Cleveland by Jay

Category: Own Your Airbnb in Brazil – we are betting big in Brazil

An investment trip to Brazil curated by Stay with Jay and our Brazilian franchise, Studio.haus

  • CEOs Grind Updated Itinerary

    CEOs Grind Updated Itinerary

    🇺🇸

    Welcome to Brazil — StudioHaus Experience Day 1

    We’re thrilled to welcome Wesley to Brazil for the first leg of our investment and discovery journey with StudioHaus.

    ✈️ Arrival:

    Wesley will arrive on Sunday, October 26th, 2025, from Chicago via United Airlines.

    Jay Silva and our driver will be waiting at Guarulhos International Airport (São Paulo) to greet him and start the day together. Arrival time: 7:15AM

    ☕ Morning — Welcome Brunch

    Our first stop will be a light and relaxing brunch at Mostardas, in the charming town of Monte Alegre do Sul, São Paulo — the perfect place to begin the week on a high note.

    🕚 Time: 11:00 AM

    🏡 Check-In — Home Away from Home

    After brunch, we’ll check in at Wesley’s Airbnb:

    📍 Rua Hermelindo Rodrigues Bueno, 3797 — Monte Alegre do Sul, São Paulo 13910-000

    🍽️ Lunch at Dom Bambu

    At 12:30 PM, we’ll have lunch at Dom Bambu Restaurant, where a special menu has been thoughtfully arranged by Heloisa — an atelier, former executive at Grupo Pão de Açúcar, former university professor at Universidade Paulista, and advisor to Jay Silva and his enterprises.

    Heloisa, a long-time friend, kindly coordinated this lunch with Augusto, Dom Bambu’s owner, to make our first day in Brazil feel like home.

    The afternoon will be open for rest and exploration — with the beautiful countryside of Monte Alegre do Sul setting the tone for what’s ahead.

    Welcome to Brazil, Wesley. The journey begins now. 🌿

    Stay in the Grind.

    🇧🇷

    Bem-vindo ao Brasil — Experiência StudioHaus, Dia 1

    Estamos muito felizes em receber o Wesley no Brasil para a primeira etapa da nossa jornada de investimento e descoberta com a StudioHaus.

    ✈️ Chegada:

    Wesley chega no domingo, 26 de outubro de 2025, vindo de Chicago pela United Airlines.

    Jay Silva e nosso motorista estarão esperando no Aeroporto Internacional de Guarulhos (São Paulo) para recebê-lo e iniciar o dia juntos.

    ☕ Manhã — Cafeizin de Boas-Vindas

    Nossa primeira parada será um brunch leve e acolhedor no Mostardas, na charmosa cidade de Monte Alegre do Sul (São Paulo) — o lugar perfeito para começar a semana com boas energias.

    🕚 Horário: 11h00

    🏡 Check-In — Seu Lar Temporário

    Após o brunch, faremos o check-in no Airbnb do Wesley:

    📍 Rua Hermelindo Rodrigues Bueno, 3797 — Monte Alegre do Sul, São Paulo 13910-000

    🍽️ Almoço no Dom Bambu

    Às 12h30, teremos almoço no Restaurante Dom Bambu, com um menu especialmente preparado por Heloisa — atelier, ex-executiva do Grupo Pão de Açúcar, ex-professora universitária na Universidade Paulista e conselheira de Jay Silva e suas empresas.

    Heloisa, gentilmente organizou este almoço em parceria com Augusto, proprietário do Dom Bambu, para que nosso primeiro dia no Brasil seja recebido com carinho e hospitalidade.

    A tarde será livre para descanso e exploração — o interior de Monte Alegre do Sul será o cenário perfeito para iniciar nossa jornada.

    Bem-vindo ao Brasil, Wesley. A jornada começa agora. 🌿

    Stay in the Grind.

  • From Aracoiaba to Monte Alegre do Sul

    From Aracoiaba to Monte Alegre do Sul

    https://maps.app.goo.gl/4wcoVLgE73cRCNeg7

  • Back in São Paulo

    Back in São Paulo

    Back in São Paulo

    The last time I was here was November of ’24 — not much has changed since then, I can’t lie.

    I decided not to book anything in advance this time. I wanted to wait until I was on the ground, in the neighborhood I actually wanted to stay in. After a bit of searching, I sent a request to one Airbnb host and didn’t hear back for over 30 minutes. So I sent another request — this time to Michelle.

    Her response was quick, thoughtful, and clear. She offered me an early check-in at 1 PM, no extra charge, no hassle. The best part? My total for the first two nights came to less than $90.

    The flat is inside the World Hotel, where the front desk even offers free luggage drop-off. Across the street, there’s the classic São Paulo combo — a bakery and a bar. I waited there about an hour while my room was being prepped. Michelle messaged me right at 12:50 PM to let me know it was ready.

    The Wi-Fi at the bakery was solid, so I didn’t even need to touch my data plan. Check-in was smooth — the staff spoke fluent English and Spanish, from what I could hear helping other guests.

    MyViewfromtheroom

     

    Finally made it to my studio — one bedroom, cozy setup, not sure about the square footage yet (I’ll update that later). For now, time to unwind… maybe an evening walk through Ibirapuera Park.

    Stay in the Grind.

     

  • Studio Haus Itinerary Full

    Studio Haus Itinerary Full

    Brazil Trip Accommodations : 

     

    We recommend staying at the Pullman Vila Olimpia, which is a business hotel run by Accor, an international brand. The location provides many options within walking distance.

     

    From Sunday, October 26th – Friday October 31st. 

     

    https://all.accor.com/hotel/8938/index.en.shtml

     

    The expected price should be around USD 2.000 

     

    A more high-end option would be the new W hotel which is by Marriot. Its located on a small street about 500 m from the Pullman.   (Any other hotel you might want to choose is fine it just should be close to “Shopping Vila Olimpia” as a reference point, if possible.) 

     

    https://www.marriott.com/en-us/hotels/saowh-w-sao-paulo/overview/

     

    The expected price looks to be around USD 3.500

     

    I would recommend the rate that include breakfast and has flexible cancellation in case there is some change (Rather than non-refundable without breakfast) 

     

    From Friday October 31st – November 3rd 

     

    My friend has a bed & breakfast in Caraguatuba approximately 3 hours from São Paulo by car. This would be a nice place for us to be and relax and ge to know this market. We can have breakfast and BBQ´s there and the cost will be reasonable at $150 night x 3.

     

    We can make reservations and pay for the rooms on your behalf.. 

     

    https://buy.stripe.com/8x2eVccbA1yYa7A18W9sk0c