In this episode of Franchise Masters, Dru Carpenito chats with a dynamic entrepreneur who owns and operates nine Crumbl franchise locations. Get ready for a deep dive into the rollercoaster journey of scaling a high-growth, fast-paced franchise in the booming cookie industry.
Shideler Bennett shares behind-the-scenes stories about the challenges of rapid expansion, from managing supply chain disruptions to building strong teams across multiple locations. You’ll hear about the systems and processes that were pivotal to handling such rapid growth.
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The Wild Ride Of A 9-Unit Crumbl Franchise Owner With Shideler Bennett
Welcome to the Franchise Masters podcast. I’ve got a Crumbl franchisee, not just a single-unit operator, but a ten-unit operator. Shideler Bennett‘s here to talk about his journey, the rise with Crumbl, the success there, and all the other stuff he’s got going on in the franchise world. Shideler, welcome. Glad to have you.
Thank you for having me. It’s an honor to be here.
Crumbl Franchise: Riding The Unicorn Wave
You know how franchising is, like, we’re all one degree of separation away from each other. It’s the way it works. You’ve been riding the latest unicorn franchise to hit the franchise world in the past 5 to 10 years. How the heck did you get into this game? Stumble across Crumbl? What’s that ride been like?
I didn’t ever know. I cleaned pizza ovens with a buddy of mine, Domino’s Pizza. They close at midnight, and then we’d go in and clean the hoods, take the ovens apart, and clean all of that out. I remember seeing the weekly sales that they would have on the wall and being fascinated by the numbers of all the different stores that we would go in. I’d be like, “This store crushes compared to these other stores.” You could tell by how dirty the oven was. That’s the earliest memory I had of franchising, being like, “I need to own a franchise one of these days.” That was my started from the bottom, love to make it kind of thing.
Franchising was not on the roadmap. I was doing insurance. I’ve always been passionate about finding a way to build passive income. I thought I was going to do that in the agency model and ultimately fell into the opportunity. Crumbl is a Utah brand, and people that I knew closely had got involved. Back then, the stores cost $300,000 to build out. Not crazy, but you had to get creative to get the funding. A lot of the early franchisees were borrowing money from friends and family. They were getting scrappy. We did some credit cards, did anything we could to get them open. The further you got along, the more professional it got, the more expensive it got, all these things. But early franchisees, we’re talking the first hundred, I would say, opened them for definitely under $400,000.
They would do that in the first year, ten months in profit. People were just like, “This is unbelievable.” It felt like a gold rush, where people would get what they could. That’s my experience, where we saw the success, essentially got in, and said, “Give us what you’ve got,” and ended up starting in San Diego. I had an operating partner that moved out there to oversee the operation. My family was growing, we had one child, and then another one on the way during this time. I felt like we made every possible mistake. We were coming out of COVID. The contractor that we had was lying about progress, was saying that permits were horrible in California and in San Diego in particular. But then, there were always these COVID excuses.
This is your first experience, first store?
Yes.
You chose not to open in your backyard in Utah? You had to go to San Diego?
That was what was close. We took what was given to us.
What number of franchisee were you?
I signed my ADA at the end of 2020. We’re coming up, this is year four from signing that. We signed that and had to be one of the first, I don’t even know if 50 units were open. We were really early. What happened, though, is because California was some of the first stores to try to open, it took us a year to get those first stores open. January of 2022, I was talking with my wife and some of the investors, and we were looking at the updates that the contractor had given us and the operator. You can’t blame the operator, but at the same time, he had never managed construction. To anyone, you could tell that it was not where they said it was.
I got in my Toyota Tacoma and drove straight to the store, just on a whim. I can show you the video of me getting there. They had delivered all of the large equipment. It’s sitting in a maybe halfway-done store. There’s no way you’re being productive in a construction crew navigating around all of this equipment. My heart sank. It was a horrible feeling to just know that thousands and hundreds of thousands of dollars were on the line. I had brought people into this. I was the one that was saying, “We need to do this. We can’t miss out on this.” Ultimately, I turned to my wife and said, “I cannot leave until this is fixed essentially.”
You have a little one on the way?
Yeah. We have one child and one on the way. I found out the gender of my second child while living in San Diego over Zoom because that’s just what it was. From then on, we really dove in together, and it was bonding. It was a bonding experience. We did everything, from plumbing to electrical. I did the low voltage myself in all of those stores. To say that, I joke that in one year, not one physical year, but in a twelve-month span, we opened seven locations across three states, and we did every facet of the work. I felt like I got a decade’s worth of experience in those twelve months.
You opened seven stores in twelve months?
Yeah.
How many states?
Three.
How the heck did you do that? You guys did the build-out yourselves?
In California. In the others, we had contractors. In California, we finished the last few. My uncle came down, was working with us. The work that happened was literally seven days a week. Even on Sunday, we’d go to church, and then we’d go back to the store. I remember tiling stores late into the night. We were painting, we were doing everything.
One of the lowest points was trying to get the first store open. We have these big, white, beautiful countertops that are at the front of the store, where people are checking out. Also, an area where we do everything is baked in-house. The city inspector comes in, measures the counter, and it is three-fourths of an inch too high, which would then make us liable for the ADA requirements for the handicap requirements. This is one full, huge piece. We had to basically lift up the entire countertop that had been stuck down, everything. This is a waterfall countertop, and we had to cut off basically an inch from the entire thing to then put it back down.
I just remember the inspector saying, “It’s not going to work. You’ve got to redo it.” All of us, it was like tears. It was just all of these sad because, with Crumbl and most brands, you have to get it approved by the brand, saying it looks good to open. We were trying to make that date by the following day or something like that so that we could be approved to open in two weeks. We missed another timeline.
Again, this is working around the clock. We’re doing everything possible at this point to make up for the contractor stealing our money, stealing our materials. We’re all working on it together. I could list off, we don’t have time for all the issues. We had a guy drill a hole for the plumbing, go directly through the main power line of the building, which should have killed him. He was standing in water, and it just took the power out.
Just issue after issue. We ended up opening those California stores, basically three of them, within eight weeks of each other. Just so much baggage. I tell people now, I go to San Diego still, and the stores have completely turned, very profitable, wonderful businesses, but I still have PTSD of living there and going there and just feeling like, “I’m going to do this and hurt everyone involved. I’m going to hurt my family.”
I was trying to be retired by 30, and I didn’t realize that I could put myself in debt a million dollars by 30, and that’s so much worse than starting at zero. You’re digging out of a huge hole. Hopefully, that sets the tone of how serious this got. Fast forward, now, things have totally improved. It’s given me a lifestyle that I always wanted, and it’s allowed me to now start buying more businesses, start other businesses, and go from there. That is what I lived through for the last couple of years. Not to mention, when we got these stores open, we saw sales drop out of nowhere when everyone was feeling the pinch on the economy.
You bought a franchise. None of that stuff’s supposed to happen, right, Shideler?
The saying of, “Would you do it over again?” I would never want to relive what I went through. I still don’t know, is it going to be worth it? One good year does not make me think we’re through the woods either, right?
Crumbl Franchise: One good year does not make me think we’re through the woods.
Yeah. You got three in eight weeks open in California. Meanwhile, I’m sure you had others open or opening. Is Crumbl still flying high at that point, or had the, we’ll call it the dip that everybody reacted to way too aggressively, had that happened yet?
When we were opening the stores in California, we opened the first one. It opens, and it’s crushing. Week one, doing revenue that no one thought was possible in that amount of square footage. Eight weeks later, we’re opening another one. Again, really strong opening. By the third one, we open it, and it was a good opening, but you could feel something had shifted in the market.
By that fall, that’s when you really were like, “This is really serious.” The sales were dropping to a place where these build-outs then became so much more than we had expected, over budget, that you’re looking at this saying, “If I have to close a single store, we’ve got, call it, $2 million in debt across three stores. If I close one, I don’t see it. I’m not making money on this ever.” Running a business to pay debt, no one wants to do that.
Anyways, it declined. 2023 was this year where we were very lean. It tested all of my partnerships. We lost two of the three operating partners that we had, which, in retrospect, was a huge blessing because then it required us to use the same operating partner across all of the groups. She’s just been a blessing, we’ll say.
That also standardized our whole operation. Now, we are very professional in our management. This year, that’s actually something I’m needing to learn, go talk to other multi-unit franchisees, see what they do as far as structure for a management company, and just say, “We’re bringing VAs in, we’re bringing new technology in, and we’re really corporatizing what we’re building to be able to expand.” The goal now is to get to twenty within the next couple of years.
The goal is to get to twenty. The sales dipped, but what happened after they dipped?
Sales dipped. 2023 was a sobering year.
It sounds like 2022 was a sobering year.
There was no high point.
You got open. You got a little taste of the glory when you had two good stores open.
I didn’t even really get to enjoy it, honestly, because the stores were doing such high volume that operationally it was very difficult. Trying to dial in your labor and your food costs when it’s so different, and we’ve got multiple operators running the business slightly differently. 2023, refiner’s fire. Sales drop. Operations get more and more dialed because you’ve got to operate at a lower level. 2024, you can see that things are maturing. The brand is leveling out.
A lot of people talking crap on Crumbl and basically saying it was a trend, all of these different things. We’re starting to see the sales level out and be to a place we’re happy with. The last part of this year, sales jumped and have been wonderful, to a place where I’m like, I really believe in the leadership of this brand.
They have doubled down on technology the whole time. It was really cool to see not only us as franchise partners, but Crumbl being very transparent and really everyone saying, “We’re doing the best that we can. Here’s what we’re trying. Here’s what we’re learning.” I look at anyone who’s been through it now and that’s left, it’s baggage. I don’t know how to describe it other than we all know what we all went through, and you’re better for it now.
The Rapid Expansion Of Shideler’s Crumbl Franchise
You probably molted a few new mindsets going through that journey that you did, but you came out. Can I ask you, because I think this is an interesting question in terms of your guys’ strategy to go big out of the gates? What was it that led you guys to decide to open that many stores within a pretty short timeframe relative to probably your development agreement, or could it have been an agreement?
Technically, that was three separate development agreements with three separate partnerships, essentially. Crumbl did not, we had just more interest in people that needed help, that wanted to do Crumbl. We couldn’t be on multiple agreements at a time. They didn’t want us to do that. We basically told people, “We will come in,” and we were already doing this. “We will help you do it.” Handshake, that they would give us equity on the backend for doing all of this work.
It was not intentional. This was not something, it was just that people knew they wanted to get involved. Many of the franchisees did not have any experience franchising beforehand. Again, this is what’s so different from our experiences. Crumbl basically said, “Take it or leave it. We have so much interest that that’s what it is.” People were just saying, “We got approved. We have no clue what we’re doing essentially. Please help us.” We never did discovery days. We never did, I’ve never done a discovery day. I’ve never experienced your traditional franchise experience. It was like, “You’re approved for this brand. Do you want to do it? Sign today, pay your fees, go.” It was like, okay.
It was the gold rush, and you were right there during the thick of it, in terms of having to make a decision whether this was the right thing for you or not. How could Crumbl pull off supporting, because you said it was a thousand units? They opened in five years. How do you think they pulled it off? Aside, I doubt every franchisee was willing to do everything that you did to get your stores open. I could be wrong on that, but what do you think it was?
They kept us accountable, for sure. There were, without a doubt, growing pains. They couldn’t hire people fast enough to keep up with the onboarding. I’m asking my onboarding person for help, and they don’t know what they’re doing. I’m like, “No, just put me in contact with the person that can answer my question.”
There was a lot of pain that way, where, as franchisees, you are problem-solving everything. I hear people now, and they’re like, “I joined the brand, and the franchisor is helping me with the real estate.” No, we did everything, and they basically said yes or no, or, “Yes, actually, wait.” It was very much the early franchisees paved the way on this. Now, I would say Crumbl is really great at valuing that, but in the early days, it was, everyone was keeping their heads above water.
It’s a wild ride.
Very unique path, for sure.
For anybody listening, what we’re talking about is the level of growth, that speed hasn’t been done in a very long time. I don’t even know what a close example would be. Maybe not even Orange Theory during their heyday, because it took them ten years to get to a thousand units.
People, this isn’t a 60-day buildout. These are entire buildouts. To open a store in six months is wildly fast. To have so many people doing that, that led to people signing bad leases. That led to people doing stuff that they shouldn’t have. But there have been very few closures. To be honest, I think that many of the closures that did happen, they closed at peak pain, where if they maybe could have fought through to the next year, they would have been just fine. It’s easy to look back in retrospect now.
We talked a little bit offline about this, but the thing they had going for them was the cheapest money in modern history. 0% interest rates, all the COVID money that was coming in. That’s another piece, anyone who was an early franchisee got to take advantage of all of the government programs that came out at that time. With them being able to print money immediately, they just were reinvesting. A lot of these were built out with cash. Social media, Crumbl was going viral all the time. Now, you look across all their platforms, and millions and millions of followers. Show me another franchise that’s got that behind them.
I got to the kids too. Every week, my daughter asks me, she’s like, “Would you take me to Crumbl?” I’m like, “No.”
What people don’t know is the level of investment into technology as well. Crumbl got an offer for $400 million from Chick-fil-A to license their technology in year three.
Just to license the technology?
Yes. Jason McGowan, the founder, he’s a genius. He’s a wonderful leader who is very future-forward thinking. We’ve dealt with tons of bugs the whole time, dealing with their own technology rather than just getting a third-party option. Now, if you go look at our app and you go send cookies to someone, I would put our app against any app out there on the level of experience that you’re going to get, seeing those cookies get delivered, doing just the interaction. It is so user-friendly, and then on our side, we’ve got amazing data points that we can see as franchisees, live sales, training, all of these things. You look at it, and you’re like, this is very impressive.
Testing Partnerships Early: Lessons Learned In Franchising
They literally put the car together. They really are going really fast. Most franchise companies are doing it at a much slower pace relative to where Crumbl is. Obviously, it feels like a fast pace within that franchise system, it’s all relative, but that’s an amazing story. You said it earlier, and if you don’t mind me, I think I would like to just dig in on this if you’re comfortable with it. It tested your partnerships at an early stage. I would imagine that was an interesting experience as well.
That’s one of my biggest learnings from this. Dealing with a drop in sales, that’s one thing. Dealing with a growing company, that’s another thing. Dealing with someone that is incentivized on a vested equity schedule, and they can see the rate of work that’s required increasing while the level of value of their equity is decreasing, is a very tough thing. What I didn’t mention is, as we were building out, we no longer felt comfortable taking salaries, and we were only paying the operator a salary. We got to a point where we had to say, “You got to take a lower salary for us to keep going.” The investors had put in way more money than they had wanted. Getting funding was way more difficult.
Crumbl Franchise: Dealing with someone who is incentivized on a vested equity schedule while they can see the rate of work required increasing and the value of their equity decreasing, is extremely challenging.
The strife between partners added an entirely different dimension to it because if you’re also working through partnership challenges, when the partner you’re working with is the operator, their attention is not on the store if you’re dealing with that. Operationally, everything suffers. I would say the struggles that I talked about, not just with our group, but with many groups, was that partnerships were falling apart, and the eye was off the ball dealing with that. It felt like as people could go back to just focusing on improving the business, once the partnerships got worked out, things were much better for all parties involved. It’s just better to move on in many cases.
Business is business, but when it’s small business, it’s also very personal a lot of times too, from that standpoint.
Friends and family, that’s who was involved in it, and people you want to be in business with. I really did, at certain points, just have to be like, “I really do care more about these relationships than I do about any financial upside.” I didn’t feel like my equity was going to be worth anything. I wasn’t getting paid anything. I was like, “I make zero money from this. We’re all struggling through this. What’s the solution? What do you want? If you want out, great, tell me.”
The challenge in that scenario, when sales are dropping, things are challenging, and profitability is dropping because the eye is completely off the ball, is that your business’s value is at its lowest. Then, the amount of debt was staggering. For someone to say, “You need to buy my equity,” and for me to be like, “There’s no value. I don’t know how to show you this any more clearly, but there’s no money,” and so that’s the real spend hours on.
The real challenge is when your business value is at its lowest, and there's no money to show for it. Share on XI got a follow-up question because I think, especially for folks that are thinking about getting into franchising, just like you’ve paved the way for a lot of other franchise owners in the Crumbl system to take the punches, I’m sure there were a lot of best practices that came up from your experiences and everything like that, that everybody benefited from.
Very gracious franchisees helped us as well. We went out and visited people and did everything we could to learn.
As it relates to people who are thinking about joining this wonderful franchise community and thinking about getting involved in a franchise, and they’re thinking about starting a partnership to do it or forming a partnership to do it, looking back on your advice and your experience going through all this, what advice do you have for anybody thinking about doing a partnership and opening a franchise?
A very clear example of this is me bringing on an operator so I didn’t have to move from Utah, only to end up living there for six months. If I would have just said, instead of paying an operator salary, I am going to move my family, or I am going to visit more often to own an operator, to oversee that and to open these stores myself, it would have saved me so much time, struggle, energy, and money, frankly. I think that’s the other part, you got to understand that if you’re the one putting it together, and especially if you’re bringing on investors, you can’t leave it to chance that someone is going to do their job when you are answering for the money.
There are great partnerships, and they’re definitely not all created equal, but what I would just say is, if you can figure out how to do it, it is much easier to come in. From a partnership, you can bring someone on really good and pay them a salary plus some profits once it’s opened and get a great person. If you start from day one saying they’re going to get sweat equity, people never value equity like they could or should, and sometimes they overvalue equity more than they could or should. It’s kind of a losing scenario to offer equity, especially when someone doesn’t put any cash into it, because then they just have warped expectations.
Crumbl Franchise: There are great partnerships, and they are definitely not all created equal. However, if you can figure out how to do it, it is much easier to come in.
I think there is so much wisdom in that. What you went through, you mentioned it, that out of all of this emerged an amazing operator for your company and operation. The one that operates the three markets for you. I talk to a lot of people about starting businesses and getting into franchising, and everybody wants to do it, but a lot of people, the circumstances just don’t enable it. People think it can be passive, and people think it can be semi-absentee when it really can’t.
People have money, they just don’t have the time piece of it. I tell people, I’m like, if you want to do this, you’ve got to find an operator. Finding the money is easy, that’s the easy part. Finding a good operator is very difficult because there are few of them out there. If you do find somebody that you know and trust and have worked together for a long time or have known for a while, they have to put some skin in the game. Otherwise, your entire operation hinges on that one person. I don’t think people listen to me, but that’s funny that you say that. The skin in the game is the big piece to pulling off the operating model.
I think so. It’s just so much easier to do things yourself and then bring people in to try and help incentivize them and help them see the future forward. Anyone that is using retirement dollars, I also know people that have got taken advantage of just giving it to a fund or whatever else to try and get access to some franchise exposure. Franchising, it’s tough to get a great return if you don’t understand who you’re working with.
Franchising is tough to get a great return if you don’t understand who you’re working with. Share on XIf you’re not willing to operate at the end of the day to get new locations, even buying existing ones, I still think you got to get in the game to do it the right way, to protect your investment and make it successful. I think that’s what you’ve done. I can’t imagine how many hardworking people with really strong work ethics and grit would have said, “I’m out,” at some point during your journey.
I felt backed into a corner. I truly cared more about getting my investors their money back. For me, this was also the first time people really bet on me. I’ve raised money before, but this was on me. This was on me and my partner. I definitely, if someone could have taken over the liability, given all the money back to the investors, and I could have walked away, I probably would have. I’m grateful that that didn’t happen, but it was just like, I want to be known as someone that does the right thing, that takes care of the people. I take that very seriously. If you’re going to give me the money, I only will take your money from an investor if I am confident that I will be able to produce the return that I am saying I can obtain. For the people that didn’t have skin in the game or feel that obligation, they did leave.
Growth Plans: Expanding To 20 Units And Beyond
A few-year journey to get to this point. Things sound like they’re going great. More power to you and all the work you put in, the sacrifices you made to get to this point. You mentioned that you have plans to grow it to twenty units. Are those going to be new locations, or are you thinking of getting there a different way?
Most likely acquisitions. We slammed all the brakes when things slowed down. We’ve been at nine stores for the last year or so. We’ve got other opportunities to fulfill our ADAs. We’re working with Crumbl closely to identify where that will be. We’ll do a couple more developments. There’s really not much room left in the country. There are no new opportunities for someone to come in. There are people changing, getting out for different circumstances.
A lot of people I know had to go find different work or create different businesses to make money when things were tight. Some of those businesses have taken off. That’s some of the people I’m talking with about acquiring their stores. They’re like, it’s good now, thankfully. Knowing that growth is limited, it makes more sense to sell and focus on another business that’s less hampered by growth. We acquired one that we closed on.
Congrats.
Thank you. It was anticlimactic. I did a post about it, but one day it wasn’t our store, and the next day it was. It was running smoothly.
That’s the easiest opening you had.
Without a doubt.
You earned it. You earned every bit of it.
When I say that, I’m like, the amount of work and time and struggle that has gone into developing a store, and then to buy a store and have it just produce. I see a deposit a day later, and I’m like, let’s do that. Let’s do more of that for sure. I’m putting it out there to any Crumbl owners, I’m trying to grow in my markets. I’m trying to acquire any stores that have three or more in a different market than where I’m at. I’m interested. My goal is to build out the management company that will support all of these, essentially. That’s just our personal thing, because now it makes sense to have everything standardized. We’re hiring virtual assistants. We’re getting new technology that makes us just operate at a better level, manage our stores better, and it’s really fun. It’s a fun spot to be at.
Exploring Funding Options For Franchise Acquisitions
You’re in growth mode through acquisition. I love it. How are you using traditional funding sources for those acquisitions? Are you getting creative with some seller financing, or what are you thinking?
Yeah, so this one I just purchased was seller financing. I think we put $20,000 into fixing things and doing different things out the gate, but to buy a store for that, as opposed to what I’m used to, is a huge improvement, and it’s just seller carry. I’ve got another two under LOI, and those would be more traditional funding. Another thing that I tell more franchisees is I am taking a much more prudent approach to the debt as well.
We are going to aggressively pay down debt. The cash flow is wonderful, but I still have scar tissue from feeling like a store was going to close and I’d be left with so much debt. The goal is for us to have each store paid down to about 50% of the total project cost, and then, at that point, we can let the remainder be paid off slowly. Now that I’ve seen what feels to be kind of the worst of it, we’re building and trying to be very prudent that way.
Aggressive at the same time.
Growing, but also paying it down.
Franchisee Acquisitions: Timing And Strategy For Success
I love it. What’s your experience been with some of these acquisitions of other franchisees? Have you had to plant a seed and let the seed sit for a couple of months, and then they come back to you, or have they been quicker than that?
I had a lot of conversations, and now, knowing where I’m at, I wish I would have purchased more in the past year or so. I’ve really just started to put it out there. The ones that I had have been a pretty quick conversation. I need to get out. I make a fair offer, and they just accept, and we can move things forward. I would anticipate over the next couple of years, it’ll be a lot of that, building relationships and just saying, when you’re looking to get out, I’d love to pay you a fair price.
It’s really cool when you can understand what your organization does from a management point, and then I can really make an offer based on revenue and less based on EBITDA, unless traditional financing doesn’t support the EBITDA that they have, which only works in my favor. Say the bank can’t even give me the money, no one else is going to get this done. I can just know, this is where my profit is on this opportunity, and it just helps me underwrite it differently than someone else.
You guys have got your management and operations so dialed in, and you continue to improve them, that you don’t even really need to see what the full P&L looks like. You could just look at a few numbers and get a sense of if you guys can come in and improve it and get it where you think you can get it to be.
Obviously, I look at the P&L. I look at the balance sheet. I need to understand the leases, where those are at. The main things that I need to know are, what is the total sales? What is the percentage of rent for that? Is it a favorable lease? From there, I obviously check to see what their net operating income or EBITDA is, but I’m less concerned about that because I know where we should be able to run it at. If I can justify the price, then I try to make it happen.
Achieving Passive Income Through Crumbl
Dialed in, my friend. I love it. You started this conversation saying that you had a, I forget the word you used, it was a fascination or a goal of passive income. How do you see your Crumbl operation and business fitting into that goal, if it even is still part of your long-term goal?
I made a life goal actually only maybe a year before I got into Crumbl, and I got pretty good clarity on what I wanted. It was a net worth of $10 million. It was to have $200,000 passive by the time I was 35 and then have everything, all the debt in my life paid off, except for everything that’s a non-producing asset, paid off. A couple of these very specific life goals. The reason I mention that is that is what allowed me to evaluate any opportunity that I was reviewing, can it help me hit those things? Can I see a path to that? That’s where Crumbl came in.
As soon as we saw the opportunity, we said, if we’re going to do this and we go fast, I can very quickly see how that helps me achieve those goals. Crumbl running effectively will do that. I don’t see us selling anytime soon unless someone came and gave me a crazy offer. With how I think Crumbl looks at private equity, I can’t see them loving that. We’re buckled in. I see us, at least for the next three years, heads down, just growing. That’s me in three years.
Earned it. Are you doing any other alternative investing with passive income, or are you just laser-focused on Crumbl?
Obviously, investing in franchising has been the most tax-efficient way for me to use my funds right now, but I’ve also invested in short-term rentals. In doing debt and helping people secure that, I get a lot of different opportunities for investments that come across my desk. I really like the short-term rental one because I got access to a property that I use now in southern Utah. It gives me a monthly cash flow. I got depreciation that was accelerated because of the nature of the short-term rental.
This year, I invested in and helped advise a trucking fund where, by putting the money in, again, you get accelerated depreciation because of the trucks. That one actually has an even better return. It doesn’t have the benefit of staying at an Airbnb, but it’s about 2% to 3% per month on passive investment, which is a heck of a lot easier than running franchises.
Dealing With Offers From Outsiders
Well said. You mentioned it. Have there been any crazy offers creeping into the Crumbl system or your world from outsiders trying to come in, the ETA bros or the private equity bros coming in?
I would say before there was the first down year, there were crazy stores. I do know that some Crumbl owners got in, opened their stores, ran them for two years, and I think they were selling for 5 times off of just ridiculous opening numbers. There were a few people that did that and made it happen. I also know plenty of them that sold at the very bottom and now are kicking themselves because they missed out on the rebound. Right now, I would say I think people are starting to dip their toes back in for sure.
I think with Crumbl too, if they have an opinion about outsiders, if there’s a certain fit they’re looking for, for anybody outside the system to get in now, because you can only get in basically through buying existing operations, I would imagine they would much rather see existing franchisees who have proven to be great operators expand that way versus bringing in the unknowns.
That’s what we’re trying to do. We’re trying to be very open with them to say, what can we do to be a great operation? We love constructive feedback. We’ll do anything to improve and reinvest in our operations to be a great partner. There’s definitely give and take on that.
Would you say that you’re proactive in maintaining a relationship with the Crumbl leadership and influencers inside the organization?
I wish I knew how to be more proactive. I would say, to the extent that we try to just be really great about sharing what we’re doing, what we’re trying, and any opportunities to help them, where if we can be a trial location, or we can test things, or whatever else, then we are ready and willing to go the extra mile. If someone else has experience on how to do a better job of that, I’m all ears.
Diversifying Interests: Expanding Beyond Crumbl Franchising
You’ll figure it out. You figured everything else out. What other stuff are you doing now? You mentioned you’re doing some lending, doing some other stuff. You’ve got the SaaS thing going. What are those things?
When we had the downturn, I started making money brokering debt and have built a business with some amazing partners that is less franchising and more creative finance. Basically, if your bank isn’t helping you get a transaction done, people come to me and my partners, and we find a way to do it. We’ve got a platform of investors, high-net-worth individuals, debt funds, and family offices that can give more creative solutions.
Software side, my business partner, Taylor Byington, shoutout to him. He’s been grinding on this business, CoverPanda, for the last couple of years. This is built off the back of many of our learnings. We made so many mistakes. We created our own payroll and bookkeeping solution for our group and ultimately just felt like, why do more franchisors not have the same support that Crumbl gives us? They don’t use technology.
CoverPanda really is built in a way to provide a more tech-enabled experience for franchisors and franchisees, to see their financials, to store their documents. You can do the services of payroll, bookkeeping, insurance, all of those things. It’s a really exciting opportunity. There’s a lot of interest from the venture community. That’s probably the thing I’m most excited about right now, growing Crumbl, growing that business, and just seeing all of the excitement around it already.
Is it an internal financial bench? It gives the franchisor access to all the finances running through the franchisees so they can provide benchmarking data and stuff like that? I’m describing it for you. Let me ask you, what exactly does it do?
For the franchisor, it is going to give them royalty management. It’s going to do the learning management system that they can share with the franchisees. It’s got all the reporting and dashboard capabilities to be able to see all of the units within the system. We then come in with each franchisee that’s brought on and help them through the onboarding process, everything from entity setup, bank accounts, bookkeeping setup, payroll, all of those things, so that they’re set up correctly. You’re asking one person or one company for help to do all of that, which saves people so much time and just eliminates the questioning of how to do all of these things because that’s not making you money.
For sure.
We were always asking those questions. It’s like you’re dealing with a bunch of different vendors, but none of them talk to each other. This also then provides the cleanest data from the franchisee to the franchisor, which can then drive performance.
Does it integrate with QuickBooks and the whole nine yards and other financial software?
It’s one of those that, as we’ve been building it, people are like, “I’m shocked that this doesn’t exist already.” There are management systems for the franchisors, like FranConnect, it’s the largest one, and a couple of others, but what we’re doing is very novel in the space. There’s a reason a lot of people are starting to realize what it could be.
Nice. Have you got any brands signed up yet?
We’re still building in stealth a little bit. You’ll start seeing that come on a lot more, but you know the Wolf of Franchises? The Crockett business that he had.
Yeah. We’re doing a similar thing. You are the guys that bought it. Got it.
Big things coming. It will be a big year. It’s a pretty clear path to $2 million in recurring revenue. So far, it’s just being bootstrapped the whole way.
That’s awesome. Congrats. Especially after the Wolf just retired and is doing something else, right?
Yeah. Patrick’s a great guy.
He is a good dude.
We’d love to find a way to keep him involved on the content side. Those are other conversations.
It’s a smart move. Well done. I didn’t know it was you guys that bought him. He told me he sold it to somebody. I didn’t realize it was you guys. Cool. That sounds like franchising tends to be ten years behind the rest of the business world with a lot of technology and software. He told me what he was doing. I think there’s one other player out there, but maybe not as sophisticated as he is.
Everyone’s taking a different approach, and it’s tough when you talk to franchisors because they want everything. That’s what FranConnect has done. They’ve been building everything, but we’re really trying to just be very good at the few things that we’re going to do right now, and we’ll eventually expand but for now, it’s been pretty effective.
That’s awesome. If you want to sell your Crumbl in certain markets, get in touch with Shideler. If you need money and your bank won’t give you money, get in touch with Shideler. If you’re a franchisor that is trying to implement some financial management systems into your organization, get in touch with Shideler.
If you’re an FSO and you need better onboarding for your franchisors, that’s the other piece there. There is a really cool way we can work with FSOs as well.
Might have to call you. We got a little one cooking. Cool. Thank you very much for coming on and being very open about your journey. I think there’s a lot to learn from people. Everybody is coming into this world from different experiences and different perspectives, but I haven’t heard many wild rides like the one you went through, so congratulations.
I have a lot of empathy in everything I do now, for sure, for anyone who’s willing to go give it a chance in business. That’s always my hope, that if we interact in a business setting, you’ll feel that I am not trying to do anything that would not be in your best interest. Because there are already so many other things that can go wrong, I’ve got to take care of you.
Well said. If people want to get in touch with you, what’s the best way?
LinkedIn, just reach out to me there. I’ve been trying to be really consistent. Send me a message, and we’ll find plenty of ways to connect.
Cool. We’ll pop it in the show notes for anybody who wants to get in touch with you. On that note, I’ll let you get back to it. Thanks, I do appreciate you coming on here and sharing.
I’d love to hear more about the FSL that you’re working on too.
You will. The whole world’s going to hear, I’m just kidding. It’s a mini. We’re keeping it small. I’ll let you roll.
Important Links
About Shideler Bennett
By my early 30s, I achieved financial freedom for my family through strategic franchising and funding—a journey I believe anyone can replicate in as little as three years with the right vehicle.
Here’s what I’ve built:
A portfolio of 10 Crumbl franchises generating $11M+ in annual revenue with strong net profit margins—all while spending just 10 hours monthly on operations.
With Initiator, I’ve facilitated tens of millions in funding and helped clients secure hundreds of millions in loan offers.
At Coverpanda, I’m working to revolutionize the franchise industry with a SaaS solution, aiming to grow it into Utah’s next unicorn.
How I Got Here:
Scaling multiple franchise locations quickly wasn’t easy, but it taught me invaluable lessons in resourcefulness and determination. I secured funding by leveraging:
Private capital, personal loans, and 0% credit cards.
SBA and conventional loans tailored for rapid growth.
This hands-on experience gave me a deep understanding of the complexities of funding and franchising, leading to the successful launch of nine locations (and counting).
What I’m Passionate About:
Today, I focus on helping entrepreneurs and investors achieve their goals.
My expertise lies in:
Securing tailored funding solutions for business growth.
Connecting high-net-worth investors with high-yield, reliable opportunities in debt lending, real estate, and franchise ventures.
Developing innovative software to streamline franchisor and franchisee operations.
Why I Do It:
I thrive on transforming complex challenges into simple, scalable solutions—whether it’s helping a business owner fund their first franchise or guiding investors toward opportunities that create lasting impact.