I spent the day begging for money in Washington DC.
Yep, you read that correctly!
I’m currently on a business mastermind in the nation’s capital & we’re knee deep in sales training.
Yesterdat, they sent us out on the streets of DC with a mission to collect $50. We were not allowed to go to the bank, ask friends for money, or sell any of our current business services. And, we only had an hour and a half to do it in.
Sounds crazy. But how hard could it be?,” I thought. I was actually kinda excited about it.
Spoiler alert: It was an epic fail! Well, that is, if you are making judgement based on the pitiful $1 that my partner-in-crime, Laura Diaz, and I collected together.

However, if your judgement is based on the lessons learned and richness of the experience, then we took home the gold, baby!
Being smack dab in the middle of a city that neither of us were familiar with was a disadvantage from the start. But, we took off outside our hotel with blind optimism looking for some kind-hearted citizens willing to open their wallets for our cause.
Well, 1:30 in the afternoon on a Saturday is not a happening time in the middle of DC and we didn’t find much action. So, we decided to take a taxi to the National Mall, where we found the crowd we were looking for. But, plot twist: It’s actually kinda awkward to ask strangers for money! Who knew? People responded kindly, but some didn’t have cash, some didn’t speak English, and we ended up with 3 ‘no’s’ and 1 ‘yes.
Statistically speaking, that’s a 25% close rate, which is not terrible considering the circumstances. However, we felt super-awkward and started making excuses. And, then it started to rain. We convinced ourselves that a strategy change was in order. (While being nimble and willing to shift gears in your business is typically a strong-point, apparently not so much when you’re panhandling!). But, as suggested by a helpful local, we headed to Georgetown where there’s a high concentration of bars and restaurants. Surely drunk and happy people would be all in for our cause! And then … traffic.
As time was ticking away, we finally arrived and peeked into a few bars that were pretty dead. More excuses. We needed a lively crowd. Feeling defeated, but still determined, we settled on a slightly happening bar, deciding if we bought a beer first, it would not be so awkward to ask other patrons for money. We looked to our not-so-helpful bartender for support and he suggested that we “just cheat” and even offered to take a picture handing us money that he would pretend that he gave it to us. Umm, no. We were desperate, but we still, at least, had our integrity in tact.
At this point, we were out of time and had to get back to the hotel. We were also $35 into taxis and Uber rides, plus an $8 beer (that I never even got to drink. Damn!) to acheive our $1 reward for our, admittedly weak, sales efforts. (Which, I ended up passing along to a homeless guy, by the way).
This is no way to run your business, folks!! But, it does make for a good story and some valuable lessons learned.
We’re back for day 2 today (Sunday), folks. While we won’t be out begging for money, we will be touching base, making calls to our peeps! So, if you’ve ever wanted to have a strategy call with me, now’s your chance!! :) I’ll be calling as many people as time permits tomorrow. Send me your website and I will assess how well you are using storytelling to leverage your business and advise you on any opportunities I see to improve your copywriting.
Now, THIS is my comfort zone. I would MUCH rather talk with people about what I’m most passionate about in the name of service ANY given Sunday before begging for money again. ;-)
Sound good?Message me! And, we’ll try to make this happen.
xo,
Dawn Gluskin
(Dawn Gluskin helps soul-centered entrepreneurs own and share their stories that need to be heard in the world! She writes engaging and creative copy that connects & converts. When she is not cooking up some delicious word stew for her clients, she can be found on her yoga mat with her heart wide open, soaking up sunshine and salt air at the beach, devouring yet another luscious book, or throwing wild solo dance parties in her living room.)
#storytelling #copywriting #contentstrategy