From Startup to Sale: The Leadership Journey of a Creative Agency Owner: An Interview with Steve Osborne

In this episode of Business for Humans, Jaime Gennaro sits down with Steve Osborne, founder of Osborne Pike, to discuss his journey from launching a creative agency to successfully exiting after 24 years. Steve shares hard-won leadership lessons and the unexpected challenges of scaling and then exiting.

🚀 What You’ll Learn in This Episode: ✔️ The realities of growing and exiting a creative agency – and what most founders overlook ✔️ The toughest decisions agency owners face (including hiring, delegation, and restructuring) ✔️ Why politics and leadership dynamics inside agencies can determine long-term success ✔️ The role of business development in sustaining growth – and why many agencies get it wrong ✔️ How Steve knew it was time to step away and what he learned from the transition

Whether you’re scaling your agency, thinking about an exit, or looking for smarter leadership strategies, this episode delivers real-world insights you can apply right now.

🎧 Listen now and learn how to navigate the highs and lows of agency leadership with confidence.

👉 Need help with an exit strategy or agency consulting? Visit practica.consulting/contact to book a call.

📢 If you found this episode valuable, leave a review and share it with other agency leaders!

Jaime Bancroft-Gennaro helps leaders and entrepreneurs grow sustainable, purpose-driven businesses with clarity, strategy, and human-centered leadership. As a business coach, consultant, and author, Jaime is passionate about guiding professionals to scale their businesses with intention—without burnout. With a background in high-growth companies and leadership development, Jaime specializes in aligning vision with actionable strategies that drive meaningful, lasting success.

Jaime’s upcoming book, Grounded: A 30-Day Guide to Feeling Whole Again, serves as a roadmap for leaders and professionals looking to reconnect with their purpose, prevent burnout, and build momentum in their careers and businesses.

Join her community for insights on growth, leadership, and personal transformation. Sign up for our weekly newsletter at http://practica.consulting.

Podcast music by: Luca Gennaro