Meet Tommy Oliver of Rollin Hero Staffing

Today we’d like to introduce you to Tommy Oliver.

Hi Tommy, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I started Rollin Hero Staffing in 2015 with a simple but ambitious goal to work for myself while helping my friends in the film industry find flexible, well-paid work that allowed them to continue auditioning and pursuing their careers. What began as a lean operation grew quickly, largely because I focused on showing up, doing the work, and building real relationships without transactional expectations.

By 2017, we were staffing for nearly every major catering company in Los Angeles, which eventually led us to expand into party rentals. Each year, however, brought increasing challenges, stricter regulations, higher taxes, and more complex compliance requirements. If not for long-standing business relationships in St. Louis, Missouri, the company likely would not have survived its first EDD audit.

Even before COVID, policy changes such as AB5 posed serious challenges to the event and staffing industries. In 2019, at the peak of our growth in Los Angeles, we had a buyer prepared to acquire the company outright. That opportunity disappeared in 2020 when the pandemic shut the industry down.

In response, I sold off the party rental division, relocated to Florida, and began rebuilding the company by expanding into states with labor laws better aligned with our business model. Today, Rollin Hero operates in six states. Notably, the combined workers’ compensation costs in the five states outside California are roughly half of what we pay in California alone.

Leaving Los Angeles was never the plan, but it became a financial necessity to protect our leadership team, many of whom have families, and to keep our staff employed. Despite those efforts, the 2025 Los Angeles fires devastated our largest market, resulting in the loss of approximately 50% of our clientele. Similar to COVID, meaningful relief was limited. Because we are not a brick-and-mortar business, we did not qualify for SBA assistance.

After spending five years recovering from the pandemic, we are once again navigating a crisis that disproportionately impacts small businesses. That is where we are at right now.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
No, it has not been a smooth road. The biggest challenges have consistently come from government overreach and one-size-fits-all policies that don’t reflect how small, service-based businesses actually operate. Regulations intended for large corporations are often applied uniformly, creating disproportionate costs and administrative burdens for smaller companies.

COVID was a major inflection point, followed by the 2025 Los Angeles fires, both of which significantly reduced demand in our largest market with limited relief available to non–brick-and-mortar businesses. At the same time, rising and largely unregulated insurance costs, particularly workers’ compensation, along with mandated healthcare and retirement requirements that temporary staff would not typically qualify for in other states, placed additional strain on the business.

These pressures were compounded by the rising cost of living, fuel, and operating expenses in California. Each challenge forced us to adapt, restructure, and expand into new markets simply to remain viable.

Alright, so let’s switch gears a bit and talk business. What should we know?
Rollin Hero Staffing is a multi-state staffing company specializing in event, hospitality, and production support. We provide highly reliable, well-trained staff for catering companies, private events, film and television productions, and large-scale activations. Our team is built to step into fast-paced environments and perform immediately.

What sets us apart is our people-first approach and operational discipline. We don’t just place bodies on jobs we build relationships, show up consistently, and take accountability seriously. Many staffing companies rely heavily on churn; we focus on retention, reliability, and clear communication with both clients and staff.

Brand-wise, I’m most proud of our resilience and reputation. Despite operating through COVID, regulatory upheaval, and natural disasters, Rollin Hero continues to operate in six states while maintaining consistent standards across every market. We’ve proven that it’s possible to scale without sacrificing integrity or culture.

I want readers to know that Rollin Hero is a company built by and for working professionals. We understand the realities of flexible labor because we come from the industries we serve. A lot of app based staffing businesses have tech and business people finding staff to find staff. You have to work banquets, to understand banquets.

What sort of changes are you expecting over the next 5-10 years?
Staffing agencies like mine will inevitably be reshaped by technology. We already use AI to streamline administrative and clerical work, but building fully automated staffing systems is extraordinarily expensive and often overlooks the most important element of this business: people.

Staffing is still a relationship-driven industry. People-to-people communication, industry knowledge, and situational judgment are difficult to replicate with app-based platforms. What I’ve seen firsthand is that speed and automation often come at the expense of quality. Many app-based agencies prioritize rapid placement over skill, experience, and fit, resulting in lower-caliber staff with little understanding of the work, despite costs remaining largely the same for clients.

The future of staffing shouldn’t be purely transactional. The real opportunity lies in systems that combine smart technology with experienced industry professionals who understand the nuances of events, production, and hospitality, and who actively communicate with their clients. However, that’s not cost effective in major cities like Los Angeles because of the government regulations.

Contact Info:

• Website: https://www.rollinherostaffing.com
• Instagram: https://www.instagram.com/rollinhero/?hl=en