Leading A Diverse Team as a Serial Entrepreneur
Managing others is one of the most difficult responsibilities of a business owner. How your employees interact with each you, each other, and with customers is the strongest predictor of business success or failure.
Knowing how sensitive it is to manage people in a business context, imagine doing that across multiple businesses. Serial entrepreneur, Chase Chappell, knows a thing or two about leading a diverse team of people to be their best. “Every team has people with different strengths, personalities, and skill sets. The variation between these elements is even wider when you’re talking about a team that is spread across multiple businesses. It’s definitely a challenge to keep all of them happy and bring the best out in them.”
Chappell began as a social media manager, managing a single watch brand. From there he shifted to Facebook advertising. Since then, he has morphed his offerings into an uber-successful ad agency, Chappell Digital. Due to the success of his Facebook advertising, specifically his high return on ad spend (ROAS), his agency gets a consistent supply of clients. Chappell Digital boasts some notable brands among its clientele, Power Crunch and 7-Eleven among them.
Serial entrepreneur Chase Chappell
Chappell is also developing a company that does personal branding for student-athletes to position them for the present and future of NIL (name, image, and likeness). He is also the creator of Sirge.io, an innovative and completely data-driven software that helps ad agencies and marketers of e-commerce businesses with their Facebook and TikTok ad tracking and attribution. Sirge.io was created to address the problems marketers faced after the updates on iOS 14 and 15 made it incredibly difficult to track ads.
As Chappell continues to add to his brand portfolio and hires additional staff, he manages to make it work. “Some of the things I did to keep the engine firing are actually really simple things that anyone with commitment and a strong sense of direction can achieve.”
We’ve curated a few tips from his experience here.
Hire people for their current skill set, nothing more
Hiring people for anything other than the strengths they already have is a bad idea. Of course, the hope and plan are that their strengths become more pronounced with time, and they pick up some other skills and positive personality traits along the way.
Still, every company needs to hire people with clear, functional strengths, and a strong sense of direction so they can hit the ground running from the start. Trying to force new hires into a mold outside their skill set can prove costly—something Chappell has experienced himself. “If the onboarding process takes too long, you could lose vital points to your competition. It should never be assumed by your audience or competitors that your business is slow for whatever reason.
“When we first launched Sirge.io, we had an onboarding issue because the business was growing faster than we envisioned and people were signing up like crazy from the first day. We couldn’t hire and train people fast enough on how to use the software. So, we had to pause our posting on social media for a while to enable us to get our bearings.”
Still, the serial entrepreneur advises that taking a short-term loss — like Sirge.io did by pausing the onboarding of new customers — is better than trying to tough it out when the business is clearly overwhelmed. It will only frustrate and overload your employees and make users see your company as an ineffective option.
Work-life balance is not what you think
People in the workforce are getting burned out and contributing to the employee turnover pool. The need to assign them workloads that allow them time to recharge and focus on their lives outside work was exacerbated after COVID-19. However, Chappell doesn’t believe the answer to an efficient work-life balance is just about creating a flexible work schedule.
“It may not be easy to achieve at first, I mean it wasn’t for me. In the early years, I was working 18-hour days; I basically had no life outside work. But as we continue to invest in growth and refining our software and services, our positive cash flow has afforded us the means to hire more and more people to fill emerging roles within our business model. We’re hiring and training coaches and media buyers at Chappell Digital, and for Sirge, we’re bringing on developers, data engineers, and support staff to keep pushing forward.”
Chappell’s thinking is that you can’t really create an effective or enduring work-life balance for your employees unless you merge the two into your work culture. “The team works hard and plays harder. We do team events all the time, like taking company trips on private jets to pool parties, concerts, traveling to Miami, Vegas, buying gifts for the team and going to events around the US when the team is achieving company goals. We’ve turned our teams into friends. Simply put, we work with people we like to hang out with. Most of our hires have been friends of ours that have the skills to grow our companies. We bring the fun to our work. If we’re going to be working late and burning the midnight oil, we might as well do it with the people we like to hang out with anyways.
Chappell also believes that not having enough of the right staff can muddy the employee experience. “If your company can afford it, hire more capable hands that can fulfill roles with as little supervision as possible. It’s better to have the right culture and skillset fit at a higher cost per employee than it is to have low employee costs with poor culture and skillset fit.”
Help your customers achieve their business goals
Providing customers with the best product or service possible is not enough in a business landscape that’s rife with rivalry; you need to find ways to go above and beyond. “We offer clients ad consultancy and management services via Chappell Digital, and through Sirge.io, we provide them with a technology to streamline, gather, and compare their customer data in a useful way.
But to really seal the deal, we also provide expert and comprehensive Facebook and TikTok ads mastery one-on-one training as well. This boosts the know-how of our clients so that they know what they’re doing from the onset. When they use Sirge, for instance, they’re using it to track well-crafted ad campaigns. When the customer has access to our coaches from our mastery of running ads, it optimizes the benefit they can get from Sirge and also significantly reduces the kind of complaints our support team has to attend to. This gives both your customers and your staff some much-needed peace of mind.”
Chappell refutes the idea that teaching customers how to set up and run perfect ad campaigns on their own will kill business for his ad agency. “From experience, I’ve found that giving consistent value makes your customers trust you more. Besides, most businesspeople love to outsource as much work as possible to cut down costs. We are simply giving them an avenue to be knowledgeable about the subject matter of online ad campaigns, so they can follow along with what we do for them. It keeps us accountable and makes them trust us more because they understand what we’re doing.”
Handling a huge team and brand can be overwhelming, but the strategies highlighted above can can help diverse employees be their best and keep customers satisfied.

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