How to survive the roller coaster of launching your own business

Nestio CEO Caren Maio knows the thrills and challenges of being an entrepreneur

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NEW YORK — The idea of starting a business can be incredibly daunting for many entrepreneurs. The myriad challenges — like securing funding and building a product consumers will actually use — can be difficult to navigate.

Caren Maio

Caren Maio, the CEO and co-founder of Nestio, a New York City-based software company that streamlines marketing and leasing for owners of multi-family buildings, took the Inman Connect stage to share her story of the “roller coaster” of owning a business.

“Starting a business is hard work,” she admitted, recalling LinkedIn founder Reid Hoffman’s quote that it’s like “jumping off a cliff and assembling an airplane on the way down.”

Maio started her business in 2011 with three other individuals who felt frustration over the apartment rental process in New York City. They had $10,000 in the bank and were working out of her 500-square-foot apartment.

Fast forward to 2018 and Nestio has a team of 30 employees with decades of experience in real estate and building management. They manage about 2.5 million units across the country and have raised nearly 12 million in funding.

“Getting from there to here I wish I could tell you it was a straight line,” Maio said, admitting the ups and downs. “I wish I could tell you it was a hockey stick.”

Be willing to pivot

One of the biggest lessons she learned early on was that entrepreneurs need to be willing to pivot. In product’s first rollout, she held her idea close to the vest.

“I built that business largely in isolation,” she said. “I was terrified of talking to people.”

But once she brought it to market, she quickly learned the value of feedback. After talking to people she learned many multi-unit owners were frustrated by the antiquated systems for managing inventory and marketing that were in place.

So for Nestio’s second rollout, she released the product very early to a select number of clients.

“Solicit feedback early and often,” Maio suggested. “Talk about your idea, talk about your business. You will learn so much.”

She recommended creating an advisory board and staying close to customers — getting coffee with them, attending their open houses and even shadowing them.

Keep good company

Another important lesson Maio learned was to surround yourself with good people. When she took the revamped business model to Joanne Wilson, one of her first investors, she was terrified, but what she found was that she had an investor that believed in her and believed in her team. She walked away with a partner and even more funding.

Take care of yourself

As Nestio finally began to achieve success, Maio found herself burnt out, which lead her to the final lesson: self-care is important.

“I was miserable,” she recalled. “I hit a wall. I was living out of a suitcase.”

But then she reached out to other entrepreneurs and they started sharing war stories and discussing the ups and downs of starting a business. Hearing that she wasn’t alone in struggling helped her break her routine and take time for herself.

“I built a routine that worked for me and protected my time, and I started to take care of myself,” she added.

Now she embraces the “roller coaster” of being an entrepreneur. She never gets too down, knowing that an upswing will come, and stays humble, knowing that the next dip is ahead.

Read all of our coverage from Inman Connect NY 2018.

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