Creator & Entrepreneur Newsletter

Try not to become a person of success, but rather a person of value. – Albert Einstein Through unique experiences as an entrepreneur, creator, and digital marketer I have gained valuable […]

Ultimate Entrepreneur Reading List

This is my Ultimate Entrepreneur Reading list. A list of books for entrepreneurs, creatives, marketers, hustlers and sports fans that want to be great. Reading first thing in the morning for […]

Podcast Hustle: The Step By Step Guide Of How To Start A Podcast & Grow An Audience

Do you want to start a podcast? If so you are in luck! Rob Cressy, marketing expert, content creator, and Founder of Bacon Sports, who has published 500+ podcast episodes […]

Tips For Storytelling, Prospecting & Digital with Jordan Scheltgen (Ep 39)

Jordan Scheltgen, CEO & Founder of Cave Social, joins the Rob Cressy Show to tell an awesome story about using his creativity and having the balls to take a leap which […]

Huntz Colburn – Monkey Pickles (Ep 38)

Huntz Colburn, Founder of Monkey Pickles, joins the Rob Cressy Show to talk about doing what you love, building a community, the role of humor in business, how to choose who to […]

Lucas Guariglia – Rowboat Creative (Ep 37)

Lucas Guariglia, President of Rowboat Creative, an apparel production company, joins the Rob Cressy Show to talk about his entrepreneurial and success mindset, self accountability, knowing who you are, having the belief and […]

Simply Standout with Jessica Zweig (Ep 36)

Jessica Zweig, Founder and CEO of The Simply Be Agency, a personal branding agency that specializes in the art of standing out, joins the Rob Cressy Show to talk about using […]

Jens Nicolaysen – Shinesty Co-Founder & CMO (Ep 35)

Jens Nicolaysen, Co-Founder and CMO at Shinesty, joins the Rob Cressy Show to talk about how they create the world’s most outrageous apparel for everyone and believes life’s too short for […]

Kenny Powers & Exceeding Expectations w/ Ceo Wimmer (Ep 34)

Ceo Wimmer, President of CayRay Group, an award winning global sports, entertainment, media and marketing agency, joins the Rob Cressy Show to talk about lessons learned from the program he worked […]

Social Media Enthusiast Shantel Khleif (Ep 33)

Shantel Khleif, Social Media Enthusiast & CEO of Imagine Media Consulting, joins the Rob Cressy Show to talk about social media marketing, brand storytelling, plus share lessons from her entrepreneurial journey. What […]

Ryan Stewman Spitting Entrepreneurial Fire (Ep 32)

Ryan Stewman, CEO and Founder of Hardcore Closer and Break Free Academy, joins the Rob Cressy Show to spit fire about his incredible entrepreneurial & sales journey, sharing lessons learned on the way. […]

31: Seth Shapiro – Diesel Films

Seth Shapiro, CEO of Diesel Films, joins The Rob Cressy Show to talk about lessons learned along his entrepreneurial and creative journey. He talks about his early days of what it […]

Building The First Sports Betting Snapchat Account

Welcome to a case study about how I created the industry’s first sports betting Snapchat community for Lets start at the beginning. I love Snapchat and I love sports. When looking […]

Logos & Graphics: Clean, Crisp Mashups

Everything you do is a reflection of your brand, so it is paramount that you create high quality logos and graphics. At Cress Media we take pride in the fact […]

Barstool Sports CEO Erika Nardini on Community & Content

Erika Nardini, CEO at Barstool Sports, joins Rob Cressy and Brian Cristiano on The Sports Marketing Huddle to talk about Barstool’s thriving community, creating engaging content, and paths for monetization. […]

Sports Marketing Huddle: A Podcasting Case Study

In a digital landscape where brands are constantly competing for the attention of their customers, there is a hidden gem that when executed correctly can be an effective and valuable […]

30: Hustle, Comedy & Building Relationships with Lyle Pinder

Lyle Pinder, writer, producer, podcaster, and head of AuVi Digital, joins The Rob Cressy Show to talk about his hustle, entrepreneurial mindset, lessons learned on his journey, how he thinks […]

Bacon Sports: A Content & Engagement Case Study

We know that time and budgets can be tight. That’s why it’s so important for the content and social media marketing you create to deliver the results you are looking […]

29: Turning Ideas Into Action with Sam Rosen

Sam Rosen, Founder of Deskpass and One Design Company, joins The Rob Cressy Show to talk about lessons learned on his entrepreneurial journey, how he used to sell rocks for money, […]

28: Comedy, Sports & Business w/ Law Smith

Law Smith, comedian, podcaster, and President at Tocobaga Consulting joins The Rob Cressy Show to talk about his success mindset, how standup comedy helps break down fear barriers, and how […]

27: Sports Agents, Sacrifice & Success with Ashley DeWalt

Ashley DeWalt, CEO of Fusion Sports Group, joins The Rob Cressy Show to talk about the hustle and sacrifice it took to build his company and begin working with professional […]

26: Dreaming Big & Dealing With Fear With Ric Gruber

Ric Gruber, President & Creative Director at Brandless, joins The Rob Cressy Show to talk about being a creator and getting paid for it, dreaming big and following your passion, dealing with […]

25: Super Bowls, Emmys & Sports with Jacob Ullman from Fox Sports

Jacob Ullman, Senior Vice President of Production and Talent Development at Fox Sports, joins The Rob Cressy Show to share wisdom from working on six Super Bowls, winning seven Emmys, […]

24: Having a Creative Mindset with Robin Gruen

Robin Gruen, Creative Director at Motiv8 Agency, joins The Rob Cressy Show to talk about having a creative mindset. Robin is a bundle of creative awesomeness. In our conversation she shares […]

23: Optimizing Your Life with Emerson Spartz

Emerson Spartz, CEO of Dose, joins The Rob Cressy Show to share insight into ways he’s optimized his life to get better results and you can too. Emerson was named to both Forbes’ and Inc […]

22: Rob Cressy’s Entrepreneurial Journey

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 […]

21: Startup Success and How You Can Achieve It w/ Jim Phillips

Jim Phillips, General Manager of Chicago at Ritual, joins The Rob Cressy Show to talk about startup success and how you can achieve it. Jim has been in the startup game […]

Rob Cressy’s Guide To Being A Content Creator

Welcome to Rob Cressy’s Guide To Being A Content Creator. My mission in life is to be happy doing what I love. I love creating, growing, learning, engaging, having fun, […]

20: Sage Summit 2016 Recap- Holy Amazing!

Greg Hunter joins The Rob Cressy Show to recap our incredible experience at Sage Summit 2016, a conference for entrepreneurs and small & medium-sized businesses. Speaking at the conference was an A-list of […]

Creative Snapchat Tips To Take Your Game To A New Stratosphere

One way to turn an ordinary Snapchat picture, video, or story into something that makes you say WHOA! is by adding a little creativity to it. Not only does it make […]

19: Award Winning Sommelier Liz Mendez Talking Snapchat Strategies

Liz Mendez, an Award Winning Sommelier and owner of Vera Chicago, joins The Rob Cressy Show to talk about Snapchat strategies and tips for using the platform to grow your business. Liz […]

Sage Summit Day 3: Ashton Kutcher & the CEO of Kickstarter

Day 3 of Sage Summit was the victory lap. After an incredible first two days that saw Richard Branson, Daymond John, and Robert Herjavec take the stage coupled with The […]

Sage Summit Day 2: Wisdom From Shark Tank & Hollywood

Day 2 of Sage Summit 2016 had a lot of expectations to live up to following Richard Branson dropping some major wisdom bombs on day one. Thankfully the lineup of speakers […]

Sage Summit Day 1: Richard Branson Inspires & B1G Media Day

Today was the first day of Sage Summit, a conference for entrepreneurs and small & medium sized businesses, which is filled with tons of learning, training, and networking opportunities. I didn’t now […]

WOWZA! Results From My First Snapchat Geofilter Campaign

This past weekend I completed my first Snapchat geofilter campaign for Bacon Sports and boy am I excited! This article is going to talk about my experience, detail the Snapchat geofilter […]

18: Pete Vlastelica’s Yardbarker Journey

Pete Vlastelica, EVP of Digital at Fox Sports and Founder of Yardbarker, joins The Rob Cressy show to talk about his entrepreneurial journey building Yardbarker. Pete shares how he went from […]

17: Launch of The Sports Marketing Huddle

I’m excited to announce the launch of my newest project, The Sports Marketing Huddle, a podcast that takes a look at all things marketing in the world of sports. Alongside […]

Snapchat Memories: Increased Engagement, Results & Fun

Snapchat Memories just got released in the latest update and I’m doing backflips of excitement as it’s about to take my (and your) Snapchat game to a whole new level. For a while […]

Podcast Movement 16: Best Podcasting Nuggets of Wisdom

I just attended Podcast Movement 2016 in Chicago, a conference for podcasters, by podcasters, and it was great. It was my first time attending and my main purpose for being […]

16: Topps Chris Vaccaro

Chris Vaccaro, Editor-in-Chief and Director of App Production for Topps, joins The Rob Cressy Show to talk about Topps digital strategy and how they think about engaging their sports card loving community. Chris […]

Shoe Dog: The Entrepreneurial Journey of Nike’s Phil Knight

I just finished reading Shoe Dog: A Memoir by the Creator of Nike by Phil Knight and it was great. The book primarily focused on Phil Knight’s journey of building […]

Tai Lopez 67 Steps Review: A Path To Living The Good Life

I just finished Tai Lopez 67 Steps program and it truly was life changing. Knowledge is power and the more you know the better. This post is a review of […]

15: Creative Excellence with Ponch Blesius

Ponch Blesius, Chief Creative Officer at Creative Promotional Products, joins The Rob Cressy Show to talk about creative excellence. In our conversation some of the topics Ponch Blesius and I cover include: […]

14: Turning a Blog Into an Book with Zack Price

Zack Price, creator of Blog Into Book, joins The Rob Cressy Show to talk about how bloggers and publishers can turn their content into an eBook that they can sell. […]

Ultimate Guide: Digital Marketing to Millennials

I’m Rob Cressy, Founder of Cress Media, and I specialize in digital marketing to millennials. I am a millennial and thus I think like a millennial. Know thy target demographic! […]

13: Monetize Your Passion with Jason Zook

Jason Zook joins The Rob Cressy Show to talk about how to monetize your passion, be a disciplined creative, plus shares stories and advice from his spectacularly unique journey. In case you […]

12: EA Sports Social + Madden 17 Cover w/ Kurt Stadelman

Kurt Stadelman, Social Media Manager at EA Sports, joins The Rob Cressy Show to talk about the EA Sports brand engagements at the NFL Draft, their social media strategy and where […]

11: Non-New Agey Mindfulness with Connie McLaughlin

Connie McLaughlin, Behavior and Performance Specialist at Inner Buzz, joins The Rob Cressy Show to talk about mindfulness and meditation in the least new agey way possible. Meditating is something that has […]

Relentless by Tim Grover: Become Unstoppable

I just finished reading Relentless: From Good to Great to Unstoppable by Tim Grover and it was straight fire. In case you aren’t familiar, Tim Grover was the elite trainer for […]

10: Comedy Writing Tips with David Wolinsky

David Wolinsky, comedy writer, creator, and the teacher of my Humor Writing For The Internet classes at Second City, joins The Rob Cressy Show to talk about creating and comedy […]

Snapchat For Business: Grow, Engage, Deliver Results

Hi! I’m Rob Cressy, Founder of Cress Media, and I just finished teaching a Snapchat for Business workshop at 1871 Chicago. As an added value to the people in attendance […]

8: Being Excellent with Brian Cristiano

Brian Cristiano, CEO of Bold Worldwide, joins The Rob Cressy Show to talk about excellence. What are the principals behind why he and his agency are excellent. In our conversation some […]

How I Tried To Land My Dream Job with Bill Simmons

If you saw a posting for your dream job what approach would you take to try and land it? This post is about the approach I took to try and land […]

7: Creating a Fun Workplace Culture w/ Erin Cigich

Erin Cigich, CEO of Clickbooth, joins The Rob Cressy Show to talk about creating a fun workplace culture. Why it’s important, how she’s done it at Clickbooth, and the positive benefits […]

6: Benefits of Visual Learning w/ Marc McLaughlin

Marc McLaughlin, International Partner & Business Designer at Business Models Inc., joins The Rob Cressy show to talk about visual learning and building better business models. In our conversation some of […]

Content Creation Philosophy For Excellent Results

This is my content creation philosophy. The principles I follow for creating engaging content, marketing, and social media that builds an emotional connection, tells a brand story, and gets your audience looking forward […]

5: The Awesome Power of Improv with Kate Duffy

Kate Duffy, my first improv teacher at Second City, joins The Rob Cressy Show to talk about the fun and awesomeness of improv, how it can help you in business, and […]

4: The Art of Relationship Building w/ Todd Heyden

Becoming an ace at building relationships can do so much for your business and overall happiness. One person who can attribute a ton of success to the way he builds relationships […]

3: Content Creation & Digital Marketing Tips with Pete Herrnreiter

Looking for actionable content creation and digital marketing tips? If so you’ll enjoy this episode of The Rob Cressy Show where I chat with Pete Herrnreiter, VP of Digital Strategy at […]

2: Having an NFL Mindset with Brandon Williams

Brandon Williams is a former Wisconsin standout wide receiver, multiple year NFL player turned author, speaker, commentator and entrepreneur. He joins The Rob Cressy Show to talk about the mindset it took […]

1: Comedy Writing at The Onion with Scott Dikkers

Scott Dikkers is one of the Founders of The Onion and was my teacher at Second City for the Writing With The Onion classes. He joins The Rob Cressy show […]

Ep 000: Welcome To The 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 […]

Phone Chicken: a Game of Taking Back Power

Want to add more fun to your life in a trivial manner while taking back power at the same time? The next time you are on a phone call don’t hang up first. […]

Wynwood Walls Graffiti & Street Art

If you are ever in Miami I highly recommend stopping by Wynwood Walls, a graffiti and street art park. I stopped by on my way out of the city and could […]

Top 5 Podcast Influences: March 2, 2016

Entrepreneur and motivational speaker Jim Rohn said, “You are the average of the five people you spend the most time with.” I’m big into listening to podcasts because I always […]

Top 5 Business & Entrepreneur Podcast Influences: Feb 24

Entrepreneur and motivational speaker Jim Rohn said, “You are the average of the five people you spend the most time with.” I’m big into listening to podcasts because I always […]

Gary Vaynerchuk Mission Statement & Continuity Builds Speed

I was listening to Episode 179 of the Ask Gary Vee Show when Gary Vaynerchuk shared the mission statement of his company and it was so good that I had to write […]

Top 5 Podcast Influences: Feb 17

Entrepreneur and motivational speaker Jim Rohn once said, “You are the average of the five people you spend the most time with.” John Lee Dumas from the Entrepreneur on Fire […]

How To Have More Fun & Be Happier

I’m an eternal optimist who is happy 99.9% of the time. I’m able to do so because I know how to have more fun in virtually any situation. I thought I’d […]

Snapchat Tips & Secrets | Make Your Snaps Stand Out

Want to know some Snapchat tips & tricks to make your Snaps stand out more and help grow your audience? Good. I just created a video explaining some fun and creative Snapchat tips […]

Chris Brogan’s Simple Process For Setting & Accomplishing your #1 Goal

I just listened to the Entrepreneur on Fire podcast hosted by John Lee Dumas with author and business advisor Chris Brogan and it was so good and got me so jazzed up that […]

Stand Out: Breakthough Ideas & Build a Following

I just read Stand Out: How to Find Your Breakthrough Idea and Build a Following Around it by Dorie Clark and it was awesome. Since I’m currently building a community of […]

Contagious: Why Things Catch On

Do you want to learn how things go viral or why things catch on? I did, so that’s why I read Contagious: Why Things Catch On by Jonah Berger. It was phenomenal […]

Pitch Anything: A Better Method To Present & Persuade

I just finished reading Pitch Anything: An Innovative Method for Presenting, Persuading, and Winning the Deal by Oren Klaff and it was incredible. The information was so good that I […]

Extreme Ownership: Life Changing Leadership

I just finished reading Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink & Leif Babin and it was one of the best books I’ve ever read. […]

Stan Van Gundy on Having a Growth Mindset

Today I was listening to Zach Lowe’s The Lowe Post podcast with Pistons Coach/GM Stan Van Gundy (which was a must listen for anyone who loves the NBA) and they were […]

Chicago Office Space Wanted to Build Sports Media Office

So I’ve got an interesting request. I’m looking to trade social media/marketing/creative services in exchange for office space in Chicago to built out a small sports media office. Here’s the […]

The Most Important Part Of My Morning Routine

Without a doubt the most important parts of my morning routine, which is something I attribute much of my success in business and in life to, is having a reading routine where […]

How and Why I Wake Up at 5:29 am

Have you ever wondered how to wake up early? For the longest time I did, until I figured out a simple life hack that allowed me to wake up earlier. This […]

Harley-Davidson Cologne: Worst Idea Ever?

Harley-Davidson cologne is something that’s new to my life. I just found out about it 2 minutes ago through a mention in a Create Your Own Position post for Huckberry. I want to […]

21 Comedy Writing Tips

In the third part of my “things learned studying comedy at Second City” series, I continue down the path of wisdom I learned during my introductory Writing For The Onion class. […]

Social Media Wisdom from House of Cards

I’m currently binge watching House of Cards and when I heard this quote it struck a cord with me. One thing that many businesses fail to realize is the power […]

Best Takeaways From 1871 Chat with Kelly Leonard

At 1871 today Howard Tullman hosted a fireside chat with Kelly Leonard, author of Yes, And, a book about how improvisation reverses “No, But” thinking and improves creativity and collaboration […]

Life Hack: Naked Pre-Shower Pushups

I’m always working on creating new life hacks and routines to make my life better and more efficient. Recently I started doing daily naked pushups as I waited for the shower to […]

11 Funny Filters To Write Jokes

In my Writing For The Onion class at Second City my teacher, Scott Dikkers (who is a Co-Founder of The Onion), taught us the 11 Funny Filters to Write Jokes. […]

Hate to Lose vs Love to Win

I hate to lose more than anything. I have interviewed hundreds of sales professionals over the years and I always ask the question of hate to lose vs love to win. […]

If You Don’t Ask, The Answer Is Always No

“If you don’t ask, the answer is always no” is a phrase that has stuck with me ever since I graduated from Miami (OH) University back in 2002. It appeared in […]

Learning at Second City & the Power of Yes And

I’ve spent the last four years learning improv and comedy writing at the Second City Training Center and it’s been an invaluable resource that I highly recommend to anyone. In case […]

Why I Love to Hear NO

Most people shut down and get discouraged after hearing the word no or getting rejected. It’s natural but what if you train your brain to think the opposite and learn […]

Creating Reaction Videos For Sports Bar Marketing

One of the verticals that our content creation and fan engagement services makes a ton of sense with is sports bars. We’ve run a sports blog for the last five years organically […]

Business Hack: Fact About Me Of The Day

Over 8 years ago I created a business hack that has allowed me to easily build rapport while doing sales prospecting and sending out emails. It’s called “Fact About Me […]

Social Media Lessons From 2 Chainz

Do you wanna pull up to the scene with your ceiling missing? Then when it comes to social media and content creation take a page from 2 Chainz. Be Different. […]

Content Rules Everything Around Me – C.R.E.A.M.

Today I’m inspired by the Kings of hip hop, the Wu-Tang Clan. Content is King and it’s everywhere. Take this concept and mash it together with some Method Man flow […]

March Madness Marketing to Sports Fans

March Madness kicks off one of the best sports months of the year and is a great opportunity for brands to engage with their sports fan audience. The beauty of March […]

Growing & Engaging A Baseball Community Via A 2x Day Video Show

Welcome to a case study about how Rob Cressy created a twice a day baseball video show to help grow and engage a community for a baseball app. Goals: To […]


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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.