Geoff Sharpe isn't a journalist, but he’d figured out how to build a paying audience for local journalism.
He’s the founder of Lookout Media, a growing network of newsletters with four active publications across three cities: Ottawa Lookout, Van City Lookout, Yukon Lookout, and Capital Eats
Lookout is illustrating a sustainable model for journalism — readers will pay for real reporting if it feels relevant, consistent, and trustworthy.
In this episode:
📊 Building a local media business with 75% of revenue in subscriptions
💼 Applying nonprofit funding tactics to drive subscription revenue
🎯 Thinking of subscriber acquisition in terms of lifetime value
— Natalia Pérez-González, Assistant Editor
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00:00 Introducing Geoff Sharpe
01:40 Making $500K+ with paid subscriptions
07:16 Don't listen to your audience
12:00 The merging of editorial and business
16:20 Running a media company sustainably
21:01 Building trust through food
27:06 How to get people to pay for your content
37:43 What do people not pay for?
40:44 Don't scale too quickly
43:41 The difficulties of local newsletter ad sales
49:11 How to grow a local newsletter
52:40 A bullish and bearish take on local media
57:50 Best advice for entrepreneurs
🎧 If you prefer a podcast platform other than YouTube, we’re on Apple, Spotify, and all the rest.
Sometimes, you shouldn’t listen to your audience
Survey Geoff Sharpe’s readers and they'll tell you they want an “events and real estate listings” newsletter. Ask Geoff, and he’ll tell you that even though readers click on that content religiously, they won’t pay for it.
"If we followed what our audience wants, we would just be an events newsletter […] The job of journalists is to spark curiosity and interest in people — bring them towards things they might not necessarily know that they’re interested in.
This isn't about ignoring your audience entirely. Lookout Media runs constant surveys and monitors engagement religiously. It's about understanding the difference between what people say they want and what they'll actually pay for.
Geoff, a marketing agency owner who learned membership conversion working with nonprofits, has an instinct for these patterns. He treats local news like a donor-funded mission, and runs the business using the Entrepreneurial Operating System (EOS) — quarterly goals, clear values, defined roles. Lookout Media is betting on what can’t be commodified: trust, consistency, and community presence.
By the numbers
Subscribers: Over 100,000 total subscribers. 3,000 paid subscribers across all newsletters (up from 2,500 earlier this year)
Annual revenue: Approaching $500K (stretch goal for 2025)
A December membership drive generates 25% of net-new annual subscription revenue
Team: 1 journalist per city, food writers in Ottawa and Vancouver, and a newly hired salesperson
Annual membership pricing: $125 in Ottawa, $99 in Vancouver
18 months to profitability in Ottawa (though Geoff still doesn't pay himself)
What’s working: Quality journalism. Local development investigations and neighborhood-level reporting drive subscriptions, even with lower engagement.
Geoff reinvests every dollar made through Lookout Media into hiring journalists and sustains himself through his marketing agency. Growth remains conservative, with nine to twelve months of runway before any hiring, and no venture funding. In the next four years, he aims to launch neighborhood-specific newsletters in five to six more cities, establishing Lookout Media as the most trusted news brand in every market they enter.
"Execution is like 80% of the game. Everyone has a million ideas, but if you can't execute on it well, it's just not gonna go anywhere."
Geoff’s projected futures for local news:
Sustainable. Reporters in city halls, critics who actually visit restaurants three times, familiar faces at community events.
Automated. Companies like 6AM City scaling AI-generated “good news” across hundreds of cities, winning on ad arbitrage, not reporting.
“If it becomes a game of who can build the biggest audience to deliver positive news summaries, editorial stops mattering — it’s just whoever has the most money.”
Connect with Geoff on LinkedIn.
Learn more about Lookout Media.
How to convert free readers into paying subscribers
How do you convert free subscribers to paying subscribers? Take tactics from nonprofit fundraising. Geoff applies his experience in that realm to Lookout Media; most of the business’ conversion comes through subscribers drives.
There are two typical reasons people pay for independent media:
To access information they can't get elsewhere
To support a mission they believe in.
The most successful subscription products play off both motivations.
Optimize acquisition for lifetime value (LTV) over vanity metrics
Your cheapest leads are probably your worst leads. For Geoff, Meta ads based around food content brought in subscribers at around $0.60–$0.70 CAD each — half the cost of his news-focused ads. But, tracking those food-ad-leads through beehiiv’s engagement tools, he rarely saw them convert to paid subscriptions.
This applies to any newsletter niche. Whatever content type drives your cheapest acquisition probably attracts browsers, not buyers.
A finance newsletter could acquire readers cheaply through meme content about money, but may be better served long-term investing in analytical content that will attract subscribers willing to pay.
Calculate what a paying subscriber is actually worth to you over 12 months. Then work backward to determine what you can afford to pay to acquire the right readers.
Deploy selective paywalls that demonstrate value
Lookout Media strategically paywalls a few stories monthly — investigations requiring serious reporting resources, neighborhood-level analyses readers can't get elsewhere, anything demonstrating why professional journalism costs money.
Everything else stays free. Breaking news, community events, most restaurant reviews — the content that builds trust and proves competence remains accessible. The paywall appears only on work that requires significant investment and delivers irreplaceable value.
"Grow organically until you can really figure out who you're talking to, what your voice is, and build that trust. It's really hard to start a newsletter and start monetizing on day one."
Choose your business model, then optimize everything around it
Every decision at Lookout Media is shaped by its membership-funded model: content strategy, acquisition targeting, pricing, and paywall placement.
"If I just said we're running an impression-based business that's going to deliver ads, I would optimize every other downstream decision completely differently.”
Each model requires fundamentally different strategies. Trying to optimize for all of them means optimizing for none.
Once you pick your primary business model, ask whether each decision serves that model or just produces vanity metrics. Your choice might be advertising (maximize reach), consulting pipeline (optimize for positioning), or subscriptions (prioritize conversion). The specific model matters less than committing to one and aligning everything around it.
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