Dawn Dickson: Serial Entrepreneur

Dawn Dickson is a serial entrepreneur, inventor, and tech innovator who turned high-fashion discomfort (heels!) and physical vending into automated retail and Web3 breakthroughs.

Quick Facts:

Highlights:
  • Founder of Flat Out of Heels and PopCom; inventor of the PopShop Digital vending machine. 
  • First female founder globally to raise over US$1 million via a secure token offering (STO) under Regulation CF. 
  • Raised over $6 million from more than 10,000 investors across her businesses. 
  • Pioneered vending-machine retail solutions with AI & facial detection for data insights.

Formats: Keynote speaker, innovation & tech storyteller, social impact & entrepreneurship mentor (30-60 min).

Audiences: Tech/business leaders, startup founders, women in entrepreneurship, investors, changemakers, those interested in retail innovation, Web3, sustainable real estate.

Outcomes:
  1. Clarity on non-traditional funding paths: equity crowdfunding, STOs, crypto & Web3.
  2. Understanding how to integrate technology (AI, facial detection, autonomous retail) with consumer goods and experiences.
  3. Insights into creating sustainable impact, entrepreneurial resilience, and leveraging diaspora & real estate for global entrepreneurship.
Reviews: (0 reviews)
  • Travels from: Accra, Greater Accra
  • **Fee range: On Request

Talent Services

Keynote Topics:

Dawn discusses how founders and CEOs can withstand economic downturns while maintaining ownership and generating individual financial prosperity. She gives actionable steps to building a successful business that gives you financial freedom and creates generational 

Dawn discusses living and working between the United States and Ghana and how to take the steps to expand your business and life globally.

Dawn discusses her 20+-year journey as a woman in technology and ways for other women to leverage their unique skill sets to design the life and business they have always desired.

Topics include lifestyle design, the importance of self-care, quieting the noise in your life, finding your ‘why’ and staying true to yourself.

Dawn was an early adopter and advocate for the use of blockchain technology in business. She started as a crypto investor which led her to learn how to leverage blockchain technology to raise capital.

In 2019 Dawn became the first female founder to raise over $1M using a security token offering (STO); she discusses how PopCom leverages blockchain for identity management and the use case of selling regulated retail products; Dawn is also a pioneer in the NFT space, incorporating in real life experiences with digital NFTs.

PopCom was the first company to sell physical art that can be minted on the blockchain as an NFT from a vending machine in 2022.

Flat Out of Heels did a successful NFT drop for the 10-year anniversary. In 2020 Dawn was invited to testify before Congress about how Dawn discusses how you can find innovative ways to leverage Web3 technology for your business.

Dawn has won thousands of dollars and secured over $1.5 million in investments from pitch competitions, venture capitalists, and angel investors.

In this workshop or keynote, Dawn takes you step-by-step with key tips, vocabulary, and techniques on how to create the perfect pitch to attract customers and investors. Takeaways will be an editable investor deck template and a vocabulary list.

In this keynote, Dawn discusses the automated retail technology industry and how vending and kiosks are the future of omnichannel retail.

Topics include: how kiosks and vending machines are innovating retail, why omnichannel distribution is important, how small and medium-size companies can compete with Amazon through maximizing omnichannel distribution.

In this keynote or workshop, Dawn takes you through the various ways to secure capital for your business outside of the traditional venture capital or bank route.

This talk focuses on the JOBS Act and SEC Title III Regulation CF and Regulation D rules around raising capital.

Talent Short Bio

Dawn Dickson (also Dawn Dickson-Akpoghene) is an American entrepreneur, inventor, author, and investor whose career has spanned tech, retail, fashion, and real estate. She founded Flat Out of Heels, a roll-flat shoe brand sold via vending to give women portable comfort; and PopCom, a retail technology company integrating AI, facial detection, and automated kiosks.

Dickson blazed trails in equity crowdfunding and Web3, raising over $6 million from thousands of investors, and is recognized for holding the design patent for PopShop, her digital pop-up shop / smart vending machine. She also leads D1 Consulting and has expanded her real estate ventures to Africa, blending sustainable development and cultural impact. Her work has earned numerous awards and media recognition globally.

Dawn Dickson is a serial entrepreneur and inventor with over 20 years of experience in technology and business development. She has founded six successful cash flow positive companies since 2001, including Flat Out of Heels (2011) and PopCom (2017) and has successfully exited one company (Lifestyle Cafe, 2021). She is the first female founder globally to raise over $1M secure token offering under a Reg CF of the JOBS Act. She is considered to be a pioneer in Web3 and equity crowdfunding.

Dawn Dickson has received numerous awards and accolades including being recognized on the inaugural Forbes Next 1000 List, listed among INC Magazine’s 100 top Female Founders, and being named the 2020 OBWS Black Entrepreneur of the Year presented by Snapchat.

Dawn has been featured in countless media outlets including the cover of Black Enterprise magazine, Fortune, Fast Company, Venture Beat, Huff Post, Essence Magazine, and more. Dawn has an expertise in raising traditional and non-traditional business capital, having raised millions of dollars for her ventures since 2001.

In 2019, Dawn Dickson is considered to be a pioneer in the equity crowdfunding space as the first female founder globally to raise a secure token offering (STO) of over $1M using equity crowdfunding, her total as of 2021 exceeds $6M from over 10,000 investors globally.

A recognized leader in entrepreneurship and technology, Dawn was in invited to testify before a Congressional Committee on Small Business in March 2020 in a hearing titled “Building Blocks of Change: The Benefits of Blockchain Technology for Small Businesses”.

Dawn is the winner of the 2020 OBWS Entrepreneur of the Year award, a graduate of the 2019 Nasdaq Milestone Maker program, she was honored as one of the National Urban League Young Professionals ‘Heroes in the Movement’, featured as INC Magazine Top 100 Female Founders, featured in Who’s Who in Black Columbus, Who Who’s in Black Atlanta, and honored as one of Legacy Miami’s Top 40 Under 40 Leaders in South Florida.

Dawn was awarded a design patent in 2020 for her invention of the PopShop Digital pop-up shop, an innovative new vending machine that leverages facial recognition and machine learning technology to capture customer data and insights.

She is a seasoned professional speaker, business advisor, and angel investor. She continues to be recognized as one of the nation’s top retail tech entrepreneurs.

Dawn Dickson travels frequently from her motherland in Ghana to Miami, Florida.

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Talent Videos

Dawn Dickson on Breaking Barriers in Tech, Equity Crowdfunding, and Global Entrepreneurship

Entrepreneur and inventor Dawn Dickson reflects on her journey from early tech jobs to becoming the first Black woman to raise over $1M via equity crowdfunding, adapting retail tech during COVID-19, and building global businesses.

In this video feature, Dawn Dickson is introduced as a trailblazer in entrepreneurship and technology. Recognized as the first Black woman to raise over $1 million through equity crowdfunding, she has become a voice for underrepresented entrepreneurs navigating the challenges of Silicon Valley’s “good old boys club.”

Dickson recalls her early exposure to technology while working in college, where she was tasked with FTP uploading news online during the early days of digital media. This sparked her realization that the future of communication and commerce would be shaped by technology.

She explains how systemic barriers in traditional venture funding pushed her to investigate alternative funding models. Discovering equity crowdfunding, she tapped into community-based investment, creating new opportunities for founders who lacked access to venture capital networks.

The conversation turns to COVID-19 and its impact on her company PopCom. Dickson details how the pandemic forced rapid pivots: moving the supply chain to the United States, redesigning vending machines to be touchless, and integrating kiosks with features like stylus or glove use. She also highlights PopCom’s use of facial recognition to gather anonymous demographic insights, with blockchain employed to address privacy concerns and prevent misuse of personal data.

Looking beyond the U.S., Dickson shares her decision to relocate to Ghana. She urges entrepreneurs not to limit themselves geographically, instead embracing a bicontinental or global mindset when building businesses and sourcing funding.

Throughout, she emphasizes resilience, innovation, and a commitment to creating inclusive opportunities in industries historically dominated by gatekeepers.

Key Moments

00:00 – Introduction: Dawn Dickson as a recognized leader in entrepreneurship and tech.
01:00 – Early influences: mentors and the barriers women before her faced.
02:00 – Breaking Silicon Valley’s exclusivity; discovering equity crowdfunding.
03:30 – Impact of COVID-19: supply chain shifts, touchless vending pivots.
05:00 – Facial recognition, blockchain, and data privacy solutions.
06:30 – Moving to Ghana: bicontinental entrepreneurship and global outlook.
07:30 – Early tech job: uploading news online sparked her interest in tech.
08:30 – Closing reflections: technology as the driver of media and retail.

This video introduces Dawn Dickson, a pioneering entrepreneur who built multiple businesses, raised millions through equity crowdfunding, and innovated retail with smart vending and blockchain technology.

The video offers a concise introduction to Dawn Dickson, highlighting her journey as an entrepreneur, inventor, and investor. She is described as the founder of multiple businesses, most notably Flat Out of Heels, a roll-flat shoe company, and PopCom, a retail technology company focused on automated kiosks and vending.

Dickson’s groundbreaking achievement of becoming the first Black woman to raise over $1 million via equity crowdfunding is emphasized, positioning her as a leader in alternative finance and a role model for underrepresented entrepreneurs. By raising over $6 million to date from thousands of investors, she has demonstrated the power of community-driven funding and the democratization of access to capital.

The video highlights her role as an inventor, holding patents for the PopShop Digital vending machine, which integrates features like facial recognition and blockchain to deliver consumer insights while ensuring data privacy. Her innovation lies not only in technology but in how she combines fashion, retail, and tech into scalable businesses.

Beyond her companies, the video touches on Dickson’s global outlook. She has expanded her entrepreneurial ventures into real estate development in Africa and encourages founders to think beyond borders. Her career reflects a mix of resilience, foresight, and an ability to adapt—qualities that have made her a respected speaker, advisor, and mentor in the fields of tech, retail, and entrepreneurship.

Ultimately, the video positions Dawn Dickson as more than just a business leader—she is a change-maker disrupting systems, pioneering funding models, and creating opportunities for the next generation of entrepreneurs.

Key Moments

00:00 – Introduction: Dawn Dickson’s identity as entrepreneur, inventor, and investor.
00:45 – Founding Flat Out of Heels and PopCom.
01:30 – Milestone: first Black woman to raise $1M via equity crowdfunding.
02:30 – Patents and innovation: smart vending machines with blockchain and AI.
03:30 – Expanding into Africa: real estate and bicontinental entrepreneurship.
04:30 – Closing: Dawn as a role model for resilience, funding innovation, and global impact.

Dawn Dickson shares her journey from early tech experiments to founding PopCom, proving hardware’s potential, and becoming a pioneer in equity crowdfunding and blockchain-based fundraising.

In this talk, Dawn Dickson recounts her first brush with technology as a college student when she was tasked with uploading news to a website via FTP at a time when online news was still in its infancy. That experience sparked her realization that the future of media and business lay in technology.

She describes her entrepreneurial spirit as rooted in a desire to disrupt norms and challenge the status quo. In 2012, she founded PopCom, envisioning a future where vending machines could go far beyond snacks and sodas. At the time, venture capital interest was focused almost exclusively on apps, with hardware dismissed as unattractive. Despite skepticism, Dickson persisted, bootstrapping her business for four years and eventually securing support from friends and angel investors.

Her vision began to take shape when she placed her first vending machine selling rollable shoes (Flat Out of Heels) in Atlanta Airport in 2013. This successful pilot validated her belief that vending technology could be used to deliver retail innovation in high-traffic environments.

She goes on to reflect on her groundbreaking achievements in fundraising. In 2018, she became one of the first founders—and the first Black woman known to have done so—to raise capital through a legally recognized token sale under U.S. regulation. By leveraging blockchain, she effectively offered shares in her company in the form of cryptocurrency, raising over $250,000 early in the campaign.

Dickson stresses that her goal is not merely to be “the first” but to ensure she opens doors for many more entrepreneurs who struggle to access funding. Her approach emphasizes empowerment: encouraging founders to take control of their capital-raising journey, harness technology, and pursue alternative financial pathways.

The video captures her determination to redefine what is possible in hardware, retail, and finance, while inspiring others to challenge outdated perceptions and build innovative solutions.

Key Moments

00:00 – Early tech experience: uploading online news as a student.
01:00 – Founding PopCom in 2012 and facing skepticism about hardware.
02:30 – Concept proof: vending machine in Atlanta Airport selling shoes.
04:00 – Equity crowdfunding and token sales: new funding models.
05:00 – Raising $250,000 through blockchain-based shares.
06:00 – Breaking barriers: becoming the first Black woman to achieve this milestone.
06:30 – Final message: it’s not about being first, but opening doors for the hundredth.

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Talent FAQ's

Technology & innovation, entrepreneurship, automation/retail tech, Web3 & blockchain, raising capital, sustainable real estate, inclusion & impact. 

Yes, she was the first female founder globally to raise over $1M in a secure token offering under Reg CF and has run multiple successful equity crowdfunding campaigns. 

Both. She is U.S. based but has deep operational, investment and real-estate activity in Africa (particularly Ghana & Rwanda)

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