At the desk of: Caren Maio

The Nestio CEO on overcoming teen anxiety, office-wide poker games and reeling in mega landlords and VC backers for her rental listing platform

Caren Maio (Photos by Emily Assiran)

At 34 years old, Caren Maio has already raised $16.4 million to bankroll her company, Nestio.

The startup —a platform that allows property owners, managers and brokers to track, manage and market their residential rental listings — was one of the first to zero in on this notoriously opaque corner of the market.

The company — which Maio launched with co-founder Mike O’Toole (he’s now the company’s CTO) in 2011 after enduring her own frustrating New York City apartment search — claims to have hundreds of thousands of rental units on its platform. And it touts the fact that it’s helped clients reduce the number of days their listings linger on the market by an average of 20 percent.

Those clients include such mega landlords as the Moinian Group, the Durst Organization, the LeFrak Organization, Two Trees Management, Rudin Management and a slew of others. And several of those clients have also been converted into investors, with some kicking in for Nestio’s latest $4.5 million fundraising haul and previous rounds.

As the firm, which has 40 employees and is stationed in a roughly 7,000-square-foot, loft-like office in Chelsea, has collected more VC cash, it’s continued to roll out new products, including consumer-facing websites for landlords.

Maio, who graduated from New York University in 2007, grew up in Red Bank, New Jersey, in a family of business owners: Her father and uncle started their own recycling company. After brief stints in the marketing departments of Nike and the Wall Street Journal, she, too, struck out on her own. Maio and her dog, Astor, recently moved to the Upper West Side from Williamsburg.

Her business bible

Maio gives a copy of “The Hard Thing About Hard Things” to every new Nestio employee. The book, which was written by Ben Horowitz — the co-founder of venture capital firm Andreessen Horowitz — gets into the challenges of the startup life. “It’s informed not just how I run the business, but it also gave me perspective,” Maio said. “It’s so frank, and it talks about the things most people don’t want to talk about.”


Maio wears two rings on a necklace. The first, from her Roman Catholic paternal grandmother, is a mini Virgin Mary. Maio considers herself more spiritual than religious, but the ring is sentimental. The second ring, from her maternal grandmother, is from Hunter College. Getting to that level of education was “sort of a rarity for women at the time,” said Maio, who is herself breaking a glass ceiling as one of just a few female CEOs in the startup world.

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This gong has been in the office for about two years and gets love when an employee closes a big deal. “It can be a little alarming when you don’t see it coming,” Maio said. For staffers who don’t want to cause a scene, there are bells throughout the office. Maio said the gong is just a fun way to acknowledge progress, but the percussion instrument has become something of startup sensation.

Elephant and rocks

The elephant figurine was a gift from Nestio’s sales operations manager, Rahul Nagardalekar, who got married in India and brought it back for Maio. Meanwhile, the rocks are Maio’s “modern stress balls” — they were given to her by her dad when she was an “angsty” and “shy” 12- or 13-year-old struggling with social anxiety. Today, that shyness is hard to detect and Maio is regularly in pitch mode, talking to clients and VCs.

Celebrity cards

Maio keeps this deck of cards featuring pop culture and historical figures such as Whitney Houston, Steve Jobs and Frida Kahlo on her desk. “We have shuffleboard in the office, but I’m more of a cards person,” she said. Although she doesn’t have a regular game, she said she has plans for office-wide poker in the works.

Nickelodeon logo

Nestio’s conference rooms are all named after Nickelodeon TV shows from the 1990s. When the company was building out its office, Maio took suggestions for how to name the spaces — another common startup trend. Today, meetings are held in “Rugrats,” “Guts” and Maio’s personal favorite, “Legends of the Hidden Temple.”