How She Built This

April 2025 Meetup With Chara & Eva

This month’s investor meetup left me feeling incredibly inspired—and a little emotional, too. We welcomed two phenomenal speakers, Eva and Chara, for our “How She Built This” series, and their stories were a powerful reminder that you don’t need generational wealth or a huge bankroll to start investing in real estate.  All you need is hustle, creativity, and the courage to make the best decision for you—even if it goes against what the “experts” are saying. 

What I appreciated most about Eva and Chara’s journeys is how different they are from each other—and from the one-size-fits-all advice we so often hear in big-name podcasts and books. Rather than sticking rigidly to a single investing strategy, both women have assessed their options in real time and taken action in a way that made the most sense for their lives. It was especially refreshing to hear them talk about selling properties (gasp!) as a smart move—because sometimes, selling is the best way to grow.

They also have totally different approaches to Airbnb management, proving once again that there’s no single “right” way to be a successful investor. How do they do it?  They know their why. When your goals are clear, the strategy becomes much easier to align.

Eva’s Story: Intentional Growth from an Accidental Start

Eva’s real estate journey started unintentionally—with the purchase of a condo in Old Orchard Beach right after college. She worked multiple side jobs to cover the mortgage and eventually bought out her partner after a split. When she sold that condo, the profit became the seed money for her first real investment: a two-unit in OOB that she now runs as a successful Airbnb.

From there, she scaled up to a two-unit in Downeast Maine. When that property didn’t turn out to be a strong performer (thanks to poor property management), she decided to cut her losses and sell rather than stay stuck and trying to make it work.  Her gut was right and she managed to sell it for a profit and reinvested in what she calls her “vacation rental dream home” in Limerick. This one doesn’t cash flow as strongly, but it offers something even more valuable: joy. Eva shared how much she loves hosting families, writing handwritten notes to guests, and creating meaningful experiences in her homes. Her repeat Airbnb guests speak to the care she puts into every detail—and the deep sense of connection she fosters through her properties.

Chara’s Story: Grit, Ingenuity, and a $500K Payday

Chara’s story is nothing short of remarkable. As a teenager, Chara was a ward of the state and was emancipated at a young age.  After a divorce (and with two young kids!), she re-entered the workforce just seven years ago. Within two weeks of her decision to go back to work, she landed a high-paying job (if you know Chara, this would not surprise you!).  After a ton of research into different markets and some strong intuition, Chara used her earnings to dabble in the stock market and turned a $35K profit in record time! That win gave her the capital to buy her first investment property: a waterfront camp.  

Once she purchased her property, she hit her first big challenge—she had no money left for renovations. With grit and ingenuity, she found a young couple willing to trade labor for free rent. She supplied the materials, they did the work, and within a few months, the property was ready for summer bookings. Her Airbnb strategy? “Heads in beds.” She maximized occupancy to generate strong returns (although her neighbors weren’t huge fans).  

Flash forward 5 years, and Chara decided to list the property. While it made a great income, she started to wonder if the hassle of management was worth it and if there were other ways to invest her money.  Since she didn’t need to sell, she priced it ambitiously—and got what she wanted. Her net gain? Over $500,000!!! She’s now holding some funds for her next deal through a 1031 exchange (thanks to last months speaker, she knew exactly what to do and reported a great experience with Brendan Barry at Marcus Clegg), earmarking a chunk for taxes, and investing the rest. I was honored to represent Chara in the sale of her camp, and watching her close on this chapter—knowing the full scope of her journey—was a bit of an emotional moment for me. Her story is a testament to resilience, resourcefulness, and what’s possible when you bet on yourself.

On a personal note, this group continues to be one of the most meaningful parts of my month. Seeing how far we’ve come since we started meeting nearly three years ago and the community that we have built really is so special. A big thank you to Eva & Chara for reminding us anything is possible when you put your mind to it.