Hi everyone! Welcome to this week’s installment of Tom’s Top 3 Tuesdays, where I highlight three pieces of content (Podcasts/Shows/Songs/Articles/etc.) that I found interesting or noteworthy from the prior week.
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Francis Ford Coppola is one of the best to ever do it. Unfortunately, critics have not been impressed by his latest film, Megalopolis, which released last Friday. Coppola’s passion project bombed to the tune of a $4M gross over its opening weekend, garnering the dysphemism “Mega Flop(olis).”

I haven’t seen the movie yet, but I am still very excited. A surreal, bizarre brainchild of a legendary filmmaker? I’m in.
Flop or not, this edition of the newsletter is devoted to the man behind the madness.
Let’s get into it.
Trung is an entrepreneur and co-host of the Not Investment Advice podcast. Before his career in tech, Trung was a screenwriter, and he remains a cinephile today. In his Substack, he gives Coppola his flowers, albeit with a entrepreneurship slant.
Trung points out that there are many similarities between filmmaking and startups, such as fundraising, recruiting talent, and delivering a finished product. Using 8 films and 2 business ventures as benchmarks, Trung details the up-and-down career of Coppola.
The defining theme across Coppola’s life is that he was always willing to bet it all to retain creative control. And when I say bet it all, I mean it literally. He declared bankruptcy three times in nine years during the 1980s and 1990s. When the budget for Apocalypse Now swelled to over $30 million, Coppola mortgaged his house and took out 7 figure loans with interest rates over 25%.

This self-conviction-bordering-on-blasé-blindness continues to this day. Coppola has parlayed his wine fortune into his swan song, Megalopolis. After selling his winery in 2021 for over $500M, Coppola self-financed the $120M film, which he first conceived of in 1977 while working on Apocalypse Now.
I don’t care if Megalopolis sucks. Coppola is a baller.
[Podcast] The Daily Stoic - Francis Ford Coppola Opens Up About How Philosophy Has Inspired His Life and Career
This was a fascinating and somewhat surprising pairing. Ryan Holiday is a prolific author and the primary espouser of Stoicism. On the surface, it didn’t seem like they would have a lot to talk about.
Turns out, Coppola is also an extremely well-read individual, and his interests extend to the classics and philosophy. Coppola explains that he himself is an Epicurean.
The premise of Megalopolis is “what if the fall of Rome occurred in modern day New York?” Accordingly, the two discuss ancient Rome and their favorite philosophers. Both Holiday and Coppola share an absolute love for Marcus Aurelius. Coppola even quotes Aurelius multiple times in Megalopolis.
The highlight for me from this interview is how Coppola stresses the importance and necessity of artists to steal from the past. He provides multiple examples about how his reading has influenced his film projects and how he has drawn inspiration from other filmmakers.
Coppola refers to an obscure book by Honoré de Balzac, where Balzac explained how he writes so that others may be influenced by his words and he can therefore become immortal in their works. I think it is safe to say that Coppola has been immortalized by his impact on current filmmakers and those to come.
[YouTube] Thomas Brown - Francis Ford Coppola Wines - 1997
This video is peak 1990’s-core. It provides a brief overview of the Coppola Winery timeline and also paints a portrait of Francis the man. Even in 1997, it is clear that Coppola always viewed the wine business as a means to buy his creative freedom.

That wraps up this edition of Tom’s Top 3 Tuesdays. If you know anyone who would like this newsletter, please consider sharing. I’ll be back next week. ✌️