The Not Boring Flywheel
Turn a niche audience into a self-reinforcing engine of content, sponsors, and venture deals
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 70%
The Not Boring Flywheel is the mental model Packy McCormick uses to explain how a single newsletter grew into a media-and-investment empire without a large team. At the center sits a specific, high-value audience — founders, operators, and decision-makers — not just a large subscriber count. That audience is earned through distinctive, well-researched, entertaining content published on a consistent cadence. The audience in turn attracts sponsors willing to pay for access and founders willing to give investment allocation, because being read by that specific audience is worth more than raw reach. Revenue and relationships from sponsors and founders fund more time and credibility to produce content, which grows the audience further, and the cycle repeats. The key insight is that audience composition, not size, is what makes each part of the loop reinforce the next.
Origin
Emerged organically as Packy McCormick grew Not Boring from a personal newsletter into a media company plus venture fund, without ever planning the structure in advance.
Core principles
- 01Audience quality (who is reading) matters more than audience size for compounding value.
- 02Content, audience, and investing must be mutually reinforcing, not separate business lines.
- 03Every additional business line should feed back into the core content, not dilute it.
- 04Growth compounds only if the writer avoids getting 'greedy' and keeps the content bar high.
How to run it
- 1
Cultivate a Specific, Valuable Audience
Focus on attracting readers who are founders, operators, or decision-makers rather than chasing raw subscriber counts, since this group is what makes sponsors and founders want in.
Pro tip Track who reads you, not just how many.
- 2
Publish Distinctive, High-Effort Content on a Cadence
Write in an authentic voice combining research and entertainment consistently (e.g., twice weekly) so the audience trusts the content enough to act on it.
- 3
Let Sponsors In With Full Transparency
Offer sponsored deep dives at a price that reflects genuine access to the audience, always disclosing the arrangement upfront.
- 4
Use Content-Driven Trust to Source Investment Deals
Let founders come to you because they've read and valued your writing, rather than pitching cold — this becomes your deal flow for a venture fund.
- 5
Reinvest Revenue and Relationships Into More/Better Content
Use sponsorship and investment income to buy time to keep producing distinctive content, which grows the audience and restarts the loop.
Watch out Do not scale by hiring ghostwriters or diluting the voice — that breaks the loop's authenticity.
In the wild
When Ramp raised at a $1.1B and $1.6B valuation in the same round, CEO Eric gave Packy full access to the cap table construction and deal timeline. Packy used that access to write one of Not Boring's most-referenced sponsored pieces.
→ The piece became the gold-standard example sponsors point to when negotiating access, reinforcing the flywheel's sponsor side.
Nick Abazid pitched Packy on writing a sponsored piece about Main Street's tax-credit product for founders, one of the earliest tests of paid content on Not Boring.
→ The post filled up the rest of 2020's sponsorship slots after Packy tweeted the resulting media kit, kicking off the revenue side of the flywheel.
Common mistakes
Optimizing for reach instead of relevance
A bigger but less relevant audience doesn't strengthen the flywheel — sponsors and founders pay for access to the right readers, not just more readers.
Getting greedy by adding unrelated revenue lines
Adding merchandise or unrelated products dilutes the core content and breaks the audience's trust in why they subscribe.
Is it for you?
Best for
Solo creators or small teams building a content-driven business that wants to monetize via sponsorship and/or investing
Not ideal for
Teams wanting to scale headcount quickly or build a broad mass-market audience
From the transcript
“i think it's really just kind of the alignment between the content the particular people who are in the audience uh and then the investing…”
“this works if i don't get greedy and this stops working if i get greedy”
From the episode
Not Boring (with Packy McCormick)