The CEO's Calendar: Where Founders Should Spend Their Time When Running Multiple Businesses

A few years ago I printed every meeting from my previous quarter and laid the pages out on a conference table in our Azagra office. The exercise took twenty minutes. The conclusions took weeks to digest. The wine business — by every honest measure the engine of the group — had received less direct CEO time than a real estate project that was, at best, our fourth strategic priority. I had spent more hours on the project that was loudest, not on the one that mattered most.

That experience, more than any book I have read on management, taught me what time really is in a diversified business. It is not a productivity problem. It is the most concentrated form of capital allocation a CEO does. Every hour spent on one business is an hour not spent on another. Every standing meeting is a recurring tax on the founder's attention. The companies inside a group that get the right share of CEO time tend to compound. The ones that do not, drift — slowly at first, and then suddenly.

Capital allocation gets the boardroom debates. Time allocation gets none. And yet for a founder running multiple businesses, the calendar is the strategy made visible.

## Why Time Is the Hardest Capital to Allocate Well

Money has reporting. A CFO can pull a report on where every dollar went last quarter. Time has no such system. Most founders have only the vaguest sense of where their hours actually went, and the vagueness compounds across years.

Money is fungible — it can be reassigned with a wire. Time, once spent, cannot. A morning spent in a non-essential meeting is not "inefficient capital allocation" you can reclaim next quarter. It is gone.

Money attracts professional attention. Time attracts none. There is no equivalent of an annual budget for the CEO's calendar. There is no committee that reviews whether last year's time spend matched the strategy. The asset that compounds the most ruthlessly receives the least governance.

For a founder who has built or acquired a portfolio of businesses, this asymmetry is dangerous. The structural complexity of a group — multiple verticals, multiple management teams, multiple geographies — guarantees that the calendar will fill with whatever shouts loudest unless you actively decide otherwise.

## The Four Categories of CEO Time

Every hour a CEO spends in a diversified group falls into one of four categories. Naming them honestly is the first step toward allocating them deliberately.

### 1. Compounding Time

Compounding time is hours spent on decisions, relationships, or initiatives whose value grows over years. Hiring a senior leader. Spending a day with a major partner you want to do business with for the next decade. Working on a brand decision that will define a company for a generation. Sitting with a successor in training. Defining a strategy that will guide hundreds of subsequent choices.

These hours feel slow in the moment. They produce nothing this week. They are also the hours that build durable value. Warren Buffett famously said that he spends 80% of his day reading and thinking. That is not laziness — it is the most concentrated form of compounding time available to him.

### 2. Coordinating Time

Coordinating time is hours spent aligning the company around decisions that have already been made. Operating reviews. Cross-business synchronization. Resolving conflicts between executives. Communicating priorities so the organization rows in the same direction.

This work is necessary. A diversified group without coordination becomes a confederation of fiefdoms competing for capital and attention. But it is the easiest kind of work to over-do. The temptation to add another standing meeting, another check-in, another forum is constant. The cost of those additions is invisible until you total them.

### 3. Reactive Time

Reactive time is hours absorbed by whatever has gone wrong this week. A customer issue that has escalated. A regulatory letter. A deal that suddenly needs the founder. A crisis at one of the businesses.

Reactive time has its place — particularly in genuine crises, where the CEO's presence is irreplaceable. The problem is when reactive time is not the exception but the rule. A founder whose calendar is dominated by reaction is not running the businesses; the businesses are running them.

### 4. Optional Time

Optional time is hours spent on things that feel important but are not. Speaking engagements that flatter the founder more than they advance the business. Meetings that could have been an email. Lunches with people who are interesting but not strategically relevant. Visits to businesses where the visit itself accomplishes nothing.

Every founder underestimates how much of their week falls into this category. The polite signals that come back from optional time — gratitude, attention, social validation — are the hardest signals to discount honestly.

## The Test I Ask Every Quarter

There is a test I have used for years, and which I recommend to every founder running more than one business. Print last quarter's calendar — not summarized, but every meeting. Then categorize each meeting in one of three ways:

- **Strategic to the future of the group** — these are the meetings whose outcomes will still matter in three years.

- **Necessary for the present operation** — these keep the engine running but do not change its trajectory.

- **Avoidable in retrospect** — these added little value and could have been delegated, deferred, or skipped.

Most founders find, when they do this honestly, that the third category is much larger than they thought, the second category is acceptable but bloated, and the first — the strategic future of the group — is much smaller than the rhetoric of their leadership would suggest. The gap between strategic talk and strategic time is the single most useful diagnostic I know.

## Three Frameworks That Help

Different founders allocate time differently because their businesses, life stages, and team strength all differ. But three frameworks have proven useful across many of the operators I respect.

### The 60/30/10 Heuristic

A useful aspiration for a founder of a diversified group is roughly 60% of working hours on compounding work, 30% on coordinating work, and 10% on reactive and optional combined. This is aspirational, not a rule. Most founders, before they audit, are running closer to 20/30/50 — far too much reactive and optional work.

The exact ratio matters less than the discipline of measuring it. Without measurement, the calendar drifts toward whatever shouts loudest, which is almost never what compounds.

### The Two-Lists Method

Warren Buffett supposedly told his pilot Mike Flint to write down his top 25 career goals, circle the top five, and then put the other twenty on an "avoid at all costs" list. Whether or not the story is literally true, the discipline is sound. Most founders try to do too many things, including things that are individually attractive. The list of attractive opportunities to decline is as important as the list of priorities to pursue.

In a diversified group, this discipline operates at every level: which businesses get most of your time, which projects within those businesses, which relationships you invest in, which industry events you attend. The five-or-six things that genuinely matter cannot get the attention they deserve unless the twenty-five attractive distractions are explicitly declined.

### The CEO's Three Jobs

A diversified-group CEO has three jobs that no one else can do. Hire and develop the senior leaders who run each business. Allocate capital across the businesses. Set the strategic agenda for the group as a whole. Almost everything else can be done by someone competent on the team.

Time spent on those three things compounds. Time spent on anything else is, at best, neutral and, at worst, a substitute for the work that only the CEO can do. The single most useful question I ask myself before adding something to the calendar is: would I be uniquely valuable in this room, or am I substituting myself for a leader I should be developing?

## Concrete Lessons From Running a Diversified Group

Some practical lessons I have learned the hard way:

- **Geographic clustering matters more than I expected.** When I have several businesses in different regions, the cost of switching contexts every two days is enormous. Blocks of three to five days in one region — Haro for hospitality and wine, Miami for the US business, Madrid for partnerships — are far more productive than fragmented travel.

- **The morning belongs to compounding work, always.** I protect the first three hours of the working day for thinking, writing, the most important conversations, and the decisions that will be irreversible. By midday, the world starts demanding things of me. By evening, I have less judgment than I had at 7 a.m. Important decisions made late in the day are, in my experience, almost always worse than the same decisions made first thing.

- **Standing meetings should expire by default.** A standing meeting that does not have a sunset clause becomes a permanent fixture, and the cumulative weight is enormous. Every recurring meeting on the calendar should have to defend its existence at least once a quarter.

- **The best businesses get less reactive time, not more.** The wine group, which is our largest and best-run, takes less of my emergency attention than smaller verticals. That is correct — strong leadership teams should not need the CEO weekly. The temptation is to spend disproportionate time on the strongest business simply because it is the most enjoyable. Resist it. The CEO's marginal hour usually belongs to the business that needs leadership development, not the one that already has it.

- **Travel itself is rarely strategic.** Being in the room matters; the flight does not. I try to schedule travel so that every trip has at least three high-value meetings — and to ruthlessly delete trips that have only one.

## A Word on Boredom and Discipline

Founders are temperamentally restless. Most of us started companies because we like building things and dislike repetition. That is exactly why time discipline is hard. The most strategic uses of CEO time — long-term thinking, careful hiring conversations, reading widely, sitting with a new acquisition for weeks before committing — are also the most boring in the moment.

The reactive work, by contrast, is exciting. A crisis demands action. A deal demands speed. A conflict demands resolution. The brain rewards us with adrenaline for solving these, even when they are not the highest-value work.

Disciplined founders learn to be suspicious of their own enthusiasm. The thing that feels urgent today is often less important than the thing that feels boring. The thing that produces a meeting tomorrow is often less valuable than the conversation that produces a partnership ten years from now.

## Key Takeaways

- For founders running multiple businesses, time allocation is the most concentrated form of capital allocation — and the calendar is the strategy made visible

- Every CEO hour falls into four categories: compounding, coordinating, reactive, or optional — most founders, before auditing, run far more reactive and optional time than they realize

- The three jobs only the CEO can do — develop senior leaders, allocate capital across businesses, set the group's strategic agenda — should dominate the calendar; almost everything else is delegable

- Print and categorize last quarter's calendar at least once a year — the gap between strategic rhetoric and strategic time is the most useful diagnostic available

- Standing meetings should expire by default — a recurring meeting without a sunset clause becomes a permanent tax on the founder's attention

- Protect the first hours of the day for compounding work — important decisions made late in the day are usually worse than the same decisions made first thing

- The best-run business in a portfolio should consume less reactive CEO time, not more — disproportionate attention to the easy business is a temptation to resist

Time is the only resource a founder cannot acquire more of. It does not respond to capital. It does not scale with hiring. It does not expand with success. The CEO who treats time as the scarcest capital in the group — and who allocates it with the same rigor as money — is the one whose businesses compound over decades. The CEO who lets the calendar fill with whatever arrives next is, eventually, the one whose businesses do not.