Real Estate Nerds 54: "Hurricanes, Hotels, and Honesty" with Greg Dickerson - Best Deals

Real Estate Nerds 54:

Bad Beats

"Hurricanes, Hotels, and Honesty"

Greg Dickerson
Real Estate Investing Expert
Real Estate Nerds
Episode 54: "Bad Beats"

Listen to the Podcast Here:

Greg Dickerson is a man of many titles, real estate developer, investor, and business coach and mentor being a few. He joins Scott today to talk about his best deal that took over 2 years to purchase. This episode of Real Estate Nerds gets into the hang ups that can be caused by litigation in real estate world.

Hurricanes, Hotels, and Honesty

Greg starts by giving his background on real estate:

[1:50]  Greg talks about his first real estate deal, a  landflip that he partnered with a friend on. He then continues on to talk about what types of projects he typically works on, usually as a contractor and facilitator.

[4:50] Greg talks about how he mostly learned the ropes of real estate on his own. He was introduced to the real estate game by a friend but after his first couple of investments he was on his own.

[5:23] Scott and Greg start to get into the details of his Best Deal which was a hotel damaged by Hurricane Isabel.
  • Earning a hefty commission as a real estate agent for the neighboring lot.
  • Taking the seller of the hotel to court (for over a 2 year period) for trying to back out of the contract.
  • The eventual profit from the property after litigation.

[11:50] Scott and Greg get into the details of the legal strategy used by the hotel owners.

[13:20] Greg talks about what he learned from the whole ordeal:
  • Ironclad contracts
  • Documenting communications
  • Integrity
  • Lawsuits are a tool
  • Judges and juries matter

[15:04] What Greg has learned from his involvement in legal proceedings.

[18:20] Scott and Greg talk about the importance of documentation, record keeping, and paper trails.

[20:28] Greg and Scott go into more detail on the tolls being involved in litigation can take:

  • Emotional and familial
  • Physical
  • Financial
[25:30] Services Greg offers and his contact info (434-326-3903).

Listener Resources

Thank you for joining us on today’s episode of the Real Estate Nerds Podcast. For even more free educational resources on real estate investing and the law, check out the Royal Legal Solutions blog. You can also reach our host Scott Smith directly, connect with him on LinkedIn, subscribe to the Royal Legal Solutions YouTube channel, or join our investor community on Facebook.

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About Greg Dickerson

Greg is an entrepreneur, real estate investor and developer and over the past 20 years he has bought, developed and sold over $200 million in real estate, built and renovated hundreds of custom homes and commercial buildings and started 12 different companies from the ground up.

Greg is an expert on the topics of real estate and entrepreneurship. He has spoken at mastermind events around the country, he’s been a guest commentator on Fox Business with Neil Cavuto, The Dave Ramsey Show and is a regularly interviewed on some of the top real estate investing and business podcasts today.

Greg has always been a very active member of his church and community serving on the boards of several non-profit organizations including the Home Builders Association, Remodeling Council, Community Foundation, Heart Association, Cancer Center, Education Foundation, Babe Ruth Softball, YMCA, Parks and Recreation, SPCA, PTA, School Boosters, Youth Ministry Council, Fellowship of Christian Athletes and Christian Surfers.


Connect with Greg via his phone number or email:

  • 434-326-3903



When making business decisions that affect your long-term goals, like what types of investments to make with your retirement dollars and which vehicles to use, it really is best to be aware of all of your options. We frequently talk about the Solo 401(k) and Self-Directed IRA as tools for funding your retirement. But what about life insurance? And what about the stock market? What if we told you there is a tool that allows to to reap some benefits of both? It’s called Indexed Universal Life Insurance–and some investors have found it a useful addition to their retirement plans.

What Is Indexed Universal Life Insurance?

Indexed Universal Life Insurance (IUL) plans are a variety of permanent life insurance plan that features a cash-building element. One primary benefit of these plans is that the policy holder gets some of the gains of being associated with the stock market without all of the risk Wall Street is famous for. This is in no small part because of how these policies are designed. IULs earn in part because they are directly linked to a market index, such as the Dow or the S&P 500.  Any gains remain within the policy, albeit a cap rate will limit how much you can make. However, you are protected during a particularly bad year for your index with an IUL. The worst case scenario with these plans is that you make nothing, but you never actually lose money no matter how poorly your index performs. The protection of your principal is actually derived in part from the same cap rate that limits your gains.

How much money do policyholders stand to make? Historically, returns run between 5-9%. The S&P Index has actually returned at 9-11%, but the upside limit on UILs stems from the account’s cap rate. For this reason, many advisors argue that the UIL can make a wise addition to a retirement or estate plan once more traditional and self-directed accounts are maxed out.

Tax Benefits of Indexed Universal Life Insurance (IUL) Plans

There are three key tax benefits of IULs. First, you may pay into the policy with pre-tax or after-tax funds. Withdrawals from the policy may be made tax-free if you are under 59 1/2. Such withdrawals are regarded as loans, with your death benefit serving as collateral. Any funds paid out to the beneficiary are also tax-free, including normal benefits upon your passing. This is true regardless of their value.

Ask the Experts at Royal Legal Solutions About Your Retirement Planning Options

Regardless of where you are in the retirement planning process, Royal Legal Solutions an assist you. We have extensive experience educating investors about self-directed investment options. Many of our investor-clients love our Solo 401k information, product, and compliance services. Our Self-Directed IRA services can also be helpful for retirement planning, as the SDIRA is yet another vehicle that allows you to diversify and take total control of your investments. To determine which of the available retirement planning strategies are best for you, consult with one of our experts at Royal Legal Solutions. You may also contact us with any questions you may have about your options.