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Jan 8, 2021 · 18m · top-founders

Packy McCormick Not Boring Substack Hits $50k Revenue, 25k Subs

Packy McCormick · 10m spoken Nathan Latka · 5m spoken Frank Bien · 4s spoken Eric Yuan · 4s spoken Vivek Bhaskaran · 2s spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Not Boring founder Packy McCormick joins Nathan Latka to break down how he scaled his free business strategy newsletter to over 25,000 subscribers and $50,000 in early monetization revenue. He discusses sponsorship economics, viral growth tactics, writing workflows, and leveraging editorial credibility into an active AngelList venture syndicate.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 35% of the talking time here. How this is scored →

Nathan as informed peer 3.7 Guest teaching 1.2 Guest disagreement 0.3 Nathan pushing back 1.2
05100:0010:000:23–2:58 · Nathan as informed peer 2/10 Latka Subscription Pitch and Promotional Interlude The segment begins with Latka's subscription promotional pitch before transitioning into a friendly conversation about Packy's background at Merrill Lynch and Breather. The tone is entirely welcoming and conversational.2:58–5:01 · Nathan as informed peer 3/10 Launching Not Boring and the Substack Model Nathan inquires about the mechanics of Substack and Packy's transition to full-time writing during the pandemic. Packy explains his free, ad-supported model while Nathan pulls up recent posts in real time.5:01–9:15 · Nathan as informed peer 4/10 Audience Growth Tactics and Viral Inflection Points Nathan digs into specific viral inflection points and verifies the exact subscriber math from Packy's Product Hunt launch. Nathan also probes whether Packy writes specifically to game social media distribution.9:15–13:25 · Nathan as informed peer 5/10 Newsletter Monetization and Sponsored Deep Dives Nathan presses Packy on newsletter economics, ad rates, and whether sponsored deep dives compromise editorial objectivity. Packy defends his natural optimism and transparent pricing model.13:25–16:18 · Nathan as informed peer 4/10 Packy's Weekly Research and Writing Workflow Nathan questions Packy's research and writing cadence, comparing it to his own book-writing experience. He frames audience growth as social capital precursor to financial upside, and Packy shares his revenue run rate.16:18–17:25 · Nathan as informed peer 4/10 Scaling an AngelList Investment Syndicate Nathan asks detailed questions about the syndicate structure, LP count, and per-deal capital allocations on AngelList. Packy explains how his newsletter content builds LP trust for deal flow.0:23–2:58 · Guest teaching 0/10 Latka Subscription Pitch and Promotional Interlude The segment begins with Latka's subscription promotional pitch before transitioning into a friendly conversation about Packy's background at Merrill Lynch and Breather. The tone is entirely welcoming and conversational.2:58–5:01 · Guest teaching 1/10 Launching Not Boring and the Substack Model Nathan inquires about the mechanics of Substack and Packy's transition to full-time writing during the pandemic. Packy explains his free, ad-supported model while Nathan pulls up recent posts in real time.5:01–9:15 · Guest teaching 2/10 Audience Growth Tactics and Viral Inflection Points Nathan digs into specific viral inflection points and verifies the exact subscriber math from Packy's Product Hunt launch. Nathan also probes whether Packy writes specifically to game social media distribution.9:15–13:25 · Guest teaching 2/10 Newsletter Monetization and Sponsored Deep Dives Nathan presses Packy on newsletter economics, ad rates, and whether sponsored deep dives compromise editorial objectivity. Packy defends his natural optimism and transparent pricing model.13:25–16:18 · Guest teaching 1/10 Packy's Weekly Research and Writing Workflow Nathan questions Packy's research and writing cadence, comparing it to his own book-writing experience. He frames audience growth as social capital precursor to financial upside, and Packy shares his revenue run rate.16:18–17:25 · Guest teaching 1/10 Scaling an AngelList Investment Syndicate Nathan asks detailed questions about the syndicate structure, LP count, and per-deal capital allocations on AngelList. Packy explains how his newsletter content builds LP trust for deal flow.0:23–2:58 · Guest disagreement 0/10 Latka Subscription Pitch and Promotional Interlude The segment begins with Latka's subscription promotional pitch before transitioning into a friendly conversation about Packy's background at Merrill Lynch and Breather. The tone is entirely welcoming and conversational.2:58–5:01 · Guest disagreement 0/10 Launching Not Boring and the Substack Model Nathan inquires about the mechanics of Substack and Packy's transition to full-time writing during the pandemic. Packy explains his free, ad-supported model while Nathan pulls up recent posts in real time.5:01–9:15 · Guest disagreement 1/10 Audience Growth Tactics and Viral Inflection Points Nathan digs into specific viral inflection points and verifies the exact subscriber math from Packy's Product Hunt launch. Nathan also probes whether Packy writes specifically to game social media distribution.9:15–13:25 · Guest disagreement 1/10 Newsletter Monetization and Sponsored Deep Dives Nathan presses Packy on newsletter economics, ad rates, and whether sponsored deep dives compromise editorial objectivity. Packy defends his natural optimism and transparent pricing model.13:25–16:18 · Guest disagreement 0/10 Packy's Weekly Research and Writing Workflow Nathan questions Packy's research and writing cadence, comparing it to his own book-writing experience. He frames audience growth as social capital precursor to financial upside, and Packy shares his revenue run rate.16:18–17:25 · Guest disagreement 0/10 Scaling an AngelList Investment Syndicate Nathan asks detailed questions about the syndicate structure, LP count, and per-deal capital allocations on AngelList. Packy explains how his newsletter content builds LP trust for deal flow.0:23–2:58 · Nathan pushing back 0/10 Latka Subscription Pitch and Promotional Interlude The segment begins with Latka's subscription promotional pitch before transitioning into a friendly conversation about Packy's background at Merrill Lynch and Breather. The tone is entirely welcoming and conversational.2:58–5:01 · Nathan pushing back 0/10 Launching Not Boring and the Substack Model Nathan inquires about the mechanics of Substack and Packy's transition to full-time writing during the pandemic. Packy explains his free, ad-supported model while Nathan pulls up recent posts in real time.5:01–9:15 · Nathan pushing back 2/10 Audience Growth Tactics and Viral Inflection Points Nathan digs into specific viral inflection points and verifies the exact subscriber math from Packy's Product Hunt launch. Nathan also probes whether Packy writes specifically to game social media distribution.9:15–13:25 · Nathan pushing back 3/10 Newsletter Monetization and Sponsored Deep Dives Nathan presses Packy on newsletter economics, ad rates, and whether sponsored deep dives compromise editorial objectivity. Packy defends his natural optimism and transparent pricing model.13:25–16:18 · Nathan pushing back 1/10 Packy's Weekly Research and Writing Workflow Nathan questions Packy's research and writing cadence, comparing it to his own book-writing experience. He frames audience growth as social capital precursor to financial upside, and Packy shares his revenue run rate.16:18–17:25 · Nathan pushing back 1/10 Scaling an AngelList Investment Syndicate Nathan asks detailed questions about the syndicate structure, LP count, and per-deal capital allocations on AngelList. Packy explains how his newsletter content builds LP trust for deal flow.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 61.1% · guest 38.9%0:00 · Nathan 61.1% · guest 38.9%3:00 · Nathan 34.4% · guest 65.6%3:00 · Nathan 34.4% · guest 65.6%6:00 · Nathan 21.7% · guest 78.3%6:00 · Nathan 21.7% · guest 78.3%9:00 · Nathan 28.8% · guest 71.2%9:00 · Nathan 28.8% · guest 71.2%12:00 · Nathan 30.3% · guest 69.7%12:00 · Nathan 30.3% · guest 69.7%15:00 · Nathan 26.2% · guest 73.8%15:00 · Nathan 26.2% · guest 73.8%18:00 · Nathan 68.3% · guest 31.7%18:00 · Nathan 68.3% · guest 31.7%
Sharpest disagreement ▶ 11:09 Packy defends optimistic sponsored coverage

Packy pushes back against the premise that paid analysis produces hollow praise, clarifying that his editorial filter only accepts companies he is genuinely bullish on.

 Hardest push from Nathan ▶ 11:01 Host presses on sponsored deep dive bias

Nathan directly challenges how much a company pays for an analysis and whether Packy can remain critical rather than writing a promotional piece.

 Biggest teaching moment ▶ 4:06 Explaining the open ad-supported newsletter model

Packy explains why keeping Substack free and monetizing via sponsorships drives faster growth and serendipity compared to paid subscription paywalls.

 Nathan holds their own ▶ 5:46 Host pulls live Product Hunt metrics

Nathan references exact live data from the Product Hunt post, citing specific upvote figures and dates to audit the viral growth claim.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Latka Subscription Pitch and Promotional Interlude 2000 The segment begins with Latka's subscription promotional pitch before transitioning into a friendly conversation about Packy's background at Merrill Lynch and Breather. The tone is entirely welcoming and conversational.
Launching Not Boring and the Substack Model 3100 Nathan inquires about the mechanics of Substack and Packy's transition to full-time writing during the pandemic. Packy explains his free, ad-supported model while Nathan pulls up recent posts in real time.
Audience Growth Tactics and Viral Inflection Points 4212 Nathan digs into specific viral inflection points and verifies the exact subscriber math from Packy's Product Hunt launch. Nathan also probes whether Packy writes specifically to game social media distribution.
Newsletter Monetization and Sponsored Deep Dives 5213 Nathan presses Packy on newsletter economics, ad rates, and whether sponsored deep dives compromise editorial objectivity. Packy defends his natural optimism and transparent pricing model.
Packy's Weekly Research and Writing Workflow 4101 Nathan questions Packy's research and writing cadence, comparing it to his own book-writing experience. He frames audience growth as social capital precursor to financial upside, and Packy shares his revenue run rate.
Scaling an AngelList Investment Syndicate 4101 Nathan asks detailed questions about the syndicate structure, LP count, and per-deal capital allocations on AngelList. Packy explains how his newsletter content builds LP trust for deal flow.

Statements from this episode (12)

Insight
McCormick: Free newsletters grow faster and drive more serendipity than paid models
“And I want to keep it kind of free and open. I think it grows better. More people can read it. It creates more serendipity. Like there's just a lot of good things that come if I'm, you know, kind of willing to trade off the security of a paid subscription.”
Packy McCormick Jan 8, 2021 ▶ 4:20
Assertion Not checkable as stated
McCormick: Not Boring grew from 500 to over 25,400 subscribers in eight months
“Yeah, it's wild. I had 500 in April and that many now.”
Packy McCormick Jan 8, 2021 ▶ 4:58
Assertion Not checkable as stated
McCormick: Product Hunt launch added 2,000 Not Boring subscribers in days
“Got to number two, and I think in a couple of days that drove 2000 new subscribers.”
Packy McCormick Jan 8, 2021 ▶ 5:33
Insight
McCormick: Writing about Stripe drives more employee shares than Facebook
“Like I wrote about Stripe and then everybody at Stripe reads the piece where you write about, you know, X, Y, Z company that's big enough that it can have an impact. But small enough that they're not being written about every day. Like, you know, people within…”
Packy McCormick Jan 8, 2021 ▶ 8:10
Prediction Held up
McCormick: Substack will not build an ad network anytime soon
“I don't think they're going to be building an ad network anytime soon, which is fine by me”
Packy McCormick Jan 8, 2021 ▶ 10:13
Disclosure
McCormick: Not Boring charges $10,000 for sponsored deep-dive essays
“Yeah, 10 grand in January and kind of it scales, scales linearly with the audience is how I'm thinking about it now.”
Packy McCormick Jan 8, 2021 ▶ 12:09
Disclosure
McCormick: Not Boring charges $4,000 for Monday ad placements
“I think in January the rates are going to be about 4000 for a Monday and 2500 for a Thursday.”
Packy McCormick Jan 8, 2021 ▶ 12:24
Assertion Not checkable as stated
McCormick: Not Boring Monday posts surpass 50,000 views on 26k subscribers
“Like, you know, the 26,000 person list, the past few posts have gotten 50,000 plus views just the past few Mondays, because they just kind of take off a little bit at this point, which is great.”
Packy McCormick Jan 8, 2021 ▶ 12:37
Disclosure
McCormick: Not Boring generated $50,000 in first three months of monetization
“I've been monetizing since Call it late August, early September. So we kind of, it'll be three months of monetization, and I would imagine it somewhere around 50,000 or so, so it's a good run rate.”
Packy McCormick Jan 8, 2021 ▶ 15:57
Disclosure
McCormick: Not Boring investment syndicate has about 500 limited partners
“There's about 500 LPs in the syndicate.”
Packy McCormick Jan 8, 2021 ▶ 16:23
Disclosure
McCormick: Syndicate deal sizes grew from $100,000 to over $200,000
“About a 100,000 each, a little bit more. Now it's 200 and that's two up to 50.”
Packy McCormick Jan 8, 2021 ▶ 17:15
Disclosure
McCormick: Works 60 to 70 hours weekly and avoids hiring for freedom
“Freedom, and, you know, maybe at some point it stagnates, and I, the revenue doesn't keep going up, and the audience size doesn't keep going up, but the fact that I get to do, like, do this on my own schedule, and it's 60, 70 hours a week, it's a ton of work, …”
Packy McCormick Jan 8, 2021 ▶ 17:48
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