Why Every City Needs a Jas Singh
What if you could turn your city’s untapped attention into a thriving business?
That’s exactly what Jas Singh did. In just one year, he turned Winnipeg Digest into a must-follow brand across newsletters, Instagram, and in-person events — all while flying mostly solo. In this episode, Jas breaks down how he built a 25,000-subscriber email list, grew to 60K+ social followers, and generated over $100K in revenue, all by mastering the local attention game.
If you're trying to grow a local media brand or monetize a regional audience, this is the masterclass you didn’t know you needed. Jas doesn’t just talk theory — he shares the gritty tactics, strategic pivots, and even pricing models that have worked for him. Whether you’re just starting or looking to scale, this is packed with gold.
Treat Instagram Like Your Funnel, Not Your Endgame
Social is your billboard — your newsletter is your product.
Jas views Instagram as a top-of-funnel channel that builds brand awareness, credibility, and trust. It’s not where conversions happen — but it’s what warms people up to eventually subscribe.
“When people see your brand on social and get value upfront, they’re more likely to convert when they see your ads.”
Instagram also expands his sponsorship packages: instead of just offering newsletter slots, Jas can now add video content, story posts, and reels. This multiplies revenue opportunities without requiring new clients.
Use reels to grow in the beginning — they’re what drive discovery.
Shift to carousels later to keep your audience engaged.
Repurpose local updates and community news to build trust.
Keep It Simple, Keep It Clean
A cluttered landing page costs you real money.
Early on, Jas made the mistake of sending Facebook ad traffic to a busy page with links, buttons, and distractions. Once he stripped everything down to a simple email form, cost-per-acquisition dropped by half.
“Just having that ‘read more’ button on Beehive doubled my costs. Once I removed it, everything changed.”
This micro-optimization tip alone can save you thousands — and it’s the kind of insight Jas is full of.
Sell Sponsorships with Exclusivity and Confidence
Forget one-off ads — build long-term deals.
Jas doesn’t chase one-time advertisers. Instead, he sells $10,000 annual sponsorships that include:
10 newsletter placements
1 Instagram reel
Category exclusivity (only one dentist, one landscaper, etc.)
This model gives clients predictable value and makes Jas’s business more stable. He uses a comparison chart to show how his offer stacks up to Facebook or radio ads, and always emphasizes the unique ROI of exclusivity.
“Your biggest asset is that you can tell a brand they’ll be the only one in their niche.”
Turn IRL Events into Your Real-World Megaphone
Digital audiences are great. But when people show up in person, that’s brand power.
Jas is now expanding into summer markets — think farmer's markets with a twist. They’re free for attendees, but vendors pay to participate. He partnered with a local events company, takes a percentage of profits, and handles all marketing through his existing channels.
“It’s like I became their fractional CMO — and now they’re doing five markets instead of one.”
This real-world exposure creates brand association that lives beyond the inbox or feed.
Monetization Isn’t Optional — It’s the Game
You don’t get to build a brand if you can’t pay the bills.
Jas is upfront about it: you have to learn how to sell. That might mean sending five cold emails a day. It might mean grabbing coffee with a local spa. But you have to do it. His advice?
Prioritize high-LTV niches: dental, home services, medical spas.
Use exclusivity to drive urgency.
Don’t be afraid to say, “we’re talking to three others in your niche.”
This is how you go from being a hobbyist to being the local media company.
Think Long-Term: From Cashflow to Hold Co
Media isn’t the end — it’s the launchpad.
Jas sees the local media business as a platform. Once he maxes out revenue ($500K–700K/year), he plans to use the trust and audience he’s built to start or invest in local businesses.
“Why keep selling ads when you can own the business you're promoting?”
Imagine having the top local newsletter and social account — then using it to grow an HVAC or landscaping business you partly own. That’s where Jas is headed.
Bringing It All Together
Jas Singh isn’t just building a newsletter — he’s building a citywide brand.
Through sharp growth tactics, strategic partnerships, and real-world value creation, he’s crafted a blueprint others can follow. Instagram brings the reach. The newsletter drives conversions. Events bring it to life. Sponsorships pay the bills. And all of it builds a trusted brand.
If you’re trying to win local, this isn’t optional anymore — this is the playbook.
“You have maybe a year or two before AI makes this easy. By then, the winners will already have the audience.”
How I Can Help You Succeed
Before we dive into this week's insights, I want to make sure you know about all the resources available to support your local newsletter journey:
🎙️ The Podcast - Deep-dive conversations with successful newsletter operators sharing their playbooks and lessons learned | Link
📧 This Weekly Newsletter - Quick, actionable tips delivered straight to your inbox every week | Link
🧠 1:1 Consulting - Personalized guidance tailored to your specific newsletter challenges Link
🚀 Launch Accelerator - A structured program to help you go from idea to profitable newsletter in record time | Link
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