Category: About Us

đź‘‹ About Us

**Who is Jay?**

Better than tell you—let us *show you.*

StayWithJay was born from the grind, the hustle, and the vision of creating comfort where others see temporary stays.

🎙️ **The CEO’s Grind Podcast**
Tune in to the behind-the-scenes of what it really takes to build something lasting—our mindset, our moves, and the mission that drives every guest experience.

🎬 **Watch. Listen. Connect.**
Whether it’s real estate, entrepreneurship, design, or daily motivation—this is *Jay’s platform*, built to share his journey and talents with the world.

  • Power Restored, But the Questions Remain

    Power Restored, But the Questions Remain

    Power Restored, But the Questions Remain

    July 4, 2026 — 11:38 PM EDT

    Power has finally been restored for many Cleveland Public Power customers in the 44102 zip code.

    As an Airbnb operator, the financial impact of this outage was considerable. Reservations were disrupted, guests had to alter their plans, and countless hours were spent communicating, relocating, troubleshooting, and simply trying to help people through circumstances beyond anyone’s control.

    The economic loss, however, tells only part of the story.

    For more than twenty-four hours during the Independence Day holiday, thousands of residents, travelers, families, and businesses went without electricity. Convenience stores improvised to continue serving their neighborhoods. Restaurants adjusted operations. Property owners scrambled to protect food, equipment, and reservations. Guests and hosts alike experienced frustration, uncertainty, and discomfort.

    Today also happens to be the 250th anniversary of the American experiment.

    It is difficult not to reflect on that contrast. On one hand, we celebrate the resilience of a nation built on innovation and opportunity. On the other, an extended power outage affecting an entire community reminds us that maintaining critical infrastructure remains one of the most fundamental responsibilities of modern society.

    I am genuinely grateful that power has now been restored, and I appreciate the utility crews who worked to make that happen.

    At the same time, this experience should prompt thoughtful discussion about infrastructure resilience, emergency preparedness, and the systems communities depend upon every day.

    One final observation: despite some headlines describing the recent temperatures as unprecedented, summer heat waves are not new to Northeast Ohio. What made this event extraordinary was not simply the weather—it was the length of time that so many people were left without one of the most basic modern necessities.

    Tonight, the lights are back on.

    For everyone affected, that is welcome news.

    Excerpt

    Power has been restored to much of Cleveland’s 44102 zip code after more than twenty-four hours without electricity. A reflection on the impact the outage had on guests, hosts, businesses, and the importance of resilient infrastructure.

    SEO Title

    Power Restored After Cleveland’s July 4 Outage | Reflections from a Local Airbnb Host

    Meta Description

    After more than 24 hours without electricity, power has been restored to Cleveland Public Power customers in the 44102 area. A local Airbnb operator reflects on the outage’s impact on guests, businesses, and infrastructure.

  • Why Do People Who Need Money the Most Often Make the Most Ex

    Why Do People Who Need Money the Most Often Make the Most Ex

    Why Do People Who Need Money the Most Often Make the Most Expensive Decisions?

    Observations from more than 10,000 Airbnb nights per year.

    Over the better part of a decade, I’ve operated affordable accommodations in Cleveland.

    During that time, our company has hosted tens of thousands of reservation nights. More importantly, we’ve welcomed thousands of unique guests.

    This isn’t an academic study.

    It’s a front-row seat to how ordinary people live.

    More than 63% of our guests tell us they chose Stay With Jay for one simple reason:

    We were the most affordable option.

    That matters because affordability isn’t just our marketing strategy—it’s our operating philosophy.

    We intentionally try to keep our guests’ total housing costs low.

    A one- or two-night stay often works out to under $60 per night.

    Longer weekly stays approach $50 per night.

    Monthly stays can fall to approximately $45 per night.

    Those prices include utilities, Wi-Fi, parking, laundry, and weekly room turns. We try to eliminate the hidden expenses that quietly make life more expensive.

    Yet something fascinating happens after guests arrive.

    The Paradox

    Many guests work hard to save $10 choosing an affordable room.

    Then spend $30 on Uber.

    Twice.

    Sometimes three times.

    The next morning, instead of cooking in a fully equipped kitchen, breakfast arrives through DoorDash.

    Lunch comes through Uber Eats.

    Dinner follows.

    None of these choices, by themselves, are irrational.

    I use Uber.

    I order delivery.

    Most people do.

    The difference is frequency.

    When transportation costs exceed housing costs…

    when convenience becomes a daily habit…

    small decisions become expensive lifestyles.

    The Popcorn Guest

    One pattern appears again and again.

    Internally, I call them “popcorn guests.”

    They bounce from one reservation to another.

    One night here.

    Two nights there.

    Another booking somewhere else.

    Then back again.

    Some have accumulated more than 200 nights with us over several years.

    One guest had over 40 check-ins and check-outs in just ninety days.

    That isn’t unusual in affordable housing.

    What fascinates me isn’t the number of stays.

    It’s the consistency of the surrounding decisions.

    The Math Doesn’t Care

    Suppose transportation averages $30 per day.

    Housing averages $53.

    Before food, before clothing, before your phone bill…

    life already costs $83 every day.

    Round that to roughly $100 after taxes and income requirements.

    That’s approximately $3,000 per month before eating.

    Now add restaurant meals because the kitchen sits unused.

    The financial picture changes dramatically.

    Again…

    None of these decisions are individually catastrophic.

    Together, they become a system.

    This Isn’t About Blame

    It’s easy to say,

    “They should just cook.”

    “They should ride the bus.”

    “They should budget better.”

    Reality is rarely that simple.

    Time.

    Stress.

    Mental bandwidth.

    Transportation.

    Neighborhood safety.

    Work schedules.

    Childcare.

    Energy after a twelve-hour shift.

    All influence decision making.

    Understanding behavior is far more valuable than judging it.

    What If Hospitality Could Help?

    This question has become increasingly important to me—not just as a host, but as a business owner.

    If we understand these patterns…

    could we design an environment that naturally leads to better outcomes?

    Not by forcing behavior.

    By reducing friction.

    Perhaps the answer isn’t cheaper rooms.

    Perhaps it’s helping guests use the kitchens more often.

    Maybe it’s highlighting nearby grocery stores the day before check-in.

    Maybe it’s surfacing bus routes inside the guest portal.

    Maybe it’s sending targeted promotions based on length of stay.

    Maybe it’s helping repeat guests consolidate bookings instead of constantly moving.

    Maybe it’s introducing referral programs or loyalty rewards that reinforce financially healthy behaviors.

    The point isn’t to tell people how to live.

    The point is to design hospitality that makes the better choice the easier choice.

    Subscription Behavior Without a Subscription

    Here’s another observation.

    Stay With Jay is not a subscription business.

    Yet roughly 60% of our revenue comes from guests who behave like subscribers.

    They return.

    Again.

    And again.

    And again.

    Every reservation is another vote of confidence.

    They trust us enough to sleep under our roof.

    That trust is incredibly valuable.

    It also creates an opportunity.

    Not simply to earn another reservation.

    But to improve the guest’s experience beyond the room itself.

    Keep More Per Stay. Earn More Per Stay.

    The lesson isn’t that poor people make poor decisions.

    The lesson is that everyone makes decisions within the environment they’re given.

    If we can design that environment better…

    our guests may keep more of what they earn.

    And if our guests keep more…

    they’re more likely to return.

    That creates a rare outcome where everyone’s interests align.

    Guests build greater financial stability.

    We build a stronger business.

    Communities become healthier.

    Sometimes the best hospitality isn’t a nicer room.

    It’s helping someone leave with a little more money than they would have otherwise.

    Keep More Per Stay. Earn More Per Stay.

  • Mission

    Mission

    Our Mission

    At StayWithJay, we are leading a humble but powerful transformation—reshaping ordinary urban homes into vibrant, respectful residential communities. Here, homeowners and investors collaborate to create value in both the short- and long-term rental markets.

    But this isn’t just about housing. It’s about supporting the people who keep our economy moving:

    • Traveling nurses
    • Up and coming artists
    • Startups
    • Consultants
    • Doctoral students
    • Remote tech workers
    • And others in the growing gig and commuter economy

    These professionals are often underserved and overcharged by traditional hotels and short-term rentals. We exist to change that—one check-in at a time.

  • The Bermuda Triangle of Small Biz: When Growth Kills Control

    The Bermuda Triangle of Small Biz: When Growth Kills Control

    When your remodeling crew outgrows your control — what happens next?
    Wesley got back on the truck and what he found forced a major reset.

    This episode is a brutally honest breakdown of what goes wrong when expectations aren’t set, when hours aren’t tracked, and when foremen (and apprentices) operate without a clear plan.
    Jay and Wes walk through the accountability chain — from the field, to the foreman, to the office — and how to put it back in place before the business bleeds out.


    đź§± Topics Covered:
    — What Wesley found when he shadowed his own crew
    — The missing “hours allowed” problem
    — Why job costing must start on paper
    — How to fix remodeling ops before they crash
    — Holding your team (and yourself) accountable


    đź’ˇ Key Quote:
    “If your team doesn’t know what’s expected, how can you hold them to it?”


    🎯 For:

    • Small business owners scaling too fast
    • Contractors, tradesmen, remodelers
    • Operations managers in the field
    • Anyone trying to fix a money-leaking team

    🎙 More CEO’s Grind:
    https://ceosgrind.com
    đź’Ľ Strategy Support: https://catalystwin.com
    🔧 Wes’s Company: https://buildingwaters.com


    #RemodelingBusiness #CEOGrind #TradesLeadership #Accountability #ServiceFusion #BuildingWaters #FieldOps #SmallBusinessFix #ConstructionLife #PodcastDrop