Journalism once seemed like the safe bet.You got influence. Access. A real voice in the room. But by the late 2010s, the industry’s foundations were beginning to crack.Newsrooms were shrinking fast. Ashley M. Williams saw it coming, but she also spotted something else hiding in the chaos.
She wasn’t short on stories. She realised the industry lacked the structure to help creators monetise them. As a journalist and producer, Williams noticed a weird disconnect. Talented creators had great narratives but no tech or support to package them. Brands were desperate for authentic content for Millennials and Gen Z but couldn’t find the right people to make it. The opportunity wasn’t just making more journalism. It was building a bridge. Connect creators with brands willing to pay for their work.
Williams could have kept climbing the media ladder. She didn’t. She quit. She started RIZZARR. It was a gamble. A big one.
Walking away from a stable paycheck is terrifying when your business model is still a guess. Williams initially imagined RIZZARR as a hybrid: part news site, part social network. A place for young people to publish, build an audience, and create impact. The vision was compelling, but the business had no clear path to revenue.
The pressure was real. She took a weekend job. Her family chipped in some cash. But customers were slow to come. Fundraising was slower. She went back to side hustles just to keep the lights on. It took years—actual years—to land the first paying customer.
She didn’t have an established network of tech founders. She lacked entrepreneurial experience. According to the Small Business Administration, Traction remained elusive. So she built it brick by brick.
She entered the Harvard Business School African American Student Union’s Black New Venture Competition. Second place. That helped. She joined a government-backed entrepreneurship program in Virginia. Learned the basics. She incorporated. Got her tax ID. Opened a bank account. She found mentors through SCORE who helped her validate the concept and figure out hiring. And she kept doing contract work. It paid the bills and, unexpectedly, opened doors to corporate clients.
Then, the break.
In 2017, a temp role at a national medical company turned into a substantial contract for RIZZARR. Finally, she had the financial breathing room to go all-in. The model shifted. The “social network” idea died. In its place rose a commercial marketplace. Brands commissioned content. Creators got paid.
By 2017, RIZZARR had 4,700 creators. By 2020, roughly 5,400. Revenue hit over $50,000. Clients included JPMorgan, the American Heart Association, and Centene. In 2023, they joined the Comcast NBCUniversal SportsTech Accelerator. They ran proofs of concept with NBC Sports. Started a paid pilot with GolfNow. Today, RIZZARR is a content-intelligence platform. It uses data, sentiment analysis, and AI to help brands plan creator-led content.
How She Decides
Williams operates by three rules.
1. Let transactions correct the strategy.
A business plan is just a theory. Customers are the proof. “The market always speaks for itself,” Williams says. “Then you adjust.” RIZZARR didn’t stay an inspirational news hub because the market pulled it toward paid transactions. That wasn’t a rebrand. It was survival.
2. Use small proofs to reduce large risks.
You never have total certainty. So look for breadcrumbs. Second place at Harvard? A breadcrumb. It showed outsiders understood the idea. The entrepreneurship program? Practical knowledge. Family funding? Early capital. SCORE mentors? Critical feedback. Contract work? Income and access. None of these guaranteed success. But together, they gave Williams enough courage to take the next step. It’s not about reckless leaps. It’s about gathering enough evidence to justify a controlled move.
3. Experts advise; founders decide.
“Even ‘experts’ get it wrong,” Williams admits. “No one knows everything.” After Harvard, an angel investor showed interest. It looked perfect on paper. Validation plus cash. But they didn’t share the same vision. Williams walked away. She didn’t stop listening to mentors or lawyers. But she stopped treating their advice as orders. She used their expertise as input, not instruction. She kept strategic control.
That failed angel investment was a gift. It taught her that money can kill a company if the mission isn’t aligned. She realized she’d brought the wrong people into the fold. People who hadn’t built successful companies themselves. So she changed her approach. She replaced opinion with market testing. She sought specialized support (like TechTown Detroit and Startup@BerkeleyLaw) instead of generic advice. And she protected her strategic alignment fiercely. Early funding isn’t always good funding.
The Network
Williams didn’t build RIZZARR on celebrity investors. She built it on access. Her family provided the initial runway. SCORE mentors helped refine the mission and landed that first crucial client. TechTown expanded her network. Christopher Peters, her CTO, brought the technical heavy lifting from his time at Zapier. Supporters like Code2040, Wilson Sonsini, and Comcast added layers of legal knowledge, credibility, and enterprise access. It’s not one powerful backer. It’s a system. Each relationship solves a specific problem. Together, they power the marketplace.
The Ladder
If you’re thinking of leaving your safe job to build something, don’t just jump. Test it. Williams’ journey offers a ladder:
Gate 1: Interview 10 potential creators.
Gate 2: Interview 10 potential paying customers.
Gate 3: Secure three written pilot commitments.
Gate 4: Complete one paid transaction.
Only then do you leap.