Billion Dollar CEO Time System [BDL #2]

The unspoken rituals of the best operators in the world

Jul 30, 2025

Most billion-dollar operators never ask, "What should I do today?"

They already know the answer. They designed their tomorrow last night.

I learned this watching my Dad, a pure-bred entrepreneur. Every night after dinner, he’d perform the same ritual: Kitchen table… Leather-bound notebook… Meticulously planning the next day.
"Creating tomorrow today," he called it.

At Goldman Sachs, they taught us that markets reward predictability.

The same principle applies to your personal operating system. When your team knows you'll deliver what you commit to, when you know your own capacity, when Friday doesn't become a frantic overflow day… that's when real leverage begins.

Here's what I learned across 5 exits and 20 years: Stress isn't a scheduling problem. It's a design problem.

If you wake up asking "What should I do today?" you've already lost. You don't have a time problem… you have a design problem.

Here’s the system to fix it.

BTW, this is lesson #2 in the BDL series.

The Billion Dollar Lessons (BDL) series is where I share one timeless lesson at a time, each one organized into a clear framework, drawn from building two billion-dollar companies and investing in over 100+ businesses. This is what I wish I had when I didn’t have the playbook, and more importantly, what I hope my children will read one day. So I hope it helps you, and I hope it makes them proud.

The Sprint System: My Billion-Dollar Time Design

When we were scaling Real from 6,800 to 26,000 agents in 24 months, I started thinking in two-week containers, exactly like a software development team. Each sprint had defined projects, clear outcomes, and non-negotiable boundaries.

It was my personal operating system.

You have to do something that other people won’t do, if you want to have what other people don’t have… right?!

This is how you move from being reactive to being insanely focused and useful.

Framework #1: Run Your Life in Sprints

I run my entire life in two-week sprints.

Each sprint has a defined set of projects and goals. If a new request or idea comes up, the answer isn't a stressful "yes" or a guilty "no."

The answer is: "Next sprint."

When you live in sprints, requests for your time become simple.

Someone wants a meeting? Next sprint.
A client needs a proposal? Next sprint.
A partner needs complex documentation? Next sprint.

Real example: A family office partner needed offshore trust documentation. He asked when he'd have it. I said, "October 15th." He was shocked and asked how I could give him that exact date. I told him: "That's when my sprint ends."

At Teles, when we needed $8.3M in daily sales to scale from $300M to $3.4B, we didn't have motivational meetings about "doing our best." We reverse-engineered the exact activities required per sprint and made them non-negotiable.

Predictability creates scale.

Framework #2: The Buffer Principle (The 80% Rule)

A few years ago, I got sick.

It kinda sucked.

Doctor appointments were impossible to schedule because my calendar was packed wall-to-wall. In desperation, I told my assistant to block out all of my Fridays. Permanently, until I was healed.

After I recovered, I kept Fridays blocked. It was the best decision I ever made.

Friday became my buffer day. No meetings. Just strategic space for deep work, creative thinking, and critical catch-up projects.

That’s when I gave this concept a name… “80% equals 100%” because we only schedule 80% of the week. That 20% buffer is everything.

The data backs this up. At Real, we found that agents who religiously protected their buffer days outperformed the constantly-available, reactive agents by a staggering 3-to-1 margin.

Just to be clear: Buffer isn't rest. Buffer is strategic capacity. It’s not to chill out. It’s to work you face off… without being interrupted. It’s when you are insanely excited to work all day.

Without it, your weekends become overflow parking for the week's stress. Monday feels like punishment instead of possibility.

Framework #3: The Friday Review + Preview

My coach Michael Sheargold taught me this and it has become my non-negotiable Friday ritual. It takes 10-15 minutes and fundamentally changes how I enter the weekend and attack the week ahead.

Friday evening, before I shut down, I look back one week and forward two weeks.

Review (1 Week Back): I go through every single meeting and task on my calendar from the past week. I write down every follow-up. I close every open loop. Nothing slips through the cracks.
Preview (2 Weeks Forward): I scan my calendar for the next two weeks. What do I need to prepare for? Are there any trips, major deadlines, or critical deliverables coming up?

This simple habit eliminates the "Sunday Scaries" and replaces them with Monday momentum. Sorry, I am in an alliterative mood today. My assistant does it too, so she stays ahead of me instead of reacting to me.

Framework #4: The Adult All-Nighter

If you would like the single biggest productivity hack, here it is:

I pick one day every other week (generally Thursdays)
And I tell myself, “I am not going to bed until __________”

It maybe writing a detailed memo, or creating a new pricing strategy, or switching to a new CRM, or researching a new plane to buy (which I just did last week)… it is an ultra-focused time to do one deep and impactful project.

Even my wife knows the drill.

She'll ask, "Is it your Thursday?" If I say yes, she says, "Okay, I'll talk to you in the morning." Then I put on my headphones and work until the single most important thing for that sprint is done.

This builds something more valuable than productivity: self-trust.

When you consistently keep the promises you make to yourself, you develop unshakable confidence in your own commitments. When your team sees you follow through on the hard things, they start doing the same.

The feeling when your head hits the pillow after an Adult All-Nighter session is pure, unadulterated accomplishment. It’s like finishing a workout in Rocky 4. You can't believe you did it, but you did.

The Hidden Truth About Burnout

Here's what most entrepreneurs get wrong: Burnout doesn't come from working too hard.

Burnout comes from working hard without seeing results. It comes from breaking promises to yourself. It comes from letting constant urgency override strategic importance.

When you design tomorrow today, you eliminate decision fatigue.
When you protect buffer time, you eliminate overwhelm.
When you keep promises to yourself, you build unstoppable momentum.

The DBQ
Every night, I ask myself one question: "What is one thing I can do tomorrow to make it better than today?" I call it the Do Better Question. The DBQ. Ask it consistently, and you begin to compound improvement.

Meaning… your tomorrow starts tonight.

Your 2-Week Challenge

Try this system for the next two weeks. Not forever… just for two weeks.

Week 1: Block all of your Fridays. Permanently. This Friday afternoon, perform your first Review + Preview ritual.
Week 2: Define your first official 2-week sprint with clear goals. When a new request hits your inbox, practice saying the magic words: "Next sprint."

This isn't about working more hours. This is about buying back your focus. It's about building trust with the most important person in your business: yourself.

And if you want a specific recommendation to guarantee your success….pick one Thursday in your upcoming sprint. Tell your family or roommates it's your Adult All-Nighter. Don't leave your desk until your most important project is finished.

Outworking the world is optional.
Outworking yourself is not.

That's how you design tomorrow instead of drowning in today.