My youngest daughter has been counting down to the last week of August. School starting has nothing to do with it. There isn’t a sporting event driving her anticipation. No, her season kicks off when the design on the disposable coffee cups change, and she has been talking about it in the kitchen for two weeks straight.

I am not a pumpkin spice guy, so this changing of the drink menu has never been something to watch. I have never seen her excited about a cup of coffee which made me curious enough to go look at how this happened.

Starbucks brought the PSL back nationwide on Tuesday. They announced the date three weeks ahead, because the announcement is part of the product. It runs until the winter holiday menu takes over in early November, and then it's gone until next August.

Here's the part I didn't know.

In the spring of 2003, a small team was asked to find the next fall drink. They started with a hundred ideas and cut it to ten. The pumpkin latte came in last on that list of ten, with middling purchase intent scores. They nearly called it the Fall Harvest Latte, which sounds like something you drink out of obligation.

They tested it that October in about a hundred stores in Vancouver and Washington, DC. It separated from everything else immediately.

Of course, the pumpkin is not the star of the show. Pumpkin is a pretty mild flavor. The cinnamon and the nutmeg and the clove do the work, and those spices were already sitting in every pantry in America. They didn’t invent anything. They took something familiar and time boxed it’s delivery.

Hundreds of millions of drinks later, pumpkin spice is a category of its own. Bagels, cereal, candles, dog treats. Someone made pumpkin spice Spam. One firm puts the products market at $1.25 billion last year, heading toward $2.8 billion over the next decade. All of it out of a bottom-of-the-list idea built from espresso and milk they were already selling.

The thing they actually built was a season.

Sit with the two names for a second. Fall Harvest Latte. Pumpkin Spice Latte.

Same cup. One sounds like a bin at a roadside stand. The other catches on something in your head and stays there. Twenty-three years later many devotees don’t bother with the words. They just say the letters.

Most of what we name in this business is built to slide off. Comprehensive Wealth Review. Annual Client Appreciation Event. Q3 Planning Touchpoint. Nobody repeats those out loud. Nobody's kid counts down to one.

When a name really lands, it stops describing our thing and starts naming the whole category. Everyone who follows has to borrow our words to explain what they do. I'd hold that part loosely as a goal. Let’s just aim for memorable. The category tends to follow whoever was interesting first.

Which brings me to our calendars.

Twelve months at the same temperature. The quarterly review in March looks like the quarterly review in October. Commentary goes out. The newsletter goes out. Nothing wrong with any of it, but our clients couldn't tell what time of year it is from anything we've sent them.

We already have seasons. We just haven't named any of them. The RMD scramble against the custodian cutoff. Loss harvesting in December. The 1099 that lands in February and lights up forty phone lines in a week. Beneficiary designations nobody has looked at since those kids were in middle school.

Most of us treat all of that as operational load to be absorbed. Every one of them is raw material for something clients would look forward to. Pick one, name it, set the date, and say the date early, because the waiting is half of it.

Here's the part that's bigger than the calendar.

Pumpkin spice stopped being a menu item somewhere along the way. It's a line in a revenue forecast now, a shelf-space fight every August, a number analysts ask about on earnings calls. It went from a feature to something closer to an asset class, which is a ridiculous sentence to write about nutmeg, but true anyway.

Most of us started right there. Something that already existed, that we cared about more than was strictly reasonable, that we thought could go further than anyone was taking it.

That's my version of it. We help advisors manage all of their data without the bloat and hand them complete control over it. For most of my career, data was a feature. A tab inside somebody else's platform, bundled in with the thing you actually bought. That era is over. What advisors are building on top of their own data moves faster than anything I have watched in this industry, and the checkbox became the asset.

So what's the next PSL sitting inside your business already? I don't mean a new product line. I mean something already in the building. The piece you care about more than anyone else on your team does, the one that lines up with where the culture is actually heading.

And the harder question underneath it: do you have the freedom to build it? Plenty of good firms have the idea and no room to run at it. That's the thing to fix first.

Have a great week, friends. Let's go make something people wait for.

Jud

Episode 159: This week on Next Mile, Kyle Van Pelt is joined by Melissa Caro, Founder at My Retirement Network. For the past decade, Melissa has studied real advisor conversations to understand what communication behaviors build stronger client relationships. Today, she helps advisory firms close the client language gap through digital learning, live coaching, conversation analysis, and AI-powered insights that turn real client meetings into learning opportunities.

Melissa talks with Kyle about why the best financial advice starts with the right conversation. They explore why wealth management is a people business first, how to make discovery meetings feel less like data collection and more like meaningful conversations, and how advisors can use AI and technology to create more room for human connection. 

In this episode:

(00:00) - Intro

(02:08) - Melissa's money moment

(04:15) - What Melissa learned on the trading floor

(05:50) - Melissa’s transition from equity trading to advisor coaching 

(08:06) - What separates elite advisors from the rest 

(10:14) - How to make discovery conversations more engaging 

(14:36) - Why soft skills are as important as technical skills 

(17:45) - Practical ways for new advisors to build communication skills 

(19:41) - The difference between coaching next-gen and seasoned advisors

(22:59) - How AI is changing the dynamics of human connection 

(25:19) - How overbuilt, poorly integrated tech stacks hurt advisor behavior

(28:24) - Melissa's outlook about the future of wealth management

(30:51) - Melissa's Milemarker Minute

Milemarker on the Road
Catch my team on the road at the following events or cities:

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

Jud Mackrill