ImagiNation with Rob Cressy


Rob Cressy

Occupation: Founder, Bacon Sports and Cress Media

Age: 37

Favorite Productivity Tool: Evernote (I've written down every conversation and idea I've had for the last 5+ years) 

Most Recommended App: Slack 

Last Book You Read: "Tribe of Mentors" by Tim Ferriss


Twitter: @RobCressy // Instagram: @Rob_Cressy

Twitter: @BaconSports // Instagram: @BaconSports

Tell us about your journey? I'm a creator, entrepreneur, and doer who is awesome most of the time and always watching sports. I was successful at digital advertising sales for 7 years, but even though I made good money I got to the point where I wasn't looking forward to slinging banner ads and text links everyday. I always dreamed of being a creator and working in sports. Finally, I saved up enough money, quit my job, and started with the goal of turning a sports comedy blog into the awesomest sports media company ever. I've been doing that full time for the last 5+ years. Along the way, I decided to study improv and comedy writing at Second City. My goal was not to become a comedian but instead to learn the skills of one so that I could apply it to the content and marketing I create. For the first 3+ years of Bacon Sports, as editor in chief, I was managing a team of writers and we published over 1,500 articles, 100 videos, and 150 podcast episodes while we continued to grow our community. The publishing landscape was shifting and it became harder for sites to monetize. Because of this I decided to take the content creation and fan engagement skills that I had learned, combined with my Marketing degree, and open up Cress Media, a content studio specializing in audio, video, and social content creation for brand, publishers, and agencies targeting sports fans. This allowed us to not have to rely on advertising revenue from Bacon Sports, and still work on awesome projects that we loved. I continue to grow both Cress Media and Bacon Sports on a daily basis.      

What's your favorite part of your day? My favorite part of the day happens first thing in the morning. I wake up at 5:23 am, brush my teeth, and then go make a cup of coffee. I then read a book until I finish the cup of coffee (which is typically between 30-40 minutes.) By doing this it is my way of ensuring that no matter what else happens the rest of the day that I am better today than I was yesterday (since I learned something by reading.) It also primes me for success the rest of the day and gets me in the right frame of mind.

When do you feel most successful? After doing something that I don't want to do. For example, one morning I was feeling less than 100% and I really didn't want to go the gym. The easy thing for me to do would be to push it off a day because I had a built in excuse. It was at that moment that I powered through, put my gym clothes on, and ran to the gym. I am constantly working on getting comfortable being uncomfortable and that was one of those moments. It's something I learned from reading Jocko Willink's book "Extreme Ownership."

What do you do to recharge when you’re feeling drained? This is something that I struggle with and am constantly working on. There was a book I read called "The Artists Way" by Julia Cameron and in it she talks about going on "Artist Dates" where you block of a period of time every week  to go do something creative. This can be whatever you want. For me my "Artist Date" is going to the movies by myself. I'll often do it during the middle of the day, which is the complete opposite time in which you'd expect. I treat it like I would scheduling a call or working on a project. What I like about going to the movies is that it is the pinnacle of storytelling and that inspires me. It is also refreshing to get away from phones, computers, email, and social media. 

What do you know today that you wish you would have known when you first got started as an entrepreneur? To be careful with who you partner with. I'm a naturally trusting person and when combined with inexperience and optimism that can become dangerous when things don't go as planned.  

How do you optimize your day? I've turned myself into a productivity robot and try to be very accountable to my time. I write down my life goals twice a day (morning and night), write down the targets that I want to accomplish that day, and then I start crossing things off. One big mindset shift happened to me when I found out that you get 86,400 seconds in a day. It got me thinking about how I use them on a micro level. The other big thing was a quote, "Non-renewable time." You can never get time back. Because of that it helps me with accountability and optimizing my day. 

Who is the person/people who allowed you to imagine more? Myself. The biggest gift I wish I could give others is self-awareness. Once you have it you see the world entirely different. It's why I can get up so early every morning. It's because I want to be happy doing what I love and I'm willing to do whatever it takes in order to make that happen. The fire in me never burns out. As for others who have allowed me to imagine more, the list is incredible long and primarily comes from people who's books I've read and podcasts I've listened to. Some of them include Grant Cardone, Tim Ferriss, Bill Simmons, Dan Patrick, Richard Branson

What does imagining more mean to you and your story? It means everything. I've designed my life to include things that I love doing. All along the way I want to have a positive impact on others by showing that imagining and doing more is possible. My mission is to help others achieve their dreams through a love of sports. I always figured that if I could find a way to make it happen then I could show others how it was done. In turn I would then have a company where everyday people coming in to work and they are living their dreams. 

If you could do more of one thing every day what would it be? Create. All day every day. This would include multiple hours of podcasting, creating videos, writing blog posts. This is already part of my life in some capacity, but as the Founder of a company I wear many hats which often takes away from the thing I love most. 

Favorite social media platform? Instagram.