Craigslist: A simple weekend hobby turns into a $3B empire

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Hey rebel solopreneurs 🦸‍♂️🦸‍♀️

You know that voice in your head whispering "I'm too old to start something new - everyone else started in their twenties, I've missed my window"?

Yeah, that age anxiety is lying to you.

Craig Newmark was 42 when he started emailing his friends about cool events in San Francisco... and that simple hobby became Craigslist, worth $3 billion today, proving your "late start" might actually be your biggest advantage.

But wait till you hear how it all started...

🧘‍♂️ Small town poverty kid

Craig Alexander Newmark grew up in Morristown, New Jersey, where his father sold everything from food to insurance just to make ends meet.

When Craig turned 13, his father died of lung cancer.

His mother Joyce had to move her two sons into a cheaper apartment and work as a bookkeeper, struggling to pay the bills.

Craig spent his childhood at the local junkyard and wore thick black glasses taped together with his torn shirt pocket held by a pocket protector.

Other kids didn't want to be friends with this awkward nerd who started his own club just to play board games.

He admits he had zero social skills and felt completely detached from other people.

Can you imagine feeling that isolated?

Nothing about his background screamed "future internet mogul."

And college? That's where things got interesting...

🧩 The coding years that almost crushed him

Craig earned scholarships to Case Western Reserve University, where he got his first glimpse of the early internet through Arpanet.

But he was too focused on classwork to see its potential.

After graduation, he landed a programming job at IBM and spent the next 17 years there, first in Florida, then Detroit.

He quickly learned that his lack of social skills held him back professionally too.

While reading "Neuromancer" in 1984, he saw a vision of what cyberspace could become - regular people with no power working together to create something bigger.

But he was still just another programmer, stuck in corporate life, watching that vision from the sidelines.

Sound familiar?

Then San Francisco happened...

🎪 A simple email that sparked everything

In 1993, Craig left IBM and joined Charles Schwab in San Francisco, evangelizing the internet to coworkers who barely knew what it was.

Two years later? He got laid off.

While working as a contract programmer, he noticed something beautiful happening around him...

People in San Francisco were constantly helping each other out.

Strangers told him which neighborhoods were good, where to shop, how to navigate this new city.

He thought, "I should give back too."

So on March 1, 1995, at age 42, Craig started emailing notices about cool arts and technology events to 10-12 friends using basic email software called Pine.

His friends started calling it "Craig's List."

That's it. No business plan. No grand vision. Just a guy wanting to help.

Pretty refreshing, right?

But then his simple email started taking on a life of its own...

🕵️‍♀️ Building something people actually wanted

Craig just kept listening to his users.

First it was arts and tech events. Then subscribers asked if he could pass along job postings or stuff for sale.

He sensed an apartment shortage, so he asked people to send rental listings.

Category by category, he added whatever people requested.

When his email list hit 240 subscribers and his Pine software couldn't handle the load, he had to figure something out fast.

So he switched to Majordomo - software designed for group emails.

When people suggested a website instead of emails, he sat down and coded one in Perl, registering Craigslist.org.

The response? Slow but steady growth.

He was still doing contract programming during the day and building Craigslist during breaks - 30 minutes contracting, 30 minutes Craigslist.

No fancy office. No employees. Just Craig in his apartment, listening to what people needed.

But success brought unexpected challenges...

⛳️ The temptations he resisted

By 1997, Craigslist was getting one million page views per month.

Microsoft Sidewalk approached him about banner ads - easy money that could have made him rich.

Craig agonized over the decision.

He thought about his values and asked himself: "How much money do I actually need?"

His contracting work was already covering his expenses.

So he said no to the banner ads because they would slow the site down and distract users.

That moment? It revealed what he calls his "moral compass" - choosing users over profits.

VCs and bankers kept telling him Craigslist could be a billion-dollar company if he'd just monetize properly.

But Craig had already decided: the site was good as it was.

Then reality hit him hard...

🌈 The breakthrough that almost broke him

Craig tried running Craigslist as a nonprofit with volunteers in 1997.

It was a disaster. Listings weren't posted on time, the database wasn't maintained, and everything fell apart.

His biggest job posters took him to lunch and said, "Craig, get real. Run this as a serious business."

In 1999, he incorporated as a for-profit company and started hiring full-time employees.

He quit his day job and committed fully to Craigslist, even though the revenue wasn't enough to cover his living expenses yet.

He had to live on savings for months, keeping his expenses low and just... persisting.

But he made one brilliant hiring decision: Jim Buckmaster as lead tech guy.

Craig quickly realized Jim could run things better than he could, so he promoted Jim to CEO in 2000 and moved himself to customer service.

With characteristic modesty, Craig started calling himself just a "customer service representative."

🎁 The empire built on simplicity

Today, Craigslist operates in 700 cities across 70+ countries.

It gets 20 billion page views and 80 million new ads every month.

The company is worth an estimated $3 billion, making Craig a multimillionaire.

And they still have only about 40 employees.

Craig charges for less than 1% of the site - just job ads in select cities and some apartment listings.

He never took outside investment, never had a grand strategy, and kept the design deliberately simple because users told him that's what they wanted.

While other startups burn through millions trying to scale fast, Craig proved that slow, steady growth focused on user needs creates lasting value.

🥂 Your turn to light it up!

Craig's "late start" at 42 became his strength - he had enough life experience to know what really mattered and enough wisdom to listen instead of rushing.

That patient approach generated over $120 million annually.

Your timing is perfect - just like Craig proved by starting at 42 with no rush to "make it" before some imaginary deadline, building something that outlasted all the twenty-something startups that burned out.

I'm pretty sure you're gonna catch everyone off guard.

Keep rocking! 🚀🍦

Yours 'anti-stress-enjoy-life-while building a biz' vijay peduru 🦸‍♂️