TTL 30
Good Morfternight friends,
Let’s talk about secrets.
Not the “gossip at dinner” kind — the business kind.
The kind that shapes negotiations, partnerships, and entire company trajectories.
More specifically:
→ How do you keep something private once it’s out of your head?
→ And what are you trading off every time you share it?
→ How do you keep something private once it’s out of your head?
You can’t. The moment an information leaves your head, it’s no longer really a secret.
It doesn’t matter if you only told your closest friends.
It doesn’t matter if someone signed an NDA.
The moment information escapes that controlled space, you lose track of where it might go. It spreads — like a virus.
I tend to think of information in 3 buckets:
- Private (only in my head)
- Public (everyone knows)
- Shared but limited (2, 12, maybe a few thousand people know — but it’s unlikely to spread further)
Type 3 is my favorite, but it’s also the hardest to achieve.
Why? Because people don’t keep secrets — incentives do.
The only real lever you have is ensuring that the people you share your information with want to keep it private — ideally as much as you do, or even more.
Take acquisitions: when Google sold Google Domains to Squarespace, the deal became public only after it was finalized. Why?
Because both parties had something to lose if it leaked.
- The buyer wanted to prevent competing bids from driving up the price.
- The seller wanted to avoid unsettling customers.
- Both sides wanted to avoid spooking markets or alerting competitors.
In these cases, privacy isn’t maintained because people are naturally discreet. It’s maintained because breaking it works against everyone’s interests.
→ What are you trading off every time you share a secret?
Squarespace had a clear reason to keep the deal under wraps: avoiding competition. If word got out, other buyers might have entered the picture, prices could’ve spiked, or the product’s value might have been undermined — all of which could complicate or derail the acquisition.
Google had similar incentives to keep things quiet — but their choice came with a trade-off.
Every secret involves a balance between control and opportunity.
By keeping the circle tight, Google avoided a customer exodus. But they also avoided potential bidders — and likely sold for less than they might have in a competitive process.
The tighter the circle, the lower the risk — and the lower the upside.
- Keep the circle small → more control, less opportunity
- Widen the circle → more risk, but more upside
That decision depends entirely on what’s at stake. How bad would it be if the information leaked?
In everyday life, the answer is usually: not that bad.
Think of privacy settings on LinkedIn or Instagram. You can fine-tune them endlessly, but for most of what we post, it just doesn’t matter much. Nothing happens. There are no real consequences.
So the more relevant question is often:
Would anything meaningful happen if this got out?
If not, the urgency to control the information might be overstated.
In the end, the risk of sharing isn’t just about what is shared — but with whom, and why.
What are their incentives? What’s the worst that could happen? And is the upside worth the risk?
Because secrecy isn’t free. It protects — but it also limits.
The mental model I use:
Whenever I’m deciding how much to share — whether it’s business, negotiations, or personal life — I ask myself two questions:
1️⃣ Do the people I share it with have more to lose than gain if it leaks?
2️⃣ What are the consequences if this becomes public?
If the answers aren’t clear, maybe I shouldn’t share it.
That’s it for today.
See you next week — no secrets on my end. But feel free to share yours. It’s just a public blog… what’s the worst that could happen?
If someone forwarded this to you, you can subscribe.
I also publish on paolo.blog and monochrome.blog.
Leave a Reply