Jon Hayes: [00:00:00] If there is a deal to be had, why not you? Why shouldn't you be the one to bring that deal to the company, or if there's, you know, a problem to be solved, why not you?

Andy Molinsky: [00:00:17] Welcome to From the Dorm Room to the Board Room, a podcast where we provide insights, tips, and inspiration for college students and young professionals, so they can make a really successful transition from college life to the professional world and beyond.

Andy Molinsky: [00:00:34] My name is Andy Molinsky, and I'm your host. I am also a Professor of Organizational Behavior and International Management at Brandeis University's International Business School, where we record and produce this podcast.

Andy Molinsky: [00:00:54] Jon Hayes is the founder and CEO of RewardStock, a travel startup that helps travelers book trips with frequent flyer miles and travel rewards points instead of cash. Jon comes from Raleigh, North Carolina. He's a graduate of Princeton University with a Degree in Economics. Jon was a former Wall Street investment banker with eight years of mergers and acquisitions experience at Citigroup. But then, he left Wall Street to launch his first startup RewardStock, which is this travel site that we talked about, which was featured on Shark Tank where Jon secured an investment from the influential investor, Mark Cuban. So, Jon, thanks so much for being on the podcast.

Jon Hayes: [00:01:37] Thank you for having me.

Andy Molinsky: [00:01:39] Tell us about your current company. So, let's start there. Just give us a quick sense of what your company does. And then, we'll get into all this.

Jon Hayes: [00:01:49] Sure. I think you did a good job in the intro. We help travelers basically go anywhere in the world they're trying to go as cheaply as possible by maximizing the earning and use their flyer mile, credit card and hotel reward points to pay for those trips instead of cash. And the short, kind of, basic principle of it is that you can go pretty much anywhere you want to go for pennies on the dollar. The way that you do that is by being very strategic in kind of planning for how you can get, sort of, the 4% of little cash. That can be difficult if you're trying to do it by hand.

Andy Molinsky: [00:02:35] So, what's an example? Like, just, can you give us - I don't know - a recent example of someone who got a really cool deal on your site?

Jon Hayes: [00:02:41] Well, just in the last month or so, we helped people save over $100,000 on travel. So, we've got lots of examples. A simple one is we sent someone to Hawaii a week or so ago. They were flying to go visit -- this is a -- you know, they're trying to go visit their daughter in Hawaii who is there for school. And they were saving, you know, saving as many points as they could in order to save in cash. And they thought it would take them another two years to get all the points that they would need, you know, to do that trip. And they signed up to find a trip. They later had a trip going. And the way that we were able to help with that, our system helps you find ways to use your existing points that you, in many cases, are probably not aware of using points. Those are cool travel hackers that-

Andy Molinsky: [00:03:40] Wow, cool, very interesting. So, you didn't start out there. I read your bio. You went to Princeton, graduated with a Degree in Economics, and joined Wall Street. Take us through your story. So, you're at Princeton. How did you get from Princeton to Wall Street? What was that like? And then, we'll go from there.

Jon Hayes: [00:04:02] Yeah. So, when I started at Princeton, I got a very different career path in my own mind. I thought I was going to be premed for a while. I thought I was to going to be pre-law. And it wasn't until I had to declare a major in my sophomore year that I kind of got into the economic side of my academic career.

Jon Hayes: [00:04:28] I've taken an economic course, really enjoyed it. I loved kind of the concept of analyzing incentives. The foundational business economics was appealing to me, and that kind of kicked off my interest in economics. I was happy with my -- you know, with that as a major, and I thought of researching what would people do when they graduate from college with a Degree in Economics.

Jon Hayes: [00:04:53] Two of the big career paths out of Princeton are management consulting and investment banking. And I, then, joined the Pre-Business Society and was the president of on campus. And the more I learned about investment banking, the more you want. And so, I started networking like crazy and, eventually, got a job offer. And internship is extremely important in investment banking. And I really just started there and jumped in kind of head first right after college.

Andy Molinsky: [00:05:34] So, what was it like to be an investment banker? You're there for eight years. That's a decent amount of time. Did you like it? What was it like?

Jon Hayes: [00:05:44] I did, yeah. So, you know, I really was obsessed with finance when I heard -- you know, the more I heard and learned about investment banking, I was kind of one of the nerdy kids who would watch the movie, Wall Street, you know. And, really, as I watched it, I really kind of got into the ethos and how you end up working on Wall Street. So, I loved it.

Jon Hayes: [00:06:17] And, you know, when I started out, I was this single guy in Manhattan, and really just focused on trying to make an impression in my job. So, it didn't bother me at all to work, you know, the crazy hours. I, actually, kind of brought home the challenge of being able to do something that other people find difficult or impossible, and, in particular, something that I was always good at in that hazard environment that has spoken to me.

Jon Hayes: [00:06:53] And, yeah, you are correct. And I had a lot of time to work on Wall Street. Most of my last years, you know, as far as the same time I did lasts after a year or two. But in my life, I had a long-time career. And for a while, I really did enjoy all of the stress and high-pressure, you know, crunching the numbers, and all that kind of stuff. And, also, I got married and started to have, you know, our priorities that started kind of the same time I left.

Andy Molinsky: [00:07:27] You know, it's funny. I've, obviously, never been an investment banker. I know people who are. People talk about sort of stresses you're talking about. Can you paint a picture just for like, you know, for people listening, you know, what's it like to be -- like, what's that stress like? Can you maybe give an example of a time that you were super stressed, or someone might be super stressed in your role there? Like, what's the stress about? Can you, sort of, paint a picture?

Jon Hayes: [00:07:58] Sure. I'll give you an example of one deal that I worked on. So, this was a deal where our client was a very large company based in France. And we were advising all of the potential acquisitions. And, you know, as an analyst or associate in investment banking, a lot of your job is just working in PowerPoint and Excel. In Excel, you build a financial model where your analysis is what is going to drive the decisions made by the most senior people at this company. But you do all the work in Excel, kind of figure out what the numbers are, and basically put it all into a neat PowerPoint presentation. And that's all your responsibility as an analyst and associate.

Jon Hayes: [00:08:56] And part of the stress is that every number has to be 100% accurate. And, you know, you can't have hypos or anything like that because what would happen is, you know, to the point where you can't have a comma out of place because if you do, and the CEO is like looking through the book, and there's spelling error, then they start to question the accuracy of the numbers. And if they start to question the accuracy of the numbers, they don't trust your analysis. And as an advisor, your credibility falls apart. So, it's incredibly stressful to put together a 50-page PowerPoint presentation where there is zero room for error.

Jon Hayes: [00:09:43] And on top of all that, there is usually a very tight timeline for you to produce all this work and almost always requires to be working long hours and late hours. So, this one particular deal, we were I was preparing the book for a board meeting, and we found out about a board meeting, and had some changes, external changes, in the scenario we were developing that needed to be updated and run through the analysis. And basically, we had two or three days to do it. And, you know, in context, that's a very, very short time. Normally, you would want to have like a week or two to kind of getting that mix and things like that.

Jon Hayes: [00:10:46] So, for three days, I worked in the office without sleep. And I ate two meal over that entire three-day period. And, you know, starts pulling all-nighter after all-nighter. And I went home, and showered, and came straight back to the office. So, that's the type of environment that we're in. At the end of that three days, like, you know, we basically just send the book to our clients in France, and that was the first opportunity I had to sleep was once the board meeting was over.

Andy Molinsky: [00:11:29] I could see why you started a travel website.

Jon Hayes: [00:11:36] Especially to get away.

Andy Molinsky: [00:11:36] So, actually, that's a good segue to my next question, which is, you know, bring us from sort of the tail end of your time on Wall Street to, you know, to creating RewardStock. What inspired you? How did you do it? That's a serious pivot. You know, bring us through that.

Jon Hayes: [00:11:55] Yeah, absolutely. So, the genesis of starting the company was really around the time that I got married. My wife and I spent this amazing honeymoon where we flew first class to the Maldives and stayed for eight nights in a $1000-a-night over-the-water villa. And, you know, the resale cost of that travel would have been more than $40,000 if we had paid cash. And because we, you know, had figured out these strategies with rewards, it actually cost us $200 in taxes and fees.

Jon Hayes: [00:12:32] And so, not only did we have this amazing first-class honeymoon,  but I also kind of came away from that experience feeling like this was something that I wanted to make sure I got every time I traveled to be able to get, you know, this kind of amazing savings but, also, something I thought, you know, many people in the country want to do. And the real epiphany was that there was nothing particular for me that made it possible for us to get that amazing $1000 honeymoon for 200 bucks if not only for my uncle who worked for the airlines as part of that. It was literally just planning out of strategy and executing it.

Jon Hayes: [00:13:21] And the hardest part was fund base, you know, looking at the different award charts for all the airlines, figuring out who would fly the rounds that we needed and trying to find different prompts of what different ways we could approach earning those points, what credit cards we should be using, all of those types of things.

Jon Hayes: [00:13:42] And I saw off the bat that if you're doing it by hand, you know, it's at least three weeks to figure out, even after, you know, having done this for a few years before that that a computer software would figure out in seconds. And I felt like if we could just build a software to do that, sort of, hard thinking for you know, it was going to democratize somebody's opportunity to make it accessible to people that don't have the time, or patience, or, you know, experience of reading travel blogs, you know, and spending months of kind of time learning how this stuff all worked.

Jon Hayes: [00:14:23] So, that's going back to my honeymoon was the moment where I felt like, you know, there's maybe something here. And the same time, you know, many years into my investment banking job and starting to get to a place where my job was less and less about, you know, doing the analysis that I really loved. It was more, you know, becoming more bureaucratic and, you know, kind of more senior management type of stuff. And my wife and I had just gotten married. So, you know, we were thinking long term that Manhattan probably wasn't the location where we wanted to put down roots. And so, all this stuff kind of circled around at the same time and, you know, kind of, you know, decided if I was ever going to try something crazy like quit my job and launch a startup, now is the particular time to do it.

Andy Molinsky: [00:15:17] That's a great story. So, tell us, I can't help about ask about Shark Tank. What was that like? You know, just give us a feeling for what it's like to be on Shark Tank, and what did the experience give you.

Jon Hayes: [00:15:37] So, the show. I told the story earlier about that deal where I didn't sleep for three days and how much pressure that was. Shark Tank is more pressure. It's amazing and how intense the whole experience is in part because, you know, it's a very long process. The first thing that happens too, when you want a startup and start telling people, "Hey, you know, I believe that this company could do X," if they think it's a good idea, you know, I find that in the reaction, the response that somebody will give you in the very early stages is, "Oh my gosh. That's a brilliant idea. You should go on Shark Tank."

Jon Hayes: [00:16:27] I heard that so many times in the first year or so from friends or, you know, friends of friends when they find out what I was working on. And I just kind of became one and into it. I just listed, you know, almost like by reflex because it seemed like such an improbable thing, and it's not typically, you know, kind of like something that I would say is in my nature. I'm not really, you know, the person who is looking for the spotlight. So, you know, I just kind of keep my head down and try to get good work done.

Jon Hayes: [00:17:05] So, it was never really a real option for me, in my own mind, but one day, we actually got an e-mail from one of our users that said, you know, "Hey, I'm a captain producer for Shark Tank. And I love to hear your product, and I think you should apply." And so, we have that around the office for a couple days as a joke thinking that we were kind of getting, you know, some catfish or something like that.

Jon Hayes: [00:17:41] But it was kind of planted a seed. I looked into it a little bit and, eventually, decided on you're not going to lose a lot by, at least, applying. And we got a really good response to our application. And then, we got moved further in the process. And that kind of kicked off this whole Shark Tank journey, which, you know, like I said, the best single word, actually, to describe it is it's just intense. It's not for the faint of heart.

Jon Hayes: [00:18:11] You know, if you make it through all of the process, that kind of the process, if you make it through all of that to actually get on the show to pitch your company, you know, butterflies is not the term, right. I mean, I brought four t-shirts to my showing of the Shark Tank. And the one that I wore when it aired, I only wore one because I've sweat through the first three, just to impress. So, it is very intense.

Jon Hayes: [00:18:54] You're pitching your business. And always, you know, for founders, that's always kind of a personal thing. But you're not pitching it to just any investors, you're pitching it to celebrity investors, who could have, you know, valued impact on your business, to put it lightly, and, you know, typically you're looking for capital that you need to grow your business.

Jon Hayes: [00:19:17] So, you've got to pressure of just creating pressure, and you've also got lights and cameras in your face. And, you know, you realize that this is going to be something that the whole country sees. So, whether you do it well or you flop, the whole country's going to see that. And so, you know, it's just so intense to have so much rising on it where it is all in your hands, at that point. If you do well, it can be tremendously beneficial for your business. And if you do not do well, then, you, personally, and your business will suffer consequences. So, it's very intense.

Andy Molinsky: [00:19:58] So, you got a deal with Mark Cuban. Have you been -- I mean, how involved is he? I'm curious.

Jon Hayes: [00:20:06] He's surprisingly involved. And he's not -- you know, he's not throwing stuff in our office. You know, he's not [indiscernible] for us, but we communicated about once or twice a week, and usually by email. And he's incredibly responsive through email. I don't think I never met someone who responds to email as quickly as he does. It's amazing too how much, you know, he's kind of this way.

Andy Molinsky: [00:20:40] That's great. That's actually like what you want in a partner, huh?

Jon Hayes: [00:20:43] Yeah. Yeah, absolutely. I'm very happy.

Andy Molinsky: [00:20:48] So, okay. So, we've kind of been through the big picture. I want to just ask you based on your experience, you've had a lot of interesting experiences, what kind of misconceptions do you think college students have when entering the workforce based on your experience?

Jon Hayes: [00:21:07] Yeah. So, one of the things that I kind of credit to my investment banking experience is that I really learned a lot about professional development and, you know, how the workplace operates, you know, because when you're an analyst associate, VC in investment banking, you're interacting on a regular basis with CEOs, and CFOs, and, you know, the board of directors of some of the biggest companies in the world, and they're looking to you for advice at the deep end. You spend time talking to them to learn how their organizations works, and you get a really unique, sort of, exposure to that. At the same time, you're working for one of the largest and kind of prestigious financial shop in the world. And because, you know, you're doing well, you're moving up the ranks in that environment.

Jon Hayes: [00:22:11] So, to your question of what are some of the common misconceptions, one of them that, I think, that a lot of people have, and I certainly had coming out of college, is this idea that people exceed and kind of progress in their careers purely based on merit, right? Like, you know, if you just do your job well, you'll get promoted, or if you just do your job well, you'll get paid really well. And that's, actually, I think, not true.

Jon Hayes: [00:22:45] It is true that you need to do your job well, but it's not a one-to-one correlation that if you do that that you'll also get promoted or, you know, advance in your career. And it's also true that there are people who really aren't that good at their job first day, the technical aspect of their job, but they're good at other things that help them advance.

Jon Hayes: [00:23:06] And so, there's kind of an office politics that, I think, most people overweigh or sort of undervalue, and you've got to be good at the technical aspects, but you've also got to be good at understanding kind of how the world works and how your company works. And if you can do that, if you can, at least, kind of open your eyes that there is kind of more than one candid way, I think you'll be better for your career.

Andy Molinsky: [00:23:34] I wonder how you learned that.

Jon Hayes: [00:23:37] The best way to learn that, and certainly how I learned it is by having good mentors. So, you know, if you're just starting out your career, find somebody that you just connect with. I'm not really big on formal mentor programs, but I'm really big on social network, people that you can have lunch with, and, you know, they can teach you things over lunch that you can kind of really dig your head and feel kind of an awkward, you know, mentor/mentee relationship, one that just kind of develop naturally. Those are people -- and, you know, you want to kind of find people who are doing really well in their careers you can relate to and that like you. You know, those are people you can learn a lot from, and they kind of teach you the ropes in a certain way of speaking.

Andy Molinsky: [00:24:29] So, that's great advice. Now, I would agree with you on that. We're kind of nearing the end here. And this has been such an interesting conversation. I just have two more quick questions for you. The first is about productivity. From what you've described, you've had to learn to be productive, obviously, to survive in that investment banking environment, and then, now, as the CEO of a startup, and so on, with Mark Cuban emailing you twice a week. You know, can you share any productivity tips, anything, you know, unusual or maybe not even unusual? What do you do that makes you productive?

Jon Hayes: [00:25:09] Well, for me personally, and I don't know if this is great advice, but, for me, I've always been kind of a night owl, and I've often found that I get my best work done between hours of kind of midnight and 4:00 a.m. when it's really quiet and everybody else at home are asleep. You know, from the very early days of my investment banking career, you know, having the, sort of, stamina to keep working into those late hours, you know, has always been an edge for me because I could get more done as a banker and advisor as anyone. And I don't assume that's an easy thing for everyone to do, but, you know, definitely [indiscernible].

Jon Hayes: [00:26:13] Frankly, what may be more broadly applicable is, you know, and this is something that I do hear a lot from CEOs or, you know, from folks that, you know, starting your day maybe earlier than you otherwise would because you're getting into the office at a time when it's still very quiet, and you can spend a couple hours doing work without distraction.

Jon Hayes: [00:26:44] And there's that one. And what's probably related is, you know, depending on what your role is, for me, now as a CEO and especially, you know, at a startup where we've got a small team, and we're in a high-growth kind of building-out phase, there are always more things on my to-do list than I will be able to do that day. And I found it useful for productivity, at the beginning of my day, just scoping out, "Here are the three things that I'm going to get done today."

Jon Hayes: [00:27:25] Knowing and sort of purposefully putting some of my to-do list off for another day, so that I can, at least, accomplish, you know, some stuff from that list. And then, you know, I move on to the next thing tomorrow because it's really kind of interesting productivity to have too many all in the air at the same time. You know, I think it kind of leads to a lot not getting done completely and too many things getting done kind of halfway. And that's usually not the outcome that you're looking for.

Andy Molinsky: [00:28:01] Great. I like that one. Last question for you is if you could go back in time, maybe even just as a thought exercise, go back to Princeton, go back to the 20-year old version of yourself, is there a piece of advice that you might give that 20-year-old version of yourself now based on what you've gone through, what you've lived through, what you know? And if so, what might that be?

Jon Hayes: [00:28:28] That's an interesting question. One thing that I like to tell people that I think I did looked over, over a long period of time, I think even more so, you know, kind of from the first year after graduation to, you know, the last couple years is this idea that everything that is being done in the world is being done by somebody, a person that is, you know, as human as anyone else, and all the flaws of everyone else; and yet they figured out ways to do things that are sometimes pretty impressive, right.

Jon Hayes: [00:29:22] And, you know, what one of my mentors kind of put to me in a certain way that really resonated, which is, you know, in the context of banking, you don't have to look around, look around the room for someone to give you, you know, approval or permission to solve a problem. And you don't have to, you know, sort of defer to someone just because they're more senior than you. If you have confidence in yourself, and you're in this position you're in for a reason, you know you're a smart individual, and if somebody can solve the problem, you can solve the problem.

Jon Hayes: [00:30:06] And I think just approaching things with a level of confidence that, you know, why not you? If there is a a deal to be had, why not you? Why shouldn't you be the one to bring that deal for the company? Or if there's a problem to be solved, why not you? Why shouldn't you be the one to come up with that solution?

Jon Hayes: [00:30:31] So, you know, I think, it's easy to be a nervous or to feel like it's not your place to come up with new ideas when you're early in your career. And I think, you know, some of that goes away as you spend time, but, I think, you should also kind of consciously understand that you're capable as anyone else to do whatever you need to do.

Andy Molinsky: [00:31:02] That's a great point to end on. I really like that. And, you know, thanks so much for taking the time to chat with us. I think, everything you said is just going to be very useful. And it's so interesting to hear. How can listeners learn more about you or your company if they're interested?

Jon Hayes: [00:31:22] Sure, yeah. So, our website is rewardstock.com, and hope that you check us out on Facebook at RewardStock and all of our other social media that will be on there.

Andy Molinsky: [00:31:35] Okay, awesome. Thanks so much again.

Andy Molinsky: [00:31:38] Thank you for listening to From the Dorm Room to the Board Room. If you're interested in learning more about the work that I do in helping people step outside their comfort zones and transition successfully into the professional world, please visit my website, www.andymolinsky.com. That's A-N-D-Y-M-O-L-I-N-S-K-Y. And, also, feel free to email me directly at andy@andymolinsky.com with any feedback or ideas for guests for feature podcasts.

Andy Molinsky: [00:32:09] This podcast is brought to you by Brandeis University's International Business School. By teaching rigorous business, finance, and economics, connecting students to best practices and immersing them in international experiences, Brandeis International Business School prepares exceptional individuals from around the globe to become principled professionals in companies and public institutions worldwide. Thank you so much for listening.