My First Business Died - But It Helped Make My Next Company a Success

When government policies and decisions killed my buzzy New York startup, I learned to build a better (and more sustainable) operation.

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My First Business Died - But It Helped Make My Next Company a Success
Image credit: Courtesy of Nowaday
Magazine Contributor
4 min read

This story appears in the March 2020 issue of Entrepreneur. Subscribe »

In 2016, New York City made an announcement that locals had been dreading: Starting in 2019, the L train subway tunnel — a major connection between Manhattan and Brooklyn — would shut down for 18 months of repairs. It would be so disruptive that people actually moved to different neighborhoods in order to be closer to a functioning subway line come 2019.

Then, just four months before the shutdown was going to begin, New York’s governor sprung a surprise. He announced that the L train wouldn’t shut down after all. (The repairs would happen on nights and weekends.) Some people were elated. Others were annoyed. And me? I was shocked…because I’d spent the better part of the past year building a business designed to serve people impacted by this closure.

Related: Why Embracing Failure Is Good for Business

Suddenly, all my work was destroyed. Or so I thought. I eventually came to learn an important lesson in entrepreneurship: Even when plan A fails, it can set you up for a better plan B.

Back in 2016, I was one of the 200,000 commuters whose routes to work would be disrupted by the subway closure. I wanted to stay in my beloved neighborhood, and I eventually decided to build a solution for people like me. After months of ideating, I had it. My startup, a carpooling service and platform, was called The New L. I assembled a small team, partnered with a fleet of drivers, collected data from nearly 5,000 interested customers, signed corporate contracts, generated interest from large buildings and companies that wanted to subsidize our service for their employees, and got a lot of press coverage.

We were ready to go…until, of course, the city blew up my plans. I was happy for the commuters whose lives wouldn’t be disrupted. But now what?

Related: 6 Surprising Rules for Business Success

I’d caught the entrepreneurial bug, and I wasn’t ready to give up that dream. A coworker from my day job and I started brainstorming new ideas, and we realized we were already partway down a path. My commuting company was dead, but building it had taught me a lot about urban mobility, efficient systems, and destination-based travel. What if we took those lessons and applied them to something people always want — sightseeing!

This is how we developed a company called Nowaday, which launched in New York this past November. Our first offering is a private tour of the city, given in a gorgeous 1920s vintage car. 

Tours like this are hard to plan; New York can throw a lot of unexpected things at you. If there’s a traffic closure or a parade, Nowaday still has to deliver a 60-minute experience without being stuck in traffic. That was a challenge, one that would require 24-7 monitoring. But here, the experience of The New L served us well. We’d already learned how to coordinate thousands of commuters, so doing it for private tours was much easier.

Related: How to Recover From Your First Failed Business

Within months, we’d developed Nowaday’s MVP. We bought our first car, put it on the road in early 2019, and delivered hundreds of rides in beta, collecting instant feedback from customers. Then we went to investors to enable us to build this company the right way. We raised $3.5 million and bought a fleet of 12 vintage cars, working with a team in Detroit that helps with sourcing and restoration. 

The rides have been a quick success, but we have much bigger plans for Nowaday. We are more than a touring company; we’re an experience company. We plan to uncover and narrate every city’s most fascinating stories, from food to entertainment, for locals and tourists alike. The logistics of this are tough, but I feel prepared. No matter the challenges, I found a far more sustainable business than The New L ever could have been.

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