Category: About Us

👋 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.

  • Ward Work: Between Lawns, Speeches, and What’s Really Broken

    Ward Work: Between Lawns, Speeches, and What’s Really Broken

    Ward Work: Between Lawns, Speeches, and What’s Really Broken

    I went to a block club meeting yesterday—somewhere between Ward 11 and 12, at a neighbor’s house on West Boulevard. I got the invite through someone at the church community garden. I’ve been going to these for a while, staying plugged in. Yesterday was different. It was candidates’ night. The ones running for Cleveland City Council. Five of them, maybe six. One incumbent.

    I listened. That’s what I came to do. I listened to speeches. Polished. Practiced. Even eloquent. One candidate sounded like a politician from birth. Another talked about “trying to help one person per day”, but happy to help “one person a week”.

    Then came Nikki Hudson, who I have known since I bought my first home back in 2012, it was located on West 89th Street. A nice side by side double, that is where I met Nikki, I did not know she was going to be showing up today, but boy was I excited to see her there. I recalled how involved she had always been in these two wards over the years.

    But before we continue, let me say this clearly: I cannot be more appreciative of those who organized the event. This wasn’t some staged forum. It was a potluck. A real front-yard, block-club, folding-chair type of gathering. Sue Zimmerman opened up her space at 2094 West Blvd. That means something.

    These events give folks like me a closer look and a chance to get off the sidelines. But let’s be honest — I was invited last minute. Not by a campaign. Just someone I know through the church garden. I’ve lived here since 2012. I pay property taxes on more than one house. I employ locals. I’m involved. So why wasn’t I invited by the people running?

    That’s what bothers me. It’s the quiet part of politics that’s always loud to me. It’s not about representation — it’s about your representation. Your circle. Your flyer.

    It also does not escape me that this block club takes place on arguably the most affluent and historic street in the neighborhood—an irony that, by default, raises questions about the level of representation being achieved.

    Stomp speech quotes

    “I’m running for Cleveland City Council for the new Ward 11. I’ve lived on West 89th Street, North of Detroit with my husband and our two kids since 2002… And that is the type of energy that I intend to bring to the City Council. Thank you.”

    That speech, and others that night, they had the same rhythm. The same phrases. Community. Grassroots. Serving. or this one:

    “It’s not enough just to solve it for a bit. It’s important to solve that one issue for that person in Ward 11, but we should take the next step and try to solve them at scale…”

    So, finally it was time for Q&A. And one gentleman asked the question: Are you for gas station, for fire station, or neither. (Not sure about the third option from memory)?

    All candidates I believe had their shot at answering: for all the right reasons they were for the fire station. But why? That was essentially my long-winded question that must have come with way too much fire for the vibe. I asked anyways: Essentially I challenged the idea that there were only two choices. And why those two choices? It reminds me of George Carlin’s monologue; “you don’t have choices, you have the illusion of choices.”

    And as expected — but still saddening — what I got was not curiosity, or healthy debate, it was pushback; like justifying again why the fire station was a good thing, and how, blah blah blah. Versus… hey man… why do you think that… that’s so cool…

    Because what I heard felt like a Fox News interview. Like everyone read from the same thesaurus. There was no pain in the words. No weight. No mess. Where are the stories that live on these streets?

    This morning,

    I went on my walk. A mile and a half. Maybe two. That’s when it hit me. All of it. The speeches. The posturing. The safe answers. And I was thinking.. what exactly triggered me yesterday, because I was triggered, and it was when someone flipped a question back a me:

    “What are your ideas?”

    That triggered me. I don’t get triggered easy (not really true). But that did. What are my ideas? That’s the problem. I’m not running for office. You are. What are your ideas? Or better yet — what are the people’s ideas you claim to represent?

    If you say you are trying to help one person a day, I am sure people give you ideas when you are helping? Or who are you helping? Do they not live in this neighborhood? Or are we not listening.  The candidate who appeared to be great with his understanding of statistics, I will refer to as “Mr Statistician,” social worker, non profit professional; if the numbers from 311 are so rich in data, what information could you have provided us yesterday that we could easily implmenet in our own lives to make our existence a little bit better. Anything? What is the call to Action? If it is VOTE FOR ME, please miss me with that. That is too easy. I mean, the host Sue provided greater perspective and motivation than the candidates themselves. And the food was amazing too!

    But cool, do we want an idea? Lets do it!

    Grassroots Idea: want to help one person a day, I’ll call you on it. Let’s go. Let’s pick a block. From West 101st to 89th. Between Madison and Western. Let’s go knock. Ask if anyone needs their lawn cut, brushes trimmed, yard raked, whatever.   Something simple. But something real. I will provide the dumpster for whatever, maybe a 30 yarder! can we fill up a 30 yarder in 2 weeks, helping the ward prepare for winter! Yes, it is a challenge, but it is a doable one, and one that would allow all the candidates, including the new onesl; a chance to meet the voters that needs us the most. So; the challenge is on. Even if even one candidate accepts the challenge, my wife and I we will place a 20 to 30 yard dumpster in our backyard, so we can clean up Wards 11, and Wards 12 before fall. We got 14 days to fill that up. I am sure any of you will have a true chance to meet your candidates. Game on!

    And the one who helps the most? Not only you will most likely get my vote, I will open up my humble home to throw you a last minute vote for me thing. (if it is legal, I do not know what is legal or not). The potluck will have brazilian churrasco, mexican carne assada,  and probably some even more diverse stuff, as our neighbors will be called to participate.

    Long Term Plans?

    There was a lot of talking about long-term plans. Transit projects. Firehouse politics. But what about now? What about this week? Back to School Week. Like whats up

    One candidate dogged the 311 effort and its workers like that was the problem. Those folks are doing the job. If you know even one of the head operators and folks working on 311, you would know how much of a lift is to direct a whole city services through one phone call. But that is okay, let us go ahead and talk problems, and offer no solutions. Thanks, Sue for bringing us back on track on that one.

    As for grassroots? Tons of talk about grass roots

    Grassroots isn’t a press conference, and it’s not only a grant application. It’s showing up to clean a yard because someone can’t. It’s going to a church block party, even though you may be an atheist, —and that’s okay. It’s sending a volunteer who understands that reducing the campaign message to ‘vote for this candidate because he’s an immigrant’ does not reflect meaningful representation of any party. We can, and must, do better. Be intentional about earning local votes—our civic process deserves more than running shorts, New Balances, and a bandana. For many, you are the first real representative they’ll encounter in our democracy—and by extension, of the party you represent. I love informality as much as anyone, but don’t you want us to take you seriously? Wasn’t it said that each ward represents about 25,000 lives? Maybe pants and a collared shirt would have been a good start. I don’t know—it is 2025, after all.

    So when folks say they’re grassroots, I look at their shoes. If they’re clean, I move on.

    We from Wards 11 and 12 (by the way I pay taxes on both) we are yearning for imagination, we are eager for the return of “Yes we can”,  attitude and honestly, my true personal opinion, I would like to move to “yes we must, do better”.  The candidates for Wards 11 and 12, are in their majority experienced, well intentioned, and have the capacity to do an incredible job. My job as a citizen, is to challenge you all to be different and bolder. What is the alternative? Be yet someone else who was elected but nothing changed? So in two years we can hear the “I had to learn how to be realistic, the city is the problem, type of speech” I could go on and on… but these are my for the most part raw thoughts on the subject as they rused through my brain during my morning walk.

  • 💡 “Don’t wait ‘til you’re 55 and say, ‘I never did it.’”

    💡 “Don’t wait ‘til you’re 55 and say, ‘I never did it.’”

    Here’s a concise, punchy post built around your takeaways and anchored by your best quotes—centered on clarity, momentum, and bold action:

    💡 “Don’t wait ‘til you’re 55 and say, ‘I never did it.’”

    We’re not pitching a tour.

    We’re offering a live case study. A real one. With receipts.

    ✅ You’ll walk properties.

    ✅ You’ll meet operators and investors.

    ✅ You’ll see numbers.

    ✅ You’ll feel what it’s like to build something that actually cash flows.

    “You will get real case studies of housing that stays full. A network of people excited about real estate, about Brazil, about growth, about meeting new people and showing off what their city has to offer.”

    Whether you’re a digital nomad, an architect, or someone who keeps saying “I want to get into real estate” without ever doing it—this is your nudge.

    Brazil isn’t just vibes. It’s returns.

    “This is not for people who can’t stand the sight of me. This is for people who know me. If you know me, you know how I travel.”

    And if you come?

    You’ll travel the same way—with intention, access, and perspective.

    “I wouldn’t put it on a credit card and call it a vacation. I’d put it on a credit card and call it an investment.”

    Let’s go while the getting is good.


    🧭 October. StayWithJay. StudioHaus.

    📍 São Paulo and beyond.

  • 🇧🇷 Introducing Studio.Haus: Our Strategic Partner in Brazil

    🇧🇷 Introducing Studio.Haus: Our Strategic Partner in Brazil

    We’re thrilled to announce Studio.Haus as our official partner in Brazil — bringing StayWithJay’s proven hospitality model to one of the fastest-growing short-term rental markets in the world.

    Studio.Haus isn’t just another operator. Born from a bold vision to transform underutilized urban homes into high-performing boutique-style residences, Studio.Haus combines design, consistency, and operational excellence to meet the needs of modern travelers, digital nomads, and business professionals. Their model delivers fully furnished, branded units that feel like home — with the service and systems of a hotel.

    The SĂŁo Paulo-based team is led by Eric Cullenberg, co-founder of Studio.Haus and the architect of a growing network of turnkey hospitality assets across Brazil. With deep experience in real estate renovations, digital systems, and investor strategy, Studio.Haus is built from the ground up to scale.

    “Studio.Haus isn’t following the international template. We’re creating something clearly Brazilian, flexible, and welcoming — but backed by serious process.” — Eric Cullenberg

    Together, we’re already developing flagship locations in prime business districts — starting with Alvorada, near Faria Lima in São Paulo. And this is just the beginning.

    By combining StayWithJay’s global reach and investor community with Studio.Haus’s localized development expertise, we’re building a new kind of real estate platform: modular, profitable, replicable — and people-first.

    Expect more news soon, including updates on franchise sales, showroom tours, and new investment opportunities.

    📍 Explore Studio.Haus
    📬 Learn About the Franchise Opportunity