CWC 95: Evolving as your agency grows (featuring Jason Swenk)


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Oct 18 2023 26 mins  

In this episode, Chip talks with Jason Swenk of Agency Mastery 360 about the intricate dynamics of agency growth, operations, and sales. The discussion touches upon multiple challenges that agency owners grapple with daily, offering a number of actionable insights.



  • The Accidental Agency Owner: Jason himself began as an accidental agency owner at 22 when he designed a website poking fun at the pop band, NSYNC. From there, he scaled to an eight-figure agency with over 100 employees before selling. The “accidental” trajectory resonates with many in the agency world, leading to unique challenges and growth patterns.

  • The Importance of Clarity: Jason emphasizes that clarity is paramount for agency success. Many agencies fall into the trap of accepting any client that comes their way, diluting their niche and expertise. By clearly understanding the direction they want to take, agencies can build a robust framework and delegate more efficiently.

  • The Agency CEO Role: The transition from owner to CEO is vital for growth. A CEO needs to set the vision, coach the leadership team, be the organization’s face, build strategic relationships, and understand essential financial metrics.

  • To Sell or Not to Sell: When contemplating selling their agency, owners need to assess the motivation behind this decision. Whether it’s discontentment, wanting a change, or a genuine need for cash, understanding the core reason can make the process more seamless. Jason sheds light on valuation nuances, stressing the importance of EBITDA and the pitfalls of earnouts.

  • Enhancing Sales and Lead Generation: One of the primary pain points for agency owners is sales. Jason recommends a multi-channel approach, which includes inbound and outbound strategies.


Chip and Jason highlight the importance of evolving with the agency. Whether it’s adjusting the business model, understanding financial metrics, or pivoting strategies, staying proactive ensures sustained growth and success.


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