The most common question I get isn’t about funding, strategy, or writing.
It’s this: “How do you manage all that without burning out?”
The short answer: systems.
The long answer: systems that are simple enough to survive chaos but strong enough to keep me accountable.
I’m not a productivity saint. I’ve had years where my calendar was a graveyard of half-finished projects, my books gathered dust, and sleep was an afterthought. What changed wasn’t willpower—it was the way I designed my days to protect both my ventures and my health.
The Non-Negotiable Bedtime
If there’s one thing I’ve stopped negotiating with myself, it’s sleep. I’m in bed at 11 p.m. Lights off, phone away. Seven hours, minimum.
Why? Because I’ve seen the cost of skipping it. Bad decisions, short tempers, and “busy” work that leads nowhere. Without rest, I’m running my companies like a drunk pilot—technically flying, but headed for disaster.
This certainty around sleep ripples into everything else. My team knows I’m not replying to Slack at midnight. Clients know my deep work happens early. My body knows when it’s time to shut down. That rhythm makes me sharper when it counts.
One Calendar to Rule Them All
When you’re running three ventures, it’s easy to let one steal time from another. That’s why I operate from a single, unified calendar.
Every meeting, deadline, and personal commitment goes here. Color-coded:
- Blue for Venture A
- Green for Venture B
- Orange for Venture C
- Grey for personal life and writing
This fairness isn’t about giving each venture equal hours—it’s about ensuring no project gets neglected because it’s “out of sight.” When I open my week, I see exactly where my time is going, and if one venture is hogging the spotlight, I rebalance.
The Weekly Output Goals
Most people measure productivity by how much they do. I measure it by what gets finished.
On Sundays, I set output goals for each venture and my writing. Examples from last week:
- Finalize investor deck for Venture A
- Publish 2 blog posts for Venture B
- Launch customer feedback survey for Venture C
- Write 3,000 words for my next book
By Friday, I review. Did it ship? Yes or no—no “almost done” points. This builds status—I get a measurable sense of achievement every week, instead of drowning in endless work.
Context Switching Without Losing My Mind
Switching from negotiating a partnership deal to editing a book chapter is a mental whiplash most people underestimate. I’ve learned to separate my days into “maker” and “manager” blocks.
Mornings are for creation—strategy decks, writing, deep problem-solving. Afternoons are for calls, reviews, and decision-making. If a venture needs something urgent outside its slot, it better be truly urgent.
This gives me autonomy over my focus. I decide when I’m in builder mode or boss mode, instead of letting the day dictate it for me.
The Digital-Brain Split
I’ve accepted that my brain stores creative ideas and structured tasks in different ways. So I built my tools to match:
- Obsidian: My “idea vault” for books, speeches, and research. No deadlines, just connections.
- Notion: My operations hub for ventures—project timelines, SOPs, client pipelines.
- Paper notebook: My capture tool for anything raw, urgent, or emotional.
This relatedness—working in harmony with how my mind naturally sorts information—means I don’t waste energy forcing myself into a single system that doesn’t fit.
Delegation with Teeth
Delegation isn’t about pushing tasks downhill. It’s about giving someone a piece of the outcome.
When I delegate, I make sure three things are clear:
- Outcome — what “done” looks like.
- Deadline — when “done” happens.
- Authority — what decisions they can make without me.
This isn’t just fair to them—it’s fair to me. I can actually let go because I know they own it. My ventures move without my constant hand on the wheel, which keeps me free to write and think big.
The Health Baseline
I treat health like venture zero—the one that funds all others. My baseline:
- Walk 10,000 steps daily
- No more than two coffees
- Strength training twice a week
- One full day off screens every month
This gives me certainty that no matter how intense a quarter gets, I’m not slowly eroding my ability to run the other three. You can’t outsource your health to an assistant.
Saying “No” Without Guilt
Every “yes” to a shiny new idea is a “no” to one of my existing ventures or my writing. I’ve learned to ask:
Does this align with my top three goals for the quarter?
If not, it’s a no—politely, firmly, without apology.
This is pure autonomy. I’m building my life on purpose, not by accident.
The Real Payoff
Running three ventures and writing books isn’t about heroics—it’s about systems that protect the important things from the urgent things.
These systems don’t just keep me productive; they keep me human. I still have dinner with friends. I still read for pleasure. I still wake up without an alarm most days.
And yes, I still get my seven hours. Because no venture, no book, no deal is worth sacrificing the clarity that only comes from a rested mind.