22: Rob Cressy’s Entrepreneurial Journey

rob cressy entrepreneur

The roles are reversed on this edition of The Rob Cressy Show as Greg Hunter is the host and Rob Cressy is the guest. G-Hunt delves into the entrepreneurial journey of Rob, how he got to where he is, the lessons learned, and how others can achieve their dreams.

In the candid conversation Greg Hunter and Rob Cressy have some of the topics they cover include:

  • How Rob went 1.5 years without a job right out of Miami (OH) University, living off his credit card, and what he learned.
  • The awful entry-level jobs Rob had, why he was thankful for them, and how they helped him appreciate what he didn’t want to do in life.
  • Dumb decisions that Rob made, which he wouldn’t recommend to others, but he somehow came out alright on the other end of.
  • How Rob’s online advertising career started because of the Pittsburgh Steelers and a Yahoo email address.
  • Rob’s habits for having a growth mindset.
  • How to be a high performing sales professional and paving your own way.
  • What lead Rob to quitting his job and becoming a full-time entrepreneur with Bacon Sports and Cress Media.

Feedback (I want to hear from you):

  • Is there something I can help you with? Have any thoughts or questions from our conversation?
  • Hit me up at rob@cressmedia.com or on Twitter @RobCressy and lets talk.
  • Also, if your brand isn’t on Snapchat yet then what are you waiting for? I can help get the right strategy in place. Hit me up.

Check out previous episodes of The Rob Cressy Show here.


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1. Ultimate Entrepreneur Reading List – I’ve read over 100 books on creativity, leadership, entrepreneurship, digital marketing, and sports that have had a major impact on my life. These are those books. Get your learn on!

2. Rob Cressy’s Guide To Being a Creator – Once you understand the Why and How, it all makes sense.

3. Want To Write Funnier? – For the last 4 years I’ve studied comedy writing at Second City and from one of the Co-Founders of The Onion. Learn how to become a funnier writer and take your business, career, or blog to the next level.

4. Follow Rob Cressy on Snapchat – If you are on Snapchat then you need to be following me faster than Antonio Brown can shake & bake a DB. You can also see my notes from the Snapchat For Business workshop I taught as well as what went down when I ran my first Snapchat geofilter campaign.

bacon sports snapchat

5. Ultimate Guide: Digital Marketing to Millennials – My 6 core principles for creating fun and engaging content that gets people to take action.

6. Subscribe to The Sports Marketing Huddle – My latest project is a podcast that takes a look at all things marketing in the world of sports.

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Inspiration  //  mindset  //  Podcast


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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.