He Bought a Local Newspaper… Now He Makes $600K/YR - My First Million Recap

Podcast: My First Million

Published: 2025-06-27

Duration: 58 minutes

Summary

Small-town newspapers may not be glamorous, but they can be surprisingly lucrative and meaningful businesses. Buying one can generate strong cash flow, provide deep community impact, and offer a fulfilling career path, as highlighted by the example of a local paper generating $600K annually.

What Happened

The episode kicks off with a tweet from Matthew Prince, CEO of Cloudflare, who suggests that buying a small-town newspaper can be an incredibly rewarding career move. He argues that while these businesses often don’t make people billionaires, they offer substantial profits, such as one paper he owns that cash flowed $600,000 annually. The hosts dive into why many local papers are shutting down—not due to financial issues, but a lack of succession planning, as aging owners can’t find buyers.

Matthew Prince explains that small-town newspapers often have a monopoly on local advertising, with businesses like hospitals eager to advertise. The hosts highlight these newspapers as stable, cash-flowing businesses despite their small scale. Prince’s perspective resonates with the story of Rupert Murdoch, who started his media empire by buying a small paper at age 21. This example reinforces the idea that small, local ventures can be the foundation of something much larger.

Shaan shares his experience giving a talk at Berkeley, where he emphasized the concept of ‘starter businesses’ or ‘white belt businesses.’ He explains these as simple, manageable ventures for young entrepreneurs to gain experience. Owning a local newspaper is presented as an ideal candidate for such a starter business because of its profitability and ability to build community connections.

The conversation shifts to Steve Ballmer’s insights shared on the Acquired podcast. Ballmer recounts how Satya Nadella’s willingness to step aside and work under a more talented hire demonstrated the leadership qualities that eventually made him Microsoft’s CEO. This anecdote highlights the long-term value of humility and prioritizing company needs over ego.

Gary Vaynerchuk’s bullish optimism on nearly every major tech company is humorously critiqued. The hosts point out that while his enthusiasm is contagious, it underscores how difficult it can be to predict the next wave of business success. They also discuss Gary’s company, VaynerMedia, which has grown into a $300 million business by managing social media campaigns for major brands.

The hosts introduce Josh Kruger, the 32-year-old Democratic candidate for New York City mayor, whose innovative use of social media is shaking up traditional political marketing. One video, where he addresses “Halalflation” by interviewing street vendors, demonstrates how his raw, user-generated content style resonates with voters, especially younger ones. His charisma and storytelling abilities are emphasized as key factors in his rise.

Shaan and Sam debate the role of charisma in leadership and politics, with references to past presidents like Obama and JFK. They argue that likability and storytelling often outweigh policies when it comes to winning elections. The hosts also delve into how AI tools like 11 Labs could revolutionize political campaigns by making multilingual outreach more accessible.

The episode concludes with a discussion about stock-picking and the difficulty of identifying 50x growth companies. The hosts reflect on a viral tweet from 2021 that listed 20 companies with ‘50x potential,’ which ultimately performed poorly. The takeaway? While investing can be rewarding, it’s often better to focus on obvious trends and avoid speculative bets on unproven businesses.

Key Insights

• Many small-town newspapers generate significant cash flow, with one example making $600,000 per year, yet they struggle to survive because retiring owners often can’t find buyers—not because they aren’t profitable.
• Local newspapers hold a near-monopoly on small-town advertising, with businesses like hospitals willing to pay for the reach. This built-in demand makes them stable, cash-flowing businesses, even in an era dominated by digital media.
• ‘Starter businesses’ like owning a local newspaper let young entrepreneurs learn the ropes with less risk. They’re simple to manage, profitable, and provide real-world experience in running a company while building community connections.
• A tweet predicting 50x growth for 20 companies in 2021 fell flat, as most failed to deliver. The lesson: betting on obvious trends beats speculative picks, even when hype makes the latter feel irresistible.

Key Questions Answered

How can buying a small-town newspaper generate $600K annually?

Matthew Prince shares that small-town newspapers often have monopolies on local advertising, with businesses like hospitals eager to market through them. These papers are stable, cash-flowing businesses, with one he owns generating $600K annually.

What did Steve Ballmer say about Satya Nadella's leadership?

Steve Ballmer recounted how Satya Nadella suggested hiring someone more talented and working under them to benefit Microsoft. This act of humility and prioritization of company needs demonstrated the leadership qualities that led to his eventual role as CEO.

What makes Josh Kruger's political marketing strategy unique?

Josh Kruger uses raw, user-generated content styles, like man-on-the-street interviews, to connect with voters. His viral video addressing 'Halalflation' resonated particularly with younger audiences due to its authenticity and relatability.