The Entertainment Guide

Artist of the Month: Jesse Totushek

After 22 years of sharing his love for music from the stage, Jesse Totushek has forged a lifetime’s worth of stories to share about the exciting-yet-realistic life of a working musician. Totushek is a Minneapolis-based guitarist, vocalist, and songwriter with a wealth of performing experience as both a solo artist and a member of the talented acoustic music ensemble the SOBs. Totushek performs with two guitars and a mandolin and has recently been enjoying the rewards of integrating TipTree into his business structure. 

Music Has Always Been a Part of Jesse’s Life 

jesse-totushekJesse Totushek’s passion for music was first sparked at the young age of five or six years old when he discovered the most magical machine he could ever imagine: a record player. He would sneak into his brother’s room in search of a record containing his next favorite tune – typically earning a loving punch in the arm for snooping. Nevertheless, it was always worth it to enjoy the overwhelming sense of joy he felt when listening to the beautiful combinations of instruments. From there, the rest was history. 

Side Project Turned Musical Success: The SOBs 

What started as a side project band back in 2005 has now grown to play almost 2,000 shows. Jesse Totushek, the founder of the Singers on Barstools or the SOBs, finds it crazy that they have made it this far. The SOBs are an acoustic trio that plays mostly on Sundays and Wednesdays and, throughout the course of their careers, Totushek has played alongside many talented musicians who have filled in during performances. For the past 14 years until even today, they have been performing live every Wednesday night at Turtles Bar and Grill in Shakopee. 

The Unforgettable Memories 

One of the most memorable experiences Totushek has had as a musician was when his band, the SOBs, opened for country music star Gary Allen at the Surf Ballroom when Jesse was just 22 years old. There were 2,500 people at the show, and he couldn’t wrap his head around the rush he felt being on stage with his friends, doing what he loves and connecting with such a large audience at the same time. 

The show was incredible and, after Gary Allen was finished performing, he was intrigued enough by the pile-of-junk 1963 tour bus the SOBs called home that he joined them inside the bus and played a few songs with an acoustic guitar for Totushek and his friends to enjoy. Observing masters in their element is always a moving experience, but there was something magical about having one of their idols performing just for them. 

As if their night wasn’t memorable enough, Gary Allen’s band and the SOBs all went out to Buddy Holly’s crash site at 1am – talk about living the rock star lifestyle! 

Jesse Is More Than A Musician 

Outside of his time practicing his sets and performing on stage, Totushek has many other interests that occupy his time. He is a classic example of a handyman, and not just when it comes to navigating guitar strings. What might be surprising to his fans is that Totushek actually worked as a plumber for eight years and, in his free time, he loves to work on projects around the house. If that’s not surprising, wait until you find out that he also has 25 chickens at home to keep him company. 

The Future of Jesse’s Music and Navigating The Business Aspect of The Music Industry 


There are countless artists that Totushek draws inspiration from, but Mark Knopfler and Tom Bukovac tend to reside near the top of his list. Although Totushek muses on the fact that it has been years since he has focused on writing original music, he plans to return to this hobby in the coming months. One of his favorite parts about being a musician is the relationship he creates with his fans, and sharing original music is a great way to relate to people. Totushek is inspired by how his music can provide a positive effect on others. The joy of hearing that his music made someone’s day better is truly unparalleled so, no matter what, he plans to schedule as many shows as possible. 

Jesse Totushek feels he has achieved success as a working musician because he believes that if you have a roof over your head you’re already doing better than 154 million people, and if you can do it by playing guitar, even better! Still, he never takes his success for granted and continues to strive for improvement in both his musical skills and business approach. Totushek doesn’t believe that it is possible to play an instrument “perfectly.” Instead, he believes talent is mostly opinion-based, and that it is the modern trends of over-editing music that makes music on the radio so boring. It is because of this fact, and not in spite of it, that Totushek is dedicated to the lifetime practicing his instruments in order to improve, but never master. 

Despite the incredibly emotional experience of performing and connecting with an audience through music, one of Jesse Totushek’s favorite parts about being a working musician is the lack of drama found in being his own boss. He has forged the life of his dreams – his way – finding unique methods to get his voice heard and make money along the way. One tool that has helped Totushek grow success as a musician and helped him connect with fans and earn more money is by integrating TipTree into his performances. There is no denying that TipTree played a significant role in bringing in extra income from his music performances. 

2022 will be another big year for Jesse Totushek’s career. This month, he has several shows lined up at venues all over the Twin Cities, mostly comprised of intimate shows in the suburbs. All of the details on where you can watch him play can be found on his website, 

The life of a musician is exciting and full of opportunities for those willing to chase their dreams. 

If you are a musician looking for tools to help you establish a relationship with your fans while earning more tips, go to to learn more.

TipTree lets you create simple landing pages that quickly capture your fans’ contact information along with their tips, so you can generate new leads to follow-up with again and again, even after they leave your page.



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