337 Shaped to be an Entrepreneur – Zipkick CEO Jason Will

What you will hear in our discussion with Jason Will:

  • Emotional Journey of a Young CEO
  • Travel in Your Own Style – Zipkick CEO Story
  • Want to Raise Entrepreneurial Kids? a Young CEO Story
  • How to Deal with Setbacks and Succeed
  • Personalize Your Travel Search – Zipkick CEO Story

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More about our featured guest Jason Will

Jason Will is the co-founder and CEO of Zipkick, which personalizes the travel search and booking experience. As a former consultant who traveled on a weekly basis, Jason wondered why every search required interacting with scroll bars, sorting features and check boxes to find the best travel options. Prior to starting Zipkick, Jason was shaped to be an entrepreneur as a result of working for several family businesses prior to completing his BA from the University of Minnesota. His passion for technology led to seven years of global software deployments spanning from large scale ERP systems to Business Intelligence.

*My ReLaunch moment came when my Grandfather passed away. Losing a best friend was hard enough, but even more so, I completely shut down mentally. Shortly thereafter my employer who previously offered to sponsor my MBA, rescinded the offer. This came after months of preparation, passing the GMAT and applying to schools. This is where the story begins.*

Full Transcript

00:01 Joel: On the show now as promised, CEO and co-founder of Zipkick, Jason Will. And if you're not familiar with Zipkick it is the travel app that you just need to have. What it does is it personalizes the travel search and the booking experience. And I'm sure we'll get into Zipkick a little bit more and a little bit later on in the show but for now Jason, buddy, welcome to ReLaunch.

00:30 Jason Will: Thank you so much for having me here, it's an exciting time to talk travel and obviously to join you and the audience.

00:37 Joel: Well, it's exciting what's going on with Zipkick and I know you'll just kind of weave that in to the ReLaunch experience and then we'll get into that here in just a minute. What I generally do is I ask our guests to zero in on the relaunch that has been the most transformational for them and then we just kind of unfold the story from there, and we'll do that with you here in just a few minutes Jason. But if it's okay with you, I wanna start off the show with a little quick piece of what I like to call “take away gold” and you're an expert in the travel industry and you work with a lot of travel bloggers so let me just kinda come out and just ask you this: What would you say is the best piece of advice that you can give to the [01:21] ____ world business traveler?

01:24 Jason Will: So it's interesting, the whole travel landscape is changing every day and it's only gonna change even more but for the business traveler, especially the traveler that's on the go, interacting and trying to find experiences from your mobile device is very difficult today and being compartmentalized. So what ends up happening is, is that you don't have a personalized experience across all of these different things that you're trying to do on the road. So what I would look for as a business traveler are, what are the tools that fundamentally make my life that much easier and discover the things that I haven't discovered before. So it's really trying to live like a local when you're traveling.

02:06 Joel: Because you…

02:06 Pei: Live like a local.

02:08 Joel: Live like a local.

02:09 Pei: Yes, so you don't have to feel like, “Gosh, I'm in this new place. I can only be in this hotel room; otherwise, I had to research a whole… Spend a whole bunch of time to figure out where I wanna go, what I wanna do?” Huh?

02:25 Jason Will: That's correct and we can stay in a hotel in any city in the entire world, that's the easiest way to travel. Try to put yourself outside of that comfort zone and find things that only locals do or know about and try to have those conversations because those are the most enlightening things that you discover when you're traveling.

02:43 Joel: Absolutely. And you were yourself a [02:46] ____ world business traveler so that had to have been frustrating for you earlier before the launch of Zipkick when you were kind of looking around, bumping into this wall and that wall in various towns, states, and countries trying to figure out “Gosh, what do you do for fun around here?” so that's…

03:02 Jason Will: Yes, and even more so than that is, as a business traveler, I was stuck on the tarmac all the time with delays, and at that time I was living in Chicago, which O'Hare is notorious for delays and things of that nature. So when you're stuck on a tarmac you only have your phone 'cause you don't have access to WiFi, you don't have anything else at your disposal, so when I would use these tools that are out there today I'd have to use every single mobile app just to figure out what it is that I'm looking for, there wasn't one centralized place who knew what I like as a traveler and I just thought that that was crazy.

03:37 Joel: I got you. I got you. Well, we're gonna talk a little bit more about that later on in today's show. Zipkick, but before we get into that let's kind of back up and talk about Jason's relaunch. How do we need to get started for today?

03:51 Jason Will: So we can back up to the first job that I ever had and…

03:56 Pei: Yes.

03:56 Jason Will: Things were going extremely well. It was actually an internship that led into a full-time position a couple days after graduating from the University of Minnesota. They put me on a fast track program, a lot of advancement, a lot of opportunities and then it was one of those corporate environments where all the top managerial positions were taken by the veterans, which is fine, but it limited the amount of opportunity you had up to a certain point. So that's when I started trying to figure out, do I go back to school and these sort of things and was able to negotiate a pretty significant offer to go back to school on a full scholarship and started preparing for that process and you get your hopes up really high, and all that stuff is kinda coming through and as I'm getting to the tail end of that process applying for schools and whatnot, my grandfather had passed away.

04:51 Jason Will: And up until that point I never lost anybody that close to me in my entire life and I would say I've actually never had a best friend since then because of that fear of loss, it changes you the rest of your life. And shortly thereafter is when the company hit the downturn in 2009 with the loss of jobs and everything that was going on with the economy. Both of these things, when they rescinded the offer to send me back to school and the loss of somebody that close to me in my life, it was probably the most mentally disruptive moment at any point in time that I ever could have expected to happen, and second of all it changes your outlook on life pretty immediately.

05:42 Joel: Go ahead, Pei.

05:43 Pei: How did you deal with that, Jason at that young age and…

05:47 Jason Will: You can never prepare yourself for a loss of somebody no matter what advice you had or how many times you've been through that, it never gets any easier. But my boss at the time said something that was very monumental and it was, “Think about it from his perspective don't think about it from your perspective as your own loss, think about it as maybe he thought it was time to move on to a better place. It's not always about you and the time you spend with that person, it's… You really have to understand it from the other side of the fence”. And that really stuck with me the rest of my life because we can be very selfish in moments like that and say, “Oh, it's my loss and it's my issue and I feel a void.” But really you need to put yourself on the other side of the perspective and say you know what maybe it was time and maybe this is what that person ultimately wanted.

06:43 Joel: So let me ask you this. You said in some of the material that you shared with me that, when you lost your grandfather, that you pretty much shut down mentally. So I'm just curious here Jason, how much of a challenge was it for you to again reopen your thinking and your mind and learn how to put yourself on the other side of that?

07:11 Jason Will: It was incredibly difficult for a long time. And you take a step back and you realize how many blessings you have every single day, to be surrounded by a family that loves you, to be surrounded by friends that are there to support you. It's really the strength of your community and the people that you surround yourself with, that was the focal point going forward. And one of the lines that I always say to people here in San Francisco is, “You're only a strong as the network you create around yourself.” And every single day I commit myself to try to make that community stronger. And we're taking the same approach with Zipkick as well is the community approach and really propping each other up and having that full support of one another. That is gonna carry you through the darkest times.

08:03 Pei: Yeah. We heard this many times either in our business relaunch, house relaunch. Any time when we go through either hard time or transitioning to the next stage in our life the support, and you said it so well, “We're only as strong as the people around us.” So yeah. If we talk about the relationship between you and your grandfather, what do you remember about him that… Can you tell us a little bit about that?

08:33 Jason Will: Sure. We could be here all day talking about the amazing things of who he was and what he means to me even today, but I would say that his roots in Eastern Europe, mainly Poland, fighting in World War II and coming over to the States midway or probably a third of the way through his life, very hard work ethic from day one. It's a guy who spoke either six or seven languages, never had a formal education, always did very hard work. He actually came to the States as a shoe maker, and worked his way up through that regard, used that as kind of a side craft, worked in a butcher shop. Just everything was very hard working from day one. So that work ethic that I have today is a 100% related to the fact of how he was and what role model he became for us as kids. More so than that, every single day that we would have a babysitter it would be him. My parents never were big fans of putting us into a day care or some other means for us to be looked after. So when you're with him every single day and you get to talk to him and he inspires you and you just have such a close role model as a kid. There's nothing that can replace that because when you're in the day care, you just so look at that individual as somebody who takes care of you temporarily, where as a grandfather or a figure like that, that's a permanent fixture in your life.

10:09 Joel: So I'm curious about this what did you learn about yourself, or what did you relearn as you experienced your own grieving and growing process moving forward in your life, business life of course, but personal and spiritual walk as well?

10:27 Jason Will: I really didn't realize how much paying it forward would come back full circle, because I've always been more of a giver than a taker in all of the business relationships or even personal relationships since I was very, very young. And it's in that moment that people start taking care of you which is very unexpected. And as an independent and a very stubborn person at times, it's a little hard to deal with actually, because you're not used to being the center of attention, you're not used to people being there to support you as frequently as maybe your daily life entails. But it just, it made me realize that the relationships I had were 10 times stronger than I ever thought or could have imagined they actually are.

11:20 Pei: So at first receiving that support, that love, was a little difficult for you?

11:28 Jason Will: It's very, very hard for me to receive in general, and I try to be as independent as possible, and handle these things internally. And Joel, to your point earlier about mentally shutting down, everybody hits a tipping point where they can only handle a certain amount of things internally before they have to rely on other people. And I think that's kind of the point that I got to, was after internalizing everything from the very beginning and all problems that have happened up until that moment I could deal with those internally. This was the tipping point that put me over the top that I had to rely on that community, not because I wanted to but because I needed to.

12:09 Joel: Oh, I love that. Not because you wanted to but because you needed to. Pei, do you have something you wanna add?

12:15 Pei: So, Jason. Talk about this relaunching to your current business, how did that come to, and what did you do before?

12:25 Joel: Right.

12:26 Jason Will: So, it's been a long journey to get to this point. About four weeks after I got the news that that tuition sponsorship or that scholarship was gonna be taken away, I gave my four-week notice and that's why I moved to Chicago. Networked out of that position and landed a new job in Chicago four weeks later with a technology consulting company. And that led to traveling every single week, and that was where I really got a better understanding of what are all the tools that exist today in travel, how are people using them? Especially in the business environment but then also, when we took our leisure trips on the weekends, what tools were people using for that as well. So, that was kind of the first purview into the travel space and then, really being a frequent traveler dealing with issues at the airport, and lost baggage, and all these things that come with traveling. It's part of life. And did technology consulting for a total of about five years, and it got to a point where I just… I really didn't wanna work for somebody else anymore. And it was a dream of mine to be an entrepreneur since I was a little kid, and my parents had been entrepreneurs pretty much their whole life.

13:46 Joel: What did you do when you were a little kid? I love to hear these stories of kids.


13:51 Jason Will: Oh, my gosh.

13:53 Pei: Lemonade.

13:54 Joel: Yeah.

13:54 Jason Will: Hold on to your seat.

13:56 Joel: Okay.

13:56 Pei: Oh-oh.

13:57 Jason Will: So, I started installing Koi ponds and landscaping bushes and stuff between the ages of about 12 and 14.

14:07 Joel: Nice.

14:07 Jason Will: A family friend of ours needed a Koi pond dug out, so I did that you know yard work. Was a baseball umpire. I basically mowed lawns.

14:20 Joel: Sure, yeah.

14:20 Jason Will: I ended up… My mum was working for a grocery store at the time and she got me… I can't even tell you how many random jobs. They had watches that they would sell, they had loyalty programme cards that they needed people to sign up for, they had different characters like the Nabisco characters, craft characters that you would walk around in, in the grocery store, and interact with kids in all this. Probably the best job I ever had was a pawn shop appraiser. So, people would come into the pawn shop with their items to sell, and I would give them a fair value on it and intake their items.

14:57 Pei: By the way, how does that work? I mean, I guess they teach you how to appraise the value of those things.

15:04 Jason Will: I've always been into these things, Pei.

15:06 Pei: Okay.

15:07 Jason Will: I literally… And Scott will tell you when we get to that point, but I love collecting things, I love knowing the value of… What are all the trinkets and I've always been into that stuff, right? So, a lot of these things I just knew, because I've been involved with them for so long, especially electronics. But you do searches on Google or eBay or Amazon, if you don't know the item… Things like power tools and all these kind of stuff, I don't know… At 16, 17 years old, I wasn't the expert in power tools and things of that nature, but you just basically figure out whatever the retail price is or whatever you can get it for on the show floor, and you offer them somewhere between 40 and 60% of that value.

15:50 Pei: You should have taught Joel, 'cause I think he sold our power…

15:54 Joel: What did I sell?

15:56 Pei: You sold our power tools at… Was it $5?


15:59 Joel: At our yard sale? Let's not talk about that. Let's not talk about how much I got scaved on the yard sale, pricing of our valuable merchandise. But anyways… But it's gone now.

16:16 Pei: Right. Sorry, we got sidetracked. But that was very interesting. So, you were saying that was one of the lower jobs you did as a kidpreneur.

16:31 Jason Will: Yes, and I just always… I would be that kid that would run to his parents with every single idea I've ever come up with my entire life.

16:40 Joel: Love this.

16:41 Jason Will: And some really, really incredible ideas. I mean there were two ideas that actually were turned into products that I had before the age of 15 years old, which is really insane to think about because those were kind of the moments I look back now, and I'll be turning 30 in August. It's just, I can't believe that I thought of those things before, years before they actually were built.

17:09 Pei: What I am also impressed with is, it sounded like your parents were very supportive, and they just allowed you to explore many possibilities during that time, too.

17:22 Jason Will: They gave us everything as a kid, and when I say everything, it's not monetary things that they had to give us, it was the compassion that they showed us, the way that they treated other people. My parents have worked in a grocery business for over 40 years, both of them. And they worked days and nights just to make sure that we didn't go without. And more so than that when we're playing sports as a kid, I remember taking road trips to Canada, Toronto, Canada, driving from Minnesota which took us 16 or 18 hours by car. They didn't ever do anything for themselves. They always did something for us. They were at every event, whether it be for school or outside of school, with our sporting activities they never missed a single step along the way. And you think about that into your adult years, you remember those moments as that they were always there for you in every facet. And that just has completely made me into the person I am today. I owe everything to them.

18:26 Joel: One of the things that I can recall that someone once told me, and I forget who it was, but in relation to kids having entrepreneurial dreams and expectations, let your kids take action on them, regardless of if they're eight, if they're 10, if they're 12, let them explore through that. And what he said is, “Your kids will never be as cute as they are right now.”


18:56 Joel: So…

18:56 Pei: They can sell anything, huh?

18:58 Joel: And they can. They absolutely can. I remember my neighbor just the other day had a lemonade stand outside our house when I got home, and the very first thing I did was I went and I found money, 'cause you got to… You just gotta do it. They're never gonna be as cute as they are right then and there, so you might as well let 'em explore their entrepreneurial aspirations now.

19:27 Jason Will: Absolutely, and you see it on the Shark Tank today, right? In the first handful of seasons, you never saw kids as entrepreneurs. And I'll never forget, there was one kid that went on the show and he was making bow ties. What kid at that age… I think he was 12, or 10, or something like that. This kid started a bow tie business, and Daymond John actually ended up investing in his bow tie business, because he was just so passionate and he loved it so much.

19:54 Joel: That kid was also featured in Success Magazine.

19:57 Jason Will: I didn't even know that, but it doesn't surprise me at all, because the thing is, the kids today, especially the ones that are passionate, they have all the tools around them to make it happen. Back in the day it was a 100%, because your network that you got your business off the ground. Today, you can reach people around the world 24 hours a day through social media and other means, and it's really an incredible thing how you can expand your business.

20:24 Joel: Well, what's exciting to me is, we were growing up in an area… Not in an area, in an era of, kids are now experiencing podcasting and when they get to be teenagers and in their 20's and so forth, a podcast, or a videocast, or a combination of the two will be just something that they grew up with in their culture. And so, it will be, “Well, of course I have a podcast.”


20:51 Joel: And there's kids age eight, eight and nine, that have their own shows.

20:58 Pei: Wow.

20:59 Joel: These days. I heard an interview with an eight-year-old podcaster just the other day.

21:06 Pei: Very cool.

21:07 Joel: Okay, so coming in for a landing on this, wanna respect your time, also wanna respect our listeners' time, but okay, Zipkick. What can… Talk about the end user experience, and why we should have it on our phone?

21:24 Jason Will: So, couple different things. When you think about Zipkick, you think about it as really the most personalized way to search for what it is that you're looking for that is really the premise of why we built it. Specifically, when the app launches, and we're just a matter of weeks away from announcing you know the public release of that, it's gonna be for hotels. So imagine you go to search for a hotel in New York City, and we've all been through this. Okay, you go on one of the existing sites, and you get a 1,000 hotels, and then what do you do? You start clicking through boxes; you start moving scroll bars; you start sorting the page in different ways. And it takes you forever to figure out what it is that you're actually looking for.

22:09 Joel: Right.

22:10 Jason Will: And we believe that, no, that's a complete waste of your time. We should know who you are. We should understand what your preferences are, what your social demographics are, what loyalty programs you're a part of, what is your purchase history, all these details and all this critical information that you're giving us, let's use it on your behalf to personalize that search. Not sell out your data to a third party, I'm not interested in that business, nor are we ever interested in that business. Just strictly use your information and everything we collect to personalize your search better and better every time that you come and use Zipkick.

22:48 Jason Will: And that's really the premise of what we're building is, is that, we want to be the one-stop shop for travel, and especially into the future as we do other things as well, and just really not treat you like a new customer as everybody else does. Treat you as part of the community and the people that love to travel as much as we do, and really help each other get up and go a little bit quicker.

23:11 Joel: And Pei just pulled out her phone as you're…

23:13 Pei: Yeah, I got the app right here and I realize it asked me questions before it actually pulled out the choices. Yeah, that's exactly what you said. So, in the future, right now, I saw some hotel recommendations, so in the future there will be other recommendations as well, right?

23:36 Jason Will: That is correct. So we actually are gonna be expanding into a number of different things, and I'm sure that you would love or you would like to apply this to other things, but we'll announce these things as we continue to build it out. We're focused on really getting the hotels right. Hotels, you get presented with the most amount of options.

23:58 Joel: Right.

24:01 Jason Will: Even relative to restaurants, or events, or any of these other kind of things. Hotels are really the hardest to decide because there's just so much variance, right? You have boutique hotels, you have independent hotels, you have, you know, conglomerate hotels, you have all these different groups of hotels that you're not even aware of that exist that might be better for you than some of the ones you're used to staying at. So, we wanna inspire you to check out places that fit what it is that you're looking for, and suggest that for you proactively.

24:32 Joel: Very well said. Appreciate, appreciate that. Gosh Jason, thanks so much for being on today's show, really appreciate your time. Zipkick, and one more plug for you, I know we were talking right before the show, we started recording, that you were look, expanding to travel bloggers, and that's really where you saw a lot of traction. So, let's talk about travel bloggers, and people that are blogging about travel where they need to connect.

25:06 Jason Will: So, we actually brought in one of the world's top influencers in travel, Mr. Scott Eddy, who was previously on your show.

25:15 Joel: Yes.

25:16 Jason Will: And, you know, really through him as our anchor, and a lot of his preexisting contacts, we've built out this really incredible community of travel bloggers. And, the best way to connect with us if you are a travel blogger, or you wanna get more involved, and you really wanna be a part of what we're building out, you can definitely message us on Twitter. Our handle is @zipkick. Or on Facebook. It's always @zipkick on all the platforms. Or you can just go ahead and email us community@zipkick.com and engage with us. We wanna have that conversation with you. Scott always says it, he goes, “If it doesn't make sense in the digital world, it doesn't make sense in the real world.” Meaning, talk to us just like if you ran into us at a travel conference or something like that. We wanna meet people. We wanna have a real engaging conversation, and you know, we're here to help. And people that are passionate, we wanna hear from you.

26:17 Joel: Fantastic. Passionate listeners, that's the ReLaunch nation. Jason Will is our guest today. All of the social media hotspots will be included in the blog article, and show notes that accompany this episode. Appreciate your time today Jason. You're welcome back here on ReLaunch anytime. Have a wonderful rest of your day. Bye bye.

26:36 Jason Will: Thank you.

Connect with Jason on Twitter, Facebook, LinkedIn and his website.

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Joel Boggess

Keynote Speaker | Corporate Trainer | Award-winning podcaster I help teams ignite their courage, take bolder steps, and get greater results. Together, we create possibilities that bring empowerment, meaning, and financial impact.

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