Ep 269: The Necessary Evil

About This Episode
Here's something that almost never gets talked about in personal finance: most people are both overpaying for insurance and dangerously underinsured — at the same time. In this episode, David Chudyk, CFP® breaks down exactly how that happens, which gaps most commonly cost people everything, and the four-step annual insurance audit every wealth-builder should be doing.
What You'll Learn
- Why insurance gets ignored — and why the industry is designed to let it happen
- The four most common places people overpay (including one hiding in plain sight for business owners)
- The single most underutilized piece of asset protection available — and why it costs less than most people think
- The three insurance gaps that can end a business, not just hurt it
- A four-step annual insurance audit you can actually do
- Why your financial advisor and your insurance agent are probably never talking to each other — and what that gap costs you
Episode Timestamps
- 0:00 — Cold Open: The two insurance problems most people have simultaneously
- 2:00 — Why insurance gets ignored: the set-it-and-forget-it trap
- 6:00 — Where people overpay: collision on old vehicles, duplicate coverage, whole life misuse
- 12:00 — Where people are underinsured: umbrella policies, life insurance drift, disability
- 18:00 — The business owner's trifecta: key person, cyber liability, E&O
- 23:00 — The annual insurance audit: four steps to close the gaps
- 28:00 — Close and how to connect with David
Key Takeaways
- Most people are carrying policies designed for who they were — not who they are now. Income, assets, and risk profile all change. Insurance usually doesn't keep up.
- A $1 million umbrella liability policy costs roughly $150–$300/year. It's the most underused, underpriced form of asset protection available to individuals with meaningful net worth.
- About 20% of Americans with $5M+ in assets carry no umbrella policy — leaving their full net worth exposed in a lawsuit.
- Business owners face three specific coverage gaps that can end a company: no key person insurance, no cyber liability coverage, and no errors & omissions (E&O) policy.
- Your ability to earn income is your most valuable financial asset — and most people have almost no protection for it through private disability coverage.
- The biggest structural problem: your financial advisor and your insurance agent are almost never talking to each other. That gap is where wealth gets destroyed.
The Annual Insurance Audit: 4 Steps
- Step 1: Pull every policy you have — home, auto, life, disability, umbrella, all business lines.
- Step 2: Match coverage to current reality — net worth, home value, business size, family situation.
- Step 3: Check for the five gaps — umbrella, disability, life insurance adequacy, business trifecta (key person / cyber / E&O), and outdated or duplicate coverage.
- Step 4: Make sure your advisor sees the full picture — someone needs to look at insurance and wealth planning together.
Connect With David
- Free 20-Minute Vision Call: weeklywealthpodcast.com/vision
- Business Owner Exit Score: weeklywealthpodcast.com/prescore
- All Episodes & Resources: weeklywealthpodcast.com
00:00 - Untitled
00:00 - Understanding Financial Planning
03:30 - Understanding Insurance Audits
08:37 - Understanding Umbrella Insurance Policies
10:31 - Understanding Umbrella Policies and Life Insurance
13:13 - The Importance of Disability Insurance
18:52 - Understanding Coverage: The Myths of Full Coverage in Insurance
Quick question.
Speaker AWhen you think about financial planning, what do you think about?
Speaker AI bet you probably think about something that resembles last week's episode, like, should I buy SpaceX?
Speaker AIf I buy a little bit of SpaceX, am I going to end up rich and wealthy?
Speaker AAnd yes, we should ask some of these questions.
Speaker ABut some of the things that we also need to be looking at with our financial planning are boring, are not fun, but they protect us.
Speaker ASo today we're talking about insurance.
Speaker AWe're going to help you to do an insurance audit on your life and make sure that most of your gaps are protected.
Speaker AMy name is David Chudick.
Speaker AThis is the Weekly Wealth Podcast.
Speaker AAnd here we go.
Speaker BWelcome to the Weekly Wealth Podcast.
Speaker BI am certified financial planner David Chudick.
Speaker BThis podcast and my wealth management practice are both designed to help the mass affluent to live better lives by how.
Speaker AThey handle their money.
Speaker BWe talk about financial strategies, prosperous mindsets, and simply how to build true wealth.
Speaker BSo come on and let's enjoy this journey together.
Speaker AWell, let's get started with this week's episode.
Speaker ABut real quick, if this episode is useful to you, share it with someone.
Speaker AI'm not running ads, I'm not sponsored.
Speaker AI'm just trying to make the show worth your time every week.
Speaker AAnd a share goes a long way.
Speaker AAlso, don't forget to check out our social media.
Speaker AYou can check us out on YouTube, on Instagram, and on Facebook.
Speaker AAll right, so this week we're talking about insurance.
Speaker AA lot of times it's referred to as, like, a necessary evil.
Speaker AAnd I get it.
Speaker AI don't even like paying for my own insurance.
Speaker ANow, in addition to my work as a financial advisor, I also own a property and casualty insurance agency.
Speaker ASo the guy who owns an insurance agency, he doesn't like.
Speaker AHe doesn't like paying for his insurance.
Speaker ASo I can understand why you might have some misconceptions about your insurance.
Speaker ANow, insurance is largely a set it and forget it industry.
Speaker AYou buy a policy, you get a renewal, you complain that the price went up, you pay it, and you move on.
Speaker ATypically, your agent isn't calling you every year to say, hey, you made a lot more money last year.
Speaker ALet's revisit your liability coverage.
Speaker AThat's just not how most of it works.
Speaker AAnd the result is that most people are carrying policies that were designed for who they were, not for who they are.
Speaker ASo you bought a homeowner's policy when the house was worth $400,000.
Speaker ANow it's worth $700,000.
Speaker AAnd you've also done $150,000 renovation.
Speaker ADid you tell your insurance carrier about the renovation?
Speaker ADo you know the difference between market value and reconstruction value?
Speaker ASo these are a lot of things that we should be thinking about that can help us to fill the gaps of your insurance coverage.
Speaker AAnd, and, you know, I love the business owners.
Speaker ADid you start your business five years ago with two employees and now you have 12?
Speaker ADid your general liability and workers comp get updated accordingly?
Speaker ASometimes, often not.
Speaker AWhat about your life insurance?
Speaker AYou got a life insurance policy when you're in your 30s and your net worth was a fraction of what it is now.
Speaker ADoes that still match your need?
Speaker ARarely.
Speaker ARarely does it.
Speaker ASo this isn't about blame.
Speaker AThis is about a system that doesn't naturally prompt you to revisit these things.
Speaker AAnd you, you know, many financial advisors, they have almost no desire to talk about your property and casualty insurance.
Speaker ASo it's not their expertise, it's not what's in their wheelhouse, but it's something that's very, very important.
Speaker ASo today I'm going to walk you through this, because an annual insurance audit should be as normal as filing taxes.
Speaker AIt's just not talked about that way.
Speaker ALet's talk about overpaying on insurance or what you think might be overpaying.
Speaker ABut I want to introduce a concept to you that's very important.
Speaker AOkay?
Speaker ASo let's think about it this way.
Speaker AInsurance simply protects your money.
Speaker ANothing more, nothing less.
Speaker ASo let's say you're driving your car and you run a stop sign and you hit me and I have an injury.
Speaker AMaybe I have a very bad injury and I'm in the hospital for months and months.
Speaker AWell, somebody is going to pay for my injuries.
Speaker AIt's either going to be you or it's going to be your insurance company.
Speaker ASo wouldn't you rather it be your insurance company instead of you?
Speaker AOkay, so that's the first thing a lot of people say.
Speaker ATheir car insurance protects their car.
Speaker ATheir home insurance protects their home.
Speaker ANo, your home insurance protects your money.
Speaker ABecause if your house burns down and you have to build a new one and pay for it, that's coming from your money.
Speaker AAll right?
Speaker ASo let's think about it that way.
Speaker ANow let's also think about the cost of insurance and the concept of expensive insurance.
Speaker AThe most expensive policy, and listen to this very carefully, is the policy that doesn't do what you thought it should do at the time of claim.
Speaker AOkay?
Speaker ASo the policy that doesn't do what you thought it would do at time of claim is the most expensive policy.
Speaker ASo Sometimes people say, well, I have car insurance, but they might have what in my state is minimum liability limits, which is $25,000.
Speaker ASo that would give $25,000 towards any one person's injuries if they cause that much damage.
Speaker ANow, I don't know if you've been in the hospital or if you' seen medical bills, but $25,000 covers maybe a couple hours in the emergency room.
Speaker ASo, yes, in that case, you would have car insurance, but no, more than likely it's not adequate to protect your wealth.
Speaker ANow, with that being said, let's look at some places where you might be carrying coverage that just isn't worth it.
Speaker AOkay?
Speaker ASo part of your car insurance that pays for your vehicle if it's damaged is called physical damage, and that would be compreh and collision.
Speaker ANow, if you have a car that's worth, I don't know, $6,000 per year, and maybe the collision or comprehensive portion of it.
Speaker ASo let's say you're doing the wise thing and you own a car, it's paid off, it's not super flashy, but it's not worth a tremendous amount of money.
Speaker AAll right?
Speaker AThat's what a lot of smart financial people do.
Speaker ANow, in this case, maybe you should talk to your insurance agent and say, hey, if I decide to retain the risk of the vehicle, meaning that maybe I remove comprehensive, maybe I remove collision, and if I hit a deer, I'll just pay for the vehicle to get repaired.
Speaker AIf I my vehicle gets stolen, I'll just pay for it to be replaced.
Speaker AOkay?
Speaker ASometimes it makes sense, and you'll save enough money on your insurance to justify removing those coverages.
Speaker AOkay?
Speaker ASo it's important to make decisions based on facts, not making decisions based on what you think the facts are.
Speaker ASo step number one is to look at your comprehensive and collision coverage on old vehicles.
Speaker ATalk to your insurance agent and see how much money it would save you if you remove those coverages and determine if it makes sense to either retain that risk or to keep it transferred to the insurance company.
Speaker ANow, on your home insurance, some places where you might be able to save money is let your insurance company know if you've done any updates to the home.
Speaker ASo if you've done any major electrical updates, plumbing updates, roofing updates, things like that, oftentimes there are discounts that you can have.
Speaker AThen also, many carriers give discounts if you have more than one type of policy with them.
Speaker ASo maybe you have home insurance and auto insurance with the same company if you bundle.
Speaker AOftentimes there is A bundle.
Speaker AThere's a bundle discount.
Speaker ASo again, work with a great local independent insurance agent.
Speaker AKnow where your discounts are.
Speaker ANow another place where you can potentially save money.
Speaker AAnd again, this one gets complicated.
Speaker AThere are a lot of different factors, but when you're using whole life or, oh, don't even get me started, a properly structured index universal life policy.
Speaker AThe people on Instagram and TikTok that talk about those drive me nuts.
Speaker ABut when you're using those as a savings vehicle, oftentimes it just maybe doesn't make sense.
Speaker AThere are times where buy term and invest the difference just will get you much better numbers.
Speaker ASo if you have a permanent life insurance policy and you've never had someone walk you through the actual illustrated returns against your alternative, that's worth doing.
Speaker ANow, where have I seen people dangerously underinsured?
Speaker AWell, the first one is if you have no umbrella policy or one that's too small.
Speaker ASo this is the single biggest miss that we'll see.
Speaker AAn umbrella policy sits on top of your home and your auto liability coverage and picks up where those leave off.
Speaker ASo we're talking an extra million, 2 million, $5 million of liability protection.
Speaker AAnd here's the thing, umbrella policies are typically very cheap.
Speaker AAn umbrella policy can run a couple hundred bucks a year.
Speaker AYou know, 150, 300, $500, something like that.
Speaker ANow, it's going to be based on your underlying exposures, but you want to make sure that you are carrying enough liability insurance.
Speaker ABecause remember, what does insurance do?
Speaker AIt protects your money.
Speaker ASo if you're driving your car and if you run a stop sign and hit me again, and if me to have a million and a half dollar medical bill, your car insurance typically does not have that much liability.
Speaker AAnd then your umbrella would kick in.
Speaker ASo why don't more people have umbrella policies?
Speaker AWell, it's because nobody asks them about them.
Speaker AIt doesn't feel urgent until you need it.
Speaker AAnd because there's that underlying attitude that insurance is, quote, a necessary evil.
Speaker ABut now every dollar that we have and every dollar we ever will have is really riding on the front of our car.
Speaker ASo a missed stop sign, maybe being blinded by the sun, and pulling out in front of anything in front of somebody, all of those things in an instant can cause large, large lawsuits.
Speaker AAnd we need to be aware of that.
Speaker ASo if you have meaningful net worth, you need an umbrella policy, period.
Speaker ACall your insurance agent, tell them you want an umbrella policy, and then also ask them, hey, you know what?
Speaker AI'm counting on you to protect me.
Speaker AWhy did you never Suggest that I get an umbrella policy.
Speaker AIt's really an inexpensive policy and a lot of coverage.
Speaker AAll right?
Speaker ASo umbrella policies, make sure you have one.
Speaker ACall your insurance agent and get one today.
Speaker ANow, life insurance is another place where people may be underinsured.
Speaker AYou know, you talk to people all the time and they're like, yeah, I have life insurance.
Speaker AYou know, I had a $50,000 policy back when I was 25.
Speaker AOkay, well that's great.
Speaker AThat's better than nothing.
Speaker ABut now you're 40 and you're making $350,000, and if you die, your family not only loses you, but they lose your paycheck.
Speaker AWell, yeah, but I have life insurance, right?
Speaker AWell, yeah, you have $50,000 of life insurance, so that's not going to do that much to maintain your lifestyle.
Speaker ASo do a life insurance audit.
Speaker AA really general standard rule of thumb is 10 times income.
Speaker AThat's a starting point, not an end point.
Speaker ABut the real number depends on your debts, your dependents, your business obligations, and maintaining your family's lifestyle and what that actually costs.
Speaker APeople will say, how much life insurance do I need?
Speaker AAnd the answer really is, you don't need any life insurance.
Speaker AIt's not required by law.
Speaker ASo what do you want?
Speaker AWork with a great insurance agent or your financial advisor and talk about some of the things that you might want.
Speaker AMaybe you would want your family to be able to pay off the house.
Speaker AMaybe you would want a bucket of money that's big enough to spit off 100, 200, $300,000 a year for five years or 10 years or indefinitely.
Speaker AThen you can work backwards.
Speaker AYou can determine how much life insurance you need and you can go from there.
Speaker ASo don't just say, I have life insurance.
Speaker AMake sure that you have the right amounts and the right types of life insurance.
Speaker ANow, you know, I love the business owners and we need to talk about the business owners.
Speaker ALet's talk about some general areas that business owners can be underinsured.
Speaker ASo one of the first one is no cyber liability coverage.
Speaker ACyber liability is a fastest growing risk category for small and mid sized businesses.
Speaker AA single breach.
Speaker AClient data, financial records, ransomware that can generate costs that dwarf your general liability limit.
Speaker AMost liability policies don't cover cyber.
Speaker AIt's a separate policy and most business owners don't have it.
Speaker ASo ask your commercial insurance carrier about cyber liability insurance.
Speaker AOftentimes it comes with some training and they'll help you to take the steps that will give you a better chance of not needing it, which is a great thing.
Speaker ABut cyber liability Insurance oftentimes is not very expensive.
Speaker AWhat about E and O insurance?
Speaker AThat's errors and omissions.
Speaker AIf you provide any kind of professional service and a client claims your advice or work caused them to have financial harm, your general liability won't protect you.
Speaker AEO errors and omission is a coverage built for that exposure.
Speaker AI'm always surprised how many professional service businesses are operating without it.
Speaker AAnd here's one more place where a lot of people, business owners and employees, they forget, and that's disability insurance.
Speaker ASo your most valuable asset is going to be your paycheck, right?
Speaker AIt's your ability to earn income.
Speaker AAnd most people have almost no protection for it.
Speaker ASo Social Security disability is much harder to qualify for than most people realize.
Speaker AAnd it pays far less than most people assume.
Speaker AGroup disability through your employer typically replaces 60% of your income and stops if you leave the company.
Speaker ASo for business owners, group coverage usually doesn't even apply.
Speaker AA private disability policy that protects your income if you can't do a specific job is called own occ.
Speaker AOWN occupation coverage.
Speaker AThat's one of the most important and neglected pieces of a financial plan.
Speaker AAnd the longer you wait to get it, the more expensive it gets.
Speaker AAnd sometimes it gets impossible to get.
Speaker AAll right, the annual insurance audit.
Speaker ALike, what should you actually do?
Speaker AYou've probably been listening and saying, yeah, I kind of need to look at an umbrella.
Speaker AI'm not sure if I have one or if it's big enough.
Speaker AAnd yeah, I've been thinking about disability insurance, but I just.
Speaker AIt's hard to do.
Speaker ASo let's give you something actionable.
Speaker ASo once a year, maybe around your birthday or your business anniversary or maybe even tax season, let's do an insurance audit.
Speaker ASo let's pull every policy you have.
Speaker AThat's your home, your auto, your life, your disability, your business, everything.
Speaker AIf you have more than one agent, that's fine.
Speaker ABut you need one person looking at the full picture at least once.
Speaker AThat might be your financial advisor.
Speaker AIf I'm your financial advisor, financial advisor, I have the expertise to do this.
Speaker AMany financial advisors don't.
Speaker AIt might be a single agent you trust, but you need somebody to see it all.
Speaker ANow, step number two is going to be to match your coverage to your current reality.
Speaker ASo has your net worth grown significantly?
Speaker AYour liability limits need to grow with it?
Speaker AHas your home been renovated or appreciated dramatically?
Speaker AAre building costs much higher then your dwelling coverage may need to keep in pace?
Speaker AHave you added new employees, new revenue, new services to your business?
Speaker AYour business coverage need to reflect that, don't forget, if you're a business owner, if your exposure changes, which means that you're doing different things, you need to let your insurance company know so that they can adjust adequately.
Speaker AAll right, so then let's check for some gaps on your umbrella policy.
Speaker ADo you have one?
Speaker AIs it large enough?
Speaker ADisability insurance, does it replace income for long enough?
Speaker AAnd does it replace enough income?
Speaker AYour life insurance, does your coverage match your current financial picture?
Speaker AYour business owners?
Speaker ADo you have key person insurance?
Speaker ACyber eo?
Speaker ADo you have all?
Speaker ADo you have duplicate or outdated coverage?
Speaker AIs there anything on autopay that no longer makes sense?
Speaker AAnd then make sure your advisor knows all that you have.
Speaker AThis is one that gets skipped the most.
Speaker AYour financial advisor should know your insurance picture.
Speaker AYour insurance agent should know your financial picture.
Speaker AIn reality, those two conversations almost never happen unless you have someone who brings both.
Speaker AThat's not a plug for me, although it is an advantage of working me.
Speaker AWith me, it's a structural problem in the industry.
Speaker AInsurance and wealth management are treated as separate silos.
Speaker ABut your risk exposure and your asset protection strategy are and should be in the same conversation.
Speaker AThey should be talked about together.
Speaker ASo here's where I want to land the plane on this.
Speaker ANo, insurance is not exciting, but it actually is a little bit more interesting than you would think.
Speaker AI've had people working in my office and said, wow, you know, like, insurance is pretty cool.
Speaker AI never thought it would be interesting, but nobody admittedly wakes up on a Saturday morning saying, yes, I'd like to go review my umbrella policy, or I want to go get an umbrella policy.
Speaker AI get it.
Speaker AIt's not the most intriguing topic, but I've sat across from enough people who had something go wrong.
Speaker AThey had a lawsuit, a disability, a fire, a business crisis, and they found out too late that their coverage didn't match their life.
Speaker AAnd I can tell you with certainty that it's a worse conversation.
Speaker AThe audit that I described takes a couple of hours.
Speaker AIt might have saved you thousands of dollars in unnecessary premiums.
Speaker ASometimes it even costs you a little bit of money because you realize there's some other coverage that you need to purchase.
Speaker AIt might protect assets you've spent years building, and it might find gaps that if they ever got triggered, it would change everything.
Speaker ASo there are two ways that I can help with this.
Speaker ADirectly.
Speaker AIf you want to look at the full financial picture insurance as part of your overall financial plan, head to www.weeklywealthpod.
Speaker AThere's a 20 minute strategy call and we can look over everything together and point you in the right direction.
Speaker AIf you're looking specifically for property and casualty insurance company, that's home, auto and business, reach out.
Speaker AYou can email jillfsig.net or ashley.
Speaker AThat's a S H L E I g h@cfsig.net if that is.
Speaker AIf you're looking for coverage in a state that we're licensed, we can do the best that we can to help you out.
Speaker AOur team does this.
Speaker AIt's what we do.
Speaker AAnd unlike most insurance conversations, it's not going to feel like a sales call.
Speaker AAlright, so that is this week's episode.
Speaker AWe talked about risk management, we talked about protecting your money.
Speaker AWe talked about the insurance audit.
Speaker AIf this was useful, share it with a business owner or a friend who hasn't looked at their coverage in a while.
Speaker AThey will probably thank you.
Speaker AI'll see you next week.
Speaker AMy name is David Chudick.
Speaker AThis is the weekly wealth podcast.
Speaker ATake care of your people and have a blessed week.
Speaker AAnd here is this week's bonus episode.
Speaker ASomething that drives me nuts as someone who's been in the insurance industry, is when I hear the words full coverage.
Speaker ASo if anybody who even remotely calls themselves an insurance professional uses the word full coverage when they're talking about auto insurance, ask them very bluntly, is there anything that could ever not be covered fully?
Speaker AAnd the answer, of course, is yes.
Speaker AIf you hit, if you caused a 30 car accident and everybody was severely injured, you can't possibly have enough insurance coverage.
Speaker ASo when they give you that example, ask them, well, that would not be fully covered, right?
Speaker ASo why are you calling it full coverage?
Speaker AIsn't that deceptive?
Speaker AAnd maybe you'll even give them an education.
Speaker ABecause full coverage is not a term that exists.
Speaker AIt's not a term that is logical.
Speaker AThere's always a chance that something would not be fully covered, which is why I just get the chills when anybody who's in the insurance business uses the term full coverage.
Speaker AAll right, everybody, that is my beef and we'll see you next week.
Speaker AHave a great one.







