Newsletter Coaching Session: Scaling Deep Dives Into a Newsletter Growth Engine

“$250k is when growth changes. It’s when you need systems. You usually can’t do it solo.”  — Matt Gira, The Quarter

Matt Gira joins Chenell & Dylan — in person — to share how he went from building underwater drones to launching The Quarter: a newsletter that deep dives into how founders grow bootstrapped businesses to $250K. This is an interview, but also an impromptu coaching session with Matt as we help him figure out how he can grow his newsletter faster and get it in front of the right audience.

We talk content strategy, growth experiments, and the surprising data he's uncovering along the way.

PS - Matt is not only an up-and-coming newsletter creator, he's also a member of the GIR Pro community 🔥
  • Why $250k is the key milestone for bootstrapped founders
  • How Matt turned a niche data set into a powerful newsletter growth lever
  • How he grew his newsletter to 1,200+ subscribers without chasing virality
  • Collaborations, events, and the tour that could 10x his reach
  • The power of being early, scrappy, and generous in your creator journey
  • How Matt reverse engineers founder journeys from YouTube to written content
  • The role of YouTube, LinkedIn, and in-person meetups in his growth flywheel
  • Strategies he’s testing now: content swaps, data licensing, services
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Thanks to Tim Forkin for editing these episodes.
Newsletter Coaching Session: Scaling Deep Dives Into a Newsletter Growth Engine
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