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The Leigh Steinberg Interview - Real Estate and Sports Agents: Two of a Kind

As you know I'm always looking to bring on guests that fill voids, or perhaps on a topic we haven't covered before. And today's guest is no different. I'm very excited to have Leigh Steinberg with us.

Leigh’s a sports super agent who’s represented NFL players, from Troy Aikman to Howie Long, to Patrick Mahomes. He was the real-life inspiration behind the movie, “Jerry Maguire” starring Tom Cruise and Cuba Gooding Jr. (“Show me the money!”)

You may think there are a thousand differences between a sports agent and a real estate agent, but the surprising truth is - they’re not that different at heart. Theoretically, they might require different skill sets, however, if you listen carefully to Leigh’s recommendations, they are the “secrets” to a successful real estate career. Hope you enjoy this one.

You can contact Leigh through his website at or if you’re interested in his Sports Business Certificate program (no experience necessary).

    “Put the client's best interests before yours. It’s the key to earning referrals.” -Michael LaFido


Three Things You'll Learn In This Episode


  •  Leigh on breaking into working with professional athletes:
    Start on the college campuses because you have good connections there. Coaches will sometimes need to move. Second, you can cold call people. People who work in sports love to talk. Third, try going to the franchises themselves, speaking to someone in community relations. Befriend both agents and financial planners because they can also make referrals.
  •  Be a good listener:
    Steinberg has found that a good luxury real estate agent is not about having top-notch negotiating skills or persuasion strategies. Athletes (as well as traditional clients) need a Realtor with good listening skills. A Realtor that’s able to prioritize and understand what they truly need. A Realtor that knows how to make it simple for them. 

  • Develop your network and brand:
    Make sure that every single person you know is aware that you’re a luxury real estate agent. Get on all the social networks and reach out to as many people as you can.  Relationships matter.  Demonstrate your expertise. For example, write an article on the problems athletes have given their uncertainty of future in home purchases. Don't fear rejection - you only need one opening.


Guest Bio:
Leigh Steinberg, premier sports agent, entrepreneur, best-selling author, and CEO of Leigh Steinberg Sports and Entertainment Holdings is best known for his work building athletes into stand-alone brands. He is often credited as the real-life inspiration for the Oscar-winning film Jerry Maguire. Leigh has represented many of the most successful athletes and coaches in football, basketball, baseball, hockey, boxing, and golf, including the number one overall pick in the NFL draft for an unprecedented eight times in conjunction with 64 total first-round picks. With an unrivaled history of record-setting contracts, Leigh has secured over $4 billion for his 300+ pro athlete clients and directed more than $800 million to various charities around the world.

Over the course of his career, Leigh has been featured on numerous national television programs, including 60 Minutes, Larry King Live, The Today Show, Lifestyles of the Rich and Famous, and many more. He has been profiled in a host of magazines, including Business Week, Sports Illustrated, ESPN the Magazine, People, Forbes, Playboy, GQ, and FHM. Leigh has been rated the #6 Most Powerful Person in the NFL according to “Football Digest” and the #16 Most Powerful Person in Sports according to “Sporting News.” 

3 Things I Wish I’d Known As A New Agent

When I became a licensed real estate agent in the fall of 2000, I wish someone would have shared with me these three words of wisdom. I would say these three are vital to help newer agents differentiate themselves and become consistent top-producing agents. 1. Be likable and be you, 2. Grow your knowledge and your confidence will grow too. 3. Diversify your portfolio of homes you represent. 

The Blockbuster vs. Netflix Solution to Capital Gains Tax w/Brett Swarts

Sometimes I'll do some high-level ninja-trick podcasts that dive deep into some really important marketing angles... and capital gains tax is one of those sticking points. 

You might be wondering what does a defunct movie rental business and a flouring, $161 million streaming business have to do with capital gains tax, let alone luxury real estate? 

It's the analogy, my brilliant guest, Brett Swarts uses to describe the advantage of using a deferred sales trust over a 1031 exchange. He's the CEO of Capital Gains Tax Solutions and an expert in alternative to capital gains tax. 

Right now, the luxury market is the hottest it's ever been. However, there are certain properties out there, at certain price points where it's still difficult to sell. It's called a buyer's market. 

That's why I have Brett with us today - to talk about a possible solution for your clients. If you're representing a seller this might help to alleviate some potential objections. 

As a matter of fact, capital gains tax is one of the top objections. 

I want to help you be able to deliver a solution to your clients that's easy to articulate... so that A, you'll win the client over and B, you have this asset that you can sell by providing a different, unique solution. 


You can contact Brett on his website at or call him at 916-886-2986.


If you're interested in becoming a deferred sales trust expert or get coaching, you can download his free ebook here:


Brett's YouTube Channel:

Brett's Podcast:


Life’s too short to feel trapped by capital gains tax.” -Brett Swarts

Three Things You’ll Learn in This Episode


✔️ The 1031 Exchange (the Blockbuster way):

The 1031 exchange, (aka Delaware Statutory Trust) is the antiquated, Blockbuster way. 

In broad terms, a 1031 exchange is a swap of one business or investment asset (like for like) for another. Although most swaps are taxable as sales, if you come within 1031, you'll either have no tax or limited tax due at the time of the exchange. 

Brett states they are the transactional way of doing things and work fine for most people. However, he advises it does not work for: primary homes, businesses, cryptocurrency, or luxury homes.


✔️ The Deferred Sales Trust (the Netflix way):

This is the transformational, polished Netflix way. 

A deferred sales trust is a legal contract between an investor and a third-party trust in which the investor’s real property is sold to the trust in exchange for predetermined future payments, (installments) over an agreed-upon period of time.

It provides an alternative to 1031 exchanges for deferring capital gains taxes.

And it can work on both primary and luxury homes, investment property, businesses, and cryptocurrency.


✔️ Privacy is Luxury:

It’s a legitimate concern with high net worth clients.

The whole process is confidential. The trust is under a made-up name that the client chooses.

The trust itself is a single entity, a business trust that only does business with that particular client. They don't co-mingle with anybody else. Everything has to be signed by them for funds to move or be invested.

Brett’s business will have all of the pieces in place to make you and your client feel comfortable as well as anonymous. There have been some celebrities that have gone through this process. 



Guest Bio:

Brett is a Deferred Sales Trust expert, capital gains tax deferral expert, investment real estate expert, multifamily broker, and the founder of Capital Gains Tax Solutions – a company helping individuals to defer capital gains tax on the sale of their highly appreciated assets, eliminate the need for a 1031 exchange and deliver a transformational wealth plan so they can create and preserve more wealth.

The Importance of Empathy

Today’s topic is empathy - or more specifically, having empathy for the stress your buyer and seller clients are going through when trying to sell their home and buy a home.

Make sure that you as an agent are empathetic to your buyers and sellers….it will only make your client's experience better and will help you earn more referrals. 

Marketing Tips from La Jolla’s Top Luxury Agent

On today’s podcast, Pete Middleton, one of La Jolla’s top brokers, and I have some great tips for differentiating yourself from the competition. 

Pete grew up in a real estate family in Brockton, Massachusetts. He moved to the San Diego/La Jolla area in the early 90’s. Since then, he’s received several awards and recognition for his work in real estate.

We had an informative talk about what to do if you're dealing with a buyer’s agent that’s inexperienced. How do you work with a buyer's agent that's not well-versed in comparables, or maybe the agent or their buyer doesn't see the home's value or agree with your comparables.

A powerful strategy that Pete uses is emphasizing "payment" over asking price. 

Before using this strategy, be sure to talk with your lender first so you’re able to break it down and articulate it to the buyer’s agent (and possibly the buyer). Practice the K.I.S.S. “Keep It Simple Stupid” Principle (or, “Keep It Super Simple”, for those of a more delicate disposition).


You can text Pete at 858-922-3377 or email him at


Part of negotiating is making your client feel like they’ve won.” 

Michael LaFido

Three Things You’ll Learn in This Episode

Terms vs. Price: 

Pete’s properties list the terms, rather than the listing price because terms show people what’s attainable. Just like when you go to lease a car. The salesperson will get you off the price of the car and gets you to focus on the monthly payments. 


Know How to Break Down Numbers:

This skill can separate you from a lot of luxury agents if you really know your financing and you really know how to break down numbers. And believe it or not, people love breaking down numbers.

Keep it simple, and visual:

Some clients will need it broken down into simple terms. Having visuals is a great way to do it.  So, utilize those bullet points, graphs, and pictures. The vast majority of the population are visual learners.  

Guest Bio:

Pete’s been working in real estate since the early 90s. After receiving several awards and recognitions, including being the #1 salesperson when he was at RE/MAX associates, he established his own brokerage, Middleton & Associates. 

Middleton & Associates made a name for itself by quickly becoming one of the top five La Jolla brokerages since opening in 2010. In 2013, the brokerage completed 188 transactions totaling over $120 million in sales volume.

In 2014, Coldwell Banker acquired the assets of Middleton & Associates and welcomed Middleton’s agents into their brokerage. The merging of these two brokerages had a significant impact on La Jolla’s elite real estate market.

He now leads the Pete Knows Team, a group of handpicked elite eXp agents, all trained to provide excellent service to their clients. The team specializes in areas such as La Jolla, Pacific Beach, Solana Beach, and Del Mar.

Filling Your Listing Pipeline

You may be talking with some prospects who are interested in selling this summer or “later in the year”. What can you do right now for those sellers?

I have some advice for any agent looking to start off strong this summer of 2021. 

Working with Professional Athletes in Real Estate w/Jordan Stuart


On this week’s show, I spoke with Jordan Stuart, founder, and CEO of Next Move. He’s a seasoned agent who’s an expert in closing transactions with athletes. He’s recently branched out into helping people in the military find homes across the country. 

We talked about various topics from what not to do when working with a professional athlete, getting referrals and testimonials, smart strategies for delivering 5-star service, and the importance of having a clean car. 

You can contact Jordan at

"The biggest mistake an agent can make is not listening to their client.” -Jordan Stuart

Three Things You'll Learn

  • Buyers need a trusted advisor:
    When working with an athlete they’re counting on you to be the expert advisor. You need to able to understand and evaluate your client’s wants and needs so you can speak their language and provide them with a logical action plan. Be an active listener. How you communicate with them should not be any different than how you treat your regular clients.  

  • Celebrity endorsements and testimonials:
    First, make sure the deal is done, the home has closed. Get them a nice closing gift. Then humbly ask for a testimonial, and respect whatever the answer is. 
  • Focus on what you can do for the client:
    Remember, the minute you make a recommendation to a client (whether it’s a home inspector, contractor, etc.), you become responsible for that experience - positive or negative. Focus your job, and everything else will work itself out.

    Guest Bio:

    As the founder and CEO of Next Move, Jordan Stuart is consistently ranked as one of the top luxury realtors in the Washington D.C.-area.

    He’s recognized nationally as an influential real estate advisor to dozens of professional athletes, head and assistant coaches, and professional sports franchise owners. 

    Jordan is the exclusive real estate consultant to Major League Soccer’s D.C. United to oversee the housing needs of the Club players, personnel, and ownership along with touch-points to each of the other Washington, D.C.-area men’s and women’s pro sports franchises.

    Jordan has been featured in Forbes, The Washington Post, Washingtonian,, and The Washington Business Journal.  

A New Designation for the Global Real Estate Community

I'm excited to announce there is a brand new Diversity Designation. I'm proud to say I'm one of the co-founders of this brand-new Diversity Designation called the ‘Certified Diversity Specialist’ (CDS). With the goal of helping agents increase their knowledge, providing the tools and resources to help them work with more buyers and sellers, and helping them differentiate themselves among a diverse population. To learn more about the designation, listen to this podcast. 

Learn more:

How Real Estate and Insurance Agents Help New Homeowners w/Jordan Phillips

Would you like to join me in Napa to get Certified in Luxury?

🍷 Reserve your spot now at

Usually, I have guests that are top luxury agents or team leaders. However, from time to time, I like to have various service providers that I think you would benefit from hearing from. 

Today is one of those podcasts. Today we’re talking about homeowner’s insurance. Sure, it may not be the most exciting topic, but it can add more value to a transaction.

Any type of introduction to a service provider you can offer to a client, it can be as small as a painter, electrician, a moving company, a loan officer, or title company will provide that white-glove experience to your client. You’ll look like a rock star and stand out from the competition. 

I’ve got Jordan Phillips with Goosehead Insurance with me today, who happens to be my personal insurance provider. He’s worked with a lot of high-end clients, including many professional athletes. With all homes, you want to make sure it's covered the right way.

To get in touch with Jordan, you can call him at 618-789-6400, or send an email,

"Insurance is one of those things you never know when you’re going to need it.”  -Michael LaFido

Three Things You’ll Learn in This Episode

  • Find out what’s important to your client and assess from there.

    A lot of times, your client’s got an insurance policy and has no idea what it entails. You might find that they’re under-insured, or they may have a policy that doesn’t fit their needs.

  • Don’t be afraid of being pushy.
    Many clients don't understand insurance or they don't know what they need, and it can really hurt them in the end. With this in mind, stop worrying about being pushy and focus on the added value you’re bringing to the table.

  • Does a name brand really matter?

    Whether it’s State Farm, Nationwide, AIG, etc… every insurance company will generally have the same base coverage. The big difference is in the price. However, it all comes back to the client and what’s important to them. 


    Guest Bio:

    Jordan Phillips is the owner/CEO of Goosehead Insurance Agency. His brokerage is a 100% lender and referral-focused brokerage that represents 30+ carriers which truly gives our clients something no one else can, choice. With an emphasis on quality, there is no one better when it comes to insurance for home closings. We specialize in getting our client's dream homes insured properly and fairly.

    Goosehead is currently disrupting the Insurance Industry with leading technology and a business model that works. Taking the best clients with the top companies in the insurance industry and bringing them together under one roof.



The Power of Second Chances

In this week’s message, I’d like to talk about the power of second chances.

In life, people often make mistakes and don’t get a second chance to correct them. Real estate is no different in this regard. For example, a seller may interview you but then choose to work with someone else.

So how do you stay top of mind with such a client in the event that it doesn’t work out with the other agent they chose? Listen to find out. 

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