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David Littlefield is the Founder and Chairman of Littlefield Agency, which he started in 1980. For over 41 years, the agency has served B2B and restaurant businesses. They even have an official holiday in June every year declared by the Mayor of Tulsa. Littlefield Agency clientele includes companies like the Tulsa Airport, Francis Energy, Tulsa Health Department, Rib Crib, and more. David started the agency with hopes that it would continually evolve, launching the addition of planning and insights, the transition from traditional to digital, and many more initiatives.

Sam Littlefield is the President and CEO of Littlefield Agency. After receiving his undergraduate degree from the University of San Diego, Sam was hired as an Account Manager for Mirum, one of the world’s largest digital advertising agencies. Since transitioning to Littlefield Agency in 2016, Sam has provided invaluable insight to the company by using his passion for the digital world to drive business.

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Here’s a glimpse of what you’ll learn:

  • How David Littlefield started the Littlefield Agency in 1980
  • Sam Littlefield shares how they got into the analytics business
  • Lessons about agency business Sam learned from his dad
  • How to smoothly transition your business to a family member
  • Mistakes to avoid when transitioning your business to the next generation
  • Why did Sam quit his job over in San Diego and return to Tulsa to work with his dad?
  • Dealing with different leadership styles
  • How Littlefield Agency helped Ditch Witch come into the digital age
  • Sam and David share what they are doing with Incredible Pizza and Grasshopper

In this episode…

It’s always a great look — and an innate wish — for every entrepreneur to transition their business to the next generation. Unfortunately, not many companies have successfully transitioned their companies into family-led businesses.

If you’ve been thinking about bringing on a spouse, daughter, son, or any other family member to lead your business, this episode is for you. David and Sam Littlefield share their experience of how they transitioned smoothly and grew their family business to the next level. Want to learn more?

Listen to this episode of the Inspired Insider Podcast with Dr. Jeremy Weisz to hear from David Littlefield and Sam Littlefield of Littlefield Agency about transitioning your business to the next generation. They open up about why they think their professional relationship has worked well so far, what they did to set the tone, and how they’re working together to grow their clients’ businesses. You don’t want to miss a minute of this episode.

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Episode Transcript

Jeremy Weisz 0:20

Jeremy Weisz here, Founder of, I talk with inspirational entrepreneurs and leaders. And I’m here with David and Sam Littlefield. I’m gonna introduce them formally in a second. But David and Sam, I always like to mention other episodes people should check out. Since they, you know, they have a lot they’ve been doing this for, I’m gonna say, over 41 years, their company has been in existence, but they have b2b, they have food, they have financial services, but I thought I think of some in the food space, guys. So I had Noah Alper who started Noah’s Bagels, he started one store in 1989, and built it to a chain of 38 stores. He sold the Einstein Bagels for over $100 million in 1995. But what I love about the stories and the stories out in spurred insider is not just about the success, because all we both know that there’s a lot of peaks and valleys to this. And he talked about how he was selling religious tchotchkes out of the back of his trunk to make ends meet. And it wasn’t always, you know, just as 100 million dollar sale, he started a lot of businesses and there were some ups and downs along the way. So check out that interview with Noah Alper, it’s really, really good. And there’s many more on even the founder of Big League Chew. I loved having him on talking about sitting in the bullpen as a minor league pitcher, and coming up with the idea for Big League Chew. And so that was an amazing story. And I just love the product too. So that and many more. This episode is brought to you by Rise25 at Rise25 we help businesses give to and connect to their dream 100 relationships and partnerships. And we do that by helping you run your podcast. And for me, the number one thing in my life is relationships. I’m always looking at ways to give to my best relationships and have the people the companies that I admire profiling them on my podcast so that everyone could get to know them better. So if you have thought about starting or launching a podcast, you can go to and email us for any questions. We’ve been doing it for over a decade now. Before people even knew what a podcast was. And so check it out. And this is brought to you by you know the SpotOn Series with top leaders in the restaurant and food Matt Hyman started SpotOn. And they have a flagship solution spot on restaurant where they have a software and payments solution for restaurants and they’ve served Dairy Queen, Quiznos Subway many more. This is appropriate for this episode, because the Littlefield Agency helps a lot of restaurants actually, so is founded in 1980. Believe it or not Littlefield Agency in over 41 years has served B2B and food and financial and they even have an official holiday every year to Declared by the Mayor of Tulsa in June, do like they’ve been around. I mean, they’ve specialized in b2b and restaurant. And the you know, they’ve even served the Tulsa Airport, Francis Energy, Tulsa Health Department, Rib Crib, and so many more. I just want to thank Sam and David Littlefield for joining me.

Sam Littlefield 3:28

Hey, happy to be here.

David Littlefield 3:29

Good to be with you.

Jeremy Weisz 3:30

You know, I know. David, we had a conversation before about how this agency started out and in the services, right, and you talked about the radio, the TV, the billboard direct mail, which First of all, I geek out on direct mail and all that stuff now. And that stuff’s not even dead. But, and we’re gonna get into that, I think this is gonna be fascinating, Sam, because the transition of leadership and the shift in leadership and everything like that we’re gonna get into but David start us off over 40 years ago. What did the agency look like? What were some of the services and clients,

David Littlefield 4:08

I started my agency in 1980, after working for two different other agencies. And both of them were Keep in mind this is 1980s was a long time ago. Both of them were 100%, creatively focused, and they were run by creative directors, the owners of the companies were the creative directors. And I remember the first company as a young account manager. We were more afraid to go back until the creative director owner that we didn’t sell his concept. Then we were to argue with the client that this is what they ought to do. It was it was nuts. And so long story short, when I started my company, my background before I got in the agency business was in sales and marketing. And I thought you know, people, the creative is important because that’s means to the end. But that’s not why people hire an agency, they want to sell more product or result or sell more services. And so we were putting the creative cart before the marketing horse, if you will. And so I started my agency with a focus on let’s do have this be research based marketing based, more of a strategic level. And so I started this as a one man band using creative resources on a freelance basis for probably two and a half years till I grew to a point where I could start adding the staff. And the first person that I hired after an administrative assistant was a very, very good creative director that believed in the way I wanted to do this. And so we built our company based upon on marketing strategy and research, but really good creative to deliver the messaging, once we know what’s the most relevant message between that’s going to resonate with that, that customer for that brand.