How To Make It In Sports Media with Jim Weber

By November 3, 2015June 18th, 2018No Comments


I often get hit up asking how to make it in sports media. Many assume that just because you run a sports website and people follow you on social media that everything is puppy dogs and rainbows. In actuality there is tons of grinding and hard work on the back-end, limited resources, working for free, and doing anything you can to keep pushing your brand/sports website forward every day.

I had the pleasure of talking with Jim Weber, the Founder of, about how he built Lost Lettermen into one of the best college sports sites. Lost Lettermen has been around for over 6 years so what does he attribute their longevity, growth, and success to? What tips does he have for sports fans hoping to make it in sports media one day or run their own site?

Since Jim is a big college football fan at the end of the interview we also dish about college football. What does he think about Baylor without Seth Russell at quarterback and can Clemson win the National Title?

I just read a great article from Clay Travis at Outkick the Coverage about Grantland shutting down and the lay of the land in sports media. It’s lengthy but if you want to know how to make it in sports media from someone who risked it all, built his brand one day at a time through tireless hard work, and is now successful then it’s a great read.

For those of you who hope to make it the sports comedy space one day then I recommend you checking out this post from Bryan Tucker, co-head writer at Saturday Night Live and Founder of sports comedy site The Kicker, about how to make it on Saturday Night Live. I’ve spent the last four years studying improv and comedy writing at Second City so much of what Bryan recommends resonates very much with the journey I’ve been on.




1. World’s Largest NBA Jerseys Database: There’s over 763 past and present NBA players from 1985 whose jerseys you can buy. If you love basketball jerseys then this is the holy grail!

2. Dream of Working in Sports? We are looking for talented, passionate sports fans that want to be part of Team Bacon Sports and help grow the brand. Having the sports job of your dreams is possible and we want to help make that happen!

3. 11 Funny Filters to Write Jokes : Write better comedy by learning the fundamentals of joke writing from the Second City Training Center in Chicago.

Rob Cressy

Rob Cressy

Sports loving free throw specialist and yinzer living in Chicago who is awesome most of the time, has run with the bulls in Spain, and is a graduate of Second City's Improv program.