Craig Iskowitz, CEO of Ezra Group, returns to speak with Jason about navigating the overwhelming pace of technology change in wealth management. Iskowitz explains how Ezra Group provides objective tech stack evaluations for firms without the bias of referral fees or software sales. The discussion highlights the shift from crypto to AI hype, the dangers of overbuilding in-house tools, and why "integration quality" is often the weakest link in an advisor's workflow.

This episode is a must-listen for RIA owners and operations leaders who need a reality check on AI implementation and a framework for building a scalable, well-integrated tech stack.

Episode Highlights:

00:00 Milestone Guest Intro

01:23 Craig’s Origin Story

02:51 Tech Change Goes Exponential

04:31 AI Hype Versus Reality

08:03 Regulated Industry Limits

09:28 Buy Versus Build Returns

10:01 Hidden Costs of Building

15:43 When Building Makes Sense

18:22 Super Apps and All-in-One

20:01 Integration Friction Problem

20:43 Integration Reality Check

22:48 AI And Vendor Shifts

26:51 Note Takers Threaten CRMs

29:19 Build Versus Buy Limits

30:49 Tech Spend And Stack Strategy

32:13 Optimize Before Replacing

34:53 Wishes Hiring And Motivation

39:35 Wrap Up And Credits

Resources:

Facebook – Jason Pereira's Facebook

LinkedIn – Jason Pereira's LinkedIn

Woodgate.com – Sponsor

Ezra Group

LinkedIn - Craig Iskowitz’s LinkedIn

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