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In this episode of Life’s a Pitch, I sit down with John Tsourakis, co-owner of digital agency OYOVA and a multi-time founder who has built, scaled, and exited businesses across agencies, healthcare, and tech. We get into what it really looks like to run an agency today, why the model is tough, where founders get it wrong, and how acquisitions and focus can create leverage instead of more chaos. John shares unfiltered stories about bad clients, setting hard boundaries to protect your team, and the leadership moments that cost money but save culture. We also talk sales the honest way, including cold calling, rejection, why doing the opposite of what gurus recommend often works, and how to stay sharp without burning yourself out. We also dig into founder mindset, letting go of failures, knowing when to sprint versus recharge, and why resilience matters more than raw hustle over the long run. You’ll learn: ✅ Why the traditional agency model is under pressure ✅ How to spot and walk away from nightmare clients early ✅ What still works in sales when everyone is chasing digital tactics ✅ How strong boundaries create better teams and better businesses ✅ Why letting go is a real competitive advantage If you’re building or running an agency, leading a sales-driven business, or navigating growth with real people and real pressure, this episode offers an honest look at the realities most founders don’t talk about. Connect with Jon Tsourakis Guest LinkedIn: / jontsourakis Guest Website: https://www.oyova.com/ If you are a B2B company that wants to build a real, repeatable executive content engine instead of chasing random posts or outsourcing your voice to a generic agency, Outworks may be a fit for you. Everything you see in our podcast and content is built through founder-led strategy, tight systems, and an AI-powered content infrastructure designed to scale without losing your voice. Learn more about services here: https://www.outworks.io