Real Estate Pros · September 9, 2025 · 15 min listen

Insurance Secrets Every Real Estate Investor Must Know | Richard Smith Interview

Show summary

In this episode of the Real Estate Pros podcast, host Q Edmonds interviews Richard Smith, an insurance expert specializing in risk management for real estate investors. Richard shares his journey into the insurance industry, emphasizing the importance of specialization and understanding insurance contracts. He discusses the challenges faced in the insurance world, particularly during hurricane season, and highlights the need for investors to be proactive in protecting their assets. Richard also offers valuable advice on building relationships and networking, as well as insights on the importance of continuous learning for business success.

Key takeaways

Once an investor reaches 15 properties (one-to-four family units, or units in one building), it's time to evaluate whether your insurance advisor is actually reading the full policy language rather than relying on a generalist local agent.
Insurance premiums have doubled or more over the past five years for many investors; this is driven by underwriting data and reinsurance constraints, not arbitrary decisions by insurers.
During hurricane season, quotes can be pulled if a storm comes within 100 miles of landfall, so investors need to make coverage decisions quickly or risk losing a quote entirely.
Civil instability or unrest in a city can cause underwriters to pause issuing new policy quotes in that area, making location and timing critical factors in coverage.
Specializing and turning away clients who aren't a fit has been key to Richard's business growth over his eight years in insurance, rather than trying to be a generalist who handles home, auto, life, and business insurance for everyone.
Build your own mailing list and send a personal monthly newsletter (including personal/family updates) to stay memorable to your network, rather than relying solely on social media for relationship building.
Treat yourself as the business owner responsible for everything until you hire professionals - learn to read contracts and understand taxes rather than waiting until problems arise to get help.

In this episode

About the guest

Richard Smith is an insurance professional who has worked in the industry for eight years, following in his father's footsteps after a brief stint owning a couple of real estate properties himself. He specializes in risk management for real estate investors, construction operators, and property managers across most of the U.S. (excluding Hawaii, Alaska, Rhode Island, and currently Washington D.C.), focusing on clients with 15 or more one-to-four family units or larger multifamily portfolios, up to those with 50+ locations and hundreds of units.

Listen to the audio

“Help investors that own $20 million or more better protect their assets because here's what I find. Look, this is to all the viewers out there. If you're just starting, go find somebody locally that you trust that can put together a good policy for you.”
Richard Smith

“People don't read the insurance contract. And if you don't, even the quotes you get can be subject to change for based off different things.”
Richard Smith

“If you're a small business, you are everything, right? You're your own legal department until you find a lawyer. Hire the professional and get your contracts right.”
Richard Smith

insurance for real estate investorsrisk managementhurricane season insurancereinsuranceproperty insurance contractsnetworking and relationship buildingscaling a real estate portfoliospecialization in insurance

Questions answered in this episode

At what point should a real estate investor hire a specialized insurance advisor instead of a local generalist agent?

Richard Smith says once you hit 15 properties (defined as 15 one-to-four family units, or units in one building), you should start thinking harder about whether your advisor is actually reading all the policy language. Below that level, he recommends finding someone locally that you trust to put together a good policy. As you scale higher and serve bigger needs, the contracts change and a specialized advisor becomes more valuable.

Why do insurance premiums keep going up for real estate investors?

Richard explains that if you've looked at your premium over the past five years, you've probably seen it double or more. He says this isn't because insurance companies are "out to get you" - it's data driven, based on understanding the risk being taken on, and tied to reinsurance, which dictates a lot of what companies can do.

How does hurricane season affect insurance quotes for investors?

Richard gives an example of a client with about 50 properties in Florida during hurricane season. He notes that insurance quotes can change based on conditions - if a hurricane is within 100 miles of landfall, insurers can pull the quote. He stresses that decision making speed matters: if a client takes too long, it could be too late to lock in coverage.

Can civil unrest or instability in a city affect getting a property insured?

Yes. Richard mentions he's seen underwriters at different companies put a hold on new policy quotes in a city experiencing some sort of riot or instability. This is one more reason he stresses that property owners need to think carefully about location and timing when insuring assets.

What's a simple way for investors to build their network and stay memorable?

Richard recommends creating your own mailing list and following up consistently, even if you only own a couple of properties. He suggests sending a personal monthly newsletter that includes personal and family updates so people remember you, rather than relying only on social media. Over time, this keeps you top of mind so contacts remember your buy box and reach out when they have deals.

What's the biggest mistake Richard sees small business owners and investors make?

Richard says the number one failure point is not realizing that as a small business owner you are everything - your own legal department, etc. - until you hire the right professionals. He advises investors to slow down, learn to read contracts, understand taxes, and get professional help rather than waiting until something goes wrong.

Resources and links

Full transcript

Richard Smith (00:00)

⁓ Help investors that own $20 million or more better protect their assets because here’s what I find. Look, this is to all the viewers out there. If you’re just starting, ⁓ go find somebody locally that you trust that can put together a good policy for you. Once you get to 15 properties, let me define that.

15 one to four families or.

units in one building okay once you start to scale their start to really think about. The advisor you’re hiring are they are are they reading all the policy languages- ⁓ because for me once you get to higher scale. And serving bigger clients the needs change- ⁓ the contracts change. And my advice I’m able to be more valuable to them so.

starts out including in my business we’re you know going.

Quentin (02:31)

Hello everyone, welcome to the Real Estate Pros podcast. I am your host Q Edmonds and I am super, super excited today about my guest that I have here. He’s making serious strides in the insurance world. He makes sure that investors have the insurance that they need, right? You talk with property management, contractors, just a little bit about what he does. I’m gonna let him go ahead and tell you more about what he do. And so I’m really excited.

to introduce you guys to Mr. Richard Smith. Sir, how you doing today?

Richard Smith (03:03)

I’m good. I’m good, Q. Yeah, no, thanks. Yeah. Thanks for having me on.

Quentin (03:04)

Absolutely.

No, absolutely, man. Listen, I am excited for our viewers to take a peek through your lens, right? I’m excited for you to talk about what you do, for you to educate us, for you to take us into your world. And so I want to dive right in, man. Take us into your world. Let us know what’s your main focus these days and also what markets are you operating in? You already got me once, but go ahead and tell us.

They don’t need to know that, but that’s between me and you. But yeah, tell us what markets y’all bringing in,

Richard Smith (03:36)

Yeah yeah.

Yeah no just so I- I specifically work with- anybody involved in real estate. As far as a risk management standpoint so if you think like insurance like as a real estate investor insurance on your your asset. As if you’re a construction operator- you know what general liability insurance if you’re a property manager like professional liability you’re all of those things is is what I do I do across the country.

I don’t have the reach to get to Hawaii and Alaska. I’m not in Rhode Island and right now we’re staying out of Washington, D.C. But you know pretty much everywhere else is a good area of focus. And I particularly on the real estate investment side just because there’s no confusion. If any investor that has ⁓ fifteen like one to four families or more or if you have a lot of different multifamily properties even if it’s just one.

know, 50 unit property. That’s typically where I start to play, upwards of people that have 50 locations and hundreds of different units at different places. So a lot of different complexities. So ⁓ yeah, that’s the markets and that’s a little bit about what I do.

Quentin (05:33)

Absolutely. And so I would like to know, if you don’t mind telling me why insurance? Like where did the passion come from for you to really dive into the insurance world?

Richard Smith (05:44)

Yeah it started at birth- now my my my dad was in the industry and I kind of followed his. His footsteps if you will- took a little bit of a sidetrack for. For a second- was in real estate only about that much- owned a couple- yeah ultimately you know I chose this and- it’s been a strong eight years- ⁓ you know helping the real

Quentin (05:58)

Yeah.

Absolutely, love it man. Eight years, That’s a good chunk of time, man. And so I know you have your own process. I know you have the things that work well for you. So what’s been the key to keeping that machine running smoothly, the things that you do?

Richard Smith (06:21)

specializing I think- you the insurance guys. Are historically known for kind of being like a generalist you know the little. Your family insurance agent where they’ll they’ll do like your your home your auto your life insurance and then if you start a business. You know they can do the business and do some small things but- if you really want to differentiate yourself. ⁓

the clients that I take on, don’t take on everybody. Not everybody’s a fit for me. ⁓ I turn people away, which sounds crazy, but I do. ⁓ it’s if you know what you’re looking for, you know what type of client you want, you can be very specific in how you build your business around that.

Quentin (07:08)

Absolutely. Now I’m not sure what is that vernacular is within your world, but I know there are moments when things get real. there’s, want to say deals go sideways. I’m not sure if you would categorize them as deals, but is there a time within what you do kind of when things kind of felt maybe seem like it was falling apart and you had to pivot fast, had to kind of think on your feet? Like, is there any stories like that you can share within the insurance world?

Richard Smith (07:35)

Yeah, I it happens at the micro level, not so much at like the macro level of operating the business, right? ⁓ Because again, you know, I work for a extremely large brokerage that’s, national. ⁓ But as far as the micro is concerned, you know, for an example, you know, I’m working on a case right now in Florida where ⁓ they own about 50 different properties in a certain town. And ⁓

know it’s hurricane season so like- it’s- people don’t read the insurance contract. And if you don’t even the quotes you get can be subject to change for based off different things so you know for example for hurricane starts blowing. And you know is within a hundred miles landfall they could easily pull that quote so where that comes into play is. The decision making process and if the client takes their time. It could be too late- ⁓

there’s also other things like you know for example- instability you know if there’s a give me an example with with being as as as in the middle as I can be but in terms of- some sort of riot happening. In a certain city I’ve seen underwriting. At different companies put a hold on any new policy quotes going in there so. You know for a property owner you have to think. You know location location location like where is this property. And.

have the aspect of- ⁓ the insurance industry in general so without getting into specific details there’s levels to it. And there’s what’s called reinsurance that dictates a lot of what a company’s can do. If you’ve been looking at your insurance premium for the past five years you’ve probably seen you pay double or more. And there’s there’s reasons for that. And it’s not because the big bad ugly insurance companies out to get you it’s really not it’s data driven to understand what the risk of taking on so.

not understanding that you’re at a disadvantage. And if you don’t know that and you can’t explain it to your client or you you literally can’t read a contract know what is going to be a pitfall for them. You know that’s where you’re setting yourself up for for failure but knowing all those things in the white elephant or the white black swan sorry of like hey you have a hurricane coming. You have to you have to take each individual deal as. You know.

thinking about all those things.

Quentin (09:52)

Yeah,

absolutely. I think you hit the nail on the head when you said most people don’t read the contract. Most people are not up to date with the changes in the clause. And I definitely hear you on that. And most people just don’t know. And so I’m glad you spoke to it. glad, again, I’m glad we got your unique lens on the show today. So let me ask you this. What are you most focused on solving or scaling next? What’s the next real goal for you?

Richard Smith (10:52)

15 one to four families or.

starts out including in my business we’re you know going.

Serving smaller clients and things like that you know where I’m at now. It’s growing and growing and growing and growing so. You know that’s that’s typically- not typically that’s my next area folks.

Quentin (12:02)

Absolutely. No, I love it. And of course, you know, either the next move can either compound things or create total chaos to put in on how you play it. And it sounds like you’re reaching for the stars. So I know. But you’ve been there for a long time. So I know you’re able to take the chaos and put a system and make it beautiful for a beautiful outcome. So I appreciate you again, your insight. Listen, a lot of people even listening there like early in their journey or they look in the level up. And I think they may benefit hearing this from you.

Richard Smith (12:30)

Thank

Quentin (12:31)

When it comes to building relationships and growing your network, what’s made the biggest difference for you?

Richard Smith (12:36)

event actually follow up- ⁓ create your own mail list doesn’t matter what it doesn’t matter if you’re an investor let’s say you’re an investor you own two properties. Create your own mail list you market to the realtor like all the realtors that are trying to market you. It doesn’t you marketing whatever just. Be in touch with them what does that mean people say let’s stay in touch all the time. It’s easier to stay in touch. These days social media but honestly get their email.

once a month, send them your own personal newsletter that talks about your family, that they always remember you. You keep drawing that and ⁓ people are gonna remember you. They’ll remember that you’re, hey, you work in IT and you have these two properties, but by the way, you’re looking for another one. What’s your buy box? What is that? So like always actually build that. It takes work so people aren’t going to do it. ⁓

But if you actually do that, even for your personal, they’ll remember you, they’ll know you as a relationship through this digital age.

Quentin (13:32)

love it. Thank you. Thank you so much. You know, I always like to ask this question. You’ve dropped some gems. I mean, you took us into your world. You took us, you know, let us peek through your lens. Is there any other inspiration, any other encouragement that you feel like you want to leave the audience or any kind of other advice? Because again, this is your unique lens, especially when it comes to insurance. And I’ll be honest, I haven’t had too many insurance people want, so I’m going

Richard Smith (13:54)

Okay.

Quentin (13:59)

I’m enjoying this conversation, but through your lens, is anything you feel like the audience may need to know and that you can help them out.

Richard Smith (14:46)

Yeah, I got two things. The first is if you’re, if you are signing up yourself to go be an investor or whatever business you’re in, be the investor, be the actual business owner, take the ownership that you’re taking on. Don’t sit, don’t complain about certain circumstances and be ready to learn things. I post things at times on my LinkedIn and my newsletter.

The number one thing that I see small businesses fail to realize is that if you’re a small business, you are everything, right? You’re your own legal department until you find a lawyer. You’re your own XYZ until this. Hire the professional and get your contracts right. This goes back to what I was saying at the beginning. If you think that, you know, I’m just going to go and make deals, might be a sales might be a strong suit for you. And, you know, maybe you need a partner to come in there, but

you have to slow down and realize that, if I really want to be successful, I’m to have to learn how to read a contract. I’m going have to learn about taxes. I’m going have to learn these things. don’t wait. Don’t be reactive to that.