🧑🏻‍💻 Simplify: 0-$1M ARR playbook behind an AI job board

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This is the Squid Game-themed business card that helped Simplify land its first 10,000 users:

"There's a better way to make money. Discover your next internship at simplify.jobs"

Before we dive into the story behind this card, let's rewind to 2020 when the company was born.

Back then, Michael Yan was just another Stanford sophomore trapped in the exhausting internship hunt. He spent countless nights submitting over 150 applications, crafting 10 different resumes, and enduring awkward Zoom interviews during the height of the pandemic—only to be ghosted by recruiters.

Frustrated (and undoubtedly over-caffeinated), Michael decided he'd had enough.

He recruited his hallmate and a friend from a weekend hackathon to build a solution that would automate the mind-numbing job application process.

The initial intention was not to launch a startup. They just wanted to save themselves, and maybe some classmates, from the misery of repeatedly filling out the same forms and writing endless cover letters.

1/ First 2000 users: one viral LinkedIn post

The initial idea was simple: create a Chrome extension to help students automatically fill out job applications.

To gauge interest, Michael shared their MVP on LinkedIn (in fact, it was Michael’s first ever LinkedIn post), positioning it as a "common application for internships."

He was still new to the platform, without the coveted 500+ connections badge.

To everyone's surprise, it exploded overnight. The post garnered over 50,000 views and quickly built a waitlist of 2,000 eager students.

Seeing this overwhelming interest on LinkedIn, Michael and his team gained the confidence to pursue this idea further as a startup.

With their MVP and the initial LinkedIn hype, they applied to Y Combinator and landed a spot in YC's Winter 2021 batch.

They subsequently dropped out of Stanford to pursue Simplify full-time.

Swimming in a Sea of Competitors

While getting their first 2,000 users seemed effortless, the journey to 10,000 proved to be an uphill battle.

The job-hunting market was saturated, full of jaded people sick of platforms promising to solve all their job search woes.

Most students just didn't want to sign up for ANOTHER job board.

To attract more users, they tried various marketing tactics, including the classic move of sending mass emails to college mailing lists (we've all been there LOL 😂). It was about as effective as shouting into the void.

Students either ignored the emails entirely or deleted them without a second glance.

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2/ Next 100K: Squid Game & personal brand on LinkedIn

Squid Game stunt

With frustration mounting, Michael and his team knew they needed something radically different.

At that moment, Netflix's "Squid Game" was taking the world by storm.

Seizing this cultural phenomenon, they printed 25,000+ Squid Game-inspired business cards.

With the provocative message, "There's a better way to make money. Discover your next internship at simplify.jobs," they stealthily distributed these cards across Stanford, MIT, Berkeley, Northeastern, and Harvard.

The marketing stunt worked and finally helped them get over the hump, surpassing the 10K user milestone.

Building a LinkedIn personal brand

While the Squid Game cards kickstarted their user acquisition, Michael understood that sustainable growth needed more than clever stunts.

It required a memorable brand.

Given Simplify's focus on job searching, Michael leveraged LinkedIn to establish himself as a 'job search expert,' building on the platform that had brought them their initial 2,000 users.

He maintained a consistent daily posting schedule, finding particular success with the 'sharing job list → comment your email' format, regularly generating tens of thousands of views.

It has paid off big time. Today, Michael has over 144K followers on LinkedIn.

3/ Product iteration & current traction

What began as a Chrome extension for automating job applications has evolved into an AI copilot for the entire job search process.

Beyond the flagship autofill feature, the platform now offers:

• Job matches: match candidates with relevant job postings

• AI resume builder: use AI to tailor resume to fit the job description in a few clicks

• Job tracker: help candidates to track job applications and their status

For monetization, Simplify generates revenue from both sides of the marketplace.

It charges companies to post and promote job listings on their platform. For job seekers, Simplify offers a premium subscription service called Simplify+, which provides users with advanced AI features to enhance their job search experience, including AI cover letter generator, AI response writer, and unlimited AI resume tailoring.

Current traction:

As the platform has matured, it has expanded beyond its initial student market. Today, over 70% of job seekers on Simplify are experienced professionals.

Since its founding in late 2020, Simplify has processed 70M job applications, achieved millions in revenue, and grown to 800K+ job seekers—all with a lean, scrappy team of fewer than 10 people.

Now it's your move.

Got a bold, unconventional strategy to capture your first 10,000 users? Are you pushing the limits, or could you go even further?

See you next Tuesday 🫡,

Leo

p.s. My friend Tyler (Founder of Beehiiv) has a great newsletter called Big Desk Energy. He writes about startup insights and stories. ~90K founders read it every week. You should take a look!

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