Jack Pawlik

Yo, so let me tell you about Jack Pawlik. This guy’s a straight-up startup machine. He’s from Wisconsin, got his degree in Business from Madison, and just jumped right into the hustle. His whole thing? Building tools that actually help small businesses crush it, especially coffee shops and restaurants.

He first popped on my radar with LineLeap, which was part of YC S19. That was his first big move, and you could tell he’s the kind of guy who’s hands-on. He was all about marketing, getting customers in the door, making sure the product actually worked for real people. And it paid off, LineLeap did well enough to catch YC’s attention and set him up for the next chapter.

Fast forward, Jack co-founded Dripos, and this is where he really hit his stride. It’s based in NY, and he’s running this all-in-one platform that’s basically replacing the clunky old POS systems, payroll, scheduling, the whole shebang. And man, did he crush it. They grew super fast, now in 46 states, and just raised $11 million in Series A funding. That’s no small feat. It’s like he’s building the future of how coffee shops and restaurants run behind the scenes.

What’s crazy is how he’s so hands-on with his clients. He’s not just the guy behind the scenes, he’s out there helping with onboarding, tweaking features, making sure the product actually solves real problems. That kind of grit, actually caring about the end user, that’s what sets him apart.

Looking at his process, it’s pretty clear he’s driven by more than just making money. He’s into making tools that actually make a difference, helping small biz owners not get crushed by tech bullshit. His experience with LineLeap and EnvoyNow shows he’s always been about the hustle, about building stuff that’s the real deal, not just bullshit.

So yeah, Jack’s a legit example of what it means to jump into startups with no fear, learn as you go, and keep pushing until you build something that matters. He’s the kind of founder you want to watch, smart, super practical, and genuinely passionate about making life easier for the people who keep society running day-to-day.