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March 28, 2025 22 mins

Are you tiptoeing around what really needs to be said?

In this episode of Don’t Do That, Jason Early, CEO and founder of RISR, joins Kelly Waltrich to talk about why tough conversations are so important. “Bad news doesn’t get better with time,” Jason points out, and saying the thing that needs to be said often leads to breakthrough moments.

During the episode, Jason highlights the growing industry challenge that led him to found RISR, shares his approach to recruiting and hiring, and explains the importance of assuming positive intent during difficult discussions.

Kelly and Jason cover:

 01:25 Why advisors need better tools for serving business owners
 05:20 The demographic tidal wave of business owners retiring
 07:10 The increasing popularity of private company ownership
 07:50 Why advisors are rapidly adopting the RISR platform
 09:30 Jason's "Don't Do That" – stop avoiding tough conversations
 10:33 The value of saying what you think you can’t say
 12:02 How Jason and his team cultivate a culture of transparent communication at RISR
 12:24 The value of assuming positive intent during uncomfortable conversations
 15:39 Jason's approach to recruiting and hiring
 16:44 The importance of relationship-building in talent acquisition
 19:58 Implementing frameworks to balance gut instincts with strategic decision-making


Connect with Kelly Waltrich: 


Connect with Jason Early


About Our Guest:

Jason is the Founder & CEO of RISR and has spent his entire career in financial services solving problems for financial advisors. RISR has been named by Investment News “Best new technology” and Jason as one of their “40 under 40”. He started his career with an advisory firm in Philadelphia where he spent seven years as a Managing Director. From there he joined an e-learning & consulting firm and prior to founding RISR, he was the President of a leading wealth tech firm that pioneered private company valuation services. He is a former alumni advisory board member of the American College of Financial Services, and board chair of the Brian H. Early Foundation. He and his wife Molly are most proud of their daughter, Isla. 



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