Bossing It: Ben Gerster on Having a Disciplined and Humble Mindset
Raised with a passion for marketing, Ben Gerster has developed a skill set that powerfully blends creativity with strategic thinking and that now allows him to channel his energy and innovative spirit into a discipline that’s always on the move. In his 20 years in the marketing field, he has evolved from managing accounts to guiding Joybyte's transformation into a specialised force in social media marketing and eCommerce.
A long-proven visionary in the field, Ben has a knack for identifying opportunities where Joybyte can add immense value for clients, helping them drive revenue growth through innovative social media and influencer marketing strategies. He combines a results-focused mindset with a consultative approach, becoming a trusted advisor and partner to his clients.
Ben’s educational background includes degrees in marketing and visual communication design from Arizona State University. In addition to his professional achievements, he’s actively involved in EO Arizona, reflecting his commitment to both business growth and community involvement.
LBB> What was your first experience of leadership?
Ben> My first experience of leadership emerged when I founded my agency right after completing a masters program in graphic design. I hired a few fellow students, marking the first time I was entirely responsible for others' work. This moment underscored the importance of leading with a clear vision for our clients. I had no prior training or experience in leadership, and it was a baptism by fire that shaped my understanding of true leadership.
LBB> How did you figure out what kind of leader you wanted to be – or what kind of leader you didn’t want to be?
Ben> I discovered the leader I didn’t want to be through numerous failures. Initially, I aimed to be everyone’s friend, desiring to be liked, which led to a lack of structure and standards for my team. I saw myself as part of the team rather than the leader setting the standards. This approach turned me into a people pleaser, hindering effective delegation and empowerment. The turning point came when I hired a business coach, a real mentor, who guided me toward the type of leader I aspired to be.
LBB> What experience or moment gave you your biggest lesson in leadership?
Ben> The pivotal lesson in leadership came when I chose to not rescue my team from a challenge, instead empowering them to find the solution. Witnessing their success and the confidence they gained was transformative. It made me realise that my role as a leader is not to solve every problem but to help my team discover their own solutions.
LBB> Did you know you always wanted to take on a leadership role? If so how did you work towards it and if not, when did you start realising that you had it in you?
Ben> I didn’t always know I wanted a leadership role. I did crave control, but my confidence as a leader of others only developed through practice. Leadership wasn’t an innate skill for me; it was learned. Being an entrepreneur thrust me into leadership, forcing me to develop these skills to avoid failure. I recognised my potential when my team sought guidance and vision during challenging times, revealing my ability to lead through adversity with calm, focused execution.
LBB> When it comes to 'leadership' as a skill, how much do you think is a natural part of personality, how much can be taught and learned?
Ben> Natural personality traits can certainly aid in becoming a great leader, but leadership is fundamentally a skill that must be honed. Discipline and a humble mindset are crucial. Even the most naturally gifted leaders must develop the muscles of accountability and emotional intelligence when working with others.
LBB> What are the aspects of leadership that you find most personally challenging? And how do you work through them?
Ben> Delegation remains a significant challenge for me. Trusting others with critical projects is tough. I work through this by allowing others to make mistakes and coaching them toward the desired outcomes, fostering their growth and confidence.
LBB> Have you ever felt like you've failed whilst in charge? How did you address the issue and what did you learn from it?
Ben> Absolutely. As the CEO and visionary of our agency, I take ownership of our failures. Five years in, I realised we were growing in the wrong direction and needed a major pivot. This setback was tough, but I took full responsibility, communicated a clear vision for the way forward, and empowered my team to co-lead the rebuilding process. It taught me the power of transparency, accountability, and shared leadership.
LBB> In terms of leadership and openness, what’s your approach there? Do you think it’s important to be transparent as possible in the service of being authentic? Or is there a value in being careful and considered?
Ben> I believe in being a very open leader. Trust is fundamental, and it stems from a willingness to admit when I’m wrong. Being direct, listening, understanding others, and taking responsibility for decisions are key components of my leadership style.
LBB> As you developed your leadership skills did you have a mentor, if so who were/are they and what have you learned? And on the flip side, do you mentor any aspiring leaders and how do you approach that relationship?
Ben> I’ve had several mentors, ranging from previous bosses to coaches I’ve hired. One pivotal mentor was Russ Perry, who taught me the importance of having a clear vision for my team. My role as CEO is to set that vision and let my team build the solutions. I now mentor aspiring leaders by listening more than talking, asking critical questions that lead to self-discovery rather than providing direct answers.
LBB> In continually changing market circumstances, how do you cope with the responsibility of leading a team through difficult waters?
Ben> I embrace accountability. Leading a team through difficult times means owning the pressure and providing a safe space for decision-making, mistakes, and successes. I involve my team in the process of solution-building while taking responsibility for our collective decisions.
LBB> As a leader, what are some of the ways in which you’ve prioritised diversity and inclusion within your workforce?
Ben> I ensure everyone on our team has a voice. Understanding different perspectives is crucial. If everyone were the same, we’d lack innovation and progress. We thrive on diverse views, opinions, and experiences.
LBB> How important is your company culture to the success of your business? And how have you managed to keep it alive with increases in remote and hybrid working patterns?
Ben> Our culture is the cornerstone of our success. People want to do great work with colleagues they enjoy spending time with. We prioritise people first, separating the work from personal interactions. Celebrating small wins, being real and authentic, and providing support are key. We use tools such as Slack and Zoom to communicate, but the essence behind our communication is what makes an impact.
LBB> What are the most useful resources you’ve found to help you along your leadership journey?
Ben> The EOS framework has been invaluable, helping us democratise leadership within our team and providing a structured playbook for decision-making, problem-solving, and vision setting. As a CEO, external accountability from professional coaches is a game-changer, helping me avoid getting stuck in my own bubble.
