CitySwarm
After you quickly sign up and create a profile, CitySwarm sends you their weekly newsletter detailing their upcoming events. Whether it’s a Cubs game, a craft beer tour, or a sailing trip, CitySwarm has a wide variety of events that provide hassle-free entertainment to young Chicagoans looking to explore the city and meet new people. I caught up with CitySwarm’s founder Lindsay Saewitz to discuss her entrepreneurial journey as well as the ins and outs of running a company like CitySwarm.

We use a variety of ways to get the word out. Our weekly email is the primary way we get our events out there, and then we supplement that with social media and posting it on a variety of event sites.
Q: What has been the response from the venues hosting CitySwarm events?
Overall very positive. We feel like we're delivering valuable marketing exposure at low-to-no cost, and our partner venues have echoed this sentiment.
Q: What unique features about Chicago make it the perfect place for an idea like CitySwarm?
The sheer size of the young professional demographic make it a great place, but of course beyond that is all of the amazing things there are to do. With the change in seasons there's always something festive going on, and a new bar or restaurant opens every week.
Q: Do you envision expanding CitySwarm to other major cities going forward?
To be determined:) In my mind I can see a CitySwarm in every city, but getting to that point would certainly be a challenge.
Q: Did you ever plan on becoming an entrepreneur?
Nope...I always envisioned myself at a large corporation, which is where I began right out of college. There's things I really like about that environment, and I may end up there again one day, but I really wanted to take a gamble and start my own business. I felt that it was the right time, and that if I didn't do it when I did I would have regretted it.
Q: What ways in particular did your marketing and online sales background help you grow your business?
It was everything. When I graduated college, the last place I thought I would be at was in an entry level sales position making 125 cold calls a day. But it taught me how to do business and how to sell - essential to anyone starting a business. My marketing skills helped me create a brand and grow the list, and communicate the value to businesses.
Q: What has been the biggest challenge of running your own company?
For me personally, it's been being alone without much help or support from colleagues or a mentor. I've said in other interviews how I like working alone, which I do, but what I do miss is the camaraderie and emotional support of a team. I've been lucky to find some awesome people in the startup community who keep me sane, though!
Q: What are some upcoming CitySwarm events you are excited about?
I love our fall events, specifically Sunday Funday on the Farm. Everyone gets decked out in boots, cowboy hats, and plaid - and it's just so fun spending the day outside the city. In general November and December are pretty festive, so I like that our events like the Thanksgiving Cooking Class and Holiday Trolley help celebrate the season.