Lifestyle Personal Lines the Jan/Feb 2024 issue

Scott Wick

Founder and CEO, High Street Insurance Partners
By Chris Hann Posted on January 24, 2024
Q
You have been in insurance your whole career and founded High Street in 2018. Where did you get the entrepreneurial bug?
A
I would say I started High Street probably more out of my insecurity than anything else.

Favorite Vacation Spot: “Half my family would say Vail. The other half would probably say Big Sky. As long as I’m with my family and I get a chance to watch my boys rip down the mountain, it’s an awesome vacation.”

Favorite Part of Living in Travers City: The people (“It’s real. It takes a community to raise children. And I certainly feel like we picked the right community to surround our kids with.”)

Favorite Spot in Traverse City to Take Out-Of-Town Guests: Power Island

Favorite Movie: The Empire Strikes Back

Favorite Musician: Elton John

Favorite Book: “I read a lot, so maybe I’ll just tell you what I’m reading right now: The Unreasonable Virtue of Fly Fishing, by Mark Kurlansky. I can’t read enough of this book.”

Favorite Restaurant in Traverse City: Modern Bird

Favorite Dish at Modern Bird: Fried chicken (“Of course.”)

Q
Wow. Explain that.
A
When I was fortunate enough to write a nice piece of business, I would be that insecure person who would get a professional logo printed, professionally framed, and I would put it in my office so that, when somebody walked into my office, I could pound my chest a little bit.
Q
That in itself sounds almost entrepreneurial.
A
I appreciate that. But what I did find was—the insecurity component of that—when I did lose that business, it was really, really tough. I was out one evening with a dear friend of mine, and we were having dinner together, and he asked me a difficult question: “If you died tomorrow, how many of your clients would show up to your funeral?” It was kind of a knife that went right through me. I think I was doing a nice job driving good, scalable, organic-growth business at a great firm that was on a tremendous trajectory. But I was failing at the personal relationship side.
Q
When your friend asked you that question, were you surprised at your response?
A
I think I was just being self-reflective. If you look at who we are as an organization, you’ll find the word vulnerability a lot on our website. I’m a firm believer that vulnerability is the only way to have any type of intimate relationship with anyone.
Q
It’s hard to change when you’re a grown person. How did you go about changing?
A
I really had to focus inward. I had to focus on who and what I wanted to be, what I wanted to look like, and make a change. So we made some changes. We moved from Chicago to Traverse City, Michigan.
Q
Why Traverse City?
A
Number one, my wife, Megan, grew up in Traverse City. Answer number two is, if you’re going to focus a business on truly being a community-focused agency, it’s tough to do that in a large, urban setting. I really jumped at the opportunity to move to Traverse City. It was great for our children, it was great for my wife, and it was great for us.
Q
You grew up in Wisconsin. You’re now in Michigan. Packers or Lions?
A
I cheer for both teams, but I will always be a Packer at heart.
Q
You ran hurdles at the University of Wisconsin. How did you end up as a hurdler?
A
My dad would take a lawn mower and mow down some grass, and we would work on 40-yard-dash times. It started to get a little boring, so he drove up to the high school, grabbed a couple hurdles, and put those in the yard. So that was the start of my hurdling career.
Q
That sounds like a Hollywood movie.
A
I don’t think there’ll be too many movies about me. But it was a fun way to get your start.
Q
How would your co-workers describe your management style?
A
Supportive.
Q
Tell me about that.
A
The one thing I do know is we’re going to make mistakes. And I certainly like people that aren’t afraid to make a mistake. The most important lessons we learn, not only in life, but in business, are after failure.
Q
If you could change one thing about the insurance industry, what would it be?
A
If we can find a way to be more innovative, to listen to our customers more, I think we’re going to be better for it.
Q
Last question: What gives you your leader’s edge?
A
I want people to feel comfortable enough to challenge the status quo, to be vulnerable, to be open, to be honest, and then be fanatical, once a decision has been made, about where we’re going.
Chris Hann Associate Editor Read More

More in Lifestyle

Times Change, Crime Remains
Lifestyle Times Change, Crime Remains
A review of Knight’s Gambit by William Faulkner
Lifestyle Pamela Wheeler
Chief Diversity and Inclusion Officer, NFP
Reclaiming What’s Been Lost
Lifestyle Reclaiming What’s Been Lost
A review of Optimal Illusions: The False Promise of Optimization.