The Hustle Playbook: How They Built a $27M Media Empire (And How You Can Too)

Back in 2016, The Hustle was just a scrappy email newsletter written by a dude with questionable sleep habits. Fast forward to 2021, they sold the business to HubSpot for a reported $27 million. And they did it without venture capital, without clickbait garbage, and without burning out.

So how did they pull it off? Here’s The Hustle Playbook—the exact blueprint they followed to build one of the biggest business media brands of the decade.

1. Start with an Audience, Not a Product

Most people build a product and then hope someone cares. They flipped it. They built an audience first.

• Step 1: In 2015, he launched Hustle Con, a conference for startup founders. I used the event to capture emails (because emails = money, remember this).

• Step 2: Instead of letting those emails rot, he started sending a daily newsletter with engaging, fun business news. Think: Morning Brew meets Barstool Sports.

• Step 3: The audience grew fast. We hit 100,000+ subscribers in their first year. Why? Because they wrote like real humans, not corporate robots.

👉 Lesson: Build an audience first. Then, monetize later.

2. Write Like You Talk (And Be Ridiculously Useful)

Most newsletters are boring. Too many buzzwords. Too much fluff. They went the opposite route: straight talk, useful insights, and a sprinkle of personality.

• They wrote at a 5th-grade reading level (because busy people don’t have time for fluff).

• They cut the B.S. If it wasn’t useful or entertaining, it didn’t go in.

• They made it fun. People don’t just read news—they want to enjoy it.

👉 Lesson: If your content isn’t engaging, no one will share it. And if no one shares it, you’re doomed.

3. The Growth Engine: Referral Loops & Viral Content

They grew organically (translation: for cheap) because they baked virality into their system:

• The Referral Program: Get 5 friends to sign up? Boom, free Hustle swag.

• Controversy & Curiosity: They wrote stories that got people talking.

• Shareable Hooks: Their subject lines weren’t just headlines—they were click magnets.

Result? They hit 1M subscribers in 4 years with almost zero paid ads.

👉 Lesson: Make it stupidly easy for your audience to spread your content.

4. Monetize Like a Business, Not a Blog

Most newsletters make pennies with Adsense. They made millions with a different approach:

• Premium Ads: They charged high rates ($50–$100 CPM) because our audience was premium.

• Paid Products: They launched Trends, a $299/year research product. It hit 8 figures in revenue.

• Events & Sponsorships: They leveraged their audience for in-person and digital events.

👉 Lesson: If you have a valuable audience, brands will pay big to reach them.

5. Exit Like a King

By 2021, they had:

• 1.5M subscribers

• $15M+ annual revenue

• 95%+ of revenue from owned audience (not social media algorithms!)

HubSpot came knocking. They sold for $27M and lived happily ever after.

👉 Lesson: Build an asset, not just a business. Assets get bought.

Final Takeaways (a.k.a. Your Blueprint to Riches)

1. Audience first, product second (Your email list is the real goldmine.)

2. Write like a human (No one cares about corporate fluff.)

3. Engineer virality (Referrals + shareable content = free growth.)

4. Monetize smartly (Premium ads, paid products, not just Google ads.)

5. Think like an asset owner (Build something sellable.)

That’s the playbook, folks. Now go start building your own $27M media empire. No excuses.