Diary of a CEO

The inside joke of success.

July 26, 2026 · 5 min read

I just had to share this... 😉

Dear Diary

Dear Diary,

I woke up in paradise, but it’s eerie.

It’s morning in our little house in San Juan. Most of the staff aren’t here yet, but the gardeners will arrive soon, hacking away the jungle that tries daily to swallow our home.

So for now, it’s just me and the quiet – except for the kids knocking around some pans every now and then. They’re dressed and making poached eggs, ahi sashimi, and whole-grain ricotta pancakes for the family. They’re executing the morning like two little stormtroopers down there. They’ll leave a mess, but Jacques will make it disappear when he starts dinner (et voila).

Julius and Calliope will probably grow into entitled adults, but Silvia and I comfort ourselves knowing we’re at least giving them a leg up on the competition.

Speaking of gorgeous Silvia, I’m sipping my cortado and looking over at her as she sleeps a little more on her side. She’s enjoying the new 10,000-count Syrian cotton sheets we just got off the black market. Egyptian cotton has nothing on these. Forget blood diamonds. Gimme blood sheets.

Happiness Isn’t a Warm Gun

I should just sip mojitos with my very fit wife. Everyone at the Yale Club thinks I have it made. But something’s bothering me.

👀 See, I realized that I’m a fraud. Sure, there’s some insider trading and scammy sales tactics, but we settled those out of court. Besides, that’s not what I mean.

The problem is that what I do – in the rare times I’m actually working – isn’t that complicated.

I spent two years at Wharton learning how to model cashflows. What a waste. Samuel’s got that. The guy dreams in Excel.

Like Henry Ford, I hire experts who know all the technical aspects.

What I do is… simple.

It takes some experience, and leadership is indeed a skill that takes a long time to master. But one could argue that the skills I excel at are pretty easy compared to data science, M&A law, and systems engineering.

🧐Like the Bobs say in Office Space, “What is it exactly… ya do here?”

Great question! This is what I do at Vanderveld Inc.:

People
✅ Hire amazing people
✅ Trust those people to do their job
✅ Develop them as much as I can
✅ Read people and situations

Operations
✅ Enforce a high quality bar
✅ Ask powerful questions
✅ Optimize our systems

Culture
✅ Nurture and guard our culture
✅ Communicate and inspire
✅ Groom leaders

Decisions
✅ Make decisions – and build systems so others can make them instead.
✅ Take prudent risks
✅ Develop strategy

Capital
✅ Make sure we don’t run out of money
✅ Assure investors that this isn’t all a house of cards

Again, some of these things are skillsets. But most of them are just… behaviors and character traits. Not certificates – pattern matching.

Coursera didn’t teach the tiger to hunt.

Smoke and Mirrors

Society’s hiring and performance-management systems make it SEEM like there’s a meritocracy. That all that a senior manager needs to do to make it to director is master some skills they don’t know. But the guys who park their yachts in the cove where mine is know this is complete BS.

Many of them are walking HR violations.

Some barely passed high school.

Yet… who runs the show?

Meanwhile, there are some non-obvious things that make me guilty about that list above:

Long ago I was a technician, but most of that was a waste of time. I could’ve gotten where I am now faster if I’d focused less on “skills.”
The managers in my company who my lieutenants think are the “fast-promotes” are the ones who can do the same ‘30,000-feet’ things I do, even if they write the sloppiest code on their team.
AI will replace my employees’ jobs faster than mine.

What Silvia knows is that I’m a high-functioning buffoon.

It makes her laugh. And love me.

The King of Comedy

Does anyone else at Vanderveld see this?

I once heard this guy Sri who was a Navy SEAL talk about how you look around after Hell Week at all these other amazing dudes and you think, “Wow, I can’t believe I’m around these guys.”

I feel like an imposter. I guess that’s the inside joke of success.

The irony is as thick as ricotta pancakes with lemon curd. And it begs a fundamental question:

📌 Why, if my job is so basic, doesn’t everyone do what I have done?

Put another way: Why do people bury themselves into nerdy, technical pursuits instead of being a master of the universe at Castle Grayskull?

Maybe they felt more imposter-y than me?
Do they just accept less? (Maybe this is a virtue?)
Or maybe they’ve been sold a lie about how to get ahead in this world by other people who are scared to do anything – besides what other scared people told them the playbook was.

I suppose the one thing I’ve been willing to do is to face myself.

↳ To expose myself.
↳ To get through the discomfort.
↳ To know that if results don’t show up, it’s on me.

Weirdly, I feel freer this way… more human. Primal.

I joke in meetings 🃏
I ask stupid questions 🙊
I veto nonsense 🙅‍♂️

– all while they don masks to
climb ladders with half the
rungs knocked out. 🪜🎭

Irony: Part Deux. 🎬

I guess many of them can’t face themselves because they’ve never truly found themselves. 🔎

That’s forgivable.

I pity the ones who know they’re meant for more – and still take orders from me.

Clement R. Vanderveld
CEO, Vanderveld Inc.

(Note to self: Yes, I sign all of my diary entries with my full name and title.)

Coda

You know who has two hands and doesn’t accept less?

❤️ Andrew

Outro

This is credited to both John Lennon and Paul McCartney, but Sir Paul says it was basically John “having a lot of fun.”

It’s actually about sex — and maybe heroin.