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Relaxed Leasing: Matthew Winston’s Journey to an “Easy Button” for Fleet Transportation
Veteran hospitality executive Matthew Winston is transforming how businesses lease shuttles and vans – with a flexible, nationwide model that puts client needs first and delivers vehicles at record speed.
A Homegrown Solution in Kansas City’s Transportation Scene
Kansas City’s thriving transportation sector now hosts a unique newcomer: Relaxed Leasing, a company that has rewritten the rules of commercial vehicle leasing. Founded in early 2020 by local entrepreneur Matthew Winston, Relaxed Leasing prides itself on making fleet leasing truly “relaxed” for clients[1]. In an industry where businesses traditionally had to hunt through dealerships or commit to rigid contracts, Winston saw an opportunity to provide a one-stop, flexible alternative. Today, his Kansas City-based firm sources and delivers vans, shuttles, buses, and more to clients nationwide without the usual inventory pressures or hard-sell tactics[2]. It’s a service that Winston – a 30-year veteran of the hospitality transportation world – likens to hitting an “easy button” for fleet needs[3].
Relaxed Leasing provides flexible, long-term leases for vans, shuttles, and buses. The company sources vehicles nationwide to meet each client’s specific needs without maintaining its own inventory, avoiding the hard-sales pressure typical of dealer-based leasing[2].
From the start, Winston built Relaxed Leasing on a simple principle: make the leasing experience effortless for the customer[1]. “We lease just about everything a business could need with an engine or motor,” he explains, emphasizing that clients can request virtually any make or model – whether a 15-passenger shuttle bus or a luxury SUV – and his team will locate it through their coast-to-coast network of partners[4][5]. Unlike traditional fleet dealers, Relaxed Leasing carries no vehicle inventory of its own, which means they have no particular stock to push. “What we’re pushing is, what do you want? And we’re gonna go get it,” Winston says of his company’s customer-first philosophy[2]. This nationwide sourcing model not only gives clients more choice, it also enables surprisingly fast turnaround times. Many customers are “pretty shocked at how quickly the vehicle actually arrives on their property” from the time they first reach out[6]. By tapping into suppliers across the country, Relaxed Leasing finds units close to the client’s location, minimizing delivery delays[7].
Matthew Winston: From Hospitality Veteran to Leasing Innovator
Winston’s entrepreneurial journey is deeply rooted in his 30+ years of experience in hospitality and transportation[8]. After attending the University of Missouri–Kansas City, he began his career in the fast-paced hotel and gaming industry of Las Vegas, working with Harrah’s Entertainment and managing guest services[9]. He later served as Director of Service Excellence at a healthcare hospitality firm, sharpening his expertise in patient transport and valet operations[10]. By the 2010s, Winston had risen to leadership roles in the shuttle bus sector – notably as a Vice President at a shuttle dealership. In that role he oversaw leases and rentals of shuttles, and even piloted creative programs like seasonal shuttle leases for universities. This rich background gave him a front-row view of the industry’s fundamental pain points.
“A lot of suppliers… really have to promote only their product,” Winston notes, reflecting on his time at traditional dealership-model companies[13]. Those firms often face manufacturer quotas and push specific brands or models, even if they’re not the ideal fit for the client. Winston realized that customers – hotels, colleges, hospitals, and others – were bouncing between dealerships to assemble a fleet, or getting locked into long contracts that weren’t easily adjusted. In his view, the industry was ripe for a more customer-centric approach. By launching Relaxed Leasing in 2020, Winston set out to eliminate those constraints. “I’m not subject to quotas… I’m catering to the client,” he explains[14]. If a hotel comes to him needing a 12-passenger van, he’ll find one. If next month that same hotel decides a different vehicle would serve them better, he’ll work out a swap rather than saying “see you in five years when your lease is up”[15][16]. Building flexibility into the business model was key. “Relationships are built through flexibility,” Winston says. His goal was to ensure that clients never feel “boxed in” by a lease the way they might with a conventional dealership[17][18].
Winston’s decades of industry know-how also taught him the value of speed and responsiveness. Having worked on the operations side of hotels, he understands that when a shuttle breaks down or a new van is needed, time is of the essence. Thus, Relaxed Leasing operates with a 24/7 mentality. Unlike many competitors who keep to banker’s hours, Winston emphasizes that his team moves “on more of a 24-7 basis, versus a Monday through Friday, 8-to-5” schedule[19]. That round-the-clock availability has been a differentiator, especially in hospitality. He jokes that often the first phone call from a hotel is along the lines of, “We need this yesterday.” Relaxed Leasing is structured to answer that call – often getting a vehicle sourced, leased, and delivered within a matter of days[20][21]. To streamline paperwork, they use electronic signatures and digital docs, avoiding any snail-mail or notary delays in the contract process[22]. All these efficiencies add up to a service that can turn a client’s urgent request into keys-in-hand sometimes by the very next week[20]. In Winston’s words, “people come to us and know that they’ve found the easy button” for acquiring fleet vehicles[3].
“Leasing Life Simple”: What Relaxed Leasing Does Differently
Another hallmark of Relaxed Leasing’s model is that the service doesn’t stop once the vehicle is dropped off. “We don’t just hand you the keys and disappear,” Winston says. Included in every lease is a consultative, full-lifecycle support package[28]. That means helping clients with vehicle licensing and registration across different states, connecting them with trusted maintenance providers, and ensuring preventative maintenance schedules are followed[29]. For many of his clients – say a hotel manager whose expertise is running a resort, not maintaining buses – this support is invaluable. “A hotelier is very good at what happens inside the building. Outside the building is not their expertise,” Winston notes. Providing a house shuttle is an expected amenity for a hotel or a hospital campus, but managing the upkeep of a shuttle bus is not in most clients’ wheelhouse[30]. Relaxed Leasing fills that gap: “We’re not just the easy button at the start; we’re the easy button all the way along,” Winston says, describing how clients can call his team anytime for help during the lease term[31][32]. Need guidance on warranty service or a quick repair? Relaxed Leasing will point you to a local solution. At the end of the term, they handle the vehicle’s pickup and even swap it for the next model the client might need[33]. This high-touch approach has created a sticky, loyal customer base. In fact, Winston is proud to share that to date they have never lost a client to turnover[34]. That kind of retention is almost unheard of, and it speaks to how much value clients see in the partnership.
Serving Shuttles from Campuses to Casinos
One reason Relaxed Leasing has found success is by zeroing in on specific market niches that have a pressing need for flexible fleet solutions. Winston identifies a few “sweet spot” sectors that make up the bulk of their clientele:
Hotels and Resorts: In the hospitality sector, providing guest transportation is often critical for high-end service. Many Kansas City hotels offer courtesy shuttles – whether for airport transfers or short rides within a radius. Relaxed Leasing supplies these “house cars” or vans that remain on property for guest use[35]. For example, a boutique hotel might lease a luxury SUV to chauffeur VIP guests to dinners or Chiefs games. Larger hotels near KCI airport might need 15-passenger vans to run constant airport loops. Winston’s team ensures the vehicles come outfitted to fit the brand (even arranging custom graphics or logos if needed[23]), and importantly, they offer to rotate models. In fact, Relaxed Leasing has curated a special “Luxury Hotel Collection” program by invitation, where a hotel can delight guests by cycling through different high-end vehicles every six months – one period it’s a Bentley or Mercedes-Maybach, next it might be a Range Rover[36][37]. All insurance, licensing, and seamless swaps are handled behind the scenes, so the hotel staff can focus on hospitality, not fleet management[38].
Colleges and Universities: Campus transportation is another major area. Universities often need shuttles for two purposes: daily campus loops (or parking lot shuttles) and athletics or event transport. Relaxed Leasing works with colleges that require minibuses or vans during the school year, but perhaps not in summer. They can set up a nine-month lease aligning with the academic calendar, an idea Winston first pioneered in his earlier years. Sports teams are a great example – a college basketball team might lease a 12-15 passenger shuttle for the season to get players to practice facilities and games[40]. With Relaxed Leasing’s flexible terms, the university isn’t stuck owning a bus that sits idle in off-months; they lease it for exactly as long as needed. Winston cites the college market as a “great space” that benefits from being able to choose different vehicle sizes or layouts depending on the sport or occasion[41].
Healthcare Campuses: Many hospitals have sprawling campuses or satellite parking lots, making employee and visitor shuttles essential. Over the last 20 years, hospital systems have expanded so much that parking often can’t keep up[42]. It’s not uncommon for staff (or even patients) to park a mile away and ride a shuttle to the hospital entrance. Relaxed Leasing provides hospitals with shuttle buses, often on multi-year leases that match the timeline of a construction project or expansion[43]. “Maybe they’re building a parking garage that will take 24 to 36 months – so they bring in equipment to shuttle people from an off-site lot in the meantime,” Winston explains[44]. By leasing instead of buying, the hospital can scale the fleet up or down as needed and avoid a capital expense for a temporary need. And because reliability is literally a life-safety issue in healthcare (imagine a shuttle breakdown making a nurse late to the OR), Relaxed Leasing’s end-to-end maintenance support is especially valued here[29].
Casinos and Entertainment Venues: In the entertainment industry, shuttles often cater to VIP guests and special events. Kansas City’s casinos, for instance, sometimes transport their high-rollers to events like football games or concerts. One local casino even maintains a luxury suite at Arrowhead Stadium and needs to ferry guests from the casino to the stadium in style[45]. Relaxed Leasing has provided vehicles for these purposes, such as executive coaches or plush vans, ensuring the casino’s best customers get a seamless, first-class ride. Similarly, for large events or festivals, organizers might lease shuttle buses to move attendees from remote parking lots. The key in this sector is the ability to turn services on and off for seasonal peaks – something a flexible lease can accommodate much more economically than either purchasing a bus or using ad-hoc rentals.
Across all these sectors, what these clients share is that transportation is critical but not their core business. They “have to offer it as an amenity, but they’re not really set up to pay attention to it” the way a transportation company would[46]. This insight is at the heart of Relaxed Leasing’s value proposition. Winston’s team doesn’t just drop off a vehicle – they become a behind-the-scenes partner making sure that shuttle program runs smoothly for the client’s end-users (guests, students, employees) throughout the lease. As a result, clients can offer top-notch transportation service without getting bogged down in the details. “That has really become the stickiness of what we do,” Winston says. Clients know they can “reach out to us at any time” and get a quick response[31], whether it’s a question about a maintenance light on the dashboard or a need to add another vehicle to handle unexpected demand.
A New Era of Flexible Fleet Leasing – and What’s Next
Relaxed Leasing’s rise comes at an opportune time in the broader vehicle leasing industry. Coming out of the pandemic, many organizations have been hesitant to sink big dollars into purchasing fleet vehicles, preferring more agile solutions. The global market for automotive fleet leasing is on a growth trajectory – projected to expand from about $26.5 billion in 2023 to over $35 billion by 2030[47][48]. A key driver of this growth is the “rising popularity of flexible and adaptable business solutions” in fleet management[49]. In other words, companies are increasingly seeking out partners who can offer cost-effective, customized leasing as an alternative to owning vehicles. Leasing brings benefits like reduced capital expenditure and predictable budgeting, which are especially attractive in uncertain economic times[50]. Winston witnesses this trend firsthand: many of his clients choose leasing because it frees up their capital and spares them the risk of asset ownership. Additionally, the push for sustainability and newer, greener vehicles plays to leasing’s strengths – a leasing company can cycle clients into the latest fuel-efficient or electric models more easily than a client managing owned older vehicles[51]. Relaxed Leasing is already positioned to help customers swap into new technologies as they become available, without the client carrying the burden of selling old units.
In terms of competition, Winston acknowledges that his company competes with large fleet leasing firms and local dealerships, but notes that Relaxed Leasing has carved out a unique niche. Few, if any, others offer the total package of any-vehicle sourcing, flexible terms, and lifecycle support with no inventory strings attached – certainly not in the Kansas City region, where Relaxed Leasing is “really the only one” with this model[52]. And while major players might have bigger fleets or nationwide branches, agility has been Relaxed Leasing’s edge. Winston started the company at perhaps the worst time – spring 2020, amid COVID-19 – yet that timing forced him to refine the business to be “extremely efficient, extremely cost-effective” from day one[53]. As the travel and hospitality industries rebounded, Relaxed Leasing was ready to scale up quickly by solving the urgent vehicle shortages (even navigating the microchip shortage that made new vans scarce)[54][53]. “It really set us up to be in a category that’s very unique – best product, best price,” Winston says of weathering those challenges[55]. Delivering top-notch vehicles fast, at rates comparable to or better than competitors, has surprised many clients and given Relaxed Leasing a reputation as a go-to problem solver.
Looking ahead, Matthew Winston sees sustainable growth on the horizon. Rather than chasing hyper expansion, he is focused on deepening relationships with the kinds of clients who value a partnership approach. “We’re not looking for anybody that isn’t in a good position and headed in the right direction,” he notes, explaining that vetting clients is as important to him as clients vetting his company[56][57]. By carefully onboarding organizations that are financially solid and operationally committed to using the leases effectively, Relaxed Leasing ensures it can meet their needs with the level of attention they expect. This strategy has led to zero client losses so far[34] and extremely high satisfaction. In the next 3–5 years, Winston plans to “continue down the same path”, expanding organically within existing client networks and taking on new business in smart, controlled steps[58]. Many hotels and hospital systems, for instance, are part of larger management groups – serving one property well often opens doors to others in the portfolio. Relaxed Leasing will continue leveraging those opportunities to grow its footprint, including beyond Kansas City. Already, the company is working with clients coast-to-coast, from Rhode Island to California (the company even registered to do business in numerous states to accommodate demand[59][60]). But Kansas City will remain its home base and a core market. “We intend to grow, but do it on a very smart trajectory,” Winston says, emphasizing that maintaining the quality of service is paramount as they scale[61].
It’s clear that Matthew Winston’s formula is working. By blending Kansas City hospitality with nationwide capability, Relaxed Leasing has become more than a leasing vendor – it’s a trusted partner that businesses know, like, and trust with their transportation needs[32]. In a competitive and operationally intensive sector, Winston’s approach of “best product, best price” delivered with a personal touch has set his company apart[55]. As one Kansas City Thrive interviewer put it, Relaxed Leasing is “making a footprint here in Kansas City” in a way that speaks volumes[62]. For local organizations and national clients alike, that footprint feels like a welcome path – one that leads to easier fleet solutions, guided by a steady partner who’s with them for the long ride. In the end, “relaxed” leasing might just become the new industry standard, thanks to an innovator from Kansas City who dared to do things differently.
Sources:
· Kansas City Thrive interview with Matthew Winston, Relaxed Leasing (2025)[52][19][28][35][15][32]
· Relaxed Leasing – Company Website and Materials[1][36]
· National Parking Association Convention Speaker Bio (2019)[63]
· Business Wire – Automotive Fleet Leasing Market Report (2024)[50][48]
[1] [23] Relaxed Leasing - Lease/Purchase/Rent Van/Shuttle/Bus
https://relaxedleasing.com/what-we-do/
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file://file_00000000705072309b0c0e45628620c1
[9] [10] [11] [63] Matthew Winston
[24] [25] Relaxed Leasing - Lease/Purchase/Rent Van/Shuttle/Bus
[36] [37] [38] Luxury Hotel Experience - Relaxed Leasing - Luxury House Cars
https://relaxedleasing.com/luxury-hotel-collection/
[47] [48] [49] [50] [51] Automotive Fleet Leasing Strategic Business Report 2024: Collaboration Between Leasing Companies and Automotive OEMs Strengthens Market - Global Forecast to 2030 - ResearchAndMarkets.com
https://business.sos.ri.gov/CORP_DRIVE1/2025/0324/000000000/8486/backup/202568120660_1.pdf
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