Next year in Miami?¹

Ruminations on an unlikely startup hub

Juan Ponce de León, finding himself without office, and seeing himself rich, determined to do something by which to gain honor and increase his estate. As he had news that there were lands to be found at the northern border, he resolved to go explore toward that part. And thinking this land was an island, they called it Florida because it had a very beautiful view of many cool groves; moreover, they discovered it in the time of the Feast of Flowers (Pascua Florida)².

—Antonio de Herrera y Tordesillas, Historia General de los Hechos de los Castellanos en las Islas i Tierra Firme del Mar Oceano (1601)

In addition to this piece, I interviewed Mayor Francis Suarez, the mayor who tweeted his city on to the map.
I also interviewed Keith Rabois, the first big VC to (publicly) move to Miami, about why he thinks Miami can compete with Silicon Valley.

Fighting the BoBo FOMO

One of the anchors keeping elites in the few coastal urban enclaves considered humanly habitable is what David Brooks so memorably called BoBo culture (short for ‘bourgeois bohemian’). This is a life aesthetic characterized by artificially distressed wood (and people), and what Whole Foods so successfully mass-produced for a wider market. If you’re not knowledgeably sampling sumac-dusted man’oushe or carne asada totopos while sipping a Russian River pinot or a double dry-hopped hazy IPA, preferably somewhere where rents start at $3000/month, are you really even alive?

I was raised in the Miami of the wild 80s and 90s, and more or less abandoned the city for 20 years before going back due to a family illness circa 2014. Much to my everlasting shock, all the twee fineries of overpaid SF tech life were there: pretentious craft beer poured by bearded lumbersexuals inside stylized industrial loft spaces; whimsically-named, garishly-painted food-trucks clustered in parking lots-turned-parks serving Korean/Mexican fusion tacos; pompous ‘Third Wave’ coffee places (in a city where espresso was already ubiquitous) featuring pierced baristas conjuring a pourover with all the seriousness of a priest performing the eucharistic miracle; glass-clad, high-rise condo buildings, indistinguishable from the same douche-cubes in SF’s SoMa (“GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES”) growing like mushrooms in a dewy field throughout the formerly sleepy downtown.

¿Qué coño, Miami?

Where were the Cuban guidos with the exposed chest hair, St. Lazarus medallions, and roaring Camaros? Where were the loudmouthed radio personalities launching splenetic anti-Castro diatribes on every Spanish-language radio station, basically 24/7? Where were the rundown timbiriches serving black-as-death/sweet-as-love coffee for $0.35 out of tiny paper cups amidst a scrum of guayabera-wearing old farts angrily deconstructing (once again) the latest from Cuba or a recent election.

Jorge Conde, a general partner at Andreessen Horowitz and another of that rare breed of born-and-bred Miamians currently in Silicon Valley, shared similar astonishment with me in a WhatsApp message:

We go back every Thanksgiving (not this year unfortunately). It’s definitely a real city now. I remember grabbing drinks on a rooftop patio in Brickell [the ‘Broadway’, so to speak, of Miami] and being amazed at the canyon lined by glistening white and glass towers.

This isn’t the city Jorge and I (or Francis Suarez, the mayor) were raised in. Whither the Miami of yesteryear?

Moved mostly, to the western suburbs of Kendall or South Miami where the well-assimilated Cuban middle-class mostly lives. Hate to break it to you, but Little Havana is like SF’s Chinatown: a residually-authentic living museum kept alive mostly for tourists. You can still get an unpretentious Cuban bistec de palomilla (or an Argentinian parrillada) in a family-style restaurant as good or better than anything back ‘home’, but it’s no longer the unique source of the previous vibrant but definitely non-BoBo cosmopolitanism.

Nowadays, walking around Wynwood, the formerly rough and industrial and now cool and artsy neighborhood, the vibe is more Soho and SoMa than anything I ever experienced as a youngster. The Bobos are not only at the gates, they’ve moved in and brought their sous-vide cookers with them. You can live an absolutely Brooks-approved BoBo life in Miami (or Austin or Nashville or Park City), and do your part for capitalism while doing so. In Miami, that’s mostly thanks to a combination of plucky exiles, fortunate geography, and accommodating tax laws dating from when Florida was more sleepy retirement community than glitzy tourist destination. That glitzy brand, which is how many Americans tend to see the city, is in many ways a misconception though.

The concept of the entrepôt

Miami is among that set of curious characters: the urban entrepôt (from the French word for ‘warehouse’). Whether Havana or Beirut in their day, Hong Kong before the Chinese decided to squash it under their bootheels, or Singapore or Dubai now, the world has always featured gateways that intermediate two worlds. Usually this city-state middle-man straddles some large hegemonic power and some (culturally foreign) ‘near abroad’. And that’s what Miami is: it’s the intersection in the Venn diagram between American business culture and rule of law, and Latin American culture and vitality (not to mention a market of 650 million consumers and a combined GDP of over $5 trillion). To most Americans Miami might mean beaches and bling and palm trees, but in Latin America it’s something else altogether: a combined bolthole, bank and bazaar. Miami’s airport is a hub city (unlike SFO) with a whopping amount of international cargo and passengers passing through. The city hosts a slew of multinationals and their regional offices, from Proctor & Gamble to Facebook. Brickell Avenue is a sort of Latin American Wall Street, lined with the logos of every major commercial bank. If you do business in LatAm, you’ve got a Miami office.

Culturally, Miami is like that cantina in Star Wars’ Tatooine, but at city scale: You're going to hear Spanish inflected with every accent from Madrid to Buenos Aires (and you'll learn to distinguish between them), as well as Hebrew, Russian, French and God knows what else. It’s Bartertown meets tropical wild west, with high-rises.

Share The Pull Request

The city’s politics also reflects that (real) diversity. In San Francisco you have the Potemkin-village diversity of Anglo elites legislating labels for minorities while changing school names in some culture-war shell game, with a breadth of political opinion that could safely fit on the head of pin. In Miami you have a city run by the polyglot exiles who establish their own schools and don’t necessarily speak your language, either politically or literally (Miami is the only city in the US where most users of Duolingo are learning English as a foreign language).

Post-COVID, I’m less convinced geographic proximity actually means anything when it comes recruiting startup talent. Difficult to imagine it’ll be very hard to convince college grads to move to Miami to take jobs at tech companies. Just imagine their winter Instagram feeds and the FOMO from their former Boston or New York circles. Also won’t be very hard to attract more senior talent as an engineering manager realizes that in Miami, unlike San Francisco, a rank-and-file employee can actually afford a family-sized home.

That Miami can be an international business hub is beyond doubt for anyone who knows it well. But even as a former Miamian bullish on the city in general, I’m somewhat skeptical a city more known for silicone than silicon could actually nerd out enough for tech. While Miami has a vibrant trader/arbitrageur culture, I’m really not sure about creating a hacker/builder one.

And then, I saw this tweet:

Obviously a Photoshopped meme with a superimposed Y Combinator logo, it shows perhaps Miami’s most emblematic building, the Empire State Building and Ellis Island of Miami rolled into one, Freedom Tower. Now somewhat lost among the glass-and-steel canopy of Miami’s skyline, there’s no more symbolic building than this one, done in the Spanish Revival of 1920s Miami.

As a 17-year-old boy in 1962, my father walked out of its doors alone (as he constantly reminded me) with three things in his pocket: a Spanish-English dictionary, a plastic safety razor and a bus ticket to Chicago where a relative lived. That's what the Feds gave you.

His parents, my grandparents, would take months to get out, getting stuck with visa issues while fleeing through Mexico. Thousands of other Cuban children, some barely beyond their toddler years, came alone and were raised as essentially orphans by the Catholic Church in what came to be known as ‘Operation Pedro Pan’. It was a panicked rush for the doors before the Iron Curtain made its final and decades-long tropical detour around Cuba.

Freedom Tower was later bought by Jorge Mas Canosa, a construction tycoon and founder of the Cuban American National Foundation, the leading Cuban-American lobby group. The tower’s first floor was turned into an expansive museum of the Cuban exile, one of the few such institutions memorializing an exodus that’s mostly ignored in the American mainstream. In one generation, Freedom Tower went from a Cuban refugee center where Cubans like my father walked out desperate and penniless, to a Cuban museum bankrolled by one of its most successful arrivals: that’s what Miami made possible for a generation of exiles.

And the Miami story continues. One of the city’s newer neighborhoods Weston is jocularly referred to as Weston-zuela as half of Caracas seemed to move there when the ‘Bolivarian’ revolution in Venezuela reached its more lunatic and tragic stages. When the Argentinian economy suffered a(nother) currency crisis, Miami was suddenly dotted by businesses flying the Argentine Celeste y Blanca whose owners assaulted your ears with their colorful Rioplatense accent.

To someone who left Miami for the ‘big leagues’ of Silicon Valley and is now seeing some of his peers return to his hometown, this potential flight of mainstream American tech to the oddball Latin American quasi-city-state is surprising and ironic. But seeing the YC logo on Freedom Tower, as glaring a meme as it might be, lessens the contrast. Miami has always been a place of refuge for people fleeing some past or another, whether the Cuban exiles of my parents’ generation, Venezuela now, or perhaps hungry entrepreneurs ready to build something new. In many ways, this is all less unlikely than it might seem. Twenty years from now, Miamians may look back to today, as I do now to my childhood, and marvel at the enormous and utterly unexpected changes to a city forever in a tizzy of shameless re-invention.


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  1. This is an ironic clin d’oeil at the curious Cuban-American practice (at least among my parents’ generation) of regularly toasting to ‘next year in Havana!’ (much as the Jews say ‘next year in Jerusalem!’ at Passover). Observing the Silicon Valley class consider moving to the city of escape I escaped is the unexpected kick to the brain that spurred this piece.

  2. Ponce de León Boulevard is now one of the main roads through posh Coral Gables (a product of the 1920s Florida land boom, done in a Spanish Revival style).