Discover the Unexpected | My 12 Minutes in Chicago

I've never actually been to Chicago, so this is a first for me.

It's not cool, man. It's not freezing, man.

I generate heat. Let's get on the plane. Hello everyone, it's time for me to travel again. I usually don't like traveling that much, takes me away, but if it's important and I feel like I can have an impact, I like getting out. So this week I'm heading off to Chicago. For Sage Summit. I'm going to be doing a couple of speeches on raising capital and marketing, as well as some Hangouts with Stephen Kelly and a whole bunch of other fun stuff. We'll see what happens. And you guys get to join me for the journey. I'm almost ready to go. I like making sure that Nina has a nice clean place to come back to, so, you know, did the usual— empty the dishwasher, clean up all that stuff, left her a note. Last time I left a note and she didn't see it. I had to tell her that I left a note because she always misses me, and I miss her too. There's that note. You see that bright yellow thing? She cannot miss the note. So just packing up. I've got everything in these two bags that I'm gonna need for my trip. Alex is here working, focused. And here's Nina saying, "I'm gonna miss you." Me too. Check in at least a couple times a day or Nina's gonna have serious depression. So I gotta add that to my list to make sure— don't laugh, Alex!

Sunita gets depressed. Rosanna with me, if we don't see each other a lot, she gets angry. She gets angry with me and like hostile even though she misses me, and then I give her a hug, you know, little kiss, and it's all better.

She melts.

But women react differently to when they love someone and they miss them.

Why are you wearing a sweater, Alex?

Because I will say why. You keep this room below 58 Fahrenheit, okay? First of all, I find it ridiculous. It should be in Celsius, but besides the point, it's 58. So I had to borrow this sweater from you because wearing jeans, socks, a t-shirt during the summer is still not enough. And you're wearing shorts and a t-shirt.

Yeah.

It's not cool, man. It's freezing, man.

I'm just hot-blooded. What can I say? I generate heat. It's good to work in the cold, Alex. Finish packing up, grab a cab and head to the airport and see Chicago. Looking forward to meeting some of you guys there too. YouTube needs to know Alex heard his cry.

Okay, save it.

And I didn't hear my cry. We'll go this way. You want to take the elevator? Okay, we'll take the elevator.

No, let's go, let's take the stairs now.

Alex hurt his crotch.

Just on principle.

Not on principle. He needs to injure his crotch even more. Jesus. This is where I do my stairwell rant. I had a stairwell rant the other day.

Let's hear this awesome rant.

Inspiring, I hope. Alright, just arrived at the airport. Passed out in the car. Nice relaxing drive out here. So, I'm ready to go now. Refreshed. Let's get on the plane. Alright, made it in, got through customs, had to take off my shoes. I have the yellow ones now. When I had the all-black Vibrams, I could get by without taking off my shoes, I thought it was socks, but now I can't get it. So, getting hungry, gonna get some food, review my presentation. I'm doing a session tomorrow on raising capital, so I'm gonna go over my slides one more time, make sure I got everything good, and get ready for the plane. First stop, Tim Hortons. This is my first presentation. Raising Capital. Don't worry about the board, I gotta get in that long line. Yeah baby, Chicago, here I come. So just landed in Chicago. Of all the places that I've been to in the US, I've never actually been to Chicago, so this is a first for me. One of the things that I like doing, as I've talked to you before, when I travel is meeting up with fans, subscribers, subscribers. I'm just getting to know them, see who those people are face to face, see who you guys are face to face, shake some hands, learn about your business, see who I can help. And one of the things I experimented with recently— let me figure out where am I going, baggage claim I guess— is having fans pick me up and take me to the airport. Usually before when I travel, when I would go, I'd take a cab, right? Take a cab to the airport, from the airport. And so I started trying something new where I meet with you guys, subscribers. So Adam, one of my YouTube subscribers and Twitter of followers is going to pick me up at the airport here and take me to my hotel, and we're going to chat about his business all the way on the drive. So I get a ride, he gets some free consulting, I get to meet a fan, and everybody wins. Way more fun than just taking a cab. So I'm going to look for Adam, and I'm excited. All right, I found Adam. Apparently Canada is not international. That's messed up. I don't know why. We're at the wrong terminal. So here he is, Adam. Tell us about yourself. What do you do? So I'm a Twitter I work with a couple of clients and we just, we get the word out about people's company on Twitter. And where can people find you? I'm at @oadamjune on Twitter. Cool. So yeah. I like it. We're gonna ride to the hotel and talk some biz. Alright, well that was cool. Lots of fun. Good talk. Took almost an hour to get get into town because of traffic, but it was good. Gave us a chance to really chat it up and learn more about his business. Gave us some good advice. I hope that we'll— we started off on one path, one little project, and evolved into an entire new business for him, and I'm excited to see where he goes. I am here at my hotel. This is the Palmer House, so I'm gonna go check in and see what happens. I like these old elevators. Alright, 13th. Where's 13th? Whoa! I think I'm on the wrong side. Wrong side. 13 is over here. 13, 13, 13. Let's see what we got here. It's a good-sized room. Queen bed? Nice. Looking good. So I'm gonna get settled a little bit, take off my backpack, and, uh, practice my speech. But I think first I'm gonna go get some food. I'm hungry. It's what, 6 o'clock here, which means it's 7 o'clock, or maybe it's 6:30. What time is it? Oh, it's 7 o'clock already. It's 8 o'clock my time. I haven't had dinner yet. Food. And then back home, practice my presentation. I got this crazy idea on the airplane for what I'm going to do, something I've never done in a presentation before. I'll see if I still like it tomorrow and have the guts to do it. Now that I said that I have to do it, we'll see though. We'll see how I feel in the morning. Uh, yeah, so I gotta eat. So that red square is me. Apparently I'm supposed to head up— what's the name of that street? State? State Street? And down Michigan Avenue and see the Magnificent Mile. Head across the river. That's the advice from the concierge. So I'm going to give it a shot and see what I see. Get some food. It's interesting that people don't jaywalk here on the main streets. I feel like if I was in New York, I just feel like I want to jaywalk and nobody's doing it, so I feel like I shouldn't. I got to act like the locals, at least until I'm comfortable enough to break the rules. But Chicago, why don't you jaywalk?

Send me pictures.

What's the big deal? Yeah, send me pictures.

Adam?

Okay, so north of the river people will jaywalk like crazy, but south they don't. Still trying to figure it out, but it feels good to jaywalk again. So I didn't find anything that really appealed to me, though I think I'm kind of on the wrong streets for restaurants and food and stuff. I gotta eat something and get back and practice and maybe meet some people in the lobby, so I'm just gonna go to Chipotle. Kind of boring, but at least you know it's good and relatively healthy. So, need some food. So they don't have Wi-Fi in Chipotle. I thought Chipotle always had Wi-Fi. Maybe it's just in Canada that they do. I don't know. So I got it to go. Got my bag. I got a steak big bowl with the works and a bag of chips with wok. And I'm gonna head back to my hotel. It had a pretty funky lobby, my hotel. I was feeling it. Lots of workspace. So I head back there, pull out my phone, see if I can catch up with Nina, a little bit of tweeting, maybe some work while I eat, and then head back to the room and practice my speech. I'm liking Chicago though. Pretty nice night and pretty scenic place. I don't know where that silver bean is. Is it a bean? That silver That guy is an angry cop. That silver thing everybody takes pictures with, I don't know where that is, but I don't really have a lot of time to explore and test it out. Top priority is to rock the presentation tomorrow. I'm here to have an impact, otherwise I'm wasting my time. So I gotta make sure I'm on my game, super prepared, and I gotta chow down and then practice, practice, practice, practice. Here we go. Got back to the room, found some nice stuff on my bed from Sage. It says thank you. What's inside? I got some water. I need that actually. Got some popcorn. Oh nice, I almost stopped at a popcorn place because I was feeling some. And what's this? Oh, it's a brownie. Nice. Let's check out the card. Thank you for speaking at Sage Summit. Please enjoy this inscription as a token of our appreciation. Signed, the Sage Summit team. Feeling it. All right, time to practice my speech. Get a good night's sleep and wake up tomorrow and crush. So quick update for you guys. Practiced the speech. Super pumped, super excited, super happy. Can't wait for tomorrow. The downside is there's this crazy screaming baby next to me and it's been screaming for a couple hours. I think finally fell asleep. They can't move me to a new room because it's fully booked, but they, they got me some earplugs that I'm gonna, I guess, try out. Hopefully, hopefully the baby does not cry so I get a good sleep. A bunch of you guys ordered books, which I'm super grateful for, and so the last thing I'm gonna do before heading to bed is record some thank you videos because that was one of the bonuses, and I just really appreciate all you guys who are willing to kind of pre-order a book now that's coming out in December. I mean, you get a lot of cool bonuses alongside it, but really appreciate the support. So I'm going to record some videos. Eric, how you doing, brother? I'm here in Chicago. It's 11:15 PM. What's up, Rishi? Thank you so much for ordering the book. It means a lot to me. Hey, Zaino, just wanted to do a quick video to thank you for buying the book, pre-ordering it. It means a lot to me. All right, that's it. Nina just came online, so I'm gonna say quick goodnight to her and then head to bed, wake up tomorrow to rock it.