Startup Corner #20: On timing, and why “Now” actually matters
What I think founders are really being asked when someone asks: “Why now?”
Hey friends,
This one’s been on my mind for a while.
You know that moment in a pitch — when everything’s flowing, you’ve made your case, you’ve laid out the product — and then someone pauses and asks:
“But… why now?”
It always feels slightly absurd when you hear it out loud.
Like they’re asking about something other wordly.
But when you sit with it, it’s probably one of the most loaded, consequential questions a founder can get.
And most people — myself included, at various points — stumble on this.
So I’ve been thinking through what this question really means.
I think “Why now?” is more than tech trends, or tailwinds, or a line in your deck that says “AI is hot.”
It’s a deeper one that lives somewhere between macro context and the founder’s personal conviction.
To me, “Why now?” is the investor’s way of asking:
“Is this the moment the problem you’re solving goes from annoying to impossible to ignore?”
They’re asking if the timing is urgent.
If there’s something in the water — a behavior shift, an infra unlock, a constraint that just lifted — that makes now the narrow window when your thing needs to exist.
Because most ideas are just early. Or late. Or were unreasonably hard to execute last year, but almost urgent to do this year.
And that delta — that timing delta — is where startups have the opportunity to break through.
Over time, I’ve started noticing that strong answers to “Why now?” often fall into one of three patterns.
1. The constraint just disappeared
This is the cleanest kind of timing. It says: this wasn’t possible before — and now it is.
Maybe because the infra wasn’t there. The regulation wasn’t friendly. The cost was too high. And then something shifted — and now the gates are open.
Some examples:
“It used to take six months to integrate cross-border payments. Now with open APIs, we can onboard in two clicks.”
“Data privacy laws just changed. The incumbents can’t move fast enough — we were built post-GDPR, not pre.”
You are basically saying: a roadblock lifted, and we’re the first ones through. That’s why we win.
2. The pain just became unbearable
This one’s more subtle — and powerful. It’s when the problem was always there… but something about the world just made people stop tolerating it.
Suddenly the workaround isn’t good enough. The duct tape falls apart. The spreadsheet is costing real money. And now your solution moves from “nice” to “need.”
Think:
“Teams were fine stapling together five tools. Then layoffs hit, and now they need one tool that just works.”
“Everyone used to ignore this risk — but now it’s on the CFO’s priority list. We’re getting inbound weekly.”
This version of “Why now?” shows you’re watching the emotional temperature rise.
3. The inflection point is here — and compounding
This one’s the trickiest — but maybe the most valuable.
It’s when a market crosses a threshold. Enough adoption. Enough tooling. Enough shift in behavior that the whole curve starts to bend.
That’s the moment to build — not when it’s hyped, but when it’s stable enough for the first scaled bets.
You might say:
“We’re not building the ground-level tech. We’re early in the stack that gets built on top of it.”
“The infrastructure is finally mature — and customers are buying.”
This is a quiet kind of timing — but investors who understand inflections will lean in hard here.
When you answer “Why now?” through one of these lenses, you’re showing that your entire company is shaped by the moment.
You’re in sync with the shift.
Your startup can define the shift and win it.
If you’re working on this question in your own pitch, here’s a prompt I find helpful:
“If this is such a good idea — why hasn’t it worked before? And why is this the moment it finally can?”
If you can answer that with specificity, you have a story that clicks into the present tense.
That’s when “Why now?” becomes the reason someone says yes.
— RB
Startup Corner