- Grow 📧 Monetize
- Posts
- 📩 Monetization Masterclass
Jesse Watkins, co-founder of Who Sponsors Stuff and co-creator of The Newsletter Conference, sat down with me to share a clear, practical path for turning a newsletter into a steady revenue engine.
Jesse has worked with publishers of many sizes, and his simple message is this, treat sponsorships like a craft. That means consistent publishing, smart positioning, and a tight fit between your editorial voice and any sponsor you bring in. If you want a deeper dive, watch our full conversation with Jesse in this episode of Audience Bridge Insights, where we break down pricing models, pipeline building, and growth moves.
In partnership with
How 433 Investors Unlocked 400X Return Potential
Institutional investors back startups to unlock outsized returns. Regular investors have to wait. But not anymore. Thanks to regulatory updates, some companies are doing things differently.
Take Revolut. In 2016, 433 regular people invested an average of $2,730. Today? They got a 400X buyout offer from the company, as Revolut’s valuation increased 89,900% in the same timeframe.
Founded by a former Zillow exec, Pacaso’s co-ownership tech reshapes the $1.3T vacation home market. They’ve earned $110M+ in gross profit to date, including 41% YoY growth in 2024 alone. They even reserved the Nasdaq ticker PCSO.
The same institutional investors behind Uber, Venmo, and eBay backed Pacaso. And you can join them. But not for long. Pacaso’s investment opportunity ends September 18.
Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.
*Ad
Sponsorships Are Earned, Not Installed
There is no plug and play switch for sponsorship revenue. You need a clear media kit, a clean booking process, dependable deadlines, and a feedback loop with brands. Treat every placement like a feature story, not a banner. When you do, brands stick around, and readers stay engaged because the message feels like part of the show.
Voice First, Placement Second
Strong deals begin with brand fit. Your audience trusts your tone and judgment, so every paid message should sound like you wrote it. The sponsor provides the brief, but you hold the pen. If the partner wants copy that clashes with your style, pass. That single decision protects reader trust, which is the root of long-term revenue.
Why Flat-Fee Pricing Keeps You In Control
CPM math can be useful as a sanity check, yet it often undervalues the years you have put into building your list and keeping readers. With a flat-fee structure, you price for access to your audience and the work required to craft a message that lands. It is simple to sell, easier to forecast, and it keeps leverage on your side during renewals. For a straight comparison of common ad models, this guide lays out the pros and cons in plain language Flat-fee vs CPM, explained in plain English.
It’s go-time for holiday campaigns
Roku Ads Manager makes it easy to extend your Q4 campaign to performance CTV.
You can:
Easily launch self-serve CTV ads
Repurpose your social content for TV
Drive purchases directly on-screen with shoppable ads
A/B test to discover your most effective offers
The holidays only come once a year. Get started now with a $500 ad credit when you spend your first $500 today with code: ROKUADS500. Terms apply.
*Ad
Direct Relationships Beat Reliance On Middlemen
Networks and agencies can help fill unused spots, but the strongest programs come from direct brand relationships. When you manage your own pipeline, you control creative quality, timelines, and pricing. A useful place to research active newsletter advertisers is Who Sponsors Stuff, which tracks brands buying across the space See what Who Sponsors Stuff tracks across the ad market.
Sold Out Inventory Is A Signal, Not A Ceiling
When your placements are fully booked, you have choices. Raise pricing for premium positions like above-the-fold features or lead slots. Build add-ons such as sponsored sections, category guides, or a monthly roundup issue. Spin up adjacent products like a job board or a targeted micro-edition for a specific segment. Whatever you add, keep the main product tight and reliable, then layer extras with care.
A Simple Weekly Workflow
Prospect list building, outbound, calls, and follow-ups belong on your calendar just like writing. Monday, refresh your target list and send introductions. Tuesday, write the ad copy for future spots. Wednesday, hold partner calls. Thursday, finalize next week’s creative and placements. Friday, review results and send a short recap to each sponsor with what you saw and what you will try next time. Rinse and repeat. This rhythm builds predictability on both sides.
Your First Pricing Ladder
Start with one flagship placement at a premium price. Add a secondary placement at a lower price point that carries shorter copy. Create a bundled option that combines newsletter plus one social post or a brief site feature. Keep the menu short, three clear choices at most, and review pricing every quarter based on demand and outcomes.
Learn From The Operators
Jesse and his co-founder also host The Newsletter Conference, where operators swap tactics on sponsorships, content, and growth. Skim the agenda to spot panels that map to your next move and note who is speaking, then reach out for a quick intro after you attend Peek at The Newsletter Conference agenda.
Final Thought
Sponsorships are not a shortcut. They are a system. Lead with reader trust, keep your voice at the center, choose flat-fee pricing to hold leverage, and build direct relationships that last. Do these basics well, and the business side starts to feel as repeatable as your writing habit.
AI You’ll Actually Understand
Cut through the noise. The AI Report makes AI clear, practical, and useful—without needing a technical background.
Join 400,000+ professionals mastering AI in minutes a day.
Stay informed. Stay ahead.
No fluff—just results.
*Ad