Thursday, November 10

8:30 - 10:00pm Rosen Shingle Creek Sebastian Ballroom

The IT Nation is all about fostering community in the TSP space. In that spirit, we honor and celebrate the online communities that foster dialogue, peer support (in poetic prose!), and comradery in the digital sphere. At ConnectWise, we get a real kick out of the witty and whimsical rhymes that often make their way into online forums. So what better way to have fun at this year’s IT Nation Connect event than to have our VERY OWN <amateur> RAP BATTLE!!!

We’ve teamed up with friends: 7 Figure MSP, ConnectWise Boss, ConnectWise Tips & Tricks, MSPGeek, r/msp, and the ConnectWise Virtual Community to bring you a fun-filled night where each community will select a local lyricist as their champion to battle it out against other community champions…and dare we say ConnectWise’s mystery rap battler as well! Applaud the rhymes, cheer on your favorites, and catch prizes!


Who will take home the trophy for 2022? Join us to find out!

Rappers from each of our partnering communities will compete in a bracket-style format. Each competitor will have 60 seconds to dazzle the crowd with their lyrics and performance over multiple rounds of competition. 

In addition to the rappers, you can also enjoy:

  • Live commentary from community influencers during the event
  • Unique performances by special guests
  • Closing celebrations, prizes, and discussions of glory

Partnering Communities:

Rules of Engagement

The Rap Battle is a fun, personable event; 
We want it to be good – time well spent!

Be sure your rhyme reflects who you are;
Don’t get kicked out by being a liar.

Profanity and inappropriate lyrics? We will not tolerate.
We will dismiss anyone who makes the community irate. 

So don’t bash your competitors, or your peers;
Instead, bring in good rhymes; we’re ready, all ears.

These rhymes may entice you to do a mic drop,
Just use the hand gesture, so the equipment won’t flop!

 We are excited to see your skills on a cool stage,
And all the IT Nation sparks this event will engage!


The Rap Battle is designed to bring some of our various online communities together for an evening of playful lyrical banter. As with all our events, we strive to create a respectful, inclusive environment. While we are offering to coach and work with rappers to preview their content to ensure it aligns with our guidelines, we will remove any competitors or audience members who are being disrespectful.

Full terms and conditions of the IT Nation Amateur Rap Battle by ConnectWise + Friends.