Pomp's Newsletter Business Building Strategies

November 9, 2023

AI Summary

5 min read

The Newsletter Business Is Not One-Size-Fits-All

Anthony Pompliano (Pomp) has built a portfolio of media businesses around email newsletters, including the Bay Area Times, which grew from zero to 260,000 subscribers in about a year. But his operating philosophy resists simple formulas. The conversation covers newsletter strategy, the solopreneur myth, and how to think about building a media business that lasts.

The Newsletter Bubble Is Real — But Only for Commodity Content

Pomp agrees that there is a newsletter bubble, but he draws a sharp distinction. The glut is in "commodity content" — newsletters that regurgitate the same political or news coverage everyone else is doing. These compete aggressively on acquisition, driving up costs, and they will not survive.

The opportunity is in "unique content verticals." He gives the example of Marty Bent's newsletter Truth for the Commoner, which covers Bitcoin, financial markets, and politics through a single distinctive lens. "It will not be for everyone," Pomp says. "If it is going to repel some large portion of people, it will attract another large portion of people." That edge — an opinion, a perspective that cuts against the grain — is what makes a newsletter defensible.

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What you'll learn

1 (00:01) **Unpopular Opinions & Critical Thinking** - Pomp opens with a dinner-party icebreaker that reveals how many "unpopular" views are actually widely held, using climate change as an example.
2 (03:40) **The Newsletter Bubble Thesis** - Pomp argues we are in a bubble for commodity content newsletters, but there is scarcity in unique content verticals.
3 (05:52) **Bay Area Times Case Study** - A visual newsletter launched in Feb 2023 grew from 20K to 260K subscribers in 4-5 months.
4 (06:55) **Why Open Rate Doesn't Matter** - Pomp argues open rate is like revenue; the real metric is engagement (e.g., click-through rate).
5 (09:00) **The Evolution of Newsletter Business Models** - From 2018 to today, newsletters have diversified into advertising, subscriptions, events, and even hedge-fund-backed research.
6 (11:03) **How Bay Area Times Was Born** - Pomp discovered the visual newsletter concept through a cold outreach to his wife, then partnered with the founder.
7 (13:20) **Scaling Philosophy: Slow to Add Expenses** - The team optimized for long-term success by keeping headcount near zero until the model was proven.

+ Full timestamped outline available in the app

Show Notes

I'm joined by investor and entrepreneur Anthony "Pomp" Pompliano. Pomp hosts The Pomp Podcast, with over 50 million downloads, and writes a daily letter read by 250,000+ investors.

We talk about Pomp's approach to building resilient media properties, thinking long-term, and his best book recommendations for internet business success.

►►Subscribe to my weekly newsletter for insights on community, creators and commerce. You'll also find out when new and exclusive episodes come out from Where It Happens. And it's totally free.

https://latecheckout.substack.com

FIND ME ON SOCIAL
Twitter: https://twitter.com/gregisenberg
Instagram: https://instagram.com/gregisenberg/
TikTok: https://tiktok.com/@gregisenberga

BOOKS POMP MENTIONED

Unreasonable hospitality by John O'Leary

The Successor by Lachlan Murdoch

The 50th Law by Robert Greene and 50 Cent

Zero to One by Peter Thiel

Suleiman Ollian by Anonymous

How to Get Rich by Felix Dennis

Losing My Virginity by Richard Branson

The Rise and Fall of American Growth by Robert J. Gordon

Hidden Genius by Polina Marinova

The Outsiders by Will Thorndike

Elon Musk by Walter Isaacson

Urgency by John P. Kotter

The War of Art by Steven Pressfield

Good Profit by Charles Koch

LINKS FOR THIS EPISODE

Production Team: https://podflow.com
Pomp on Twitter: https://twitter.com/APompliano
Pomp on YouTube: https://www.youtube.com/c/anthonypompliano
Pomp's newsletter: https://pomp.substack.com

SHOW NOTES

0:15 - Anthony's provocative dinners for hidden beliefs
01:45 - Climate change evidence not as compelling
02:30 - Scarcity of unique perspectives in newsletters
03:00 - Click rates over open rates for engagement
03:45 - Media as repetitive software
04:15 - Bay Area Times' visual newsletters
05:15 - Unique Bitcoin perspective in Truth for the Commoner
06:00 - Bay Area Times' rapid growth
07:00 - Open rates for brand awareness, click rates for direct response
08:15 - Agora's focus on ecommerce conversions
10:15 - Monetization through hedge funds
11:15 - Joe Rogan's podcast profitability
14:00 - Bay Area Times' positive industry news
15:00 - Profitability before monetization for Bay Area Times
18:15 - Small teams and revenue for entrepreneurs
20:15 - Small teams for greater profitability
21:15 - Studying media greats like Rupert Murdoch
26:15 - Podcasts for expertise sharing
29:00 - Economic freedom and financial security
32:00 - Impactful employment business
33:00 - Small acts making the world better
34:45 - Pomp's book recommendation