Jillian Mastroianni (00:00):

Welcome back from Labor Day weekend. If you’re like a lot of people, you put up an out-of-office message, tied up some loose ends, and promised yourself you’d deal with the rest on Tuesday.

But what if you didn’t come back on Tuesday? What would happen to your business? Would clients get what they’ve paid for? Would invoices get paid? Would anyone even know where to start?

Today’s question on Tuesday Triage comes from Julie in Virginia. She has an online business and wants to know: does her business need an estate plan? 

(00:39) Welcome to the Death Readiness Podcast. This is not your dad’s estate planning podcast. I’m Jill Mastroianni, former estate attorney, current realist, and your guide to wills, trusts, probate and the conversations no one wants to have. If your Google search history includes, “Do I need a trust?” “What exactly is probate?” and “Am I supposed to do something with mom’s Will?” you’re in the right place.

A few months ago, I was auditing a client’s estate plan — let’s call her Lisa. As we were reviewing her documents, she mentioned she had stock options through her employer. I asked to see her signed agreements. She didn’t have them — and honestly, she thought it wasn’t a big deal.

I encouraged her to ask for copies anyway. When she finally got them, we realized it wasn’t stock at all — it was units in a limited liability company, or LLC. And once those units vested — meaning she gained ownership of them — she also became a member of that LLC, bound by the terms of its operating agreement. 

(01:49) She didn’t have a copy of the operating agreement either, which isn’t unusual. So, I encouraged her to get that, too. She was a little annoyed with me at the time — she figured her employer had all the documents, so why should she keep her own copies?

Fast forward a couple of months, and she called to tell me she’d just been terminated. The first thing she said was how relieved she was that she’d pushed to get those documents when she did. Asking for them after the termination would have been awkward — and it probably would have weakened her bargaining position.

When we reviewed her separation agreement, I noticed that while her employer was making promises about her LLC units, the LLC itself wasn’t a party to the agreement — which meant the LLC wouldn’t be bound by any of those promises. 

(02:39) Lisa hired an employment law attorney to make sure she fully understood the agreement and that it was signed by the right parties, including the LLC.

That experience reinforced something I tell every client: estate planning is about agency. It’s about taking ownership of your life and your business, and making sure you’re in the strongest position possible — especially when life takes unexpected turns.

That’s why Julie’s question really matters. She runs her own online business and wants to know whether she needs an estate plan for her business. The answer is, yes — because planning isn’t just about what happens if something goes wrong. 

(03:31) It’s about agency. It’s about knowing you have everything organized so you can grow, scale, or even sell your business from a position of strength.

In today’s Tuesday Triage, we’re going to talk about the steps you can take today to protect your business, your income, and the people who depend on you.

When I think about my own business, I don’t just think, ‘What happens if I die tomorrow?’ Instead, I think, ‘What if I sold the business tomorrow?’ That shift makes the planning more strategic.

Because whether you sell, retire, or… don’t come back after a long weekend, the systems you have in place will determine whether your business survives — and whether your family inherits a legacy or a logistical nightmare.

(04:09) Let’s start with the foundation — your legal and structural basics.

First, make sure you have your EIN letter from the IRS. An EIN, or employer identification number, is like a social security number, but for a business. If you don’t have the letter, that’s okay — just be sure you know your EIN and have it documented.

Next, pull together your business entity documents. If you’re an LLC, that means your Articles of Organization and your Operating Agreement. 

Yes, even if you’re a solopreneur, you should have an Operating Agreement. And, the Operating Agreement shouldn’t just say what happens if you die. It should also spell out what happens if you’re incapacitated and unable to run the business yourself.

(04:58) If you’ve misplaced your Articles of Organization or any other documents you’ve filed with the state, don’t panic. You can usually request copies from your state for a small fee. Back when I was practicing, if a client owned a business, I would always request a full set of documents from the Tennessee Secretary of State to make sure what the client believed about their business matched what was actually on file. At the time, it cost just $17 per entity — and it was always money well spent.

Those state records typically include annual reports, your Articles of Organization, any amendments to the Articles, and sometimes a certificate of assumed name. For example, my legal entity is Oversimply, LLC, but I operate under an assumed name — or DBA (Doing Business As) — Death Readiness, so I keep my assumed name certificate with my other governing documents.

(05:58) But here’s something important to note: your Operating Agreement is not filed with the state. So make sure your signed copy is accessible.

These are the papers that prove your business exists — and, more importantly, they guide what happens to it when you’re not able to make decisions.

With your governing documents in place, the next area is banking and financials. And, it’s an area where things can fall apart quickly if you’re not prepared.

If you have a business checking account and you’re the only one with signing authority, that’s a problem waiting to happen. If your bank has a local branch, go there in person. Ask them exactly what they need to add a second signer to your account. Most banks will require a simple banking resolution, and many even have a template you can fill out.

(06:49) This step is critical because even if your Will says your spouse or your best friend inherits everything, your business expenses won’t wait for probate. Think about payroll for employees or payments to your independent contractors. Bills keep coming, and someone needs the authority to keep the business running in your absence. 

So, who should that person be? It depends. If you have a trusted right-hand person in your business — someone who already understands your systems and operations — they may be the right choice to keep things running, at least temporarily. 

If you don’t have that person in your business, think about someone you trust who is organized, detail-oriented, and capable of coordinating with your attorney, accountant, or other advisors to keep things on track until a more permanent plan is in place.

Make sure the person you’ve chosen to step in is named in your operating agreement, and that your will or trust also references the operating agreement.

And if the decision is made not to continue your business, this same person can handle winding things down and making sure everything is closed out properly.

(07:59) Then there’s your accounting. Do you have a system for tracking expenses and income? Can someone easily tell who owes you money and to whom you owe money?

Accounting can be really tedious work. I actually outsource it. My cousin Nora handles all of my bookkeeping, and it’s such a relief because it lets me stay focused on other parts of my business — like creating episodes for this podcast. 

Outsourcing doesn’t have to be expensive, and it can give you the peace of mind that your records are organized, up-to-date, and ready for anyone to step in if they need to. It's also really helpful at tax time.

The more organized your books are today, not only the easier it will be for someone else to step in when needed, the easier it will make running your business every single day.

(08:50) With your governing documents and financials squared away, let’s talk about your people.

Who are the key people in your business? Start with your clients. Do you have a system that clearly tracks what projects are pending, what’s been delivered, and what’s coming up next? 

If someone had to step in for you tomorrow, could they see exactly where you are in providing services — or would they be starting from scratch?

Also, think about adding a ‘death or incapacity’ clause to your client contracts. This kind of clause is common when there’s one key person — in this case, you — who’s essential to delivering the service. It basically says that if you’re unable to perform the work because of death or incapacity, the contract can be terminated. Having this in writing protects you, your business, and your clients by setting clear expectations upfront.

(09:45) Then, think about your team, if you have one. That could be employees, independent contractors, such as a virtual assistant or a bookkeeper, or even people you collaborate with regularly, such as a marketing consultant.

Make a list of those relationships, their contact information, and their roles. It doesn’t need to be fancy, but it should be accessible and clear. 

If this episode has you thinking about what would happen to your business — or your family — if something unexpected happened, I can help you get organized and create a plan that truly reflects your goals.

My Estate Planning Support Services are designed to make the process clear and manageable. Whether you’re just getting started, reviewing your existing plan, or trying to make sense of complex legal documents, I’ll help you:

• Gather, organize and review your personal, financial, and legal information

• Find and vet an attorney in your state 

• Prepare for and navigate meetings with that attorney

• Understand your estate plan in plain language

• Make sure everything is implemented and organized so your loved ones aren’t left guessing.

To learn more or get started, visit deathreadiness.com/services and I’ll include the link in the show notes. Together, we’ll make sure your plan — and your business — are ready for whatever comes next.

(11:08) Now let’s talk about your recurring expenses because you probably have more than you realize.

For example, I have a good amount of subscriptions alone - a few of mine are Monday.com, Clio, Canva, Riverside, and Simplecast.

If you’re not here, someone needs to know what’s being paid for, how to access those accounts, and how to cancel or manage them.

Now let’s move on to operational knowledge and systems — because honestly, this is where most businesses fall apart. Why? Because everything lives in your head.

One of the best things you can do is create standard operating procedures, or SOPs, for your repetitive tasks. For example, I have SOPs for how to post a blog on my website and how to publish a podcast episode.

(11:56) And documenting your processes isn’t just for emergencies. It’s also how you grow. You can’t delegate what you haven’t defined.

I’ll give you an example from my own business. I don’t post blogs to my website anymore — my cousin Nora handles that for me. But here’s the flip side: just like Nora needs to know the details of certain parts of my job if I didn’t come back after Labor Day, I need to know how she does her job, too. Nora, like me, is human — she’s susceptible to emergencies and, she deserves a vacation every now and then.

Having those processes written down makes everything more resilient and keeps your business running smoothly.

Next up is digital assets and branding. This is one of those areas that’s easy to overlook until it becomes a problem.

Make a list of your domain names and trademarks, along with the renewal dates for each one. These are small details that can create big headaches if no one knows where to find them.

For example, I have domains for deathreadiness.com, thedeathreadinesspodcast.com, and a few others. I keep a simple list that notes who the provider is — in my case, that’s Squarespace — and the dates when each one is set to renew.

(13:12) Let’s move on to content and marketing infrastructure because in most businesses, content management isn’t as streamlined as it should be.

So here’s my system: I keep separate folders for each month’s content and subdivide each folder into social media posts, blogs, email newsletter copy, and podcast audio. 

I also have a master document that links to all of my Canva content, like my podcast cover art, lead magnets, informational flyers, business stationery, even merchandise.

This isn’t just about staying organized in case you’re gone. It’s about making your content easy to repurpose, keeping your branding consistent, and, if you ever want to sell your business, making it more attractive to a buyer.

(13:58) Let’s talk about insurance and risk management.

For my business, I carry three key types of coverage:

• A business owner’s policy for general liability protection.

• Cybersecurity and digital media coverage 

• And professional liability insurance

It’s not enough just to have these policies in place. Someone else needs to know that these policies exist, where to find them, and when they renew. 

And as an advanced consideration, think about using life insurance to fund a smooth transition. The payout can provide the cash flow your business needs to stay afloat while your family or team figures out the next steps.

If this episode has you thinking about your business — or your family — and what would happen if something unexpected came up, I can help. My Estate Planning Support Services make the process simple and manageable. I’ll help you get organized, find the right attorney in your state, and make sure your plan is clear and ready to implement.

Learn more at deathreadiness.com/services — the link is in the show notes.

(15:09) So, after everything we just discussed, it really comes down to this — how you run your business every single day.

Think of your business as something you’re preparing to hand off — whether that’s to a buyer, a family member, or just a future version of yourself.

Because planning well doesn’t just prepare you for the worst — it makes your business stronger and more valuable every single day.

And don’t forget — keep this information with your other estate planning documents, and share access details with the people who would need it.

Thanks to Julie from Virginia for suggesting this topic.

And if you enjoyed this episode, please share it with someone who could benefit from it.

(15:55) This is Death Readiness, real, messy and yours to own. I’m Jill Mastroianni and I’m here to help you sort through it, especially when you don’t know where to start.

Hi, I'm April, Jill's daughter. Thanks for listening to The Death Readiness Podcast.  While my mom is an attorney, she’s not your attorney.  The Death Readiness Podcast is for educational and entertainment purposes only.   It does not provide legal advice.  For legal guidance tailored to your unique situation, consult with a licensed attorney in your state.  To learn more about the services my mom offers, visit DeathReadiness.com.