Hey Deal Lifters 👋🔥
Some founder stories start with a garage.
Some start with a dorm room.
Today’s story starts with…
a WordPress blog.

No billion-dollar idea.
No fancy thesis.
No “pitch deck to raise pre-seed.”
Just a founder who had something to say — and hit Publish.

That founder? Jason Lemkin.

That blog? SaaStr.

That tiny idea?
Today it’s a media empire, venture fund, education platform, global events business, and a $100M+ revenue machine that practically defines the SaaS community.

Let’s break down how a handful of blog posts turned into:

• the largest SaaS founder community on earth 🌎

• a 12,000-person annual conference 🎤

• a top podcast 🎧

• a global SaaS brand 🔥

• and a venture fund investing in unicorns 💰

All built by one guy who missed the chaos of building.

Strap in. This is one of the greatest “small idea → huge outcome” stories in tech. 🚀

🧠 The Spark: “I Sold My Company… and I Felt Empty”

It’s 2011.

Jason Lemkin has just sold his second company, EchoSign, to Adobe for a reported $400 million.

Dream outcome.
Life-changing money.
Huge win.

But here’s the twist:

👉 Jason wasn’t celebrating.

He felt… empty.

Why?

Because the part he loved wasn’t the exit —
It was scaling something from zero to $100M ARR.

And suddenly… that chapter was closed.

He had years of hard-won knowledge in his head, yet no new company to channel it into.

So in 2012, he made a simple, almost silly decision:

“Let me write down the stuff I wish someone told me.”

No expectations.
No business model.
No grand plan.

Just one blog post on WordPress.

SaaStr was born.

✍️ 2012 — The Blog Era: Raw, Unfiltered, Real Founder Advice

SaaStr didn’t start polished.
It wasn’t a media startup.
It wasn’t even a “brand.”

It was Jason writing:

• brutal truths

• tactical frameworks

• lessons from scaling to $100M ARR

• the screw-ups

• the painful moments

• the advice no one else was giving

Every post felt like you were reading a private email from a mentor 10 years ahead of you.

And founders devoured it.

The blog spread like wildfire in SaaS circles.

This was pre-LinkedIn blowing up.
Pre-Twitter threads.
Pre-AI.
Real operator content was rare.

SaaStr became the place SaaS founders bookmarked, shared, and returned to daily.

👥 2013–2014 — The Community Era: “Let’s Meet in Person”

What happens when a blog hits product-market fit?

People want more.
More connection.
More founders.
More access.

Readers started emailing Jason:

• “Do you host meetups?”

• “Will you speak somewhere?”

• “Can we gather SaaS founders in one room?”

So Jason did something that now seems obvious:

He hosted the first SaaStr meetups.

Small. Simple.
A room full of founders sharing problems and solutions.

This was the first big unlock:

👉 SaaStr wasn’t just content.

👉 SaaStr was a community.

And communities scale in ways blogs never can.

🎤 2015 — SaaStr Annual: The First Conference (1,000+ Attendees)

Jason decided to take a wild swing.

A physical conference.
For SaaS founders.
Run by one guy… with a blog.

Most people expected a small event.

What happened?

🚀 Over 1,000 founders showed up.

🚀 Investors. CEOs. Operators.

🚀 Some of the biggest names in SaaS.

The first SaaStr Annual proved something powerful:

SaaStr wasn’t a blog anymore.

SaaStr was the center of gravity for SaaS.

Jason tapped into a global hunger for:

• transparency

• playbooks

• real talk

• connection

• mentorship

• community

And he built the stage where it all happened.

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🎧 2016 — The Media Empire Begins

With Annual skyrocketing, Jason doubled down on media.

✔️ Launches the SaaStr Podcast

Soon becomes one of the top SaaS podcasts in the world.

✔️ Launches the SaaStr Fund ($70M VC fund)

Invests in SaaS startups from within the community.

This was an unbelievable business model:

👉 The blog gave him traffic.

👉 The conference gave him influence.

👉 The podcast gave him distribution.

👉 The fund gave him equity & upside.

SaaStr turned from content → platform → ecosystem → empire.

🚀 2018 — SaaStr Pro + 12,000-Person Annual

By 2018, SaaStr wasn’t just big.

It was massive.

🎓 Launch of SaaStr Pro

A SaaS-focused learning platform with:

• courses

• templates

• how-to guides

• playbooks

• frameworks

🎤 SaaStr Annual explodes to 12,000 attendees

This event is now one of the world’s largest B2B software conferences.

It featured:

• CEOs of billion-dollar SaaS companies

• top VCs

• operators running billion-dollar ARR machines

• founders sharing everything from hiring to churn management

SaaStr became the Davos of SaaS.

🌍 2023 — The Biggest SaaS Community on Earth

By 2023, SaaStr had achieved something almost impossible:

✔️ A global community

✔️ Millions of followers

✔️ Events in the U.S. & Europe

✔️ Massive content reach

✔️ Venture fund with major wins

✔️ 100M+ in combined revenue streams

What started as a personal blog had morphed into:

A media company

A conference company

A VC firm

An online education business

A SaaS operator ecosystem

Jason Lemkin created the “Harvard of SaaS” without ever trying to.

And the wildest part?

He never planned any of it.

🧠 Why SaaStr Won (5 Foundational Levers)

1️⃣ Radical Transparency

Jason told the truth that other founders hid:

• the hard parts

• the mistakes

• the pain

• the tradeoffs

• the real math

• the emotional reality

Founders trusted him.

Trust compounds.

2️⃣ He didn’t chase trends — he chased needs

Founders desperately wanted:

• guidance

• mentorship

• connection

• frameworks

• answers to survival

SaaStr delivered all of it.

3️⃣ He built community, not “content”

Content gets read.
Communities get lived in.

SaaStr built:

• identity

• belonging

• shared struggle

• shared ambition

That turns followers into superfans.

4️⃣ He layered monetization after value

SaaStr didn’t start as a business.
It became one.

That’s why it worked.

5️⃣ He scaled breadth using a narrow wedge

The wedge was simple:

👉 “Advice for SaaS founders.”

From that wedge came:

• events

• media

• fund

• courses

• tools

• partnerships

A perfect example of depth → width strategy.

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💼 The Business Model Breakdown (How SaaStr Makes $100M+)

✔️ Events

SaaStr Annual generates tens of millions through:

• tickets

• sponsorships

• booths

• partners

✔️ Media

Huge distribution → lucrative sponsorships.

✔️ SaaStr Fund

Invests early in SaaS startups → massive upside.

✔️ SaaStr Pro

Subscription education revenue.

In short:

💰 Community → Content → Events → Fund → Ecosystem → Machine.

🧩 Founder Takeaways You Can Actually Use

✔️ 1. Start with what you know deeply

Jason had real SaaS battle scars.
People trusted him because he lived it.

✔️ 2. Publish obsessively

One post can change your trajectory.
Jason wrote hundreds.

✔️ 3. Communities are built, not bought

Consistency + value + vulnerability.

✔️ 4. Lean into demand

Meetups → conference
Advice → podcast
Community → fund
Questions → courses

✔️ 5. Don’t map the business model on Day 1

You don’t need to know what SaaStr will be in 10 years.
You just need to start helping people today.

🎯 Final Deal Lift Takeaway

SaaStr is proof of a timeless principle:

Small ideas become big empires when you show up every day.

Jason didn’t set out to build:

• a global SaaS conference

• a media empire

• a VC fund

• an online education platform

He just wrote.
He helped founders.
He shared truth.
He built trust.

And trust became a $100M+ business.

So next time you hesitate to publish, post, or share something?

Remember SaaStr.

Big things start small.
Huge things start consistent.

And sometimes, the next $100M idea isn’t a startup —
It’s a blog post.