Kim Kaupe
Kim Kaupe (BSBA '08)

We Are Warrington | How do you stay motivated in the middle of a pandemic?

In this special New Year's Bonus Episode, marketing alumna Kim Kaupe (BSBA '08) shares how she went from being a "full-time freelancer" to being named one of Forbes' 30 Under 30, and how she's approaching 2021 with excitement and innovation.

Andy Lord

Andy Lord

Kim Kaupe: The good news is I feel like because we’re not a consumer-facing brand, I feel like I could call the company like Monkey Butt and our clients know us. They know us as humans, not so much what the entity is called. Like I literally feel like we would call the entity anything and they’d be like, well.

Andy Lord: Well, you can’t call it a Monkey Butt because there’s actually a product called Monkey Butt, so.

– [Music]

Lord: We Are Warrington is a new podcast that helps young business leaders discover what is possible by highlighting stories from the Warrington College of Business community about the University of Florida experience, business industry, insights, innovative research and more. I’m your host, Andy Lord. Today, we are speaking with Kim Kaupe, an entrepreneur, speaker, teacher and UF alumna. In addition to running The Superfan Company, a fan engagement agency focused on creating products, programs and strategies for entertainers and brands, Kim serves up street-smart business education in her weekly live series Coffee With Kim, as well as her entrepreneurship focus courses on LinkedIn Learning. You might also recognize her from Shark Tank where she secured offers from four out of the five sharks. Previously, she was named in Inc’s 35 under 35, Advertising Age’s 40 under 40 and Forbes’ 30 under 30. We are gonna be talking with Kim about business and entrepreneurship tips and tricks as well as how to set yourself up for success in 2021 and beyond. Here we go. Kim, welcome to the podcast. Happy new year. What are you excited for in 2021?

Kaupe: What is there not to be excited about in 2021? I feel like we are all ready to turn over an amazing new leaf and fill these next 12 months with so much positivity and so much of a go-getter attitude. I’m really excited for everybody to jump into this new year with maybe a little more vigor than they have in years past.

Lord: I like that answer. I agree, I think we are all excited for a change. I think we’re all, you know, getting excited hopefully about a potential vaccine, maybe life getting back to normal. I think we’re all experiencing so much that we’ve learned over this past year and moving into the new year, how are we going to take all of these different ideas, ways of moving around in the world and move forward with our lives? So, I definitely think that’s something that we should all be excited about.

Kaupe: Absolutely, and I’m really excited for our new normal and it’s something that I’ve been stressing to a lot of people lately, that we are going to enter a new normal, but I think it’s a new normal filled with amazing opportunities. I think it’s a new normal filled with gaps for people to fill through entrepreneurship and innovation. And it’s also gonna lead to a lot of forward-thinking by Fortune 500 companies and companies who perhaps in the past did not have to be as innovative or have to think as much that they will have to do going into 2021.

Lord: Absolutely agree with you on that. And you know, clearly learning about your company, I’ve just been a little bit going, “God, I don’t know what the heck, is this all gonna turn back around?” You know, you directly work with these artists, you directly work with these festivals, everything that is going on in the entertainment industry is just flipped upside down and must be tough, you know, for you, you know, and typically I ask finding motivation in times like these, and I guess, you know, how do you find your motivation in a time like this?

Kaupe: I mean, I’m excited. I feel like maybe I’m glass half full, but you know, I think one of our biggest frustrations in the business is that you’re constantly trying to innovate, and people are constantly, which I get, they have corporate jobs, they work at these big entertainment companies, their job is to keep their job.

Lord: Right.

Kaupe: Their job is to do just good enough, but not bad, but not be too risky that they like keep their job, make their bonus, get to the next year. So sometimes when you come with these innovations and new ideas, they’re like, well, I don’t wanna do that. Like, that’s way too radical or that’s way too risky or that’s way too, you know, let’s just do what we did last year. You know, let’s wash, rinse, repeat, change a couple things, do the same thing. And so, I know in 2011, when I first started the company, it was really exciting because Napster and iTunes and Spotify in 2011 was just coming over from the UK, forced the industry to innovate. Like they didn’t want to innovate, but like they had to, these external forces of Spotify, made them innovate. And so, I sort of see the same thing happening here. Like they would have been really happy to just keep on keeping on, but these outside forces, you know, this COVID is forcing them to be like, we have to rethink fan engagement and when we have to rethink. So, I actually feel like it’s gonna be really exciting. I feel like next year people are gonna be really open to new ideas, they’re gonna be open to new ways of thinking about things in a way that they just weren’t. They just were not last year because the truth of the matter is people say that they wanna innovate and people say that they wanna be first and one of the very first questions I get, like people say, “Oh Kim, have you and your team give us a big new idea.” We work for weeks; we bring back this big new idea. And the first thing they say is, “We love it, this is amazing. Who’s done it before? Did Selena Gomez do this? Has Justin Bieber done this?” And it’s like, “No, well, no, one’s done it.” Like we came up with it for you because you asked us to come up with a big new idea. And it’s like, “Oh, we can’t do it, there’s no proof.” I actually think it’s gonna be really exciting. I think we’re gonna end up doing a lot more consulting work. I think we’re gonna be doing a lot more brainstorming, a lot more helping companies think through, what does this new plan look like? What does this new engagement look like? As opposed to, “Hey Kim, we saw what you did for Mumford and Sons, can you do the same thing for us?”

Lord: Right.

Kaupe: I think there’s gonna be less of that because people can’t really do that anymore.

Lord: Yeah, the hit factory is changing. It seems like you got to sort of obviously progress and move on and do things a little differently. For you, did you come up with any new year’s resolutions? Let’s say, what’s new for you this year?

Kaupe: Let’s put it this way, I’ve had a lot of time to think. I’ve had some good thinking time, some good meditation time on what my new year’s resolution’s gonna be.

Lord: Nice.

Kaupe: I always have many, I think one that is sort of a constant is I usually try to pick one or two learning opportunities. So last year it was really reading more books or listening on Audible, you know, consuming more books. Well, the universe heard me and boy, did I have more time to consume more books. Let me tell you what. So, I have to be careful about what-

Lord: That’s right.

Kaupe: My resolution is.

Lord: Yeah, don’t do that to us again Kim, come on.

Kaupe: The universe brings it right back, you’re like, I kinda wished for this, my bad everybody. I think we always say, “Oh, you know, I need to spend more time with my friends and family.” But I think as we get into a vaccine and as we sort of loosen up gatherings and travel restrictions, it has as cheesy as it sounds, put in a really new perspective with me of how much time am I spending with my parents? How much time am I spending with my family? You know, really looking at where the time is going. I heard a really great speech the other day and I can’t remember who said it. They were saying, you know, if on average you see your family twice a year and let’s say you see them for, I don’t know, a week, that’s a really long time and most people don’t even see their family for two weeks out of the year, but let’s say two weeks. And let’s say your parents are in their sixties or their seventies and let’s say being super generous, they have another 20 years to live. You know, let’s say they live into their nineties or something like that or their late eighties or nineties. So, okay, they have 20 years to live and you’re seeing them for two weeks every year, you know, you break that down, you have 40 more weeks with them. Like, that’s it, you don’t get more time than that. So really sort of prioritizing like, “Okay, I know I wanted to do that weekend getaway with my friends and that’d be really fun, but maybe I’ll use that long weekend to go see my parents instead like that one extra time.” So just, I feel like in COVID I’ve really had the opportunity to rethink where my time allotment is going and maybe how I wanna position that going into 2021.

Lord: That’s pretty prophetic right there. That’s pretty awesome.

Kaupe: Sort of depressing. Everyone’s like, “God, what a downer.”

Lord: It’s not, it’s just you know, you say something like that and obviously my wheels are spinning now going, holy moly, you know. However, I live up here in Gainesville and my mom’s up the street and Alachua. So, I deal with her on a weekly basis because she can’t get enough of me. But you know, realizing how important that is, you know, for sure and you mentioned to me, I believe before we got started, you’re down in West Palm right now, which is your hometown, your stomping grounds, you’re down there with your parents. How has that been? Has it been great?

Kaupe: Yeah, it’s been amazing. I love Florida. I love West Palm Beach. Obviously, Gainesville always holds a special place in my heart. I was so excited because 2020, a group of my friends and I were all supposed to go to a game, sadly you know, that all got washed, but hopefully in the 2021 season or maybe 2022, who knows, we will be able to get down for a game ’cause I do love Gainesville. But I love West Palm, it was such a formidable time for me in years growing up, so I love coming back here and revisiting my roots, which sounds poetic.

Lord: No, I think that’s great. And this helps move right into, you know, your UF route. So, you’re graduating high school down in West Palm, the University of Florida is on the horizon, can you break that down for us? You know, is that your number one choice? Is that where you wanted to be? You know, how did that lead to the decision of, you know, entering UF and earning a marketing degree?

Kaupe: So, both my mom and my dad went to UF.

Lord: Go Gators!

Kaupe: While we did tour other schools and went and looked at UCF, I will say both my parents actually refused to take me to FSU to look at the school.

Lord: That happens to a lot of Gator families, we get it.

Kaupe: No, but I looked at a bunch of schools and it was really, I think Florida has an amazing program called Bright Futures, if anybody doesn’t know about it, it’s an amazing program that if you get over a certain GPA, you will get either 75 percent or a 100 percent of your college tuition paid for. I think UF was always somewhere that obviously my parents were really hoping I would go and when you add in that it was a 100 percent free as opposed to maybe some of the other schools I was looking at where you’re paying out of state fees, which are exorbitant, it kind of turned into a very easy no-brainer.

Lord: Gotcha, so why marketing? There’s so many options. What was it about business that attracted you?

Kaupe: I have loved marketing and events my entire life and I feel that it was rare in that I had a lot of friends who also attended UF that changed their major once, changed their major twice, sometimes even three times of you know, “I started on PR, but now I think I wanna go into this and now I actually think I wanna go into that.” And I was very fortunate, you know, starting from around age 12, age 12, 13, I was in the zone. I had tunnel vision. I wanted to work at a magazine. I loved magazines. I loved publishing. I loved marketing. I loved events. And it was like, that was it. It was like love at first sight, there was no other, you know, consideration or things that I wanted to do. And yeah, from age 12 to my first job, all of my internships, everything, it was marketing, marketing, marketing, you know, magazines, magazines, magazines. It was, that was the only thing I did.

Lord: I got to talk to you about Gainesville, Kim. So, you said you were a bookworm while you were here, but Gainesville is an amazing place and I always ask people what they loved about Gainesville while they were here, what they liked to do, even if it was a restaurant or a park or how you spent your free time, if you did have any, what did you like to do here in Gainesville?

Kaupe: I know, I got very lucky. You know, I graduated in ’08, so I always tell people you know, I had three football championships, two basketball championships, you know, went to school when it was, you know, Tim Tebow days and Urban Meyer and you know, I was felt like, wow, how does no one like, love this so much? It’s just the best thing ever. And then I realized, oh, most schools don’t win a national championship every single year. And so, then I realized, oh, maybe I just hit it at a good time.

Lord: There you go. And then after all those wins and championships, you realize and wake up, it’s 2008, we’re in a financial crisis. Kim Kaupe’s about to graduate. Holy moly, what happens? How did you make your way out into the real world in 2008? It’s such an interesting time and a scary time all wrapped up, again, can you address that for us here?

Kaupe: Yeah well, first and foremost, it feels like déjà vu.

Lord: Right.

Kaupe: I feel like people right now are experiencing the same thing and to quote Jake Tapper, it’s a dumpster fire inside a train wreck. You know, it’s a hot mess, like.

Lord: Yes, it is.

Kaupe: It was a hot mess in 2008. I mean, I had friends who were graduating from UF unemployed for months, months and months and months and months. And I, again, through internships and connections, the woman that I had interned for the last two years, it took a few months, but she was able to create a position at her organization, it was full-time freelance, which for anybody who doesn’t know, is basically you’re gonna work a full-time job. You’re gonna work nine to five, five days a week. But somehow through some loops of government craziness, we’re not gonna pay your healthcare, we’re not gonna give you any benefits, we’re not, but you’re gonna work full-time, but you’re not gonna be our employee and we’re not responsible for you. So, I worked at Condé Nast in a full-time freelance position for probably close to nine months before they had the overhead and bandwidth to bring me on in a proper full-time position. But it was a rough, it was a rough go. And I think that that’s kind of, it was a big learning lesson for me that thank God I had interned with this woman over two years, thank God that I had stayed in touch with her, you know, thank God that I had the wherewithal at age 21 to say, let me continue to talk to this woman. I know a lot of people who I look at their resumes and I say, “Oh wow, this internship that you did last summer, it was so great.” Like, you know, “Are they hiring?” And people go, “Oh, I don’t know. I’ve never talked to them again.” It’s like, what? “You had an internship for three months and then you just left?” And it was like, “Yeah, I left, ’cause like, you know, I just, I don’t know, got back with my own life and out of sight, out of mind.” And I’m just going…

Lord: Yeah, bad idea.

Kaupe: And I say all the time, “I have no problem with you leaving a job, I have no problem with you leaving an internship, whether it’s on bad terms or good terms but whatever you do, do not leave the people.”

Lord: Right.

Kaupe: “Leave the job, don’t leave the people.” And there’s especially no excuse when we have things like LinkedIn or Instagram or Facebook, whatever your social media tool of choice is, there is no excuse for you to not stay in touch with people. I feel like LinkedIn is such, if I could wish one thing for 2021, for anybody listening to this, I would say, if you are sleeping on LinkedIn, if you are not active, if you have not signed in, if you have not updated it, you are missing out. There is so much organic reach right now. There is so much organic networking going on. It is such, you know, I don’t know if many people know this but about two or three years ago, LinkedIn was bought by Microsoft.

Lord: Yep.

Kaupe: Microsoft has been pumping millions, millions and millions and millions of dollars into updating the technology, making it faster, making it more robust, making the analytics better. And I know tons of friends who’ve gotten connected with recruiters and jobs and opportunities or help or internships and it’s all because of LinkedIn. So, I tell people–I’m such a bully about it. I mean, honestly, like I have friends, who if I see their LinkedIn is kind of shabby, I will bully them to no end, like “You gotta clean this up. We’ve got to fix this up. It’s like having a house with a broken door, we gotta fix your door, your door’s looking like crap.” So, I actually, I have a download, it’s the first thing when you go onto my website that pops up and it’s like the five things that you can do on your LinkedIn, maybe in less than 30 minutes, 45 minutes, that’s going to set you up for success. And what I tell people is I don’t wanna hear you complain about your work or about your career or about your school for one more second until that’s cleaned up. If that’s cleaned up, complain all you want. But if you’re not gonna put yourself out there so that opportunities and good fortune can find you, you don’t have a hall pass to complain with me.

Lord: You hear that Gator nation, listen to Kim, clean up your LinkedIn. Personally, my windows are shattered in my LinkedIn house. I don’t even think I have a roof on it. Kim, I’m gonna actually go and check out your five steps towards LinkedIn greatness whenever we’re off of this. Kim, back to you. So, you leave UF, you get a job through your internship connections, where does that carry you? Does that take you to New York City to start your life up there?

Kaupe: Yes, that takes me to New York City. So, I moved to New York in September of 2008. So I graduated in May, finally left in September because all that time I was unemployed and I got that job at Condé Nast and I was at Condé Nast for about two and a half years and really just felt like I was getting to the point where I wasn’t learning anything anymore and to me, the biggest proponent of you at a job is that you’re learning, you know, you’re enjoying yourself, you’re enjoying the people that you’re around, you feel challenged, you feel like you’re working on new skills. And I just felt like I had kind of hit a block with that. And so, I ended up taking another job, very hastily, huge mistake, you know, I don’t know I was 24 years old and probably a little more flippant and a friend of a friend, again, going back to connections, I was complaining at a lunch. I love to complain at lunches with my friend saying like, “I’ve hit this glass ceiling and what am I gonna do?” And she kind of all of a sudden was like, “Oh my gosh, it’s so funny you mentioned that. I was at a dinner last night and a friend is looking for somebody at this experiential agency. You know, let me connect you with them.” I was like, “Wait, I don’t even have a resume together.” I was just complaining, my favorite hobby, like what’s going on? And long story short, fast forward, two weeks later, I accepted a job. Like it was very fast, I didn’t do a ton of research, huge mistake, there are great websites like or where you can research companies. I didn’t do that. I don’t know. I was like ad agency. I’ve seen a Mad Men episode. I’m gonna be Jon Hamm, drinking whiskey. That sounds fun, why not? And I joined this ad agency and very quickly, I mean, like in the first 10 days, I was like, “Oh no, I’m not Jon Hamm, I’m not drinking whiskey, and this is not at all like the TV.”

Lord: Right.

Kaupe: And I thought to myself, holy moly, I’ve gotten myself in a bit of a pickle. And I think the only solution to this pickle is I’m going to call my old boss and I’m going to cry and I’m going to grovel and I’m going to say, “I made a huge mistake, can I have my job back?” That did not sound that fun, shockingly. Didn’t sound like something I really wanted to do, but I was like, I kind of have no choice. And right at that moment, the girl sitting next to me was saying, “Whoa, whoa, whoa”, at this ad agency, “before you call your old boss back and cry and grovel, come out to drinks with me, I have this crazy idea. I actually think you might be a good person to help me with it.” So, I went to drinks with her. I mean, she’s basically a stranger. And I was like, “What do you got?” And she pitched me this idea and I was like great, well, statistically like 93 percent of startups fail in the first year. That’s just math because, I was like okay, great. This could be interesting, what if I start this company with this girl, it will fail, because 93 percent of startups do, but then when I call my old boss and grovel, I’ll have a really funny story that for the first two or three months, I started a company that like didn’t work. And that’s why I left to like scratch my entrepreneurial itch but now I’m back and I want my job back. So that at the time to me sounded like, well, obviously that’s the way to go, go back with a funny story, not go back with, I’m a huge idiot. And you know, that was nine years ago. And luckily, we were one of the really lucky companies that are a part of the 7 percent that don’t fail, but I had every intention of it failing.

Lord: So that is when the birth of an entrepreneur happened, over drinks with some strange friend from an ad agency job that you were not liking very much. Before we take a break, Kim, I do wanna jump into, I mentioned in your intro, you know, you were on Shark Tank. So clearly in the midst of the drinks with the friend that you’re having there, you’re birthing an idea, and somehow now you’re pitching it to some sharks on Shark Tank, what was that like?

Kaupe: Yeah, it was an amazing opportunity. I have a love, hate relationship with the show. I love it because it promotes entrepreneurship and is certainly better than people watching the Kardashians. I hate it in that, you know, it makes people think that in eight minutes you can raise a $100,000 for your company. You know, that’s not realistic, again, it’s reality TV.

Lord: Right.

Kaupe: That’s not actually how business works. You don’t walk into a meeting and eight minutes later walk out with a check. So, you know, I have a love, hate relationship, but the show was an amazing experience. We had a blast. It’s sort of the gift that keeps on giving because the episode re-airs every six to eight weeks, so I will continue to get screenshots on people’s phones or you know, TVs at home that I all of a sudden pop up on their screen, which is really fun. And the way we got onto the show is a little bit unusual than most people because we did not apply to be on the show. We did not try to get on the show. We were on Inc. Magazine’s 35 under 35 list in 2014 and as part of that list, they did a little write-up on you as a feature in the magazine and out of the 35 other companies and people, founders that were on that list with us, 34 of them had raised funds. We were the only one that was bootstrapped or had not raised any traditional venture capital. And so, one of the producers on Shark Tank happened to pick up that copy of Inc. Magazine and was reading through it and contacted us and said, “Is this a mistake? Is this a misprint in the magazine? Is it true that you don’t have any investors?” And we wrote back saying, “It’s not a mistake. We don’t have any investors; we’ve never had any investors. You know, we’re just kind of chugging along, bootstrapping it.” And they said, you know, “Well, would you be interested in coming on the show? Would you be open to investors?” And that is really how the conversations kicked off.

Lord: That’s pretty amazing. So, do you have any advice let’s say, to other entrepreneurs that are looking to pitch their ideas, whether it’s the sharks or not, you know, obviously you created a pitch, worked out. What would you say to an aspiring entrepreneur whenever they’re seeking that seed funding, venture capital, whatever it might be?

Kaupe: I would say, you know, as much as you can, do research, don’t reinvent the wheel. So do research from other organizations and what I mean by that is a lot of times people will think, “Well, I wanna go out and raise money” or “Well, I wanna go out and pitch my idea. So, let me just go to the top, you know, five VC firms that I can Google.” And instead, I would say, look at what kind of company you’re trying to start, look at what kind of product you’re trying to build and see who is similar in that space. So, if I’m a cupcake company in West Palm Beach and I wanna start a cupcake shop, maybe look at a pie shop or another bakery or a bread maker and see, well, who did they raise funds from? Or who did they get funds from? Because chances are, if someone is willing to invest in a pie company or someone’s willing to invest in a bread company, a cupcake company is not that far off. So, if you can find out who their investors were and go after their investors, you already know that they’re probably warm to what, at least what industry you’re in. A lot of VCs and capital firms will focus on certain areas, so while this firm is really known for doing consumer products, this firm is really known for tech, this firm is really well-known for health care, this firm is really well-known for fashion. So, find out who your people are and I think again, the easiest way to do that is find what might be considered competitors or close enough competitors and see what they did and copy their homework.

Lord: Again, great advice. Thanks, Kim. We’re gonna take a quick break and we’ll be back with more of Kim Kaupe in just a minute.

Lord: The new year is a great time to think about ways to better yourself. Education is a surefire way to bring about a brighter future and here at the Warrington College of Business, we have plenty of opportunities for you to do so. At Warrington, we offer multiple MBA program formats and eight specialized master’s degrees. All of which will increase your knowledge, skillset and according to a study by the U.S. Bureau of Labor Statistics, your average weekly pay. So, if you wanna invest in yourself in this new year, consider a graduate degree from the University of Florida Warrington College of Business. To learn more about Warrington’s graduate degrees, head over to the link in this episode’s description.

Lord: Welcome back to We Are Warrington. I’m chatting with entrepreneur and Warrington alum, Kim Kaupe. Kim, I wanna get back into what we touched on before the break, the beginnings of your entrepreneurial career. Obviously, you know, quitting a job to create your own business is a big step, so how did you, I guess, make that step or transition, overcome fears of uncertainty and I guess staying motivated, pursuing it, knowing that where’s my next check gonna come from? I’m only assuming that must be something that you’re thinking about. So how did you manage, how did you maneuver during that time?

Kaupe: So, I always say there’s sort of two camps of entrepreneurs, there is the camp of quit your job, follow your passion, you know, go after what you want at 110 percent or don’t go at all. Then there’s the camp of like have the side hustle, you know, test the waters, see if you can get there, you know, kind of do the corporate thing and do the side hustle. I fall into the latter camp. I’m definitely more of like, listen, if you’re independently wealthy, go for it. Quit your job tomorrow and start that cupcake business, more power to you. But most people are not independently wealthy. Most people have to pay rent or a mortgage or car payment or car insurance or whatever it is. And I can tell you firsthand, starting a company is stressful enough. That’s already stress, we’ve already got a 100 percent stress right there.

Lord: Right.

Kaupe: You don’t need one more ounce of stress other than all of the stress that the company’s gonna bring, so the stress of, how am I gonna make the car payment? How am I gonna pay mortgage? How am I gonna pay my rent? How am I gonna eat? How, that’s all on top of the regular stress from the company. So, I’m in the camp of keep your corporate job or whatever job you’re doing as long as humanly possible, so you don’t have to worry about rent and you don’t have to worry about your 401k, and you don’t have to worry about whatever else. And that’s what we did. So, we worked, we kept our corporate jobs. Like I said, I started that job in October of 2008. I did not quit, officially quit until March of 2011, even when we started the company in January. So, I stayed on for three months at the corporate job and instead worked nights and weekends, my lunch break, et cetera, just trying to hustle. And don’t get me wrong, like you’re tired, you don’t get to see your friends. So that’s why I always say whatever your idea is, cupcake shop, app product, whatever, you better love it. And I mean, love it enough that like if you lose two hours of sleep, you’re like, I don’t care, I still love it. Kind of like having a baby, it’s like, I’m sleep deprived, but I love you. And so, it was only in March I had, you know, thankfully had saved money from my corporate jobs over the years that I was like, okay, I’m gonna quit this job and I know that I have, you know, two month’s rent, you know, I have two months worth of kind of all my expenses saved up, my rainy-day funds and I gotta make this work. And I also say if you can kind of think about your worst-case scenario, it’s another really great exercise for anybody who’s thinking of starting an entrepreneurial journey or really just anything new in general. I have friends who say I’ve been working in accounting for years, but now I think I wanna be a yoga instructor. And I recommend the same thing to them, which is think about your worst-case scenario and your worst-case scenario is okay, let’s say I quit my accounting job because I wanna go be a yoga instructor. Okay, well now I don’t have that five figure, six figure salary anymore. Okay, well what does that mean? Okay, well now I can’t go out to eat as much because I don’t have that income or now, I have to downsize my apartment because I don’t have that income. And you sort of play this game like an onion with yourself. Well, what does that mean? Well, what does that mean? What does that mean? And when it boils down to, okay, I can be a yoga instructor but I’m gonna be, go out to eat less, I’m gonna have one vacation a year instead of two and I’m gonna have to downsize my apartment. And if that worst case scenario to you still sounds pretty good, like that’s doable, I can take one less vacation a year and like, but I’ll get to be a yoga instructor so that’s totally awesome, then go for it. But if that worst case scenario game, you get to the end and you’re like, oh no, like , like if I become an entrepreneur I’m gonna have to like give up my fancy car and I’m gonna have to like, work two side jobs or whatever, whatever that scenario is for you, if you kind of get to the end of that game and you’re like, oh, I don’t actually wanna do that, maybe think twice, because if you prepare for the worst case scenario and you can stomach it, then jumping into entrepreneurship isn’t as scary. ‘Cause you know, even if everything goes wrong and everything fails, your worst-case scenario isn’t that bad.

Lord: Yeah, I know we’re specifically talking about you pitch an idea on Shark Tank and here’s your big idea and whether you wanted to address Superfan Company’s impact at the time, you know, more than welcome to. But you know, what I’ve learned about our earlier conversations with you is that you’re multifaceted, you kind of, you know, almost embellished the word entrepreneurship because you do so many different things that surround entrepreneurship for yourself individually. And I think this is a two-part question. Who is Kim Kaupe? What are you doing on all of those different aspects of your life and all of those pursuits that you have? And then the other side is then how do you structure your day and balance everything in order to accomplish all of these tasks that you actually lay before yourself?

Kaupe: I think at the heart of it, what I really have become extremely passionate about is having other people learn from my mistakes. And I think it’s something that helped me so much when other people would, again, kind of real talk with me and show me the warts and show me the pimples and show me the blemishes. I think maybe a more esoteric conversation, but it seems like some ways, and in life and business we’re all in this filter, we’re all in this beautiful Instagram filter that, oh my gosh, I see these Instagram, you know, entrepreneurs and their desks are so neat and like, wow entrepreneurship looks so great and filtered and sexy and wonderful and they’re happy and look at their vacation at St. Barts and wow, is that a flamingo floaty? Like all the things. And I’m more like, this is hard. And like, I haven’t seen, you know, my fiancé in a week ’cause I’ve been buried under like a project. And so, I really appreciated, whether it’s mentors or advisors or just other founders, who were kind of willing to show me their pimples and their warts a little bit and what I realized is I feel called to do that for others and to really say, here’s not only the bad parts but here’s what’s worked. You know, I’m all about copying people’s homework. ‘Cause I tried to reinvent the wheel and let me just tell you, it’s expensive, it’s costly and it’s annoying. If somebody already has a wheel, go look at their wheel, it’s better to succeed with community than to try to become a bombshell by yourself.

Lord: Right, so you’re benchmarking a heck of a lot with other folks, okay.

Kaupe: Totally, and in terms of like how I get it all done, I would say, I really am a fan of time blocking. Now it’s gotten to the point where it’s probably a little much in that like I block out, you know, eat lunch. I have an eat lunch block.

Lord: Good Lord.

Kaupe: You know, noon to one, I’m eating the lunch or I’m driving somewhere or I’m calling, you know, call mom or, you know, whatever it is. But it really does help me prioritize.

Lord: It’s actually very inspiring, Kim. For any listeners out there, Kim, can you give them a piece of advice? Do you have any specific one piece of advice that you could tell them?

Kaupe: I’m gonna cheat and give you two pieces of advice. So, the first piece of advice is whatever you are thinking about right now, whatever has been on your heart for a couple days or a couple weeks or you’ve been mulling it over in your head and you’re just thinking, “Oh, it’s gonna be so hard” or like “It’s gonna be so challenging”, I need you to take one baby step to do that, because this is the message that it’s never gonna get easier. You’re never gonna wake up one day and it’s gonna be like, “Well, now the water’s warm, can’t wait to jump in.” It’s always gonna be hard. It’s always gonna be challenging. And that’s why we do it. That’s why we show up. And I’m not saying you have to tackle it at a 100 percent, I’m saying make a baby step, the smallest, smallest, smallest of steps. Tell one other person that you’re even gonna tackle it, that you even hope to do it. Have one person that’s gonna, you know, check in on you about what about that language you wanted to learn? Or what about that side hustle you wanted to start? Or what about that whatever it is that you’ve been mulling over in your mind, take a baby step towards that. And the second thing I will say is I cannot stress enough the importance of mentors. And when I start to talk about mentors, people get all freaked out. “I don’t have a mentor.” “Where do you find the mentor?” “How do you get the mentor?” “Do I have them ask them out on a date?” Like, “Is it a yes or no? Will you be my mentor? Check yes.” You know, it doesn’t have to be this weird official thing. I have mentors that have absolutely no idea who I am. Literally don’t know I exist because I follow Richard Branson, I follow Sarah Blakely on Instagram, on LinkedIn. I get help from her. I get advice from her. She has never met me. She does not know I exist, but I consider her a mentor in the loveliness of the digital age. You can have mentors that you know, that you don’t know, that are far, that are close. So, if you don’t already have one in 2021 or you already have one and hopefully you can collect a couple more like Pokémon Go, get a couple more while you’re at it, but collect as many as you can because they’re gonna help you infinitely this year.

Lord: Incredible, great advice, Kim. As we’re getting to the close of this, I typically ask two questions and I’ll frame it this way for you, an entrepreneurship investment is a word that people hear a lot. And of course, people tend to think about investment as only being capital, but it goes beyond that. What’s something that you’re doing right now to invest in yourself?

Kaupe: Wow, I feel like every couple weeks I try to invest in myself in a small way or a large way. I would say recently I downloaded two online courses that I’m really excited to dig into. One is from a woman called Amy Porterfield and another one is from a woman called Laura Belgray and you can look up the entrepreneurs. I follow them both on Instagram so you can see that I follow them if you’re interested but I’m a big fan of continuing to learn. Like I said, not reinventing the wheel. So, I actually sign up, I probably spend, and it horrifies some people but I actually think it’s the best use of money I could think of. I probably spend anywhere from 500 to $3,000 a year on education, on learning, on courses I find, masterclasses, you know, ’cause to me, I think Mark Cuban said this quote once or it’s either Mark Cuban or Richard Branson said, “I can pay money now”, maybe it was Tony Robbins, “I can pay money now and I can learn what that person has worked on for 30 years.” So, in $500, I can get 30 years worth of knowledge or for free, I can spend 30 years trying to figure out and make all the mistakes this person made, but I’m gonna spend 30 years doing it. So, there are not many ways in life that we can buy time. I mean, famously Steve Jobs, one of the most smartest, wealthiest men in the world, sadly died of cancer. He couldn’t buy more time on this earth. You cannot buy time and that is one of the only ways I know of that you can indirectly buy time because you can buy people’s knowledge who’ve spent decades doing the work.

Lord: Love it. And finally, I know we’ve talked about this a little already and I always ask my guests about motivation. You know, I think that’s such a big part of us all staying positive, moving forward with our lives, our careers, our families, whatever it might be. It’s been so insane in 2020, I think anybody could use some advice on how to keep going during tough times. So, you know, for you, what keeps you motivated? How do you just stay so positive and so motivated?

Kaupe: I think what keeps me motivated is probably what keeps a lot of us motivated and the shocking answer to that is not ourselves. And what I mean by that is you can tell yourself you’re gonna go to the gym every single day, “Oh, I’m gonna have six pack abs, I’m gonna look like Brad Pitt, I’m gonna-“

Lord: Yeah, I’ve already done that.

Kaupe: You know, don’t we all look like that?

Lord: Yeah, yeah, absolutely.

Kaupe: We’re all Vin Diesel. You can’t see us, we’re on a podcast, we’re totally ripped and- why wouldn’t we be?

Lord: Right, of course, we have all this extra time on her hands, so.

Kaupe: Right.

Lord: I’m doing pushups right now as a matter of fact, while I’m talking to you.

Kaupe: Exactly, but it’s really easy to cancel on yourself and to not go to the gym ’cause you’re tired, ’cause you’re hungry, because you have one more email to do and you don’t go. And then of course you don’t have the six pack abs because you don’t go and you ate the cookie and whatever. But then when a friend is gonna meet you at the gym, you’re like, “Oh wait, my friend’s there and that’s real rude of me not to show up.” And then all of a sudden, you’re dragging your butt to the gym because your friend’s there. So, when I think about motivation, my biggest piece of advice and where my head goes first is you have to involve another human because you can say all day or I can say all day, “Oh yeah, I just like wake up and meditate, you know, motivate yourself.” Again, going back, I’m secretly lazy. I’m like an undercover lazy person. I need another human and chances are if you’re listening to this, it would be helpful or you also need another human to keep you accountable, to check in with you, to make you honest. So I would say what helps with motivation is tell other humans your goals, what you’re interested in, what you wanna accomplish so that they can at least ask you how it’s going. Period.

Lord: I like ending on that. Kim, it’s been so awesome talking to you today. I really appreciate all of your time.

Kaupe: Thank you, this is so fun. And I hope that everyone will connect with me on all the various platforms. I spend way too much time on Instagram. I spend probably a healthy amount of time on LinkedIn. So, I’m around and love connecting with other Gators and other people who are passionate about business and learning.

Lord: Absolutely, so follow her social media at Kim Kaupe, find her on LinkedIn, listen to her Wednesday Coffee Chats, all very fantastic stuff. For our listeners who would like to hear more about what our amazing alumni are up to, follow our updates in the Warrington Newsroom and on social media. Until next time, stay motivated and keep investing in yourself and Happy New Year!

To invest in yourself this year, consider adding another degree to your resume. Learn more about Warrington’s broad range of graduate degree opportunities at