How Calendly Was Built from Maxed-Out Credit Cards into a $3 Billion SaaS

Most tech companies start with a pitch deck and a round of funding.

Calendly started with a problem, a hunch and a founder who emptied his savings and maxed out his credit cards to solve it. Today, it’s a $3+ billion SaaS tool used by millions around the world. But the path there wasn’t just unconventional, it was risky, personal, and entirely self-made.

This is how Tope Awotona built Calendly and why it changed SaaS forever.

The Scheduling Pain That Just Wouldn’t Die

In the early 2010s, Tope was working in sales, doing what salespeople do best: booking calls, pitching products, closing deals.

The bottleneck? Scheduling.

Every meeting meant a tedious back-and-forth:
“Can you do Wednesday at 2?”
“No, but I’m free Thursday.”
“What about next week?”

Tope looked around for tools that would fix it. Everything was clunky, outdated, or designed for large companies, not individuals who just needed to book a meeting and move on.

So he decided to build the tool he wished already existed.

Maxed Cards, No Team, No Funding, Just Conviction

When he pitched Calendly to investors, most of them passed.

“It’s too simple.”
“Google will kill it.”
“Nobody will pay for this.”

So Tope went ahead and did it anyway. He used up his life savings, maxed out multiple credit cards, hired a small dev team in Ukraine, and built Calendly from scratch, paying for it with borrowed money and belief.

“I had no backup plan. It had to work,” he later said.

No VC. No cofounder. No launch party. Just a founder chasing a very boring problem and refusing to quit until it was solved right.

By the way, if document sharing and analytics feel like scheduling did before Calendly, try Plox — a clean, affordable alternative to DocSend. Built for speed, not spreadsheets.

Growth by Simplicity

Calendly didn’t go viral. It grew organically.

• Freelancers added it to their email signatures.

• Recruiters used it to simplify back-to-back interviews.

• Sales teams started booking demos faster.

• Founders used it to stop wasting time on logistics.

One Calendly link led to another. People experienced it as recipients, then signed up themselves. The product did the selling.

Calendly became the default, not through marketing, but through usage.

$0 to $100M+ ARR, Still Bootstrapped

By 2021, Calendly had passed $100 million in annual revenue. It was being used at companies like Lyft, Dropbox, Compass, and thousands of startups who just wanted something that worked.

Tope eventually raised a $350 million secondary round at a $3 billion valuation, not to keep the business alive, but to take some chips off the table and reward early employees.

The company was already profitable, growing, and in control of its own destiny.

Why Calendly’s Story Still Resonates

Calendly wasn’t trying to change the world. It was trying to make one annoying thing, scheduling, less painful.

It succeeded because:

• The problem was real.

• The product was clean.

• The solution felt obvious, after someone else built it.

Calendly proved you don’t need 50 features to build a great SaaS. Sometimes you just need to own one moment in a workflow completely.

Final Thought

Tope didn’t invent a new category. He didn’t chase buzzwords or “disrupt” an industry. He fixed something people hated, and bet everything he had to do it.

Calendly now serves more than 20 million users in over 100 countries. Not bad for an idea most investors once dismissed as “too small.”

If you’re building or pitching, take notes from Calendly and if you’re sharing documents with no way to track or protect them, try Plox. It’s the Calendly of document sharing.