Sydney Boschert
Owner & Founder, Bit Blossom Software
If you’ve ever had the misfortune of calling tech support and walked away feeling like you knew less than you did before, you’re not alone. And that’s exactly why Fargo native Sydney Boschert started Bit Blossom Software. Her goal? To make tech support suck less.
From Corn Syrup to Code
Believe it or not, Sydney didn’t start in tech. She began her career as a chemist in 2012, working on cattle feed and high fructose corn syrup. Along the way, she found herself repeatedly cringing through painful IT calls. “They’d ask if I turned it off and back on again for the seventh time,” she said. “And when they had to come to your desk? It was like you’d asked them to donate a kidney.”
Instead of just venting, Sydney did something about it. While still working full time, she went back to school to study math and computer science, eventually earning a master’s in data science.
Taking the Leap
By 2018, she was working as a software engineer, and then moved on to the world of machine learning and anomaly detection. She still works in that field full time, but about a year and a half ago, she launched Bit Blossom Software on the side. “It was terrifying,” she said. “But it was also comforting knowing that I had control over my future.”
Bit Blossom offers IT consulting, software development, app creation, web design, and tech support—but with a human touch. Sydney’s mission is to be the calm, kind voice on the other end of the phone during someone’s tech crisis.
A Heart-Centered Business in a Head-Centered Industry
Let’s face it: IT isn’t exactly known for its people skills. But Sydney sees that as a competitive edge. “The tech is just in between us,” she said. “What I’m really doing is helping people. And that should feel good, not like a chore.”
Still, getting people to leave their existing (often painful) IT providers is a big hurdle. “They don’t want to switch from one terrible experience to a potentially worse one,” she said. That’s why she focuses so heavily on trust. “When someone gives me access to their business and all its tech infrastructure, that’s a huge deal. I don’t take that lightly.”
The Business Plan? Make It Not Suck.
There was no grand Shark Tank moment or app pitch deck that launched Bit Blossom. Just Sydney, tired of apathetic tech people, saying, “I can do better.” And she is.
While maintaining a full-time job, she’s juggling clients, corporate work, and coding with care. And yes, she says “we” in emails, even though it’s just her. “It makes me sound bigger,” she laughed.
Advice for Tech Dreamers
If you’re thinking of getting into tech, Sydney says go for it, but do it with heart. “Figure out what frustrates you in the process and fix that. That becomes your edge.”
For her, the edge is empathy. Her advice to her younger self? “Start sooner. Don’t wait for someone to beg you to launch your idea.”
Outside the Server Room
Sydney isn’t all bits and bytes. She gardens, hikes, and volunteers with Growing Together Community Gardens in Fargo, which supports local food shelters. She also mentors women and girls in coding through the Society of Women Engineers and other groups. “Teaching someone to code is like handing them a key to a door they didn’t know they could open.”
The Bigger Picture
Bit Blossom Software isn’t your average tech startup. It’s led by a woman in a field that’s still predominantly male, built with the intention to serve real people.
That combination makes Bit Blossom a bit of a unicorn.
Sydney didn’t fall into tech because it was trendy or lucrative. She pivoted into the field because she knew it could be better. More human, more helpful, and far less intimidating. That people-first approach is woven into every part of her business. Whether she’s designing an app or providing IT support, her goal isn’t just to solve a technical problem; it’s to make people feel heard, seen, and supported.
n a city where women-led tech companies are still few and far between, Sydney isn’t just building software; she’s building an ecosystem. She’s planting seeds (literally and figuratively), and creating space for future founders, coders, and problem-solvers to do things differently.
“I bring a different perspective. I lead with empathy. And I think that makes all the difference.”
Bit Blossom Software
Ashley Wooledge
Owner, Knowme Promo
Ashley Wooledge doesn’t just sell promo gear. She sells conversations, connections, and maybe a few laughs over a game of Rock, Paper, Scissors.
As the owner of KnowMe Promo, Ashley launched her business in October 2024 with a goal that was less about swag and more about soul. Based in Bismarck, Ashley is no stranger to her hometown—she’s lived there nearly her entire life, aside from a brief stint nannying outside of Fargo. Now she’s all in on growing her brand, and she wants her customers to feel like they’re part of it too.
A Creative Thread
Ashley’s journey into promotional products didn’t begin with a marketing degree or corporate blueprint. It began with tie-dye.
“I was a small tie-dye vendor for years,” she said. “I just loved seeing people wear something I made. That kind of joy never gets old.”
That passion for personal expression led her to a promotions company, where she was hired to help with embroidery but quickly fell in love with the people side of the business. From there, she bounced between a few shops, learning the ropes of production, sales, and everything in between. Eventually, she realized she was ready to do things her way.
“I’m probably not a very manageable person,” she laughed. “It’s easier for me to manage myself.”
KnowMe Promo is Born
Armed with years of hands-on experience and a growing network from her time in BNI and local business circles, Ashley struck out on her own.
KnowMe Promo is her vision come to life: a place where promotional products don’t just display a logo but tell a story. It’s about curating experiences that make people pause, smile, and remember.
“I don’t want to be an order-taker,” she said. “I want to be someone who helps you think differently about how you show up in your community.”
Even with part-time work at Open Water Marine to help with the transition, Ashley is all-in on growing KnowMe Promo into a local go-to.
The Promo With Personality
Ashley has no desire to compete with faceless online giants. Instead, she wants to give customers something deeper than a koozie or a pen. She wants to give them an experience.
“At an event, I had people play Rock, Paper, Scissors to get their promo item,” she said. “It made them laugh; it made them engage. Now every time they grab those scissors or notepads, they remember that moment. That’s what I’m here for.”
Her approach is rooted in emotional and promotional connection. For Ashley, it’s not about what you give away. It’s about how you make people feel.
Lessons and Late Deliveries.
Of course, building a business isn’t without hiccups. From supplier mix-ups to mislabeled shipments, Ashley has had her fair share of learning moments.
“I’ve lost sleep over tumblers not arriving on time,” she said. “But I’m learning to let go. At the end of the day, it’s a product, not a person.”
It helps to have a strong support system. Mentors like her former boss Jane Halverson, are just a phone call away.
“I still call Jane all the time to ask, ‘What would you do in this situation?’” Ashley said. “Mentorship is everything.”
Community Over Competition
Ask Ashley what she wants for the future, and she’ll tell you straight: She wants to be one of the first names people think of when they need promo. But she’s quick to add that she’s not looking to edge out other local shops.
She hopes KnowMe Promo becomes known for its care, its creativity, and its commitment to connection. Not for being the cheapest. Not for bulk discounts. But for being a real person on the other end of the order.
Building A Business That FeelsLike Home
When she’s not dreaming up new product strategies, Ashley is at home with her husband, daughter, and their dogs. She’s often crafting, crocheting, or cross-stitching. Occasionally, she’s being roped into bow-shooting excursions by her husband. And she is always down for a game of pinochle.
As KnowMe Promo grows, Ashley is grounded by what started it all: the joy of creating, the value of relationships, and the power of showing up with intention.
“I want to help people be remembered,” she said. “And if I do that, even in the smallest way, then this business is already a success.”
KnowMe Promo
knowmepromo.espwebsite.com
Facebook | /knowmepromo
Instagram | @knowmepromo
Lora Larson
Owner, My Best Friend’s Closet
Lora Larson didn’t always dream of owning a women’s consignment boutique, but looking back, it makes perfect sense. A self-described former “horse girl” from a small North Dakota town, Lora grew up loving animals and living the tomboy lifestyle.
“I remember our school was doing a magazine fundraiser, and my dad said, ‘I’ll get you anything as long as it’s not about horses,’” Lora said with a laugh. “So I picked out Allure and Teen Vogue. Once I started flipping through those editorials, I was hooked.” What began as a fascination with fashion’s ability to stand out in a sea of sameness soon evolved into a deeper passion that carried Lora through the NDSU retail merchandising program and into the world of corporate retail, then nonprofit, then small business.
Finding Her Fit at My Best Friend’s Closet
Lora had long been a loyal shopper at My Best Friend’s Closet in Fargo, a boutique known for its stylish, affordable secondhand finds. As someone who lives by the motto “bougie on a budget,” the thrill of snagging high-end items at low-end prices became part of her lifestyle. When the boutique’s former owner decided to sell, she saw the perfect opportunity.
“I already loved the store, had experience in fashion and analytics, and it just felt like the right move,” she said. “My husband and I bought it on July 1, 2025. I handle the day-to-day operations and he’s the behind-the-scenes support.”
The Business Behind the Boutique
Despite being new to business ownership, Lora was no stranger to the ins and outs of retail. Her resume includes roles at Vanity and Scheels corporate offices, where she worked in analytics, allocation, planning, and website merchandising. That big-box experience is paying off in a smallboutique world.
“We’re currently going through a bit of a rebrand,” she said. “New website, refreshed colors and messaging, updated fixtures, and eventually, new flooring and signage.”
As she works to put her stamp on the store, Lora is also focused on tapping into a younger audience.
“We’re in a college town, but so many students don’t know about us. Our prices and pieces are perfect for their budgets and styles. The goal is to bring them in through marketing and a better online presence.”
Style as Self-Expression and Armor
“When I worked in nonprofit and had meetings with mayors or CEOs, I’d dress to feel confident and command respect. Fashion is a form of selfexpression but also a kind of armor. You dress for the energy you want to bring into a space,” Lora said.
She sees that same potential in her customers. Whether someone’s looking for a bold piece or just needs a pick-me-up, Lora loves helping them feel good in what they wear.
“If they try something on and it’s not working, I’ll be honest. But if something really shines on them, I hype them up,” she said. “Fashion should be fun. It should make you feel powerful.”
The Reality of Running It All
The transition from employee to entrepreneur hasn’t been without hurdles. Lora has had to learn everything from software transitions to small-business tax law on the fly.
“There’s a lot you don’t know until it hits you,” she said. “You Google what you can, ask other small business owners for help, and hope you’re not missing anything too important.”
She’s also had to strike a balance between front-of-house energy and back-end logistics—something many small business owners struggle with.
“It’s easy to get burned out when you’re doing it all. I want to be on the floor interacting with customers, but I also need to crunch numbers and make strategic decisions. Finding that balance is tough but necessary.”
For the Future Fashionistas
For anyone thinking about getting into the fashion industry or owning a business, Lora has a few key pieces of advice.
“Intern early and often. My senior-year internship changed everything for me. It showed me all the roles I didn’t know existed. Fashion isn’t just about designing or buying. There are so many lanes to choose from.”
The Mission: Shop Small, Shop Smart
Lora is quick to point out that consignment isn’t thrifting in the traditional sense.
“Our pieces are curated. These are gently used or new items, often designer or high-quality brands, at a fraction of the price,” she said. “You’re getting amazing deals and you’re supporting local.”
That local support matters deeply to Lora. Every dollar spent at her store helps fuel the community economy and keeps independent retailers thriving.
My Best Friend’s Closet
mybestfriendsclosetfargo.com
Facebook | /mybestfriendsclosetfargo
Instagram | @mybestfriendsclosetfargo
