Dawn Dickson, Flat Out Heels, Woman Entrepreneur


sent me an email asking me to coffee when she was in NYC.  Along with
that she sent me her business plan and what she had built.  Her concept Flat Out Heels
stuck with me.  I had been at a party where I wore a pair of heels (for
the first time) that literally destroyed my feet.  If I  had a pair of
Flat Out Heels in my purse it would have saved me. If there was a
vending machine for shoes in the place the event took place I would have
bought a pair.  I engaged Dawn on email about what she was building. 
The idea of having shoe kiosks made total sense.  I remember as a kid
going to the local Peoples drugs store to buy a pair of Dr. Schols sandals when they were the rave.  Why not flats? 

Dawn grew up in Columbus, Ohio.  Her Mom was a stay at home Mom who
ran a home daycare center where there was always at least 10-15 kids
under her care.  She was very involved in her kids lives including being
on the PTA but really she was an entrepreneur.  Her father was a
contractor of real estate properties that he bought and sold including
others peoples who contracted him.  In essence he was an entrepreneur
too.  Dawn was the product of a childhood sweetheart relationship.  Her
parents were 20 and 21 when Dawn was born.  They never got married.

Dawn can't remember when she didn't work.  At 14 she began working
summers at a youth program and by 16 she was a counselor there.  She
continued to be part of this organization all the way through college. 
She later became a mentor to many of the kids who went there.  When she
was younger she engaged her Mom to do a paper route with her to make

After graduating high school Dawn stayed close to home going to Ohio
State as an education major.  She always thought she would be a
teacher.  After her first year she changed her major from education to
journalism with a minor in marketing.  She thought she would be a
reporter on TV.  She graduated in 2000.  Dawn went full time to school
as in all year so she graduated pretty young. 

The last year of college Dawn worked for NBC on the interactive
desk.  It was one of the first companies in the area uploading streaming
videos.  She learned about digital media content and with that a whole
other interest was born when she realized this was the future.  She was
hired full time by NBC after graduation.  It was there that she learned
how to write code and through that she ended up building a website on
the side that turned into a whole different career that she embarked on
after taking another job that went nowhere.

She left NBC after a year because she applied to the DeVry Institute
of Technology.  She was so turned on by what she had done at NBC that
she wanted to take it to another level.  When she was accepted there she
also got into a training program at Nationwide Insurance Company as an
intern.  She'd work during the day and go to school at night.  It was a
two year school.  Once you graduate from the Nationwide training program
you become a full time employee.  She went because they were just
figuring out how to use the internet to build a platform for online content.  She was young and trying to figure it out how to make the most of the technology she had begun to learn. 

After finishing her internship she worked on the intranet for the
entire company.  Through that she was able to see all the jobs that were
being posted.  She noticed there was a job opening as the Marketing
Manager for a subsidiary company of Nationwide.  Dawn decided the best
way to get that job was to email the President of the company directly
instead of going through normal channels.  She landed the job and build
an intranet web system with the IT department to market insurance broker
products for the agents.  She started that job on 9/11 and she was 21
years old.

It wasn't the best day to start a job and a year later, although she
reported to the President of that subsidiary, she wasn't being
challenged.  She was the youngest person on the management team and the
only person of color.  The good news is she met this guy there that has
ended up being her business partner through many iterations of her
career.  They both decided to build a site called Urbanstarr. 

Urbanstarr was a guide of all the activities happening around the
city.  There weren't any resources on line in Columbus Ohio where you
could find out about music, arts, restaurants, etc.  It was 2002. After
three months Dawn quite her job and her partner stayed working full
time.  She started doing grass roots gorilla marketing collecting over
10,000 email addresses at festivals and clubs.  Dawn decided to move to
Atlanta to learn more about the events and promotions world.  She wanted
to develop contacts.  At this point the site was even doing some live
streaming through UTube.  She ended up staying in Atlanta for 1 year and running the site from there. 

When she returned to Columbus she started her own events and planning
business.  She started monthly members only events, figured out how to
get sponsors and how to raise money .  It was  during a time when many
event producers were beginning to not only bring their talent to the
table of getting an event done but bringing sponsors with them.  She
started doing a variety of events for non-profits and decided to really
understand the world she entered that she would go back and educate
herself again.  She went to Indian Perdue in Indianapolis and got a certificate in fundraising management.  It was 2007 and the recession hit. 

In Columbus, people who she was doing business for were having a hard
time paying Dawn her fees.  At this point Dawn also had a daughter. 
She thought to herself what is recession proof?  The answer is sports
and entertainment so she picked herself and daughter up and moved back
to Atlanta.  She created a non-profit consulting company for athletes
and entertainers who wanted to get behind events that made their brand
look good. She really hit her stride and decided after three years to
pack it up.  Her daughter was 5 years old and she felt like she had to
to focus on her daughter.  She had this vision that a new idea would
come to her and she wanted to be able to create enough wealth so she too
could be philanthropic.  She upped and moved to Miami. 

In Miami she got a job working at a yogurt shop for the first 8
months.  People kept calling her to do events but she wanted to get past
that business.  One day a friend begged her to help with an event she
was doing.  All Dawn needed to do was stand at the door for 8 hours and
keep the list of people coming in.  She stood there and within a few
hours her feet were killing her.  She couldn't switch into a pair of
flip flops because it wasn't professional but what was the option.  The
next day she spent some time looking for a flat that would be an easily
accessory to tuck in your bag for a great price point but could not find

She started doing some research.  She remembered something she had
read a few years ago about a vending machine in the UK called rollasole. 
She contacted them to see if she could be their US distributor.  Their
only repsonse is she could buy the shoes from them wholesale.  As Dawn
said, entrepreneurs must be half crazy because we just do it because we
figure out how to do things our self.  She figured she could made her
own shoes.  She wrote a business plan and through old connections in
Atlanta got $30K to start.  The hardest part was finding the vending

She got on Alibaba and figured out to make the shoes in China.  The
first edition was a little flimsy and she wanted something firmer.  The
real goal was finding the vending machines and doing toss away shoes. 
She had to find a vendor to make a vending machine that would take
credit cards.  In the meantime she ended up with 2000 pair shoes and she
began to sell them on Facebook to raise cash.  Through those customers
she got feedback on how to make a better shoe.  The shoe had to have an
elastic back, a hard sole and be washable.  She finally found a company
to make the machine for her that would take credit cards, debit cards
and cash. It took time to develop.  She had both, the shoes and the

Dawn secured another $230K to grow her business.  She also got a
contract with Atlanta airport to put her first Flat Out Heels vending
machine in.  She now has 5 machines.  The second machine is going to be
in the Fountainbleau nightclub in Miami and other clubs.  The 5th
machine is going into the Georgia World Conference Center.  Dawn wants
to roll out 100 machines over the next 2/3 years.  The original guy who
she met at the insurance company is still her partner helping with
design. He is a professor of design at a University now and so he does
this for her on the side.  She will be 35 on January 1st and by then she
will be either managing vending machines worldwide or move this idea
into a franchise.  The company is split in two with a vending machine
end and a shoe end.  The only time they connect is through the Flat Out
Heels vending machine.

Dawn is a character and full of life.  What is interesting is how she
had continued to just move forward trusting her own instincts.  Some of
the decisions she had made most people would not make like just up and
moving to Miami after bringing in the cash with a business she was
already doing fine in to serve up frozen yogurt.  Most people would
never have left NBC but she wanted to continue to take what she learned
and move forward.  She really had not had a guiding light to help her
think these things through but just an entrepreneurial spirit.  She just
figured it out as she pointed out everything is on line so you can
teach yourself.  I give her huge kudos.  Smart idea with relentless



Comments (Archived):

  1. Lisa Abeyta

    I can see these going like hot cakes in airports, convention centers, urban hotels, ballroom ladies’ rooms…

    1. Gotham Gal

      me too

  2. Cynthia Schames

    It’s solving a real problem, and Dawn sounds pretty amazing.But…Dr Scholls sells folding flats in drugstores for $10 already. No vending machines to buy, maintain, stock. What am I missing?

    1. Gotham Gal

      Ah. Didnt realize that. Shes going after convention centers airports ans clubs

  3. Tracey Jackson

    Love these. Great idea! Go Dawn.

  4. Liz Rueven

    Emergency relief when and where we need it. LOVE IT!

  5. Mike Fields

    Dawn Dickson is a very impressive woman that I have had the pleasure to meet and work with! Oh and she is beautiful too! (Insert smile here)Mike

  6. Sarah Beeny

    A nice story but it sounds like she’s just copied that Rollashoe idea, good luck with it!