I Flew to Chicago to Get Interviewed by ConvertKit’s CEO (behind the scenes)

So what happens when a first time author gets invited onto one of the biggest podcasts she’s ever been asked to be interviewed on? Well, I’m about to take you with me from New York to Chicago for about 36 hours to go get interviewed by the CEO of Kit Nathan Barry, on his Nathan Barry podcast. I can’t wait to take you behind the scenes.

So one of my favorite parts of writing my own book has actually been the marketing part of it, and now that my book is out, I’m just so excited that all of the podcast episodes and interviews that I’ve been doing along the way over the last several months are now coming out into the world. And so several months ago when Kit asked me to come and speak at Craft and Commerce, their conference in Boise, Idaho this June, which is, by the way, my favorite business conference. They also asked me if I would want to appear on Nathan’s podcast, the CEO of Kit, and I was like, yes, yes, yes, of course. Like Nathan’s amazing. He’s such an incredible entrepreneur, and I’m also obsessed with Kit. I’ve been a customer for over eight years, so I jumped at the chance.

Originally, I was supposed to get interviewed in Boise when we’re at the conference. But then this opportunity came up where Kit asked me, Hey, would you wanna fly out to Chicago and come get interviewed by Nathan on his show before the opening of our brand new Kit studios in Chicago? And it was an easy yes for me.

So on Wednesday, April 2nd, I left my house a little before six in the morning out here, on Long Island, and I drove into the city to go to the airport, to fly to Chicago. Now, I was only a couple of minutes away from the airport when I got an alert from American Airlines saying that my flight that was originally supposed to leave early in the morning had all of a sudden had a really significant delay.

It wouldn’t be leaving until late afternoon and it wouldn’t get me into Chicago until hours after my interview. So that wasn’t gonna work. So I quickly got on the phone with American Airlines. I got a new flight, and I’m not kidding you, five minutes after I got on this new flight earlier in the day, it got canceled and so they turned around and put me on a third flight, which was delayed, but was still scheduled to arrive about two and a half hours before my interview. So I said, sure, I mean, what other options do I have at this point. I was seriously sweating whether or not I was gonna get there on time, but right now my main goal was I need to get to LaGuardia. I need to park my car. It’s so easy at LaGuardia you just like pull in, you can walk right into the airport if you don’t need to check bags, you literally walk right through security. I can breeze through security ’cause I’ve got all the things like TSA pre-check and clear and whatever else is going on and I was able to get through the airport and just like seriously, less than a minute.

From there, I still had a few hours to kill because whatever number flight they had put me on, I, it was still delayed a bit. So I headed over to the Amex Centurion lounge. I have the American Express business card and can’t recommend it more. I get a lot of perks from it, but one of the best ones is that I always get access to these lounges. So. I headed to the lounge and I actually, this is not sponsored, but I actually went to the lounge and I knocked out a, like a Kit sequence, so I created a new freebie recently, so I actually sat there and reviewed all of the copy and design for that new freebie.

Created a couple of emails that will go to people after that, and then also took a look at and edited the copy for the opt-in page for that freebie. So I did all of that while just sitting in the lounge, , trying to see if my flight was gonna get there on time. I was communicating with the Kit team the whole time, being like, it’s supposed to take off at this time like, I’m really hoping to get there on time. They had, Nathan had a really tight schedule, so I was really hoping like this whole thing worked out. I was really, really stressing and sweating it.

So after doing some work in the Amex Centurion lounge, it was time to head to my flight and get on the plane. And once I got on the plane, I thought, okay, the, like, the hard part is over. We’re we’re going, we’re heading to Chicago. I’m gonna be there on time, not only on time. I thought I was actually gonna be about three hours early and I would have enough time to go to my hotel and get changed and I was so relieved.

Then we sat on the tarmac and the flight got delayed while we were on the plane after some tomato juice serving and me sitting and reading my book and doing some work and all of this kind of stuff, we finally, they cleared us to fly to Chicago. So we fly to Chicago and when we’re in the air, I’m thinking the really hard part is over. Now. We’ll be fine. I was still going to be about an hour and a half to an hour before my interview, so I still thought I have a lot of wiggle room. I was a couple of minutes into the flight when the flight attendant came over the speakers to announce that there was no wifi available on these flights, and that they had also removed all of the screens from all of the seats. So there was no entertainment and no wifi. I had to fly without anything, which normally is not really that big of a deal, but this is a workday. It was also about two weeks before my book was said to come out, so I had a lot to do, and the moment that I found out there was no wifi, I was not thrilled. But I should have learned my lesson by now, because as soon as we got to hovering the airspace around Chicago, the pilot came over and said, “Sorry guys.We can’t land right now, so we’re gonna just circle for a while”. And by a while he meant like an hour and 15 minutes. So we circled above Chicago. I have never been more frustrated in my life. I just wanted a little parachute that I was like, can someone just like let me out? I just, I have an interview right down there like. Just let me out of this thing, you know? And the woman sitting next to me, she was so, so sweet, she like became my flight mom and she was like cheering for me. She’s like, she’s gotta get to an interview. We gotta get this girl to Chicago. It’s a really big deal. And it was just really cute ’cause she was like cheering me on the whole time.

Okay. Finally, the flight lands. But when the flight lands, I’m not kidding you. It’s 45 minutes before my interview and the place where Kit studios were where I was going to be interviewed was 45 minutes away. I was in O’Hare. If you’ve ever been to Chicago’s O’Hare airport, you know it is not easy to get in and out of it’s busy, it’s crowded, it’s overrun.

I literally sprinted off of this plane. The woman sitting next to me told me the best tip, which hopefully this helps you, if you ever go through O’Hare. But if you order an Uber and you order an Uber black, you can actually get picked up right at your terminal versus if you get any other kind of Uber, then you have to go like to a different terminal, a different section of the airport, which takes a lot of time and get picked up there.

So I paid the extra, it was well worth it. I. Ordered an Uber black, grabbed some Swedish fish in the airport, um, so that I had a snack. This counted as my lunch because in all of the delays and the circling and everything else, American Airline did not feed us anything. So I literally grabbed Swedish fish and a bottle of water.

It was the only thing I could get in that amount of time. Got in this Uber black and sprinted to Kit Studios in Chicago, Kit’s actually building out their Kit studios in this building. It’s like a converted warehouse where they’re one of the current tenants. I think in the future there’s gonna be a lot more in this building.

So I pulled up and I was told to look for this specific yellow door that had graffiti on it. They had sent me a picture and they were like, don’t worry. It’s super cool inside. And they were right. So I found the door. I was. So happy when I finally got there and found where I was supposed to go. And then Nathan Barry’s, marketing assistant, Kara came down and got me and brought me upstairs to meet Nathan, the team and to look around Kit’s brand new studio.

 So this is super cool because Kit is actually doing this thing where right now they have them in Boise and in Chicago, and they’re actually going to be building one in New York City as well in the future. So they have this thing where if you’re a Kit member like me, you can go to Kit Studios and use one of their studio rooms to record content, record podcasts, film YouTube videos, like you could do your course videos from there.

The space is gorgeous. Like there’s all these different rooms where you can record content, and I, one of the things I really loved about it was that. They created different rooms for different styles and vibes, so it’s not just all white or all dark or whatever they, they’ve done all these different ones.

There’s even rooms that have like bookshelves and they’ve styled the bookshelves to look like it’s somebody’s home. But they also very, I thought, thoughtfully left space on these bookshelves for you to be able to put some of your own things. So you could bring tchotchkes from home, or you could put your book on the bookshelf.

Like I would probably put my book up on the bookshelf if I went there to record something now. So I thought the studio space was just gorgeous, and it’s gonna be such a huge bonus ad to Kit members.

After they showed me around Nathan, his marketing assistant, Kara, a couple of other people from the Kit team, we all sat around and we talked about what is this episode going to look like?

 What were the goals? What was kind of a light structure? They essentially produced these episodes as professional podcasts do. I think one of the things I’ve learned the most about in this like media tour as my book has come out is that, people who are at the top of their game in podcasting especially, do a lot more of the planning and upfront work than I ever realized. So very naively, back in the day, I would just record podcast episodes or YouTube videos or whatever, like especially with a guest just being like, let’s just have a conversation and see where this goes. And. As cool as that is, I think it’s also really, really helpful to have a little bit of a light structure to be like, this is kind of the theme of this episode. This is the hook. Like this is going to be the main takeaway for the audience. And then this is based on that kind of where our conversation should go. And yes, of course it flows organically and, and Nathan asked me questions and, you know, maybe I said something or brought something up that he didn’t expect, and he would then follow that path.

But he would also use like the light structure of the episode to kind of come back to center, um, and also maybe to just guide which follow up questions that he asks. So I’m definitely learning a ton in the process about how to go about doing these kinds of episodes.

 So after we sat down with the Kit team and went over the episode, it was time to get down to recording. So Kara, Nate’s, uh, marketing assistant, got the room all set up, made sure they had like six different cameras from all around the room. There’s audio all over professional lighting, like it’s a whole thing. So we sat down and talked for maybe an hour, hour and a half. Um, going over our episode, we talked about all kinds of things from, you know, how I’ve built my email list in kind of a boring niche to all of the things that I’ve been through, um, in the last couple of years since I started my own business from me having brain surgery, to my dad getting leukemia, becoming his caregiver, my dad passing away, my mom being killed all within a year. And so we talked a lot about this from the aspect of like how not only do, how do you keep going right in your business, um, but also how did I share this with my audience as I was going along and how being vulnerable with my audience kind of accidentally led to growing it.

 After my interview with Nathan, I got to chat with him for a little bit and then I had about 45 minutes to kill before Kit started, um, their opening party. So they had a big party welcome party for Kit members who were located like in and around Chicago to come and check out their brand new space. And they invited me to stick around and meet everybody. So I popped into one of the studios that they had that was open and got down to work. So it was pretty awesome. They have wifi, like they had all the stuff set up. Um, so I was actually able to check in with my team, see what was going on for that day, let everybody know how the interview went, and knock out a bunch of quick book tasks cause you know, I was two weeks out of launching my first book, so. I had a lot of things going on, a lot of media requests, um, a lot of coordinating with people, asking them to share about the book, writing copy for them to share about the book, creating social assets, um, for me to share about the book. So, so many things going on that I, right at this moment was like, I’m just soaking up every single moment that I can to pop in and get work done when I can.

After that I got to see everybody come in and see Kit Studios for the first time and it was so cool to watch them like just light up as they saw how beautiful this space was. So they had an opening party where they had drinks and they had food. Um, lots of cool Kit merch to give away. I got really cool t-shirt and a hat and everything, and people were able to actually pop into the individual studios and start playing around, test it out, or some people actually took the opportunity to sit down and record content. Like I saw a guy interview Nathan for a couple of minutes, which was really smart.

 A couple of the people at the party came up and recognized me and was like, aren’t you Sam Vander Wielen or like, aren’t you Sam? I think I follow you on Instagram. You have a book coming out called When I Start My Business, I’ll Be Happy. I was like my marketing is working guys. People know what the book is called. People know what the book is like, what it’s about. I was so excited and everybody was so nice. I even convinced a couple of them to sign up to go to Craft and Commerce, um, Kit’s Conference in Boise in June because I was like, I’m telling you, it’s like the best conference, it’s the best business conference I’ve ever been to. Super actionable. And I’m speaking there, so like. You should come. So it was so cool meeting everybody in real life. I always get so inspired by meeting other creators and learning about all the unique businesses that everybody has.

 Even though I’d only planned to stay for an hour, I actually ended up staying at Kit’s party the entire time and then took a cab back to my hotel, the Sofitel Chicago, and I was starving.

So that day was a horrible day for me in terms of planning and, and like meeting my basic needs. I didn’t drink enough water, I didn’t eat enough. I just, the whole day got thrown off by such a hectic travel schedule. And especially right now with everything I have going on with launching this book, like it’s really important for me to be taking care of myself and making sure I’m hydrated and eating well and gently moving my body every day just to like keep my stress in check and make sure I’m satiated and nourished. You know? And this day was just one of those days where you get to the end of the day and you’re like, I did not do what I needed to do to be nourished, and I’m feeling it, and I knew I needed to do something differently.

Honestly, that night when I got back to my hotel, I ordered Sweet Green and had it delivered to my room because I had to take a shower. I had to get outta my clothes ’cause I don’t know about you, but when I fly it’s like I, I’m counting down the seconds so when I can take a shower and so, and I’m convinced that this helps me to not ever get sick after flying because I will always change my clothes and get showered. And so I just wanted to shower and like have food delivered.

And so I ordered something through Uber Eats to be delivered by Sweet Green. It took forever. It was way past the time that it was supposed to be for it to get delivered. It was just way too long. And by the time that it got there, have you ever reached that point of hunger where you’re so hungry, you’re not hungry anymore?

 It was like, I think all the stress of the day, the stress of the travel of like really feeling like I wasn’t going to make it on time, and then having to arrive straight at Kit Studios and go right into the interview even though I had planned to get there, you know, get to Chicago so many hours early and get changed, get prepped for the interview. In terms of just things not being like me, not having an opportunity to eat and, and to be able to take care of myself. So I was not proud of that. And I went to bed really frustrated and really upset with myself that it was just like I had, I had let things get a little bit too crazy.

I hadn’t eaten enough when I had opportunities. I hadn’t drank enough when I had opportunities. And so I went to bed thinking like. I can’t do this much anymore because I am at a really busy point in my life when the book is about to come out and I really need to do better and to get better care of myself.

 So I woke up really early the next morning, Thursday morning, and I thought, I’ll check my flight first thing, I wanted to make sure my flight was on time, and as of now, it was perfectly on time. So I walked over to my favorite coffee shop near the hotel that I usually stay at in Chicago, called Big Shoulders, and I really wanted a very good cappuccino..

Then I saw that they had a tasty little egg sandwich situation going on, so I grabbed a cappuccino and an egg sandwich and I just sat and relaxed for a couple of minutes, um, before I needed to walk back to the hotel, get my stuff and head off to the airport. So I went back to the hotel, got my stuff organized, packed all my Kit stuff. And then I reflected a little bit on my interview the day before with Nathan. .

I think one of the things that’s the hardest while I’ve been writing the book, editing the book, and then now promoting. And well first like learning how to market it and making the plan for it and then actually being hardcore promoting it since January is that you still have a whole business to run..

So it’s like you have this whole other thing. And the book it’s, it’s weird because when you write a book and you own a business, you’re like it, there’s this tendency, I think to like to treat them separately. If you’re writing a book about business or related to what you do or something like that, like something that supports your business, your book is essentially like a low ticket product, right?.

 And I’ve never, I’ve never had a low ticket product before. I’ve only ever sold two things. I sell the Ultimate Bundle®, my legal program that gives you like all these legal templates and trainings, and then I sell legal templates, downloadable contracts, and so. This has been my first thing. That’s not only not legal, but it’s also like a considered, you know, kind of like a low ticket offer..

It could be an entry point to my business for a lot of people. And it’s something that’s really high value to me. Not necessarily high value, you know, financially, um, because people purchase the books elsewhere obviously, and so we see very little of that. , I. Yeah, it’s just been like, it’s been a journey trying to figure out how do you, how do you balance both and then treat this like it is part of the business, but value it at the same time, but also remember that it’s like not going to be a moneymaker. So it’s more something that you’re doing because you really, like, either want to write a book like I did, or you really wanna teach in that way, which I did that I hope that the book is like super, super helpful to all of you. You know, that I, I just want it to be like your guide to building your online business. That’s why I wrote it. And so that’s all very exciting. But then also. You know, I have a multi seven figure business to run, so there’s like, that doesn’t stop. It’s like a whole thing that’s going on in the background. So luckily I have a really good team and that’s really helpful.

 I mean. I think like, I would say that it’s not only that we have a good team, but it’s also that our team is probably working a lot harder and, and different, like even just like differently than we normally do. Like we don’t normally operate in chaos and we don’t normally hopefully context switch so much. Like, I just think, like right now, my director of operations, Lindsey, and I just keep saying like, we just feel like we’re like juggling all the time and like you’re just like constantly switching between all these different things and , I’ll speak for myself that I sometimes feel like I’m juggling so many different things and that I don’t know if I’m doing anything particularly, it’s not like, well, but like, to my, the best of my ability, but it’s also leaving me feeling very exhausted. Um, you know, this is the period, right? This is the, this is the head down period, right?

Before, as I’m talking to you, we’re 12 days out from the book coming out, and so this is the time period when you’re like. Alright. Like all systems go, but it’s also the time period. Oddly enough, it’s the one that I like feared the most, but it’s also the one because I was like, oh, as it gets closer, I’m gonna be so nervous that it’s coming out.

But now that we’re here, I actually feel calmer. I was saying this to people at the Kit party last night, like I feel now that I did even like a month ago. Because at this point, like you just reach a point where you’re like, I’ve done what I could, you know? And so I feel like me, the team, everybody who’s supporting the book, the publisher, everybody’s kinda like laid it on the line and at this point it is what it is.

 It’s also my first book and it’s my, my first time writing it, my first time, you know, writing one, uh, my first time marketing one. And my first time that my audience is seeing something from me that’s not legal, and so I’m kind of giving myself grace or I’m trying to, then I’m like, Hey, you’re doing this for the first time, right?

So you have to remember that like when you, when you are doing something, you’re putting out some sort of creative project of any kind. It doesn’t have to be a book, or it could even be starting a business. And you might be looking to other people as how they’re doing, who are not creating their first, you know, iteration of this thing.

I feel like that’s, you know, just to remember, like, that’s like an invitation for you to not compare yourself to how other people are doing it. You know, like I’m, I’m speaking at Convert Kit’s conference in June at Craft and Commerce. I’m giving a keynote alongside people who have New York Times bestsellers alongside people who have multiple big five book deals.

I’m like, I just got my first one. This is my first book. Right. I wrote it while my mom died, and so it was, it’s a, I don’t know, just like trying not to compare my chapter zero or chapter one, two. Everybody’s like chapter 15 kind of thing. Yeah. It’s just important to remember as you’re, as you’re endeavoring on all of these creative things that.

 It’s, that’s not really the comparison to make. It’s like, look at how far you’ve come, look at all of what you’ve done. Right. So being there last night, getting to be interviewed by Nathan Barry, who I’m like, if I ever got to be interviewed by him, like getting to hang out with him, he is such a nice guy. Getting to hang out with his team who are all delightful, right? Like the whole Kit team is so nice getting to be in that room and meet other creators. I’m always just so inspired by all the cool things that you’re all doing. So. Yeah, there’s just a lot of, I’m trying to like soak it all up because there’s a lot here for me to look at of like, oh, look how far you’ve come. Not like, look how far you’re from other people. You know what I mean? So with that, let’s go catch a cab and go to O’Hare. Time to go back to New York.

So after I got all ready to head to the airport, I checked my flight one more time. And what do you know? I got an alert that my flight got canceled, not delayed, just straight up canceled. And without my permission, they automatically rebooked me on a new flight. But the problem was that this new flight was going back to New York to JFK’s airport and not LaGuardia, which is where my car was and where I had parked.

 And these airports are not necessarily, they’re kind of close in distance, not in time when you’re dealing with New York traffic. In rush hour, so I really had no choice. I called the airline. There was no other flight available. There was no flight going to LaGuardia until late, late at night on Thursday. And I didn’t wanna stick around. I wanted to get back, um, to New York. And so I headed to the airport anyway. And what do you know? The new flight that they put me on to JFK got delayed.

 So I killed some time, walked around the airport. I went to Barbara’s bookstore where I always go. Um, I tried to imagine my book possibly being in that bookstore one day. I saw a lot of books of people who I know who I’ve like met in this space and who I know are with my publisher and everything. So it was just cool to like walk around and see all the different books and imagine that being possible one day. And I finally got on my flight.

We get on the flight, and again, again, I think, okay, I’m on the plane. Like my butt is in the seat. I am on the plane. This thing is going back to New York. But no, no, no. We were all, literally every single person had boarded. We put everything away. Everything was all situated and then they come over the speaker and they say Our flight is delayed, um, at least two hours. And the problem now is that our pilot is over his time.

So if he, if the flight got delayed that much, then he won’t be able to fly us. So he’s like, so I’m negotiating with the people on the ground to try to see if they can let us go out instead of one of the other flights because I’m not gonna be able to fly if they make us wait.

 So we sat there for about 45 minutes while he was allegedly negotiating, only for him to come back and say, oh guy, what do you know guys? They said, no, they won’t let us outta here. So your flight is canceled. Everybody has to get off the plane. They need to find you guys. All a new flight and they need to find a new pilot. And so like everybody off. And so at this point I was just. Besides, I’m just so frustrated, right? And so like we all get off the plane, I go back to a lounge, hang out for a little while. I had a lot of minestrone soup and, and uh, it was one of the only things that didn’t have meat in it. And so I go back to the lounge and I hang out, um, for a bit, try to get some work done, and then they announce that they put us on a new flight that was taking off in about two hours.

Finally got on that plane and I just kept texting my friends and everything. I’m like, I do not trust that I’m going to be home until my feet are literally on the ground in New York, and I also had this new problem to deal with that now I’m headed to JFK, so how the heck am I gonna get from there to LaGuardia? So our flight finally goes.

It was a really bumpy flight, not pleasant, but luckily this flight had wifi. I worked on stuff for my business the entire time. I wrote a lot of copy. I answered emails I got into slack and help the team with any of the little things that they were waiting for me to approve, uh, or to look at. And I knocked out, luckily, a lot of things, even though I told my Director of Operations, Lindsey I did all of this without an, without a stable surface the entire time.

So I got all of that stuff done and we finally landed at JFK after a white knuckle of a flight, I got myself into, uh, another Uber and it took about an hour to get back to my car at LaGuardia. Finally found my car, threw my suitcase in the trunk and headed home. Did the two hour drive back home, absolutely exhausted.

 It was so awesome though. So worth it. And such an incredible opportunity to go get interviewed by Nathan. The travel, which obviously had nothing to do with them, was just a nightmare. So. This season and this busy season of my life, I was just like, man, this really threw me for a loop.

But I think the positive side was that it did throw me into this like the next several days, just like really getting, I don’t know, refocused on taking better care of me and my health and my self care and my basic needs. And so it was a little bit of the rock bottom that I think I needed to hit to be like. I thought I was doing actually pretty good and now I realize I needed to take better care of myself.

So that’s a wrap on my trip to Chicago to get interviewed by Nathan. If you’re listening to this on my podcast, you can head over to the link in the show notes to watch this blog over on my YouTube channel. It’s probably a lot more fun to watch, but I really appreciate you being here, and if you haven’t yet, make sure you go and order my brand new book, When I Start My Business, I’ll Be Happy. I teach you all my marketing strategies and secrets in it. For you to build a profitable and sustainable online business.

 Thanks so much for listening to the On Your Terms® podcast. Make sure to follow on Apple Podcasts, Spotify, or wherever you like to listen to podcasts. You can also check out all of our podcast episodes, show notes, links, and more at samvanderwielen.com/podcast. You can learn more about legally protecting your business and take my free legal workshop, Five Steps To Legally Protect and Grow Your Online Business at Samvanderwielen.com and to stay connected and follow along, follow me on Instagram at samvanderwielen and send me a DM to say hi.