Jay Olivo Letters for people building on a second shift Apply

The Second Shift

You are not the only one who got handed the keys.

The Second Shift is a small room. Eight people who are making the same change you are: from being good at the work to leading it. We meet twice a month for ninety minutes on video. You bring what you're stuck on. You leave with something to try.

No lectures. No slide deck. Just eight people who understand your Tuesday.

See what it costs

What the room is

The Second Shift is not a course. There is nothing to finish, nothing to fall behind on, and no certificate at the end.

It's not a warm up for something later. Nobody is going to walk you to the back of the room and sell you the real thing. This is the real thing.

It is a room. You bring the work you're actually doing, in the shape it's actually in. You put it in front of people whose weeks look like yours. Then you get something back.

Something back means an answer, or a better question, or somebody pointing at the part of your plan that does not hold up. It does not mean applause. Applause is free everywhere else on the internet.

The Letter is where you read me. The room is where I read you.

Here's the kind of exchange I mean. People called me stubborn for years and I stopped arguing about it. Then somebody in a room called me hardheaded. A guy I worked with named John Rashi looked at me and said I don't have a hard head, I have strong beliefs. He didn't solve anything for me. He handed the same thing back in words I could use.

How it works

Eight seats, and that's the whole room. Small enough that you talk every single time. Small enough that I remember what you were working on last month.

Twice a month, ninety minutes, on video. First Tuesday and third Thursday, 7 p.m. Eastern. Put it on the calendar once and you're done. Join from your kitchen table.

One real problem a session. Somebody brings the thing they're carrying. We work it. Then I hand over the tool that fits it, not the one I happen to be selling, because I'm not selling one.

What's said in the room stays in the room. You will be talking about people you work with. That only works if nobody repeats it.

Who it is for

One filter, and it's not a personality type. People with real obligations who are building something anyway.

It is built for operators and owners. Your week already belongs to something. You are building anyway, at night, on weekends, in the hour before everybody else gets up.

This room is for you if

  • Your week is already full. A job, a business, a family, or all three at once.
  • You are still putting money and evenings into something real. Stocks, property, a side company, a book, a skill.
  • You will bring the actual thing, not the tidy version you tell people at parties.
  • You would rather be told the truth than be cheered up.

This room is not for you if

  • You want a plan you can follow without changing your week. Nothing here works if your calendar stays exactly the same.
  • You are looking for customers. Do not apply if the plan is to sell to the other people in the room.
  • You need this to pay for itself by a certain date. Then do not spend the money. Nobody here is promising you that.
  • You want to watch quietly. Reading is welcome and reading is free. The room is for people who will say the thing out loud.
  • You can't say what you're building in one sentence yet. Come back when you can. That is a timing problem, not a knock on you.

If you read that second list and felt let off the hook, that is the list doing its job.

Three tiers, one room

The Letter
Free and open to anyone. One letter a week. Give an email address and it shows up. Leave whenever you want.
The Second Shift
The paid room, and the one this page is about. You apply to get in. The price is published below.
The Table
The Table exists. It is 8 to 12 peers, and the invitation comes from inside the circle. Everyone at it signs a twelve month written commitment, and I sign the same one every member does. You cannot apply to it.

What it costs

Annual only. There is no monthly option.

The first eight members are founding members, and founding members keep $600 for as long as they stay. After the founding seats are gone the price is $1,200. You will never open a renewal letter with a bigger number in it.

Founding rate, year one $600 for year one

For the first eight members.

Standard rate $1,200 a year

What the room costs after that.

Why the founding rate is lower. You would be joining a room with no track record yet. There are no results to show you, because there are none to show. That is a real risk you would be taking on, and the price should say so out loud.

Where the money goes. Every dollar goes to Leadership TeamBuilder, the 501(c)(3) I founded in 2017. I donate my time.

The price is published here so you never have to ask anyone for it.

What happens when you apply

Applying is not paying. There is no card on the application, and sending one costs you nothing.

There's an application. It takes about ten minutes, and it's real questions, not a form with your name and your title on it. I read every one myself.

I'm looking for people who are in the job right now and want to be better at it. If you're looking for a class, a certificate, or somebody to agree with you, this is the wrong room and I'll tell you so kindly.

  1. You answer eight questions about you, your week, what you are building, and how much time you honestly have for it. Short answers are fine.
  2. It comes to me.
  3. You get an email saying your answers arrived. After that they sit with me until I go through them. Money comes after that, never before it.

Not everyone who applies gets in. That's a normal outcome and it's not a verdict on you.

Apply to The Second Shift

Not ready to apply

Then read first. The letter comes once a week and it's free. If you read it for a few months and never apply, that's a fine outcome.

You will get one email asking you to confirm. That is it. No spam, and every letter has an unsubscribe link at the bottom.