Married to Annie (Fitzgerald), Olson has quite a back-story of his own.

First off, could you tell us a little bit about yourself? Your family, education, background/previous stops, career, etc.?


    I grew up near Lake Ontario in upstate New York the middle of three children. That region of upstate is known for record snow but not the kind of cold you get here in Crookston.  Just as hockey is an important part of the culture here in Minnesota, lacrosse was to us in upstate New York where I was very fortunate to start young and be well coached. I wanted an adventure for college so I chose to attend the Virginia Military Institute.  I played lacrosse at VMI and spent some time as a high school teacher and varsity lacrosse coach.  I left teaching and found my way to NYC where I was eventually lucky enough to meet Annie Fitzgerald. We started dating after about 6 months but not before she made me promise that if the relationship lasted we would one day to move to Minnesota. I was later invited to join a startup which is now in its 10th year and expanding to Europe. The flexibility of working for a small firm has allowed me to work remotely from our home here in Crookston where we’re incredibly happy to be raising our son, Will. We’re incredibly fortunate.

When you were first approached about the possibility of being profiled in our Community Connections special edition, you initially said that your wife, Annie Fitzgerald, born and raised in Crookston, would be the more interesting person to profile. What spurred you to say that?


    Annie is a beautiful woman, an exceedingly kind person, a local girl, a small business owner, a very talented musician and a great mom.  She has shared stages with pop icons and song writing legends. Her circle of friends includes gifted musicians and successful actors and artists. I can’t hold a candle to any of that.

When we were discussing in the Times’ newsroom who would be potentially good profile subjects for this edition, your name came up and it was said that you have a “great back story” for a profile like this. Going beyond how you answered the first question of this profile that sought some basic background information, can you delve into your back story a bit more? It seems you have a wide swath of experiences at a relatively young age.


    That’s very kind of whoever thought my life warranted consideration. To be honest though, I’ve been lucky.  I’m stubborn, impulsive and usually over confident. I’ve been bailed out by a willingness to take some lumps and improvise when I’m wrong.


    My quirks have led me to make choices other people might avoid. I chose to be a goalie in multiple sports because it was always where the action was. I chose to attend an all-male military college because it scared the hell out of me. I chose to move to NYC because it was an adventure.  In all cases, the most rewarding part of each choice has been the people who have become a part of my life.


    Moving to Crookston is no different. When I committed to it I had never been to Minnesota, let alone a place 4.5 hours north of the cities.  Northern Minnesota living isn’t always easy but it’s fun and challenging.  I feel like the culture and people are better for it.  I enjoy it and I want my children to grow up in it.

Do you think making downtown Crookston a vibrant, alive focal point for the Crookston community as a whole - someone the other day said the goal is to make it the “heartbeat” of Crookston - is an achievable goal? Or is getting some of the way there good enough, and realistic enough?


    I wouldn’t have gotten involved if I didn’t believe it was possible but I do believe it’s a big a lift that will require support and a long term commitment/engagement. Sustained commitment is the most important factor to revitalization. The changes that have led to a need for revitalization didn’t happen overnight. It’s important to keep in mind they can’t be reversed overnight.  If the community is  committed to revitalizing downtown there is no reason we can’t succeed.  That’s the distinction though.  Fargo didn’t bring back their downtown by forming a committee and cleaning up a couple of buildings.  It was a long sustained effort that included “out of the box” thinking when necessary.


    Is a partial revitalization “good enough”? I believe in not letting perfect be the enemy of good but I think it’s far too early to start lowering the bar for what we’re trying to accomplish. We need to aim above the mark in order to hit the mark.

As a supposedly unbiased, objective new resident of Crookston, have you run into a lot of biased people who are entrenched in their ways and beliefs since you’ve moved here?


    We’re all biased in some way. I disagree with the implication that Crookston has a somehow greater proportion of “biased” people than other places or that I’m without my own predilections. That said, I think “resistance to change” is pretty universal.  It’s not isolated to small towns.


    As an outsider, I see a community that has endured a lot.  Depressions, recessions, floods and sweeping cultural and economic changes. Crookston didn’t survive those things without a whole lot of people who “stick to their guns” and work hard in the face of challenges. Having overcome such adversity there are probably some who feel that change is unnecessary or unwanted. That’s understandable and should be respected.


    But the reality is the downtown is slowly withering and the community has a choice to make. Do something about it or let it disappear. If we choose the former then we also have to accept that we won’t solve the problem with the same level of thinking that created it. The status quo won’t work.

List three things that have surprised you, in a positive way, about Crookston. Please explain them…


    • I’ve found Crookston to be very warm and open to new people.  That seems trite but it’s true and I appreciate how welcoming everyone has been.  It’s fun being known to everyone as “Annie’s husband”.


    • So Much Free Ice Time – I grew up in a town 2-3 times the size of Crookston with only 1 sheet.  Ice time was precious and expensive.  This is such an understated luxury.


    • Sugar beet campaign – I’ve never seen an entire community mobilize the way Crookston does during campaign and the sheer volume of what gets stacked outside the beet plants is mind boggling.

How about three things that have kind of caught you off guard in a less than positive fashion about Crookston. Please explain them as well…


    • -30 is hatefully cold. I wouldn’t say I was caught off guard by it but there is no way to really prepare for how cold it gets here sometimes. It’s great. Makes you feel alive…freezing but alive.


    • For an area with such a rich hunting/fishing/farming culture I’m surprised there aren’t more farm to table dining options.


    • The response from some of the community when the DCDP received funding to hire a part time downtown coordinator was surprisingly negative but I imagine that was based on past experience with government funded projects which often have a reputation for bloat.

Given what you currently do for a living, can you somehow explain the stock market’s continued surge and how it relates or maybe doesn’t directly relate, to the current state of the economy?


    Flattered you would ask that but if anyone was able to build a model that explained stock market’s ebb and flow accurately they’re unlikely to share it with the rest of us.  The market is not the economy.  

On a related subject, given what led to the housing boom going bust and the “Great Recession” several years ago, do you think a different kind of bubble could burst or a different type of shady profit motive could lead to a similar economic disaster today or in the near future? Or have enough regulations been put in place since the Great Recession? Were any lessons truly learned, or is it still all Gordon Gekko, “greed is good” on Wall Street?


    That’s above my pay grade.

Do you possess any quirky or unique talents, skills or habits that people outside of your inner circle are most likely unaware of? Care to share any?


    Asking an old goalie if they have any quirks is akin to asking whether a bear does it’s business in the woods. No real talents to speak of…I was a physics major my first 3 years of college (after I switched to biology there was only one physics major left in our class). I used to play Johnny Cash covers in a band. I can cook a solid batch of chili, sauerkraut or ricotta gnocchi. Growing up I idolized Ron Hextall and Michael Jordan. I’m a big fan of dogs….rescue, pure bred, whatever.  I’m likely the worst golfer in Crookston and I might also be the worst fisherman but I still happily do both.

Describe where you think/hope you'll be in 10 years, or what you think/hope you'll be doing, personal life-wise and career-wise.


    In 10 years I hope to be coaching a lacrosse program here in Crookston that allows me enough time to go see my wife perform and my son participate in whatever activities he deems worthy of his time. I hope that in 10 years the seeds we’re planting with the DCDP will have grown deep roots and Crookston will be on its way to having a thriving downtown again.    

Please describe yourself in ten words or less...
    Will’s dad. Annie’s husband.