2026.

It is, on purpose, an absurd level of friction. And it is an excellent filter. If your problem isn’t worth the effort of writing it out and finding a fax machine, it probably isn’t worth his time either. And if it is worth his time, the act of writing it out has already done half the thinking for you. By the time you’re in the room, you’re not flailing around trying to articulate the problem, you’re presenting it. The meeting starts at minute one rather than minute twenty.

That is what friction is supposed to do. It isn’t an obstacle. It’s a forcing function for clarity.

But not all friction is created equal, and this is where I think a lot of people get it wrong. Making someone prepare before a meeting is productive friction. Making someone wait six weeks for a meeting is not. Delay isn't a filter, it's just delay. It feels disciplined because it feels hard, but all you're doing is moving the same unfiltered conversation further into the future.

Which brings me to a rule I’ve made for myself that some people find strange. I don’t book meetings more than two weeks out, except in genuinely special cases.

Why? Because the cancel and reschedule rate on anything booked further than two weeks out is something like 80 to 90 percent. So why bother? You’re not actually scheduling a meeting, you’re scheduling the idea of a meeting, and ideas of meetings have a remarkable habit of dissolving when the actual day arrives and reality has moved on.

The deeper issue is what booking far out reveals about how people are organizing their time. Pushing something out three or four weeks doesn’t help you prioritize, it lets you avoid prioritizing. It’s the calendar equivalent of “I’ll deal with that later,” and later almost never comes in the form you imagined when you booked it. The future-you who was supposed to take that meeting was always a fiction. By the time the day shows up, that person has their own problems.

A two-week horizon forces honesty. If something matters, it can happen in the next two weeks. If it can’t happen in the next two weeks, the question isn’t really when, it’s if it will happen.

There’s nothing wrong with putting a quarterly placeholder on the calendar, just call it what it actually is. A placeholder is not a meeting. It’s a hope that you and someone else will both still want to talk in three months. Sometimes you will. Often you won’t. Either way, the real decision about whether to meet gets made the week of, not the day you put it on the calendar. Pretending otherwise is how calendars fill up with phantom commitments.

Just yesterday, a young rabbi who works with university students in London reached out. He has students who are interested in finance and also growing in their Judaism, and he asked if I’d be open to sharing my number with a few of them.

I said no. But here is what I offered instead:

I have a personal website with articles and interviews. I have a podcast, including an episode specifically about career advice. Start there. Read what’s already written, listen to what’s already recorded, and if after that you have a specific question, I’m happy to talk.

That isn’t a brush-off. It’s the same idea as the fax. If a student isn’t curious enough to spend an hour reading and listening before reaching out, they’re probably not going to get much out of a fifteen-minute call where I repeat what’s already in those resources. And if they do put in the time, the conversation we end up having is dramatically better. They show up with a real question. We start at minute one.

The default mode of “share your number, take the call, be generous,” sounds generous and is actually the opposite. It optimizes for the appearance of access. It doesn’t optimize for the student actually getting helped.

The friction is the help.

My KPI now is the inverse of what it used to be. The goal is the fewest meetings possible.

More presence. Higher impact. Genuine productivity.

Not because the network doesn’t matter. It does, genuinely, and keeping relationships warm has real value. But everything has a cost, and pretending otherwise doesn’t make the thing more valuable, it just makes you blind to the tradeoff. Every meeting I take now is a conscious decision, not a default. That standard changes how I prepare, it changes how I show up, and it changes what happens in the room.

The friction was never the problem. It was a feature all along.

We spent years eliminating it, congratulating ourselves on efficiency, and ended up with calendars full of conversations we’re not quite in, about problems we haven’t quite defined, with people we haven’t quite prepared to meet.

Bring back the cost. Make meetings expensive again, not in dollars, but in the standard you hold them to. Ask what this meeting is for before you schedule it. Ask whether an email would do. Ask whether you’d be comfortable defending the agenda if someone asked.

The best meetings I’ve ever been in had one thing in common: everyone in the room had already done their thinking before they got there.

That’s not a technology problem. It’s a discipline problem. And it’s entirely solvable.

Hat tip to David Rust for the energizing/draining column and the category split. One of the simplest and most clarifying additions I’ve made to how I work.

Share