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Outdoor Adventure Awaits

Madison native and fourth generation entrepreneur Brooks Maddox Pennington IV dreamed of a better way to explore the outdoors. After years of traveling as an avid hunter and fisherman, he saw a need for an easier way to go on guided outdoor adventures. Through his passion for outdoor adventure and his family’s history of entrepreneurship, Brooks decided to turn his dream into a reality and created Outguided.

I had been trying to book an elk hunt,” Brooks said. “I’ve always wanted to go elk

hunting. I love to bow hunt, and I wanted to bow hunt for elk. I thought it would be the greatest adventure, so I spent hours and hours researching. The amount of time it took for me to find three or four options was ridiculous. After all that, I said there has to be a better way. There needs to be a platform, so that’s what I set out to create.”

Outguided is an online platform where people can book guided outdoor adventures. When someone visits Outguided, they are able to explore a wide variety of outdoor adventures. They can search by adventure or location. Once they’ve found the adventure they want, they can book it, pay for it and message with the guide. Everything goes through the Outguided platform that Brooks and his friend, Co-founder and CEO of Outguided, Tim Rood, custom built from the ground up.

“If you want to go heli-skiing, we have over half of the global heli-skiing trips in here,” Brooks said. “You can search heli-skiing and see what all the different adventures are.”

Brooks graduated from the University of Georgia with a bachelor’s in Business Administration in Finance from Terry College of Business, and then went to Mercer University for his Master of Business Administration (MBA).

“I grew up in a decently well-known family in this area,” Brooks said. “My great-grandfather, Brooks Pennington Sr., started Pennington Seed, and my grandfather, father and uncles all helped to grow it into one of the largest seed companies in the world. I have tremendous respect for everything that they’ve done with the seed company. I always got to witness firsthand the hard work that they put into it and what it takes to grow a company of that scale. I’ve always wanted to try to do it over again, so I guess that always gave me the drive to go in and create these other ventures.”

Brooks has always been an entrepreneur. He remembers picking up pecans from his family’s property and selling them when he was 11 years old. Eventually he figured out that he could get his friends to help him pick up pecans, and he was able to sell more of them.

When Brooks was 17 years old, he started his first company, B&E Pine Straw. Within a few months it became one of the larger distributors in northern Georgia. They sold and also spread straw predominately in Morgan and Greene counties, specifically in and around Madison as well as the Reynolds area at Lake Oconee.

Brooks and Cecily after a high school football game.

Brooks is happily married to his high school sweetheart, Cecily Pennington. They got married in 2014. He loves spending time with Cecily and their children.

“We crossed paths when growing up in Madison, so we both knew of each other,” Brooks said. “I ‘messaged’ her on AOL Instant Messenger (AIM), and she agreed to go on a date with me. We have pretty much been together since then. She was 15 years old, and I was 16 years old. … She is my rock and the reason I’m able to continue chasing my entrepreneurial endeavors. She is awesome.”

Brooks and Cecily are passionate about their small group at the Madison First United Methodist Church, and he has led several Wednesday night Bible studies. He has volunteered at the Madison Fire Department since he was 18 years old, and took over as the Fire Chief in 2020.

“Being able to lead a department like ours, one that is made up of such incredible, selfless individuals, is a great honor and responsibility,” Brooks said. “It is not something that I take lightly and it requires significant commitment, but I am grateful to have the opportunity to serve my community in such a unique and awesome way. While being able to help people when they need it most is definitely a reason to continue to do it. … Madison is a great place to grow up and live. From the fire department, to bible study families, to just new friends, it seems like there is a constant community.”

In 2016, he started an entity management company, Pennington & Pennington, LLC, and his father, Brooks “Sonny” Pennington III, joined him as partner. This allowed Brooks the opportunity to see and understand different types of businesses, and it inspired him to create one he is passionate about and can use to introduce other people to new passions, such as outdoor adventure.

Brooks III “Sonny” hunting with his son Brooks IV.

When Brooks was in college at UGA, he studied abroad in Cape Town, South Africa and was paired to room with Tim Rood. Tim lived all over the world in his youth. He lived in Australia, England and went to high school in Texas, and he later graduated from UGA with a Bachelor of Economics. After graduating, Tim moved to San Francisco to work in investment banking for BTS.

“That was 2014, and it was a very interesting time to be there,” Tim said. “A lot of tech companies were popping up, Uber was new, Airbnb was new. I decided to make the leap and jump into tech.”

Tim worked at various tech companies building platforms in San Francisco, Kenya and Los Angeles. Brooks called him in 2019 to pitch his new business idea. Tim flew to Georgia the next weekend.

“We sat at my house and went through the opportunity and industry,” Brooks said. “With [Tim’s] background in tech, he realized that it was a very highly fragmented industry, and [the idea] was absolutely right for a marketplace type of product. From his tech side, he was all in, so he quit his job and went all in on Outguided.”

Tim gets the experience of camping on a beach.

Tim wasn’t an avid hunter or fisher, so before they got started, he rented a van in Charleston, South Carolina. He lived in the van and traveled to Miami, Florida, stopping at all the marinas to meet with the guides.

“It was incredible,” Tim said. “That was the beginning of really starting to build our product.”

Tim talked to fishing guides in different areas to find out what they do, what they're passionate about and what their needs are. He did this to truly understand exactly what he and Brooks needed to build.

“From the very beginning we had the idea that the only way this could truly work is to be the platform that guides want to use,” Brooks said. “The guides want to guide. They want to take people fishing or whatever the adventure is. They don’t want to have to sit in the office and handle the books, the bookings and the calendar, the whole nine yards. … Not only can we be the marketplace, but we can be the software that powers adventure.”

Outguided donates 2% of its profits to support organizations that work to preserve the world’s wild spaces. They decided to donate a percentage of its profit to conservation because Brooks and Tim knew that outdoor adventure opportunities would cease to exist without people caring and contributing to the cause.

Introductory trips are an integral part of the platform. “Say you’ve never been hunting before, and you wanted to go turkey hunting,” Brooks said. “Where would you start? You would have no idea where to start. Well, that is a tremendous problem for the industry – getting new people introduced the right way, through the right guides and the right teachers. Because at the end of the day, the true conservationist, the people that are going to continue to look after and be stewards of wildlife are the people that are passionate about it. It’s the people that are spending money on licenses that are providing the capital to be able to continue to protect them. The only way to ensure that conservation side of it is to continue to introduce people [to the outdoors], but you have to do it the right way. It’s not about the trophy. It’s about the pursuit. It’s about the reverence for the animal and the adventure behind whatever guided trip you’re going on.”

Whether you want to go elk hunting in Utah, fly-fishing in the Seychelles of Africa or mountain biking in Patagonia, your adventure is only one click away. To book your next guided outdoor adventure, visit

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Story written by Katie Marie O'Neal, photos contributed, published in Lakelife magazine May-June 2022.


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