4 startups in, UW senior has no plans to stop building

Jack Pawlik, 22, and his partners launched his fourth startup this month — drip, a mobile app similar to Starbucks’ but focused on local cafés.

One example does not a trend make, but Jack Pawlik is proving that the entrepreneurial spirit is alive and well at UW–Madison.

Pawlik, a 22-year-old senior majoring in real estate, is already on his fourth startup, and the latest one is capitalizing on the popularity of Starbucks’ mobile app but with a focus on local coffee shops.

Drip co-founders Jack Pawlik (left) and Avery Durrant.

Pawlik, along with co-founder Avery Durrant, launched drip earlier this month, offering local coffee shops a new app-based ordering and payment system to help them compete with large chains.

“Starbucks now receives almost 40 percent of its orders from customers using its mobile app, and the Starbucks app is also the most-used payment platform in America, used more than even Apple Pay or Google Pay,” says Durrant, CTO of drip.

“Local shops don’t have the tens of millions of dollars that the national chains have invested in these systems, so we stepped in to produce a system they can use to help them compete. We know drip will help them level the playing field.”

Pawlik and Durrant launched drip last week at two cafés in downtown Madison — Café Social, a coffee shop near the Kohl Center, and Fair Trade Coffee House, a café located on State Street.

“Not only am I hoping to bring my customers a more convenient option, but I hope to attract new customers, as well,” says Omar Lopez, the owner of Café Social. “So far drip has been very easy to work with.”

The drip team says there’s already been an influx of customers using the app at their first cafés, and a number of additional coffee shops in Madison have also joined the platform and plan to go live this month. Additionally, the two students say they have begun marketing the product in five additional cities.

“Our goal is to create a unified network of local cafés that as a whole can compete with these national chains,” notes Durrant. “It’s been very exciting to work on.”

‘I like building things.’

Though he’s only been living the entrepreneurial life for four years, Pawlik’s trajectory for startup success is remarkable.

Pawlik grew up in Minneapolis but moved with his mother to Madison for his senior year in high school. She moved again after he graduated, but Pawlik stayed in Madison as an incoming freshman at UW. That summer of 2015 was when he got involved with his first startup, a food delivery company called EnvoyNow.

“It was founded by four students at USC and I randomly stumbled upon them one day while searching around the internet,” explains Pawlik. “They got a chance to do an impromptu pitch to Mark Cuban, who totally destroyed them, but then Mark Burnett, the producer of Shark Tank, offered them $100,000 on the spot.”

Pawlik reached out and became the first person on the EnvoyNow team outside of the founders, eventually convincing one of his good friends to join, as well. That summer, as EnvoyNow started up in San Francisco, Pawlik and his friend were in charge of opening up the Madison market. “We hired/scheduled all the drivers, signed on our partnered restaurants, marketed the service, and routed the orders every day. Basically we were in charge of everything but the tech. That fall, Envoy launched a total of eight markets, and my good friend and I had Madison doing more orders than anywhere else.

“We were given ownership in the company and led the expansion from eight to 25 delivery markets over our winter break,” says Pawlik. “At the time, I thought this was a pretty normal experience, but looking back it was crazy as we were managing all of this out of our dorm room. I definitely had no idea what I was doing, but it was super fun to learn on the fly.”



That spring, Pawlik says, the team was able to raise a couple million dollars in venture capital funding, the company’s CEO became a Thiel fellow, and EnvoyNow received an additional investment from the Founders Fund, a San Francisco-based venture capital firm investing in companies building revolutionary technologies. “We spent the summer out in San Francisco living in the stereotypical startup house where we worked/lived,” recalls Pawlik. “It was pretty glamorous — we slept on mattresses thrown on the floors and then moved tables in during the day. We went on to get acquired by JoyRun that next fall. We probably did every single thing wrong that we could have over the course of the company, and it was a total crash course in the startup world.”

Shortly after, Pawlik helped launch two nightlife startups. He co-founded LineLeap with three others, which partners with busy bars that get lines out their door. The platform sells fast-pass tickets that allow customers to “leap” the line. In the last two years, the LineLeap team has partnered with bars in 15 cities, and the young company won last year’s Transcend business competition in Madison, as well as other business competitions on other campuses.

Following the success of LineLeap, Pawlik saw an opportunity and launched a complimentary product called Cork Drinks, an app that provides bars and restaurants with a way to offer a subscription to drinks for their customers. Cork Drinks is now live in three cities.

Pawlik's "Salesmobile."

“To scale the company, I converted the passenger seat in my 2005 Acura TL into a bed because we didn’t have the money to spend on hotels every night,” notes Pawlik. “I drove between markets signing on new partners, sleeping in my car, and using a Planet Fitness membership for my high-class ‘amenities.’ We call it the ‘Salesmobile.’”

Between LineLeap and Cork Drinks, Pawlik has been through a lot of the Madison startup ecosystem and participated in both MadWorks and gBETA. “It’s pretty cool to see Madison providing all these resources to startups. I never set out to start all of these companies, but these great ideas kept popping up that had the potential to piggyback on each other, and I fell in love with the process of building an early-stage business.”

With all of his ideas, Pawlik saw a similar concept working well elsewhere and adapted it for a broader marketplace.

LineLeap was an idea that Pawlik and his partners saw working at one bar in Michigan. “We had this network built out from EnvoyNow and thought we would be able to use the same model to expand quickly,” he explains. “With Cork Drinks, I was working on getting LineLeap established in New York and saw a company doing similar drink subscriptions. The thought was similar to use the network we had built with LineLeap and add this on as a complimentary product.

“The idea for drip slowly transformed from being a similar subscription option as Cork Drinks into more of the mobile ordering platform it is today. The more we looked at Starbucks and how much success their app has had, the more we figured that these were tools local cafés should have access to, as well.”

So far, what Pawlik is doing is paying off. While EnvoyNow was acquired, the other three startup businesses are profitable at the moment, though Pawlik notes almost all profits get reinvested into growth at this stage. “I’ve gotten pretty good at embracing the ‘lean’ lifestyle, trying to live and work as cheaply as possible (i.e., the Salesmobile).”

In order to balance the early growth and success of the businesses with his busy college schedule, Pawlik has had to make some other sacrifices, as well — namely on how he spends his “free” time. “[But it’s] never felt like I’ve been making sacrifices because working on these startups is something I really love to do,” he explains.

“I like building things. It’s one of the most rewarding processes to see something you built out in the world and being used, and hopefully I am lucky enough to keep doing it.”

drip Basics

  • The app is available on both Android and iPhone.
  • To order, a customer uploads money onto an in-app card, selects the café they want to order from, selects the menu items they want, and then pays through the app. The order gets sent to a tablet at the café and once the order is ready, the user receives a notification on his or her phone.
  • The reward system gives two “beans” for every $1 spent at any café on the app. Once a customer reaches 100 “beans,” they can redeem them for a free item of their choosing.
  • Implementation for a coffee shop takes 10–20 minutes. All the café needs to do is set up the tablet that drip provides them and then input their menu into the app. There is no up-front cost or monthly fees for a café to use the platform.
  • A café does not need to change its POS system. Drip is a separate addition that integrates easily.
  • Drip provides all first time customers with $1 off their first order at a participating café.

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