In 2013, I was Calendly’s first paying customer.

Sort of.

The product was free. I sent a check anyway. That’s how much I believed in it.

They never cashed it.

(It’s probably framed in the founder’s office by now. Okay, maybe not. But I like to think so.)

Tope Awotona — the guy who started Calendly — called to thank me. I was in my office in downtown Toronto. He just picked up the phone — no Calendly link, ironically — and we talked for 45 minutes.

He told me his story: There was a scheduling tool he loved when he was in sales. It went out of business. So he decided to build his own. He wasn’t even a coder — he hired a team in Kyiv to build it. Ruby on Rails, I think? Honestly, I’m not a techie. I just nodded like I knew what that meant.

Cool as a cucumber, this guy. Talking about his little startup like it was obvious it would work.

I told him about my app. I was building one too — a 12-month financial projection tool. Something that looked forward instead of backward. I’d tried Mint, Quicken, iBank, YNAB — none of them did what I needed. So I built my own.

I called it The Financial Clarity Workbook.

(Not exactly Silicon Valley. Maybe I should rebrand it as Finitybook. Too late now.)

Same year. Both of us building apps. Both convinced we were onto something.

Then he gave me advice I didn’t want to hear: “If you’re building an app, it has to be the main part of your business. It takes too much work to keep it updated otherwise.”

I nodded politely. Thought to myself: He’s also starting a business. His own idea. Doesn’t mean he’s right. Right?

Fast forward to today: Calendly is worth $1.4 billion. “Here’s my Calendly” is a sentence people say without thinking. It’s everywhere.

Turns out, Tope was right. Not my finest “I know better” moment.

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HERE’S WHAT I’VE LEARNED

Some problems are meant for apps.

Scheduling is one of them. It’s annoying. It’s repetitive. It doesn’t require behavior change — just fewer clicks. Calendly nailed it.

Some problems aren’t.

Financial behavior isn’t a scheduling problem. You can’t automate your way out of overspending when you’re stressed. There’s no button for “stop ordering DoorDash after a hard day.” No integration that fixes the patterns you inherited from your parents.

I built an incredible tool for the 20% — the numbers, the projections, the what-ifs.

But the 80%? The emotions, the habits, the patterns underneath?

That’s not a software problem. That’s a human-in-the-room problem.

Because here’s what actually happens in that work: Someone tells me about their spending, and halfway through the sentence, their voice changes. They look away. They say “I don’t know why I do this.” And we sit in that. Together. Until the thing underneath the thing starts to surface.

No app can do that. No integration. No automation.

Software can track your numbers. It can’t ask you why your chest tightens when you check your balance. It can’t notice the pause before you say “I’m fine.” It can’t sit with you in the silence after you realize the pattern started with your parents.

That’s human work. That’s the work I actually do.

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DO I HAVE REGRETS?

Tope’s a billionaire. So there’s that. 😄

But honestly? No.

I don’t want to run a billion-dollar company. The world has been screaming scale, scale, scale for years now. Bigger. Faster. More.

I’m going the other direction. Deep, deep, deep.

I thrive in small — a handful of clients, dedicated to helping individuals take control of their finances. Every client is a universe. That’s what I love.

(Also: no investors. No board meetings. No Slack channels with 47 unread messages.)

Calendly became a household name.

My app became a tool inside a practice built on something software can’t touch.

Different paths. Both right. ✨

—

WHAT ABOUT YOU?

Have you tried to app your way to taking control of your finances?

Downloaded the thing. Set it up. Connected your accounts. Watched the little pie chart spin. Felt good for about 72 hours.

And then… nothing.

A month later it’s sitting on your phone’s back screen, notification badge glowing like a tiny red guilt trip. You swipe past it. You’ll get to it later. You’ll “restart on Monday.”

(Meanwhile, the app sends you cheerful push notifications like “You spent $47 on coffee this month! 🎉” Thanks. Very helpful. I feel so seen.)

The app didn’t fail. The app did exactly what it was supposed to do.

It just wasn’t the right tool for the actual problem.

Because the actual problem was never the numbers.

It was the thing underneath the numbers. The reason you spend when you’re stressed. The reason you avoid looking. The reason you tell yourself “I’ll deal with it later” and later never comes.

That’s not a tracking problem. That’s a pattern. And patterns don’t break because you downloaded an app.

They break when you find the root. And start the repair.

—

WANT TO TALK?

👉👉👉 Here’s my Calendly →

Avraham
Your Financial Coach

P.S. At least one of us built a billion-dollar company. I just get to use the link. 😉