Inside an Agency Mastermind

    CQ

    Corey Quinn

    Founder, Deep Specialization™

    An interview with Jon Tsourakis, Owner of Digital Mastermind

    "Our philosophy at Digital Mastermind, an agency leadership group, is that a rising tide lifts all boats." –– Jon Tsourakis, Owner, Digital Mastermind Group

    (🎙️ listen now)

    The agency landscape is extremely competitive across most verticals - some might prefer to gatekeep insights around best practices and growth levers to maintain an edge. That’s not the case at all for today’s guest, Jon Tsourakis. 

    Jon is a long-time agency owner and entrepreneur who steadfastly believes in the power of peer knowledge. As the owner of an agency leadership group, he knows that the secret sauce to success is sharing what works, what doesn’t, and how to navigate typical agency scaling challenges.

    Jon joins The Deep Specialization Podcast to share everything he’s learned as an agency owner and while running the Digital Mastermind Group. This peer leadership association brings over a hundred agency owners together for support, learning, and knowledge-sharing.

     

    We cover in this episode:

    • The benefits of peer groups like Digital Mastermind.

    • Typical challenges agency leaders face.

    • Jon’s journey as a website agency founder and major milestones.

    • Jon’s approach to outbound and inbound, as well as the secrets to unlocking client budgets.

    Actionable takeaways for agency founders:

    • Smaller agencies can make faster bets on innovation, and larger agencies can learn from that.

    • There’s power in sharing what works for your agency and what doesn’t; rising tides lift all boats.

    • You can scale talent through partnerships, it doesn’t always need to be through hiring.

    • People can sniff AI outreach a mile away, so make sure you write with intention.

    🎧 Listen to the episode now:

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    Best,

    CQ

     

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    About Corey Quinn

    Founder, Deep Specialization™

    Corey helps founder-led agencies scale through Deep Specialization™ and programmatic M&A. Former CMO of Scorpion ($20M to $200M). Author of "Anyone, Not Everyone."

    “Is this a good fit for my agency?”

    I partner with founders who want to build something meaningful, not just a busier agency, but a stronger, more scalable business.

    You’re likely a strong fit if:

    • You’re generating $1M–$20M+ annually
    • You want to lead your market, not blend into it
    • You’re thinking about long-term scale, not short-term tactics
    • You want a growth engine that doesn’t rely on you
    • You value clarity over complexity
    • You’re open to advanced growth levers, including acquisitions
    Anyone Not Everyone Book Cover

    Escape Founder-Led Sales With My Free Book

    My bestselling book Anyone Not Everyone reveals the positioning and outbound system that helps founder-led agencies create predictable, scalable growth.

    Endorsed by Aaron Ross, Alan Dibb, Dr. Benjamin Hardy, and many other top thinkers in the agency world.

    ★★★★★
    Over 100 5-star Amazon reviews