No More Dinner and a Movie

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Taken from my guest blog on the awesome up and coming dating site HowAboutWe.com.

Dating is inherently awkward. It’s half-interview, half-recreation, and at the same time hopefully fun, but potentially excruciating. This invention of modern love has somehow mutated into the ubiquitous idea of dinner and a movie. “Let’s sit awkwardly across the table and watch each other shove food in our faces, then go sit in the dark in silence.” Whoever came up with that must’ve been a real Casanova.

That’s not to say eating out and watching films aren’t great activities, but are they really the best setting to get to know someone in a comfortable environment? “Check please!”

So isn’t there a better way?

What we do at Stray Boots is pretty simple; we provide fun and interactive, cell phone-guided “urban games” that are part scavenger hunt and part walking tour. You get challenges delivered to your phone and visit cool spots in the area to complete them. See a Stray Boots urban game in action here.

When I started the company three years ago, the idea was to provide people a more fun, interesting and interactive way to explore the city. (It was never to get anyone hitched or laid.)

But after we piloted our first “urban games” in 2009, we discovered a big segment of our customers were raving about something altogether different from interactive sightseeing. “We had lots of fun. Perfect idea for a couple on their 2nd date!” wrote Joe from NJ. “I highly recommend giving it a go for romantic roaming, that forthcoming date deserving a little more amusement and creativity than the last guy or girl brought to the table.” cheered Nell Alk from PaperMag. “An awesome date idea,” echoed hotdateideas.com.

Then I looked at customer photos (that they send in as part of the games’ “photo ops”) and realized what a huge subset of our customers are couples. And that got me thinking, why all the date-y-ness?

But then it made sense: Stray Boots games make an amazing date. You’re getting out and exploring the city, doing something active and interesting. You visit a bunch of places along the way, so you get to see what interests your date and what doesn’t. All of the challenges and spots you visit during the game give you stuff to talk about, so there’s never a dull moment, never an awkward silence.

On top of that, you play our games at your own pace, so you can stop along the way to grab a quick bite or a drink, and make the game fit nicely around your date, rather than fit your date nicely around a waiter’s impatience and a movie time. Best of all, it’s affordable and unique. It makes you look interesting for suggesting it, and doesn’t break the bank.

So after learning what a wonderful dating activity our games turned out to be, we decided to take it one step further. This year in anticipation of Valentine’s Day, we engineered a game made specifically for dating. It includes stops like petting puppies and practicing poetry, among loads of other playful challenges. So if you’re in the mood for a change of pace, check out one of our games. We can guarantee you won’t leave with something stuck in your teeth.

Happy New Year!

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We start the new year with high hopes for 2012. Of course, this time of year makes for good reflection as we see how far we’ve come in the last 12 months, and look ahead to all the exciting things we have on the horizon.

It’s amazing to see how different Stray Boots is this January than last. A year ago, we only offered games in New York. Now we have over 50 games in 13 US cities and the UK. 365 days ago, we were a team of only three people working out of a prison-cell-sized space where our elbows rubbed together. Now we’re five strong, and growing.

But for us, 2011 wasn’t just about growth. It was also about people finally noticing us. We ran a bunch of deals with Groupon and Living Social, and people took notice. Then we got little spots in Daily Candy and Thrillist, and that snowballed into a series of fun local TV spots and articles in the Washington Post, Fast Company, and most recently the NY Times. Meanwhile our private events business flourished, as we did events for Google, Johnson & Johnson, Accenture and dozens of other world-class companies. All in all, a great year.

So what does that leave for 2012 (aside from Mayan Armageddon)?

Well, first, we were accepted into the Entrepreneurs Roundtable Accelerator program here in NYC, along with nine other amazing companies (more on them next week). We’re super-excited about the opportunity as it promises to help us get from awesome-start-up to company-on-deck-to-take-over-the-world.

Second, we’ve come to realize we should be members of Expansion-Anonymous. That is, we’re completely addicted to growth. We love creating new games in new locations, and hate turning down customers who request Stray Boots where they live. So look out for us to come to a city near you, be it in the US, Canada, Europe, or elsewhere.

Thirdly, and most excitingly, we’ll be launching mobile apps this year. While our text messaging system is loads of fun, and creates a simple, easy-to-use interface that anyone with any phone can use, we think mobile apps are the future of our business. With the release of an iPhone app and then Android soon to follow, we know we’ll be delivering an even richer, more engaging experience than ever before. We’re giddy about all the possibilities and treats we have in store.

So enough of our rambling. If you haven’t already, sign up for our newsletter or follow us on Facebook to stay apprised of all of these developments. And let us know what you think we should do next, since we love to incorporate customer feedback into our plans.

Playfully yours,
The Stray Boots Squad

Pic the Smartest Alec – Where The Photos Go

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doing the heavy lifting in Nashville

For a long time, our games have included snapping wacky photos. Seeing them stream into our email address has been one of the most enjoyable parts of the business. In fact, we have hilarious customer photos all over the walls of our office, just to remind us of the smiling faces we try to create every day. But just this past week, we started to do a number of new things with all the awesome photos.

First off, we’ve just created a photo stream, where customers can retrieve and share the photos they send in. It’s also a great way to sneak a peak at some of the other fun games we offer and see what other Stray Boots customers are doing around the country. Secondly, for the folks who play by mobile web browser, we’ve added private photo repositories, where they can grab the photos they’ve uploaded. We’ll be adding cool ways to share with friends ASAP.

Thirdly, we’ve just begun a weekly Customer Photo Caption Contest! Each week, we pick a funny customer photo and allow the public to comment with funny captions. The caption with the most Facebook likes at the end of the week wins 4 tickets to the Stray Boots game of their choice. Anyone can comment, and if you win you can even give the tickets away as a gift if you prefer (but who would want to do that?). So definitely, check it out, post some captions, and let us know how we can make your photo experience (and entire experience) even better!

Happy Holidays!

Testing Out Some New Ideas – The Holiday Hunt

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Sound the Trumpets

We put a lot of work into every game we create: research, editing, and, most of all, time walking around the streets. What this generally means is great, high-quality games that are both entertaining and informative. What it generally doesn’t mean is that we can throw up a game in a matter of minutes.

Over the last couple years, we’ve received a number of suggestions from past customers to do event- and holiday-oriented games, around Valentine’s Day, St. Patrick’s Day, Halloween, July 4th, and just about every other holiday you can possibly imagine (boxing-themed Boxing Day game, anyone?). Though we completely agreed that all of these-or at least most of these-are great ideas and promise to be loads of fun, the concern has always been how much time it might take to create them.

Well, this year, we’ve said to heck with that line of thinking, we’re feeling merry and we want to do something festive for the holidays. We’ve decided to test out a Holiday Hunt to see whether there’s something to this idea of seasonal games, and how much it takes to pull off.

And what better place than New York City, where the store windows light up like Hanukkah candles and kids faces like Christmas trees (conveniently, the Big Joyful Apple where our office is as well.) So with great excitement, we’re hunkering down over Thanksgiving weekend with our leftover turkey and stuffing, to put together a Fifth Avenue Holiday Hunt to give you jolly jinglers some interactive merry-making.

We welcome you to try out our little test and to let us know what you think. And if you’ve played a Stray Boots game in the past, tell us how it compares. We cherish your feedback like the best present we’ve ever received, and hope you’ll continue to be as generous with it as you have in the past.

Happy Holidays!