As an investor, founder, CEO and business book author, I write about startups, design, how to build a good business, and I like to muse about culture in any form.

Sleeping with a stranger: via AirBnB

Meet Jon.  Meet his dog Pilot.  Jon’s a filmmaker. He grew up in Washington D.C.  He lives there today.  He knows all the best insider places in D.C.

Pilot’s a therapy animal.  He never barks and he likes to be petted.

Jon and Pilot live in this swish neighborhood of Washington D.C.  It is near all the coolest restaurants and tourist sites. If you were Jon’s friend you would want to stay with him because he would tell you all the best places to eat and visit.

He would tell you to go to “Paul”, a beloved Paris bakery and cafe that recently opened its first US location, just a short walk from Jon’s apartment.

The “Paul” cafe has delicious coffee.  You can sip it while sitting outside.  You can sit  in comfortable French-y chairs, next to these  fountains and be right across from the National Archives.  And if you didn’t eat it too fast to perhaps take a photo, you could savor your memory of a delicious French Apple Turnover.

See this couch.   It also belongs to Jon.  Pilot likes to sleep there sometimes.  If you were Jon’s friend you would be delighted to sleep there.  Jon’s a gracious low-key host.  You’d be so happy to have the chance to sleep in his studio.

Lots of people like to visit D.C.  They see the sights.  They go on school field trips.  They learn some history.  They see cherry blossoms.  They might even be there for business meetings.  People look forward to these trips.  They plan ahead.  They book nice hotels.

Or sometimes they do not plan ahead.  And they have nowhere to stay.  They find bad expensive hotel rooms on offer in terrible locations.   Sometimes they can afford to pay crazy prices to get the last room in town.  But sometimes they cannot do that.  And they just wish they had a friend like Jon who lives right next to the Metro stop, only two stops from the train station.

But they don’t know Jon.  They panic.  Then they remember to check that newfangled site AirBnB.  They find their new “friend” Jon.  They read happy reviews from strangers who stayed with Jon.  The strangers write that Jon’s couch is comfortable and Jon is nice.  The strangers say they happily paid $90 to stay in Jon’s studio apartment and sleep on his couch.

And that’s what I did. And I liked it.

I slept just fine.  The eye mask from Jon helped.  It created a semblance of privacy even as he and Pilot slept mere steps away. And the Sugar Daddy made me laugh.

Free bonus: I even got to take Pilot on a nighttime walk to keep me safe.

My son, calling on the phone, during my walk with Pilot:  “What?  You are in D.C?  You are walking some stranger’s dog?  You are sleeping in the same room as some guy you don’t know?”

Me:  “Yes dear.  And I would do it again.”

16 Responses to “Sleeping with a stranger: via AirBnB”

  1. Gene Cowan

    As one of Jon’s “old” friends, let me just say “yup.”

  2. Carl C

    When Laura and I were in Paris we went to Paul just about twice daily. $90 is a steal for such easy access!

    • julespieri

      Carl glad to know the real deal is real and not hype. I had never heard of Paul but I would travel to D.C. or Paris just to eat the delectable baked goods.

  3. Larry G

    His hospitality is no surprise to anyone who knows him. That’s Jon, one of the other treasures in the nation’s capital!

  4. Stephanie

    Another great post, Jules. I hope the folks at AirBnB pick up on it – what an amazing testimonial for them! I admit I’m a bit unnerved about the thought of staying at a stranger’s place (and I also wonder if the hosts are nervous about bringing strangers into their homes), so it’s nice to read about your excellent experience. And now I’m also dying to try Paul 🙂

    • julespieri

      I did just Tweet it to AirBnB…l. The hosts do have the chance to read reviews of the guests before they confirm. Since this was my first time Jon had to go on what he could research about me online. Given this blog, that was pretty easy! (He left a review so I am “in” the system now.) The main thing I worried about was if I would be too tired to interact at night. I tend to just work and crash in a hotel room. Jon respected that. He talked when I talked, and did his own thing otherwise. I would also worry about cleanliness. The reviews are really helpful there and his place was spotless. I couldn’t understand why a cleaning person was coming the day I left, in fact. Maybe he just always does that.

  5. Jane B

    Maybe if I were an idiot I would think that paying $90 for the privilege of sharing an open space with a stranger and sleeping on his dog bed/ couch was a great deal. Haven’t you heard of couchsurfing? A group of strangers that want to be your real friends, and truly extend hospitality, without a capitalist price tag. You are right in calling Jon a “friend” with quotation marks.

  6. High class CEO problems | Jules Pieri

    […] for the four years when I travelled for The Grommet on a punishing schedule of cheap travel, AirBnB couches, and general mooching off friends, I could not have scored a stay in a luxury resort to save my […]


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