Episode 7: Beyond the Buzzwords: Ty Shehadi on Optimizing Restaurant Tech for Single-Unit Operators
Guest: Ty Shehadi, Head of Strategic Partnerships at Restaurant365
Episode: 86 Reason Ep. 7 | Ty Shehadi (Restaurant365): Why Single-Unit Operators Need More Than Just Software
Episode Duration: 1hr 10m 45s
Published: November 10, 2025
Topics: Restaurant Technology, Single-Unit Operations, Strategic Partnerships, Back-Office Support, Restaurant365, Employee Training
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Episode Summary
In the fast-paced world of hospitality, technology promises to streamline operations and boost profits. Yet for many single-unit restaurant operators, the reality of implementing powerful back-office tech solutions often falls short of expectations. They invest in cutting-edge platforms, but the challenge of fully integrating and maximizing these tools can feel overwhelming.
In this insightful episode of 86 Reason, host Xavier Mariezcurrena sits down with Ty Shehadi, Head of Strategic Partnerships at Restaurant365, to pull back the curtain on this critical issue. Ty, whose career spans from busboy to restaurant tech leader, shares his unique perspective on why even the best technology needs a human touch to truly thrive in the independent restaurant space.
His message is clear: optimizing restaurant tech for single-unit operators isn't just about software, it's about pairing powerful tools with the support services that make them actually usable for time-strapped operators.
Key Takeaways
The "Ownership Mindset" Forged on the Front Lines
Ty's journey began around age 10 or 11 as a busboy in a mom-and-pop restaurant, quickly moving up to "official omelet maker." This early experience, combined with a "poor upbringing" that instilled a drive to "go out and get it," shaped an inherent ownership mindset.
After graduating with a finance degree during the Great Recession, Ty found himself drawn back to restaurant management, eventually spending 11 or 12 years "within the four walls." This deep operational experience is what he now brings to the tech world, understanding the bootstrap mindset required to build a "business within a business" even within a large organization.
The Overlooked Struggle of Single-Unit Tech Adoption
While enterprise restaurant groups benefit immensely from comprehensive solutions like Restaurant365, Ty highlights a critical nuance for single-unit operators. He candidly admits that Restaurant365 is often not a suitable fit for many single-unit operators unless paired with support services.
These operators simply "lack the time and means to maximize its use" because they are "doing 12 different things" every day. Without dedicated resources, even the most robust tool can become another layer of complexity rather than a solution.
Technology Must Be Packaged with Support
Ty's key insight is transformative: for single-unit operators, technology must be "packaged with a service, somebody to support them." This ensures that tools are set up correctly, utilized efficiently, and truly deliver on their promise of cost optimization and back-office efficiency.
This directly resonates with Over Easy Office's mission to provide essential outsourced bookkeeping, AP processing, and inventory management services that empower restaurants to leverage their tech stack without being overwhelmed.
Hospitality as Life's Training Ground
Beyond numbers and strategies, Ty and Xavier discuss the profound impact of working in hospitality. Ty asserts:
"I think here we should make people work in the hospitality industry before they go into a real job."
He emphasizes that the industry teaches invaluable life skills such as conflict resolution, how to talk to people of different backgrounds and experiences, and robust accountability where "everything's visible." This foundational experience builds unique resilience and understanding of human connection vital for any professional path.
Strategic Partnerships as Growth Catalysts
Ty's career in restaurant technology, particularly his role in Expanshare (later acquired by Restaurant365), showcases the power of strategic partnerships. He spearheaded a pivotal 14-15 month deal with US Foods, adapting Expanshare's custom training content into a scalable SaaS product.
This partnership was a "game changer," propelling Expanshare to become a top partner and demonstrating how collaborations can fill critical gaps in a larger company's offerings, such as R365's need for employee training solutions.
Meet Our Guest: Ty Shehadi
Ty Shehadi
Ty Shehadi is the Head of Strategic Partnerships at Restaurant365, the leading back-of-house accounting, inventory, workforce management, and payroll solution specifically for the restaurant industry. With over 15 years of experience spanning from busboy and restaurant manager to sales leadership and tech partnerships, Ty brings a unique ownership mindset to solving the industry's most complex challenges.
He's also a partner at Whistle Taproom in Cleveland and has built and led successful partner programs for brands like ChowNow, SevenRooms, and Expanshare, working with industry giants like US Foods and Square.
Connect with Ty:
LinkedIn: in/tshehadi/
Website: www.restaurant365.com
Company: Restaurant 365
The Story: From Busboy to Tech Leader
The Early Start
Ty's restaurant journey began remarkably young—around age 10 or 11 as a busboy in a mom-and-pop restaurant. This wasn't a summer job or casual work; it was formative exposure to the hospitality industry's demands, rhythms, and rewards at an impressionable age.
He quickly progressed to "official omelet maker," a role that taught him not just cooking skills but the accountability and pressure of being responsible for a specific station. When customers order omelets, they're watching you make them—there's nowhere to hide from mistakes or subpar performance.
The Ownership Mindset Origins
Ty credits his "poor upbringing" with instilling a drive to "go out and get it"—a hunger to create opportunities rather than wait for them. This mentality, combined with early restaurant experience, forged what he calls an "ownership mindset."
This mindset isn't about ego or control; it's about taking personal responsibility for outcomes, finding creative solutions to problems, and building something valuable even when resources are limited. It's the bootstrap mentality that characterizes successful entrepreneurs across industries.
The Great Recession Pivot
Ty graduated with a finance degree during the Great Recession—arguably the worst possible timing for launching a traditional finance career. Like many in his cohort, he found limited opportunities in his intended field.
Rather than viewing this as failure, Ty leaned into what he knew: restaurants. He spent 11 or 12 years "within the four walls," gaining deep operational experience that would prove invaluable when he eventually transitioned to restaurant technology.
The Bridge to Technology
Ty's move from operations to technology wasn't abandonment of restaurants—it was an evolution. He recognized that his operational expertise gave him unique insight into what operators actually need versus what tech companies think they need.
This operational credibility is what makes Ty effective in his role at Restaurant365. He's not a tech person trying to understand restaurants; he's a restaurant person leveraging technology to solve real problems he's personally experienced.
Key Insights: The Single-Unit Reality
Why Powerful Software Isn't Always the Answer
One of Ty's most important contributions to the conversation is his honest assessment of Restaurant365's limitations for certain operators. Despite working for R365, he candidly acknowledges that the platform isn't always the right fit for single-unit operators—unless paired with support services.
This honesty is rare in technology sales, where the tendency is to position your solution as universally applicable. Ty's willingness to acknowledge limitations builds credibility and trust.
The Time and Resource Challenge
Single-unit operators face a unique challenge: they're doing 12 different things every day. They're the HR department, marketing team, maintenance crew, and financial analyst—all while trying to ensure guests have great experiences.
Asking these operators to also become Restaurant365 experts—learning the platform's extensive capabilities, maintaining data quality, generating and interpreting reports—is often unrealistic. The time simply doesn't exist, regardless of the software's quality.
When Good Tools Become Burdens
Without adequate support, even excellent technology can become another burden rather than a solution. The software sits underutilized, data quality degrades, and promised benefits never materialize. The operator is left frustrated, having invested money in a tool that's actually making their life harder.
This is the dirty secret of restaurant technology: adoption and utilization matter far more than features and capabilities. A simpler tool that's actually used consistently beats a sophisticated platform that sits idle.
The Power of Paired Services
Technology Plus Human Support
Ty's prescription for single-unit operators is straightforward: technology must be "packaged with a service, somebody to support them." This human element ensures:
Proper initial setup that captures the operator's specific needs
Ongoing data quality management so reports are accurate and useful
Regular review and interpretation of financial insights
Troubleshooting support when issues arise
Continuous optimization as the business evolves
This paired approach transforms technology from a burden into a genuine asset.
The Over Easy Office Connection
Ty's insight directly validates Over Easy Office's business model. By providing outsourced bookkeeping, AP processing, and inventory management services, OEO enables restaurants to leverage sophisticated platforms like R365 without requiring operators to become experts themselves.
This partnership model—powerful technology plus specialized human support—represents the future of restaurant back-office operations, particularly for single and small multi-unit operators.
Making the ROI Real
The return on investment from restaurant technology only materializes when the tools are actually used properly. A $500/month software subscription that sits underutilized represents $6,000 in annual waste. That same subscription paired with $1,500/month in support services that enables full utilization can deliver $50,000+ in annual value through better cost control, improved decision-making, and operational efficiency.
The math favors paying for support that ensures technology delivers on its promise.
Hospitality as Universal Training
The Skills Everyone Should Learn
Ty's assertion that everyone should work in hospitality before entering their "real job" reflects deep insight into what the industry teaches. Restaurant work develops:
Conflict resolution - Handling upset customers, mediating team disputes, and finding solutions under pressure
Cross-cultural communication - Working with people from diverse backgrounds and life experiences
Visible accountability - In restaurants, your performance is immediately obvious to everyone
Stress management - Operating effectively during intense rushes and high-pressure situations
Team coordination - Synchronizing efforts with others toward common goals
Customer empathy - Understanding and responding to human needs and emotions
These are foundational life skills applicable far beyond restaurants.
Everything Is Visible
One of Ty's most powerful observations is that in restaurants, "everything's visible." When you make a mistake, everyone sees it immediately. When you excel, that's equally apparent. This creates a level of accountability rare in other industries.
Office jobs often allow people to hide mediocre performance behind closed doors, spreadsheets, and meetings. Restaurants don't offer that luxury. This intense transparency builds character and work ethic.
The Human Connection Foundation
Restaurant work is fundamentally about human connection—understanding what people need, responding with care, and creating positive experiences. This human-centered approach is valuable in any career path, from technology to finance to healthcare.
Ty's own career trajectory demonstrates this. His success in restaurant technology partnerships comes from genuinely understanding and caring about operator challenges, not just technical specifications.
Strategic Partnerships: The Expanshare Story
Identifying the Opportunity
Ty's pivotal 14-15 month deal with US Foods while at Expanshare demonstrates strategic partnership execution at its best. He identified a critical gap: US Foods customers needed employee training solutions, and Expanshare had the content and expertise to provide them.
This wasn't just a sales opportunity—it was a genuine match between a supplier's capabilities and a large company's customer needs.
The Transformation Challenge
Expanshare's existing product was custom training content—highly tailored but not scalable. The US Foods partnership required transforming this into a SaaS product that could serve thousands of customers without custom development for each one.
This transformation demanded significant investment, risk-taking, and adaptability. Many companies would have stuck with their existing model rather than making the leap required for the partnership.
The Game-Changing Results
The partnership proved to be a "game changer," propelling Expanshare to become a top partner and significantly accelerating growth. This success ultimately contributed to Restaurant365's decision to acquire Expanshare, recognizing the value of integrated employee training capabilities within their comprehensive platform.
The story illustrates how strategic partnerships can create exponential growth opportunities when they fill genuine market needs and align incentives properly.
Lessons for Restaurant Operators
The Expanshare-US Foods partnership offers lessons for restaurant operators:
Identify complementary strengths between your capabilities and potential partners
Be willing to adapt your offering to serve partnership opportunities
Focus on solving real problems rather than just pursuing revenue
Build relationships that create mutual value rather than one-sided extraction
The Personal Ingredient
Still in the Trenches
Ty isn't just talking about restaurants from a distance—he's a partner at Whistle Taproom in Cleveland. This ongoing operational involvement keeps him grounded in the realities operators face daily.
This dual perspective—technology leader by day, restaurant operator always—makes his insights more credible and nuanced. He's solving problems he personally experiences.
The Bootstrap Philosophy
Ty's concept of building a "business within a business" even within a large organization reflects his bootstrap origins. He approaches his role at Restaurant365 with entrepreneurial energy, treating his partnership function as its own venture rather than just a corporate job.
This mindset creates innovation and drive that benefits both R365 and the partners and customers he serves.
Actionable Insights for Restaurant Operators
What You Can Apply Today
Honestly Assess Your Technology Capacity - Do you realistically have time to master and maintain your current tech stack? If not, explore support services that can bridge the gap rather than continuing to struggle.
Prioritize Paired Solutions - When evaluating new technology, ask about support services. Optimizing restaurant tech for single-unit operators requires human expertise alongside software capabilities.
Calculate True ROI - Consider both the software cost and the time required to use it effectively. Often, paying for professional support delivers better ROI than trying to DIY complex systems.
Leverage Your Hospitality Skills - If you've worked in restaurants, recognize the valuable skills you developed. Conflict resolution, visible accountability, and human connection transfer to every aspect of business.
Seek Strategic Partnerships - Look for complementary businesses where collaboration creates mutual value. The best partnerships solve real problems for both parties' customers.
Build an Ownership Mindset - Approach challenges with the mentality of creating solutions rather than waiting for them. This entrepreneurial perspective applies whether you're an operator or working within someone else's organization.
Share Your Thoughts
Have you struggled to fully utilize restaurant technology due to time constraints? What support services would make the biggest difference in your operations? Connect with us and share your experiences.
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Ready to pair your restaurant technology with the human support it needs to deliver real value? Learn how Over Easy Office's outsourced bookkeeping, AP processing, and inventory management services can help you maximize your tech investments without the overwhelm. Contact us today to discover solutions tailored for single and multi-unit restaurant operators.