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How to Bootstrap a Business While Living in NYC

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bootstrap a business in NYC

Inc., Forbes, and the New York Time’s Fashion and Style section have covered Lori Cheek’s story. The focus is often on her business, a unique take on the mobile dating space, or Lori’s self-run guerilla PR campaign and relentless hustle. One aspect that has been overlooking is how Lori can afford to bootstrap a business while living in one of the world’s most expensive cities.

How to Bootstrap a Business While Living in NYC

Start with a fund.

Lori set out to become a tech entrepreneur. After graduating from the University of Kentucky in 1996, she moved to New York City and started as a sales assistant at a furniture company. Over the next 15 years, she climbed corporate ladders in architecture, furniture, and design firms, making her way to a six-figure income and a closet that wouldn’t be out of place in Vogue.

An interaction between a colleague and a stranger at a bar in 2008 inspired Cheekd, Lori’s app and business. The idea behind is simple. There are so many people you walk past on the street and never get to meet. What if you could connect with potential partners and do away with missed connections? The Cheekd app and idea has gone through several versions and now uses a low-energy Bluetooth to connect people users when an internet connection isn’t available.

The business started as a side project and became a full-time job in 2010. Savings from the corporate jobs helped fund the first few years, and in 2013 Lori pitched her business on ABC’s Shark Tank. The Sharks didn’t invest, but the TV appearance led to a surge of interest in the app, a round of investment from other sources, and a new CTO.

She’s never taken a salary from the company, which makes money from subscribers of the service.

Be prepared to sacrifice.

Lori’s closet has changed considerably since she quit her day job in 2010. The designer clothes and accessories were sold online and in consignment stores, raising nearly $75,000, and modest buys from Target and TJ Maxx replaced them. “It’s going to cost three times more than you think [to build a business],” says Lori, “you have to believe so much in what you’re doing… be creative. I’ve done my own PR.  You have to wear a lot of hats.”

Lori has a singular focus. “No one I know wouldn’t keep going with this, but it’s my baby. Getting through is a bit like a game.” Every extra dollar she earns is an additional dollar that can be used to spread the word about her dating app.

Find freebies and sell them.

One tactic that Lori uses to make money is to enter contests and attend events that offer free gifts. She’ll then sell the gift, sometimes a beauty product other times an internet router, online. On a secret shopping assignment, she might get paid and get to keep the product she’s told to buy, which can then be sold online.

Living in an expensive city like New York is an advantage in this case as it would be hard to find such opportunities in a small town. Lori says, “I know all the good happy hours, go to parties, and get free stuff.” She can rattle off a list of restaurants and stores that give free gifts or meals on your birthday and uses all sorts of apps and websites to get even more freebies or gift cards.

Get a flexible side hustle.

In 2014, four years after working on Cheekd full time, Lori was close to running out of money. Going back to working for someone else full time was off the table, she’s too committed to her business. Instead, Lori has made ends meet by finding a series of flexible, and not too time consuming, opportunities.

The most dramatic move was couch surfed or stayed at friends’ places while renting her West Village studio on AirBnB. It was risky and after 14 months she lost her lease, but not before making tens of thousands in profit. She’s now back in a place of her own, but the experience set her up with another opportunity, and she now helps manage others’ AirBnB properties.

Lori works some other side jobs to make money for day-to-day expenses and to reinvest in her business. She’ll walk dogs, house sit, water plants, and buy discounted items and sell them online. Some jobs are available through TaskRabbit, others are found on Craigslist or through personal connections.

Get paid to share your opinion.

Twice a day Lori checks Craigslist, bulletin boards, and focus-group apps like dscout looking for money-making opportunities. Keywords help guide her search – product test, app test, and focus group – and a few hours of work can be worth hundreds with the right opportunity.

Some focus groups can be dull, she admits, but that’s not always the case. During one related to a new Tony Robbin’s book, Tony came out afterwards and spoke to all the participants. A recent focus group had her tasting beer, not a bad way to make $120, and she’s had one-on-one feedback opportunities that pay as much as $400.

Build frugal habits.

In addition to finding creative ways to make money and market her app, Lori is an expert at finding money-saving opportunities. She often checks websites and subscribes to email lists that clue her into what’s happening around the city, but in speaking to hear it’s clear she knows many of the good spots by heart.

Inexpensive entertainment isn’t hard to find in a city filled with free movie screenings, happy hours, and fitness classes. Although she grocery shops at Whole Foods, she cuts coupons and is conscious of not overspending.

Lori changed her lifestyle to meet her budget and focuses on needs rather than wants. She uses the shared bike service Citi Bike, which costs $149 a year, rather than paying for the subway or cabs. She’s a hair model for L’Oreal, and sometimes gets a gift bag filled with free items that she sells online. Instead of paying for professional headshots, she found parties that offer attendees a free makeup session and headshot.

Is It Worth It?

Some may view giving up a high-paying job to work odd jobs while building, marketing, and doing whatever else is needed to build a business as a sacrifice. Lori enjoys the experience. Even if the paycheck isn’t steady, Lori says, “I’m so much happier with my life. Instead of building someone else’s dream I’m working on my own.”