Not Boring: When Writing Itself Becomes the Deal Flow

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Packy McCormick spent six years turning a newsletter with a few hundred readers into a flywheel spanning media and investing. He had never founded a company, had no technical background, and had zero VC experience. His starting point was his mother-in-law's basement, his wife expecting their first child, fresh off leaving a startup that was running out of runway.

Background: An Investment Banker Turned Startup Operator

Packy McCormick graduated from Duke University with a B.A. in Economics in 2009 and joined Bank of America Merrill Lynch as an investment banking analyst, spending four years on M&A deals.

In 2013 he jumped into the startup world, joining Breather — a shared workspace startup — as General Manager of NYC. Over six years he rose to VP of Experience, managing a team of roughly 150 people across operations, design, customer care, real estate, and field ops. He lived through the full lifecycle of a venture-backed company: early-stage sprint, Series C fundraising, and a leadership shakeup.

In October 2019, new management came in with a direction he disagreed with. He left.

After Breather, he enrolled in David Perell's Write of Passage course. He had always been a fan of Bill Simmons — the sportswriter who rewrote the genre by weaving in pop culture and personal takes. Packy felt business and tech writing needed the same treatment: opinionated, fun, unpretentious.

During the course, he started a newsletter called Per My Last Email and published 44 editions.

From Social Club to Newsletter

In January 2020, Packy founded the Not Boring Club — an in-person social club in New York built around dinner parties and trivia nights. The idea was to bring interesting people together.

Two months later, COVID-19 locked New York down. A club whose entire value proposition was meeting in person instantly lost its reason to exist.

On April 2, 2020, Packy merged the newsletter from Write of Passage with the club and renamed everything Not Boring. It was a survival pivot: if he couldn't gather interesting people in a room, he'd gather them on a page.

Growth Timeline

From 600 to 100,000 in under two years — and the steepest part of the growth curve coincided with his essays getting longer and deeper. As he put it: "I stopped worrying about what I thought would work, and started following my gut."

Content Strategy: Long-Form Analysis, Not Curation

Not Boring occupies a completely different position from the other newsletters in this series. Daily Dose writes 150-word posts. TLDR does 5-minute summaries. Morning Brew delivers morning news bites. Packy writes 5,000 to 10,000+ word essays.

He publishes twice a week, typically Tuesday and Thursday, in three formats:

Trend analysis essays. Deep structural breakdowns of an industry or technology trend. One of his most famous early pieces was a two-part Tencent analysis that racked up over 100,000 views when he had only a few thousand subscribers.

Company deep dives. A single company dissected across business model, competitive landscape, financial structure, and risk factors. These pieces later became his core tool for investment decisions.

Sponsored deep dives. Unlike the typical newsletter ad insert, Not Boring's sponsored essays are full company analyses — the good, the bad, and the ugly. Packy's rule: sponsors are buying his time to write a thorough analysis, not buying a puff piece. One portfolio company reported that 75% of its commercial inbound and 50% of its customers traced back to their Not Boring deep dive.

His writing style is what makes it all work: complex business logic delivered in a conversational tone, laced with pop-culture analogies and precisely paced paragraphs. Readers never feel like they're reading an investment memo, even though the information density rivals one.

Business Model: The Sponsorship + Venture Fund Flywheel

Packy decided early on to keep the newsletter free rather than go paid. His math: at Not Boring's growth rate, the scale advantages of free distribution would make sponsorship revenue far exceed what a paywall could generate. In hindsight, he was right.

Sponsorships are the primary revenue driver:

• Early rates (at ~36K subscribers): Monday essays at $5,000, Thursday essays from $3,000
• Sponsored deep dives: $20,000+ per piece, 1–2 per month
• Rates scaled proportionally with subscriber growth
• Annual revenue went from $50K in 2020 to $1M in 2021 to a steady $3M+ today

Not Boring Capital is what makes this model truly unique:

Fund I performance: 1.31x Gross MOIC, 17.5% Gross IRR. Out of 207 portfolio companies across Funds I and II, only 4 shut down — $270K in losses, or 0.69% of deployed capital. The standout: a $250K investment that grew to $3.8M, a 15x return.

The most notable portfolio company is Ramp — the corporate spend management platform. Packy was introduced to co-founder Eric Glyman in September 2020 and invested early. Ramp went on to become the fastest company in NYC history to hit a $1B valuation and is currently valued at over $8 billion with $100M+ in annual revenue.

How the flywheel works:

1. Write high-quality deep analysis → attract readers
2. Readers include founders, investors, and tech executives
3. Founders read the analysis, realize Packy understands their space → reach out for investment
4. Investments yield deeper industry insight → fuel better analysis
5. Sponsors see the reader quality → pay higher rates
6. Some founders even say they decided to start their company after reading Not Boring

This isn't "newsletter writer moonlighting as an angel investor." Writing itself became the deal flow pipeline — deep-dive essays double as due diligence, the subscriber base serves as an LP pool, and brand visibility is the weapon for winning allocation.

Other revenue streams:

• Not Boring Syndicate (AngelList): lets readers co-invest; Packy takes ~10% of profits
• Talent Collective: a job board generating ~$1,100/month (higher during hiring seasons)

Three Lessons He Has Shared

Radical transparency is the best growth engine. From the start, Packy publicly shared subscriber counts, revenue goals, and sponsorship rates — he even posted his sponsor deck on Twitter. Counterintuitively, this attracted more sponsors because they could see the numbers and pricing logic for themselves.

Format choice constrains your scaling path. The 5,000–10,000 word long-form essay is his moat, but it's also his ceiling. He can't hire writers the way TLDR does — the style is too personal. Fund III brought on team members (Elliot Hershberg for biotech, Rahul Rana for deep tech analysis), but the core essays are still his to write.

Small funds have structural advantages. A solo GP with a small team can make weirder, riskier bets — no investment committee to convince when backing a synthetic biology startup. Each fund backs 30–100 companies, so any single loss is survivable, but one Ramp can return the fund several times over.

The Bigger Picture

Not Boring is the least replicable case in this series. The other newsletters' monetization paths — advertising, paid subscriptions, courses — have proven templates across different verticals and scales. But the "writing → venture fund" path has very specific prerequisites:

First, you have to be writing business analysis, not technical tutorials or news curation. Only business analysis simultaneously attracts founders and investors, letting writing directly convert into deal flow.

Second, you need a finance or banking background. Packy spent four years doing M&A at Merrill Lynch and six years running operations at Breather. His eye for evaluating companies wasn't trained by the newsletter — it was honed over a decade of deals and operations.

Third, timing: the 2020–2021 venture market was extraordinarily active, making it easier for a newcomer with an audience and industry connections to win allocation. That window doesn't stay open forever.

But the most important takeaway from this case isn't its lack of replicability — it's the underlying principle it reveals: a newsletter is not just a content product; it's a trust asset. When you consistently produce deep, honest, opinionated content, you're not just accumulating subscribers — you're accumulating people who trust your judgment. Packy converted that trust into investment allocation and LP capital.

For most creators, this path is too narrow. But it serves as a reminder: format and monetization are not fixed pairings. If your readership has sufficient trust density, the monetization path can be far less conventional than you might imagine.

References

• Not Boring
• Introducing Not Boring Capital (Packy McCormick)
• Not Boring Capital: 2 Fund, 2 Boring (Fund II announcement)
• Announcing Not Boring Capital Fund III
• How Packy McCormick Makes $3.5 Million with 180k Subscribers (Growth In Reverse)
• Packy McCormick — His Story: 80K Subscribers & Buzzy Angel in <2 Years (Behind the Newsletter)
• Not Boring: How Packy McCormick Built a $1M Newsletter Business From His Mother-in-Law's Basement
• Million Dollar Newsletter — Not Boring (The Flywheel)
• How Packy McCormick Turned Not Boring from Newsletter to Venture Fund
• Not Boring (with Packy McCormick) — Acquired Podcast
• 028: Packy McCormick – How Much Are 30,000 Subscribers Worth? (Nathan Barry)