GrubHub : Coding at night side hustlers → Multi-millionaire founders

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Hey rebel solopreneurs 🦸‍♂️🦸‍♀️

Ever catch yourself thinking "Who am I to compete with niche experts who've been doing this for decades"?

You see their perfect credentials, their impressive networks, their years of experience, and that little voice whispers: "You don't belong here."

Meet Mike Evans and Matt Maloney - two regular programmers who felt the exact same impostor syndrome before building GrubHub into a $3 billion empire, proving expertise isn't everything.

But their journey to food delivery domination started with one freezing bus ride...

🧘‍♂️ Just two regular programmers

Mike Evans and Matt Maloney weren't restaurant moguls or business school graduates.

They were just web developers at Classified Ventures in Chicago, building websites like Cars.com and Apartments.com.

Regular guys with regular jobs, dealing with regular problems.

Like getting home exhausted after riding a packed, late bus in the middle of a brutal Chicago winter.

Can you imagine?

Mike would collapse into his apartment, barely having the energy to pour Lucky Charms for dinner.

The most entrepreneurial thing he'd done?

Crack open that massive Yellow Pages book to hunt for food delivery.

Sound familiar?

And Mike's ordinary frustration was about to spark something extraordinary...

🧩 The moment everything clicked

One cold January evening, Mike was riding the packed number 151 bus home from work.

The bus was late, crowded, and he found himself uncomfortably close to someone's armpit.

There was nasty slush from recent snow everywhere, and when he finally made it home, Mike was exhausted.

Picture this: You're exhausted, it's freezing outside, and you're starving.

You call seven restaurants before finding ONE that delivers to you.

Then you have to read your credit card number over the phone like it's 1995.

Sound familiar?

Mike felt that familiar pang every overworked person knows - there HAS to be a better way.

But here's what stopped most people: "Someone smarter probably already thought of this."

"Google will probably do this better than me."

"I don't know anything about the restaurant business."

Mike had all these same doubts swirling in his head too.

You know that voice, don't you?

So Mike did what any frustrated person would do - he called his friend...

🎪 The napkin that changed everything

Instead of just complaining about the problem, Mike called his friend Matt.

They met at Moody's Pub over burgers and beers.

Two programmers talking about a simple problem: Why isn't there geographic lookup for food delivery like there is for rental listings?

They grabbed a napkin and started sketching.

Not a complex business plan with financial projections and market analysis.

Just a simple idea: List restaurants that deliver to your address, and charge them a small fee to be featured.

That napkin sketch?

It stayed 75% true to GrubHub's core business model even after six years.

Can you believe that?

But here's where most dreamers stop and entrepreneurs begin...

🕵️‍♀️ The unglamorous grind

Instead of just talking about the idea over beers, Mike and Matt actually started building it.

While other startups were chasing investors and building fancy offices, Mike and Matt were doing something decidedly unsexy.

Making phone calls to restaurants.

One by one.

By one.

Mike built the website in the evenings while Matt spent his days on the phone with restaurant owners.

No funding.

No employees.

No fancy office.

Just two guys with day jobs, working nights and weekends, making hundreds of cold calls.

Mike knew this was his competitive advantage: "Nobody else is going to be crazy enough to actually call 20,000 restaurants."

Even Google wouldn't do it - they hate making phone calls.

But the real test came when Mike had to make a terrifying decision...

⛳️ The $140 reality check

Mike's advisor told him: "This will never get off the ground unless you really commit."

So Mike took a deep breath and quit his stable programming job to focus on GrubHub full-time.

The transition was terrifying - going from a steady paycheck to complete uncertainty.

His first month's earnings?

A whopping $140.

Ouch.

Most people would've panicked and crawled back to their old boss, begging for their job back.

But Mike had set himself a clear deadline: "If I can't support myself within the first 2 months, I'll quit."

That pressure forced him to focus only on what made money.

No time for perfect features or lengthy development cycles.

Just: Can someone pay for this?

Will they pay again?

And that's when Mike discovered something that changed everything...

🌈 The breakthrough nobody saw coming

Mike bought a book called "Sales for Dummies" because he was a programmer, not a salesperson.

The book taught him to walk through restaurant back doors instead of front doors to reach owners.

So there's Mike, walking into kitchen after kitchen, nervously pitching his website to busy restaurant owners.

But here's where it gets interesting...

Restaurant owners kept asking for features that didn't exist.

"Can you email our past customers?"

"Can you send out coupons?"

Most people would say "Sorry, we don't have that yet."

Mike gulped and said "Absolutely!" - then raced home to figure out how to actually build it.

Can you imagine the panic?

"Oh my God, I'm going to be up 20 hours tonight writing the software that I just sold to this guy."

Night after night, Mike and Matt would code frantically to deliver on promises Mike had made during the day.

He was building a complete CRM system one desperate promise at a time.

This willingness to promise and then deliver led to something remarkable...

🎁 The empire built on napkin logic

Today, GrubHub processes 175,000 orders per day and hit $3 billion in valuation at their IPO.

But wait, it gets better...

Mike still personally uses GrubHub to order his own food.

He still sometimes goes on sales calls to stay connected to restaurant owners.

That original napkin sketch?

Still drives 75% of their business model.

Two regular programmers with no restaurant experience, no business degrees, and no niche connections built a food delivery empire.

They did it by doing the work others wouldn't do and building what customers actually wanted to buy.

🥂 Your turn to shine bright!

Mike and Matt's "outsider" status became their greatest strength - they saw problems niche insiders had become blind to.

Their lack of restaurant credentials forced them to listen to customers instead of relying on assumptions.

Your outsider perspective is your superpower - just like Mike and Matt proved you don't need niche expertise to revolutionize an entire space.

I have a feeling you're about to surprise yourself with your own potential.

Keep rocking 🚀 🍩

Yours 'making success painless and fun' vijay peduru 🦸‍♂️