From Startup to Sale: The Leadership Journey of a Creative Agency Owner
An Interview with Steve Osborne of Osborne Pike
If you run a small creative, marketing, or ad agency, you know what it’s like to live in the constant tension of creativity and business. You started because you love the work—but the work is only half the battle. Leadership, growth, team dynamics, and eventually, exit strategy, are what truly shape your agency’s success (and survival).
I recently had the absolute pleasure of sitting down with Steve Osborne, the founder of Osborne Pike, for an incredible conversation on my podcast Business for Humans. Steve built a thriving agency, ran it for 24 years, and then navigated the incredibly difficult journey of stepping away.
I was buzzing for this conversation because, like many of you, I love agency life. I love the energy, the creative leaps, the business challenges, and even the chaos that comes with running an independent firm. Getting to "talk shop" with someone like Steve—who’s been through it all—was an opportunity I couldn’t pass up.
Entrepreneurship: A Leap Into the Unknown
Steve’s career began in an unexpected place: chemistry. With a PhD in hand, he envisioned a future in advertising but found himself drawn to brand design instead. The unpredictability of entrepreneurship was a theme throughout his journey, from transitioning into marketing to founding his own agency.
What stood out to me in our conversation was how his scientific background influenced his perspective on branding. He viewed it not just as an aesthetic exercise but as a deeply psychological one—understanding how packaging, messaging, and design influence consumer behavior. He took calculated risks, balancing strategy with creative instinct, much like an entrepreneur must do when launching and scaling a business.
The Emotional Toll of Leadership
While running Osborne Pike, Steve learned that autonomy—one of the biggest perks of entrepreneurship—can also become its greatest burden. Making every decision, carrying the weight of the company’s future, and navigating the ever-shifting landscape of client needs and industry changes can be exhausting. He shared how he experienced a moment of clarity when he realized that, despite his love for the business, it was time to step away. Burnout had set in, and the cost of staying outweighed the rewards.
This is something I hear often when working with agency owners. The dream of autonomy and freedom can sometimes lead to an overwhelming sense of responsibility. Steve’s journey reinforced the idea that successful leaders not only build businesses—they also know when it’s time to let go.
Building Teams That Outlast You
One of the most fascinating parts of our discussion was how Steve approached succession planning. He understood that leadership isn’t about hoarding decision-making power but about empowering others. He built a management team, gradually stepping back to let them take the reins. But as with all transitions, it wasn’t smooth. When a key creative leader left, it became clear that no plan is foolproof.
What worked? Investing in the right people. Steve found a rare talent—a business development director with the potential to lead the company. He took a leap, and it paid off. The transition wasn’t just about finding someone to replace him; it was about transforming the company’s leadership structure to ensure long-term success.
Knowing When to Walk Away
Perhaps the most profound takeaway from our conversation was the importance of setting a clear exit date. Many agency owners struggle with this decision, lingering in a middle ground of half-in, half-out leadership. Steve made a firm decision: he would step away in June 2024, regardless of the company’s position. That clarity helped guide the transition and ensured the team could adjust to a new leadership structure.
For any business owner contemplating their own exit, this is key: set a timeline. Communicate it. Stick to it. A business can’t move forward if leadership is stuck in uncertainty.
Final Thoughts: The Emotional Intelligence Advantage
Steve’s story is a powerful reminder that leadership isn’t just about making strategic decisions—it’s about understanding people, managing emotions (yours and others), and knowing when to step back. Emotional intelligence isn’t a soft skill; it’s a business-critical one.
If you’re an agency owner or leader navigating a transition, I encourage you to ask yourself:
Am I building a team that can operate without me?
Am I holding onto control out of fear or necessity?
Do I have a clear exit plan that supports both the business and my well-being?
Jaime Gennaro is a seasoned business consultant and coach with 25 years of experience helping companies achieve sustainable growth and leadership success. She has held leadership roles in marketing and operational strategy across various industries, including tech startups and creative agencies. Jaime specializes in business coaching for entrepreneurs and guiding leaders in balancing personal and professional growth. She focuses on reducing burnout, achieving business clarity, and developing entrepreneurial leadership strategies for long-term success.
If you’re facing an exit strategy or leadership transition, visit practica.consulting to book a call.
Leadership doesn’t have to be lonely—share this post and let’s support each other in making better, emotionally intelligent decisions for our businesses and ourselves.
