I spent last Saturday watching old Roger Federer matches. More specifically, the 2009 Wimbledon final against Andy Roddick. Five brutal sets that took just under five hours. And yes, I maintain that’s an excellent way to spend a Saturday afternoon.
What fascinated me wasn’t the tennis itself, but rather the contrast in visible effort.
Roddick was changing shirts every half hour. Grunting through long rallies. Taking deeper breaths between points. By the fifth set he was beginning to limp.
Federer, at the other end of the court, hadn’t even unbuttoned the top button of his shirt. If you muted the television, you could have mistaken the fifth hour for the first. It all looked absurdly effortless.
Years later I watched an interview where Federer admitted he actually disliked hearing that.
People would tell him how natural it all looked. How easy he made tennis seem. What they never saw were the thousands of hours spent on footwork, conditioning and repetition that made it possible to look that way.
The work hadn’t disappeared.
It had simply become invisible.
In Milan last week I learnt that the Italians have a word for this. Sprezzatura, the art of concealing effort so completely that whatever you’ve done appears to have cost you nothing.
I’ve thought about that word all week, because it explains something I’ve never managed to say cleanly to a founder.
I can usually tell within two or three slides whether a founder understands his own business. Not from what’s on them. From what isn’t.
I’ve reviewed more than 700 fundraising decks over the past few years.
The best ones all have sprezzatura. They’re almost never the ones carrying the most information.
They’re the ones where every difficult decision has already been made before I open Slide One.
Ten or twelve slides.
Short sentences.
One chart.
No jargon.
No tour through every feature the product has ever shipped.
The deck that was never the problem
A few weeks ago I read a deck from an operator with eighteen years in his industry. A man who has forgotten more about his market than most of the people who’d fund him will ever learn.
Slide four was a market map with eleven logos. Slide five had three customer segments, each with its own value proposition. Slide seven was titled Phase 2 & 3.
Nothing on those slides was wrong. Every claim was defensible, every segment was real, and he could have held the floor for an hour on any of it and won the argument. But as we know, founders don’t have an hour.
I already knew what the first three investors had told him, because it is what they always tell him. Interesting. But what does it actually do?
He read that as a comprehension failure. He assumed he hadn’t explained himself well enough. So the next version was longer.
That’s almost always what happens.
Investors say: I don’t get it.
Founders hear: explain more.
They almost never hear: decide more.
And I understand why. Decide more sounds like being asked to be less right. He has evidence for all three segments: real customers, real revenue, real conversations. Deleting two of them doesn’t feel like editing. It feels like leaving value on the table.
So he adds a slide instead. And the deck gets longer every time it gets rejected.
You can usually find the undecided parts in about four seconds. Search the deck for phase two, and/or, multiple, and among others. Every hit is a decision someone declined to make in writing.
Better decisions, not better words
Most founders think a great deck is the result of great writing.
I don’t think it is.
Great decks aren’t built by finding better words. They’re built by making better decisions.
Deciding which customer actually matters.
Deciding which market you’re not going after.
Deciding which feature doesn’t belong.
Deciding which proof deserves an entire slide and which proof deserves deleting.
Every sentence that disappears represents a decision that finally got resolved. That’s why the work is invisible.
The last deck I worked on properly went through nine versions. Three of them were the same eleven slides in a different order.
And one of the hardest hours I’ve spent with a founder was deciding which of two customers to name on slide three. We didn’t write anything that hour. We just argued about which one he’d rather be wrong about.
What AI changed
I think AI has made this even more interesting.
AI is brilliant at generating possibilities. Fundraising rewards eliminating them.
Every slide used to cost you an afternoon. That friction was doing your editing for you and you only built the ones you actually needed.
Now the marginal cost of one more slide is a prompt.
Nothing is stopping you any more. That’s the problem.
The instinct is to show everything so nobody can accuse you of missing something.
Federer’s problem was that people couldn’t see his work.
You’ve laid every hour of yours out on the page and assumed covering every base was the safer bet.
The guardrail
If you take this as strip it back, you’ll strip the wrong things.
The specifics are your substance. The named customer. The number nobody outside your industry would know. Those are the only reasons a stranger believes you over the four other decks he read that morning.
Cut those and you land on a deck that is simple and says nothing, which is a worse failure than the crowded one. At least the crowded deck proves you know something.
Sprezzatura is concealed effort, not absent effort. Federer’s collar stayed done up because of the conditioning, not instead of it.
What it comes down to
The first deck an investor sees isn’t really a presentation.
It’s evidence.
Evidence that you’ve already fought the difficult battles. Evidence that you’ve chosen. Evidence that you know the difference between what matters and what merely exists.
Obviousness is expensive. It costs hundreds of decisions nobody in that room will ever see you make.
Federer never wanted his work hidden. You don’t get the choice. Yours has to disappear into ten slides, and the only thing left showing is what you decided to leave out.
ONE QUESTION
I often ask founders why a slide is there.
The answer is almost always a story about a meeting rather than a reason. Which slide in your deck exists because someone once asked about it?
Send it to me as reply. I’ll tell you what it’s doing to the rest of your deck.
The Quote
"I was working on the proof of one of my poems all the morning, and took out a comma. In the afternoon I put it back again."
Oscar Wilde
A whole day's work, and the page ended up exactly where it started. That day is in the poem anyway, it's just not visible.
Clipped
Just came across a transistor chip under the microscope.
A fingernail of grey silicon that looks like nothing at all. Zoom in far enough and you're looking at eighty years of human engineering progress and every bit of it invisible at normal size.
Written from the other side of the table.