The short-term rental industry has evolved dramatically over the past few years. What once seemed like a straightforward path to passive income has transformed into a sophisticated hospitality business requiring strategic thinking, operational excellence, and smart technology integration. For those willing to adapt, the opportunities remain significant, but they look very different than they did five years ago.
Jeremy Werden's journey from private equity analyst to successful short-term rental entrepreneur and SaaS founder offers a masterclass in recognizing market shifts, leveraging data, and building sustainable competitive advantages. His story reveals not just how to survive in today's competitive landscape, but how to thrive by focusing on what truly matters: exceptional properties, human connection, and operational resilience.
Most entrepreneurs don't begin their real estate journey by purchasing pontoon boats. But in March 2020, as COVID-19 shut down New York City and put Jeremy's private equity career on pause, he made an unconventional bet.
"I was watching a lot of Netflix at that time, and I was looking for signs of something to do," Jeremy recalls. Inspired by the TV show The Ozarks, he launched a boat rental business at a local North Carolina lake — one of the few activities deemed essential during lockdowns.
The timing proved fortuitous. Business boomed, and many of his boat rental customers were buying lake houses. They began asking Jeremy to help them rent out their properties. "At the time, I didn't know what it was called. I didn't know there was co-hosting or property management. I didn't know any vocabulary. I just said, sure. I can do that."
Jeremy's decision to focus on tangible, experiential assets while his peers dove into cryptocurrency reflects a fundamental investment philosophy: when everyone zigs, consider zagging.
"A lot of my friends were getting into crypto. The smartest people I knew were allocating all their time and energy to something extremely intangible," he explains. "I thought, all right, what's like the most hands-on experiential, real-world touchable thing there is? Being on the water on a boat."
This focus on real-world experiences has remained central to his investment thesis. It's a reminder that in a digital-first world, physical experiences retain tremendous value.
As Jeremy began managing properties and raising capital for his own investments, he faced a recurring challenge: demonstrating the financial potential of short-term rentals required pulling data from dozens of sources and compiling complex reports.
"I would create reports, documents, PowerPoints, spreadsheets to show them, give them a little bit of an idea and also show that I wasn't just going about this blindly," he says.
When people started asking to buy his materials, Jeremy recognized a broader market need. Rather than continue selling spreadsheets for $20-50 each, he leveraged his computer science background to build BNBCalc, a platform that generates comprehensive property analysis reports in seconds.
Three years later, BNBCalc has processed over 1.5 million property analysis reports and serves thousands of users. The platform addresses a fundamental inefficiency in the market: the time and expertise required to evaluate investment opportunities.
"Instead of pulling from 20 places, you can create materials and also get an idea yourself in a matter of seconds," Jeremy explains. "And then click the share button, text it with a friend versus, 'Hey, did you check your email? Can you hop on a zoom with me?'"
The lesson here extends beyond software development. The best business opportunities often emerge from solving problems you've personally experienced, because you understand the pain point intimately and can validate solutions quickly.
Jeremy's portfolio evolution challenges conventional wisdom about growth. While he's managed over 25 properties at various points, he's recently reduced his apartment holdings to focus on higher-quality, more experiential properties, all while increasing revenue.
"I heard someone tell me this: the number one thing that leads to high reviews isn't the number of bedrooms or the type of property. It's the quality of property," Jeremy notes. "If you just start off with a higher quality property, you're probably gonna get better reviews to begin with."
This mirrors a broader industry trend. Property managers worldwide are discovering that fewer, better properties often generate more profit with less operational headache than large portfolios of mediocre listings.
Jeremy applies the Pareto principle ruthlessly: "It's kind of like the 80/20 rule where 20% of your properties are gonna cause you 80% of your problems."
His solution? Be selective about what you take on. At this point, he focuses on:
One of Jeremy's most compelling insights challenges the assumption that you need to own properties to build wealth in this industry.
"If you can manage five decent houses, you can have a pretty good life," he explains. "These houses are making a hundred grand a piece, that's half mil a year, put your 20% management fee on that. That's a six figure business by managing five properties."
The math is striking: managing five properties can generate the same income as owning five properties, without the capital requirements, debt service, or ownership risk.
Despite the proliferation of large-scale property management companies, Jeremy sees persistent opportunities for boutique operators who deliver exceptional service.
"There's a lot of big property managers out there who manage hundreds, thousands, tens of thousands, and they're just not doing a good job," he observes. "This game is a very localized hands-on game."
The key advantages for smaller operators are:
Jeremy's approach to automation reflects a nuanced understanding of hospitality. While he leverages property management software, pricing tools, and AI-powered communication systems, he knows when to pick up the phone.
During summer flooding at his North Carolina properties, Jeremy personally called most guests despite being in Europe. "This is a hospitality business and things are gonna happen. And when they do, if you just connect somebody human to human, it generally alleviates like 80% of the stress."
Jeremy's technology approach follows a logical progression:
The principle: automate the routine so you have capacity for the exceptional.
Jeremy's current investment strategy centers on a simple question: "Why is this something that nobody else could do?"
His Kentucky property exemplifies this approach: a house with its own private five-acre lake and a 3,000-square-foot insulated pole barn. "The cost to even build this nowadays would probably be a couple million dollars. I don't even know how you build a lake."
This focus on irreplaceable assets provides multiple advantages:
Jeremy's properties have weathered hurricanes, historic flooding, and pandemic disruptions. His approach to resilience combines proactive communication with realistic expectations.
When flooding hit his North Carolina lake properties, he immediately contacted guests: "We told guests, 'You can't swim in the lake for further notice. Is the lake safe? I think so. But I can't guarantee anything to you. We're just going to inform you of what's going on.'"
Most guests appreciated the transparency. For those who couldn't use lake amenities, Jeremy offered compensation for alternative activities like go-karting and winery visits.
The lesson: guests are remarkably understanding when you communicate honestly and work to find solutions.
For U.S. investors, recent tax legislation has created significant incentives for short-term rental investment through bonus depreciation and the "short-term rental loophole."
Jeremy explains the mechanics, with the caveat that this is quick math and he’s not an accountant: "If you make a quarter mill a year and you buy a million dollar house, you might only have to put a hundred grand down. However, [on] that asset you might be able to show a quarter million dollar loss from depreciation. So let's say your job, you made a quarter mill from buying a house. You lost a quarter mill. Bang. Your tax bill just went sayonara."
BNBCalc has responded to this trend with a bonus depreciation calculator that helps investors, realtors, and accountants model the tax implications of short-term rental purchases. It's an example of how understanding regulatory changes can create product opportunities and investment advantages.
On building a portfolio:
On operations:
On market positioning:
On resilience:
The short-term rental industry has matured beyond the "throw any property on Airbnb and profit" era. Today's successful operators combine data-driven decision-making with exceptional hospitality, strategic property selection with operational excellence, and smart automation with human connection.
Jeremy's journey illustrates that success in this space isn't about following a single playbook, but understanding fundamental principles and adapting them to your unique circumstances. Whether you're managing properties for others, building your own portfolio, or creating tools to serve the industry, the opportunities remain significant for those willing to think strategically and execute consistently.
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