A few years ago, I was talking with a client who called about a small claim. A rock had chipped the windshield on his truck. The repair wasn't particularly expensive, but his first question was, "Should I turn this in to insurance?" It's a fair question, and one we hear often. For many people, ...

Not long ago, one of my children asked me a question that I suspect many adults have wondered about.

Artificial intelligence is incredible. I use it every day, and I believe it will transform the insurance industry in ways we are only beginning to understand. AI can summarize policies, compare options, answer questions, and save countless hours. There is no question that it will make our ...

Not long ago, I sat across the table from a young couple with two children, a mortgage, and a bright future ahead of them. Like many families, they were working hard, doing their best, and trying to make wise financial decisions. They also carried three whole life insurance policies that were ...

Last weekend, I sat in the stands at graduation and watched our daughter, Avery, walk across the stage to receive her high school diploma. Like many parents who have experienced this moment, I found myself wondering where the time had gone. For eighteen years, our lives have been measured in school ...

There’s just something about this time of year. The sound of a bat cracking, random Tuesday night games on TV, kids covered in dirt after Little League, and the completely irrational belief that this might finally be the Red Sox's year…again.

Worker's compensation stands as a safety net, ensuring financial protection for employees and legal coverage for employers in the unfortunate event of work-related injuries or illnesses. This policy comprises several key components, each playing a vital role in protecting the interests of both ...

One of the most surprising lessons I have learned during my career in the insurance industry is this: Many of the financially healthiest people I know are intentionally working toward needing less insurance over time, not more. That statement can sound contradictory, especially coming from someone ...

Several years ago, my wife and I sat down to review our insurance. Three kids. A mortgage. Full, busy lives. Like a lot of people, we had done what we thought was right. Our home and auto were covered, and over time, we added a few extra coverages. On paper, everything looked solid. But as we ...

Several years ago, I sat down with a client who walked in carrying a stack of policies and one simple question: “Am I covered?” Technically, the answer was yes. But as we worked through the policies together, it became clear he had spent years saying yes to every extra layer of protection that came ...

Most people have insurance. Fewer people really understand it. I was reminded of that in a simple conversation not long ago. My 13-year-old daughter asked me what insurance actually is, and before I could answer, she said, “It’s just something you have in case something bad happens, right?” I ...

It started like most great ideas do…with me trying to avoid doing yard work. Saturday morning, coffee in hand, staring out the window at grass that was clearly winning the battle. Then, like a gift from above, the clouds opened, a ray of sunshine came down, angels were singing…and the neighbor kid ...

Every year during our intern hiring process, there’s one moment I look forward to more than anything else. We call it the Children’s Puzzle Challenge (I know, super original…our EVP of Marketing is a genius). And no… it’s not what you’d expect.

Last night, the Michigan Wolverines men's basketball team cut down the nets. And if you only caught the championship, it might’ve felt like they just had it…calm, composed, in control. Like it all came together in one perfect night. But anyone who watched this tournament knows…that wasn’t the ...

Spring’s here, the windows are cracked open, and tomorrow is April Fools’ Day…which feels like the perfect reminder to stop letting your money play tricks on you. If things have felt a little cluttered financially, this is a great time to reset. Nothing drastic. Just a few simple moves to clear ...

Minimalism has always felt less like a trend and more like a wiring. Not in a loud or performative way, just in the quiet sense that managing excess never really made sense. Holding onto things “just in case” has never been appealing. If something doesn’t serve a purpose, it usually doesn’t stay ...

March Madness is a good reminder of something simple about sports: You don’t want to learn the rules of the game after the ball is already in play. But that’s exactly how most business owners experience workers’ compensation. The first time many employers truly understand how workers’ comp works is ...

It usually starts in the kitchen. You walk over to the refrigerator, open the door, and something feels off. The milk isn’t cold. The air inside feels warm. Maybe the light flickers, or maybe the familiar hum that has been quietly running in the background for years is suddenly gone. After a moment ...

This might sound like a terrible marketing strategy. But sometimes… we tell people not to buy insurance. Not because we don’t believe in it. We absolutely do. Insurance matters. It protects families. It protects businesses. It protects everything you’ve worked hard to build. But we believe in ...

This week, construction workers hurt my feelings. Even more so than the construction worker this summer who, thinking I was out of hearing distance, muttered to his co-workers, “What kind of sanctimonious prig makes us suspend operations just so he doesn’t have to circumvent our rubble.” I am ...

There once was a builder who loved spring. Spring meant phones ringing again. Spring meant crews back to work. Spring meant jobs lined up and revenue coming in. All winter, he had planned for this moment. He fixed his equipment, lined up subcontractors, and even hired two new employees to help with ...

One of my strengths is that I have a natural curiosity about others. I am very curious whether or not they like me. Another strength is my Spidey-sense when I’m not liked. Last fall on our Europe trip, Katrina and I were on a bus ride and I kept trying to engage the gentleman who sat in front of ...

If your health insurance bill feels shocking this year, you’re not imagining it. For many middle-income families, health insurance has quietly become one of their biggest monthly expenses, sometimes even larger than their mortgage. Here’s what’s happening.

I was down this week. Melancholy. Nostalgic. Ruminative. Reminiscing on the late 80’s when Katrina and I were first married, living in Seattle, and the world was our oyster. It isn’t possible to return to those days…BUT it IS possible to build a playlist of albums from that time period, close my ...

Let’s be honest. Most people don’t hate insurance. They hate the language. Limits. Deductibles. Premiums. Oh my! Then you hit words like coinsurance, out-of-pocket, endorsements, riders, and limits. Suddenly, it feels less like a policy and more like a foreign language that no one ever really ...

When most people hear the word insurance, they think paperwork, premiums, and that one claim that somehow took three months longer than promised. That reaction makes sense. But insurance was never meant to be the end game. It’s a tool. A bridge. A temporary solution. Stick with me.

At Glidewell, we’ve learned something that sounds obvious but is easy to forget: health isn’t one-dimensional. You can’t be truly healthy in one area while neglecting the rest forever. Eventually, it all connects. Eventually, it all shows up.

If you’ve ever had dental insurance and still been shocked by a big bill, you’re not alone. It’s one of the most confusing parts of personal finance and healthcare, and honestly, the frustration makes sense. The issue isn’t that dental plans are useless. It’s that they’re labeled as something ...

The days leading up to Christmas tend to be full. Full calendars, full inboxes, full minds. This isn’t the week for big decisions or major changes. But there are a few small things worth checking before you close the laptop and lean into the holiday. Think of this less like a to-do list and more ...

Back in 2013, I found myself staring at a mountain of debt. Not a small hill. A full-on, “how in the world did I get here?” kind of mountain. I owed $288,000, and somehow I managed to pay it off in 32 months. When people ask how I did it, the answer is simple: I didn’t start with math. I started ...

As the year winds down and a new one begins, many families take time to review their finances, benefits, and insurance policies. One topic that often creates confusion is knowing exactly when adult children need to transition off their parents’ insurance. Some parents keep them on “just to help,” ...

There’s a special kind of quiet that hits a Montana house in January. The kind where even the floorboards seem to whisper, “You sure you want to live here?”

Let see if I can connect the dots. I had been staring at Mount Jumbo (here in Missoula) all winter. The mountain was huge and intimidating, and I knew we had to climb it. By we, I mean me and my Bull Terrier, Ellie. Ellie was up for anything, and I was confident we would have no issues making the ...

Question: What do Glidewell and Thanksgiving have in common? Answer: …hmmm… Okay…we couldn’t come up with a funny punchline, which is why we are in insurance and not stand-up comedy.

A few years ago, during Thanksgiving week, I had one of those moments where life taps you on the shoulder and says, “Hey… slow down.”

This is the recipe you pull out when you want to look like you tried…without actually trying.

You never plan for it. One minute you’re driving home from the grocery store, the next…BAM!....a distracted driver runs a red light and collides with your car. Or maybe you come home from vacation to find your front door kicked in and your valuables missing. Even the washing machine can turn ...

One of the most common questions we hear from business owners is whether their commercial auto policy covers personal use or if their personal auto policy will cover business use. It’s an important question, because most of us don’t live in a world where work and personal life stay perfectly ...

This year has been full of personal revelations and growth. Some have been small…like realizing I’m finally at peace with missing the Paul McCartney concert. Others have been big…like uncovering something new about my marriage of 38 years.

To Our Clients and Future Clients, I want to take a moment to share how we think about insurance at Glidewell and what you can expect when you work with us. First, a confession: I love sales.

Veterans Day isn’t just a date on the calendar…it’s a pause. A deep breath. A moment to remember the men and women who carried the weight the rest of us can barely imagine.

One of the most common questions we hear from business owners is whether their commercial auto policy covers personal use or if their personal auto policy will cover business use. It’s an important question, because most of us don’t live in a world where work and personal life stay perfectly ...

It all started with a text. “Hey man, mind if I borrow your truck real quick? Just need to grab a couch off Marketplace.” Famous last words.

Ah, Open Enrollment…the magical time of year when the leaves change, the weather cools, and your inbox fills up with phrases like deductible, subsidy, and premium increase. Good times.

When You Get Kicked Off Your Parents’ Insurance (A coming-of-age story featuring paperwork, panic, and premiums)

When I was six years old, for Halloween, I wanted to be a cowboy. Not the store-bought kind…the real deal. My mom, the creative one, decided to make it happen without spending a dime. She handed me a flannel shirt, a thrift-store vest, and a straw cowboy hat that had clearly seen better days. Then ...

Hi, I’m Katie, one of the newer faces here at Glidewell, and if you’re anything like me, the world of insurance can sometimes feel like a different language. When I first started, I remember hearing “general liability” tossed around in meetings and thinking… okay, but what does that really mean?

Hey neighbor — Tanner here. Let’s talk about something that trips up a lot of homeowners: “Why is my home insured for less than what it’s worth?” Totally fair question. The short answer? Insurance isn’t about what your house could sell for, it’s about what it would cost to rebuild.

When people ask, “How much car insurance do I actually need?” they’re usually hoping for a simple number. But the truth is, it depends. It depends on your lifestyle, your budget, and what you’re trying to protect.

It was an inauspicious start to my two-week adventure in Europe. The driver assigned to take us to our hotel from the Budapest airport spoke very little English but used hand signals to communicate that he did not need my assistance loading our luggage into his car. I smiled back, but confident ...

There comes a point in every parent’s life when they realize their “baby” isn’t really a baby anymore. They’ve got a job, an apartment, maybe even a dog they call their “fur baby.”

No one plans to get hurt on the job...but accidents happen. Whether you’re working behind a desk, in a warehouse, or out on a job site, injuries can occur when you least expect them. That’s why workers’ compensation exists. It’s not something most employees think about day to day, but understanding ...

Everyone needs an expert in their corner. The more complicated life gets, the more valuable it becomes to have someone who knows what they’re doing…someone who can help you make sense of it all. A pro. A specialist. An authority. Whatever you call it, we all need one.

You’re standing at the rental car counter when the agent asks that dreaded question: “Would you like the rental car insurance?” Suddenly, your brain starts racing. Doesn’t my regular policy cover me? Am I about to waste money? Can I phone a friend? We’ve all been there, and the good news is, you ...

A few months ago, one of our clients, Jeremy, called us in a panic. On his way home from work, he swerved to avoid a deer, hit a tree, and smashed the front end of his car. No one was hurt, thankfully…but the car looked rough.

Starting in January 2026, there’s a big change coming: you’ll finally be able to use your HSA funds to pay for Direct Primary Care (DPC) fees when you’re on a High-Deductible Health Plan (HDHP). I know, that’s a mouthful of acronyms. So, let’s slow down and make sense of it.

The purpose of insurance isn’t to cover inconveniences; it’s to cover devastation. If an event could financially wipe you out, that’s where insurance belongs. If it’s just an inconvenience? That’s where many people are wasting money.

Last October, my phone rang. It was Linda, one of our long-time clients. She sounded a little panicked. “Matt,” she said, “it’s that time of year again. I just got this giant envelope in the mail about my Medicare plan. Do I need to come in for a review?”

You never plan for it. One minute you’re driving home from the grocery store, the next…BAM!....a distracted driver runs a red light and collides with your car. Or maybe you come home from vacation to find your front door kicked in and your valuables missing. Even the washing machine can turn ...

"You don't need to be the smartest person in the room to be the most valuable. You just need to be the person who figures things out when everyone else is stuck."

Worker's compensation stands as a safety net, ensuring financial protection for employees and legal coverage for employers in the unfortunate event of work-related injuries or illnesses. This policy comprises several key components, each playing a vital role in protecting the interests of both ...

Medicare is a federal health insurance program for people 65 and older (and some younger individuals with certain disabilities). It helps cover hospital care, doctor visits, prescription drugs, and more.

September always feels like a season of transition. Kids are back in school, football is on TV, and the year suddenly seems to pick up speed as we head toward the holidays. It’s also the time of year when many people start looking ahead, setting budgets, mapping out goals, and asking, “Am I on ...

Fall is in the air; pumpkin spice is on the horizon and the 2025 Football season just kicked off. And if you’re like millions of others, you’re playing fantasy football this year.

At Glidewell, we believe in something radical in today’s business world: True success only comes from helping others succeed.

Alright, so you've probably heard about workers' comp insurance – that thing everyone says you should have as an employer. But hey, let's talk about why it's not just a box to tick, but a game-changer for you and your team.

Zack and Cody, Mario and Luigi, Serena and Venus, Eli and Peyton…whether fictional or not, siblings are consistently partners in crime, defeating fire-breathing monsters, or dominating a sports field.

I love car insurance. Not because it’s exciting (it’s not), but because it’s what stands between you and a financial disaster on the road. What I don’t love? The price tag.

Katrina and I were the perfect parents…that is, until we had children. Today, we're trying to prove to our oldest son that we're the perfect Grandparents. He's dubious. The following are 10 Reflections from Katrina's and my efforts last week, when my son (Geoffrey), his wife, and their three ...

What’s the value of insurance, and how do we justify its cost?

What is Medicare?

This past summer was a big one at Glidewell. Two of our own…Lexie Schnieder and Levi Janacaro…each tied the knot. (Not to each other… though that would have been a major plot twist. Imagine the headlines.)

One comment (now referred to as ‘the statement’) altered not just the trajectory of my career…but the trajectory of Glidewell as a whole. Before I reveal ‘the statement’, allow me to, as they say in theatre, “set the stage.”

Another day has passed, and once again, I haven’t used the Pythagorean theorem.

At midnight on Day 2 of this event, which I thought would be challenging but fun, I looked in the mirror and decided that I'm an idiot. My eyes were bloodshot, my hair disheveled. I was tired of eating peanut butter and jellies. My legs ached. Two blisters throbbed with each step. My knee screamed ...

Not in a Flood Zone? You Might Still Be at Risk.

In the dynamic landscape of business operations, success hinges not only on revenue generation but also on strategic resource allocation. One crucial aspect often overlooked is Worker's Compensation, a mandatory requirement for businesses with employees. Glidewell, a firm committed to facilitating ...

Glidewell's Philosophy is simply this: "True success only comes by helping others".

Whether the skunk was a poor aim, or our Great Pyrenees exhibited unusual footspeed, we will never know how or why he successfully (mostly) evaded the skunk spray. But he did (mostly).

"Does my homeowners' insurance cover wildfire?" This is a question we hear often, especially after high-profile fires like those in Los Angeles earlier this year. The short answer? Yes. In most cases, home insurance does cover damage caused by wildfires.

Let’s cut to the chase: if you’re one of the many Montanans who just got dropped from Medicaid, it’s not your fault, and you’re not out of luck.