Perhaps you’ve noticed when you hit the checkout button on your online purchases there’s often an option to buy now, pay later. It’s reverse layaway—you get the goods now, and you pay them off in a four or six interest free installments. No fees, no need for credit. Young consumers seem to love it and so buy now pay later is being embraced by more and more retailers, from small indie shops to the big direct to consumer brands like Peloton and Warby Parker.

The pandemic only accelerated adoption rates and analysts project buy now pay later solutions could rack up $680 billion in transaction volume worldwide by 2025. There are several big players in the field, like Afterpay and Affirm, which hit a $24 billion valuation after going public in January. But that hasn’t deterred Sezzle, a Minneapolis-based buy now pay later platform that went public on the Australian securities exchange in 2019 and continues to gain traction in the U.S.

“I want to win,” says Sezzle founder/CEO Charlie Youakim, who was featured on TCB's Tech 20 in 2020. “We’re still in last place in the payment space, even though we’re having success. That’s what drives me. I know we can beat them. We just have to keep on innovating and listening to our stakeholders.”

Yoaukim didn’t set out to create a payment platform. His is a winding founder’s tale that includes many startup signatures: sleeping on a couch, a fallout with a co-founder, a failure that eventually led to the big idea.

"Start small," he advises other founders. "Find that first customers. Make it work great. Listen to that customer. When they have issues, fix them. When they have ideas, do them. Keep on walking forward."

Sezzle launched in 2017 as a payment processing platform. Retailers liked the model because it was less expensive than credit card fees, but consumers didn’t latch on.

“We ran with the idea that [a digital payment option] was a preference," Youakim says. "But what if it’s not a preference? What if it’s a lack of access? We flipped the hypothesis. We had to build a credit system.”

Investors weren’t initially sold on the pivot. Youakim shares the process of winning them over, the advantages of going public in Australia, why buy now, pay later resonates with consumers, and how he’s placing purpose alongside profit with new products designed to help consumers build their credit scores. Everything is clicking now: Sezzle doubled its headcount in 2020 to more than 200 employees. The Minneapolis-based company just recently announced its certification as a B Corp, emphasizing its mission to "financially empower the next generation."

“You just keep on pushing ahead,” Youakim says of building a business. “It’s like mountain climbing. Know where the pinnacle is, and keep picking a path with the goal that you want to get to the top.”

Following our conversation with Youakim, we go Back to the Classroom with University of St. Thomas Opus College of Business. Consumer behavior expert Kim Sovell, a participating adjunct professor of marketing is tracking the rapid adoption of buy now pay later platforms, particularly among younger consumers. Usage skyrocketed from 2019 to 2020—200 percent among Gen Z; 86 percent among millennials. “It allows an individual to get immediate satisfaction out of a purchase but not go into debt.” But Sovell worries that the interest free, penalty free offers Sezzle and its competitors currently offer may evaporate. “I think they’ll start charging individuals that miss payments. I think that’s going to change. I also think people need to be aware: it does entice buying more.”

60. Sezzle Founder/CEO Charlie Youakim

Behind many popular drink brands—Mike’s Hard Lemonade, Celsius Energy Drinks, Pabst Blue Ribbon—is BevSource, a St. Paul based company that provides beverage development, sourcing, and production—everything from supplying the can that holds your beer to helping develop and test an entirely new drink idea. Today BevSource is one of the largest packing and ingredient distributors in North America, with $250 million in annual revenue. Janet Johanson started the company in 2002 when she was just 24 years old, with three years of experience in the industry. “I just said yes,” she says.

Johanson talks timing: from knowing when to take on private equity and start a board to knowing when it was time to step away from the day-to-day operations. “As CEO, I got stuck in detail,” she says. “By cutting my hands off, it made me think differently about who we partner with…and how I can make an impact.” 

Following our conversation with Johanson, we go Back to the Classroom with the University of St. Thomas Opus College of Business. Tera Galloway is an associate professor in the Department of Management who studies the craft brewing industry. She explains the idea of “coopetition,” where companies realize is better for their industry to work together than to compete. She talks about the importance of building a network and the critical moment for entrepreneurs, when they realize their out of their depth. “It doesn’t mean you have to leave; you need to get more help.”

122. BevSource Founder Janet Johanson

Kristen Denzer is the founder and CEO of Tierra Encantada, a Spanish immersion daycare that is on its way to becoming a national brand. Currently there are 11 locations in four states—two of them are franchise centers, and an additional 20 franchise units have been sold. It’s already a $22 million business, and Denzer is just getting started. 

Tierra Encantada is actually her third startup; Denzer started her career in nonprofits, but saw business opportunity everywhere. When she got engaged and realized how expensive it would be to plan a wedding, she started her own event rental business. As an animal lover, she co-founded a doggy daycare. So when she went looking for a daycare center for her own children and coulnd’t find one that met her criteria: Spanish immersion, inclusive, healthy meals, quality programing, she started her own. Tierra Encantada started in Eagan in 2013 and within a year, Denzer was working on expansion. She shares what went right, the mistakes she learned from, and why she made the decision to franchise. 

Denzer’s advice on entrepreneurship “Just do it. So many people think about doing something for so long…you’re not going to get everything right and it’s ok because you’ll learn from your mistakes.”

Following our conversation with Denzer, we go Back to the Classroom with the University of St. Thomas Schulze School of Entrepreneurship. Associate Dean Danielle Campeau talks about the “entrepreneurial mindset—an individual who able to see opportunity in a space and take it.” Here are some key indicators, and ways to make the most of it.
-	Curiosity. “A willingness to develop expertise. It’s especially important when you’re launching a business in an area that’s new to you.”
-	Product-market fit. “You can understand an opportunity based on your own experience, but then you’ve got to do your homework and make sure there’s really a need for what you want to do.” 
-	Diverse viewpoints. “Collaboration with partners is key to success. IT’s another way that individuals can fill in their own knowledge gaps.”
-	Perseverance. “A no today is not necessarily a no tomorrow. Those that are entrepreneurial thinkers recognize that and they’re going to persevere through the ups and downs.”

123. Tierra Encantada Founder/CEO Kristen Denzer

When your arteries are blocked, you see a cardiologist. For cancer, there’s the oncologist. But for the 13.5 million Americans dealing with a serious wound—from surgery, an injury or disease, an ostomy bag, or old age—there’s often no one coordinating care until the problem becomes a crisis. Nima Ahmadi saw the white space, and co-founded The Wound Company in 2022 with the intention of creating a coordinated, cost effective solution that supports health care providers and improves healing for patients. 

The Wound Company partners with medical practices and benefits companies to provide focused patient care through a combination of telehealth, AI diagnostics and in person care. Already the data shows that Wound Co. patients heal 60% faster for a 15 to 20% reduction in cost.
 
Ahmadi, who studied bioengineering and worked on other software-focused health startups, walks us through the process of recognizing the problem, devising a solution, and actually bringing it to market. He talks about the challenges of scaling a health care startup and why he believes the big health care companies need to think smaller. 

Following the conversation with Ahmadi, we go Back to the Classroom with the University of St. Thomas Opus College of Business where Mike Porter is a professor of marketing. He talks about the problems caused by a diffusion of responsibility. “What this business is really doing is owning accountability and expertise and aggregating those things in one place…for this very specific outcome.” Porter, who teaches reputation management, also talks about the public’s growing confidence in telemedicine and how that can benefit new innovations like The Wound Co.

124. The Wound Co. Co-Founder/CEO Nima Ahmadi

“Where passion meets frustration creates motivation.” 

Erin Pash is the co-founder and CEO of Ellie Mental Health—one of the fastest growing franchise chains you’ve probably never heard of—yet. The Mendota Heights-based company opened its first franchise clinic in July 2022. Now there are more than 200 Ellie Mental Health clinics open around the country with another 450 sold and under development. 

Pash is driven by the desire to destigmatize mental health care by building a national mental health care brand that makes care accessible and fun while also creating a flexible work environment for therapists.

Pash is a licensed therapist who saw a bigger opportunity. “We wanted to create a hybrid employment model where we could give therapists safety, security and support while providing them with the culture, creativity and compensation they could get in their own private practice.” 

Pash talks about barrier to mental health care, the rising demand for services and how that’s driving more therapists not to accept insurance, which creates barriers to entry for those who need it. She talks about building her business, one practice at a time, and coming to identify herself as an entrepreneur more than a therapist. 

“There are two paths to successful business. One is you’re an entrepreneur and you try 20 things and one sticks. You’re passionate about entrepreneurship. The other is you’re passionate about one thing and because you’re so passionate, people can’t help but want to join you. That’s me.”

Following our conversation with Pash, we go back to the classroom with the University of St. Thomas Opus College of Business where Mike Porter is a marketing professor. He talks about the importance of a passionate founder and the marketing conundrum in the mental health field.  “Not everybody wants to talk about mental health or say, oh, I went to this amazing clinic.” Porter talks about why franchising makes sense. “She’s starting with community."

125. Ellie Mental Health Co-Founder/CEO Erin Pash

What happens after a founder appears on Shark Tank, and walks away from a $250,000 offer? For Beth Fynbo, her Busy Baby activity mat saw six weeks worth of online sales in in three days. “And two weeks later,” she says, “no one had heard of us.”

“I thought Shark Tank was going to be life changing, and it was—just not in the way that I thought.” 

Fynbo, an Army veteran and former health care account manager, was a new mom when inspiration struck. Kids were constantly dropping toys off their high chairs. Her Busy Baby silicone suction placemat keeps toys, teethers, and utensils secured in place. In 2023, two years after her Shark Tank appearance, Busy Baby logged $5 million in sales and introduced new add ons to its core product.

Now with two years of growth and perspective since her national television debut, Fynbo talks about what it’s really like to go on Shark Tank and what it’s really like to build a business from the ground up, including raising money, creating an advisory board, navigating the waves of social media marketing, and charting a path to profitability.

“You’re never too old, and it’s never too late to chase a new dream,” Fynbo says. “I was in the army for 10 years. I had this corporate career for 10 years. I had given up on being a mom, but became a mom and a business owner after 40. And I know that probably 50 or so, I’m going to start the next thing. I just want anyone who is stuck in something they don’t love to know: you can change.” 

Following our conversation with Fynbo, we go back to the classroom with the University of St. Thomas Schulze School of Entrepreneurship where Alec Johnson is a professor. Johnson talks about overcoming the limitations of a “dysfunctional belief system”—that’s the idea, he says, that you have to be creative or you have to be an expert to be an entrepreneur. “You can grow into it. You just have to be a good problem solver.”

126. Busy Baby Founder/President Beth Fynbo

Sean Higgins knew he was spending too much time on his phone—going down a YouTube rabbit hole when he meant to go for a run, or call his mom. But rather than fighting the ever-present phone, he imagined a new way to utilize the technology that sits in the palm of our hands—a better way, if you will. BetterYou is a digital coach that uses artificial intelligence to map how we spend our time and make suggestions to fulfill the goals we set for ourselves, like more exercise, more sleep, or calling mom every week. 

Higgins started BetterYou with partners in 2018, using seed money from his first start up, ilos, a video platform that was acquired by Paylocity and became VidGrid. He quickly realized the real opportunity for an app designed to “harmonize technology with wellbeing” was B2B. The first organizations to sign on were schools, which offered BetterYou as a service for students.  

BetterYou ended 2023 with a $6 million Series A funding raise. It’s still early days, but this app is showing traction with users and Higgins is hopeful the company could hit profitability by the end of 2024. 

Higgins offers advice on going all in, knowing when to pivot, and vetting an idea without falling for false enthusiasm from those around you. He also talks about digital wellness in the age of AI.

“We should be optimizing our lives around the things that matter most—not watching random ads.”  

After our conversation, we go Back to the Classroom with the University of St. Thomas Schulze School of Entrepreneurship where Jay Ebben is a professor. He offers perspective on how AI is creating new startup opportunities, but cautions founders to make sure they're not just using technology for technology’s sake, rather “doing something beneficial that can help our daily lives.”

127. BetterYou Founder/CEO Sean Higgins

“We’re going to be helping hundreds of thousands of patients with our device and that’s probably more than a lifetime of patients I could see as a physician.” 

By the time Allisa Song started medical school at Mayo Clinic in 2018, she was already the founder of an active medical device startup company called Nanodropper. The idea came to her in 2017, when she happened to read an article titled: "Drug Companies Make Eyedrops Too Big, and You Pay for the Waste.”

“It really felt like we were letting people down,” Song says. “We have these great medications that are vision saving, and we’re dangling it in front of people, saying that you have to pay this amount if you want to keep your vision.”

The cost, the structure of benefits—it all felt “unfair,” Song says. But rather than go for the big industry-wide fix, she approached the wasted eye medicine problem with a harm reductionist mentality. “I was just trying to think about how can we develop a solution that we could put directly into the hands of patients.” 

That, for Song, was an eye drop bottle adapter with a smaller opening for less waste. The product, which sells for $19.99,  is now available direct to consumer online and through thousands of medical clinics nationwide. 

Song talks about leveraging student startup competitions to fund the business, and juggling entrepreneurship with medical school. “Taking that first step in bringing your idea to life is a really powerful feeling.” 

Following our conversation with Song we go Back to the Classroom with Dan McLaughlin, senior executive fellow at the University of St. Thomas Opus College of Business, with a focus on health innovation. “One of the things I teach in my operations management class is how do you improve processes?” Often the best way to make a big impact is by addressing something small or seemingly mundane. Look for the opportunities, McLaughlin advises, in your daily routine.

128. Nanodropper Co-Founder Allisa Song

Ashley Hawks was a successful working model, in print and on runways around the world. But when she thought about her goal of making a magazine cover, she realized, “I’ll still be promoting somebody else's brand, somebody else's lipstick, somebody else's clothing line. And it was this light switch of, I want to be on the cover because of something I did, because of something I built. I want my name next to my picture.”

For her first startup, Hawks built on what she knew. Style & Grace offered training for models and pageant queens. She made money, but realized the business wasn’t scalable—all of the students wanted to work with her directly.

Her next venture took her back to her childhood, working in her mom’s bridal boutique. Hawks launched Forever Bride in 2012 as a tool to support the local wedding industry online. She created a network of small businesses and built a national following for her online platform and boutique market experiences. 

Halted by the pandemic, she took a shot and reached out to the CEO of David’s Bridal, who not only responded, he became a trusted ally and eventually acquired Forever Bride in 2022. (They renamed it Pearl.) Hawks went to work for the national wedding retailer, but after a year, realized her entrepreneurial spirit didn’t mesh well with a corporate setting. Her latest venture is Soar Leadership Groups, creating forums, events, and adventures for business leaders. 

Following our conversation with Hawks, we go back to the classroom with the University of St. Thomas Opus College of Business where Erica Diehn is an associate professor of management. She wasn’t surprised that Hawks didn't stay long at David’s Bridal. “It’s really tough to find entrepreneurial experiences in larger organizations.” 

“We call that person-organization fit,” Diehn says. “Not only does the job fit your skills and abilities, but the broader context of the way work is done, the culture of that organization, their mission and purpose. If that’s not a strong fit with you as an individual, that’s a hard one to overcome.”

129. Forever Bride Founder Ashley Hawks

Laura Roos started Minny & Paul as a way to take the hunt out of discovering high-quality, locally made goods. She launched in 2016 with a selection of themed gift boxes that she thought would be popular with bridal parties or for housewarmings. But very quickly, businesses started requesting large orders of boxes for clients or staff. Today, 80% of  Minny & Paul’s business is B2B and the company has gone beyond Minnesota to spotlight makers nationwide and offer curated gift boxes as well as ready-to-order options. 

The creative side drew her in, but Roos talks about the logistics and leadership that have made Minny & Paul a success. 

A request for a customized Minny & Paul box filled with CBD products inspired Roos’ next startup, the new Mary & Jane, which sells microdose cannabis products. 

“I love a challenge,” Roos says. “I think the most important thing to keep in mind as you're building any business is problems are going to come up all the time and it's really just about how you react to them and your creative problem solving that's going to fix them.”

Following the conversation with Roos, we go Back to the Classroom with the University of St. Thomas Opus College of Business where Seth Ketron is an assistant professor of marketing and has studied the subscription box market. His advice to those thinking of starting one is ask yourself: “What's your product? What are you trying to do?" If you're working with something that people…know they're going to use every month, a subscription could be functional. But if it’s just for the sake of a gimmick, you probably want to think that through.”

130. Minny & Paul Founder Laura Roos

If you spend any amount of time in or around the startup community in the Twin Cities, you will no doubt hear the name Daren Cotter. Today, most people know him as an investor and advisor—his personal portfolio includes more than 100 startups—primarily software as a service and tech. But before Cotter could focus full time on investing, he had to have an exit of his own. That was InBox Dollars, the rewards-based digital advertising platform he built in his college dorm room, scaled to a peak of $25 million in annual revenue, and sold, some 15 years later in May 2019, to a leading market research and insights firm, Prodege. Cotter shares his entrepreneurial journey, from concept to acquisition, as well as his investment philosophy and advice for founders—including not raising funds prematurely.

"My personal viewpoint is a founder is often much better served by building the product, finding a few customers, proving that they're solving a real problem that the customer is willing to pay for, and then they think about raising capital."

Takeaways

Following our conversation, we go Back to the Classroom with the University of St. Thomas Schulze School of Entrepreneurship. Professor John McVea who talks about the entrepreneurial mindset.
"It's a stance you take towards problem solving and getting things done that is distinctly different."

Key traits, McVea says, include, "A comfort, a joy in ambiguity, in dealing with problems, being drawn to messy situations that are hard to solve...and the relentless ability to pivot from those learnings and to take a different direction."

131. Tech Entrepreneur and Investor Daren Cotter

Innovation. Drive. Purpose. Conversations with the enterprising entrepreneurs and leaders behind beloved and up and coming brands.

60. Sezzle Founder/CEO Charlie Youakim

Twin Cities Business

Related tracks