Bonus Episode, with Elliott Holland

What if the automation tools you rely on are actually keeping you from connecting with your best clients? Are you curating your pipeline—or just letting technology filter everyone for you?

This episode challenges brokers and advisors to rethink the role of tech in deal-making. True success isn’t about scaling outreach indiscriminately or relying on “automation slop”—it’s about intentionality, personalization, and understanding the game you’re actually playing. Instead of defaulting to mass-market tactics, the conversation is a call to focus on quality over quantity, clarity in outcomes, and aligning your process with the clients who truly value what you offer.

Special guest Elliot joins Jason Cutter for an unfiltered, honest discussion about what brokers must do to thrive in the evolving M&A landscape. From provocative marketing that filters for fit, to the pitfalls of over-automating client interactions, Elliot shares real lessons learned and actionable strategies for elevating your approach. He explores the growing sophistication of buyers, the changing nature of broker competition, and why scaling the “unscalable” is the future of true advisory work.

Subscribe for more actionable perspectives on building your deal flow—and share this episode with fellow brokers ready to replace hope with high standards, personalization, and proactive pipeline engineering.

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