Aaron Seawood has never shied away from a challenge. In fact, what drives Seawood, who made the jump from the top of the Compass ladder to Triplemint in the midst of a pandemic, is embracing the unknown and taking the necessary risks to move himself and his clients forward.

“I was the original Steve Jobs and Mark Zuckerberg, much to the chagrin of my parents,” he said of his decision to leave a full scholarship at Howard University behind. “You have a full academic scholarship, and it is not meant to be taken lightly to have college paid for. For me to leave before graduating were the early signs of me being a risk-taker.”

“I just was playing it out saying, ‘Okay, I’ll graduate, I’ll get a degree,’ but it just didn’t resonate with me,” he added. “I loved [Howard], but it was one of those things that I just felt like, ‘You know, I need to go create.’ I’ve never been afraid to do that.”

Seawood’s heart took him to New York City in 1995 just as the city’s vibrant hip-hop scene transcended the boroughs and reached the mainstream. The city was brimming with energy and opportunity, which Seawood tapped into as an entry-level employee answering phones and running errands at Queen Latifah’s management company, Flavor Unit.

“I started out working with the Flavor Unit answering phones,” he said. “I worked my way up to artist management, working with platinum artists, and then transitioning to [becoming] the Director of A&R (artists and repertoire) for East Coast Virgin Records.”

For 13 years, Seawood worked with some of the world’s most notable artists, such as LL Cool J, Outkast and Faith Evans. He even ventured out and founded his own management company, Risk Music Management, before deciding to walk away from it all in 2008.

“The music industry, at the time when I was in it, there was just this wave,” he said with a glint of excitement. “It was amazing. It was something that had not been exposed on TV yet, and there was a lot of magic being made before it became formulaic.”

“There was a real genuine push for artistry and artists doing their best work and not necessarily what would get sales, and a shift started to happen where that started to change,” he added. “The convergence of those two things put me in a place where I felt like I wanted it more for the artists than they did, and I’m somebody that really prides myself on being all in.”

Seawood said he had “brief interactions” with the real estate industry during his music management career, and after seeing a colleague successfully transition from music to sales, he decided to make the jump, too. He quickly wrapped up his real estate licensing classes and hung his hat at Anchor Associates, a midsize rental firm in Manhattan.

“I got licensed and I moved really quickly because if I do it, as I said before, I’m all in,” he said. “I started in July and I crushed it; I came right in and had some really big months, did really well, and was immediately at the top of the company.”

“Then we had the bottom fall out,” he added, referring to the market crash that led to the Great Recession. “I just kept my head down and kept working.”

Seawood said his early successes at Anchor motivated him to stay in the industry while his previous experience in the music industry taught him how to persevere. With that in mind, Seawood set his sights on the luxury end of the rental market, with the understanding those renters would one day be the buyers who’d help him launch a career in sales.

“I wanted to set myself up for today and tomorrow,” he explained. “So if I work with a renter that can rent a two-bedroom [unit] for six grand as opposed to three grand, that person may most likely be in a place where they will buy and their buying power may be greater as well.”

“I think it was partially influenced by, to be fair, coming from the music industry where I regularly worked with celebrities, artists and people of that ilk,” he added. “That’s what my exposure was and so it just naturally felt right that I would operate in that space and work with high-end rentals.”

By 2010, Seawood solidified his place as one of the go-to brokers in New York City’s luxury rental scene and began fielding recruiting calls from some of the city’s largest brokerages. But, it took two years before he came across an opportunity at Corcoran that he couldn’t pass up.

“I’m fiercely loyal. I’m not someone to hop around,” he said. “I feel like if you’re in a situation or partnership, you honor it until it no longer feels right.”

“I got to a place where I realized I didn’t know what I didn’t know, and I didn’t like that,” he added. “I thought, ‘if I’m really going to be this advocate for my clients, I need to know everything.'”

Much like his tenure at Anchor, Seawood quickly shot up the ranks at Corcoran where he “cut his teeth and filled in the blanks” as a luxury real estate salesperson. However, by 2015, Seawood was ready to make another move to a burgeoning behemoth: Compass.

“Compass came calling, and I was super excited. I didn’t have an open wound [with] Corcoran. Things were fine,” he explained. “It was just something intriguing about Compass and what it felt like was, ‘Oh wow, this [place] speaks to me.'”

Compass’s scrappy culture reminded him of his days at Flavor Unit, Seawood said, and the brokerage’s in-house approach to marketing, technology and agent support was an engaging value proposition. Seawood leaned into Compass’s start-up environment and co-founded the brokerage’s Sports and Entertainment Division alongside Kofi Nartey.

Once again, Seawood experienced immense success at Compass and founded a team. He watched as the brokerage transformed from a homegrown New York City outfit to a national brand gunning for competitors like Realogy and Keller Williams.

“I was one of the early culture carriers there. I spent five years there and grew with them from just a few hundred people to obviously now over 18,000 [agents] around the country,” he said. “That was a really great experience until June of last year, where, again, there wasn’t an outward wound, but just feeling kind of unsettled.”

That’s when Seawood decided to take his three-person team to Triplemint, where he felt the brokerage’s “curated and thoughtful” approach to business was what he needed to properly serve the roster of actors, musicians and athletes on his client list.

“[Triplemint] is small and it’s thoughtful; it feels more like fine dining with proper proportions — not trying to be too big, too quick,” he said while noting that protecting his clients’ privacy was getting harder and harder to do at Compass. “This isn’t to knock on where I was — I loved it [and] a lot of my dear friends are at my previous firm.”

“You have to give it your all and be loyal and all of that,” he added while emphasizing there’s no ill-will toward his previous brokers. “But there still has to be an eye towards, ‘Does it still feel right? Is the value proposition still serving me? Am I able to do my best work here?‘ Because ultimately, I work for the client. It’s not about me.”

Looking back on his career, Seawood realizes he’s made plenty of decisions that most people would shake their head at, similar to how his parents reacted to his decision to leave college a year before graduating. But Seawood said he believes in his talent, reputation and intuition to lead him in the right direction.

“The No. 1 thing I learned is that trust transfers,” he explained. “If you’re a good person and you do things the right way, with high character and high integrity, people will roll with you wherever you are, and that’s clients included.”

“Another thing that’s been really helpful for me is that I’m never attached to the outcome. I’m attached to the process,” he added. “When you’re attached to the process, you’re not motivated by the commission — you’re not motivated by anything other than honoring what is the right thing to do at this moment in time.”

“So I like to say, I’m a master of the moment.”

Looking forward, Seawood said he’s working on mastering his moment at Triplemint and leading their charge into Brooklyn. He’s also seizing more moments with his wife, son and daughter, reading his collection of 500 e-books and collecting vinyl records that remind of his days in the music industry.

“Nothing against digital, but there’s nothing like putting on a record and playing a song and just hearing it as it was intended to be heard,” he said with an air of wistfulness. “You know, they always say that the road to success can be circuitous and I think I’m proof of that.”

“I’ve definitely bumped my head along the way and everything hasn’t worked out — I don’t want it to come off like everything is rosy,” he added. “Maybe the timing wasn’t the best, but what I’ve learned over the years, is to just really be thoughtful about it and operate from a place of optimism.”

Email Marian McPherson

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