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Today’s breakdown is a masterclass in founder humility, customer obsession, and brutal pivots.

Most founders fall in love with their idea.
These three founders fell in love with the problem instead.
That’s why they built a $20B business while everyone else was still dreaming of making the next food app.

This is the wild journey of Toast — from three friends annoyed at a restaurant checkout… to powering 150,000+ restaurants, becoming a backbone of America’s hospitality industry, and ringing the bell on the NYSE.

Strap in.
This one is loaded with lessons you can steal today. 🚀🔥

🧠 The Spark: From “Paying the Bill Sucks” to “Restaurants Need a Brain”

It’s 2011.
Aman Narang, Steve Fredette, and Jonathan Grimm — three friends and colleagues at Endeca (later acquired by Oracle) — are grabbing dinner.

The food is great.
The vibes are good.
But the billing?
Painful. Slow. Annoying.

You’ve been there:
You ask for the check…
Wait 10 minutes…
Give your card…
Wait another 10 minutes…
Then it comes back with the little paper roll like it’s 1998.

While waiting, the three founders notice something:

👉 The POS terminals look ancient.

Big, clunky, grey hardware.
Slow as dial-up internet.
Servers tapping buttons like they’re disarming a bomb.

Their first thought?

“Let’s build a consumer app to let diners pay directly. Like Venmo for restaurants.”

This was the OG idea.

But then the founders did something rare but extremely valuable:
They went and actually asked restaurant owners what they wanted.

And the owners gave them a brutal truth:

Imagine having your big idea crushed in one sentence.
Most founders would ignore the feedback.
These guys didn’t.

That single moment sparked something bigger:

💡 Restaurants didn’t need a payment app. They needed a modern operating system.

Not “better checkout”…
Not “tap to pay”…
But a full-stack restaurant platform.

A brain for the restaurant → POS → Payroll → Inventory → Online ordering → Payments → Kitchen workflow → Data → Everything.

The kind of transformation Shopify brought to e-commerce.

And that’s when Toast — the real Toast — was born.
Not as a payment app…
But as a platform.

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🏗️ Execution: The Basement Era (2011–2013)

The founders incorporated the company in 2011 and worked from a Cambridge basement, fighting mold, dust, and outdated POS incumbents like NCR and Micros.

To build their MVP, they made two calls that seem obvious today but were revolutionary back then:

✔️ 1. Use Android tablets (cheap, mobile, modern)

Toast was early. Everyone else was locked into $5,000+ proprietary hardware.

✔️ 2. Make it cloud-based

Legacy POS companies were still selling servers that sat in the back room like a dusty PC from 1992.

The result?

👉 A sleek, cloud-based POS system on Android tablets.

Affordable.
Fast.
Easy to update.
Portable.
Modern.

This was years before the iPad-POS boom.

But here's the truth:

The early years were painful.

The founders literally walked Boston streets knocking on restaurant doors.
Cold-pitching.
Demoing.
Convincing skeptical owners who’d been burned by old POS vendors.

This was true “feet on the street” SaaS.
Not inbox outreach.
Not FB ads.
Door to door.

By 2013, they signed their first 50 customers.
Enough to validate the vision.

And enough to attract real capital.

💸 2016 — The Rocket Ignites: A $30M Series B

With traction building, the founders raised a $30 million Series B.

This wasn’t just a “hire engineers” round.
It was a “build the entire restaurant OS” round.

Toast expanded vertical by vertical:

🔧 Inventory management

👨‍🍳 Kitchen display systems

👥 Payroll & team management

🌐 Online ordering

💳 Payments

🧾 Receipts & reporting

📦 Delivery integrations

Suddenly, Toast wasn’t a POS company.

It was a complete operating platform.

Restaurants loved it because it replaced:

• 5 pieces of hardware

• 7 different software tools

• 50 headaches

With one clean integrated ecosystem.

And Toast didn’t just sell software — it sold efficiency, data, speed, growth, and reduced chaos.

That’s how you become indispensable.

💀 2020 — Toast Gets Hit With a Once-In-a-Century Disaster

Then came the pandemic.

Restaurants lost 80% of their revenue overnight.
And so did Toast.

In April 2020, Toast made a brutal call:

❌ Lay off 50% of its workforce

Thousands of employees gone.
Roadmaps paused.
Budgets cut.

Most companies would’ve died right there.

Toast didn’t.

They used the crisis to do something legendary.

🔄 2020–2021 — The Pivot That Saved Toast (and Thousands of Restaurants)

During lockdowns, restaurants needed:

🚪→ Contactless

🏃→ Fast ordering

📱→ QR-based menus

💳→ Mobile payments

🍔→ Takeout & delivery

🧾→ Digital workflows

Toast deployed a full suite of pandemic survival tools in months:

✔️ Order & Pay (QR codes everywhere)

✔️ Toast Takeout

✔️ Contactless payments

✔️ Handheld devices for servers

✔️ Delivery integrations

✔️ Curbside pickup tools

Restaurants that used Toast survived.
Many even thrived.

And Toast’s revenue rebounded like crazy.

This wasn’t luck.
It was responsiveness, speed, and a founder mentality that refused to die.

🚀 September 2021 — Toast Goes Public at a $20B Valuation

In 2021, Toast rang the bell on the NYSE.

💰 Nearly $900M raised

📈 ~$20B valuation

📊 One of the most successful restaurant-tech IPOs ever

From basement → IPO → billions.

This is what happens when:

• your product becomes essential

• your customers love you

• your timing aligns

• your pivot saves the industry

Toast was now powering restaurants nationwide like:

• Sweetgreen

• Joe & The Juice

• B.GOOD

• Hundreds of thousands of small local restaurants

Toast wasn’t just selling software.
They were building infrastructure.

🍽️ 2025 — Toast Dominates the Restaurant Industry

As of 2025:

👉 Toast powers 150,000+ restaurant locations

👉 Their platform is the default OS for modern restaurants

👉 They’re expanding aggressively into:

• lending

• capital

• supply chain

• loyalty programs

• AI menu optimization

• workforce management

Toast is no longer a POS company.
Toast is the nervous system of American restaurants.

And they’re still growing.

🧠 Why Toast Won (The 5-Lever Breakdown)

1️⃣ They listened to customers — not their own idea

The founders didn’t cling to their initial app vision.
They pivoted based on real problems.

2️⃣ They built vertically, not horizontally

Most POS systems stop at payments.
Toast went deep:

• inventory

• payroll

• team scheduling

• delivery

• online ordering

• capital

• hardware

Owning the full stack = unbeatable retention.

3️⃣ They made the right enemies

Legacy POS providers were slow, expensive, hated.
Great industry to disrupt.

4️⃣ They used hardware as a Trojan horse

Once Toast’s hardware is in the building, switching becomes painful.
Smart.

5️⃣ They pivoted at the perfect moment

The pandemic should’ve killed them.
Instead, it turned Toast into an essential lifeline.

🧩 Tactical Lessons for Founders

✔️ Your first idea is rarely the right one

Listen aggressively. Pivot ruthlessly.

✔️ Solve the biggest pain in the value chain

Not the cute problem — the expensive problem.

✔️ Build vertically-integrated ecosystems

It creates insanely high switching costs.

✔️ Crises create category leaders

If you respond faster than competitors, you win permanently.

✔️ Make your product indispensable

If your customers can’t run their business without you, you become a billion-dollar company.

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🎯 Final Deal Lift Takeaway

Toast isn’t a story about tech.
It’s a story about listening, pivoting, and going deeper than anyone else was willing to go.

The three founders didn’t build a payment app.
They rebuilt the entire restaurant industry.

That’s why they’re worth $20 billion.

And that’s why their story belongs in your founder playbook.