Ep 000: Welcome To The Rob Cressy Show

rob cressy show

Welcome to episode 000 of The Rob Cressy Show! Through unique experiences as an entrepreneur, content creator, and digital marketer I have gained valuable knowledge that I want to share with you in a fun and engaging way to help make your professional and personal life better.

From studying improv and comedy writing at Second City, to throwing 700+ person events, to creating 1000’s of podcasts, articles, and videos, to overcoming objections selling online advertising for one of the Top 100 most visited websites. My experience is as vast as the passion that burns inside me.

While on this journey I have met some incredible creators, entrepreneurs, and marketers who have knowledge and wisdom that I’d love to share. Each week I will have candid conversations about things they are excellent at with the goal of teaching, inspiring, and entertaining you.

This initial podcast gives an overview of what you can expect from The Rob Cressy Show, the frequency at which I’ll be dropping shows, and what the overall theme is.

I’m very big into building community and having others part of what I do. I am on a journey of engagement and constant improvement and your feedback is important to me. Because of this I want to hear from you. Are there things you like or don’t like in the show? Topics you want to hear more about? Guests you’d like to see? Did something talked about on the show encourage you to take action? Whatever is on your mind let me know.

You can connect with me on Snapchat @baconsports, on Twitter @RobCressy, on Facebook @CressMedia, shoot me an email to rob@cressmedia.com, sign up for my weekly Monday Morning newsletter, or check out the awesome content on the Cress Media blog. I appreciate you taking the time to be part of my newest venture and I look forward to having fun with you.



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1. Learning at Second City and the Power of YES AND – One of the comedic fundamentals and building blocks for improv. The power of YES AND has a way of completely transforming your outlook on comedy and life.

2. 11 Funny Filters to Write Jokes – Every joke created uses at least one of these 11 funny filters. When writing comedy use these funny filters and you’ll quickly see improvement in your jokes. These come straight from my Writing for The Onion class.

3. 21 Comedy Writing Tips – These comedy principals are building blocks for the rest of your comedy writing and no doubt will help increase the quality of your jokes and writing. These also come straight from my Writing for The Onion class.

4. Follow Rob Cressy on Snapchat – If you are on Snapchat then you need to be following me faster than Seabass can throw one down.

bacon sports snapchat

5. Monday Morning Newsletter Get rid of your case of the Monday’s with Rob Cressy’s weekly Monday Morning newsletter. It’ll give some extra motivation and inspiration to those who strive to do great things.


  • To help give more context into who I am and how I roll I thought it would help to give a list of some of my influences: Gary Vaynerchuk, Tai Lopez, John Lee Dumas, Tim Ferriss, Andrew Warner, Bill Simmons, Dan Patrick, Jalen & Jacoby, Jay Mohr, Brian Koeppelman, The Chive, Second City Training Center.
  • You should check out my Ultimate Entrepreneur Reading List. It contains over 100 books for entrepreneurs, creatives, hustlers and sports fans that want to be great.




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Sports Content Studio

Cress Media is a Chicago Sports Marketing Content Studio. We help brands activate sports fans by telling their story in a fun and engaging way via audio, video, and social content creation. We get your audience talking, taking action, and having fun with your brand online and offline. Whether in Chicago or any other part of the country Cress Media can handle your content creation and sports marketing needs.