Today we’d like to introduce you to Freddie Kole.
So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
Fourteen years ago I was bartending at a small bar in Northbrook & I started a college night with the hopes of bringing in more customers. The college night was an instant success and I figured I should try to do something similar in the city to see if it worked, and it did.
The following year, after graduating from the University of Illinois, I continued to throw events as a part-time hobby. I enjoyed bringing people together and showing them a good time, the more events I threw the more I learned and the more I learned the more profitable I became. In 2008 I started making more money at my “part-time” job than I was at my “full-time” job and I decided to quite trading to focus all of my attention on Chicago Twenty Something.
Over the past 9 years the growth has been incredible. We throw hundreds of events each year ranging from bar crawls & booze cruises to donut fests. We also plan private parties like corporate events, birthdays, reunions & fundraisers via ChicagoPartyBooker.com
Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
There have been numerous struggles along the way. I’ve sacrificed countless weekends, dealt with dis-honest partners etc. Being an entrepreneur is tough, you have to do everything you can to keep your costs low…including cleaning the bathroom in your office instead of hiring a cleaning crew.
Chicago Twenty Something – what should we know? What do you guys do best? What sets you apart from the competition?
We are known for our bar crawls (The Mustache Crawl, The Chicago Shamrock Crawl, Country Crawl etc.) Booze Cruises & our festivals. Nothing makes me more proud than seeing thousands of people enjoying the events we produce. I think what sets us apart from the competition is that we put together hundreds of events each year and we do so in professional manner.
What moment in your career do you look back most fondly on?
The success of The Mustache Crawl. Last year we had over 8,000 attendees and raised over $25,000 for local charities.
Contact Info:
- Website: ChicagoTwentySomething.com, ChicagoPartyBoat.com & ChicagoPartyBooker.com
- Email: info@chicagotwentysomething.com
- Facebook: www.facebook.com/ChicagoTwentySomething/
- Twitter: https://twitter.com/Chi20Something

