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FEARLESS FEMME FEATURE: Jennifer Streit, Owner of Prize Shoppe

The "Hap, Happiest Season of All" is now upon us! (Ten points if you sang that iconic line from the 1963 Andy Williams classic It's the Most Wonderful Time of the Year in your head while reading it.) Since moving to our small town in Southern Oregon in 2005, I've grown more and more fond of shopping local for Christmas (and year-round) gifts. There is something quite sentimental and special about walking into your favorite local shop and working with the owner or equally-invested staff to find a heartfelt gift. And it's like a joy explosion when your love language is both conversation ("words of affirmation") and giving/receiving gifts... like moi!

It was a Mt. Vesuvius burst of gratitude and joy upon spending an afternoon with Jennifer Streit - the inspiring, kind, creative, thoughtful and genius owner and founder of the crown jewel of gift shopping in Southern Oregon, Prize Shoppe. Nestled in Ashland, Oregon, Prize is a one-of-a-kind shopping experience, especially at Christmastime. Jennifer and her wonderful staff - which includes her muse and marvelous mother, Olive - have curated an eclectic collection of gifts, ranging from French and Italian housewares, delicate diamond jewelry, vintage books and art, cozy cashmere blankets, delectable candies from around the world and oodles more to delight all the senses! Jennifer searches the world over for thoughtful items meant to brighten the soul, mind, body and home.

Prize has a loyal, longtime fanbase of customers, but each new customer who crosses the threshold of the shop is also greeted with the same warmth and delight. It is a haven for inspiration. The kind of place you need to slowly immerse in, giving multiple passes of the eye over each section because you'll always find something you missed upon first glance. This colorful, uplifting, inspiring, luxurious, whimsical and inviting wonderland is my absolute FAVORITE destination for all the gifts on my list. I call my shopping excursions "Prize pilgrimages" because it's rarely a quick pop-in. One must experience Prize, and wander!

My family also knows that it is the go-to source for gifts for me too! My house is filled with treasures from Prize and each hold such special memories. Chief among them, a French travel poster Jennifer found while backpacking in Spain and a glorious vintage Tomaso Buzzi chair that greets everyone who enters our home. During quarantine, Jennifer went above-and-beyond to help my husband and children find the perfect gifts for Mother's Day (including a Miss America themed sheet music card from an old catalogue service) AND my entire family to gift me an incredible framed Italian "art study" for my 40th Birthday, even though distancing kept them from going to the shop in person.

It is an honor to now call Jennifer a trusted friend. Over the years, her words of wisdom and our conversations have become the most precious treasures from Prize... and it's high time YOU heard them too! Jennifer's successful journey to business ownership is a testament to her beautiful life and business philosophies. Just imagine sitting in the middle of Prize hearing her word-pearls, as I call them, as you read our interview...


KATIE: How did you get your start in business?

JENNIFER: Let's see. I was living in San Francisco and working various office jobs. Yes. Just making it work to pay my rent, and happened to meet an amazing girl that loved going to the flea markets. Her name was Christina Ecklund, and we became dear friends! I was so excited to learn that she liked flea markets because I grew up going to garage sales with my mom. I said to her, “Oh my god, can I come with you? I don't even have a car. But could I just tag along?” I was intrigued by it. But I didn't exactly know what I liked. It was the late '90s and the era of shabby chic.

We literally would take old broken-down little pieces of furniture purchased at the flea markets and then drag them up to the rooftop of her apartment to paint and dry. We literally did that for almost a year, and then we had garage sales in the city on like Chestnut Street in Pacific Heights! We were rebels because we didn't have the money to rent a space and we both had other jobs. And it was more of a weekend thing to start with. It was a funny evolution of just starting with nothing. My mom was the first person to loan us $500 to formally start our business. I bought an old, used Isuzu Trooper to haul around our finds.

KATIE: Your mom's name is Olive, which is the best name ever!

JENNIFER: We always call her our angel investor. $500 meant everything. Then we rented this little tiny space on San Pablo in Berkeley. Between a cult video store, which was slightly like a porn shop, next to a Muslim barbershop. It was so eclectic. We celebrated, “Yay, we're gonna have a store! This is perfect.” The old building was so charming, and we enjoyed fixing it up. But we were only open on the weekends because we had other jobs. We didn't take credit cards. We only sold vintage.

KATIE: Was it only furniture?

JENNIFER: It was a mix of furniture and vintage housewares because we had no idea how to buy new. That made our product something completely different.

Our big break was when Pottery Barn and Restoration Hardware found us and we started renting props to them, like maps and trophies and globes. That was the beginning of “oh my god, we're onto something, this is working.” We had these collections that we could first rent out and then later sell. That was a pivotal moment.

We ended up getting the space next door and expanded by taking out a wall. And our very first new product we added was little polka dot baby blankets, which I still carry at Prize today. Then our product just evolved and fast forward, we got another space inside the city because we both still lived in San Francisco and wanted more city customers. In the city store we got discovered by Rachel Ashwell.

KATIE: Wait, Shabby Chic Rachel Ashwell? Wow!

JENNIFER: That was huge. She asked me to take her to the flea markets!

KATIE: What a full circle moment!

JENNIFER: Right?! She asked me to take her to this antique fair in Petaluma, to show her around. It was amazing. That was also a moment where I realized that we were doing something that people really liked and that that my taste in choosing items was appreciated, which was thrilling!

KATIE: What a wonderful realization! You have the BEST taste! So she wanted you to pick out items, or to know your process?

JENNIFER: She wanted to know where to go in that area for treasure hunting.

Christina and I ended up splitting up the stores because life for us was also evolving. I kept the San Francisco (city) store and kept adding more things because I was good at dialing into new stuff. But I still loved mixing the old, vintage items and props – they are my passion. Like the ribbon display case and the trophies, and the maps.

KATIE: Those became a hallmark for your next phase: opening Prize Shoppe?


KATIE: When did you come back to Ashland, Oregon and how did Prize develop?

JENNIFER: I had a unique situation where a customer wanted to buy the SF store. I just thought it was my ticket out. I had been in SF for maybe 10 years and at that point was thinking, “I would just love to finally have a washing machine and a cat… outside of the city.” It was golden opportunity to get something from those 10 years of developing the store and be able to leave the city.

At the time I thought I was going to move to LA but I remember coming back to Ashland first to be with my mom. She said, “You have a little nest egg and you should really buy a house or do something grown up." I just wanted to move to Europe! But mom knows best. So I bought a little house in Ashland in 2005. This space came available and it was giant because my store in San Francisco was literally 700 square feet. I thought about doing new furniture but decided that was unnecessary because I already had enough beautiful things to fill the store with. So it just became different than anything else. One of our first sweet customers had worked as a buyer at Marshall Fields and she said upon coming into the shop, “I love this store because there are so many classifications.”

KATIE: I love that. It’s true!

JENNIFER: That's what I love about having a bigger space. I can have the different areas.

KATIE: When people asked you to identify your style, what do you say?

JENNIFER: I like so many things that sometimes I have to reign myself in. I mean, it’s varied. I have this huge love of sports. I’m a Sporty Spice! And I absolutely love vintage... I mean, literally everything in here is truly a component of me and what I love. I think that's why it works.

KATIE: Oh my gosh, it's perfection. That's what draws people to the store.

JENNIFER: Another customer once said, “I feel like you had a happy childhood.” And I did! I truly had a magical childhood in Ashland. In a big old house with a big backyard, I could be super creative. It was simple yet special. I just see so many things in here that remind me of my childhood.

KATIE: Do you feel like your roots had an impact on your style DNA?

JENNIFER: Yes, definitely my roots and the way my parents were, and especially my mom's style. It was eclectic. My mom had a famous garage sale each year. Once every summer she would like rope off our front porch and literally people would line up. Everything was meticulously tagged and organized and fabrics measured and tied up with ribbon. So much of what I do comes from my mom. Whether or not I knew at the time, I was so inspired by her. Recently I was over at my parent’s house (the house I grew up in) and I went up to my bedroom. It’s still the same! I had leopard wallpaper – which I still love – and purple carpet. And it was filled with basketball posters! Somethings never change.

If I were to tell people how to find their calling or their passion, I think if people really look back into their like childhood at what they loved or what brought them joy, or what was just a natural love or something that they’re drawn to, they would know innately.

When you were a child, you weren't thinking, “should I be into this?” because it’s what you felt like doing. If you just really tap into the little things. For me, thinking of the beauty of my childhood and my home gives me so much strength and ultimately the ability to make decisions. It's not work. Because if you love it, and if it's something that you're just innately born with, and then that creates purpose and success.

KATIE: What were some of your other jobs before going into business for yourself?

JENNIFER: I worked at Nordstrom as a retail assistant, and in Hawaii at the original Banana Republic, and working for those companies was great because I absolutely did learn customer service. It was important for me to have that foundation of retail. I was in my early 20s right after college. It’s funny because I didn’t get a collegiate-type job even though my major was political science at the University of Oregon. I went to college because my dad said that if I didn’t graduate in four years, I was going to have to pay for college myself, so I schemed with my roommate and we decided that if we were both poli-sci majors, we could graduate on time. I just was just going to college to go. I didn't really even know what I wanted. Now I'm so glad I went to have the full experience. But when I graduated I didn't know what I was doing. I also worked for a temp agency as an “admin extraordinaire” and I always made up things to do.

KATIE: Do you feel like that is a component of why you are successful at running your own business?

JENNIFER: I think being an employee first is huge before deciding to follow your own thing. I would never advise someone to not have worked for other people because you won't know how to be a good boss unless you've watched and learned. I remember all of my bosses and the things they told me. One told me, “Don’t listen with your mouth open.” I’ve held on to that advice. It’s hard to be an entrepreneur if you don’t earn it. I feel like I put in my time and I’m glad I did, but I also know I don’t want to go back which inspires me to keep being successful at working for myself.

KATIE: That’s really amazing advice, Jennifer! What has been the biggest challenge that you’ve faced along the way with owning and operating Prize?

JENNIFER: Finding inspiration sometimes, especially if I'm going through something personally, or if I'm feeling burnt out. There are times when I'm like, “Oh, I can't reorder the same thing!” That’s why it’s key that I close the shop during the month of January.

KATIE: When did you first adopt this practice of closing each January?

JENNIFER: From the very first year. I learned quickly that I wanted to do this because everybody resets. You know, we're all burned out by the end of the holidays and it's super quiet in town and I just thought if I don't do that, then the store will suffer. Now everyone expects and respects it, and knows if you have a birthday in January, get the gift now! I’m grateful that that is part of the pattern now, absolutely expected.

I think that would be another piece of advice I’d give: establish what YOU do, which doesn’t have to be exactly how everybody else was or is doing things. Do what works for you.

KATIE: What does Prize now mean to the community?

JENNIFER: I do feel like it's a place for people to come to when they want to feel better. I hear it so many times: “I feel better when I'm in here.” During the pandemic, people said, “I want to look at something beautiful or feel inspired.” It's just an escape for people. Nothing bad happens inside Prize, is what we say. A sensory bubble of things that smell good, with good music and things that are furry, and things that are that are shining, like diamonds.

KATIE: It's multisensory.

JENNIFER: Because I've been here so long, getting to know customers, I now call them Prize family. So many people have come in for the first time with, for example, a new boyfriend, and then later they come in after getting married, or have a baby… or get divorced. I follow them throughout their lives. And I love seeing the generations that come in, from grandparents to little ones. When the little boy who used to come in with his mom is now years later buying for his girlfriend. It’s so special, and I truly cherish that.

KATIE: Yes, absolutely!

JENNIFER: Because everyone on my staff has worked here for so long, too, everybody knows everybody. It’s pretty rare that we don't know someone, unless they’re brand-new customers.

KATIE: All age ranges too.

JENNIFER: Right? I have a group of girls who come in for candy after soccer practice. And I love when spouses start to feel comfortable coming in to regularly buy a gift. They’ll usually start out pretty grumpy by saying, “My wife will want anything in here,” and I encourage them by replying, “Okay, well, first of all, she needs to start a wish list.”

KATIE: That has certainly worked for my spouse! I have a wish list here! So that's my next question for you: how do you help someone find the perfect gift?

JENNIFER: I always ask when they say, “Oh I’m looking for a gift…” for them to tell me two things about the person. Those two things will usually be enough to zero in on something thoughtful.

KATIE: How did you come up with the name Prize?

JENNIFER: I owe it to my older sister, Gabrielle, who was in college long before me. When we were little, she would always say, “Oh, I'll bring you home a prize,” or if she went to the minute market or anywhere. It stuck. It works for the emotions that are felt when customers leave with a “prize” from Prize!


Thank you to my Fearless Femme Feature partner and the lens behind these amazing captures of Prize, Kelly Armijo of ArmijoDesigns!

Mountains of appreciation to Jennifer and the staff at Prize for the loveliest afternoon luxuriating in the shop and her pearls of wisdom, and the warmth of their kindness in helping to pick out the perfect gifts!

Be on the lookout for GIFT GUIDES curated personally by Jennifer and me!

Be sure to visit Prize Shoppe in person, or call to chat with them about finding the perfect gift from afar!

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