Welcome to another exciting episode of “Conversations with Big Rich.” This week, Big Rich Klein sits down with Jim Winn, a dynamic entrepreneur with a multifaceted career, whose journey has spanned from professional photography to corporate business, and now, to owning and operating multiple businesses within the off-road industry.
Highlights from the Episode:
- Early Life and Career: Jim shares his story of growing up in a baseball-centric family, which instilled in him a competitive spirit and a drive for excellence. His early ambitions took him from a promising photography career, where he captured significant moments like Hurricane Katrina, to becoming an entrepreneur.
- Entrepreneurial Journey: Jim discusses his transition from photography to business, including a stint as a cross-country truck driver, which helped fund his ventures. He eventually founded a small business selling home and garden products, which laid the groundwork for his current ventures.
- Behemoth Drivetrain: Jim talks about acquiring and revitalizing Behemoth Drivetrain, focusing on designing and manufacturing high-performance transfer cases and underdrives for off-road vehicles. He emphasizes the importance of quality and innovation in meeting the needs of enthusiasts and OEMs alike.
- Family and Future Plans: Jim reflects on the importance of family, his children’s involvement in sports, and his commitment to building a legacy in the off-road industry. He shares his vision for continued growth and community impact in Litchfield, Kentucky.
TRANSCRIPT
[00:01:12.480] – Big Rich Klein
My guest on this week’s episode is Jim Winn, who at just 43 years old, is in my book, a classic overachiever. From a childhood filled with high-level baseball to a career in photography, then to corporate business, and now to private business with a focus on off-road. Jim Wyn is driven to Excel. Well, hello, Jim Wyn. So good to have you on the podcast. I’m looking forward to learning all about you.
[00:01:41.220] – Jim Winn
Likewise. I’m excited to be here, Rich. It’s a pleasure to have a chance to chat. We’ve been in your orbit for a long time, so it’s really nice to be able to connect and get to talk at length here.
[00:01:53.680] – Big Rich Klein
Yeah. So let’s talk about first you, and then we’ll get into business. Where were you born and raised?
[00:02:04.000] – Jim Winn
I was originally born in South Mississippi, and was there until I was about 10. And then my family moved to Central Kentucky, and more or less grew up in Bowen Green, central Kentucky, until I graduated college and went on from there. We moved because of my dad’s job. My dad spent his entire professional life around baseball. He was Played in high school, played in college, became a college baseball coach after graduation, and then started working for the Chicago Cubs as a baseball scout, and then was a scout for a number of different Major League teams until he retired a few years ago. So his job took him to Central Kentucky. We followed him up there and spent a big chunk of our younger life on the road, traveling with him, growing up in Major League, Minor League, baseball field across country.
[00:03:00.980] – Big Rich Klein
So at what age did you go from Mississippi to Kentucky?
[00:03:05.180] – Jim Winn
I was about 10, I think, when he moved up there.
[00:03:08.760] – Big Rich Klein
And I have to ask then, did you play baseball as a kid?
[00:03:13.300] – Jim Winn
I did. So I’ve got two younger brothers and a younger sister. We all played sports. I was decent but not great at baseball. Loved it, but was really into other stuff, other sports. I played through high school and then got really busy with other hobbies in college and all that. My two younger brothers are the actual athletes of the family. Dennis and Kevin played through college and then both went on to play Major League Baseball as well and had a career there.

