How a Real Estate Broker Became a Tech Founder; and Why Women Need to Do It Too Artwork

Badass Women in Business

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Badass Women in Business

How a Real Estate Broker Became a Tech Founder; and Why Women Need to Do It Too

July 29, 2025 • Aggie & Cristy • Season 4 • Episode 36

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Lisa Troyano-Ascolese is not your average real estate broker. She’s a serial entrepreneur, tech founder, podcast host, and unapologetic advocate for women building their own path to freedom. In this powerful conversation, Lisa shares her evolution from ad sales exec to real estate powerhouse, and the pivotal moment when her CEO told her, “You’re never safe if you work for someone else.”

We cover everything from launching her first business in a corporate cubicle to inheriting a brokerage out of grief, and the inspiration behind her first-to-market mobile staging app, REStaged, aimed at reducing furniture waste. Lisa doesn’t hold back about setbacks, including floods, firings, and nearly losing her life during childbirth, and how each one fueled her mission to show women that entrepreneurship isn’t just possible, it might be the key to happiness.

If you’ve ever wondered whether to leap, pivot, or press pause; this one’s for you.

Episode Notes

In this episode, we explore:

Why Lisa left corporate America despite "being safe"
The emotional origin story behind her kids' event planning business—and why she didn’t sell it
Her rise in real estate and the truth behind luxury markets (beyond the reality TV glam)
How personal loss led her to take over and rebuild a brokerage
The origin of REStaged, a mobile app built to fight furniture waste and give agents a smarter way to stage homes
Navigating leadership, grief, and growth simultaneously
What freedom actually means for women entrepreneurs
Why mentorship, cash buffers, and knowing your weaknesses are non-negotiables

Key Quote:
"If you do the research, if there’s a need, and you build a buffer—then you owe it to yourself to try. Freedom is the point of all of this."

Guest Contact & Links

Lisa Troyano-Ascolese
Owner, Engel & Völkers Hoboken + Jersey City
Founder, myHOMEboken Team
Creator of the REStaged App