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Success & Career

How to Bootstrap a Business While Living in NYC



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.”

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Success & Career

5 tiny habits that can change your life and career



Tiny Habits That Can Change Your Life

When it comes to the daily grind, time seems to keep passing by – yet many things remain the same. We are so busy trying to get things done, keeping our heads above water, that we don’t take real time to think about things like balance, self-care, or making necessary changes.

Little do we realize that small tweaks at home and at work might create opportunities for us to have true balance, and even achieve that elusive success.

Let’s look at five tiny habits you can implement today to control the chaos – and start changing your life and career.


Tiny Habits That Can Change Your Life and Career

1.) Embrace the concept of a “clean slate” at work.

Tiny Habits That Can Change Your Life

This involves implementing a few simple routines and organizational tools upfront. This will save you time in the long run, and will leave you feeling satisfied at the start – and end – of your day.

For example:

  • Create folders in your e-mail inbox by person and topic. Be sure to move applicable items there. The feeling of a clean inbox can reduce anxiety and enables you to find important material faster!
  • Write phone messages on a notepad next to you each day.
  • Return each call.
  • Note the status of what you were able to do, what needs to be done, and cross out which ones have been taken care of.
  • Complete your list before you leave work.

Nothing feels better than looking at the list and knowing that you have attended to every person, every item, and every task you started with. Yes, more may come in later. But these were your starting tasks.

You are leaving with everything crossed off, a clean slate for the day. You can start tomorrow with a clean slate as well. You’re more organized: able to look at a detailed history of each item you did, each person you spoke to, each item you completed.

A well-structured system and way of doing things is mentally good for you. It’s also a nice feeling to walk away with a complete sense of accomplishment for the day.


2.) Surround yourself with people who nourish your soul, NOT people who infect it.

Tiny Habits That Can Change Your Life

Think about the people you chose to be with. Don’t feel guilty about setting boundaries, no matter who they are. Be honest if someone is a “toxic” person in your life. Surround yourself with folks who build you up, support you, are honest but fair with you, and those who have your best interests at heart.

We of course need people who are going to tell us the truth. But remember that truth can be told with kindness. We can give ourselves permission to distance ourselves from, or let people go. These are individuals who make us feel bad about ourselves, or take every chance they can get to criticize our every choice.

There is enough negativity in the world. We don’t need to have it in those closest to us. You will be amazed at the difference when you give yourself permission to set healthy boundaries. So surround yourself with healthy relationships. Stop feeling like you must endure unhealthy ones.


3.) Clutter creates anxiety more than you realize.

Tiny Habits That Can Change Your Life

Whether it’s your home or your workspace, getting organized makes a huge difference in your state of mind. So start practicing tiny habits that create structure.

At work:

Get those piles into drawers and desktop storage. File folders are your friends! Label by topic, date, etc. Having things organized and at your fingertips will save you time and a great deal of anxiety.

Have trays for things that are needed on a daily or weekly basis. Organize your office supplies neatly. Remember that your desk is also a presentation of who you are.

You may think that those piles make you look busy – but they really make you look disorganized. Create your own system so that you can locate anything instantly. That, is more impressive than a pile.

At home:

Think more in terms of scaling down to get organized. Make it a goal to make you space your solace. Organize, donate, and find a place for everything. If you have not used it in a year, consider donating. If things belong together, group them. Get the right storage to hold things.

Group things where they make the most sense. Move things where they work and function best. Get rid of things that no longer work, are expired, are outdated, or that could benefit someone else more than sitting in a pile at your home.

You will not miss them. You will probably feel pretty good for sharing the love. Nothing feels better as having a fully functional home where you can live and breathe; where there is no clutter, and where everything has a place.


4.) Practice good, daily self-care.

Tiny Habits That Can Change Your Life

It may seem so simple, yet we all seem to fall short when it comes to this vital area that impacts our lives and our careers. If we practice tiny habits of self-care, we function better, perform better, and surely, improve our opportunities for success.

Good self-care includes things, such as:

  • Getting enough sleep each night. This includes going to bed and getting up at the same time, seven days a week. When going to bed, there should be NO electronics, including screens or cell phones, as they stimulate the mind and keep you awake.
  • Eating food that nourishes you – such as whole foods, not processed foods.
  • Drinking eight glasses of water each day.
  • Enjoying treats in moderation, no need to crash diet!
  • Be sure to wake up 30 to 60 minutes earlier than usual to ease into your day, and allow yourself to practice your morning routine.

Whether it be reading the paper, listening to a podcast, watching a TV show, yoga, or morning meditation, how you begin sets the tone for the day. So set aside time in the morning so you are not rushed. This is an essential part of your day.

If you start rushed, you are going to feel that way the whole day. Starting with balance, leads to a balanced day.


5.) Self-talk is one of the most powerful habits we can change.

Tiny Habits That Can Change Your Life

If we think about how often we thought something negative about ourselves, someone else, or about a situation, we would see how powerful negative self-talk can be. Now think about how better our lives could be if we stopped ourselves before doing it. It’s possible – but it takes effort and conscious work.

You simply need to pay attention and catch yourself. But as you do, the difference can be profound. You start to see how by removing negativity and replacing it with realistic thinking, you feel more balanced. Imagine the impact it can have on your work and relationships, to not see things in the worst possible light?

By implementing these tiny habits, you can bring about tremendous changes to your work and personal life. A few would only be one-time tasks. While others require minimal, but – hopefully welcome – effort.

If things are not working well in these areas of your life, why not give these tiny habits a chance? You will at least be a little more organized. And hopefully, be well-rested at the end.



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Success & Career

7 Ways to Organize Your Day for Success



Organize Your Day for Success

Nope, don’t panic. I’m not going to start by telling you to get up earlier! As an Integrative Nutrition® Health Coach, I firmly believe in bio-individuality. This is the idea that we are all unique: just as some people can’t tolerate gluten and some can, there are early birds and others are night owls. Neither is wrong – they’re just different.

So yes, just as our definitions of success look different, how we structure our days for success will vary as well. However, I believe that there are some things in common.

For the sake of having a starting point, let’s agree that success is showing up in your life (career, relationships, physical activity, etc.) in the most biologically effective way possible (i.e., you are healthy in every sense of the word).

So how would you organize your day for success? Here are seven ways to try:


7 Ways to Organize Your Day for Success

1.) Wake up without an alarm if possible (see also #7).

Organize Your Day for Success

Jolting awake to an alarm is a sure-fire way to feel like you’re off to the races first thing in the morning. Instead, learn how many hours of sleep you are naturally inclined to. Then try to get that every night.

Waking up naturally prevents that influx of fight-or-flight chemicals coursing through your veins: nobody needs that kind of stress at the start of the day! Chronic stress can wreak all kinds of havoc with your body, starting a cascade of poor health outcomes.


2.) Start the day with screen-free “me time”.

The moment you check your email or social media, you are giving others power over how you spend your time. There will almost always be an email that just can’t wait or a post that brings on a severe case of #FOMO. Before you know it, you’re sucked in.

Instead of reaching immediately for a device, consider starting a new practice that can take as little as 5 to 10 minutes (or less) or as much time as you create for it: breathing, meditation, mindfulness, gratitude, journaling.

The Web is full of resources for these – just don’t go looking for them first thing in the morning! Are you an early bird? Use this gift of time to work out, meal prep, read, etc.


3.) Create time blocks (see also #5).

Organize Your Day for Success

As much as we think we can multitask, research shows we really can’t. “Task-switching” – what we’re really doing when we think we’re multitasking – can cost us as much as 40 percent of our productivity.

The solution: block out specific times on your schedule for tasks that require your full attention. During those times, close all other tabs and turn off all your notifications – and I mean all of them!

In between these blocks and not before, take a break to check email, make some calls – take care of some smaller tasks. Set a timer that indicates your next productive block is starting.


4.) Schedule your workouts and meals.

We seem to have time for everything but what really nourishes us: fuelling our bodies well and moving them regularly. As a health coach, when you tell me, “I don’t have time to…” what I hear is, “I don’t prioritize…”

I see you rolling your eyes. Let me tell you: if you do that enough, they’ll stick back there. But seriously – it comes down to this: if you wouldn’t cancel on your work, your client’s needs, your spouse’s needs, your kids’ needs, why would you cancel on yourself?

Meaningful self-care is putting on your oxygen mask first so you can help those who depend on you. Organize your day and put those blocks on your schedule. Treat them as unbreakable appointments with yourself.


5.) Multitask…intentionally (see also #3).

Organize Your Day for Success

Yes, I know I told you not to multitask. Now I’m telling you it’s okay if you do it intentionally. What does that mean?

In my work, I talk a lot about primary foods – all the other things in our lives that nourish us (or don’t!) besides what we put in our mouths. Think: sleep, career, spiritual practice, physical activity, time in nature, etc.

The multitasking I encourage is the kind that helps us nurture ourselves on the primary level, NOT the type that tries to manage a staggering number of little tasks that make our schedules so overwhelming.

What this looks like:

  • Need to spend quality time with family members? Instead of adding an outing (with all the planning, preparation, and consensus-building it requires), combine it with another area that needs some attention: take suggestions on the week’s meals, shop together, do some meal prep, etc.
  • Missing time with your girlfriends? Combine it with a workout or better yet, a walk in nature.
  • Desperate to do a little meal prep for the week? Invite a few friends over to cook so that you all get to stock up for the week. (There might be wine involved?)
  • House feeling like a hardhat zone, but you’d rather read? Clean while you listen to an audio book.
  • Time constraints making you choose between a workout and your spiritual practice? Take a walk in nature or practice a walking meditation.


6.) Make a plan for tomorrow.

You don’t have to organize your day down to the minute (although that works for some people). Instead, write down 1-3 large tasks to be done tomorrow and prioritize those once you’re done with your “me time.”

Are the tasks unpalatable? Brian Tracy has written about this concept in his book ‘Eat that Frog! 21 Great Ways to Stop Procrastinating and Get More Done in Less Time’. He calls the tasks we are most intimidated by (and therefore put off doing) as “frogs”.

His recommendation: start your work – not just the day – by “eating a frog”. If all the frogs look big and ugly, eat the biggest, ugliest frog first.


7.) Get to bed on time to get the sleep you need (see #1).

Organize Your Day for Success

Once you know how many hours of sleep you need, organize your day and figure out when you need to get to bed. Make sure to end the day as you began it: NO screens for at least 30 minutes before bedtime!

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