Despite your many kind offers, I have no interest in having a posse.
From what I’ve gathered from watching HBO’s Entourage, it looks
expensive, claustrophobic and as if it would require pretending to care
about your posse members’ problems. Instead, I wanted to be in someone
else’s entourage. And not some overly serious movie star who keeps
talking about the environment, since that would mean doing things that
involve helping the environment. I wanted to do it right. I wanted to
join a rap posse.

So I got Flo Rida–a once struggling rapper who exploded late last
year with “Low,” which became a No. 1 song for 10 weeks–to let me join
his Poe Boy crew for his 29th birthday. As a gift, I brought him some
Grey Goose vodka and Patrón Silver tequila. All the products
name-checked in rap songs remove the stress from the gift-giving
process.

I stood outside Flo’s apartment building in Miami for
about 30 minutes while we gathered six members of the posse. Then we
waited an hour for them to make calls to inform even more members of
the posse about where to meet our part of the posse and to communicate
the details of all this to Flo. Logistics, I would discover over the
next 10 hours of endless greeting-and-leaving discussions, are the
worst part of entourage life: it’s like constantly trying to leave and
arrive at a Jewish wedding.

All the posse members besides me
grew up with Flo in the Miami projects and had been in other jobs
before their joint great success. Now Freezy manages Flo’s career, Four
Million is in charge of logistics, one guy videotapes everything, and
the gigantic Four Feet, who went to school for criminal justice and did
four years in the Army, serves as the right-hand man. I figured my
posse role was to be the one who looked really white in case we got
pulled over by the cops.

Riding shotgun as Flo drove to
Exclusive Motoring, where he was getting new rims put on his Bentley, I
learned the first rule of posseing: you don’t get to control the radio.
Flo blasted the new album he’s working on and sang along loudly. Though
I feared it was not within my bounds as posse member, I politely asked
if it was proper etiquette to sing along to our own music. “Oh yeah,”
he assured me. “If you don’t feel it, how can you expect anyone else
to?” I told him I loved the song with the sample of “Blinded by the
Light” and asked him to play it again. I was becoming a very good posse
member.

Picking out car accessories, it turns out, is exactly as
boring as shopping for women’s clothes. But I acted very interested in
rims, which I learned to call shoes and not hubcaps. I suggested that
his Bentley would look a lot friendlier if he lined the back window
with a row of small stuffed animals. It turns out it is above the pay
grade of a posse member to suggest such things. After the rims were put
on the Bentley, we spent about an hour outside, posse-gathering. Then
Flo decided to get someone to drive his Escalade over so it could get
new rims as well. I became very nervous when I found out Flo has 10
cars.

We then headed to the new, very expensive restaurant
Philippe Chow, where Flo was taking about 20 people out to dinner. On
the ride over, as he showed me his $40,000 diamond-encrusted watch, I
asked Flo, whose success is pretty recent and fragile, if spending all
this money was such a good idea. He told me that rapper Rick Ross told
him that you have to spend money with the confidence of someone who
knows he’s going to make a lot more. I informed him that Rick Ross is
not a certified financial adviser. “He’s certified. He makes a lot of
money,” he told me. I could not argue with that logic. Not if I wanted
to stay in the posse.

At dinner we drank a bottle of Dom
Pérignon, and Flo picked up the $6,000 tab. He called it “a Disney
World dinner,” since Flo seems to think going to Disney World costs
$6,000. Then we went outside and made lots of calls to one another
about which gas station we were going to stop at on the way to Diamonds
Cabaret, a gentlemen’s club, where we would tip the entertainers 5,000
$1 bills that we had brought in a leather satchel. I got in the Bentley
while Flo lay down in the backseat and began one of those phone
discussions I knew too well from my 20s; it started out about nothing
but escalated, with a lot about “your tone” and “Why you gotta be like
that?” and “Stop playing me,” followed by “I wrote you a poem.” When
the phone call ended, I said, “Flo, you’ve got 100 problems.” He said,
“Why’s that?” I said, “99 plus one.” It was the first rap joke I’d ever
made. Trust me, if you know Jay-Z, it’s a good one.

As we parted
ways at 2:30, having learned a lot about each other and how quickly
entertainers can sweep up 5,000 dollar bills with a broom and put them
into plastic bags, I was sad to give up my posse membership. Sure,
there was a lot of waiting around and being very sensitive to Flo’s
moods, but it was fun being in a really tight group. Especially because
I didn’t pay for anything.