When it comes to building a business, there’s no one route to success — and the journey isn’t linear. You plan, you take the leap, you learn as you go, you hit a setback, you get back up, you pivot, you add, you grow. This can happen in any order, and happen over and over again throughout the life of your business. Sometimes, you can’t even fathom where you’ll end up when you start the adventure.
“Where a portrait artist has somebody they’re painting a portrait of, we work more like a sketch artist. We’re sketching the business from scratch without a picture that we’re mimicking,” says Ryan Prellwitz, owner of Vines & Rushes Winery.
Here, three business owners share snapshots of their entrepreneurial journeys, proving that overnight successes take years of hustle, creativity, and tools to support whatever is next.
When he first planted 50 grapevines in his family’s Ripon, Wisconsin strawberry farm a decade ago, Ryan Prellwitz had no idea that would eventually lead to a bustling five-acre vineyard making and selling midwestern varietals of wine both in-store and online; a Neopolitan pizza restaurant; and a growing space that holds more than 200 public events each year.
With a background in IT and no winemaking experience, Prellwitz took a big chance launching this endeavor. “We had a lot of flexibility in mind. We didn’t know what we were going to need or what would happen along the path,” he says.
He didn’t imagine, for example, that he would get into the restaurant industry. But his love for Neopolitan pizza, finding the perfect pizza oven, a lack of options in the area, and a sound sense that his customers would enjoy it led him to take the leap.
“What I’ve created is what I would like to enjoy,” Prellwitz says, “if I had the time to enjoy it.”
Vines & Rushes Winery started with the Square POS system, and they were easily able to use more products in the Square ecosystem as their needs grew and as they added new business lines. They added Square Payroll to manage timecards and payroll for their growing team, Square Messaging to keep customers updated about their orders, Square Kitchen Display System for the restaurant, Square Online for online ordering, and more.
“We’ve been a beta tester with Square since the original contactless reader came out. Square has been a really great partner. They’re willing to listen to us and prioritize our needs as a business, more than any other business I’ve ever worked with,” Prellwitz said. Through this partnership, both parties offer value to each other and have helped each other modernize to meet evolving business needs.
Where does Vines & Rushes go from here? Prellwitz says that picture is still being painted. “Success isn’t a point you reach. It’s a continual thing you’re pursuing.”
Krista Abel was a single mother and talented photographer with a dream: to build a company from the ground up that provided opportunities for people of all walks of life. As a woman photographer in an industry dominated by men, she was determined to find and grow talent that was otherwise being ignored.
In 2016, she started Dream Home Images, a luxury real estate media company in Santa Cruz, California, with her now-husband, Greg Hansen.
Her goal was to create an artist collaborative providing the most stunning marketing for all things related to luxury architectural photography and videography. She wanted to be professional in everything she did, so she started taking payments through Square.
“I simply didn’t have time to go chasing down past due checks for work that was done weeks ago,” she explains. “As we grew, our services grew. All of the things we offer are customized to each job, and before I knew it, I had 20+ products to keep track of on a price sheet. Then we discovered that with Square, we could enter them in, so everything was consistent every time.”
Square Dashboard analytics tools allowed her to evaluate what products were most popular and where to invest in marketing; Square Payroll allowed her to automate payment and taxes for her growing team,and estimates and deposit tools from Square Invoices helped streamline back and forth with potential clients.
“As the business grew, my constant trouble was time. I had no idea how much I’d be working and how every single thing would require my absolute immediate attention,” Abel says. “Automating many of these tasks has simplified my life and given me countless hours back and allowed me to delegate more to my employees, helping them grow as well.”
As her business expanded, Abel also wanted to invest in more top-notch gear for her employees to create the best imagery. Luckily, she’s been able to take out loans to make that a reality.
“I’ve taken out countless loans from Square, and have always immediately paid them back way before they were due. Most recently, I had a $30,000 loan that was paid back within about 4 months. Square believes in my company and puts their money where their mouth is; they provide me with the capital I need to grow and continue to be successful, all interest-free.”
In 2020, Abel faced the double gut-punch of pandemic uncertainty and a natural disaster — the CZU wildfire, one of the largest wildfires in California history.
“Not only was everyone on our team evacuated from their homes, our dearest employee, Chris, lost his home in the fires. His entire life in a blink of an eye was ashes. This was emotionally devastating to him and to us. The community we lived in was gone. After the news vans left, everyone seems to have forgotten about us,” Abel recalls.
“Square offered a loan that allowed us to replace all equipment much quicker than our insurance would have allowed, so we could pay employees during the evacuation and recovery time. It provided peace of mind so that when we were ready, we hit the ground running.”
As a result, Abel and her team had a record-breaking year, with sky-high sales because they were ready for the booming real estate market.
Now a team of 8, Abel is being thoughtful about how to scale her business, provide opportunities for more unrealized talent, and put employees first. Thanks to automation tools and delegating to her team, just recently she was able to take her first real vacation since her business opened.
Nong Poonsukwattana was born and raised in Bangkok, Thailand, and immigrated to Portland, Oregon in 2003. She knew, even then, that she wanted to start her own business.
“I spoke poor English. But I realized what made me unique: I can cook something different and use that to my advantage,” Poonsukwattana recalls.
She worked in kitchens, eventually landing at a Thai restaurant that was beloved by critics and featured on the covers of food magazines. There, she honed her skills, gaining enough confidence to pitch her Khao Man Gai, or Thai chicken and rice. “I wanted to cook something that wasn’t on every Thai restaurant menu. That gamble paid off because the dish got noticed,” she says.
With $800, she purchased a cart to start her business, Nong’s Khao Man Gai, in 2009, and started taking payments with the Square Reader. She realized she had a lot to learn about marketing and operations. So in between services, she taught herself how to use Twitter to promote her cart, and asked other cart owners for their tips on growing a business.
More than a decade later, Poonsukwattana has two locations using fully integrated POS systems, and a bottled sauce that she sells online and ships nationally, and 30 employees. She is a media darling, having been featured in the likes of The Oregonian, Eater, Vice, Bon Appetit, and many more.
It’s a far cry from when she first came to the country with $70 in her pocket. But even she wasn’t immune to the effects that the pandemic had on the restaurant industry. As foot traffic dried up, so did sales. Poonsukwattana pivoted to adding order ahead, pickup options, and grocery items to her online store. She used Square email marketing to let customers know her predicament and ask for help. She was able to solicit donations and sell gift cards to stay afloat.
“It was hard for me to ask for help. But after the first newsletter we sent, donations, lov and encouragement all poured in. It gave me the power to get through that difficult time,” she says.