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Hi and welcome to the special podcast series in partnership with Chase for Business. I'm your host, Ben Baer with Ink Custom Studio. In this episode of Chase's make youe Move Summit, I sit down with Chicago based entrepreneur Chris Clark, founder and CEO of Toss and Spin, a racket sports business that has a mission to bring the joy of racket sports to every hand everywhere. And we'll be joined by Chase's Alejandro Fajardo, a senior business consultant, as we talk about how to turn a passion into into a profitable business and how to manage some common financial hurdles as you scale your success. Chris and Alejandro, welcome to the podcast. Chris, I'm going to have you share a little bit more with our audience about what Toss and Spin is and what inspired you to start it.
B
Yeah. So furloughed during the pandemic, I was sitting on the side of the tennis court and I was like, how can I create something that is real within the racket sports space? How can we connect the world through racket sports? How can we put as many paddles and rackets into as many people's hands as possible? So we set out to create the most fun entry point to racket sp worldwide. We're not there yet, but that's what we're trying to do. In its simplest form, we do tennis, pickleball and padel lessons, classes and events. We have eight partner facilities or 10 partner facilities in Chicago, right in the city. Two indoor, eight outdoor. We have a great partnership with the park district. We also have a mobile pickleball events business. We call it Courts and Creation. So we bring the courts anywhere and curate the experience. And that has happened in over 40 cities around the country.
A
What was the hole in the marketplace that existed in your mind when you were sitting there on that court trying to think through, I need to do something in this space. What was the hole that existed?
B
Well, indoor sports and gyms virtually shut down. So everybody, and if you recall, it was around the summertime, so everybody, especially in Chicago, was just outside looking for things to do. So we kind of fell into this marketplace where like, hey, we can create fun through tennis and pickleball and we can make a really big business out of it. And it just kind of, I call it like a basketball layup. It kind of laid up for us and it ended up being a really good thing for us to evolve into.
A
And so from those early starts, you said now you expanded into multiple sports. You're in multiple places around the country. What's been sort of the key driver of the growth, would you say chase.
B
For business, what's really helped is like thinking through what resources are needed. And I always say, like, don't go too fast, right? Because if you bite off more than you can chew, you'll end up on the sideline. And I mean, if you think about entrepreneurship and the facts around it, they're not that great, right? Like a lot of businesses fail and even the businesses that are somewhat succeeding that the owner is not making buus of money, right? So you do have to go through some tough times to really see success. And I've been there. I'm sure there's even more tough times ahead. But you know, we take it one day at a time. If you ask me how I'm doing, I'm taking one day at a time. But I'm always smiling because it's a gift of like you said earlier, it's a gift to be able to wake up and work on your own business and try to build something that is meaningful for the community.
A
Alejandra, let me bring you into this conversation about what are some of the common sort of financial hurdles that small businesses like Chris face, especially when you're sort of just trying to get off the ground. What are some of the key things that you sort of guide them on and help them to as they start to grow, but also to scale once they're successful?
C
Sometimes business owners don't get prepared, as Chris was saying they want to do. They so excited about the program, their business, they're so excited about their idea and they're like, okay, let me just do it. I have this amazing idea. But they don't take the time to really write a business plan, you know, review information about the industry, how the industry is doing, how it's doing last year or the past five years, how is it right now? What are the tendencies for the following years? That's something that is very important for business owners to take in count. They have to work on projections. If there is a business that has been in business for two years, three years, and let's review how you're doing financially and how the industry is doing. And let's see if you're doing, if you're at the same level of the industry and if you're not, there is a great opportunity for you to keep growing. But just thinking that they can do business as as it comes, it doesn't work that way. They have to be prepared. They have to. They don't need to be financially experts, but they need to have a good conversations with their business accountants. Right. They need to have an accountant. What I find out is a lot of business owners, they're doing their accounting and when there is a time to like talking back. Right. During the pandemic, a lot of business owners were not able to get help from the private sector or the public sector because they didn't have an accountant. They were not able to get, you know, like the profit and loss statements that the government was asking or the the private sector was asking. So having a great conversation and having with their accountants, knowing what their accountants are doing, they, as I mentioned, they don't need to be experts, but they need to know financials. Because if we cannot walk covering our eyes, you have to be no expert in everything, but you must know, you know, several areas of your business.
A
Yeah, that, that concept of know your numbers comes a lot both at Inc. But also I know, for Chase for Business. Chris, tell us a little bit about your sort of journey as you were sort of starting and scaling the business, about how you sort of learned and, you know, understood a little bit more about the numbers to help you grow. What advice can you give?
B
Yeah, so I spent nine years in corporate and to be honest, like, finance wasn't what I was good at. I was good at the marketing and sales and smiling at people like, I'm smiling at you now. So I had to learn the financial aspects. And I always tell people, like, doesn't matter how much revenue you're driving, if your cash flow is not good, you're going to be in, you're going to be in trouble. And I think two and a half years ago we signed a contract with a large client. And I still remember to the day you started learning about net 60s and net 90s. And like, well, I'm net 15. They're like, well, we'll find someone else to do a job. But our company is net 60. So you end up having to front a lot of cash and you can end up in not a good position. So I think it's like, how do you plan for those things? And also working with Chase was able to get some additional funding to support the business that we could show that was coming in so we could fulfill that big contract that we had. And learning those things propelled us to continue to move forward as we think about the day. But hey, we had a break downstairs and I'm downstairs looking at, okay, what do our numbers look like the back half of the year? Do I see any problems? I think the one thing too I would recommend is always looking ahead because, you know, we're. We're here today, but what's happening in December and are you going to have issues? What's happening in January? Where is it going to slow and what changes can you make to offset that in your business? And although it's easier said than done, I know kind of know what I should do. But just because I know what I should do doesn't mean it's going to get done. It's not easy to do. So I think that's the one thing is just again, taking it that day by day and building brick by brick.
A
Growth is a great thing to have, but also comes with its own set of challenges. So how have you managed the growth so that you're growing smartly without being overextended, let's say, or getting too far ahead of maybe where the sales are? How are you managing that right now?
B
Yeah, so I live in our P and L. That's one thing. Like year one, year two, I just saw a lot of revenue, like, oh, this is so cool. And I didn't realize, like, hey, revenue's coming in just to pay it out. Now, again, I live in the P and L. I live in our system. I'm not doing the accounting because that's not my expertise. And one of the things, I like to sell, I like to network, I like to meet new people, and I have a vision for our business. And I'm almost there to where I'm spending the majority of the time thinking about that. Like, like I said yesterday, right now we're sitting here talking, but we're running classes all over the city. We have events going on all over the city. And I'm here with you. It wasn't like that two years ago I would have to cancel class or do something like that. Right. So. But again, just making sure we're not biting off more than we can chew and kind of instilling in our team to think ahead. Right. Like, what problems are we going to see? Because to your point, like, bigger isn't necessarily better, speed is good, but you can end up on the sideline. And so you just got to be really, really careful. And I think as we look at social media today, you see people who appear to be doing very well. But as an entrepreneur, I know, like, it is tough.
A
Tough.
B
It's tough out there. It's tough for me, it's tough for everybody else. But those tough times make us that much better. And I look forward to embracing the tough times that are ahead of us.
A
Yeah, I mean, we're a publication, we have, you know, historically we have business covers. It always seems that it's this easy journey from, you know, from starting to success. But it's a journey and no, it comes with a lot of challenges to overcome and grit and resiliency that come out of it. Alejandro, sort of that question about how do you try to manage growth smartly without being overextended? What are some of the things you do? What are some of the advice you give to the businesses you coach as part of the program that you manage at Chase?
C
Again, I always tell them, you must be prepared, you must be wise. Don't be afraid to ask questions. Don't be afraid to fail. Sometimes it's like, I don't want to lose money. I don't want to, and it's okay. But what is important is you need to be prepared. There is a lot of information. There is a lot of organizations out there, like in the Coaching for Impact program at Chase for Business, what we do is we do our job, but we also connect with business community organizations and just, you know, they also, they're also giving a lot of information to business owners, and most of them are free. But sometimes business owners are so busy and they don't take the time to invest in their business. And I'm not talking about money. It's just time, you know, getting prepared, writing a business plan. I always say that a business plan is a life, a live document, because it's changing all the time, right? Like you write a business plan. But as you mentioned, Chris, next year is going to be different. So that business plan must change if you want your business to keep growing.
A
And you also come in from a perspective that you were an entrepreneur and business owner yourself before you joined Chase. And then your current role, does that help inform sort of the advice that you give to the entrepreneurs that you're working with?
C
Yes, it helped me a lot. I learned a lot. I have a lot of contacts within the community. And I always say, I know the pains, I know how it hurts, but I also know how to solve it, right? And sometimes I have business clients that are so scared about taking. Like, for example, I have this client, he's growing so much, and he was like, I'm afraid to get into a loan or a business line of credit it. And because when you're not prepared, you're afraid. But when you prepare, you have your business plan. You know how you plan to pay back, you know how much money you need, why you need that money. Do you really need money, right? And when you get prepared and, you know, you're not afraid and as it's just, you know, having the resources there for you and don't be afraid to ask, like having a good relationship with your banker. You know, during the pandemic, a lot of business owners didn't have a banker, and it was terrible for them. You know, it's important to have your banker. Maybe two bankers used to have, you know, maybe the banker and the branch manager, and you start that conversation with them and also, you know, like, just trying to see what other resources are for you out there.
A
Yeah, Chris, I mean, as you were building up Toss and spinning beyond Chase, what were some of the other mentors or partners or people that helped guide you and help you along the way as you were building the business and before, you had a full, like, you know, maybe team to sort of help support you so you could be at things like today without having to cancel things.
B
Yeah. So, you know, my parents had long corporate careers, so one of the things that still sticks with me is my mom saying, you know, don't scale too quickly. Like, you want to scale. You want to growth, but make sure the growth is right for you. And it's hard to. We live in a world where you just want to grow. Like, that's what you think you should do. But you got to be in a position to handle that growth, because if you're not and you don't have that support, it's going to be tough. I also have a business coach, and I think having someone just to bounce ideas off of or even just like, I need a shoulder to lean on or a couple tears need to come down the face, because that. Or down my face, because that's what entrepreneurship is like. You have that person to really. To really strategize who isn't inside of your business per se, but is like maybe 30,000ft looking in. And that's been. That's been really good. Good for me as well. And then also just I have a lot of trust in the people who work for Toss and Spin. I mean, you have to. If you have pros running classes and events, you know, around the country and ops teams working on the back end, so just really making sure their voices are heard on how we can grow. And for me, laying out where we want to go from a company perspective and make sure we're living by that. The most fun entry point to racket sports, like, how can we continue to build towards that? And like I said before we started, if we're not Having fun. What are we, what are we doing? And I get to choose. Like, hey, this partner is giving us money, but this may not be the right partnership. And I got into toss and spin to be able to pick who we work with and be selective and have fun. And as soon as I stop doing that, that's when I know I'm in trouble. So we got to keep the fun in it.
A
What sort of advice would you give to other entrepreneurs that are or aspiring entrepreneurs and say, you know what? I really want to work in this sport that I love. I want to build a business out of it. What have you learned from your journey as an entrepreneur and working in sort of the sport that you were passionate about?
B
Yeah. So build a business plan. And although it's going to change like every quarter, I refine my business plan and it's definitely not the same. But just having that guidance gives us something to be accountable towards and then ask for help. I was amazed. Like, I didn't ask for much help the first couple of years and you think you know everything and then you're like, oh, my gosh, I can't believe we're operating a business like back that that way. But ask for help. There's tons of resources out there that can get you to that next level. So, like, even today, meeting new people, what do you do? Oh, great, like, I have something for you or hey, I would love to pick your brain on this. Like, we want to collaborate, we want to help. And those, in my opinion, the biggest deals we've done are from relationships. It isn't from me. I wish it was from me. Cold calling day, but it's not. It's from me meeting new people and saying, hey, I have a solution that might be able to help you. Or, hey, your company's looking for an event. We have a great solution that we can bring to you that is off site, that type of thing.
A
Alejandro, when you're advising business to sort of again, look for partnerships, look for mentors, look for help in the space as they're growing. What are some of the key things that you tell them to look for in whether it's a coach at Chase for business or out in their sort of business area as they're sort of growing their business and they're right now they're a solopreneur entrepreneur. They don't have that management team yet.
C
Yeah, I always talk to them about. We talk about how they started. Right. And why and then analyze where they are right now and where they see themselves in five Years. And we work on that, right? Sometimes there are some business owners that don't know that they can get certified as a minority business enterprise, as a woman business enterprise, or other type of certifications. So it's just be open to get information and be open to change, right? Be open to say, okay, let me just try this, and getting certified, for example, when you get the certification, you open doors to do business with the public sector, with the private sector. But sometimes there are some business owners that don't want to grow fast and they're like, you know what? I'm not doing that. And it's okay too. It really depends on what they want to do, how they see themselves in five years. But it's important to be open, right? Because sometimes there are some opportunities right there in front of them. And if they're not ready, if they don't prepare, or if they're afraid they're not like someone else is going to take that opportunity. So it's really just talking to the business owner, be very clear on what they want to do and the capabilities. Because sometimes there is one example of the workshops that we do that is an IT company is doing amazing. The owner is hiring people, buying more equipment, computers and everything. But you know, they're. They get the money when they close the deal. And it's like they're working, working, working. Then they. The business owner is spending a lot of money, but is spending the money before they receive the money. So in this case, you have to be very strategic with your cash flow, right? Be strategic with your cash flow. Make sure that you get the money first before you take it out. And thinking if it makes sense to have a business line of credit, for example, and say, okay, just to avoid being on low capital, let me just have a business line of credit. So that will help me to continue to grow. And like, I have another client that she's growing very much and she needs to hire someone. So we were able to lend her money and she hired someone. She's in Germany right now, you know, and it's amazing because she knows the need to be here. The business is, as you mentioned, you're here and your business is working. Right? And that, that's the goal, that you don't need to be there 24 7. You can take some vacation if you want, but your business is going to be producing. But again, you have to prepare. You have to know where you are right now. Recognize if you need to write a business plan or if you need some access to capital. It's Important to be open to that.
A
Yeah. And asking the questions, asking for help, as you talked about, is to sort of like to know what's actually out there because sometimes there's things out there that you aren't aware of. We hear this all the time. That grants partnerships, programs that can support you, whether it's government, private sector that can actually help benefit your business and that don't come necessarily with as many strings attached sometimes as other sources of partnerships are. Chris, talk us through your growth goals. Obviously a big, you know, you've had a strong track record of success so far, but imagine you're trying to take things even a little bit further. So what's the, what's the smart growth future for you for the next couple years? That is on your current business plan?
B
Yeah. So we're going to look at a couple different things. One, putting more boots on the ground in key markets that resemble Chicago. I think we're successful in Chicago because of the density. We can be in a neighborhood with a few courts and target those people within a 1 mile radius. Another big challenge we've had is wintertime programming in Chicago. Space is limited. So we have some new exciting indoor opportunities. With a partner of ours, very good partner, SPF here in Chicago, they created the first indoor pickleball facility. We're partnering, partnering together to launch a new indoor venue that will house both tennis pickleball and be more of a multi sports complex. So that will take away the seasonality in our business. I'm proceeding with caution though, because I saw the cleaning bill the other day and I'm like, we've never had a cleaning bill, so there's some learning curves there and different things.
A
Wait, wait, so cleaning bill for what? In what way?
B
Well, you have to keep the facility clean.
A
Okay. So just general cleaning, like cleaning up after things. Not just, okay, not that like, like.
B
I think I could do it, but like that also as an entrepreneur, things you don't think about. Yeah, you don't think about them. But while you can do them, should you do them, is your time value to other places. But those are the two biggest things we're working on. We have some really good partnerships with some large companies like aarp. We do a national pickleball tour for them. So just really focusing on the P and L and then and really getting lean in terms of things that don't make sense so we can continue to drive profit which will help our growth.
A
Yeah. All right, so I'm going to put you the hardest question for the end. So tennis and pickleball. Some communities get divided by them. You sort of unified them along with paddle. So what's your advice for those communities out there that are struggling with whether it's tennis or pickleball? Is it just both? And learn to work together? What's your advice?
B
I think you said it great. I think it's learn to work together because now they're building equipment that is silen. So for the HOAs that don't want to hear the ping, ping, ping, you can have quiet paddles, quiet balls. So it's definitely possible for them to coexist. I play both. I actually play all three, and I love all three at the right occasion. Right. So I love pickleball because it's the master connector. It's something like, I don't know, anybody's racket sports ability at the table. But we can all play pickleball. Now, tennis, it's going to vary. Pick, padel or paddle is going to be somewhere in the middle, but it's still going to be hard. Very fun, kind of upscale. So I think there's a place for them all, and I think they should coexist because they are doing things, connecting people, allowing you to meet new people and have fun.
A
All right, well, very diplomatic answer. You handled that well. Is the hardest question at the very end. Chris, Alejandro, thanks again for joining the podcast and sharing your insights with us. We appreciate it.
B
Thank you for having us.
C
Thank you.
A
That's all for this special episode. I'm your host, Ben Baer, with Ink Custom Studio. Thanks again for joining us.
Podcast: From the Ground Up
Episode: From Pandemic Pivot to National Expansion: How Toss & Spin Is Making Racket Sports More Accessible
Host: Ben Baer (Inc. Magazine)
Guests: Chris Clark (Founder & CEO, Toss & Spin), Alejandro Fajardo (Senior Business Consultant, Chase)
Date: November 17, 2025
This episode centers on the entrepreneurial journey of Chris Clark, founder of Toss & Spin—a company born during the pandemic with a mission to make racket sports (tennis, pickleball, and padel) accessible and fun for all. Joined by senior business consultant Alejandro Fajardo of Chase, the discussion dives into scaling a passion-driven business, overcoming financial hurdles, and the practical realities of growth. The focus is on resilience, building community, learning financial discipline, and leveraging partnerships for sustainable expansion.
On Entrepreneurship’s Realities:
"If you bite off more than you can chew, you'll end up on the sideline."
— Chris Clark [02:15]
On Grit:
“It's tough out there. It's tough for me, it's tough for everybody else. But those tough times make us that much better.”
— Chris Clark [08:52]
On Relationships:
"The biggest deals we've done are from relationships...it isn't from me cold calling."
— Chris Clark [15:12]
This episode offers an honest and motivating look at the realities behind entrepreneurial success, highlighting that success comes brick by brick, with both passion and meticulous planning.