Running Multiple Companies Without Losing Your Edge

Running more than one company isn’t about being a superhero. It’s about ruthless time architecture, clear decision boundaries, and knowing what only you can do.

1. Why I said yes to multiple companies

I didn’t wake up one day and decide, “I want three logos on my LinkedIn.”

Each new company came from:

• A real problem we hit in the previous business

• A distribution advantage we already had

• A team I trusted to own big chunks of it

If I ever start something that doesn’t check those three boxes, that’s probably pure ego.

2. Time architecture: lanes, not chaos

I try to avoid “context‑switch roulette.”

Instead, I think in lanes:

• Deep work blocks for each company

• Dedicated days or half‑days per company where possible

• Standing rituals (weekly reviews, leadership syncs) that don’t overlap

Practically, that looks like:

• No mixing of decision meetings from different companies in the same 2–3 hour block

• Clear “office hours” where teams know they have my full attention

• One personal review slot per week where I check numbers across everything

3. Decision boundaries: who owns what

To run multiple companies, I had to give up one fantasy:

The idea that I can or should be in every important decision.

So I draw boundaries:

• I own: vision, key hires, capital allocation, “we might die” topics

• Leadership teams own: roadmap, execution, day‑to‑day prioritization

• We share: culture, standards, and learnings across companies

If something sits in the shared zone too long, it becomes chaos. I push it to one side.

4. Dashboards instead of drama

For each company, I want one simple view:

• Cash / runway

• Pipeline and revenue

• Product usage / retention

• 2–3 company‑specific health metrics

I review these regularly instead of relying on “vibes” or Slack threads.

If a metric bothers me twice in a row, it gets a deeper review with the team.

5. Personal maintenance (without pretending to be a guru)

I’m not going to pretend I’ve hacked life. But I’ve learned:

• Sleep is not optional if you’re making high‑stakes calls

• Exercise is less about fitness and more about clear thinking

• Saying “no” is a skill you practice, not a switch you flip

When I overcommit, everything suffers: companies, team, and my ability to think long‑term.

6. A self‑check before you add “one more thing”

Before I say yes to anything big (a new company, product, or major project), I ask:

• Does this clearly compound with the assets I already have?

• Do I have a leadership team that can own 80% of it without me?

• Can I draw clear decision boundaries from day one?

• What am I willing to deliberately do worse or stop doing to make room?

If I can’t answer those, the answer is no—for now.

I share a more “raw” version of this on LinkedIn: what my actual weeks look like, what breaks, and what I’m adjusting. If you enjoy this level of behind‑the‑scenes, that’s where to follow along.