A Conversation with Rick Sykes

The Marrying Millions star reflects on his colorful life

Rick Sykes, star of the Lifetime reality show Marrying Millions, is nothing like I expected. Waiting for Rick by the Miami Beach Marina, I anticipated a typical Northeasterner who retired to Florida. Someone obsessed with their golf game and portfolio balance, not much else.

The premise of the show revolves around a group of millionaires and their relationships with significantly less wealthy partners. When I first heard about the show, I imagined a group of octogenarian Palm Beachers buying pearls and poodles for retired strippers.

 What I got instead was an intimate look inside loving, and sometimes very complicated, relationships. Rick and Erica in particular confounded my expectations.

The couple, with a 40+ year gap, seemed to epitomize what happens when love runs headlong into real world challenges like money and aging. Throughout the show Rick’s friends pushed the idea that she was a gold digger, something he never entertained. When the show left them at the end of season two she had just bailed on their wedding due to family pressure. It was honestly a hard moment to see, the emotions were raw.

If you watch the show closely enough the real Rick peeks out at you, but I didn’t know what I was truly getting until he invited me aboard his yacht. As we escaped the rain below deck, I started to get the real story.

When I asked him why he chooses to live on a boat instead of a more conventional home, he chuckled and said he got that question a lot, “It’s on the water, it’s nature”. Most yacht owners I’ve met are in it for the status, but I got the sense from Rick that he genuinely loves the lifestyle. As the interview continued a surprising adjective kept popping into my head, bohemian.

“If you remember Woodstock, you weren’t there” Rick quips about his experience at the legendary 60s music festival. The only part of it he remembers clearly is seeing Jimmy Hendrix play the national anthem. He admits it took him sixteen hours to find his car when the festival finished. In his early teens Rick would go down from Connecticut to Greenwich to see Bob Dylan play. These aren’t typical resume bullet points for the country club set.

His professional career also reflects an eclectic and rebellious approach to life. After a stint in juvenile lock up Rick learned a major lesson, maybe not the one intended, that you should “do things, just don’t get caught”. 

Starting young, Rick dug graves to buy his first MGA sports car, the very car that took him to Woodstock. In no particular order he’s been in the jewelry business, built a movie studio, and owned the largest strip club in Connecticut. Some of his ventures have worked out, others have been flops, but they are all interesting experiences.

The strip club brings a cheeky smile to Rick's face. “Who ever said there’s no sex in the champagne room, well that’s not true” he said when talking about the club. This hedonistic chapter was very sex drugs and rock and roll. 

The movie studio did not pan out, but it led him on another adventure. The project went south after the government land he purchased was found to be contaminated with Chromium. Rick’s lawyers advised him to move to Brazil because there’s no legal reciprocity. In the end he reached a deal with the Feds, “I lost a ton of money, and then I went on to other ventures, and by other ventures I mean I partied my ass off in Brazil”. 

Rick retired eighteen years ago and moved, like the cliche previously mentioned, to Palm Beach. It was not for him. Neighbors complaining about the noise from his Harley was the last straw, and he literally pulled up anchor and sailed for South Beach.

Right now he’s living his best life. Officially single, Rick enjoys the company of a bevy of ladies. His go to move is taking them on a motorcycle cruise, a good excuse for them to wrap their arms around him. After a wild romantic ride broadcast on national TV, it seems like he’s landed on his feet.

Marrying Millions, Erica, and True Love

While he’s an old school guy, Rick found Erica in a very new school way, on Instagram. 

He slid into her DMs and they started chatting, but nothing came of it until a few months later when she invited him to accompany her to a concert in West Palm Beach. Sparks flew and they started a long distance relationship, she was in Sarasota across the state from Miami. After a few months he asked her to move onto the boat with him and she said yes.

For all his braggadocio around women, In his heart Rick is a romantic. Describing their instant connection, Rick explains “when something feels right, you don’t know exactly what's going on, but something feels right”. We sat around his dining room table, and he showed me pictures of them together, both looked like they didn’t have a care in the world. 

Erica encouraged Rick to join her on YouTube and that’s how Marrying Millions discovered them. Rick just wanted to make Erica happy and somewhat reluctantly agreed to be on the show. Presciently at the time he predicted to Erica “If we do it I can guarantee it’s the end of our relationship”. 

The relationship did end, a fact Rick attributes to COVID as much as the show. They have not been in contact, staying friends with exes is not his style, “I told Erica if and when we broke up I wouldn’t be friends with her, I want them to go on and enjoy their life”.

While clearly heartbreaking, this turning point inspired Rick to dive into his most recent project, his book Drugs and Roses.  The first volume of a proposed trilogy, the memoir delves into the stories that make Rick Rick. He asked me to read the dedication out loud, it was to a list of women he’s had relationships with. The list was long, and Erica was not the last name on it. In an altruistic move, a portion of book sales are going to the Pink and Blue breast cancer charity, giving something back to the opposite sex.

Me Too, PC culture, and the likely demise of the show

I didn’t want to bring it up but Rick talked about the touchy subject of his fellow castmates Bill and Bri. Bill Hutchinson is a Dallas real estate magnate, and according to the Dallas Morning News has been charged with several sexual assaults. Hutchinson’s lawyers have called the charges “total malarkey”, but they’ve been enough to derail the show.

Rick feels bad for Bill, Bri his fiancé, and their families. He also expressed sadness that the show would not continue because of the controversy. In terms of Bill, Rick is reserving judgment, “Whatever Bill did, or is accused of, I love being an American, you can’t say he is guilty until he’s proven guilty”.

These are not abstract issues for him, Rick faced his own troubles around women. When he was running his Strip Club, Rick says he was “set up like a bowling pin” by a girl interested in money. He did not elaborate about the incident, but clearly it has had an impact on his worldview.

Thinking about himself, Rick says “If I live my life and do something the norm doesn’t like, if I get caught I get caught, I don’t hurt anybody, I try to never hurt anybody.” He did however recognize that times have changed and as a media personality he’s got to be a little cautious. “Things are a lot different today with the #metoo crap and all this other stuff, I understand that you have to be a little more careful with what you say”.

In our conversation there was a certain nostalgia for the more freewheeling days of yore. Rick describes doing lines of cocaine off a bar with cops outside. Those officers were friends but today, he opines, “cops would give their grandmother a ticket.” He also misses some of the more permissive sexual mores, “Today you would think we’ve move forward, we’ve moved back”

Despite this nostalgia Rick is still looking to the future.

The Zen of Rick Sykes

Like many successful people, Rick has a bias towards action. 

When he thinks of something, he just does it. Take Scuba diving. Most people go to classes and get certified, not Rick. One day he wanted to try it so he went out, bought all the gear, and jumped on in.

As someone who can be overly pensive, I respect this characteristic. In the end, it pays to be optimistic because it leads to action. There is also an epicurean element to his personality, Rick lives in the moment and not in the past or the future. When I asked about Miami’s prospects as a city, he refused to prognosticate.

Throughout our conversation he reiterated that he’s the happiest person he knows, going so far as to say he has run into trouble with people being jealous of his happiness. Self help gurus love to talk about gratefulness, and if you listen to Rick you see they have a point.

A shoot from the hip attitude mixed with a positive mental outlook are pushing Rick, now seventy, into new creative endeavours. We had to end our interview because he needed to rehearse lines for an upcoming film. In the last week he’s been on three podcasts and is gearing up to complete his second book. At half his age I wish I had half his energy. 

Rick is the prototypical Florida Flaneur. He has a wide range of passions, from film to classic cars, and has had many business adventures. While Marrying Millions is most likely over, I don’t think we’ve seen the last of Rick Sykes.