👋 If you’re a newsletter or podcast that charges $5k+ per ad, I have a treat for you! Just reply here or nudge me on LinkedIn.

Mysterious intros aside, let’s dive in! 🚀

Four Paths to Enterprise Brand Dollars

Most media startups chase enterprise brand budgets the same way: build audience, prove performance, wait for the brand dollars to magically appear.

They don't.

Enterprise brand budgets operate on relationships, trust signals, and access. The challenge? Building these traditionally takes 3-5 years of consistent revenue and market presence.

But some media companies crack the code faster. Here are the four proven paths to enterprise dollars that don't require you to age like fine wine first.

💰 Own a High-Value & Underserved Niche

(And go to trade shows)

Dominate an underserved audience that enterprises desperately want to reach, then build relationships where they already gather.

Example: Payload, an aerospace and defense newsletter, didn't wait for Lockheed Martin to find them. They went to trade shows where defense contractors actually spend time.

Brian from Payload has previously walked through his exact event strategy for you here

Why this works: Some B2B niches still have terrible reach problems. Defense contractors can't efficiently target engineers and procurement officers through Meta ads. A focused newsletter with 15K subscribers in aerospace is worth more to them than a general business publication with 500K.

The trade show component is critical. Enterprise marketers/buyers in specialised industries already attend 5-10 events annually, which cost $50k each. Show up, have real conversations, build actual relationships. It's old school, but it works.

This only works if your niche is genuinely underserved and high-value. A newsletter for "professionals interested in productivity" isn't going to cut it. You need defensibility. Pun intended.

❤️ Launch With Established Relationships

Start your media company with co-founders who already have decade-plus relationships with media agencies and enterprise marketing decision-makers.

The Example: Semafor was founded by people with extensive connections to agencies and brands (so I hear). Day one, they had feet in doors.

A significant portion of enterprise brand budgets still flows through relationships and schmoozing. This isn't changing anytime soon.

If you're founding a media company and trying to crack enterprise budgets, having a co-founder with an existing rolodex of agency contacts is like starting Monopoly with hotels already on Boardwalk (or Mayfair if your British). Not fair, incredibly effective.

Obviously, most founders don't have a former Condé Nast executive or agency SVP waiting in the wings.

🧳 Get Acquired by Legacy Media

Build a media property with strong metrics, then get acquired by a larger publisher that already has enterprise relationships.

Plenty of examples here, Morning Brew got acquired by Business Insider (Axel Springer), and overnight, you could see sponsorships spike from BMW, Heineken, Amazon, and other enterprise brands that would've taken years to access independently.

Why acquisitions unlock brand budgets: Large media organizations have existing agency relationships, approved vendor status, and the trust signals (read: boring corporate credentials) that procurement departments require. Your scrappy startup might have better engagement, but enterprises need to see "established media partner" on the paperwork.

The catch: "Just get acquired" isn't a strategy. But if you're building with this path in mind, focus on building a business that will get bought.

💦 Make a Splash

Probably the most accessible way. Create a high-profile event or media product that builds instant credibility and gets you in the room with enterprise brands.

I was a sales manager at Finimize, we launched the Modern Investor Summit in 2021, a new retail investing event.

We invested a lot of time to grab top-tier speakers like Mark Cuban and Ray Dalio. The event itself became a media property, but more importantly, it built trust and opened doors with enterprise financial services brands for future events and other Finimize initiatives.

This works because events, especially large well-timed events with great speakers, signal legitimacy in a way that newsletters can't. People notice, so do enterprise brands.

This requires significant upfront investment and strong enough connections to land marquee speakers. Although, Finimize did scrap around to make those connections from scratch. Plus, the Summit became it’s own profit-making media property too.

So it CAN be a win-win if executed well.

Enterprise brand dollars don't flow to media companies just because they have large audiences. They flow through relationships, trust, strategic positioning, and luck.

P.S. Need help selling more sponsorships? My agency Ad Sales as a Service helps media companies do just that.