Entrepreneur, Founder, Technology, Women in Tech

How Dawn Dickson Launched and Secured Capital for Her Enterprises!

Women of colour have been starting businesses at an alarming rate! Even though Women of Colour  are slaying their business goals, they are still less likely to be awarded any capital to launch a startup or start a lucrative business. Dawn Dickson is changing that  narrative.

Dawn Dickson is a serial entrepreneur who has launched four successful companies. Her most recent ventures are Flat Out of Heels, a rollable flats for women who might not be able to carry shoes in their bag and Pop Com, a software solution that makes vending machines more intelligent. She started her career in journalism and eventually transitioned into a tech. She shared her career journey with LFE:

Flat Out of Heels is pretty much solving every woman’s problem. I hate walking in heels so foldable flats are a life- saver! What was the aha moment behind it? I created Flat Out of Heels rollable flats out of necessity. In February 2011, I was attending an event in South Beach, Miami dressed to the nines in six-inch heels. After standing for hours my feet were on fire and I desperately searched for a place to purchase some affordable flats for relief…to no luck. It was then that I had my ‘ah-ha’ moment and set out to create a fashionable, durable and must-have rollable flat that is chic and durable enough for everyday use and dispensable out of vending machines to make purchasing convenient.

National Urban League “Hero’s of the Movement” Award

What are some of the challenges you have faced as a black woman trying to pitch to venture capitalists? When I first started to raise capital in 2013 investors told me that they do not invest in shoes and they are focused on tech companies. They did not consider Flat Out of Heels to be a tech company, despite our entire distribution and marketing strategies being tech-enabled and online, however I saw them funding many other web based stores that were started by my white counterparts. I have even seen VCs pouring money into shoe companies like Birdies and All Birds. I knew then that I was facing an uphill battle. That did not stop me, I just used a different route. I raised money from my close network of friends and family and I also won significant capital in pitch competitions. Then I decided I was not going to look for more investors, but just focus on customer revenue and scale.

After we started generating traction I secured my first, and only, VC investment in Flat Out of Heels from Backstage Capital. Backstage Capital also invested in my software/hardware company PopCom, I have raised $1.1M for that company to date.

Tech Entrepreneurship is tough, did you have any mentors along the way?I had many mentors along the way, specifically from incubators and accelerator programs that I participated in – including NewMe (San Francisco), Canopy (Boulder, Colorado), Rev1 Ventures Concept Academy (Columbus, Ohio), The Bixel Exchange (Los Angeles, CA), TechStars (Los Angeles, CA), Brinc (Hong Kong) – very specialized mentors came from each program, and several also invested. Entrepreneurship is constant learning so I am continuously sharpening my skills by keeping the best people around me. I also have a lot of peer mentors and I have advisors on my Board of both companies.

Venture Capitalism is tough, and securing funding for your startup can be a rollercoaster ride. What is the toughest challenge you have faced as a woman in tech? The toughest challenge is being lied to in my face and not reacting. It honestly makes me mad and a part of me wants to speak up, but I don’t want to feed into the stereotype that people who are not familiar or close with Black women have of us. However the fakeness of the VC world is often unbearable.

Awarded $125,000 in the MEDA one million dollar pitch competition

What’s your secret sauce for a perfect pitch?My secret sauce is being clear and concise, using a lot of graphics and images and very few words on my slides, hitting the key points and leading them to ask the right questions by giving them just enough information to spark their interest.

What advice do you have for millennials who want to venture into tech entrepreneurship ? Go for it!! It is hard, you have to put in work and don’t expect handouts from anyone. They say it takes 10 years to be an ‘overnight success’. I have been a full time entrepreneur for 18 years and I have been working on my latest companies for 7- 8 years before we started to gain some real traction. Granted, what I am building is extremely difficult, but nothing comes easy in  life. Just have fun with it and be coachable and open to learn.


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