7 mins

Friday Feature: Lookout Media

How to sustainably grow and scale a local newsletter.

Sameer Ansari

If you think local media needs to rely 100% on ad revenue to survive… 

You’d be mistaken.

Geoff Sharpe has figured out a sustainable local media business model where advertisements make up only ¼ of revenues.  

Not only that, Geoff and his team at Lookout Media have scaled the model from Canada’s capital city of Ottawa to the larger, west coast city of Vancouver—and into different niches like food & experience. 

In this week’s Friday Feature, you’ll learn how Geoff’s doing it, and how you can too—whether you’re building a media business locally or online.

Let’s dive in!

#1 - Quality content first

A common trap local newsletter operators fall into is believing they can build a substantial business by sharing links to local news & events.

That might get you started, but you won’t build a competitive edge.

Geoff saw the opportunity to create something “better” and took the opposite approach to content.

🧐 Why it’s awesome

→ Differentiation: Providing value through detailed commentary on how the local events will affect the readers will help you distinguish and make your newsletter more compelling to your readers.

→ Building community: Sharing “better” content that truly represents a city will build trust, loyalty, and community.

🙋 How Lookout Media does it

What Geoff does to stand out from other local media:

→ Competitor analysis: He reads competitors’ newsletters to know what they're doing. Then he does it 10x better (longer content, more researched, and different content structure, etc) — he follows a different approach to content (like with their ​Dining Guides​).

→ Knowing your user: Geoff talks with locals to understand their pain points, likes/dislikes, interests, content preferences, and more.

→ Creating a personal connectionbetween the writer and readers: The Lookout newsletters are like a local friend sharing local news and events with the residents. They integrate the writer’s personality (your local friend) with the brand. It creates a unique voice that resonates with readers.

→ Content differentiation: You won’t find Geoff’s team just regurgitating the news. Instead, he “gives people insights about what it means for the city’s future and how to understand that in that context.”

Here’s an ​example​:

Another example is that instead of writing yet another “10 pizza places to visit,” the Lookout team visits the pizza places, tastes the pizza, talks with the owner, and takes reviews from locals to write a detailed pizza review.

✏️Steal this for your newsletter​

Follow a similar approach to Geoff. 

→ Understand your ideal reader: For a local newsletter, find out what’s important to the locals, their favorite events, the news they care about, and other important details. For an online newsletter, do the same about your niche or industry.

→ Hire local writers (like Geoff): They’ll know the city, the residents’ attitude, and general vibe. If nothing else, they are able to have their fingers on the pulse living in the city they write about. A (potential) bonus: they’re more likely to take passion and pride in writing about where they live.

→ Get involved in the community: Ryan Sneddon writes a local newsletter. He ​shared​ with us that he attends local events and meets with the residents to strengthen his relationship with the locals. This has bolstered his—and his newsletter’s—reputations.

#2 - Value-first monetization

Most local newsletters rely almost exclusively on ads & sponsorship revenue.

Not Lookout Media.

Geoff and his team have taken a page (not literally) out of the print media business model and offer a subscription option.

🧐 Why it’s awesome

→ Diversification: If one revenue source (ad sponsorships) struggles, others (subscriptions) can fill that gap.

→ Recurring revenue: Paid newsletter subscriptions are either billed monthly or annually. So, as long as you provide valuable content, readers will renew their subscriptions.

🙋 How Lookout Media does it

Here’s the revenue diversification of Lookout Media:

→ Subscriptions: 2000 readers pay for exclusive content such as deeper city-hall reporting, in-depth food reviews, and more. This makes up 75% of Lookout Media’s total revenue.

→ Ads: Sponsorships drive the remaining 25% of revenue. This includes revenue from paid recommendations via SparkLoop’s ​Upscribe​ widget. That paid recommendations revenue helps subsidize Lookout Media's FB ad spend. They reliably recoup a percentage of their CPA every week thanks to SparkLoop and paid recommendations.

Another potential revenue driver (similar to what ​Ryan​ shared) leveraging an engaged community to spin out potential companies. Geoff offers examples like an event listing board, job board, and real estate opportunities.

✏️ Steal this for your newsletter

Here are a few value-first monetization strategies:

→ Monetize your expertise: ​Katelyn Bourgoin​ turned her experience running and selling multiple businesses into her ​Why We Buy​ newsletter. She leverages her newsletter audience to consult other founders through ​strategy calls​ and ​courses​

→ Corporate Training: Kat Norton (famously known as Miss Excel) ​provides​ corporate teams with “custom live Excel training events and online courses in Microsoft Office and Google Suite.” She also does keynote speeches.

→ Launch a business/service: ​Michael Houck​ launched Megaphone to help fellow founders and creators grow on social media. Trung Phan did the same by launching Bearly, an AI software.

→ Start a fund: Because creators like ​Ben​ and ​Packy​ are deeply involved in their space, they get access to deal flow before many others. So they launched their investing syndicates.

→ Master paid subscriptions: ​Michael Houck​ and ​Eric Lam​ shared their secrets of converting free subscribers into paid subscribers. Alternatively, here’s the ultimate ​guide​ to paid subscription growth.

→ Partnerships: A local newsletter can partner with local restaurants, shops, or service providers to offer exclusive offers and discounts in exchange for a fee or commission.

You can also partner with e-commerce companies, industry experts, and event organizers to sell their products, courses, and other offerings. You can also partner with companies to create sponsored content.

#3 - Repackaging success

Geoff and his co-founder began by building out and scaling the ​Ottawa Lookout​ newsletter. Once they had a recipe they felt worked, they launched ​Vancity Lookout ​in Vancouver.

(Vancouver is a very different market on the other side of the country.)

And just like in Ottawa, Vancity Lookout has been a success.

The result assured them their local newsletter model works giving them confidence to expand to other cities.

🧐 Why it’s awesome

→ Efficiency: leverage existing operational know-how and save time, money, and effort.

→ Increased revenue: More cities or more verticals. Morning Brew strategically expanded into other verticals such as tech, IT, and HR helping them attract a larger audience and opening up additional revenue streams (ie. more advertising partnerships, sponsored content, merch, in-person events, and courses).

🙋 How Lookout Media does it

→ Choose a location: Two things helped Geoff select Vancouver as his next local newsletter market: he knew about the city and its people + he realized the residents wanted to read certain content that existing newsletters didn’t provide.

→ Unique Selling Proposition: Geoff did in-depth reporting and original research to distinguish from other local media.

→ High editorial standards: Geoff gives every writer templates with information on the city, its audience, and writing style to create content that resonates with the local community.

→ Focus on retention: Since local newsletter growth is capped, Geoff focused less on growth (after a certain point) and more on reader retention. For example, he doubled down on unique content, a good onboarding series, audience segmentation, surveys to better serve the reader’s needs better.

→ Expansion to other verticals: Geoff (and his co-founder) started a separate newsletter on ​food​ for Ottawa locals apart from their ​main​ newsletter that talks about daily news and events. The idea was to serve the underserved food niche the locals wanted to read more about.

✏️ Steal this for your newsletter

→ Be strict in picking the city: Doing this one your own? Then choose a city/location you know the region and its people well. You should know their needs, problems they’re looking to solve, culture, inside jokes, and more. Alternatively, hire writers who check all those boxes.

→ Differentiate your content: Do content ​better or do it differently​.

→ Get your initial subscribers: Run FB ads or promote your newsletter in local FB/Reddit groups to attract initial subscribers.

→ Strategic expansion: Consider four factors to expand into new verticals:

  • audience interest
  • market trends and size
  • content-fit with the original newsletter
  • and monetization opportunities.

For example, Morning Brew ​ventured​ into the retail niche because it was “a big enough space to grow an audience, but also a niche enough space to go deep in areas and trends.” They tested the retail newsletter with a few readers and received encouraging responses. It also provided monetization opportunities like cross-selling ads. So, they launched the vertical.

Adding it up…

An impressive factor in all of this: Geoff Sharpe is still running Lookout Media on a part-time basis—and still growing and expanding.

The goal is to focus full-time on Lookout Media by the end of 2024.

His next goal is to hire writers to launch in other cities. But he’s also focused on doing it sustainably.

Here are 3 things to do next:

  1. ​Check out Lookout Media’s newsletters…
    1. ​Vancity Lookout → ​
    2. ​Ottawa Lookout →​
    3. ​Capital Eats →  ​
  2. Check out our whole conversation with Geoff Sharpe…
    1. ​Video →​
    2. ​Audio →​

Give us your take: what newsletter is doing something different and innovative we should feature next? Maybe it's yours... EMAIL US and let me know!

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