Craig was 42. Introverted. Bored. And Then He Built the Greatest One-Person Business on the Planet.

Hi all! Sorry we have been dark the past few weeks. I was unexpectedly invited to keynote a Startup Expo in Vilnius, Lithuania. It was a great experience, but I am back, here to regale you with more fun stories of entrepreneur derring-do!

Craig never planned to start a one-person business that would make millions. In fact, it all started with a simple email. That’s why he had . . .

• No investors

• No logo

• No staff (almost)

• No design

• No pitch deck

• No exit plan

Just a helpful little email list… that quietly became a billion-dollar website.

Origin Story

Craig Newmark spent decades as a quiet, competent software engineer. Not a founder. Not a visionary. A guy who liked computers, wore glasses, and did not get invited to a lot of parties.

In 1995, at the age of 42, Craig moved to San Francisco. Wanting to create a connection with the few friends he did have, Craig started emailing friends about local events, concerts, meetups, that sort of thing. A job opening here, an internship there.

It was nothing fancy, just a thoughtful guy helping people find cool stuff to do.

But his pals liked it. Loved it actually. Craig’s email list grew. And grew!

Unexpected Growth

People started replying: “Can you include apartment listings?” “Can I post a gig?” “Can I list my bike for sale?”

So Craig created a website. Again, it was nothing special. In fact, it was ugly. Gray. Clunky. But it worked.

Craig started to add some new categories. People started relying on it to find everything: Jobs, housing, missed connections, roommates, furniture, bandmates.

Even still however, there was hardly any monetization, certainly no branding. Bad design reigned. Still no logo.

Then, slowly, finally, he started charging just a few bucks for job listings. That alone made Craig’s list – Craigslist! - wildly profitable. Craig was able to expand into new cities and hire a few people to help him.

Then, of course, this being the dotcom era and all, the VCs started calling, but Craig was zero interested. He liked his small, profitable online business. It was fun. Valuable. He felt useful. He was making a difference.

Staying Small on Purpose

While dot-com startups in his neighborhood (literally, this was San Francisco after all) burned though millions, Craig spent next to nothing and was able to keep building one of the most trusted sites on the internet.

Craigslist became a quiet giant:

• 20 billion page views per month at its peak

• Operated with a team of about 30

• Craig personally became worth over $1 billion

Today, Craigslist

• Gets more than 100 million visits a month

• Is in over 500 cities in 70 countries

• Makes about $300 million a year  

The Takeaway

Craig was 42 when he started his email list. And he built his empire slowly. When everyone around him was chasing scale, Craig just kept helping people. he also did this on a shoestring. The growth funded the business.

You do not need funding or hype to build something great. Sometimes the most powerful thing you can do is stay small and stay useful.

Steal This Strategy

🛠️ Tool — One‑Person Empire Blueprint (Free Download)
Our one‑page business model canvas inspired by Craigslist: how to start, monetize, and simplify. Free to subscribers of Notes to an Entrepreneur!

📖 Book — Company of One: Why Staying Small Is the Next Big Thing for Business by Paul Jarvis
A smart case for why staying small can be a better way to grow.

🎙️ Podcast — Startups For the Rest of Us
Realistic guidance for indie founders building sustainable solo ventures.

🎥 Read — The Craigslist Story – Entrepreneur Magazine 
Short but rich breakdown of how Craigslist won by refusing to play the startup game.

TODAY’S POLL

About Steve

Steve Strauss is the best-selling author of The Small Business Bible (and 17 other books), Inc.’s small business columnist, a lawyer (non-practicing), and an entrepreneur. He sold his last venture, TheSelfEmployed.com to Mark Cuban & Zen Business. Need a ghostwriter or a newsletter for your business? Contact Steve!