Darien Dash Discusses The Unique Challenges Start-Up Investors Face

Darien Dash is a long-time innovator and disrupter in the tech space. With experience ranging from the music industry to digital marketing and strategic business management for athletes and entertainers among other types of clients, Dash used his music and entertainment background as a springboard for his numerous other entrepreneurial endeavors.

Today’s entrepreneur can find all manner of business advice from investors, past founders, business advisors, and other players in the startup ecosystem. But when Darien Dash began his journey to entrepreneurship, he didn’t have a road map and went from working out of the home to going public in the span of half a decade.

From Hip Hop to an Early Internet Pioneer

Darien Dash always had an entrepreneurial spirit, and it was kindled in the early-mid 1990s with the formation of his first two businesses at a young age. Inspired by reading John Naisbitt’s 1982 book Megatrends in his senior year at the University of Southern California, Dash had an inkling that he wanted to go into tech but wasn’t sure how to get there yet or what type of problems he wanted to solve with technology solutions that were currently on the market. So he founded Roc-A-Bloc Records with his cousin Damon J. while he was still in college, the two talked it over at a Heavy D launch party and decided that they had the potential for a successful business venture together by making use of their contacts in the music industry and Dash’s family background in the entertainment business in New York.

Roc-A-Bloc was certainly successful in that the label signed then up-and-coming Jay-Z within two years of commencing, grossing more than $100,000 in record sales prior to Jay-Z skyrocketing to superstardom and becoming a mogul on his own. But despite the success of Roc-A-Bloc and his connections within the entertainment business, Dash was dissatisfied with where his life was headed. He realized that tech offered more potential firepower for his aspirational visions. Megatrends accurately predicted that technology would become the major wealth driver of society within decades, opposed to the captains of industry, but just shy of 15 years after the book’s initial publication, Dash had other ideas.

Damon J. went on to form Roc-A-Fella Records after Jay-Z took the label to new heights, and Dash parted ways with them to focus on how he could work with computers at a time when the Internet was young and only beginning to take hold on society. Upon graduating from USC in 1994, Dash formed his own company, DME Interactive Holdings, which strove to provide more professional and educational opportunities to urban communities with hardware, software, and Internet access.

Given that 5 million Americans had Internet access in 1994, compared to only about 10% of Americans not using the Internet today, Dash sought to become a change agent long before the Internet would become such a ubiquitous part of commerce, communications, and culture. By 1999, DME Interactive had gained a massive foothold in the tech sector and was the first Black-owned company to become publicly-traded on NYSE. Darien Dash then collaborated with President Clinton and to improve Internet access in minority communities, and while doing so, partnered with Carly Fiorina who was then CEO of Hewlett-Packard to create their Places of Color program that would provide low-cost computers to disadvantaged communities in the New York City area. Having grown up in impoverished Black and Hispanic communities where the Clinton administration wanted to improve technological parity, Dash testified in front of Congress on how to improve Internet access and close the technology gap in underserved communities. Drawing on his background in hip hop and the entertainment business, Dash decided to get famous rappers like Jay-Z and Puff Daddy to make computers and technology in general more palatable to the average user and minorities, opposed to specific niches of tech-savvy middle-class whites. Dash worked with AT&T to bridge this digital gap and get more minority households to access the Internet in the 1990s.

20 years since his massive success with DME Interactive, Darien Dash became the CEO of The Movement Management advisory firm founded in 2015, in addition to currently holding director positions with Dunkin Donuts Franchise Growth Partners and 414 Media Advisors. In addition to his advisory work in sports, entertainment, and media, Dash was also one of the first entrepreneurs to heavily invest in legal cannabis and CBD products before the industry exploded.

Darien Dash’s Rocky Road to Success and What Today’s Startup Founders Can Learn From Him

While Darien Dash’s success is certainly impressive, he encountered several challenges. The 1990s were a radically different time as far as both technology and entrepreneurship were concerned, and there weren’t as many resources for both as there are today.

Despite these disparities, there are many lessons to be had from Darien Dash’s entrepreneurship journey spanning three decades, and advice for startups to glean from them.

You Could Be Able to Get Your Idea Off the Ground Without an Investor…

It’s said that VCs are hoarding about $120 billion in cash, but only about 34% of startups are receiving Round A funding. About 1,500 startups per year get picked by VCs, with another 50,000 funded by angel investors, relative to the hundreds of thousands of proposals that reach their desks.

Darien Dash self-funded DME Interactive for four and a half years until the company went public in 1999.

Today, going public is less of a be-all-end-all compared to prior decades. Firms often receive several rounds of venture capital while remaining privately held, making IPO exit strategies less common for professional investors. But Dash never had angel investors or venture capitalists: he was incredibly broke for years so he could self-fund all the way until DME Interactive became sustainable and successful enough without him having to constantly pour his money into the company.

While this path is extremely difficult and requires sacrifices on both business and personal levels, the tradeoff is that you get to build your career and company trajectory however you choose. Another avenue to explore is co-selling, a partnering process in which two or more peer-level providers with complementary offerings collaborate to provide a holistic solution that meets a shared customer need.

…if You Have the Right Supports in Place

Dash was married to a woman who was willing and able to pay the bills while he focused on entrepreneurship. There is no shame in having a spouse, parent, friend, or other family member paying for your support while you focus on building your business. However, in addition to giving them the credit, they’re due, you should determine how you will support yourself and your company while you build your company. If you have a family to support, talk with your spouse about how you will handle caregiving and financial support equitably.

If you do not have this as an option, take advantage of the expectation to work remotely right now. Pursue different funding sources from the SBA and any state and local programs to get additional funding so you can free up your personal funds to focus solely on your startup.

Make the Most of Isolation Due to Coronavirus

Entrepreneurship can be lonely. The average person doesn’t understand why founders do what they do, why they would take risks in starting their own venture instead of just getting a job, and working on their passion on the side. But even if you’ve found a supportive community in the startup sphere, it’s impossible to get together now for those Meetup groups and happy hours to talk business and life because of COVID-19 related lockdowns.

It’s a difficult time for everyone right now, and social distancing can take a real, literal toll on your mind and body. But the bright side is that there’s no better time to go all-in on your business venture because you literally can’t go out.

Darien Dash described his initial jump into entrepreneurship as “barely leaving the house for seven months”. That sounds unthinkable in 1995 terms, but is now a fact of life 2020 as we must practice social distancing for our own safety and that of our communities. Right now, no one is expecting you to be able to have a social life, a professional life outside the home, or even have stellar finances. This makes it the ideal time to test new methods and product design, connect with investors and other entrepreneurs on social media and digital events, and read. In Dash’s own words in this interview with Entrepreneur Mindz,

“Like I basically didn’t come outside, unless it was to  talk to somebody or hang out. I didn’t come outside; I stayed in the house and read every day. And all I would do is just read about the business and read about what was going on and put together and formulate my understanding of where we were and where we were going. And once I was able to truly do that and marry it to my mission, that’s when I came out and decided what I wanted to do with my company.” 

Take the time to read success and failure stories from other entrepreneurs. Read about what is happening in the world and industry, and see what kind of opportunities you can glean from problems people are having right now. You may end up pivoting to a completely different industry from your first venture as Dash did.

Even Darien Dash Made Mistakes, Learn From Them and Look to the Future

DME Interactive was ahead of its time in terms of creating interactive content with major artists, and AOL news features that would be of interest to minority communities that would make them want to use computers. But the problem he encountered was that people couldn’t actually access the content because they lacked the technology for it. This led Dash to begin the Places of Color program that led to cheaper computers.

Dash used this mistake to correct the glaring problem that got overlooked and to always think about the future. We may not have Twitter, YouTube, and TikTok today if it wasn’t for DME’s enhanced CDs.

Follow Darien on Twitter @DarienDash


Article Editor

Pamela is a television journalist, humor writer and novelist. Her first novel, Allegedly, was released in 2015 by St. Martin’s Press. The book is available on Amazon and Barnes & Noble. She and her husband, Daniel, have a 3-year-old son, Carter.

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