Nichole Montoya: Collecting Online Payments Made Simple with Cheddar Up

Nichole Montoya is the woman behind an intuitively designed platform that makes collecting payments easy as pie. With a mission to make it easier for parents, schools and clubs to track payments from their groups or communities, the Cheddar Up platform facilitates this process by providing a simple interface for collecting online payments.

Before founding Cheddar Up, Nichole worked with companies as a marketing strategist to help them grow and reinvent their brands. Her experience also includes co-founding and operating a high-end children’s apparel company where she handled design and manufacturing and expanded distribution to 80 stores across the country.

Nichole has always been a go-getter and a problem solver. In our conversation, she talked about how she built Cheddar Up, her co-founder relationship, as well as her exit plan for her business.

Creating a FinTech or SaaS company

Cheddar Up is a simple, easy-to-use platform that makes collecting online payments accessible for anyone. You can’t go wrong with its features such as the robust online payer tracking, automatic reminders, no fees for the collector, custom form fields, and the ability for people to pay in as few clicks as possible. You can also set up custom payment pages for almost anything in no time at all.

“There’s all these sort of nuances in how we’ve built features that make it really simple and appropriate for groups,” Nichole said. Did I mention that Cheddar Up also allows you to pay without downloading an app on your device?

As a non-technical tech founder, Nichole shared how she built Cheddar Up and the steps she took in creating the platform.

“I think finding technical talent is probably something that every founder struggles with,” she revealed. Achieving a strong engineering team can be challenging for any startup because it takes time, effort, and financial resources. That’s why it’s important to have a clear idea about what kind you’re looking for and how you want your vision to come to life. Nichole also considers the importance of having a technical advisor. That person could help you narrow down your search or give some advice in looking for the perfect candidate.

Ultimately, the “aha!” moment came when she realized that there was a lack of this type of payment platform. There were many steps forward in figuring out what their end goal should look like, but they all began with simply asking themselves what they wanted. “We got really clear on ‘What problem are we solving? What does that look like?’ We knew we had to build something to get in people’s hands to see if we were onto something.”

Working with a co-founder

Much has been written on how to find a great co-founder. But what’s rarely covered as equally important is managing the relationship over time. It’s easy to get caught up in the excitement of starting a business with someone, but the key is finding common ground as you navigate the process of building and growing a business together.

Nichole started Cheddar Up in 2012 with co-founder Molly DiCarlo. “If you’re not a technical person, it’s really great to have a co-founder. No matter what, whether they’re technical or not.”

Having a co-founder means that the responsibility of running your company is not all on one person’s shoulders. This can be both relieving and empowering for those who find themselves with an entrepreneurial spirit inside them. “I would not be here where I am today without my co-founder because she keeps me sane and brings so much challenge to the table,” Nichole said. It’s crucial to have strong collaborative communication and trust if you want your startup venture to be successful.

Exit plan?

Entrepreneurs often start out with the goal of selling their business eventually. It can seem daunting, especially after all the time and effort you’ve put into building up your company. But even if it’s not your dream, don’t rule this possibility out. How do you know if selling is something that will happen or not? The answer lies in preparing for an exit strategy from day one.

I asked Nichole if she is building her business with the goal of selling it or leaving a legacy brand that will be handed down.

“If I’m really honest, I want to build this really great thing and solve this really great problem and sell it to someone and make it all worth it,” she stated. “I don’t think I’ll do this forever, but I want to get it to a point where it’s a household name and everyone knows Cheddar Up as a group thing.”

The emotional toll that comes with selling your business can be one of the more overlooked aspects. It’s not unusual for people who own businesses to feel attached because they have dedicated themselves fully to this endeavor.

“It is 100% probably to a fault/part of my identity. Like I am the Cheddar Up lady. It is my third child. I love it so much. And I spend so much time on it,” Nichole admitted.

Still, building your business as if you are going to sell it someday is an excellent way of running a successful company. This mindset will help you prepare for any potential future endeavors, no matter what they may be or how far off these days seem.

Catch my full conversation with Nichole on the Fascinating Entrepreneurs podcast!

Transcript from Podcast

[00:00:00] Nichole: And it is 100% probably to a fault part of my identity. Like I am the Cheddar Up lady. It is my third child. I love it so much. And I spend so much time on it. But no, we’re going to get it to work and go, and then we’re going to let it spread its wings.

[00:00:16] Natasha: Welcome to FASCINATING ENTREPRENEURS. How do people end up becoming an entrepreneur?

How do they scale and grow their businesses? How do they plan for profit? Are they in it for life? Are they building to exit? These and a myriad of other topics will be discussed to pull back the veil on the wizardry of successful and FASCINATING ENTREPRENEURS.

I’ve written a book, a memoir that starts with my challenging upbringing with all the twists and turns and inflection points, including saving my company due to the pandemic. It will be published this year. So please go to and sign up on my mailing list so you’re the first to know when it’s available.

In this episode, we talked to Nichole Montoya who has created a tool for associations and group organizers to collect payment and information seamlessly on a digital platform. This is saving PTAs, girl scout groups and HOAs a lot of headaches and confusion when it comes to payments. Now let’s get right into it.

[00:01:29] Nichole: Even in college, I’ve been an idea person. So it’s not like it was surprising when I wanted to solve the problem that my company solves, which is Cheddar Up. And that wasn’t a surprise to me, but it was a surprise just how intensely I felt like I needed to solve the problem that my company solves.

It was just like, I can’t keep doing what I’m doing. Like this problem must be solved. And I went to college and started in management consulting. And so I had at least 10 years of experience doing things in business, helping other businesses. But I hadn’t really built my own business, but I love creating things and solving problems.

So I’m sure that’s probably a very common theme amongst entrepreneurs. And this is just a problem. So I was working for management consulting for the first big chunk of my pre-Cheddar Up career, and then went out on my own to work for a financial technology firm. And so my brain was on FinTech. 

At the same time, I had two little kids who were doing their thing in school, and I was trying to manage it all, like all working moms. So, I was doing my work-side, and then there was this issue that came up on my personal side, which sorta related to my kids. I was just filling out a lot of paper forms and writing a lot of checks and driving them across town.

And I thought that was super silly. So I was making that mental note of “This is ridiculous. Why hasn’t someone figured this out?” And then I had my aha moment, I’ll say, when I was talking to a girlfriend on the phone and we were like, “Oh, what should we do for the teacher? It’s end of May. We got to get her something.” And we were just going to do something the two of us, and for a split second I was like oh, in my head, I didn’t even verbalize it. I was like, “Should we ask these other people?” And then I immediately shut it down. Cause I was like, that sounds pain, collecting that money and are they going to pay me on the bang down, but they’re not going to pay me and tracking it.

All those things spun through my head. And then when I got off the phone with her, I was like, it’s just such a common problem. And so it was sorta like the chaos of all the paper I’d been filling out lately, and that little aha moment. I was like, “Gosh, why isn’t there this really friendly, easy to use tool sorta like e-bike, but that’s really payment forward?”

And then I was just like, “That needs to be solved.” Like it does not exist. There were some funny little companies that were trying to solve the “hey we’re all going on a bachelor party, let’s chip in” kind of issue. But that wasn’t what I was trying to solve. It wasn’t that simple. It was like, how do I get rid of the paper form and the payment piece, and smash it into one super simple flexible platform. Anyway, so that was the aha moment. And a million things happened after that that wasn’t quite as simple or straightforward as I was anticipating.

[00:04:12] Natasha: Yeah. And before that you had a children’s clothing company, correct?

[00:04:16] Nichole: I did. Yeah, I did.

[00:04:17] Natasha: Was that your first entrepreneurial endeavor?

[00:04:21] Nichole: It was. It’s funny how you go or I went through these life experiences, right? I was working downtown in Chicago, just out of college, working for a big company thing. That was an experience. I didn’t have any epiphanies. I was so I didn’t know up from down then.

So I was just learning, learning, and then transition to that early motherhood. When you’re just confronted with all these other problems. I think I knew at that time and saw so many really cool kid-related entrepreneurs at that time, because all these humans were in this new phase of life and confronting all these problems and me being one of them.

And that was with my sister that was like, just dipping my toe into what is it like to want to create something, create a brand. And try to go mass-produce market and sell. And that was a sort of a sensory focused kind of cheeky if that’s even a word, baby blanket, accessory company. And it was really fun.

It was fun ’cause I got to do it with my sister, but it was fun ’cause I was doing consulting part-time and that was a creative outlet for me. And then 2008, the economy fell out and I was like “Okay, cool. High-end baby is not a thing. People are just trying to pay their bills.” So we shut that down and then I started to consult more, but yeah, there was a big gap in between there, but that was definitely a learning experience and it was really hard.

We were basically doing retail then. I noticed I didn’t go back to retail when I started Cheddar Up. 

[00:05:50] Natasha: So with Cheddar Up, and I love the name, I don’t know if everyone will draw the parallel, but like young young people probably wouldn’t necessarily get it.

What do you think?

[00:06:01] Nichole: The name? Cheddar Up?

Yeah. It’s funny. We get the question all the time. Why Cheddar Up? And I don’t know. I actually think maybe younger people get it more so because I’m super not hip or cool at all. There’s a funny story behind the name that my co-founder and I were like. “I have this idea. We’re going to solve it, but we need a name.”

And my co-founder is the creative brains behind the brand. And so she needed something to like brand and we had all these funny names and my husband who’s a little bit older than me is the one who thought of it when he said it. I was like, “I have no idea what you’re talking about.”

[00:06:33] Natasha: He must be around 50, right?

[00:06:36] Nichole: He’s actually even older than that.

[00:06:38] Natasha: Because I remember when I was growing up in Des Moines, Iowa, my grandmother’s boyfriend at the time would refer to money as cabbage and cheddar’s sort of the same thing.

[00:06:48] Nichole: Yeah, there are so many funny slang words for money when you actually go study it, which is what we were doing at the time.

But at that time, when he said Cheddar Up, I thought he was crazy. And he’s “No. It means money. Let’s ask Ruben,” who was our nephew who lived downtown Denver. And he’s really cool and hip. And we got him on the phone and he’s ” Hey Ruben, if I say cheddar, what do you think of?”

And the first word out of his mouth was ‘money.’ It wasn’t like, “Do you mean sharp or mild?” It was like money and I was blown away and we, Molly and I, liked it because this is fun and playful. It’s taking this awkward task of collecting payments and information from lots of people and spinning it on its head and making it fun and playful as opposed to annoying and arduous.

[00:07:32] Natasha: So you talked a little bit about why you started Cheddar Up, which is great. And in that conversation we had just a little bit ago, you talked about some things that I’m assuming are the differentiator between your product and a competitor’s.

What is the number one biggest differentiator between you and your biggest competitor right now?

[00:07:55] Nichole: I would say by far the biggest differentiator is that we are really focused on solving collecting-from-groups. If you need to pay your girlfriends for that glass of wine, when you forgot your wallet or pay your dog-sitter or the tutor or whomever, like a Venmo or Zelle is really good, right? That’s one-to-one. It’s peer to peer money from point A to point B. 

And what we do, and we’ve really remained committed to, if you’ve got 8, 10, 20, a hundred, a thousand whole community of people who you need to collect payments from. And to take it a step further, if you need to collect payments and information, which is usually the case, when you’re dealing with a group, then Cheddar Up is such a slam dunk because we find it’s not usually when you’re just like, “Here’s 10 bucks.”

It’s usually like, “Here’s 10 bucks and my child’s name is Sally and her t-shirt size is small and she has an allergy and you need to sign the waiver or what have you,” or recurring payments. And so our challenge is really honed in on groups and study: what does a group need to cut payments and information?

One, we figured out real quickly it was information, but we really just honed in on what are those features? And we know that people need to pay without downloading an app. For example, right, if I’m going to send something out to collect from 200 people, expecting them all to have the Venmo app, maybe they do, but that’s not very realistic.

And it’s a pretty big friction point. So there’s all these nuances in how we’ve built features that make it really simple and appropriate for groups. We’ve also made it super flexible not to dig into the product, but like all these things, like it’s funny. I love to look every day and see all the different thousands of ways people have popped on and are using the platform.

And it’s just so varied. Someone might be using it for school tuition. Someone else might be using it to sell direct sales samples. Like it’s a crackup, but that’s a testament to our constant focus to keep it easy and keep it flexible.

[00:09:55] Natasha: Yeah. So you are back into the FinTech world and I’m assuming this is a SaaS company.

Let’s see business to business, business to consumer as well.

[00:10:04] Nichole: That’s such a great question. We are SaaS, but we also make money on payments. So we have a classic freemium model, right? You can stay on our free plan forever and we still will make money on the free folks cause we are a payment company and that’s great.

And then we are SaaS in that you can sign up if you need extra features that are in a paid plan, you can jump into one of those, but actually we’re a little bit more B2C than anything. And sometimes we’re B2B2C. It turns out that is a thing. Like we have a lot of partners, like actually you’re in San Francisco.

One of our big partners is the Girl Scouts of Northern California. And we partnered with girl scout councils all over the country. And that’s a B2B and then they push it down to their C. See right there, see as the troop leader. And so that’s one of our channels, but every day, lots and lots of consumers, organizers of the world just find our platform and they’re off to the.

[00:10:59] Natasha: It sounds great. You have exactly the niche down of your audience. So sales should be really streamlined. I would say you’re not going to go beating down the doors as someone that wouldn’t use it. So at this point, I would love for you to talk to the listeners about how you build a FinTech or SaaS company.

The platform. How do you find the developers? Can you walk us through that a bit? So if someone’s listening, they have this great idea. It involves creating a platform. What are the steps you take?

[00:11:33] Nichole: This is going to be tricky. I might flounder a little bit because I floundered a bit when I actually did it.

So I’m a non-technical tech founder, so that never is the best. I think it might be a little bit easier if you are technical, but it’s certainly doable. Our process was definitely not direct, but we got really clear on the problem that we were solving when we had to raise capital. And so that whole capital raising helps you get clear. The investors make sure that you are clear and they will give you any money, but we certainly didn’t go in and find money right away. We got really clear on what problem are we solving? What does that look like? We knew we had to build something to get in people’s hands to see if we were onto something.

And that’s what we did: spend a lot of my own money, just on a prayer, really feeling like it was going to be worth it. What are you spending money on? Engineers is what we were spending money on. And so finding engineers, I think finding technical talent is probably something that every founder struggles with. Maybe every company, maybe every big established company.

[00:12:38] Natasha: To just source and qualify them where you start. Yeah.

[00:12:41] Nichole: I think having an advisor who is technical is a really good idea. I didn’t have that right away, but I very quickly did after I made a couple mistakes. Someone that you can lean on, who can help you interview these folks.

You’re not going to know who you’re even looking for until you have some insights or plans in terms of what are you building it in? What language? What does it look like? Is it mobile? Is it web? Is it both? They’ll have different people. I’m a bit scrappy. And I think a little scrap is helpful when you’re starting with no funding and trying to figure something out that maybe you don’t know how to do.

And so I was looking at all the good dev shops at that time, it was Pivotal Labs. They were like everywhere. And they had a big presence in Denver. And I was like, okay, who works for Pivotal Labs? They’ve already vetted that engineer. And now I’m going to go knock on their door on LinkedIn and see if they want to do like some moonlighting for this really cool startup.

And that worked for me. Yeah, that worked for me.

[00:13:39] Natasha: And where were you having these conversations, were you being guided by an advisor? Did your co-founder help? Who had that technical jargon to convey what you needed to do?

[00:13:51] Nichole: It was very very initially, I did not bring on an advisor. I was like, I need an engineer and that didn’t work out.

That was like, maybe I’m going to hire anyone. That was like for 10 minutes and realized that wasn’t gonna work. Then I went this LinkedIn sort of route. And then I had an advisor who was like, once I sort of had or thought I had someone maybe interested. They helped me interview them for their technical skills.

[00:14:15] Natasha: So if you were doing it right now or you were telling someone how to do it, what advice would you give them? Where would you say that you should start?

[00:14:24] Nichole: If you’re not a technical person, it’s really great to have a co-founder. No matter what, whether they’re technical or not. I would not be here where I am today without my co-founder, because she keeps me sane and brings so much challenge to the table.

I think it’s really hard to start a company alone, you just need a sounding board.

[00:14:42] Natasha: So people think it’s really hard to be in a partnership. I can’t tell you how many people have really had challenges with that. So how long have you guys been in business together?

[00:14:54] Nichole: Since the beginning and Cheddar Up has been around for about six or seven years.

And we were friends before that, and that is a luck of the draw kind of thing. I know I intentionally pulled myself out of startup ecosystem a number of years ago. Cause it was just too much. But I remember when I was in it and we did accelerators and whatnot, and I spent a lot of time in San Francisco.

I remember there was this one thing called speed-dating for co-founders. The most hilarious thing. Like I did not understand it. I was like, what? Because I had a co-founder and she was like a dear friend. And I couldn’t imagine just like speed dating and finding some human randomly, who you might want to build a business and spend a million hours with blood, sweat, and tears.

But I think it works for some people, but I just bring that up because people do realize, oh, this is hard to do alone. On the flip side to your point. It can go really well or it can go not really well. So I think vetting that human, putting some things in place that allow you to unwind something. If it’s not the right human. Those things are all really important.

[00:16:01] Natasha: And today is the team that you’ve built now, taking on the responsibilities of all the things that you need to do to run a business, right? You have to hire, I’m assuming at this point, not only do you have a bookkeeper accountant, you probably have a controller, a CFO.

[00:16:19] Nichole: We have lots of humans now. Not lots of humans, we’re still a smallish team, but we’ve got someone in charge of tech.

We’ve got someone in charge of finance and someone in charge of onboarding in place, all of those things. And I still am really involved in product because I have a hard time letting it go. It’s who we are. So I work closely with in day-to-day contact with engineers and stuff, but they’re just telling me what they’re doing.

I’m not having to direct them. They’re just keeping me posted. The team is so much fun, actually. When you start in the trenches and you get to slowly come out. For me, I get to spend time on other things like strategic things. And it’s such a. And it makes me super grateful for my team, because I know what they’re doing.

A lot of what they’re doing is what I used to be doing.

[00:17:03] Natasha: How many full-time employees do you have at this time?

[00:17:06] Nichole: Full-time, we have eight and then we’ve got probably a similar number of contractors.

[00:17:10] Natasha: Sure. So fast forwarding to present-day, no matter how successful you are in your business, every business owner is going through figuring out a challenge. What is that one challenge right now for you?

[00:17:26] Nichole: Yeah. I think that challenge is we grow a lot every year and a lot of that growth is result of word of mouth because we’re a group payment platform. I send it out to my PTA, 300 new humans, know about it on something really cool. And that’s great. It can make you a little less sharp on the marketing front, or really focused on a number of things this year.

But now that the world is looking a bit more normal, we’re really focused on getting clear on what the marketing strategies are that we can affect, dump more money into and get a certain result. Basing it more on data and doing more experiments. It’s something I’ve done a fair amount of marketing in my past.

And just as of recently, I’ve realized I need to let this go. There are humans who can do this way better than me. And so we’re trying to do the right talent. Now you’ve brought up..

[00:18:18] Natasha: Do you outsource for digital marketing or sales funnels or anything like that?

[00:18:24] Nichole: Yeah, we do outsource for digital marketing. We don’t use an agency, but we use a human who is really good.

And we’ve gone through a number of humans and agencies. We’ve done different things at different times. I found that as equally challenging as hiring engineers.

[00:18:40] Natasha: I agree. I think this is great because everyone listening, they have their own challenge and whatever it is, sometimes people feel very alone. But I was asking you about the challenge of hiring people outside of what you’re really good at engineering and not knowing the language, but figuring out digital marketing and figuring out all the spokes on the wheel that aren’t in your wheelhouse.

One of the things is trial and error. You have to be able to be willing to take a chance on someone. If it doesn’t work out, try to make it work out. If it doesn’t work out, then pull back and re-engage with someone else and not be afraid of continuing on that. And then one day you find the perfect fit and that’s amazing! Until that perfect fit decides to change their life and leave for whatever reason.

[00:19:30] Nichole: That’s so true and it’s hard for me to not waste money, but I’m a frugal spender. And I’m like, it’s always “Got to give this person a chance.” It’s a constant, inner dialogue that I have and, or beating myself up mentally “Oh, I hired the wrong person again.”

Like “I can’t get this right.” That thing happens. But then I get myself out of that.

[00:19:51] Natasha: Hiring is a skill and art and science that in the 20 years that I’ve been in business, I’m an expert at doing it a lot. Sometimes I land like the most incredible win, and sometimes I don’t. And I think it’s too multilayered and too complicated for someone like us to do at the very highest level.

And that’s why some corporations have people that are just very, that is what they do. That’s what they focus on. They’re either using the topgrading or the WHO method or something like that. And they really know how to distill and source and qualify the right people. But that is a skillset that is really present in smaller businesses and it’s really expensive to outsource.

So thinking back to the beginning of this year, as we were coming out of the pandemic and you were really focusing on what you’re going to do this year to scale and grow, is there one major strategy that you are focusing on this year?

[00:20:57] Nichole: For growth? No’s the short answer. However, we’re investing resources in digital marketing and content. If I had to say, and we’ve got a lot of scrappy methods that we always do that we’re investing in more heavily because the world is normalizing and everyone’s trying to move online. So we’re doing all those things, but we are, I would say I and our marketing folks are making a concerted effort to be like, we’ve got all these humans.

We get to talk to them. What’s focused on content. And let’s see if we can get digital rights given.

[00:21:27] Natasha: And are you focusing on Google or Bing ads or social media or both?

[00:21:34] Nichole: I would say Google and social. It’s display retargeting, Facebook. Our users are on Facebook.

[00:21:38] Natasha: So the last question that I have for you is when you started Cheddar Up and you knew it was a viable product, did you have an exit in mind?

Are you building to sell or are you building to have a legacy brand that your kids and your co-founder’s kids will take over? Did that come to mind or has it come to mind?

[00:22:00] Nichole: Yeah, it’s different. Very beginning. If I’m really honest, it’s I want to build this really great thing and solve this really great problem and sell it to someone and make it all worth it.

That’s the short version. So yeah, I think that is the plan. I don’t think I’ll do this forever, but I want to get it to a point where it’s a household name and everyone knows we’ll just use Cheddar Up is a group thing, right?

[00:22:21] Natasha: I bet with the clothing company, you didn’t start that with your sister thinking we’re going to make this into this incredible thing and we’re going to sell it.

Someone’s going to buy it. And we’re going to exit.

[00:22:34] Nichole: Yeah, not at all. We were having fun then. It was like, “This is fun. And this seems like it’s fun to create and let’s give it a whirl.” I was quite a bit younger then, it was just like, I dunno, I just, I didn’t even think it through that much. I also had babies, so it was just whole different time of life and yeah, no.

A lot has been put into this. I have investors, I spent months away from my kids for it. Like it’s just a lot. It’s been not to get all weird, but I’ve given up a lot for this. So it needs to turn into something. It needs to be worth it.

[00:23:09] Natasha: That’s great. I think most entrepreneurs that start with a heart-based like I’ve got to do this business.

They’re not thinking of an exit in mind. I know for me, it never occurred to me. In fact, I felt a little put back if somebody said, “What’s your exit plan, are you going to sell?” And “Sell? This is who I am.” So I would assume with a company like yours with investors in the SaaS model and such, it’s not like that.

Yes, it is one of your babies. It’s one of your developments, but it’s a different kind of thinking.

[00:23:44] Nichole: It is. And it is 100%, probably to a fault, part of my identity. Like I am the Cheddar Up lady. It is my third child. I love it so much. And I spend so much time on it. But no, we’re going to get it to work and go, and then we’re going to let it spread its wings.

[00:23:59] Natasha: You’ll become a serial entrepreneur in that you start another something after Cheddar Up.

[00:24:05] Nichole: I’ve thought about that a lot. Yes, I do. I do. I think that I’m just going to take a big old break and kick my feet up, but I know that is not in my DNA. Get stir crazy and like I’m up.

[00:24:16] Natasha: I hope you learned something about building a FinTech SaaS company, even though you might not be tech savvy, if there’s a will and great talent and partners, there’s a way. For more information on Nichole, please go to the show notes for your listening to this podcast.

For more information about me, go to my website, Thank you so much for listening. I hope you loved the show. If you did, please subscribe. Also, if you haven’t done so yet, please leave a review where you’re listening to this podcast now. I’m Natasha Miller and you’ve been listening to FASCINATING ENTREPRENEURS.

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