Live Off Groupon is Over
Long story short, our Groupawn lived off Groupons for an entire year! Check out Groupon's amazing local deals and see if you can do the same! ... Or just browse and buy at your leisure.
See Deals at Groupon.comMay 11th
Day 2
Getting Around the Windy City
So day 1 was a breeze and not entirely the result of the holes in my paper suit and the fact that I was in the Windy City (much to the dismay of Groupon, I’m sure). I obtained clothes, was well fed, and barely even had to walk anywhere thanks to my Groupon for Antique Coach & Carriage who took me all around the city to buy clothes. Cathy, the carriage operator and part time tax consultant, was great and even gave me some free tax advice regarding my $100,000. NBC news joined me on the first leg of my journey to City Blue Apparel & Denim. This was the closest clothing store to Groupon Headquarters that I had a Groupon for. I was very pleased that I was able to replace my paper pants by squeezing into some “skinny jeans” (that’s a first) and I got a skin tight (that was the closest thing they had to my size) t-shirt that I chose to wear under the Groupon suit jacket since it was a bit cold when the horse picked up the pace.
Cathy and I then trotted from Old Town to Lincoln Park (about an hour) to Star Struck Apparel. My thinking was that they’d have a sweatshirt or hoodie so I could finally be done with this paper nightmare. The owner was really excited I was there and told me to have a look around. After checking out the merchandise, a fantastic selection of sports apparel for fans of Chicago teams and careful deliberation, I went with a Cubs zip-up. I needed something that would be versatile, fairly lightweight and it was on sale, not to mention extremely comfy. I also got a Black Hawks “One Goal” tee (in my actual size!).
Now that this clothing situation was under control, I asked Cathy to take me to Bike and Roll Chicago in
Millennium Park. They rent bikes, roller blades, and most importantly, give Segway tours! Since I had been on one of their tours in the past and well, I’m the Groupawn, they donated a Segway to my cause for the afternoon. Let me say…way more fun than walking! This is when the reality of this year set in. I can pretty much do whatever I want. As I rode down Michigan Avenue, free as a bird, contemplating where to go next, I remembered seeing a Groupon for Base Bar in the Hard Rock Hotel, just down the street. I was parched and hungry from my busy morning…perfect I thought.
I parked my Segway on the sidewalk next to the Bellman and set the alarm. He gave me a funny look, so I explained why I was there and he agreed to keep an eye on my sweet ride. When I got to the bar, I was the only one there. I asked the bartender if they served food as well and he said they did, but the Groupon I had only covered drinks. I explained to him about my new life and he gave me some water while I tried to figure out how to get something to eat. Moments later, a young man named Jose took a seat at the bar. When he asked for a menu, I introduced myself. He had just arrived in town from San Jose, CA for a bachelor party and had a couple hours to kill. I showed him my Groupon and asked if he’d be willing to buy the food if I took care of up to $40 in drinks (as my Groupon said). At first he thought I was trying to hustle him, but the bartender chimed in that I was legit so Jose threw caution to the wind. We drank a couple rounds of Midwest craft brews and each ordered the mini-burgers. We chatted for awhile and had a few more drinks and hit our max that the Groupon would cover. Meanwhile, a friend called to find out where I was and as he was fairly close, he decided to stop by. Jose bought us all another round of drinks and we moved over to some couches in lounge area so that I could plug in my laptop and phone for the first time. I played around with my new equipment, set up my email on my brand new iPhone and Jose’s friends arrived shortly after. The afternoon was melting away and I had to return the Segway.
On my way back to Bike and Roll, I ran into a friend leaving Argosy University (across the street from the bar). This person’s identity will remain protected since this student offered to get me a visitor’s pass and access to the school’s computer lab, so that I could print off some more Groupons. In exchange, I offered to get us dinner at Phil Stefani’s 437 Rush.
I made a reservation, returned the Segway and met said friend at the restaurant. It was quite convenient that all of these places were located so close together. Upon arriving, the hostess, who was familiar with my challenge, greeted us with quite a bit of excitement. Everyone looked so fancy, and there I was in jeans and a Cubs hoodie. What can you do? Our waiter didn’t seem too pleased when he saw the Groupon and I informed him that we were on a bit of a budget. Understandable, I’ve spent two years waiting tables at a fancy steakhouse, but he should have hid it better. I tried to reassure him that we’d take care of him and told him I’d be happy to let him pick out a Groupon as his tip but he didn’t seem to like that idea either. Oh well…we moved on to more important things…the food. My guest wanted steak and suggested the 30oz “Prime Rib Eye Chop” and a “Double Baked Potato” and I had my heart set on the “Tortelloni DiVitello Burro E Salvia” (veal tortelloni with brown butter, aged parmigiano, and crispy sage). We decided it was in our best interest to just share everything. My concern was that after tip, my friend would owe about $30 over the $60 Groupon I had, which can be a lot for a student. I decided to try to find someone else who would help me out other than our waiter. The Maître d’, Alessandro Magno, stopped at our table and mentioned the Groupon I had brought so I asked if he was aware of the contest that I’d won. After a bit of explanation and seeing the stack of Groupons in my hand, his eyes lit up. He 
thumbed through a few and picked up one for $110 at Blo Salon and Day Spa (“for my wife” he claimed). He took a look at our check, agreed to cover it and take care of the server for us. Then brought us 2 glasses of Averna and the best cannolis I’ve ever had in my life. He explained that their secret was to bake them (rather than fry) and their use of Chantilly mousse (inside), imported vanilla gelato and Belgium chocolate (on the plate). What he didn’t mention, but I must, was the sprig of mint they used as a garnish. It was by far the most fragrant and flavorful mint I’ve ever encountered. We thanked him for his generosity and hospitality and said our goodbyes.
I walked a few blocks to my hotel, the Four Points Chicago, by Sheraton. If every hotel I stay at this year is this
nice, you’ll never hear me complain. I put my leftover steak in the fridge, asked them to send me up some toiletries and promptly passed out on my laptop trying to write this blog. I spent the better part of today making travel arrangements for the coming week so I apologize for the delay in posting. I’ve been stuck in the hotel all day trying to get this all taken care of. Since I have no silverware, my lunch was a steak lollipop.
Issue of the moment: how to get to Cleveland, OH between 5/19 and 5/21. I was planning to go to Columbus on the 17th but there is no bus to Cleveland (I’d have to go back to Chicago or find a way to Toledo) Any thoughts?
- The Groupawn
84 Comments
84 Responses to “Getting Around the Windy City”
Leave a Reply
A Day in the Life of the Groupawn
The Groupawn on the Today Show
Like The Groupawn on Facebook
About Live Off Groupon
Want to learn more about Live Off Groupon? Learn the rules, read the FAQ, and learn more about Josh Stevens.
be sure to thank our wonderful sponsors:
Thanks Scott – I understand your skepticism but my resolve is unwavering…see you at Disney!
I have Central Texas on lockdown and friend all over that would love to help. Just let me know if there is anything Team Texas can do to help.
I LOVE the steak lollipop picture, that seriously cracked me up. HA!
Hi Josh!
I’m patiently waiting to read more of your blog! Are you planning on posting more soon?? I work as a nanny and the kids at work are asking me a few times a day to check to see if you have written more
My friends and I would love to show you around SF when you get here.
Good luck!!
E
I am very happy to see your unwavering resolve, because you will definitely need it.
Again, I’m rooting for you. I wanna see this happen for sure. Unless there is some legalese preventing this, I have a feeling you’re gonna get about $200k off the sucker when you’re done: $100k from Groupon and another $100k from the ridiculously awesome book you can (and should) write about the whole experience. You can just do an autobiography over 1 year of your life and it will be sheer amazingness.
Can’t wait until you get to SoCal – I’ll take you to a burger place out here that is amazing, and was the place I filmed my LoG business video, so we’ll be set.
Hey there,
Check out Megabus. Runs direct from Chicago to Toledo and then onto Cleveland. Pretty cheap!
I’ll pay my own way – you are lucky I just saw this now or you would have gotten a mouthful but I think everyone else has accomplished that task for me! GO JOSH!!!
I got your back for Austin, TX!
Hey Josh, I just stumbled across this, and I have to say that this is the craziest thing I’ve ever heard of, but it’s about the coolest too!! When you make it to Indy give me a holler. I’ll be glad to help in any way I can. Groupon rocks! Woot woot!!!
LOVE IT! Love your attitude, love groupons and love the support that you are getting! I know San Diego is a long ways off, but I would love to help if ya need it!
I’ll pay my own way… you should understand the challenge before you make stupid uninformed comments!
Josh,
You’re off to a great start and I love the bartering you’re doing with people and the stack of Groupons you have in hand.
You’ll have turned yourself into quite a salesman by the time this is over – and it sounds like you have a great ability to make friends quickly. This should be a great journey for you – filled with many stories.
I imagine the people who cross your path will have some great stories to tell as well – very human ones about helping a total stranger overcome a somewhat amusing challenge.
All the best – you sound like a perfect person to succeed at this challenge!
Cheers,
Ken
I own Mudflats Bar & Grill just north of Columbus and we have a Groupon out there! If you want I can see if we have anyone heading to Cleveland that you can ride with…let me know!
JOSH,
Man, you seem to be having a GREAT time. I know how difficult it can be leaving all you know for the great unknown, but you are doing a wonderful job so far. I am in Houston and would be more than willing to give you a hand any way I can. I would rather not post my contact info on here, so I am shooting it to your email!
Good luck buddy!!
I’ll pay my own way – Wow, you need Jesus. This is called bartering, look it up!
You are gooooooooood. I see why they picked you. You were also my video selection. I’m sure you’ll figure out a creative way to get where you need to go. You stand to lose too much if you don’t buddy!
See you soon in Atlanta! The sky’s the limit here!
I’ll be glad to help in NYC if/when you get here!
Would love to take you out if you get to NYC!
We’ve got you covered for Atlanta, GA.
Great gig!!! I’m looking forward to reading about your year! I love groupon and love bartering…. this is going to be fun to follow!!! You need to start making a phone book… put my name down for when you hit San Antonio, I’m a photographer, so I’ll document your visit here in style!
go josh!
when you make it to SF please let me know. would love to be a part of your adventure!!
Wow! Amazing so far. We’ll if you come to the phoenix area. I would love to help you if needed. I love Groupons!!
Coming to STL? I just tapped into this whole story via the newsletter. Was not aware of “the deal”. What a cool thing! Have fun and check in if you are coming to STL. LOTS of great restaurants and the Cardinals, what more could you ask for???
You would not believe the number of offers for help I get daily…what you see in the comments here is just the tip of the iceberg. You are all fantastic and I can’t wait for you to show me around your cities.
Just to address all the questions I’m getting about if I’ll make it to…X City…I will try! I have to figure out each day as it comes, so planning ahead doesn’t do me much good, but it is incredibly cool to see all the people all over the country that want me to come visit. I really do appreciate it!
Anything you need in Portland, Oregon, just let me know.
I LOVE Groupon and I am really enjoying your blog – first time I have seen it. We’re in Phoenix and would love to see you out here. Get them to do a Groupon for Fleming’s at DC Ranch – they have an awesome happy hour. Oh, and maybe one for a mtn bike rental – we’ll take you riding.
By the time you get to Austin, you will need a haircut! It’s on me. http://www.diazandbrooks.com
Call us 512-939-8903
Hey Josh:
Sorry to hear that Cincy is not as hopping and friendly as one would hope. It appears you will need to let people know your plans a little earlier going forward, hey? Coincidentally I am following another Scottsdale email, as happened last night, and, once again, the suggestion is great: Fleming’s is a great restaurant, known for its steak (my step-daughter used to work there). Also, they suggest a mountain bike rental and I happen to be a steward for the McDowell Mntn Preserve–one of the better places in Scottsdale to go biking (never done it, but…). Have fun.
awesome start Josh, good going
for your off bus jaunt (Columbus-Cleveland this time but could be any that megabus aint got a direct route for) you might want to advert a Groupon or two that you take them to at the destination (they pay tax/tip on top of travel of course) to be a treat for the personal taxi, a less desirable option would be to advert some Groupons at city of origin that you wont be able to use personally
the difference being, in the first case you can tweet/blog about the reward location where in the second case you wouldn’t be there to blog
(not only is it nice to hear details of places one might go to, but the extra advertisement of Groupon locations will make the real payers of your adventure, the businesses issuing the Groupons, extra happy)
and a final observation… the co sponsors include two bus systems…. neither having a mutual stop… so you will need some cross country help at at least one point… keep in mind the college circuit and their seasonal times when you plan your approximate time of departure… east coast ppl in college on west coast and vice versa means late August early September for Fall semester. then there is Winter semester, Summer semester has less but it still possible end of June. and of course ALL Holidays and spring break… if you plan ahead by at least a couple weeks you will be able to find students who are either going or will go if their meals and lodging on the way are mostly paid for
I know i said that was final but just thought, would be nice to see you itinerary on a public calendar, have you checked out Google Calendar? make a public list of your approximate time at every city you plan to go to real easy for all to seee when you will be in their area
Hi Josh,
I’m loving your blog. Let me know if you plan to come to North Carolina. My husband is an athletic sales rep and I can hook you up with some big/tall shorts and t-shirts from his samples in our basement. You will need some lighter weight clothes for the HOT summer days in some of the Groupon cities you visit. I agree with Bill, if you post your upcoming travel plans in advance, you’ll get more posts from folks willing to help you out and suggestions for cool things to do when you are in town.
Let me know when you make it into Las Vegas! I
‘ll take you to the BEST all-u-can-eat sushi you’ve ever had!
Josh, this is so cool!! With the economy nosediving, you & Groupon are proving we should never give up!! G0-GO-GROUPAWN!
Josh,
Come to Louisville, KY. My husband and I will give you a place to stay while you do the Groupon thing
Merry Christmas and Happy New Year, may all your wishes come true!
Merry Christmas! Let the new year will bring a lot of money