She Got Laid Off, Launched a Business, and Built a Real Estate Empire: The Untold Story of Lisa Troyano-Ascolese
Lisa Troyano-Ascolese didn’t set out to become a real estate powerhouse. Or a tech founder. Or the woman behind one of the only mobile apps in the country designed to fight furniture waste.
She just wanted freedom.
Freedom from bosses who screamed at her across cubicles. Freedom from corporate restructures, from layoffs, from the illusion that playing it safe meant staying safe. Freedom to build something that was hers.
And maybe most of all, freedom to show other women that they can do the same.
Lisa’s story isn’t clean or linear. It’s not the highlight reel you see on Selling Sunset or in startup success headlines. It’s messy, real, full of grief, reinvention, and hard pivots. It’s a story of risking everything to stay in alignment with your values, your purpose, and your gut.
And that’s why it resonates.
Corporate Perks and the “Safe” Illusion
Long before she owned two real estate brokerages and led a team of 30 agents, Lisa was working in online advertising sales in Manhattan. She had the expense account, the office perks, the dream-on-paper job. She was safe, or so she thought.
But something was nagging. Her company was going through acquisition after acquisition. Layoffs became a recurring event. She kept surviving each round but felt the ground shifting beneath her.
So she did what any closet entrepreneur would do: she built something on the side.
“I started a kids’ event planning business. We’d throw birthday parties in people’s backyards, at pizza parlors, wherever. There was a real need for it in Hoboken back then,” she says. “I thought I’d pad my income a bit. Never thought it’d turn into anything serious.”
But she did something bold—she brought the business plan to her CEO. Not just any CEO, but one who offered weekly open office hours for employees to pitch their business ideas. A real-life Shark Tank, but quieter and more personal.
“I was sweating. I realized I had just handed my boss my exit strategy,” Lisa laughs. “But he looked at me and said, ‘It’s great. What’s the problem?’ I told him I felt safe working for him. And he looked right at me and said, ‘You’re never safe. I’m laying off half the company tomorrow.’”
That moment never left her. In fact, it changed everything.
Leaving Security, Choosing Chaos
The next nine months would prove her boss right. Lisa was caught in a swirl of company sales, missed severance, and job instability. That “safe” job disappeared overnight.
At the same time, her kids’ event business was gaining traction. And something else was calling: real estate.
Lisa’s mother had been a successful full-time agent, and Lisa had grown up tagging along to open houses. “I think it was always in my blood,” she says. “I figured I’d get my license and maybe do a few deals on the side.”
But it didn’t stay on the side for long.
“The birthday party business made me wait 10 years to have children,” she jokes. “It was exhausting. Meanwhile, I was closing real estate deals left and right.”
She made the leap, full time. But in hindsight, there’s one thing she regrets: “I shut the party business down. Didn’t even try to sell it. That was a mistake, but one I learned a lot from.”
And that wouldn’t be the last time she’d learn something the hard way.
The Unexpected Inheritance
Lisa never planned to own a brokerage. She loved selling homes and leading her team, but owning the whole operation? That wasn’t on her radar—until tragedy forced her hand.
Her mentor and best friend, who had brought Engel & Völkers to Hoboken, was dying of cystic fibrosis. On his deathbed, he turned to Lisa and asked her to save the business.
She said yes.
“I don’t recommend making someone promise to save your company while you’re dying,” she says, not joking. “It’s a lot to carry.”
The brokerage was in disarray. Grief-stricken agents. Financial losses. A leadership void. Lisa stepped in and turned it around, stopping the financial bleeding in six months, reaching profitability within a year.
But it wasn’t just about numbers.
“We were missing the heart he brought to the company,” she says. “I had to find a way to rebuild it in a way that honored him but also fit where we needed to go next.”
The turnaround wasn’t smooth. The first office she built flooded after she’d invested $100,000 into renovations. There were staffing challenges, emotional breakdowns, and endless late nights.
But she never stopped.
“I don’t fail,” Lisa says. “Or if I do, I don’t let it be the last chapter.”
Tech Trouble, a Couch, and the Birth of REStaged
In the middle of building her brokerage, Lisa stumbled into the kind of emotional, accidental moment that leads to innovation.
She had just been fired from a listing—one tied to a shady developer she’d called out for unethical behavior. The property was still full of staging furniture she’d paid for out of pocket. Thousands of dollars’ worth. Gone.
“I was sitting on the last couch in the brownstone, crying,” she remembers. “My mover—who’s still with me to this day—put his arm around me and said, ‘This isn’t the end. It’s the beginning.’”
And it was.
Lisa had a lightbulb moment: What if real estate agents could rent staging furniture from each other? What if she didn’t have to lose thousands every time a deal went sideways?
That idea became REStaged, the first-to-market mobile app allowing agents to share, rent, and reuse staging items, cutting waste, saving money, and offering flexibility.
She and her husband invested their own savings to build the first version during COVID. The feedback was immediate: people wanted it, but the closeout process was clunky.
“We launched too early because our developers said the best feedback is real-world feedback,” Lisa says. “And they were right.”
Now, REStaged is in its 2.0 rebuild with an eye on 3.0, AI integration, and strategic partnerships. “We’re looking for a developer partner now,” she adds. “There’s so much potential.”
And unexpectedly, her app touches a critical sustainability issue. Fast furniture is one of the largest contributors to landfill waste. REStaged helps extend the life of furniture, especially in urban, transitional housing markets.
“It started as a financial fix, but it’s become a mission.”
The Leader Behind the Brand
Lisa now leads two Engel & Völkers brokerages—Hoboken and Jersey City—with a team of 30 agents. Her leadership style? Honest. Protective. Long-view.
“If you asked my agents what kind of leader I am, they’d probably say I’m ethical to a fault,” she says. “I care about their long game. I’ll talk them out of a sale if it’s not right for the client.”
That integrity stands out in a field that’s often glamorized but deeply misunderstood.
“Yes, Selling Sunset put real estate on the map. But most people don’t see the actual work,” Lisa says. “You’re staging, you’re negotiating, you’re absorbing your clients’ stress. It’s gritty. It’s emotional.”
And most realtors aren’t making the money people assume. “The average annual income for a realtor is $23,000. You can’t live on that.”
What sets top performers apart, she says, is consistency, care, and treating the business like a craft, not a hustle.
Her Definition of Success? One Word.
Freedom.
Not yachts or passive income promises. Just the ability to design a life around what matters most.
“It’s freedom to choose your clients. Freedom to pick your kid up from school. Freedom to not ask permission to take a day off,” Lisa says. “That’s success to me.”
But success has evolved. After surviving a traumatic birth experience with her daughter, Lisa's priorities shifted again.
“We both almost died,” she shares. “It made me realize how little all of this matters if you’re not healthy. If your family’s not okay. I’m building for her now. That’s the compass.”
Her Advice to Future Founders
Lisa doesn’t sugarcoat entrepreneurship. She calls it “a very lonely business.” But she also believes it’s one of the last real paths to independence and wealth.
If you’re thinking of taking the leap, here’s her checklist:
Have at least 12 months of savings. “Don’t leave without a buffer. The world’s on fire. Plan accordingly.”
Know what you don’t know. “I didn’t code the app. I hired experts. Know your lane.”
Apprentice or intern if you’re new to the industry. “Work for someone else to get the lay of the land.”
Find a real mentor. “Someone who wants you to win and has skin in the game. That relationship saved me.”
And her last piece of advice?
“If there’s a need, and you know how to fill it, do it. Figure out the rest on the way. The world is changing. You need to bet on yourself.”
Why You Should Listen
Lisa’s episode on Badass Women in Business is more than a business story. It’s a blueprint for resilience, clarity, and calling your own shots. It’s about building something from heartbreak. About turning a couch meltdown into a tech company. About taking the road no one handed you and building the thing yourself.
If you’ve ever asked:
Is this a sign to quit?
Am I cut out for this?
How do I know when to pivot?
This conversation is for you.
Lisa isn’t selling a dream. She’s living the work. And reminding all of us that sometimes, the scariest leap leads to the most grounded kind of success.
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