Reinvention, Strategy, and the Thrill of the Chase

My name is Dr. Sam McGough, and this is The Hunt for Success. This week we’ve got Gregory DePriest — an Amazon delivery service professional who’s done a few other businesses, and who loves to hunt and fish. We’re going to talk about both. Welcome to the show, Gregory.

Thank you so much. It’s a pleasure being here.

Take us back — how did you get started, and what’s the journey been?

I’m one of ten kids. My mother was widowed at 40 — an incredibly strong woman with ten kids at home. I was 13 when my father passed, and Mother got us boys around strong men. The church we went to had over 3,000 acres leased to hunt on, a hunting club in Mississippi, and those men — a lot of them successful business people — taught me and my brothers how to hunt and how to be men. I got out of high school, went to college, and started in banking. That was my first career: Nissan Motor Acceptance, and I helped start Infiniti Finance when the Infiniti cars came along. Then in 1992 I took a totally different path and became a pastor — a small church of 60 people in East Tennessee. I set a goal for 25 years, and in my 24th year we became the largest-attended church in the Tri-Cities: over 2,200 people a Sunday.

And you stepped away from that.

I told the board in my 24th year, “I’m stepping down — you’ve got one year to find my replacement.” I wanted to go into logistics. I didn’t have a retirement fund. I never made a lot of money as a pastor — large church, very blessed, I just didn’t believe that’s where you’re supposed to make it. Around 2018 a friend of mine, a billionaire, asked me to help raise $30 million for an orphanage. We raised $56.6 million. I brought in Jack Nicklaus, Gary Player, Peyton Manning, Dan Marino — people paid $100,000 apiece to play golf with them. It’s the highest PGA-endorsed fundraiser in history. Right after that, Amazon talked to me, and the rest is history. I started a logistics company with Amazon in 2019, and it’s been fabulous.

I met you at a conference, and you’re running more routes per day than almost anyone I talk to — sometimes double. How?

It’s not one thing. A good station, a great team — you can’t get this large without one. I’ve got over 200 employees; my payroll’s over $600,000 a month. When all of it comes together, it’s great. And it starts with this: life is a continued path of growth, and if you’re not on it, you get left behind. I’m 67, I’ll be 68 this year, and I’ve still got big dreams. I put myself around people who are better than I am.

So how do you let go of one phase to move to the next? A lot of people hang on too long.

Everything in life has a shelf life. You can extend it for a while, but not forever — so you’ve got to constantly reinvent yourself for the next phase, or life leaves you. A lot of people die at 25 but aren’t buried until 75. I never want to be that way. And here’s the other piece: faith without a strategy is just a wish. I pastored 25 years and watched people use faith as an excuse for inaction. If somebody tells me they need to pray about it, what they just told me is no. You can’t steer a car while it’s sitting still — put it in drive and you can correct even a wrong direction. Most people have no strategy for their life.

What was yours, walking out of the church?

The staff asked what I was going to do. I said, “Own a logistics company.” How? “I’ll get my CDL, get a truck, start driving it, and in five years I’ll own a bunch of them.” It’s gone much better than that — but I had a strategy. In the area I was well known, and I didn’t have too much pride. A lot of people have pride that keeps them from their future. I was willing to get in an 18-wheeler and drive it. That was at 57 years of age.

So how did the company actually start?

Amazon called and asked if I’d go to Greensboro, North Carolina to run their delivery. I thought about it ten seconds and said, “I never woke up wanting to live in Greensboro — what else have you got?” They said Austin, Texas. I said, “Done deal.” They asked if I needed to talk to my wife — she does wealth management for Merrill Lynch, she was our primary income — and I said, “I’ll tell her when she gets home that I’m moving to Austin.” Funny thing: at 19 I went to Austin to buy bulls for the farm in Mississippi and told my brothers, “I’m going to live here one day.” Forty years later, I did.

And then you gave it up.

When Amazon came to the Tri-Cities, I called and said I wanted to transfer back. They said they couldn’t do it. I said, “You’re the biggest tech company in the world — why not?” “We just can’t.” So I said, “Okay, I’ll start over.” They couldn’t believe I’d give up what I had. I told them, “I didn’t know what I was doing the first time and I was successful. I know what I’m doing now — I know I’ll be successful.” And I did.

That’s huge confidence. What gave you the faith to just pick up and rebuild?

You have no idea how many nights I lay awake thinking I’d be a total failure. Amazon is a brutal taskmaster — I love it, but it’s tough. I’d lie there wondering, “God, I was a success before. Am I going to be a failure now?” But I love reading biographies, and here’s what I learned: people who didn’t make big moves never lived big lives.

I look around and see a lot of talented people who never take the leap.

At my 50th class reunion — and I was near the bottom of that class, never “most likely to succeed” — I’d say I’m the top income earner of the whole class, probably by a lot. People ask if I ever thought I’d be where I am. I say no — I thought I’d be further. People don’t dream big enough. I asked my kids: if you knew it was impossible to fail, what would you do? My son said he wouldn’t be afraid to try anything. Right — you can get experience, even painful experience, but you can’t fail. Get that word out of your vocabulary. Most people are more focused on the failure than the reward.

They fear the embarrassment of failing more than they want the win.

Yes. Highly successful people disassociate themselves from other people’s opinions — look at Elon Musk. You can’t live your life based on how other people view you. People think about you very briefly — but that’s exactly why it matters, because that’s all the time you get to make an impression. You’re always selling yourself: how you dress, how you present yourself. When you walk out of your house in the morning, you’re selling yourself.

When it comes to your team, how do you get them motivated and ready to do the job?

You pay peanuts, you get monkeys — so I pay right, but I pay on performance. I sit them down and say, “Your performance drives what you make. Don’t perform, you won’t get it. Perform, and you’ll be rewarded, nicely.” And I start every meeting with this: I want the best life for you that you can possibly have. I’ll be your advocate — I want you to have a home, your bills paid, a car, to be happy. If you ever get a better opportunity, I’ll help you. All I ask is that you want that more than I want it for you.

That weeds the wrong people out fast.

There’s one curse word I hate: potential. My team knows it. Potential means you want it for someone more than they want it for themselves. If someone tells me, “This person has so much potential,” I say don’t even use that word around me — if they wanted it badly enough, they’d already be doing it. And here’s the other thing: when a person has drama, they need to be on salary, because they’ll constantly be sabotaging. Get the drama out of your life — that’s order and structure. Put order and structure in your life and there’s no reason you can’t be successful.

So you can vet for that in hiring.

I’ve got a friend who, when he interviews someone, has a guy go look inside their car to see how clean it is — because if they won’t take care of what they have, they won’t take care of what he has. If there are more french fries between the seats than in the McDonald’s bag, they’re not getting hired. I’m a fanatic about it at home — closet doors closed, drawers closed. My wife asked why, and I said, “Completion.” A drawer isn’t complete if it’s not closed. A task isn’t done if the shower door’s still open. When you take care of the details, you never have the big issues. Let the details go, and you’ll have a lot of them.

Shifting gears — those men took you hunting as a kid. What lessons from the woods have carried into business?

It’s about strategy. You don’t walk into the woods banging pots and pans. It’s like fly fishing — you’re imitating what’s natural, blending in. I love bird hunting because I love watching the dogs do what they’re trained to do. They know that collar means they get to hunt. And there’s the thrill of the chase — you don’t get up at four in the morning if there’s no thrill in it. It’s the same in business. I’ve got a friend with 17 car dealerships, and his wife asked why he wants more. He said, “It’s not about that — it’s the chase. I love buying something that’s not doing well and turning it around.”

Tell me about the service at these places.

I kept asking where the best experience was, and it kept coming back to one place: Rio Piedra, down in South Georgia. I took my buddy with the dealerships. We pulled up and the host was standing out front, shaking our hands, hors d’oeuvres ready. I told him, “The structure and order — I can totally relax. The way they met me, I know it’s going to be a great hunt.” He looked at it through his salespeople; I looked at it through my drivers delivering smiles. What are they doing that’s so successful that I can copy? I met with all my employees yesterday, did the standup at every load-out, high-fived the drivers — a couple of them just bought new homes, and I’m proud of them.

We were at the Ritz-Carlton in Dallas and my wife asked about a crème brûlée that wasn’t on the menu. Ten minutes later the guy came back with one — he’d gone down the street to get it.

That’s service. At Rio Piedra they brought the cigars out on a silver tray. We sat around the fire pit and had a great conversation with great people. That’s how you relax. I told my wife I want to take her down there — “so you can learn how you ought to treat me all the time.” Went over really well.

We connected over the same things — hunting, fishing, business, cigars, bourbon. What else is there?

Here’s what I’ve discovered: very few men have someone safe to brag to. Someone who’ll celebrate your wins with you and not look at it like you’re trying to outdo them. Hunters celebrate each other. Fishermen celebrate each other. A lot of businesses don’t. And very few men have that.

It’s important to find your tribe — people you can celebrate with. That’s what we’re building with this podcast.

When I was pastoring, my wife looked at me one day and said, “I wish you’d come down off the cross sometime and let Jesus get back up on it.” That was not a compliment — I knew my marriage was in trouble. So I got counseling. The counselor asked, “Who do you trust to talk to?” My brothers and I are close, great family — and I said, “No one.” She went through a whole list. No, no, no. About five weeks in I realized why: I’d be there for anyone, listen, not judge, celebrate with them — and I didn’t trust they’d do the same for me. That was the beginning of a drastic change: I’m going to be around people I can be transparent with, who are safe.

What do you look for in new people?

If a man’s not a good daddy, he’s not going to be my friend. I’ve got friends who may not be the best husbands — I might be in that category — but a man who’s not a good daddy, I don’t want as a friend. I want to hear: is he affirming his kids? Is he an affirmer, or someone who has to be affirmed? If someone has to be affirmed, they’re never safe. You want people who are affirmers to others — “I believe in you, I’ve got your back.” If they’re affirming their children, they’re probably a safe person to be with.

Before we go — favorite places to hunt and fish?

For quail, Prairie Wildlife in Mississippi — Mr. Jimmy Bryan makes sure the hunt is memorable. For pheasant, Firesteel Creek Lodge in Isabel, South Dakota — absolute first class. For fishing, I live in East Tennessee with the Watauga and South Holston right here — outside the Rockies, some of the best fly fishing in the country. On trips I like the Gunnison in Colorado, the Clark and the Yellowstone in Montana, and Rock Creek near Bozeman for wading. My bucket list is a cast-and-blast in Argentina.

We’ll have to connect on some of these. Greg, I’m honored we had you on today.

Thank you so much. It’s my honor. You have a great day.

Guys, again — Hunt for Success. You’ll learn a lot about strategy and business, and a lot about hunting, fishing, and life. Thanks for tuning in. Until next time, this is Sam McGough signing off.