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Investments, Real Estate, and Business Strategy

Jon is a Registered Investment Advisor with extensive experience in Real Estate Development, Private Equity, and Business Strategy.

In 2013, into 2014, Jon helped a few friends organize various businesses. From a hospitality venture to a bar/restaurant, and in that time, he decided to establish his own consultancy, named Jon P. Kaiser, LLC.

In 2015, Jon moved to Palm Beach, Florida to help a mentor of his, Chris Rowe, start up his Investment Advisory firm. Following the launch of that firm, Jon helped facilitate client relations for the AIG Financial Network, which was a nationwide group of Financial Advisors that was eliminated by the board in 2016. Jon was a member of the acquisition and development team at Smigiel Partners from 2016-2019, where they bought and developed thousands of acres of land into single family homes, commercial developments, and mixed-use properties.

In 2018, Jon took and passed his Series 65 Exam, and subsequently founded his Investment Advisory firm, J. Kaiser Management, LLC. With this company, he focuses on private equity and retirement planning, while also trying to educate the public about investing.

Jon has had hundreds of inquiries about businesses and has advised dozens of low-income clients or young entrepreneurs free of charge. He believes having a business mindset will set these folks up for success, whether their initial idea is successful or not.

A few of Jon's previous clients or projects:

Non-Profit, Organizational, and Corporate Governance

Jon is an active member of his community that believes volunteering his time is important for proper balance between work and life. In High School, Jon was a member of nearly every organization that he could and was elected Senior Class President at a school that he transferred to only one year prior.

In the Spring of 2013, Jon and his childhood friend Scott Mateski re-formed the Tony Hayshakers amateur baseball team. Jon put together the team's schedule while Scottie worked on recruiting guys to join the team. 10 seasons later, in 2022 the Hayshakers earned their second WBA State Finals berth, and fifth straight Upper 13 Championship.

In 2024, Jon, along with a group of local athletes that were also dissatisfied with the local options for organized baseball, formed the Blue Hills Baseball Club, Inc., a nonprofit organization created to grow and support the baseball community in the greater Blue Hills Regions, which includes Ladysmith, Bruce, Exeland, Weyerhaeuser, and surrounding communities. They established a new team named the Blue Hills Beasts and joined the Independent League of the Wisconsin Baseball Association. Jon and his teammates established the Beasts with the intention of joining the most competitive league in the WBA, which is a 55-team amateur baseball league that spans from southwestern Wisconsin to the northern tip of Wisconsin, and much of the central part of the state as well. The Independent League is composed of only five teams, the Hayward Hawks, Haugen Knights, Brill Millers, Spooner Cardinals, and the newly formed Blue Hills Beasts. Each of the other four teams in the "Indy" League have made the state finals in recent years, including WBA State Championships for Haugen in 2021 and Brill in 2013. Both Spooner and Hayward have also been in the state finals consistently over the past decade, solidifying the Independent League as the strongest in the WBA. In their inaugural year, the Beasts are the only Indy team in the "B" Division of the WBA, meaning they would not compete against the other Indy teams in the WBA playoffs. The WBA recently separated the league into two divisions to increase competitiveness and allow for more regional sites.

In 2018, several months after returning to Wisconsin, Jon was appointed to the board of the Ladysmith Community Industrial Development Corporation, an entity with a mission to facilitate economic development in the greater Ladysmith area. He has served as the Vice President of the IDC since 2023. One of his accomplishments with the IDC was investing over $60,000 into the Ladysmith Manufacturing program, teaching our students skills that will allow them to join the local workforce immediately upon graduation.

In 2019, Jon was appointed to the board of the Flambeau Valley Arts Association, which is a nonprofit organization that promotes the arts in the area and presents a handful of visual and performing arts performances each year. Upon arrival, Jon was able to bring the World Famous Glenn Miller Orchestra to Ladysmith, one of the biggest groups to perform in Ladysmith.

In 2022, Jon helped establish and organize the first inaugural Extra Innings cancer benefit, which featured a marathon softball game and live music, along with a Celebration of Life for victims of cancer. Later that year, he was appointed to the board and was given the position of Music Coordinator, in charge of booking all of the entertainment for the organization's flagship event in Wausau, which continues yearly on the third weekend of June.

In the Spring of 2023, Jon was appointed to the Board of Directors, and subsequently elected President of Family Health Center of Marshfield, Inc., a federally funded community health organization that provides dental, mental health, substance abuse, and primary healthcare to thousands of patients in need across its 14 locations in central and northern Wisconsin. FHC has over a $50 million annual budget and over $100 million in assets and employs nearly 400 people.

Nonprofit Endeavors:


Jon is a well-connected political strategist that has been professionally involved in more than 25 political campaigns in Wisconsin and Florida and has represented various private clients for political consulting and government relations. 

Prior to stepping foot on campus at UW-Madison in 2013, Jon was appointed Vice Chairman of the Wisconsin Federation of College Republicans under Chairman Tim Duffy, and in that position, he oversaw a great expansion of the state organization, which resulted in a great number of students getting involved in campaigns across the state in 2014. Following the 2014 election, the WICRs were praised for their impact on the statewide race. While in Florida, Jon served as Vice President (2015-2016) and then President (2016-2018) of the Palm Beach County Young Republicans, one of the most active YR chapters in the country at the time.

In 2022, Jon ran for the Wisconsin State Senate in a three-way race for District 29. Despite being underfunded and being located nearly two hours from the population center of the district, Jon earned over 18% of the vote, and won the majority of votes in Rusk, his home county. In that race, Jon was endorsed by Representative James Edming, Senator Romaine Quinn, the Wisconsin Realtors Association, and many more notable people and organizations, despite being an outsider in the race.

Jon remains politically involved, as a member of the Rusk County Republican Party, Wisconsin Young Republicans, and as a board member of the Realtors Association of Northwestern Wisconsin Political Action Committee.

Previous Political Endeavors:

Music Industry

Jon is a multi-instrumental musician and has turned his love for music into a professional hobby. He started learning piano at a young age with his instructor Judy Buchholz, followed by learning the saxophone in middle school from Flambeau Band instructor Nathan Gerlach, and then he taught himself the guitar shortly after. He earned several honors and awards while in high school for both his saxophone and vocal work. 

Jon was very involved with the Northwoods Rock Rally, as he had a love for rock music and an interest in audio production. Phil Schmidt and John Edming allowed Jon to attend Rock Rally as long as he was working, so Milo Hanson, John Tellis, and Dave McSweeney (among others), would find various jobs for Jon to do during the event to keep him busy.

When Rock Rally announced its last year in 2018, Jon was committed to bringing it back someday. After producing a few of his own concerts in the years prior to the Covid pandemic, Jon struck a deal with Phil to bring back Rock Rally and founded his concert promotions company JK Productions. Jon "Resurrected" Northwoods Rock Rally in 2021 to a sold out crowd, and in 2022, he announced the return of Northwoods Country Rally as well, however that venture proved to be much less fruitful, as the 2023 iteration of the event was canceled, along with any future plans to hold the event. In addition to his festivals, Jon has also produced shows such as the NWRR "Winter Jam", Shallow Side's "Storyteller" series, the "Battle for the Northwoods" at the historic Silverdome in Neillsville, and other offseason shows that have been well-received.

Jon has also played in several bands over the years, including playing guitar in Flight 56 (with high school friends Jose McKittrick, Arik Johnson, Andy Johnson, and Mitch Ludvigson), bass in Ladysmith City Limits (with Wayne Zindler and Bryan Anderson), and vocals/guitar in ...To Be Alive (with DJ Harm and Paul Lasiewicz formerly of Contingency and Zac and Sully Neal). ...To Be Alive was formed in 2021 as a fun way for Jon to be able to play at NWRR. However, once the band was formed, they quickly realized that it was much more and proceeded to play several shows from 2021 to 2023 that displayed their abilities. In October 2023, TBA opened for the band 10 Years at the St. Croix Casino in Turtle Lake, WI, marking their first performance under the name ...To Be Alive. The band started writing music and plans to release an EP in 2024. In late 2023, Jon started working with longtime friend Ethan Gunderson on his contemporary country project "GUNDO", they plan to release a full length album by Fall of 2024.

Past and Present Musical Ventures:

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