The Homeless Heads to the Hamptons.

by beckystraw on June 5, 2012

Most people have no idea I was homeless. I tried not to tell them. I don’t want them to think that our vision is wild and unsustainable. My co-founder and I didn’t take salaries for our first year, in order to pour more of our donations into the field. But nine months into bootstrapping our nonprofit, my credit card maxed out.

My friend Stacy came to my rescue and invited me on to her couch. I threw my stuff into storage and headed to her apartment with one suitcase, a printer/scanner combo and coffeemaker.  My “few months” on the couch quickly turned into ten. I thought it would be grueling. It turned into the best decision I’ve ever made.

In forcing me to ask others for help, I was overwhelmed by hospitality and friendship. And showered with a kindness that I can never quite repay.

Here’s 14 of the fun places I’ve stayed:

1. STACY POMMER’S – West 72nd Street -Stacy lives in a posh upper west side apartment, across from The Dakota on 72nd. She also happens to have a visual impairment, so we are ready with excuses if her condo board ever complains about her squatter on the 15th floor. As it turns out, my role as her “visual aid” has only come in handy for reading the score of the football games, who is voted off on The Bachelor, and pasting a fake snake tattoo on her back so she can prank her friends on her birthday. If you ever want to see your friends squirm, have a visually impaired girl ask them if her new tattoo of a hideous cobra looks fantastic.

2. PEACE CORP’S 50th ANNIVERSARY CELEBRATION, Washington DC. Two weeks after my credit card maxed out, the Peace Corp Association called and announced that I had won a writing contest, worth $5,000. I just had to pick up the check at their gala. My younger cousin happened to be in DC that weekend for work, and was able to sneak me into her room at the Mandarin Oriental Hotel. The $5,000 became my lifeline until February.

3. THE SANDERS. 100th Street and Riverside Drive, NYC. Carrie and I used to work together at charity: water. Now, she is on our board and the proud mom of two little boys.

4. THE STRAWS. Lafayette, California. Home at my parents’ house for a wedding. Laid in bed wishing my 31-year-old self could tell my 13-year-old self, “One day, you’ll regret begging dad to buy this freaking futon bunk bed!”

5. NANA STRAW. Agoura Hills, California. Borrowed my moms car and drove to LA for meetings. Twice my Nana called my dad to ask if it was ok that I was late for curfew.

6. THE LANDERS. Olympia, Washington. Flew to Washington to attend a fundraiser with my co-founder, Jody Landers. Jody is a popular mommy blogger and mom to six kids. Discovered that she’s a great soccer mom too, and that kids really do wake up at 6 AM - even with a stranger asleep on their couch.

7. STEPHEN JONES. Seattle, Washington. Stayed at Stephen’s while he was in India installing water systems for A Child’s Right. I think we’ve only met twice, but we chat sometimes on twitter - which makes him perfectly trustworthy of leaving me to press all the wrong buttons on his three remote controls, despite two pages of instructions. Coolest. Apartment. Ever.

8. FORT LAUDERDALE AIRPORT. While on the west coast, a primetime TV news network asked if I could meet them in Haiti to shoot our stove campaign. I took a red eye to NYC to get my passport, and another to get to Haiti. To save money I slept under a row of airport seats. Not gonna lie, this wasn’t the best idea I've ever had.

9. SUMMIT SERIES, Basecamp. Tahoe, California. Met a bus in San Francisco and drove to Tahoe with 30 other young entrepreneurs. Summit has been coined the “Davos for Generation Y” And the three-day conference is a sensory overload of ideas, dreamers and doers. A few travelers included the founders of Shopify,, Prezi, a few start-ups like, Circa, and the comedian Baratunde Thurston, who was 48 hours away from his first book launch.

10. THE EX’s BACHELOR PAD, Upper West Side, NYC. An ex found out I was homeless and offered his apartment while he was at Davos. Apparently, last year he was “too busy” with his new job to continue dating, but not too busy to purchase some new “art.”

11. SOCIAL MEDIA WEEK WITH NOKIA, London, United Kingdom. Nokia flew me to London to speak, and over a fancy dinner asked if I would be interested in a potential partnership. I didn’t mention that my suitcase was full of Snickers bars, so that I wouldn’t have to spend any money eating while I was there.

12. ALEX ABELIN, East 13th Street, NYC. Alex is a Community Relations Manager for Google. Little did Alex know that being a “Community Manager” also meant housing all of the broke social entrepreneurs in his community.

13. CECI THOMAS, 95thstreet and Riverside Drive, NYC. Burned out from spending the last three years launching a financial start-up, Ceci took a break and went to Florida. She got a great tan; I got her studio for two weeks. Realized I’ve been homeless for nine months, and I'm starting to look like a bag lady.

14. KIM MASSEY, 87th and West End, NYC. Kim is a recent transplant from Nashville, and Carrie Sander’s older sister. We didn’t know each other well before I spent two months on Kim’s couch. Now, I am forever grateful to have a new friend.

I’m taking a small salary now, and on Friday I moved off Stacy’s couch. In a windfall of irony, ten friends and I rented a place in the Hamptons for June, just as a friend had her place open up in the east village. So now I have two places to live this month. I went from wheeling all my stuff up and down subway stairs like a sweaty hermit crab, to now taking conference calls on the beach.

Last Friday night a guy I met said, “I think our generation is more interested in experiences and friendships. We’re not striving to get rich and attain more than ‘the Jones’. Our focus is on living and working for causes we care about.”  He added, ” I’m totally broke. But I love my life.”

Ironically, he happened to be telling me that as we stood in Adrian Greenier’s kitchen, as Adrian grilled up steak for 50 “fearless” NYCers, as the invitation stated.

I looked around the room, filled with some of the most interesting and well, “fearless” people I am lucky enough to know and I said, “Ha. Me too.”

Fortunately broke.


  • Pingback: B.O.L.D. Thought | * B.O.L.D. - Build. Obtain. Lead. Develop. *

  • hosting

    I intended to create you the tiny observation to finally say thank you over once more for these spectacular thoughts you have shown on this site. This is so tremendously open-handed of people like you to grant publicly just what most people might have made available for an electronic book to obtain some bucks on their own, notably considering that you might have done it if you considered necessary. These pointers additionally worked to become a good way to be certain that some people have the identical zeal just like mine to understand much more and more on the subject of this issue. I know there are many more pleasurable moments in the future for individuals who examine your weblog publish.

  • Lauren Friedman

    If you ever make your way to Boston, I have a couch (with a pull out bed) and it has your name written all over it. You’re amazing.

    • beckystraw

      Lauren!! I miss you. Come visit NYC. I have some desks for you to clean. ;)

  • Eileen

    I stumbled across this blog post randomly, and as a currently homeless entrepreneur myself, SO appreciated it. Luckily, I’m heading out of the country in two weeks which cuts short my homeless time. Unluckily, I had two cats that were homeless with me (they are “couchsurfing”, i.e. fostered) for the next year.

    Anyways, in awe of how long you managed to do this. Thanks for sharing :)

    • beckystraw

      Awesome Eileen! I hope your travels and homelessness are treating you well. Good luck with the start-up and thanks so much for saying hi!!

  • rahul urs

    I just bought 5 snicker bars after reading this blog. scarily inspiring…keep it going !

  • Tiffany

    Greatest quote- that man has some great insight into our generation.

    Love you friend. This is wonderful.

    Also, give Adrian my number… I have a crush on him and I’m positive we’d make the cutest couple.

    • beckystraw

      Done and done, Tiff. :) Thanks again for being you.

  • Jessica Thompson

    I was linked to your blog by Ceci Thomas (a good friend of mine) and I just wanted to tell you I found it to be so inspiring. Last year I, too, was “homeless” and had to rely on the kindness of friends to help me through a very difficult financial time (including being housed by several friends) and it was such a humbling, enlightening and incredible experience. To have been in the worst dire straits financially, but to feel nothing but love & support and to know I wasn’t alone…I learned through my year from hell last year that what truly matters most isn’t what we have in our lives, but who. Fortunately broke, indeed.

    P.S. Kudos to you for your work! I had an incredible time at your guys’ gala and felt honored to be supporting such an inspirational non-profit.

    • beckystraw

      Jessica! How amazing, right? This experience was truly the first time I had needed help, and the outpouring was phenomenal. In fact, moving into my apartment was a little sad…I loved my experience of being around friends and feeling their support! So glad things seem better for you. So honored you attended our gala! Thank you. PS: Ceci is my favorite.

  • cassie

    i absolutely love this post.
    and as a wife/mother of 3/teacher/pet owner/homeowner, your past year almost sounds a little dreamy. :)
    the grass always seems greener, doesn’t it!
    cheers! here’s to a HUGE upcoming year for the adventure project.
    so proud of you guys!!

    • beckystraw

      Love you too, Cassie! I look at your cute kids and think, you are the absolute coolest mom ever.

Previous post:

Next post: