This article kicks off a new partnership with Northwestern Mutual’s Downtown Milwaukee office. Over the next few months, I’ll sit down with Managing Partner Frank Di Meglio for real conversations about Milwaukee, the city’s business scene, and the people behind both.
But first, let’s get to know today’s guest, Frank Di Meglio:
Born Francesco, he goes by Frank, and moved to Milwaukee from New Jersey three years ago with his wife and daughters.
His office covers Ozaukee County to Kenosha County and has about 250 advisors and associates.
He started with Northwestern Mutual (NM) as a college intern 16 years before he moved to Milwaukee.
This is why I took the NM coffee.
I’m just going to get this out of the way up front because I’m guessing you saw this was an article about NM and you’re thinking, “why is Steve going to talk about financial advisors?”
I get it.
Because, for months, people were telling me I needed to meet this Frank Di Meglio guy. And I was skeptical.
You, too, right?
I mean, I’m fairly certain that what I’m about to say has happened to all of you at some point. (If not, it will.)
Here’s the scenario: You’re on LinkedIn when suddenly a message pops into your inbox. It’s a financial advisor. They arrive with a nice, warm, and personal intro and they ask if you’d be up for a coffee meeting to expand both of your networks.
You hesitate.
That was me years ago when I was getting my first company, Spreenkler, off the ground. An advisor reached out and not only was I skeptical, but I figured I didn’t have time for the coffee meeting.
I took the coffee anyway.
Six or sevent years after that coffee meeting, when something unexpected happened, I had cash available I wouldn’t have otherwise. I’ve never forgotten that.
Still, when it came time to have a coffee and a conversation with Frank from NM, I wasn’t sure what to expect. I assumed we’d talk mostly about money and finances.
Nope.
We talked about people. And Milwaukee.
Frank’s been here three years but if feels like he’s a lifelong Milwaukeean.
It’s interesting to get a guy’s take on Milwaukee when that guy moved his family here from New Jersey where he was born and raised.
Frank told me when he was being shown the city, his realtor apologized for the highway traffic. Frank wondered where the traffic was.
Living 20 minutes outside of downtown, Frank loves that he can get to a Bucks or Brewers game or to a great dinner with ease.
Within just a few weeks of arriving in Milwaukee, he joined a few local clubs and never felt like an outsider. This, in a city where people still ask where you went to high school.
I’m born and raised in Milwaukee and, in all honesty, I get grumpy about this place.
Frank sees things like our festivals, concerts, and more, things I take for granted, and he’s grateful for every bit of it because he knows Milwaukee is unique.
So did we ever get into the numbers a financial advisor lives by?
Sort of.
But we talked more about people and why they matter. And why their goals matter. And finding out if they’re running a business of their own. What keeps them up at night? What gets them up in the morning?
If you listen to Experience Milwaukee, then you know I ask these kinds of questions of my guests all the time.
Hearing them come from Frank made me change how I see financial advisors reaching out on LinkedIn or anywhere else.
So, next time, take the coffee.
Thanks Frank’s advice to you, Milwaukee. Mine, too. And he and I say it without hesitation. Take the meeting.
Worst case, you get a free coffee and meet someone new and connect through each other’s networks. Best case, you get asked questions that change how you think about your own plans.
Frank added one more thing.
If all you know about Northwestern Mutual is a life insurance policy from years ago, maybe it’s time to go back for a second coffee!
Why Milwaukee for Frank?
Frank looked at other cities before choosing Milwaukee. But he wanted to be somewhere he could make a real difference, fast.
This is a city where you can show up, get involved, and matter.
So, over the next few months, Frank and I will keep riffing on Milwaukee, business, tech, people, and coffee. Maybe even our take on our favorite whiskeys.
For now, take a listen below or on Spotify.
I guarantee you’ll be inspired about Milwaukee, your work, and how you spend your time in our city.
Love you, Milwaukee!




