20Q: Catching up with “Jake of All Trades” Jake Sailing


Anthony Wahl

Editor's Note: Kicks presents 20Q, a feature that introduces readers to people involved in the area's arts and entertainment community. Compiled by kicks Editor Greg Little, each piece will include a short bio, photo and answers to questions that provide insight into not only that person's artistic interests but also his or her unique personality.

A self-proclaimed “Jake of All Trades,” Sailing was born and raised in Janesville, graduating from Parker High School in 1998.

Aside from serving as the driving force behind Tasteful Janesville, an annual taste showcase for local restaurants, Sailing also is the mind behind an ugly sweater party fundraiser that has donated more than $10,000 to local charities since 1996. In addition, he accomplished his boyhood dream of creating a professional wrestling company when he introduced the Janesville Wrestling Alliance through a series of independent events at several area venues.

Professionally, Sailing is owner of Red Stop Productions (redstoppro.com), a local video production company working on a national scale, and Up Ur Sleeve T-shirts (upursleeve.com), a startup that produces  quirky shirts alongside those to promote local businesses and events.

Sailing's continued dedication to his hometown is driven, in part, by his “energized, beautiful and talented daughter” Kiera and his own desire to provide city residents with original, entertaining opportunities that enhance their lives and benefit local charitable groups.

Next up for Sailing is Tasteful Janesville, which runs from 11 a.m. to 9 p.m. Sunday, Aug. 14, in the north pavilion at Riverside Park in Janesville. For more information, search for “Tasteful Janesville” on Facebook.

1. What prompted you to resurrect Tasteful Janesville? My love for cheese curds.

2. You also organize an annual ugly sweater party fundraiser. How many ugly sweaters do you own? Describe your favorite. In my house, I probably have about 10 or 12 (I've borrowed about 36 over the years). That reminds me: Please return all borrowed wool. My favorite was the one I pulled a few years back with little football players on it, one being a quarterback wearing number 4. BRETT FAVRE!!!!

3. You're also the man behind the Janesville Wrestling Alliance. What is the organization's standing at this time? At one time we were having more than 100 kids attending events. Sadly, we ran into venue complications and were left without a home. It would be amazing to have a building myself. (Hmmm … what are they doing with Black Bridge Bowl?) We have had a few possible leads recently that would be good for the winter months. I might even try to start bringing in autograph sessions and meet and greets. I have kept in contact with a few big names. Let's just say I have been mistaken for a certain other Jake.

4. What additions and improvements can people expect at this year's Tasteful Janesville? Last year was a great event with great flow, local talent, local food and beverages. We aim to continue to promote local. We have newly added games and events. I am excited to see people enjoy some of the old-school games we will again offer such as egg toss, wheelbarrow races, potato sack races and more, along with some new attractions such as bounce houses and knockerball.

5. You can sign any professional wrestler to a JWA contract. Who would it be and why? If I could sign any professional wrestler to a JWA contract, it would be “Irish” Andy Anderson. The guy has been with me from the start, and that's tough to do. I'm a handful.

6. You put your neck out with some off-the-wall promotions other people might not attempt. What drives you? I enjoy thinking outside the box. Believing in yourself and those around you and having a good team is key. I would never be able to have even one event if it was just me.

7. Dance craze you wish would come back? Macarena. Not sure if it ever left, though.

8. Best compliment you've ever received? A thank you goes a long way.

9. What is your greatest passion? Spending time with family and friends. Learning.

10. How much money has your ugly sweater party collected in total, and what organizations have been helped by the donations? Over the years the sweater party has evolved. From my parents' basement to a house that burned down to the Pontiac Convention Center, Black Bridge Bowl and now … ? We have managed to donate more than $10,000 to charities and have no plans to slow down. We have donated to ECHO, Red Cross, the Humane Society of Southern Wisconsin, Project 16:49 and Janesville Community Radio. We could not have done this without the help of sponsors and the local community.

11. Who are your role models? My parents have always been there for me. I cannot thank them enough. I also enjoy Chuck Norris, Bo Jackson and Shaquille O'Neal.

12. What is your favorite food? Why? I am a fan of tacos. I think I just like saying the word. TACOS.

13. What are you most afraid of? Staying stagnant. I have found it drives me nuts knowing how to fix something and to not move forward with it.

14. Name a musical artist who doesn't get nearly enough credit and one that gets too much credit: I enjoy classic rock these days, and I've been teaching my daughter the difference between Bieber and Zeppelin.

15. Have you ever come up with a food creation you think is fantastic but think the rest of the world isn't ready for yet? I am working on a creation called the Peanut Butter Jake. Yes, it involves a Twinkie.

16. Have you ever cried at a movie? Don't think I ever have at a movie theater, but have you checked out the Jake “The Snake” Roberts “Pick Your Poison” movie? That one got me.

17. What is the most dangerous thing you've ever done? I ran through a fire a few times while my house burned down, so that has to be up there.

18. Who is your favorite Kardashian? Another tough question. I would go with nonblood on this one and say Lamar (Odom) or Scott (Disick). If I had to choose an actual one it would be Kourtney Kardashian. She and I both like it when Kim cries.

19. What one item goes in your shopping cart whether you need it or not? Bacon.

20. If you were to open a restaurant in Janesville, what would the name be, what would the theme be and what type of food would you serve? I have recently talked about doing something food related, but for now I have to keep you guessing. Come on out to Tasteful Janesville on Aug. 14, and I'll tell you about it.

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