Member Spotlight: Exclusive Interview With Jesse Mastro, CEO of RentAnAC
Updated: Apr 28, 2025
When it comes to turning everyday challenges into innovative solutions, few do it better than Jesse Mastro, the entrepreneurial force behind RentAnAC. In a world where comfort and convenience are paramount, Jesse's vision has reshaped how we think about temporary cooling solutions, offering relief in the most unexpected ways.
In this exclusive interview with EO Boston, Jesse shares his journey, from the spark of inspiration to scaling RentAnAC into a thriving business.
Whether you're a budding entrepreneur or simply curious about the genius behind this unique service, Mastro's story is a testament to the power of vision, resilience, and a willingness to take risks. Let's take a closer look at how he's not just cooling homes but also heating up the business world.
Tell Us About Your Business
On the surface, RentAnAC is a window AC rental and sales company. But behind the scenes, we are so much more! RentAnAC is the fusion of a service business with cutting-edge technology and modern design.
With a custom-built e-commerce platform, sophisticated logistics software, and an obsessive focus on user experience, RentAnAC operates like the "Uber for ACs," delivering and installing several hundred units per day.
With locations in Boston, NYC, and Providence, we serve residents and commercial clients—including universities, property managers, and multi-family buildings—throughout the Northeast.
How Did You Become an Entrepreneur?
I’ve always felt an itch to do or build things better and challenge the status quo. I started my first business at age 22, which was an iPod accessory company (I’m dating myself). I’ve started five companies in total, with two still operating today and one acquisition.
What Have Been Your Greatest Challenges and Successes in Business?
The most challenging experience I’ve encountered in business is raising capital from the wrong partner and losing control of a business. On the flip side, my greatest success has been taking back the reins of a struggling business and turning it around to grow at 50% YoY for the last three years.
How Do You Network With Other Entrepreneurs?
I have a core group of entrepreneur friends I’ve networked with for the last 15 years, but I’ve not networked as much recently, hence EO!
Who Have Been Your Strongest Mentors?
Robert Glazer from Acceleration Partners and Chris Colbert, author and entrepreneur. They have both been big influences in my life. I worked with Bob for several years during a gap between operating my own companies.
Why EO Boston?
It’s only been one month, so I am still ramping up. I can say that my experience in the EO Accelerator Program many years ago was extremely valuable (knowledge, networking, connections, etc.), and I imagine EO will be even more so.
What’s on the Horizon for You?
I just started another company called Envr Air, which is applying a business model similar to RentAnAC to the HVAC heat pump world.
What’s the Best Piece of Advice You Can Give to Up-and-Coming Entrepreneurs?
Learn to hire well and delegate effectively as soon as you can. The sooner you can work on “your business” versus in your business, the better chance you have to succeed.
Connect With Jesse Mastro and Other Successful Business Leaders
Under Jesse Mastro’s leadership, RentAnAC has grown into a top-tier business, making millions of dollars in revenue. If you're a startup trying to replicate RentAnAC’s success, we can't think of a better way of doing so than directly connecting with the brain behind it.
EO Boston gives you that avenue to link up with not just Mastro but other leaders who are making giant strides in their fields. You can join EO Boston today or start with our Accelerator Program to get access to peer-to-peer learning, mentorships, and a range of well-curated entrepreneurship events to elevate your game and take your business to the next level.
Thinking about helping children take ownership of learning, I find the smaller practical questions more interesting than a quick conclusion. Making a small choice can help pupils feel responsible for the way they approach a task. I would use that point as a starting question when considering student learning ownership. I can imagine different answers depending on the situation, so I would want to understand the context before drawing conclusions. Which decisions can children make meaningfully within a structured lesson?
What draws my attention to creating supportive school learning environments is the possibility of making an unfamiliar subject feel closer to everyday life. Clear expectations can make it easier for pupils to understand what a task is asking of them. I would use that point as a starting question when considering supportive school education. I can imagine different answers depending on the situation, so I would want to understand the context before drawing conclusions. How can classroom expectations remain understandable without becoming a long list of rules?
Thinking about connecting practical school skills with future choices, I find the smaller practical questions more interesting than a quick conclusion. Trying a task can help a student notice whether an area of study suits their interests. It gives me a more concrete starting point for thinking about practical school skills. I am more curious about the process than a polished result, because the steps in between are usually where questions appear. What kinds of activities help students explore possibilities before making a decision?
What interests me about exploring local heritage in Ostrorog is how a broad idea becomes part of an ordinary day. A community's history can become easier to picture through ordinary objects and places. I would use that point as a starting question when considering Ostrorog heritage education. I am still thinking through the details, and a small example would help me picture how this works in practice. How could students present local heritage in a way that welcomes further questions?
When it comes to connecting classroom learning with Bratkowice, I would rather understand one useful detail properly than rush through a long list of ideas. A local topic can invite pupils to contribute knowledge that is not found in their textbook. This is why I would approach Bratkowice school projects with a specific question rather than a fixed expectation. I am still thinking through the details, and a small example would help me picture how this works in practice. How would you make room for those contributions while keeping the project focused?