Building a $100M+ Newsletter Business: Insights from Sam Parr and Alex Lieberman

Wonder how two founders turned simple email newsletters into high-value media companies? Sam Parr of The Hustle and Alex Lieberman of Morning Brew reveal their journeys, challenges, and lessons for growing subscribers, monetizing content, and navigating a sale.

The Early Days: Rivalry and Respect

Sam Parr and Alex Lieberman entered the mid-2010s newsletter scene as scrappy competitors who soon discovered mutual admiration. Sam admits he envied Morning Brew’s welcome email:

“I remember reading the welcome email and being like, ‘This is so freaking good.’”

Alex and Sam quickly realized they were part of a new wave of entrepreneurship, shaping what email newsletters could be. “We didn’t invent it, but we kind of helped pioneer a little bit of what is popular today,” Alex reflects. Both started in college—Alex with a finance-focused PDF called Market Corner, Sam with HustleCon events—before channeling insights into weekly email newsletters that US subscribers eagerly opened.

Scaling from 100K to 1M Subscribers

As The Hustle and Morning Brew raced toward the million-subscriber mark, both founders faced intense hustle. Alex juggled a Wall Street job by day and newsletter creation by night:

“I was working on Wall Street and doing the Brew from 7 PM to 11 PM, falling asleep with my laptop on my lap.”

Meanwhile, Sam relentlessly pursued ad deals. His first sale came after cold-emailing Chris Martinez at Wealthfront for $4,600 in 2016 [verify]. By year’s end, The Hustle generated around $400K in revenue with roughly 100K subscribers, while Morning Brew grew organically to 100K subs before investing heavily in ads the following year. Both teams discovered the power of paid acquisition—spending up to $500K per month on Facebook ads in 2018—and realized that well-timed ad spend could supercharge growth when paired with compelling content.

Lessons Learned in Financing and Team Building

Reflecting on early mistakes, Sam regrets raising too much capital too soon: “If I were starting today, I would not raise funding at all.” He advises founders to delay fundraising until they truly need working capital to cover cash-flow gaps. Alex takes a more moderate view: while Morning Brew did secure a $750K round, those funds enabled critical hires and investments in sales and content. Both emphasize:

• Raising as little as possible to maintain ownership and focus.
• Vetting investors carefully to avoid future conflicts.
• Codifying core values early—an ownership mentality and underdog spirit—to guide hiring and decision-making.

Building a capable team proved essential. Alex and Sam tapped “undiscovered talent” from nontraditional backgrounds, developing writers, marketers, and operators who thrived in a culture of high standards and constant feedback.

Content Quality: The Foundation of Growth

Content is not optional. Sam warns that those chasing 2017’s newsletter arbitrage miss today’s tougher economics: “People have to feel like they’re getting something valuable every time they open the email.” Both founders instituted rigorous content reviews, circling strong pieces and excising weak drafts to ensure only top-tier articles reached readers. Over time, Morning Brew and The Hustle refined their voices and formats to maintain engagement, proving that excellent content fuels subscriber retention, higher CPMs, and sustainable growth.

Navigating the COVID-19 Shock

When the pandemic hit in early 2020, both businesses faced immediate revenue declines as advertisers pulled back. Sam and Alex feared layoffs and even closure. They cut ad spend to zero overnight, then pivoted to short-form education products and online courses to shore up cash flow. One partnership—Morning Brew’s collaboration with Scott Galloway’s Section4—generated $300K in one month, buying critical runway. Events were canceled, but creative monetization and government relief funds kept both companies afloat until ad budgets rebounded later that year.

The Sale Process: Selling at Scale

By mid-2020, The Hustle and Morning Brew attracted acquisition interest. Alex recalls an 11-month negotiation with Axel Springer, enduring roller-coaster emotions from pandemic uncertainty to sudden revenue surges. He learned that selling a company brings intense stakeholder management: investors flip from urging a sale to arguing over purchase price, employees worry about equity dilution, and founders grapple with conflicting advice. Sam’s sale process at HubSpot was more abbreviated; he chose not to hire an investment banker to preserve control and minimize fees. Each founder emphasizes:

• Prepare for a sale as an emotional marathon, not a sprint.
• Align shareholder expectations early to avoid disputes.
• Understand incentives: acquirers focused on user growth may value subscribers more than profit.

Key Takeaways for Aspiring Entrepreneurs

As Sam and Alex reflect on years of newsletter entrepreneurship, several lessons stand out:

• Focus relentlessly on quality content before chasing growth hacks.
• Delay fundraising and maintain equity to maximize long-term upside.
• Hire for attitude and potential, not just pedigree.
• Cultivate an underdog spirit and ownership mentality company-wide.
• Be prepared to pivot—lifestyle events can evolve into media powerhouses.
• Approach sales with a clear strategy, managing investor and employee expectations.

Bold Actionable Takeaway: Invest your time in creating outstanding content first; subscribers follow value, and revenue follows subscribers.

Where to Play Next: Future Opportunities

Newsletter growth may be tougher now, but targeted niches remain ripe. Sam and Alex agree that hyper-focused media—vertical newsletters for specific industries like alternative investments or financial advisory—can command higher CPMs and unlock direct monetization (subscriptions, courses, events). Physical quarterly magazines or curated printed reports with industry rankings could revive the tactile appeal of premium content. Beyond newsletters, ambitious founders can mirror Overtime’s sports-media success by leveraging a loyal audience to challenge legacy incumbents.

Are you ready to start your newsletter or media venture? With a clear niche, relentless content quality, and a lean growth strategy, the next $100M+ business could be yours.