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Today we see advertisements at sporting events, roadsides, menus, and pretty much everywhere else. What are some early (you define early, but I was specifically thinking of the hey-day of the Colosseum) examples of advertising for local businesses?

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Crassus was occasionally accused of setting buildings on fires as an advertisement for his fire department, wholly personally owned and Rome's only fire brigade at the time. Does that count? – Pieter Geerkens Apr 20 '14 at 22:57
Haha, everything counts! I was thinking more in terms of signs or promotional events - I suppose one could consider that a promotional event of sorts. Thanks very much! – Dylan Apr 21 '14 at 1:00
Yes, Crassus and his fire brigade would show up and offer 10 cents on the dollar for the burning building. If refused, the offer of 9 cents on the dollar would be made a few minutes later; then 8 cents; then 7 cents. Only after Crassus owned the building would the fire brigade commence work on the fire. – Pieter Geerkens Apr 21 '14 at 2:16
Wow, brutal. I suppose he became a very rich man. – Dylan Apr 21 '14 at 3:12
Yes he did. Crassus financed Julius Caesar, until his (Crassus's) death at the hands of the Parthians: en.wikipedia.org/wiki/… – Pieter Geerkens Apr 21 '14 at 3:14
up vote 5 down vote accepted

According to Mass Media in Ancient Rome:

Painted advertisements for games have survived under the ashes that buried Pompeii in 79 GC. These advertisements promoted the games’ sponsors as well as the games themselves:

Brought to you by Decimus Lucretius Satrius Valens, permanent priest of Nero Caeser, son of Augustus, twenty pairs of gladiators. And presented by Decimus Lucretius, son of Valens, ten pairs of gladiators. They’ll fight at Pompeii from the sixth day before the ides of April, through the day before. There will be a standard venatio [animal fights or men hunting animals] and awnings [to provide shade for spectators].

Around two millennia later the Houston Chronicle notes:

In Caesarian times, a Roman named Maius published in the Acta Publica one of the first known advertisements:

For rent in the Arrio Pollian Block belonging to Allieus Nigidus Maius, shops with rooms above, second-story apartments fit for King and House. Apply to Primas, slave of Maius.

About 19 centuries later, in the Chronicle's second-day edition, an ad ran that was similar in form, if not content:

$50.00 CASH and a small monthly payment at 5 per cent interest will secure a lot in the Empire addition, at the end of Fannin street car line. Better buy at once while you can have choice. Hooper, Fuller & McClintock, 218 Main.

Some additional sources:

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This is really interesting. I had guessed that sporting events would be advertised, but it's really fascinating to see the ad for the apartment. Now I wonder if the small shops themselves would advertise in any way... which also leads me down the path of whether or not shops might open multiple locations and become "franchises," so to speak. You've set me on the right course, thanks Pieter. – Dylan Apr 21 '14 at 3:50
With no real automation, and thus absent any ability to maintain mass-produced quality and standardization, and no concept of the corporation as business entity, franchises seems unlikely. (Collegia, fictional persons owning shared burial plots or places of worship, were not allowed to be general business operators in Rome.) – Pieter Geerkens Apr 21 '14 at 3:55
That's a good point. I suppose I'm also curious who started small businesses such as bars/restaurants and if they were successful, did they open additional establishments. – Dylan Apr 21 '14 at 4:15
Without double-entry bookkeeping, invented in the Renaissance Italy, hands-off ownership of an enterprise was very susceptible to embezzlement by the managers. – Pieter Geerkens Apr 21 '14 at 5:17
Makes sense. Thanks again Pieter, very enlightening. – Dylan Apr 21 '14 at 16:48

. . . the earliest surviving graffito is thought to be an ancient Greek brothel advert in Ephesus, now on Turkey’s west coast. Telegraph.co.uk

The same article contains other discussions of advertising in Pompeiian graffiti

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