While the path from a biology/ecology degree to government finance to founder of a tech company isn’t exactly straightforward, the experiences in between ultimately provided Brad Steckart with the tools to start Sit By Me.
The community-forward app is designed to bring people together by encouraging connection and fostering human interactions in public spaces like cafes, bars, or even libraries.
We talked more about Sit By Me in a previous write-up, but today, we wanted to learn more about Brad and what it meant to risk his corporate job to go all-in on a community-powered startup.
Let’s dive in!
What is your background?
I grew up in Wausau, Wisconsin, and made my way to Milwaukee in 2014 with a Biology and Ecology degree from UW-Stevens Point and a job studying freshwater ecosystems for the county parks. What started as a career move turned into something I didn’t expect. Milwaukee had a way of pulling me in. One opportunity led to another. I pursued a Master’s in Public Administration at UWM, transitioned into government finance, and eventually found myself as a Budget Manager for Washington County, deep in the world of technology tools and data. That combination of public service, finance, and tech is exactly what laid the groundwork for Sit By Me. The city didn’t just host my career. It inspired it.
Any stories from your youth that define your path?
I don’t think there was one single moment, but there was a clear turning point. When COVID hit, I was managing budgets for Washington County and ended up using a tech company’s software for contact tracing. That same company offered me a position on their team. From there, my career moved through several growing roles across government and finance technology, eventually leading to managing an Enterprise Customer Success Team for a major GovTech company. It was during that remote work chapter that the idea for Sit By Me was born. 75% of Americans are lonely, and one in four work remotely. While the flexibility of remote work is great, something is missing. A place to belong. A reason to be somewhere. I started building Sit By Me to solve that, and what began as a simple way to find friends at a coffee shop has grown into a platform shaping the future of human connection in cities around the world.
Where did you study (if you did higher education)?
UW-Stevens Point for Biology and Ecology, then UWM for my Master’s in Public Administration. But some of the most formative time I spent was as a grad student working from cafes and bars across Milwaukee’s Eastside and Riverwest. I didn’t know it then, but I was living the exact problem Sit By Me would eventually solve. I also spent a year in New Haven, Connecticut, home of Yale University. I never enrolled in a single class, but I spent the entire year hustling the concept of Sit By Me around campus hard enough that I ended up being invited to speak in Yale classes. I still mentor at Yale’s Tsai Center for Innovative Thinking today. Still not sure if anyone there knows I wasn’t a student. Sometimes the education that shapes you most is the one you weren’t officially enrolled in.
What do you do for work now?
Last September, I left a stable title, salary, and benefits to build Sit By Me full time. I am the Founder and CEO of a social engagement app that connects people to events, businesses, and each other, in real life, in real time. The honest pitch is this: the ROI of Sit By Me is human connection. Opening the app when you’re in line at a coffee shop, sitting at a bar, or working from a library isn’t a habit most people have yet. But it will be. And I’m building toward that future every single day.
Can you talk a little bit about your career journey? How’d you get to where you are now?
My career didn’t follow a straight line, but looking back, every pivot was pointing me toward the same destination. Science taught me to observe and ask better questions. Public administration taught me how systems work and where they break. Finance and technology taught me what’s possible when you combine data with design. And years of working remotely, often alone in a room full of people I’d never met, taught me what was missing. Sit By Me is the product of every chapter that came before it. I didn’t stumble into this. I built toward it.
Can you talk more about your community involvement?
Those who know me well have heard me say “a rising tide lifts all boats.” I mentor founders and entrepreneurs at Yale, UWM, Marquette, and MKE Tech Hub’s FOR-M Program, mostly helping people avoid the expensive mistakes I’ve already made so they can go make exciting new ones. I volunteer with Creative Mornings, give back through my church, and donate blood as often as they’ll let me. If I’ve figured something out that could save someone else time, heartbreak, or money, why wouldn’t I share it? Milwaukee has given me a lot. Pouring back in isn’t charity. It’s just good math.
What are some ways you have impacted the community in your line of work?
There’s a moment I’ve been lucky enough to witness more than once. Someone walks into a coffee shop or an event, opens Sit By Me, finds another user nearby, sends them an icebreaker, and suddenly two strangers are talking. Actually talking. Something I built helped write the first line of someone else’s story. That’s the whole reason. When you zoom out, Sit By Me isn’t really a tech company. It’s a human connection company that happens to use tech. And every new connection made on the app is proof that we’re onto something real.
What do you like about living in Milwaukee?
My wife and I actually left Milwaukee a couple of years ago, moved to the East Coast, and thought we were chasing something bigger. Six months later we were aching to come back. That’s Milwaukee for you. It sneaks up on you. The lake beats the ocean by far, though I do miss the oysters (Zebra mussels just don’t have the same panache). The food scene punches above its weight. Neighbors who actually know your name. A city that’s perfectly sized, big enough to surprise you and small enough to feel like yours. Milwaukee is a place that earns your loyalty quietly, and then you realize it’s been home all along.
What do you want to see for Milwaukee’s future?
Milwaukee is quietly becoming one of the most strategically important cities in America, and most people haven’t caught on yet. Fresh water is the resource of the future, and we’re sitting on 20% of the world’s supply. The tech scene here is growing fast. LinkedIn ranked us a top 5 fastest-growing metro for career growth in 2025. Summerfest Tech is becoming the Midwest’s answer to SXSW. The Walker’s Point Innovation District is just getting warmed up. We didn’t come back to build in Milwaukee despite building a world-class tech company. We came back because of it. The Midwest is where it’s happening. We’re just early.
Anything else we should know about you, your job, community involvement, or life in general?
On Friday, June 6th, Sit By Me is throwing the V3 Launch Party at MobCraft Beer, and Milwaukee is invited. V3 is the biggest update in our company’s history, making real-time, in-person connection faster and more intuitive than ever. We’re celebrating with live music, MobCraft’s finest craft beer, and some of Milwaukee’s best founders, entrepreneurs, and builders. Every $10 ticket includes a free drink and a free month of Sit By Me Premium. The first 50 tickets are 2-for-1. This party isn’t just about an app update. It’s a celebration of what Milwaukee is becoming and proof that world-changing technology is being built right here in the Midwest.
Grab your tickets here, download Sit By Me on iOS or Android, and follow us at @sitbymeapp. Come sit by us.