What does it take to bootstrap a tech company from the Midwest? Sit By Me founder, Bradley Steckart, knows all too well.
From jobs in government and financial tech to making the decision to quit corporate life, every path Brad has taken has led him to chasing his dream of getting Sit By Me off the ground.
Sit By Me is an app designed to foster connection in a time when people are feeling increasingly lonely and isolated. The app allows users to find other people who may be open to sharing a table at a coffee shop or may be looking to start a conversation with someone they don’t know.
It’s a great story, and one that’s unfolding still as we speak. Check out our Q&A with Brad to learn more about what it’s like building an app in the 414 and his aspirations for Sit By Me.
How did Sit By Me get its start? What was the inspiration for the app?
The idea for Sit By Me was conceived in 2018, and I acted on it when I started working remotely during the pandemic. I would want to get out of my house and go work from a coffee shop or bar and think, “what do all the other people here do?” or “I really like this place, what is it about it that I appreciate?” and shortly realized that it was the people within the spaces and valuable personal and professional connections I made that intrigued me.
I searched for a long time to find an app that helped make connections in real life, in real time, and there simply wasn’t one in existence. So I set out to build Sit By Me. Building the app helped me learn more about the loneliness epidemic, and the issues that arise from American loneliness. A large mission of Sit By Me now aims to help build community and connections in order to fight the loneliness epidemic.
What is your background?
For the past 7 years I have worked in Government Tech (Leading and Managing Customer Facing Teams), Government Finance, Financial Tech (sales), Financial Tech (Customer Success), Government Tech (Strategic Partnerships), and working as the Budget Manager for Washington County. Prior to my time in Tech, I received a degree in biology and was a freshwater biologist/ecologist.
How long have you been in business? Have you faced any major challenges with growing your business or any triumph stories?
We launched the most recent version of Sit By Me in February 2025. The idea has been in motion since 2018. 2020 is when I started testing the concept. I built a prototype in Milwaukee in 2022, and ttested that through 2023. I spent 2024 building the version you see today, and launched that February 22, 2025. Since launching we have grown from a simple concept to a community of thousands of people that want to meet others in real life, in real time!
Like many disruptive early stage companies, the biggest challenge we face is getting people to try something new. Building trust and changing social habits takes time! However, every time someone makes an IRL connection on Sit By Me, it reminds us exactly why we’re doing this. Our biggest triumph has been getting our Community Connection Points on board. Getting early adopters like ExpMKE at Wantable Cafe, Haven Cafe, Friendship Circle, and BizStarts on board has increased engagement on both sides!
Now the biggest challenge is continuing to get people to download the app and use it daily to make connections! It might feel new to bring up the app at a cafe or bar, and we envision a world where people can use their technology as a safety net to ease into real life conversations, friendships, and partnerships.
What is Sit By Me, and why did you feel it would be a good fit in Milwaukee? Or, why did you feel Milwaukee was a good place to start your business?
Sit By Me is a social engagement and connection app that helps people build their network and meet new people in real life, in real time. Sit By Me combats social media consumption and brings us back to IRL social interactions, so instead of scrolling endlessly alone or feeling awkward in a space, Sit By Me shows you cafes, bars, and community spots where people are open to meeting someone new in that moment. We call these spots Community Connection Points. People can also indicate if they are working quietly at Community Connection Points, allowing others to sit at the same table without interrupting their flow state.
Milwaukee is the perfect place to start and launch Sit By Me. Our city has a strong sense of community, but like many places this day in age, people struggle to connect with others in new spaces outside their existing circles. Milwaukee is big enough of a population to scale Sit By Me, and small enough that relationships, and word of mouth helps spread the message. Also – the local business community in Milwaukee is incredible and we’ve had really great support from them.
Launching in Milwaukee has allowed us to build an incredibly supportive network of users and local businesses that are engaged and are continuously using Sit By Me. From surveying hundreds of people and seeing the activity in the app, people are craving real-world connections, and Milwaukee has been the ideal place to prove that Sit By Me can deliver exactly that.
What’s the mission behind Sit By Me?
The Mission of Sit By Me is to connect people in real life, in real time to build networks, friendships, partnerships, and relationships. We exist to reduce loneliness, strengthen communities, enhance gatherings, and help build meaningful relationships through face-to-face interactions.
What is it like being a small business in MKE? If you’re a woman, minority, or LGBTQ+ owned business, please feel free to touch on your experiences as an entrepreneur in that space as well.
It’s an amazing experience to be a small business in MKE! As someone who has never defined themself as an entrepreneur, I have found this journey so rewarding. Can you say Small-waukee!? The startup community is thriving, and others are willing to help. I subscribe heavily to the phrase “a rising tide lifts all boats” and that couldn’t be more true in our city. Whether it’s MKE Tech’s FOR-M program, Gener8tor, Summerfest Tech, or other community gatherings, people are willing to help and boost each other up!
One challenge that I’ve experienced as an emerging tech founder in Milwaukee is that things move a little slower than on coastal cities with large amounts of investors into innovative tech. My observation has been that Wisconsin and Milwaukee knows what has been historically successful and can tend to stick to those types of industries. I’m excited to see more support for emerging technologies in the coming years to attract more innovation and keep new innovations in Milwaukee and Wisconsin’s economy.
As a startup, what has fundraising (if there’s been any so far) been like to try and get your movement off the ground?
The startup scene in Milwaukee is amazing! Up to this point I have been able to bootstrap Sit By Me, and have just recently started talking to investors about fundraising. That being said, I have opened a pre-seed raise to investors that closes on January 31st.
Aside from that, participating in pitch competition opportunities for small cash injections, like placing 2nd in Kenosha’s Pitch Perfect competition, or participating in Sheboygan’s StartUp World Cup qualifier have been helpful. There are also opportunities like the Wisconsin Technology Council’s Early Stage Symposium, as well as Grant opportunities from organizations like BizStarts, WBIIC, and MKE Tech Hub.
What do you like about being in Milwaukee?
Funny story about how much I love Milwaukee. In July 2023, my girlfriend (now wife), had an opportunity to travel to the east coast for a job opportunity. Neither of us have any family ties to Milwaukee, so we figured ‘let’s say goodbye to MKE and we’ll probably live on the east coast and never look back.’ Within 6 months of being on the east coast we were looking at how and when we could move back to Milwaukee. As Jeff Tweedy states, “Distance has a way of making love understandable,” and that was exactly our case. We missed the people, the connections, the lake, and especially the food.
What’s your favorite part about what you’re doing?
I’ve never been able to feel like an artist, as I’m not good with mediums like painting or drawing. Building Sit By Me has allowed me to inject who I am into an incredible app that helps people reduce feelings of loneliness and helps build up communities.
We’re at a time in our world where human connection is much needed, and yet we are so reliant on our devices. Being able to build something that threads the functionality of our app-driven world with the beauty of human connection feels like I’m creating a worldwide art instillation of human connection.
Where do you want Sit By Me to be in a year?
In one year, our goal is to have 50,000 users on the app, and have 100 Community Connection Points on the Sit By Me map.
What can people expect when using Sit By Me?
People can expect an easy login, spending about a minute making a profile, and setting your status to “open to chat’ or “working quietly.” Then exploring the Map to find Community Connection Points. You can see if people are at the Community Connection Points and then go there to find others to chat with! If you are working quietly in a busy spot, flip your status to “working quietly’ to let others know that even though you are heads-down, you don’t mind if they sit at your table and work quietly themselves!
Expect to make new connections in real life, in real time, and spend time connecting with other people that you may have never imagined. Expect to find a comfort in knowing that other people are willing to chat at café, bar, or third space, and all you need to do is pop on the app to find them.
Anything else we should know about your business or anything you’d like to mention? Any favorite stories?
We are eager to grow and connect Milwaukeeans like never before! If cafes, coffee shops, bars, events, conferences, libraries or any other third space with open seating is interested. We’d love to turn you into a community connection point!If you’re new to Milwaukee or curious about the app – give it a download! It’s free and you just might meet your next project partner, best friend, or significant other!