Why Two Founders Declared War on Calendly

Every weekend, we tell the story of an idea that made it across the invisible line between imagination and reality.

Some start as sparks hidden in the vault of NTE Pro, waiting for someone to pull them into the light.
Others get a push from NTE Zero to One, where a framework helps them take their first real steps.
Many simply muscle through on persistence, luck, or a late-night burst of energy.

The paths are different, but the moment is the same:
A whisper becomes a word.
A word becomes a world.
And suddenly
It exists.

Yura Riphyak has raised money, built companies, and sold them.
Olena Vozna helped build Prozorro, the procurement platform Ukraine now uses for most of its army purchases.

Two seasoned operators. Two very different backgrounds.
But both got stuck on the same tiny, nagging thing: scheduling meetings.

Every time Yura sent a Calendly link, he cringed.
It felt like saying: “Here, you figure it out.”

Which is fine if you’re grabbing coffee.
But when you’re raising millions from a VC? Brutal.

“Calendly works for the sender,” he said. “But for the recipient, it still feels like a chore.”

Olena agreed. She used it for customer interviews. But inside her teams? Chaos. Too many calendars. Too many time zones. Too much awkwardness.

Calendly wasn’t broken.
It was worse: it was… impolite.

So they started building. Two weeks later, they had a Chrome extension. Today, it’s Alphie an AI assistant that lives inside Slack and handles the messy back-and-forth of scheduling for teams. Instead of everyone checking calendars and negotiating who can move, Alphie makes the trade-offs for you.

It wasn’t polished. It wasn’t perfect.
But it was alive.

Lesson 1: Awkwardness Is a Market Gap

Most founders chase “friction points.”
Yura and Olena chased shame.

That tiny pause before pasting a Calendly link? That was the market screaming: this isn’t it.

And they weren’t the only ones. In fundraising convos, VCs and founders said the same thing: scheduling links feel cold and transactional, not personal.

That social discomfort, something most people ignore became their wedge.

Calendly gave efficiency.
They wanted dignity.

Lesson 2: Validation > Vision

Instead of drawing up a TAM slide, they called the people who actually do this for a living: executive assistants.

They interviewed 30+.

The insight: fewer than 1% of meetings ever get rescheduled.

Translation: nobody wants to “manage” calendars. They just want it gone.

“Scheduling is one of the few things people are 100% comfortable delegating,” Yura said.

That flipped their perspective. The question wasn’t, “How do we make scheduling easier?”
It was, “How do we erase it?”

And then another unlock: EAs don’t just look for overlap. They start with the CEO’s calendar, the key person whose presence is vital but hardest to book. Then they negotiate with everyone else.

Scheduling isn’t just logistics. It’s hierarchy.

That nuance shaped Alphie’s DNA.

Lesson 3: Trust the Process, Not the Tools

Yura spent two months coding in VS Code.
Olena rebuilt the same thing in Replit in three days.

That’s when it clicked: the tool doesn’t matter. The loop does.

Build → break → debug → ship.

“After you break through a few blocks,” Yura said, “you start to believe — sooner or later — it will work out.”

That confidence became their operating system, their mantra: “Trust the Process.”

And their stack reflects it: Replit for the core build, v0 for the website, Claude Code for experiments.

No ceremony.
Just momentum.

Lesson 4: Multiple Shots on Goal

Most founders romance their MVP.
Yura and Olena date around.

They split the backlog: Olena built the Chrome extension, Yura handled the backend + web app. Then they layered Slack on top.

And they’re still shipping.

“Our idea validation strategy,” Yura explained, “is to launch a different product for a different audience every two months until the market response is strong enough.”

It’s not scatterbrain. It’s probes.
Each version is a dart at the market.

The goal isn’t polishing one shot.
It’s scoring eventually.

The Slack app has become their main focus.
Unlike the extension, it’s built for teams handling the messy dynamics of group scheduling right inside Slack.
Instead of manually checking calendars and negotiating who can move, Alphie makes the trade-offs for you.

Alive beats perfect. Every time.

Lesson 5: The Human Layer Is the Product

Calendly solved “find the time.”
Alphie solved the real problem: manners.

Their AI doesn’t just spit out slots. It reads the email or Slack thread, understands tone, and replies as if you wrote it.

That’s the leap: mechanics → manners.

“The next step,” Olena said, “is understanding priorities, which meetings should be scheduled ASAP vs who can wait.”

This isn’t automation for its own sake.
It’s personalization. And that’s what makes people lean in.

What They’re Doing Next

Their motto: launch something new every two months until the market pulls us in.

First came a Chrome extension. Then Slack,  now their main focus, helping teams cut through the back-and-forth of internal scheduling.

Next? A full executive assistant that doesn’t just handle scheduling but also travel, restaurants, even project management.

Not a shinier calendar.
A butler who never sleeps.

What They Think Needs to Exist

💌 An AI-native email client that sorts your inbox into personalized categories, prioritizes the important stuff, and auto-replies to junk.

📊 An AI assistant that plugs into your CRM and spins up a reactivation campaign from old leads.

🎤 An AI voice tool that fixes your accent live on Zoom.

In their minds, the future assistant doesn’t just run your calendar.
It runs your professional life.

What You Can Learn From Yura & Olena

🤝 Awkwardness is opportunity. If using a product makes you cringe, that’s a goldmine.

📝 Talk to the people who live the problem. EAs gave them insights no founder deck ever would.

⚙️ Tools don’t matter. The loop does. Momentum > mastery.

🎯 Don’t bet everything on one MVP. Keep firing shots until something sticks.

💬 The magic isn’t automation. It’s personalization, making tech feel like a human extension of you.

Follow Yura & Olena

👉 meetalphie.com — try Alphie
👉 Their blog — why AI will replace calendar apps
👉 readmake.com — indie hacker community they recommend

Calendly made scheduling efficient.

Alphie wants to make it invisible.

And that’s the pattern we look for at NTE. The tiny moments of awkwardness that reveal billion-dollar markets.

Their path is a reminder: every market has hidden edges. Sometimes it’s not the big, obvious pain point, it’s the awkward pause, the subtle cringe, the thing nobody writes on the whiteboard.

That’s what we hunt inside NTE Pro: overlooked angles, thousands of them, waiting for someone stubborn enough to chase.
And for the brave few trying to cross from idea to first build, NTE Zero to One exists to help make the leap.