For this edition of Executive Summit, we’re trying something different. Instead of our usual video interview and summary, we’re trying a podcast-style audio only file, and a lightly edited transcript. This month has our  interviewer Chris Caputo talking with Holly Grimwood, owner of Kansas City Shoe Shine. Please let us know how this experiment is working by adding your comments below.


The Interview


The Post Interview Q&A


Interview Transcript:

Chris Caputo: Welcome back to Executive Summit. My name is Chris Caputo. I’m your host. Today, we have Holly. How are you, Holly?

Holly Grimwood: Wonderful. Thank you.

Chris: Nice to meet you. Holly is a Kansas City native who graduated from the University of Missouri Kansas City with a degree in Political Science. She put herself through school shining shoes at Nordstrom and branched out with her own mobile shoe shine service, boy, that’s a tongue twister, after discovering the niche market in the metro area. After graduating shoe shining … After graduating, not after graduating shoe shining, after graduation, shoe shining was put on hold to work with a non-governmental organization in northern Mongolia. Returning to the States, she landed a job as Director of a nonprofit and social service agency in Raytown, where she served for three years, rebuilding the donor base and expanding programs to better serve the families in need.

After leaving there, Holly revamped her Kansas City Shoe Shine, went full-time in 2017, and looks forward to exponentially growing her business this year. Wow.

Holly: Sums it up.

Chris: That’s awesome. Tell us a little bit, Holly, about, why shoe shining? How did you get your start with that? What was the inspiration? We talked a little bit. I’ve got a little information, but I want to let you have the floor here and share with us that story.

Holly: I grew up with a dad who is in sales and traveled internationally, and his very first job at 10 years old and in Emporia, Kansas, was shining shoes, and I still have his original shoe shining box today. When he would come back from his trips, he would bring back a bunch of these cool souvenirs from South Korea and Thailand, but the only way I could get those souvenirs is if I shined his shoes, and so child labor at a young age. He taught me the attention to detail and the importance of taking care of your products and taking care of your belongings, and so I grew up just learning how to do it and expecting that everyone else did it, too.

When I was in college, I was looking for a job, and I waited tables and did all that, but I really wanted to do something where I could have more interaction with people and I found a job at Nordstrom shining shoes, and they taught not only great salesmanship there, but just how to take care of your customer and putting the last finishing touches that people like. That was while I was waiting on the stand for about three hours a day, waiting for people to come to me. I got the idea of just going to them, and I’m like, “Well, you know, if it would save everyone’s time, I could just come to you,” and they’re like, “Yeah, that’s a great idea.”

Chris: Wait, in the store? You mean like-

Holly: Well, my customers that were coming into the store, I would ask them, I’m like, “What would be easiest for you,” because they’re like, “Sorry. It’s been a while since I could get out this way. I know. I have all these shoes,” and I was like, “Well, next time, why don’t I just come pick them up?” I got the idea of doing a mobile shoe shine job at that time-

Chris: Wow.

Holly: And tested it out and did it and found this niche industry that people liked and did that through college.

Chris: On average, how many hours were you pulling out in Nordstrom while going to school, and how many shoes did you actually have to shine per week? That’s intense.

Holly: I was working about four days a week at Nordstrom and I was also waiting tables still.

Chris: Wow. Did you have a full-time schedule, too?

Holly: Yes, and I was going to school full-time. I had probably about two hours of sleep every night on average-

Chris: Wow.

Holly: But I’d be doing homework in the kitchen at the restaurant or on the shoe shine stand and going to school. Then, my senior year, I started doing woodworking, as well, which led me to Mongolia. I seemed to have a problem with scheduling and interests. I was doing it all and trying to get my degree, so I decided that I was just like, “Well, I might as well do things I like while I’m working.”

Chris: Then you went for Political Science. We had a interesting conversation backstage. Why Political Science? What’s the story behind that?

Holly: Well, everyone has a dream of being something when they’re a kid.

Chris: Sure.

Holly: I had always wanted to be the first female Speaker of the House, and I was always into the politics, listened to radio and read newspapers and got into these high intensity conversations with my dad about the political environment at 13 years old, and it was either that or be on SNL, Saturday Night Live, so it was one or the other, equally insane really in so many ways.

Chris: Sure. Sure.

Holly: Political Science, the goal was to do pre-law, go into law. Just I liked doing things that challenged me, and I kept getting introduced in other things that interested me, but also challenged me. I was just going as the doors opened. I’d just go through and keep going until something worked out, and that’s how I got involved in so many things.

Chris: I know I’m still trying to understand some of the … There’s some technical stuff here with the shoes, so tell us about … You have this wooden box that you built. What is that about? I was so heartbroken you didn’t bring it today. I was like, “Where’s that shoe shine box,” but not the actual with the supplies in it, but the stand.

Holly: Since I’m mobile and I’m one person, I couldn’t very well have a big shoe shine chair with a dolly and a truck and try to get that all out by myself. It would be an entertaining show, for sure. I, with some help, designed a box basically that folds out, and you attach the back of the chair, you attach the handles onto it, a drawer pulls out, and you’ve got the place to put your feet. It rolls up, and it’s like a rolling suitcase. That way, you can take it to events and take it in a elevator, and it’s not this big, cumbersome thing.

Chris: Was that your woodworking …

Holly: Mm-hmm (affirmative).

Chris: You did that by yourself? You designed it and-

Holly: Well, I designed it with some help, but we built it. It’s walnut. I’m very particular about my wood that I use.

Chris: Nice. That’s awesome. That’s fascinating. To get to know you a little bit more, you mentioned your parents are pretty significant part of your life. Who inspired you with, as an entrepreneur, you went to school, you graduated, you found … You came back. We’ll get to the nonprofit stuff, but tell about the influences in your life that really got you here today.

Holly: My parents are great. I’m a family of artists, really. My two older sisters are wonderful artists, but my mom is a dreamer, and my dad is a realist, so both of them together make a very confusing combination sometimes because Mom’s like, “Follow your dreams,” and he’s like, “Not every dream,” and then she’s like, “You can do anything you want,” and he’s like, “Not everything.”

Chris: They sound like a good fit to me. They sound pretty good.

Holly: I kind of combined the two things. I’m like, “I’m gonna create something that’s never been done before.” That’s my mom talking. Then I’m like, “But I’m gonna make it where it’s gonna be a good business concept.”

Chris: You’re going to monetize it.

Holly: I’m going to monetize it. My dad’s like, “Yes.” My mom’s like, “Go for it.” I’m like, “Finally.”

Chris: Win.

Holly: They’ve been a great support through that because I’ve had a lot of people who, they ask me what I do. They run into me. They’re like, “So what do you do?” I was like, “Oh, I own a shoe shine business.” They’re like, “Huh, no, really, what do you do?” I was like, “No, I shine shoes.” It’s been fun because I still do graphic design on the side, and that helps offset some of the cost, but I’m pushing that creative side, doing graphic design and then getting out from outside of computer and talking to people, shining shoes.

To answer your question, though, they have been a really great help. Honestly, I’ve just been a sponge of information, and as anyone who is a new entrepreneur, it is both exhilarating and frightening at the same time because you’re jumping in and you’re like, “I’m self-employed, and the only person who is in charge of my financial future is myself.” It’s a great learning experience because you’re just meeting a lot of people and soaking in ideas and advice and taking everything with a grain of salt and realizing that some people have different business models, and someone who didn’t come from a business education background, getting thrown into the nonprofit world at a management level, you learn by fire, and you get thrown in, and Google’s been a lot of help, and a lot of self research and materials. That’s the most exciting thing. Shining shoes is fun, and it’s really great, but being able to build a business from scratch with a new idea and a new concept that hasn’t really been modernized in, gosh, shoe shining hasn’t been modernized in a couple hundred years.

It’s fun to challenge myself with balancing that, running a business, doing the administrative part, as well as the social networking.

Chris: You’re doing fundraising, raising donor support for the nonprofit you were working for?

Holly: When I was there, yes. I managed it. I was the Executive Director, so I was in charge of program development. I was in charge of … It was a small staff. We had just three people with about 200 volunteers operating on a quarter million dollar budget, and it was challenging. Basically, I wore a lot of hats. I would be balancing the books one day, and then cleaning the toilets the next day.

Chris: Wow.

Holly: Anyone who’s been in nonprofit knows that very well.

Chris: Then, right now, in the last … You started in 2017, which is about … Is that a year ago? Did you start early … Is it less than a year that you’ve been doing this?

Holly: Full-time?

Chris: Yeah.

Holly: Would be since last July.

Chris: What, about six, seven months?

Holly: Seven months, yeah.

Chris: What’s been the greatest challenge so far? What’s been the biggest …

Holly: I think the biggest challenge is fighting against my own mind because all-

Chris: What does that mean?

Holly: In about 25 seconds, I’ll go through about 75 different thoughts, and I’ll just be like, “This is really fun. I’m glad I did this,” and then I’ll see something, and I’ll be like, “Oh, well, the economy looks like it might dip here in the next six or seven years, and the first thing that people are going to cut out are luxury services, so why am I going into a luxury service if the economy’s gonna drop,” and then I start looking at jobs, I’m like, “Well, I don’t wanna sit in a cubicle for the rest of my life,” and then I’m like, “Oh, my gosh. What am I doing?”

Chris: Does this sound familiar, ladies and gentlemen?

Holly: Right, everyone?

Chris: Keep going.

Holly: You go through the daily existential crisis. I’m sure you do it every day for the rest of your life, but it’s-

Chris: It’s riding the waves—

Holly: It’s riding the waves of the emotional waves of … It’s more of that mental push of waking up every morning and like, “All right. You wanna make money today? You gotta do it.” You’re not going to rely on anybody else. You have to emotionally prepare to go out to yet another networking event. You’re like, “All right. What kind of weather am I gonna talk about today? Let’s get our small talk business-“

Chris: One more business card, baby.

Holly: Small talk index cards out and see what we can do. That’s one thing that’s been great about ACA, though, is the first moment I stepped in it, it wasn’t that. It was everyone was just really comfortable because everyone’s so sick of the small talk.

Chris: Sure, sure.

Holly: It’s real, and that’s the thing that I like is real networking and really getting to know people, but that’s been the biggest struggle is just getting up and having to choose to do it every day and growing it and riding those mental waves of saying, “All right. Well, it’s either this or you’re working for someone else.”

Chris: Give me liberty or give me death.

Holly: Or a 401K.

Chris: Or a 401K. That’s good. Then, how do you refocus? How do you come down from the wave? What are some things that you do? Do you exercise? Do you … some outlets? Do you have a support system you talk to?

Holly: Absolutely, yeah.

Chris: Tell us more about that? How does that work.

Holly: For sure. You have to have a support system. I’ve got a great partner here that helps me and my family, friends, but it’s having that creative outlet helps. I play music.

Chris: Oh, really? What do you play?

Holly: I do guitar, piano.

Chris: All right.

Holly: Used to play in a band. Everyone’s been in a band, right?

Chris: Yeah.

Holly: Just getting out there and just doing some creative … I play sports, anything, anything out there.

Chris: Wow.

Holly: I do … I still umpire, which is fun.

Chris: Do you really?

Holly: You take out a lot of nice-

Chris: Baseball or softball?

Holly: Both.

Chris: Wow.

Holly: You take out a lot of aggression behind the plate, in a healthy way.

Chris: A lot of people take out aggression on you, as well.

Holly: Exactly. I just feed it right back to them.

Chris: All right.

Holly: It’s fun. I played softball, and then now I umpire. My dad and I actually umpire together out in a league, and it’s pretty fun.

Chris: That’s amazing. So many directions to go in.

Holly: I’m a little all over the board here.

Chris: No, you’re not. Actually, it’s actually a lot of entrepreneurs I talk to are very … They are artists, as well. What I appreciate about what you’re sharing … Well, let’s talk more about the business side of it. Then, when you just decided to go out on a passionate whim, or did you have a little bit of a small plan? You do a business plan? Talk a little bit about that process. Maybe somebody watching this is maybe thinking about launching in there in maybe that same quasi-death spiral of a cubicle, and, right now, they could be inspired to hear something here.

Holly: Well, I’ve heard this from several other entrepreneurs, as well, is you can plan all you want, but you’re never going to have the perfect time to jump into something. I think I was waiting. I kept waiting to have everything lined up, all my ducks in a row, maybe getting funders or financiers and getting the money to start it, but no one ever has a perfect time. I had a small plan, and with the idea that it’s probably going to change. I just jumped in with the biggest success right now I have is the business package where I would just come directly into sales offices, law offices, car dealerships, and do drop-off and pick up shines there. That’s been really great because guys and gals can actually bring their shoes directly to work, not having to worry about making three other stops on the way. I meet them there. I get to know a lot of businesses. I started with that, and then did the individual, the scheduled monthly plan for people who wanted individual, so pick up from their homes, kind of like Hangers, the laundry service.

I started with those three things, and then as I got started, I realized that there was some other needs out there and moved with the flow on that one. A big one, especially trying to get my generation involved in the shoe shining world, is a little more difficult because they’re still in the … Most of them are still in the fashion sense of everything needs to look like it’s pre-worn. They’re like, “Oh, we don’t wanna shine these up. I just got them to the way I want ’em.” I actually shifted into repairing tennis shoes, like Adidas Sambas and Nike tennis shoes, because you spend quite a few dollars on those, so re-gluing soles and cleaning up the laces and just making them look like new again.

Chris: I’m curious. Apart from your services, and I’ll get into plugging your business model a little bit. You can share with us a little bit more about that. Where do people go to … Who are the shoe doctors? How does that work?

Holly: There are many actually really great shoe repair guys, and that’s why I don’t really do shoe repair, but a lot of them don’t like to touch tennis shoes, and that’s why I started it, mostly because they stink far worse than any of the other shoes.

Chris: We can’t have that.

Holly: I’ve invested in some car fresheners, but there’s a lot of good repair shops around, and I’ve partnered with a few of them, so I don’t have to recreate that wheel, and if everyone needs a shoe repair, I can either pass on the information or actually take them to the shop themselves. Then, as far as just shoe shine, you’ve got the place on the Plaza. In Kansas City, you’ve got airport. I know the guy who runs the shoe shine stand out there. It’s fun being in a weird niche shoe shine world. Everyone knows each other, but there’s not many actual just shoe shine shops around.

Chris: Talk a little bit about, you got a couple tiers, one, two, three. Basic package is what?

Holly: The basic package is an individual package that I come pick up from your home, up to five pairs a month. Right now, it’s 20 bucks a month, which is a killer deal, but it’s really just an introductory package of what I can do to your shoes and help clean up. It’s mainly for … I designed it for couples or roommates living together that may not have five pairs of their own shoes that need to be shined up every month, but, together, they can create a little package of each other’s shoes.

Then the premium package is up to eight pairs, and then you get the full treatment. You get the nice insole cleaning and it smells all lemony fresh when you get it back.

Chris: You get the special cream on that one.

Holly: You get the special cream, extra swag and street credits. That comes free.

Then, in the business package, like I said, is the most popular, and that is either individually paid or company paid, so an hourly rate of 45 an hour, and I can shine up to about 15 pairs an hour.

Chris: That’s a corporate package, going right into the big lobby of whatever?

Holly: Mm-hmm (affirmative).

Chris: Great. Getting to know you a little bit offline, as well, off camera, as far as your heart for nonprofits. Talk a little bit about that. You’ve actually been tying some missional stuff with your shoe shining. Is that part of your heart and your strategy to grow the business?

Holly: Yeah, exactly. As someone who has a background in nonprofit, my dad, actually, he’s a nonprofit now. Obviously, a lot of my influence comes from my family, which I’m very grateful for.

Chris: Sure.

Holly: It’s being in that world. You do get addicted to the fulfillment of just helping people, but in a nonprofit social service side, you also get burnt out really quickly on the red tape and the continual cycle of it. It is frustrating. During my time running the nonprofit, I realized that the biggest effect and the biggest positive help that we can have to our community is not necessarily with nonprofits, but it’s with the small and medium-sized businesses. Those are the ones who are pushing the economy. Those are the ones who are growing the job market. Those are the ones who are able to give families an income.

For nonprofits, it’s one time. It’s few and far between, but businesses actually feed the future of that, and that was something that I realized where I’m like, “Well, I would love to create a business where I can eventually hire people on who need a job, who may not have the education for a business corporate job and who doesn’t feel like they can get the training at the time.

Chris: Sure.

Holly: I’ve met a lot of people in my work at social service that have been unemployed or have never had a job, and they’re some of the wittiest, funniest people I’ve ever met because they make up for what they lack in education and job experience with their personality, and that’s what gets them through, and I am like, “Man, I would love to have these people shining shoes. They would be so great.” My goal of this business was to create something where it could easily be expandable and easily hire people on and, ultimately, just help grow the job market.

Chris: It was interesting. You almost had a little campaign developing right there. I saw your platform.

Holly: Sorry.

Chris: No, it was—

Holly: That’s the political science coming out.

Chris: No party affiliation. We’ll call it Independent Shoe Shine Party of America.

Holly: I run for the Independent …

Chris: Whatever you want to call it.

Holly: Independent Soles of America.

Chris: There you go. That works.

Holly: There it is. That was bad. Thank you. Thank you.

Chris: That was… That was good. That was good. You’re someone who wants to create jobs. You’re someone that … It’s the hard work of the individual, and if they don’t have, that there’s deficits or whatever, there’s ways to fill that gap and then giving them hope and giving them a place to find themselves, to make a little more money and to make a difference in people’s lives. It’s amazing.

Where are you seeing that headed? Where are you seeing that going? Are you getting some traction now? How can people locally here in Kansas City, how can they help connect some of those dots for you?

Holly: Well, I’m just growing business right now. I know it’s real in its premature state-

Chris: Sure.

Holly: But it’s been growing exponentially just this month.

Chris: Wow.

Holly: I have just signed on five new clients this week, and that was amazing, so the word of mouth has been spreading, and the goal is to just be able to have so many on board that I can’t do it all by myself, and then I will be able to put out an…

Chris: Sing in the staff meetings.

Holly: Exactly. That way, I can just outsource that to some employees, too, and then run the admin side and keep growing the business. In terms of … I think everyone’s been doing it here. Just word of mouth has been basically the reason that I’m growing.

Chris: You had an event just recently. What was that? It was during Christmastime.

Holly: Yeah. ACA and Carl Little from Datamax, they helped with a shoe drive we had.

Chris: What is that? Talk about that.

Holly: I can’t remember how it came up, but I had this idea of, okay, I want to give back, and I personally have two or three pairs of shoes in my closet that I just don’t want to give away, but I haven’t worn in five years, but I do know working on the social service side, I knew that finding professional shoes and clothes, that is very difficult for people who can’t go out and buy even an $80 pair of shoes, a $60 pair of shoes. Even at a thrift store, it’s hard to find a good pair of shoes to go to an interview, so we came up with this idea to do a drive for that, and we collected over 135 pairs of shoes, of seven huge trash bags full of shoes and clothes and were able to clean them up and donate them to a organization-

Chris: Wow.

Holly: That helped give people jobs. That was really fun. It was a fun time.

Chris: Wow.

Holly: Thank you, ACA, for that and anyone who was involved in the drive.

Chris: I’m almost thinking of sometimes there’s thrift stores and Salvation Army places and you see the whole racks of shoes and the shoes are just … Man, they are worn beyond recognition.

Holly: You can find a few gems out there, but you got to look. You got to shop. It’s a whole day’s worth of shopping.

Chris: Is that an ideal client for you, as far as going in there and saying, “Hey, Mr. Owner of Second Hand Thrift Store, we come in … A team of us come and shine these up,” and then proceeds and profits? Is that something?

Holly: That would be nice.

Chris: You can write me a little business strategy session.

Holly: I like it. I like it. Those 135 pairs of shoes take a long time to shine.

Chris: That’s true. That’s a lot of sweat equity right here.

Holly: I definitely got my exercise in that day.

Chris: All right.

Holly: I think just encouraging people to … Really, instead of giving them to a for-profit store, finding an agency that actually just gives them to the people they serve.

Chris: That’s great.

Holly: That was important for me, too, because it’s easy to donate them to the place around the corner that’s going to price them for nine bucks, and even nine bucks is a lot of money for somebody.

Chris: What has shining shoes taught you about business for life? What are some lessons you’ve come away with in the last … Well, you’ve done it years ago, but now coming back full circle. Now you’re in it.

Holly: Well, it’s funny. I definitely had more job offers shining shoes than I have actually putting out my resume.

Chris: Oh, really?

Holly: It’s been pretty funny.

Chris: That doesn’t surprise me.

Holly: They’re like, “Hey, you can sell. Come sell for me.”

Chris: Oh, wow.

Holly: I was like, “No, I’ll just shine your shoes.” Really, what it’s done is you can go to school and you can sit in the classroom all day, but just diving out there, and even if you don’t feel it, you got to feign a little confidence and it helps. It goes a long way in the business, but it’s really about partnerships and relationships, too. If you’re trying to do something by yourself, it’s never going to get off the ground, and that’s, I think, the biggest key, and what I’m so grateful for is all of the help and even the advice where someone hands me a business card or hands my business card to someone else, and they’re just like, “Hey, I don’t think this is a good strategy or I don’t think this is a good price point or maybe you should think about doing this.” That’s helped just develop my business, and I know I’m going to keep doing that. I’m grateful for those relationships.

Chris: Wow. That’s awesome. Holly, where do you go from here? What does the next five years look like for you? What’s a dream or a passion or a goal perhaps that you have?

Holly: Well, definitely want to grow it. I definitely want to be able to have at least two employees in the next three years and to the point where I can even step out and just do administrative and just seeing what doors open up with that and hoping that I can learn more about the nitty gritty of running a business. If it’s something that grows and takes off, that’s great, but I’ve always, like I said, I’m an optimistic realist, so I plan to fail, but I also plan to succeed, and so if it doesn’t work, then I’ll just move on to the next thing.

Chris: Wow. That’s amazing. As we’re starting to land the plane here, we’re going to have some people come up and ask you some questions in the next segment, but my last question to you is, what really keeps you going day by day? What is it that keeps you … I know we kind of covered that in the beginning, but if you were to give it a passion or a mission statement, why do you stay doing this, because that’s got to be an interesting grind day in and day out. That’s just so not a business that people are really too familiar, even … Mobile shoe shining, I think it’s very unique. I don’t know how many people are even doing it around the country.

Holly: I’m not sure. It’s more popular in Europe right now.

Chris: Is it really?

Holly: They’re always 15 years ahead of the time. I’m just getting on the forefront.

Chris: Maybe let me ask it this way. Let’s say someone’s watching this video right now, and they are in a job for a few years and are thinking about … It could be something as simple as shoe shining. That’s so cool. You can monetize just about any passion today in this economy. What would you say to them? What would you tell them? What advice would you have?

Holly: Wow.

Chris: That’s probably a good way to ask the question.

Holly: That’s interesting. As someone who hasn’t been doing this for too long, I don’t feel I have a lot of advice, but-

Chris: Actually, you kind of do. You bring a lot to the table. Go ahead.

Holly: I think at the end of the day, life is very short, and you have to do what you love to do, and if it’s something as simple as shining shoes, that’s no one else is doing, you need a shoe shiner around. If it’s something that you don’t like doing, what’s the purpose of doing it? I think we get so bogged down by the day to day of living, of making money to live, to make money to live, and if we’re not doing that for a greater purpose or even just the inner happiness, then I don’t think it’s worth doing. I love working for myself because I can be with my friends, I can be with my family. I can also meet so many people, and that’s what makes me happy is being able to give back and not be constrained by the grind.

That’s been really freeing in a lot of ways and frightening at the same time, but I think I’ve talked to even people who have been working the same job for 20 years and even encouraging them to, “If you don’t like what you’re doing, don’t do it. You’ve developed so many skills in what you’re doing now that you can find something that brings a little bit of joy at the end of the day.”

Chris: That’s awesome. How was this? Are we doing okay?

Holly: I think I’m okay.

Chris: Did we have fun?

Holly: I didn’t pass out, so I’m okay.

Chris: Do we now do the Jimmy Fallon guest … Do we bring a few more guests out?

Holly: Do we do the lip sync contest now? Is that what we do?

Chris: Yes, we can do lip sync. We can do karaoke in the car if you’d like. We can fire that off a little bit.

Holly: Do I get paid for this? Is that what-

Chris: No, you don’t get paid for it, but the royalties will just continue to come in. I can guarantee you-

Holly: No, thank you so much.

Chris: The social currency gain from such things. This is a real pleasure.

Holly: Thank you very much.

Chris: How can people get ahold of you here in Kansas City? What’s your website?

Holly: You can go to You can find me on Facebook or Instagram or good old fashioned phone call. I appreciate that, too. You can find all that information on my website.

Chris: Let’s hear it for Holly from KC Shoe Shine, ladies and gentlemen. All right. Thank you.


Executive Summit: Reg Pincombe ACA President