This Upwork Freelancer Turned Her PowerPoint Making Side-Hustle Into a $1 Million Business. Here’s How She Did It

Courtney Allen, founder of presentation design agency 16X9, is living the millennial dream, traveling the world while raking in $1 million in revenue doing what she loves. What’s grown into a successful business for Courtney, began as a freelance gig selling her expertise in corporate PowerPoint building on the global freelance platform Upwork. There she found a goldmine of clients, including Adobe, P&G, and Home Depot. 

Courtney is one of an estimated 58 million Americans who ditched the boundaries of the traditional 9 to 5 for the freedom, autonomy, and work-from-home flexibility of the gig economy. Using freelance marketplaces like Fiverr and Upwork, creative professionals can hire out their expertise in everything from writing, graphic design, and coding on a project-by-project basis. According to new data from Prudential Financial, a quarter of Gen Z and 28% of Millennial workers hope to parlay their gig work into full-fledged businesses. Courtney has realized that dream and now she’s empowering other ambitious freelancers to live out theirs. 

Today, she employs an executive team of Black women called her “dream team” and an elite group of contractors who create keynote presentations, startup pitch decks, and customized corporate templates for an impressive roster of clients ranging from Fortune 500 to startups. 

ESSENCE caught up with Courtney on a video call from Seoul Korea where the world traveler is working this month. For other freelancers looking to turn their side-hustle into a thriving business, she freely shared the lessons she wished she’d known at the start of her journey and how she successfully scaled her business on Upwork.

If I knew then: Lessons learned on turning your passion into your business.

From the vantage point of hindsight, it’s easy to take a rose-colored view of the entrepreneurial journey. But Courtney makes no pretense about her path to entrepreneurship.  

Initially, the former corporate manager left her role at Cisco with no real plan to speak of. “I just knew I wanted to do something creative, something involving graphic design, and I wanted the freedom to travel,” she told ESSENCE. That year she started a boutique travel agency curating unique, small-group trips to exotic destinations worldwide. While the business produced memorable experiences, it generated little profit. “I was living with my parents, making no money, and racking up credit card debt to get my business off the ground,” she said. 

Eventually, Courtney pivoted her focus in a different, more lucrative direction. During her tenure at Cisco, she discovered she had a niche for designing corporate PowerPoint decks. She began marketing that skill on Upwork where projects began pouring in. The relationships she built on the platform were the springboard for her agency, delivering effective, high-quality presentations for businesses ranging from Fortune 500 to startups.

Despite her happy ending, she is careful not to sell a fairytale to those seeking her advice. The freelancer-turned-entrepreneur says, in retrospect, she could’ve planned a better exit strategy before quitting her job. “There’s nothing wrong with nurturing your passion as a side project and slowly building,” she said. 

How to successfully scale your freelance business.

Scaling a business takes a lot of time and energy, but Courtney says the payoff is well worth the investment. “It took over five years to reach the first $1 million. Then, it took 18 months to go from $1 million to $2 million,” she shared. To help empower other ambitious freelancers to live out their dreams, she offers the following four steps she took to grow 16X9 into a seven-figure company:

Step 1: Build capacity.

I built an agency to increase capacity. My dream team at 16X9 is spread across three continents to enable a follow-the-sun approach and provide truly on-demand presentation design services. Along with designers, a traffic coordinator and PMs are ready to handle any requests.

Step 2: Set clear expectations.

I send a proposal to all new clients for written approval. This details the scope, timeline, budget, and when rush rates are applied so that there’s absolute clarity surrounding project expectations. I update when we’ve approached 50% and 75% of the allotted hours and budget.

Step 3: Track progress and timelines.

I keep detailed monthly records and metrics. Underestimating projects was my top unrecoverable cost. We can quickly and accurately estimate most projects using Harvest, a time-tracking and reporting application, combined with building out a rate sheet and an Excel cost calculator.

Step 4: Build relationships.

I nurture client relationships. I’ve had some clients on Upwork for upwards of six years. I talk to them personally and show my appreciation where I can. And in turn, they spread the word to their colleagues and other departments and even take us with them to new jobs.