Jack Pawlik and the education of a six o’clock barista

At six in the morning, Jack Pawlik went to work at Cafe Social in Madison, Wisconsin. He was building a software company, and his chosen research instrument was a barista shift. He worked for free. For months, the counter became a place to discover what a product demonstration could politely conceal: the button in the wrong place, the feature that made sense until somebody actually needed it.

He finished at four in the afternoon and passed his observations to his co-founder, Avery Durrant, who made changes overnight. The next morning brought another shift and another chance to find out whether the changes helped. There is something pleasingly inconvenient about this method. A customer can nod through a presentation. A working coffee shop has orders to finish.

Dripos began in 2019 as a mobile ordering app. The more Pawlik talked with owners, the more he understood that another app could add to their difficulties. The business grew around a larger proposition: bring the work of running an independent coffee shop into one system. His education behind the register gave that proposition a daily examination.

A dorm room with a dispatch problem

Pawlik’s first practical lessons arrived before Dripos. In 2015, while entering the University of Wisconsin-Madison, he joined EnvoyNow, a food delivery startup founded by University of Southern California students. He and his roommate, Max Schauff, helped bring it to Madison. Running a local service meant finding restaurants, organizing drivers, marketing, and making sure orders reached people.

In his later account of those days, Pawlik described tracking orders at night and sometimes getting on his bicycle to deliver them himself. The distance between management and delivery could be measured by the time it took to leave the dorm. That experience puts a useful perspective on the word “platform.” Somewhere beneath the interface, someone still has to collect dinner.

Pawlik’s academic field was real estate and urban land economics. The work he kept choosing involved the movement of people, orders, and money through local businesses. Those subjects have more in common than a university prospectus might suggest. A business occupies a place, but its success depends on what happens inside it and how easily customers can take part.

The queue outside Whiskey Jacks

In February 2017, a line formed outside Whiskey Jacks Saloon in Madison. A cheap beer promotion helped. So did an email sent to a student audience Schauff had assembled during the delivery venture. Schauff and Pawlik were trying out LineLeap, which let customers buy a pass to skip the line at participating bars.

The scene offered a rather literal business problem: people wanted to get through a door. The product attached a price and a mechanism to that wish. An unglamorous bit of previous work, building an email audience, helped the new venture find customers. Their first company had left them with knowledge of the town and a way to reach it.

Pawlik subsequently worked on Cork Drinks, a drinks subscription service. These businesses were related through the places they served, although they solved different problems. The pattern helps explain his eventual interest in coffee shops. He had already spent years learning how hospitality businesses attract customers and turn an idea into something that can be purchased.

On sales trips for Cork Drinks, he made the constraints unusually tangible. Pawlik converted the passenger seat of his 2005 Acura TL into a bed, avoiding nightly hotel bills while signing up partners. He called the car the Salesmobile. The name had rather more charm than the accommodation, but the arrangement let him keep visiting the businesses he hoped to serve.

“I like building things.”

Jack Pawlik · LinkedIn profile

That is how Pawlik describes himself on LinkedIn. It is a modest job description for somebody whose college years included several startups, but also a precise one. His record keeps returning to the moment when somebody uses the thing. A line outside a bar and an order arriving at a café provide answers that an attractive slide cannot.

The prize came before the wider problem

In March 2019, Pawlik and Durrant launched Drip at Cafe Social and Fair Trade Coffee House in downtown Madison. The original offer borrowed a convenience familiar from large chains: ordering and paying from a phone. Independent shops could offer customers some of the same digital habits without having to build the underlying technology themselves.

The following month, Drip won the $15,000 top prize at the Transcend Madison Innovation Competition. The award included a visit to Qualcomm and a year’s membership at StartingBlock, Madison’s entrepreneurial hub. More than 30 teams had brought prototypes and business plans to the competition. Pawlik was a senior, already presenting a product people could download.

The university also awarded him the Alan C. Filley Outstanding Undergraduate Award in 2019. He graduated that May with a BBA in real estate. A university competition supplies money and a deadline, two useful correctives to a project that can otherwise remain forever almost ready. Drip had crossed the more consequential threshold of being used outside the classroom.

Winning for the original product did not settle what the business should become. Software can perform its assigned task and still leave the customer with too much work. For Pawlik, finding that larger problem required taking the owner’s view of a whole day, rather than treating a mobile order as the beginning and end of the job.

The business behind the cup

A coffee shop’s visible transaction is brief. Behind it sit staff schedules, pay, customer records, payments, and the administrative work of keeping the business running. Different tools can handle each task, yet the owner still has to make them cooperate. Every additional handoff creates another place where somebody may need to check or move information.

Dripos’s answer was to bring those functions together. The company’s 2024 funding announcement described shops juggling five to ten software products. Its pitch covered point of sale, mobile payments, employee management, payroll, loyalty, and marketing. For Pawlik, the customer relationship had expanded from helping someone sell a drink to helping them operate the business that sold it.

There is a practical burden hidden in that ambition. The more jobs a system takes on, the more ordinary moments it must handle well. Scheduling and paying a team are recurring obligations. A founder who asks owners to consolidate their work is also asking them to place more trust in one company. Ease of use carries a considerable amount of responsibility.

A bigger company, measured in shops

In April 2024, Dripos announced an $11 million Series A led by Base10 Partners. The company reported that its number of locations had increased 400 percent during 2023 and that it was operating across 46 states. Those figures describe a business moving well beyond the two Madison cafés where its earlier product began.

Caroline Broder, the Base10 principal who led the investment, joined the board. The connection placed Dripos within the firm’s interest in software for everyday economic activity. For an independent café, that activity is wonderfully concrete: employees arrive, customers pay, and somebody has to make the records add up when the doors close.

Pawlik’s own public hiring message emphasized that employees could see their work being used in the world, from registers to payroll. That continuity matters to his story. His responsibilities had grown, but the attraction he described was still attached to real people using a product. The company could recruit engineers by pointing to an actual counter.

What January 2026 looked like

By January 2026, Pawlik said Dripos had crossed 1,000 live coffee shops. He wanted to reach 10,000. The first figure was a milestone; the second was an ambition. Keeping the distinction clear makes the ambition more interesting. A company serving a thousand shops already has a substantial number of working days to get right.

That month he introduced a refreshed brand and Counter Talk, a publication for the coffee industry. His accompanying plans included integrated accounting and a workflow for cash rounding. The subjects sit at opposite ends of the scale: a company explaining its identity, and a shop working out the amount due at the register. Both belong to the business he is trying to build.

The accounting work continued the same logic. Dripos partnered with Layer to bring accounting software and bookkeeping into its platform, connecting sales and labor information with financial records. The promise concerned work that happens after a customer leaves. A receipt is the end of one interaction and the beginning of somebody else’s administration.

A cortado, and more work tomorrow

Away from Dripos, Pawlik’s January 2026 introduction placed him in New York with his partner, Pia, and their adopted dog, Remy. He described snowboarding, bouldering on the Lower East Side, and a fondness for trying restaurants. His coffee choices included an iced americano, an almond milk cortado, and drip coffee in a chunky ceramic mug.

The mug is a small but useful detail in a story full of software. A coffee business sells a physical experience, down to the vessel somebody likes holding. The systems behind it earn their place by helping that experience happen. Pawlik’s career has repeatedly brought him back to businesses where the evidence is available across a counter.

His stated long-term intention was to keep listening to operators and building with them. That leaves room for changes in the product, as it should. Dripos’s own history includes a useful change of mind about what customers needed. The morning shift remains a persuasive standard: put the idea to work, watch where it slows somebody down, and return with something better.