The server came back and said they didn't have Coke.

One of my business partners didn't blink. He skipped Pepsi entirely and ordered iced tea.

I shrugged and took the Pepsi. For me, it was fine.

But that little moment at dinner stuck with me. Because he wasn't choosing a drink. He was choosing a side. Atlanta runs through his veins, and Coke is part of who he is. Pepsi wasn't an alternative. It was a betrayal.

We all do this. You drive a certain car. You wear a certain shoe. You shop at a certain store. Your texts show up as a blue bubble or a green one, and you have feelings about which. These choices go beyond preferences. They shape our identities.

Researchers call it identity-based loyalty — when a brand stops being something you use and becomes something you are. Seth Godin put it simpler: "People like us do things like this." We don't pick brands. We pick tribes.

And here's what's interesting to me. That same force is now running underneath technology.

Are you using Jump or Zocks? Orion or Envestnet? These have become identity choices, not just software decisions. And the plurality is bigger than people admit — you might have one person in the office on Jump and another on Zocks, sitting ten feet apart, both convinced they're ‘right.’

The choice itself isn't problematic. The problem is what happens to everything around it.

Two forces are working against you the moment you commit. The first is status quo bias — we're wired to stick with the familiar and treat any switch as risk, even when the new thing is better. The second is loss aversion — leaving a tool feels like losing something, so the pain of walking away from Orion looms larger than whatever you'd gain by moving to Envestnet.

So you stay. Or worse, you split the difference, and now half the office is on one tool and half on another.

And all of it only matters if your work has a place to compound.

The real question underneath every technology choice is not "which tool is better?" The real question is "where does the value accumulate?" Every decision that doesn't land somewhere permanent — your data, your history, your client relationships — turns the next switch into starting over from zero. Compounding is what makes a choice survivable. Without it, switching becomes a demolition.

This is exactly what I want to open the hood on this Wednesday.

I'm hosting a webinar on choice and AI tools — how advisors should think about the ones they're adopting, and what we're seeing from some of the fastest-growing firms making those calls right now. We'll get into what they're using, how they're thinking about it, and why some choices compound while others quietly cost you.

We'd love to have you join us.

You can sign up here.

Episode 166: This week on Next Mile, Kyle Van Pelt is joined by Dessy Prasad, COO at Northwest Asset Management and RIA Innovations. Dessy began her career at Northwestern Mutual in Seattle as a financial representative on the insurance side, working alongside investment advisors and their teams. She joined Northwest Asset Management 11 years ago and helped support its growing advisor platform and operational infrastructure.

Kyle and Dessy explore how advisory firms can give advisors flexibility without allowing their technology and operations to become fragmented. Dessy shares why the CRM serves as the central hub for their workflows, how her team customizes support around individual practices, and when outsourcing can free advisors to spend more time with clients. They also discuss onboarding, communication, AI note takers, specialized versus general-purpose AI tools, and why cybersecurity and compliance have to be part of every technology decision.

In this episode:

(00:00) - Intro

(01:25) - Dessy’s money moment

(04:11) - From open architecture to architecture with intent

(05:23) - Building a tech ecosystem around a central hub

(06:51) - Customizing workflows without creating chaos

(07:58) - Evaluating AI tools for advisors

(11:35) - When outsourcing starts to make sense

(13:05) - Choosing the right RIA support model

(14:28) - Using communication and workflows to improve execution

(15:57) - Using CRM workflows to keep onboarding on track

(17:01) - How the firm is evaluating AI tools

(19:23) - Dessy's outlook on the future of financial services

(20:41) - Building compliance into technology evaluation

(21:37) - Dessy’s Milemarker Minute

If you would like to arrange a meeting time, please reply to this email, and we’ll schedule something on the calendar.

Jud Mackrill