74: Serial Entrepreneur Dawn Dickson On How to Launch Like a Boss

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74: Serial Entrepreneur Dawn Dickson On How to Launch Like a Boss

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Today on the show, we have a real boss. Her name is Dawn Dickson and she is a serial entrepreneur with over 16 years of experience in marketing and business development. She has launched four successful cash flow positive companies since 2002. Her most recent ventures are Flat Out of Heels (which provides rollable flats for women) and Solutions Vending International, recently renamed Pop Com, which provides a software solution to make vending machines more intelligent.

Dawn has received numerous awards and accolades for her Business savvy and pitching skills, including being awarded First place in the PowerMoves NOLA Big Break pitch Competition and second place in the 2016 SBA InnovateHer Challenge.

Additionally, Dawn was selected to participate in some of the nation’s top accelerator programs for entrepreneurs including the NewME(San Francisco),Canopy Boulder (Boulder,Colorado) and Techstars (Los Angeles).

On today’s episode, Dawn gets into:

  • How she went from living her best life with her first business to broke and moving in with her cousin
  • How she lost $15,000 attempting to start Solutions Vending
  • How she became a pitching queen
  • And Her best kept secret to find amazing business partners

Listen on Apple Podcasts, Soundcloud, Stitcher and Google Play

Links mentioned on this episode

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Social Media Info

Connect on Instagram:

Dawn Dickson – @dawnwdickson

Flat Out of Heels – @FlatOutofHeels

Side Hustle Pro – @sidehustlepro


Meet the host:

Nicaila Matthews-Okome

Hi! I’m Nicaila, the Creator and Host of the Side Hustle Pro Podcast. I started Side Hustle Pro when I was a side hustler myself. I was a digital marketer at NPR by day, side hustler by night. Through the powerful stories shared on this show and the courage to launch my own initiatives, I was able to quit my own job and go full time with Side Hustle Pro.

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201: I QUIT my Job! (REWIND)


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