20Q: Catching up with local ice cream baron Andrew Osmond


Angela Major

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.

Andrew Osmond

It started as a hobby and then moved on to become a word-of-mouth treat for family and friends. If Andrew Osmond has his way, his Lil Cheeky Ice Cream brand will eventually be in a store near you.

Lil Cheeky is Osmond's gourmet brand of ice cream that uses only natural ingredients for custom recipes focused on unique flavor combinations. His creations also are available in nondairy and vegan options.

The Janesville native almost realized his dream last summer when he was named a finalist in the Block 42 business challenge.

A Craig High School graduate, Osmond also holds a degree in sociology from UW-Whitewater.

For more about Lil Cheeky Ice Cream or how to order, visit LilCheekyIceCream.com or Facebook.com/LilCheekyIceCream.

1.  What led you to create your own brand of ice cream? After traveling and being able to try really incredible ice cream in different parts of the country, I realized we live in the Dairy State and there is no really great ice cream around here—not even in Madison. Everything is mostly mass-produced and, to be honest, boring and forgettable. We live in a state that prides itself on agriculture and has some really great ingredients that are practically right outside our door. I always have loved cooking, so I started experimenting. Once I got the basics of how to do it, I started to tweak things.

2. Why do you call your company Lil Cheeky? Lil Cheeky is a way of saying playful or kind of a smart ass. If something is a “little cheeky,” it's a little devilish. I look at my ice cream like that. It's something a lot people make and enjoy. I just do mine a little bit different.

3. What is your astrological sign? Do you believe in astrology? Aquarius. They're fun to read sometimes, but I don't put any stock into them. I really believe your destiny is whatever you make it.

4. In order, what are the five most popular flavors of Lil Cheeky Ice Cream? 1. Friday I'm in Love (chocolate ice cream with red wine and chocolate truffles); 2. Lumberjack (maple and whiskey); 3. Salted Caramel; 4. Cinnamon Basil; and 5. My seasonal flavors (Strawberry from Skelly's is probably most popular in summer).

5. Do you prefer to read fiction or nonfiction? I love books. Finishing a book is another matter. I prefer nonfiction—usually true crime. The last book I finished that I really liked was “Girl in a Band” by Kim Gordon.

6. What do you recall being the worst taste combination you've experimented with? Early on, I tried to make an English ale ice cream, which was quite terrible. It was sour and had this off-putting brown color. But you never know until you try.

7. What is the strangest thing you've ever eaten? I love weird food. Not gross or bad, but things with unique ingredients prepared in great ways. In high school, I was dared to eat a couple goldfish. That was strange, I guess. One food that some people find strange that is a real treat for me is cow tongue (lengua) tacos. Beloit has some really incredible and authentic taco places that do those so well.

8. What is your worst habit? Probably being on my phone too much—social media and things. I feel a compulsion to look at it every so often. I'm actually using my phone right now to answer these questions.

9. Where is your favorite place to unwind? Honestly, being out on the running trails in the woods. It's really cathartic. This area really has some great trails nearby that you can just go out and just get lost in a good way. I come back so refreshed.

10. What is your most prized possession? I have a teddy bear from when I was a kid. It's been through a lot. It's always moved with me. I just keep him in the closet. I guess it makes me feel good that he's OK and still around.

11. Would you be insulted if someone bought your ice cream and put chocolate syrup on it? I wouldn't be. The whole reason I started Lil Cheeky is because I wasn't satisfied with what there was to offer around here. Ice cream should be what you want it to be. Express yourself.

12. Can you name a popular television show you either have never seen an episode of or that you don't understand why it is popular? I honestly dislike 98 percent of reality TV. Some of the cooking ones are all right. I'll never understand the Kardashian stuff. I just don't see what can be so interesting about them and how people can genuinely care about it.

13. Lil Cheeky uses only natural ingredients. Is that a personal philosophy or a business decision? It's a personal philosophy that's turned into a hallmark of my ice cream. Fake flavors and colors are just that—fake. There are so many incredible ingredients and flavors that are readily available around us. Real flavors get so lost and corrupted when you add in so much fake stuff. Keep it simple.

14. What is currently the wallpaper on your cellphone? It's a cool charcoal drawing of a skull on an ice cream cone that says “cold as hell.” An ice cream place in Boston I talk with on social media had posted some ice cream art, so I snagged a shot of it for my phone. I thought it was cool. It sounds so lame to see the description of it in words. It really is cool, I swear.

15. What do you do when you're not making ice cream? Working my day job as a probation officer. It's a completely different world compared to making ice cream. It really helps me compartmentalize things and put things in perspective. I love my job and work with some really great people.

16. People would be surprised to know that I: Used to have really long hair—like past my shoulders long hair. I had it for my senior year of high school and for a couple years after. That was a weird time. I used to just hang out at my friend's place and play bass guitar in the basement.

17. I'm a vanilla man. Do you have a personal favorite flavor of ice cream? That is so tough, like picking a favorite child or something. If I've got to, I'd go with Bananas Foster. The flavor is very dimensional—roasted bananas, cinnamon, salty caramel and spiced rum. Beyond that, it always reminds me of my favorite city, New Orleans.

18. If you could have tickets to any music concert, whom would you see? If you're talking about a current band, I'd probably say Incubus, which is a big part of my go-to playlist. If you're talking about at any point in time, I would see Jimi Hendrix. He was simply the best ever.

19. What's the best remedy for an ice cream headache? I'm going to break out full nerd on this one: An ice cream headache is associated with a nerve in the skull that is affected when something very cold restricts the blood vessels. The best thing is to press your tongue to the roof of your mouth. Once the blood vessels expand again, boom … you're all good.

20. What is your ultimate goal with Lil Cheeky? My ultimate goal is to have my own scoop shop. I want to offer a wide variety of scoops for cones and sundaes, have pints for sale, plus offer other cool stuff like retro candy and candied nuts. I have visions of something almost like Willy Wonka; you know, that candy store Charlie goes into. I want it to be a destination, a place that when people talk about the Janesville area they say, “Oh, you gotta go to Lil Cheeky.”

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