From Wine Marketing to Real Estate Empire: A Conversation with Josh Baldovino

In the latest episode of the Hospitable Hosts podcast, we welcome Josh Baldovino, a real estate investor who juggles multiple roles with remarkable success. He's a Marketing Manager for a California winery by day, but his entrepreneurial spirit doesn't stop there.
Josh runs his marketing agency and is a partner at NVST Capital, a real estate investment firm specializing in helping individuals achieve passive income through commercial multifamily apartment investments. He also manages an impressive real estate portfolio, including a 111-unit apartment complex, eight long-term rentals, and four short-term rentals in Columbus, Ohio.
In this episode, Josh shares his insights on balancing a busy schedule, maximizing ROI, and leveraging marketing expertise to thrive in the competitive world of real estate investing.
Press Play now to find the most profitable real estate investing strategies and get valuable advice for real estate investors looking to enter the market.
If you prefer to read the highlights, we've got a summary of the key takeaways below.
Real Investment Strategies That Yield the Highest ROI
At the beginning of the conversation, Josh shares his journey into becoming a real estate investor and gives the listeners a scope of his portfolio. They started real estate investing five years ago and acquired properties through various strategies. So now they have eight long-term rentals, own two STR/ MTRs, and manage four more. They also participated as co-GPs in acquiring a couple of commercial properties—an apartment in Dallas and an assisted living facility in Fresno, California.
Discussing which strategy has been the most profitable for him and yielded the best ROI, Josh points out that they all work. "If you think of it from an equity standpoint, the BRRRR deals are the best because that's almost 100% return on your money because you get all your money back out. However, with the STR play, we also get the best tax write-offs, which means we did one of the crazy cost segregation/ bonus depreciation plays. It's very different now than it was 4 years ago when I did it. But you've got close to $100,000 in tax write-offs. So besides it being profitable and getting that, it varies."
Methods That Help Stay Organized
Josh emphasizes that since he has a full-time job and does some marketing consulting on the side, a partnership is the right structure for him in the real estate investment business. "It's either partnerships or you build out a team to help with some of the asset management that either I'm not great at or don't want to do," he explains.
They also hired a property management company to manage their portfolio of long-term rentals, which generates passive income. However, "you still have to check in with the manager, of course, on the STR/ MTR side," he adds.
Josh says they list their STR/MTR properties on Airbnb, Vrbo, and Furnished Finder and use PriceLabs to optimize pricing automatically. They have been using Hospitable as their primary PMS for the last three years, and Josh thinks its AI features help them with hosting.
"And then playing a bit more with AI as it comes to even drafting some of the guidebooks for the listings and some of the responses to guests. It also helps if you have VAs. Maybe English isn't their first language. That is a helpful tool to bring on through." Josh also admits that he uses AI as "a one-click spell check."
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Using Marketing Expertise to Succeed in the STR Market
Josh's day job is doing national print and digital advertising for the winery. Still, he thinks his marketing experience is helpful when he needs to create content to attract guests to their STRs. For example, as they built the listings, it was easier for him to vet photographers.
"Photos and listings and how to stage it is everything. So, you definitely have to have the right vendor to do that. But I think the biggest help marketing has been for me has not necessarily been more listings and more bookings, but it's actually been the partnership side," Josh underlines.
When he attends different events, he sees that most people he meets there have tech backgrounds, and few specialize in advertising or marketing and social media." And especially in this age of personal branding and social media. Adding value to individuals in that sense has opened up many different partnerships that allowed me to get into all of these different deals with the amount of effort I would want to put in. So that has been the biggest play of the marketing side."
Advice to New Investors
Real estate investment requires dedication, research, and planning and can be risky. So, if you are starting to build your portfolio, Josh doesn't recommend you spend all the money that you have on one property.
"Whatever nest egg you must invest first, spend half of that. So if you have $100,000 saved up and you're going to invest in that, then you only have to spend $50,000. So that way, you have $50,000 of an oopsie budget. So whatever needs to happen extra, you feel confident, and it doesn't break the bank," he explains.
Building a team to assist you with your real estate investment is also important. "Whatever asset class you're thinking about, whether it be long-term, STR, commercial, etc., you have to put in a lot of reps to run numbers, meet other operators, and talk to lenders. And if you're not willing to analyze hundreds of deals, network with and get to 100 people managing or operating that asset class first to chat with. And if you're not willing to put in that work, then I wouldn't do it at all. Because you want to meet at least and have that many conversations before you ever do anything."
Tune in to the full episode of the Hospitable Hosts podcast to discover expert insights that can help you navigate the complexities of real estate investing.
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