The Legit Real Estate Podcast

From last-minute closings to wild inspection surprises — this episode of The Legit Real Estate Podcast gets real about the unpredictable world of buying and selling homes in Rhode Island, Connecticut, and Massachusetts. TJ Ciolfi and Holly Regoli share the craziest stories from the field — the wins, the close calls, and the lessons that every buyer, seller, and agent should know. Whether you’re a...

Ever found ashes in a closet during a showing? Or watched a seller drive through their garage door before closing? In this hilarious and jaw-dropping episode of the Legit Real Estate Podcast, TJ, Holly, and guest Deb Gianini share unbelievable real estate war stories — from spooky Providence listings to clients moving out at the last minute. Deb also opens up about mentorship, confidence in real e...

In Episode 33 of The Legit Real Estate Podcast, TJ and Holly Regoli kick things off in an unconventional way — with TJ joining the show while driving 80 mph to his next meeting! Between laughs and safety debates (seatbelts included!), the duo dives into stories from the road, lessons from the real estate trenches, and what it really takes to stay productive when life gets hectic. Listen the conver...

Scams in real estate are more common than many people realize—and they’re getting more sophisticated. In this episode, we dive straight into the different types of frauds and traps that buyers, sellers, and even agents need to be aware of.- Fake buyer emails and scam inquiries- How scammers impersonate names like “Julia Sydney” to trick agents- Home title theft and why it’s a growing concern- Red...

Owning real estate isn’t always glamorous — sometimes it means walking into your basement to find a river running through your property. In this episode of the Legit Real Estate Podcast, host TJ Ciolfi and Holly Regoli share a behind-the-scenes look at a chaotic day:- Walking into a rental property flooded basement - Emergency fixes with sump pumps, PVC pipes, duct tape & quick thinking- Lesso...

In this episode of The Legit Real Estate Podcast, the hosts start with a real open-house scare that reshapes how agents should handle events—then pivot to how newer credit-scoring approaches that factor on-time rent & utilitie payments may help more renters qualify for a mortgage. No fluff, just real-world lessons you can use. Highlights:- Open-house safety, real story: A rural property, an af...

In this episode, Holly Rogoli sits down with John Casmon former corporate marketer turned multifamily investor, to reveal how he made the leap from flipping houses to building a portfolio with over 100 investors. John breaks down the real difference between active and passive investing, and the tax and estate benefits of using syndications. You’ll learn:Why flips can be stressful Overview of how s...

Welcome to another episode of The Legit Real Estate Podcast with T.J Ciolfi and Holly Regoli — where real estate meets real life. 🎯 In this episode: What it’s really like to show up to the office during a hectic week Hilarious moments and wardrobe fails in the middle of deals 👕 A look into how real estate agents juggle client demands, paperwork, and personal sanity Building trust with buyers and...

Welcome to another episode of the Legit Real Estate Podcast with your hosts TJ Joe and Holly Rgoly ! In this episode, we go beyond the closing table and into the real lives of real estate pros in Rhode Island, Connecticut, and Massachusetts . From camping in the rain to serving meals at the Special Olympics, Holly shares what it means to give back to the community—while still juggling a busy real...

Special Guest: Dana Pizzarelli In this lively and candid episode of The Legit Real Estate Podcast , hosts TJ Chofi and Holly Regoli sit down with Dana Pizzarelli , a real estate expert known for keeping things real—cats and all! 🐾 🔑 Episode Highlights: Dana’s real-world experiences in real estate and the challenges of balancing work and life. Insightful discussion on navigating today's compe...

Ever wonder what real estate agents do when they’re not showing homes? In this clip from The Legit Real Estate Podcast , Holly shares a hilariously relatable Friday — paperwork, parenting duties, yard work regrets, and even forgetting the podcast schedule! A real look at how realtors balance business and life.

In this gripping episode of The Legit Real Estate Podcast , TJ and Holly dive into the real-life dangers that real estate professionals face—from walking into unfamiliar homes alone to encountering unpredictable clients. This isn’t just about property—it's about personal safety, awareness, and setting boundaries in a high-risk profession. If you're a realtor, aspiring agent, or someone who...

This week on The Legit Real Estate Podcast , TJ Chofi and Holly Regoli tackle the surprising ways solar panels can complicate a home sale. From sky-high monthly payments to misunderstood contracts, they share real stories from the field—and their own lives—that reveal what every buyer, seller, and agent should know. 💡 Topics include: • How solar leases and liens affect closing • TJ’s personal exp...

In this episode of the Legit Real Estate Podcast, TJ Chopin and Holly Ragoli kick things off with Crazy Hat Day shenanigans—but don’t worry, they quickly dive into the real issues.🎯 Episode 19 Highlights:Holly shares her struggle with a nightmare rental vacancy and the hard truth about dealing with difficult tenants. The duo discuss the pros and cons of being a landlord—especially when your renta...

In this episode of the Legit Real Estate Podcast, hosts TJ Ciolfi and Holly Regoli welcome Bubba Correira from Lapointe Insurance to break down everything real estate agents and homeowners need to know about insurance—in plain English.🏡 From funny client stories to real-life lessons, you’ll learn:What insurance coverage people often overlookWhy the right insurance partner can save a dealHow to ex...

Oh we found some funny Real Estate related Am I the Assholes! And we want to share!

Holly and TJ share some crazy real estate stories they found on Reddit

Ugh sometimes sellers really don't want to listen to our advice. What do you do when a seller wants to list they house higher than what you recommend? Please don't mind Holly's audio on this episode. Her new camera audio turned out to be horrible.

Holly and TJ Talk to Kenny Tessitore from Loan Depot about some of the crazy stories he's come across in the lending world (including a morgue scandal). #thelegitrealestatepodcast #tjciolfirealtor #realestate #realestateinvesting #hollyregolirealtor Here's Kenny's contact info if anyone wants to reach him: Kenneth TessitoreNMLS# 2416591Loan Consultant (508) 850-4043 office(508) 733-076...

TJ and Holy talk about some pretty devastating vermin including a weasel encounter that nearly eradicated Holly's flock of chickens.

Holly found some cool real estate stories online and wants to share them with you.

"House with eater view"..."Must see inside". Holly and TJ talk about the meanings behind real estate descriptions.

We have our first guest on the show! Join us and our special guest Elyse Gesmondi as she shares some of her funny real estate stories, like the time she found a leg at a house or that time her clients could not wait for her to leave before getting it on. Ah, the fun world of real estate. Join us for some laughs.

Hate to say it, but sometimes tenants can really suck! Today, Holly and Tj will talk about some crazy experiences with tenants!

Holly and TJ talk about some if the things they've encountered in commercial property settings.