Ep453: Bet on Yourself: Designing Outdoor Spaces That Tell Your Story with Steve Griggs



 

Not all landscape designers are created equal, and Steve Griggs is living proof.

For nearly four decades, the New York–based designer has been quietly transforming backyards, rooftops, and estates into living works of art. His projects have earned him two spots on the Inc. 5000 list, appearances on Bravo’s Backyard Envy, Good Morning LaLa Land, and features in Forbes, Huffington Post, and The Wall Street Journal. But ask him what he actually does, and he won’t talk about fame or aesthetics first.

He’ll tell you about the guys chiseling stone in the cold.

“Most people just see a pretty picture on Pinterest and say, ‘I want that in my backyard,’” Griggs says. “They have no idea what it takes—the engineering, the plant science, the labor. The real heroes are the guys on the ground doing the work.”

That mix of candor and craftsmanship is exactly what’s made Griggs the guy to call when you want more than a pretty garden.

From “Just a Landscaper” to the Guy Everyone Calls

Griggs didn’t set out to be another name in the landscaping directory. From the beginning, he knew if he stayed generic, he’d be trapped in the race to the bottom.

“Starting out as a landscaper, you don’t want to be a landscaper,” he says bluntly. “You want to become the guy, the gal—the it person. If you don’t separate yourself from the crowd, you’re just competing on price. And that’s a quick land to nowhere.”

To climb out of that commodity trap, he began positioning himself differently. He leaned into media, became a go-to guest on podcasts, and compressed 30 years of work into a visual coffee-table book called Straight Dirt: New York City’s Premier Designer Tells It Like It Is. The book, filled with high-impact photography and honest stories from job sites, became a powerful leave-behind for clients—and a quiet weapon against his competition.

“If a client’s looking at two landscapers with similar pricing, and one of them has a book on the table, they’re probably going with the guy who has the book,” he says. “It raises your credibility the second you walk in.”

Your Backyard, Reimagined as a Story

Ask Griggs what he really does, and he won’t talk about lawns or shrubs. He talks about lifestyle, feeling, and memory.

“Some people paint, some people write music, some people sculpt,” he says. “My art form is your backyard.”

His process starts with listening—not just to what people want built, but how they want to feel when they step outside. Some clients want Vegas energy: pools, lights, late-night entertainment. Others want a zen courtyard to decompress from the city. His job is to translate those emotional cues into a design and then bring it to life in three dimensions.

He’s particularly passionate about the value of outdoor space in dense markets like the Northeast, where property and taxes come at a premium.

“I’ve had clients say, ‘I don’t want to fix up my backyard—we never go outside,’” he laughs. “And I tell them, ‘You never go outside because it looks like this.’”

Since COVID, he’s seen a massive shift in how people relate to outdoor living. Fire pits, outdoor kitchens, TVs, and covered lounges have turned backyards into the new family room.

“The backyard is the new kitchen,” he says. “It’s where memories are made. Your goal is to make your place the coolest house on the block so your kids and their friends want to be there. That’s where the magic happens.”

Money, Mindset, and the Price of Being “The Guy”

Behind the polished projects, Griggs carries a familiar story about money—one that many high-achieving entrepreneurs will recognize.

He grew up in an old-school, working-class household where the soundtrack was scarcity: turn off the lights, we can’t afford that. That narrative turned into an internal script that followed him into adulthood.

“For years I was deathly afraid to talk about money,” he admits. “I’d be terrified to give the real price. In my head it was always, ‘What are they going to think if I say this number?’ I didn’t feel worthy to charge it.”

The turning point came when he realized his clients could write a $100,000 check with the same emotional charge as a phone bill. It wasn’t that the projects weren’t worth the money—it was that he hadn’t fully owned the value of his work.

“You can’t be clipping coupons on groceries and then expect people to hand you six-figure checks,” he says. “It’s a mindset thing. You have to believe you’re the person they want, or you’ll always be just another guy with a truck.”

Today, he’s unapologetic about charging what his projects are worth. He also insists that loving your work isn’t enough—you have to treat it like a real business.

“I used to say, ‘If I love what I do, the money will follow.’ That’s not how it works,” he says. “You’re supposed to make a profit. Business is for profit. Be fair. Don’t take advantage of people. But don’t apologize for making money.”

40 Years In: Jealousy, Grit, and Showing Up Anyway

After four decades in the industry, Griggs has seen trends, companies, and entire economies come and go. Instagram, though, brought a new kind of challenge: comparison.

“Do I get jealous when I see guys online talking about making a million dollars a month? Absolutely,” he says. “Here I am, 40 years of blood, sweat, and tears. It gets to you sometimes.”

His way through it isn’t glamorous. It’s not a hack. It’s consistency.

“The longevity is just consistency,” he says. “Showing up every day. Doing what you say you’re going to do when you say you’re going to do it.”

That grit is rooted in his upbringing. His father worked construction, getting up at 4:30 a.m. to commute into New York City and feed five kids. Griggs inherited not only the work ethic but the sense of responsibility that comes with it.

“I’m old-school now, I can finally say that,” he laughs. “Your word is your bond. If I tell a client they’ll be swimming by July 4th, no matter what happens, they’re swimming by July 4th. That’s your reputation. That’s everything.”

His biggest piece of advice for anyone trying to build something unconventional?

“Bet on yourself,” he says. “You want to be the person with the ball with two seconds left who actually wants to take the shot. Nobody’s coming to save you. It’s on you.”

Creativity in Spray Paint and Steel-Toed Boots

Despite the tough-guy exterior, Griggs describes himself as a softie who cries at movies and gets emotional easily. His creative process is surprisingly intuitive.

He doesn’t sit behind a screen and draft for days. Instead, he walks the site with old-school spray paint in hand, sketching the pool, patio, and pathways right onto the earth.

“It’s like when a song comes into your head,” he tells Jules. “For you, you go to the piano. For me, I start spray-painting the outline. I see the whole thing before it’s ever built—even down to the flowers.”

He laughs that he can’t draw a stick figure on paper, but give him a raw piece of land and he can see the finished space from day one.

The Lonely Road of Entrepreneurship—and Why He’d Still Choose It

Griggs is quick to point out that entrepreneurship is not for everyone.

“Can everyone be an entrepreneur? I don’t think so,” he says. “It’s lonely. There were times I didn’t know if I could make the mortgage or the payroll. People are cheering for you—but also, some aren’t. There’s jealousy.”

And yet, he wouldn’t trade it.

Being his own boss meant he could coach his sons’ soccer games, be present for family life, and build days around what mattered most. Now married 29 years to a wife who balances his high energy with a calmer presence, he knows firsthand that success without relationships isn’t success at all.

“I see a lot of people where one partner is working nonstop, and everything else falls apart,” he says. “It’s not worth it.”

Even with his own business, he refuses to let his kids skip the hard part.

“They see me come home dirty and tired,” he says. “They’re not following in my footsteps—and that’s fine. But if they ever want to come into the business, they’re not getting handed the keys. Go out, get beat up a little, learn how the world works, then we’ll talk.”

Why Breaking the Rules Might Be the Only Way to Live

For Steve Griggs, living an unconventional life is less about rebellion and more about refusing to sleepwalk through someone else’s plan.

“To me, the unconventional life is breaking something, living outside the box,” he says. “Don’t just do what everybody says you should be doing. Go for it. Bet on yourself. Don’t have regrets.”

Whether he’s spray-painting the outline of a rooftop pool, pricing a six-figure backyard renovation, or sending 5 a.m. emails so clients know he’s thinking about their project before sunrise, one thing is clear: Griggs isn’t just designing outdoor spaces.

He’s designing a life on his own terms—and inviting the rest of us to do the same.

Giveaway: Win a Copy of Straight Dirt + Personal Design Insight from Steve

To celebrate the episode, Steve is giving away a hardcover copy of his coffee-table book, Straight Dirt: New York City’s Premier Designer Tells It Like It Is.

Connect with Steve


 

Hi, I’m Jules
I’m Jules, founder of Unconventional Life, born from a dream after a near-death experience seven years ago. As a 2x TEDx speaker, global event host, multi-millionaire entrepreneur, and artist, I’m passionate about guiding you to unleash your soul’s greatest gifts. Together with my two sisters, I’ve expanded UL’s mission by co-creating Pink Lemon Agency, a creative marketing agency designed to help bring bold visions to life.
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