A lot of times as business owners, nobody sat us down and explained how to protect what we build. No one in our family talked about trusts, wills, probate, or what happens to everything we worked for when we are gone. Most of us figured it out too late. Our families paid the price because we never figured it out at all. I Wish Somebody Told Me is the show that fills that gap. Visit shadrachco.com (https://shadrachco.com) to build your financial strategy and take the first step toward protecting everything you have built.
Every episode breaks down estate planning, asset protection, and wealth transfer in plain language. No jargon. No gatekeeping. No assumptions that you already know how this works. Because most of us were never taught. If you own a home, run a business, have children, or have anything worth protecting this show is for you. Topics we cover: how to avoid probate, the difference between a will and a trust, how to fund a trust properly, protecting your business for the next generation, estate planning for blended families, how to transfer wealth without court involvement, and the mistakes that cost families everything they built.
Hosted by Jason Malone, founder of Shadrach & Co. Licensed estate planning advisor with a background in institutional finance and Wall Street. Jason built this practice specifically to give our community access to the same level of planning that wealthy families have used for generations. New episodes every two weeks. Subscribe so you never miss one. This podcast is for informational purposes only and does not constitute legal or tax advice.
Last year six out of ten business owners asked a lender for money. Only four out of ten got everything they asked for. shadrachco.com (https://shadrachco.com) Two out of ten got nothing at all. In almost every one of those noes, the money was there. What failed was the paperwork. Using Federal Reserve data from the 2025 Small Business Credit Survey, we break down what lenders actually see when your file hits their desk, why books built for your tax preparer work against you, and what the personal guarantee on your loan really puts at risk. Then we walk through a ninety day plan to get fundable. Five steps, no new sales required. If you have been declined, partly funded, or approved at a rate that made you sick, this one is for you. Book a 20 minute capital readiness call at shadrachco.com (https://shadrachco.com).
20 Aug 2026
Who Gets Your Money When You Die? The Beneficiary Mistake Most People Overlook
You have a will. You may even have a living trust. But who is actually listed as the beneficiary on your 401(k), IRA, and life insurance? Learn more at fortitudefinancial.co (https://fortitudefinancial.co)
In this episode of I Wish Somebody Told Me, host Jason Malone breaks down one of the most overlooked parts of estate and financial planning: beneficiary designations.
We discuss why certain beneficiary designations can take priority over instructions in your will, the difference between primary and contingent beneficiaries, when you should review your accounts, and why major life events like marriage, divorce, children, and remarriage should trigger a beneficiary check.
You'll also learn why retirement accounts, life insurance, trusts, and your overall estate plan need to work together instead of being treated as separate pieces.
You worked hard to build your wealth. Make sure you have a plan for where it goes.
Presented by Fortitude Financial (https://fortitudefinancial.co).
This podcast is for educational purposes only and should not be considered individualized legal, tax, or financial advice.
19 Aug 2026
Living Trusts 101: Protect Your Assets, Avoid Probate & Build Your Legacy
🏡 You created a living trust…but did you FUND it? Signing the documents is only the beginning. At FortitudeFinancial.co (https://FortitudeFinancial.co) you will find all you need to know about forming your trusts.
A properly structured estate plan may include transferring or coordinating assets such as:
🏠 Real estate
💰 Bank & investment accounts
🏢 Business interests
📈 Retirement accounts and beneficiary designations
🛡️ Life insurance policies
The key is making sure your assets and beneficiary designations actually work together with your estate plan. A trust sitting in a binder isn't the goal. A properly coordinated plan is. Want to learn more about protecting what you've built and creating a legacy for your family?
Schedule a consultation with Fortitude Financial.
🔗 FortitudeFinancial.co
#LivingTrust #EstatePlanning #RevocableLivingTrust
18 Aug 2026
The Howard Hughes Estate Saga, Billions, Decades of Chaos, and No Will
Howard Hughes built one of the largest fortunes in America. But when he died in 1976, there was one major problem: no authenticated will could be found. Visit FortitudeFinancial.co (https://FortitudeFinancial.co) What followed was an incredible estate saga involving competing heirs, alleged wills, years of court battles, and the infamous “Mormon Will” — a mysterious handwritten document that supposedly left part of Hughes’ fortune to a gas station operator who claimed he once rescued Hughes in the Nevada desert.In this episode of I Wish Somebody Told Me, hosted by Jason Malone, we unpack the Howard Hughes estate saga and the financial lessons hiding behind the headlines.We explore:
What can happen when someone dies without a valid will
Why owning assets doesn't necessarily mean you control what happens to them after your death
How unclear estate planning can create costly family and legal disputes
The difference between a will and a revocable living trust
Why creating a trust isn't enough — it also needs to be properly funded
How estate planning can help you maintain greater control over your home, business, investments, and legacy
Howard Hughes had billions. Most of us don't.But you don't need billions to have an estate-planning problem.If you own a home, business, rental property, investment accounts, life insurance, or anything else you've worked hard to build, you need a plan for what happens next.Because sometimes the most expensive financial lessons are the ones we wish somebody had told us sooner.
🎙️ I Wish Somebody Told Me
Presented by Fortitude Financial
Money. Wealth. Business. Legacy.
The lessons we often learn too late.
Disclaimer: This podcast is for educational and informational purposes only and does not constitute legal, tax, or individualized financial advice.
16 Aug 2026
Cash Flow Management for Business Owners
Cash flow is not the same as profit. And that difference is exactly what puts otherwise successful businesses out of operation. Visit fortitudefinancial.co (https://fortitudefinancial.co) to build your estate plan and take the first step toward protecting everything you have built. In this episode of I Wish Somebody Told Me, Jason Malone breaks down cash flow management in plain language and explains why profitable businesses still fail when cash is not managed properly. If you are a solo founder, small business owner, or growing company, mastering cash flow gives you leverage, flexibility, and control. It allows you to make better decisions, plan ahead, and stop running your business in reaction mode. If you want to build a business that is sustainable and not just busy this episode is for you.
In this episode:
What cash flow actually is and what it is not
Why revenue and profit do not equal money in the bank
The most common cash flow mistakes business owners make
How to forecast cash flow so you are not guessing every month
Simple systems to stabilize cash flow and reduce stress
How cash flow management connects to your long term estate and business succession plan
00:00 Cash Flow vs Profit
02:00 Why Profitable Businesses Still Fail
04:00 The Most Common Cash Flow Mistakes
06:00 How to Forecast Your Cash Flow
08:00 Simple Systems to Stabilize Cash Flow
10:00 Building a Sustainable Business
This content is provided for educational purposes only and is not intended as individualized legal, tax, investment, or financial advice. Estate planning laws and strategies vary based on individual circumstances and jurisdiction. Consult qualified legal, tax, and financial professionals regarding your specific situation. Estate planning services provided by Fortitude Financial.
15 Aug 2026
Nobody Told Us That Owning It and Controlling It Are Two Different Things
Most people assume that owning something means they control what happens to it. That assumption is exactly what leaves families stuck, accounts frozen, and businesses stalled when something unexpected happens. Visit fortitudefinancial.co (https://fortitudefinancial.co) to build your estate plan and take the first step toward protecting everything you have built. In this episode of I Wish Somebody Told Me, Fortitude Financial breaks down why estate planning is not about death. It is about control. Who steps in when you cannot. Who signs when you are unavailable. Who keeps your business moving when you are not in the room. And what happens to everything you built if none of that is documented properly. We cover why a will alone is not enough, why incapacity is a bigger immediate risk than death for most business owners, how trusts create continuity instead of confusion, and why the absence of a plan is itself a plan — just not one you wrote. In this episode: Why ownership and control are not the same thing
What happens to your assets without proper documentation
How incapacity can freeze accounts and stall businesses
Why a will does not avoid probate
How a properly funded trust creates continuity
The three most common estate planning gaps business owners ignore
Why estate planning is part of your business infrastructure not separate from it
When the right time to start and what to do next
00:00 Ownership Does Not Equal Control
02:00 What Happens When You Cannot Act
04:00 Why a Will Is Not Enough
06:00 How Trusts Create Continuity
08:00 Estate Planning for Business Owners
10:00 The Three Gaps Most People Ignore
12:00 When to Start and What to Do Next
This content is provided for educational purposes only and is not intended as individualized legal, tax, investment, or financial advice. Estate planning laws and strategies vary based on individual circumstances and jurisdiction. Consult qualified legal, tax, and financial professionals regarding your specific situation. Estate planning services provided by Fortitude Financial.
Most people think estate planning is only about what happens after you die. It is not. Visit fortitudefinancial.co (https://fortitudefinancial.co) to build your estate plan and take the first step toward protecting everything you have built. In this episode of I Wish Somebody Told Me, Fortitude Financial breaks down the fundamentals of estate planning and explains why having a plan matters regardless of your age or net worth. Estate planning is about control, protection, and preserving what you have built while you are alive and after you are gone. We cover the role of a complete estate plan, why relying on a will alone may not be enough, and how revocable living trusts and irrevocable trusts serve very different purposes. You will learn how a revocable living trust can help with probate avoidance, incapacity planning, privacy, and the transfer of assets. We also explore why some families and business owners use irrevocable trusts for asset protection, estate tax planning, long term care strategies, and multi-generational wealth preservation. Most importantly, we explain why there is no single trust that is right for everyone. Your estate plan should reflect your family, assets, business interests, risks, and long term goals.
In this episode:
What estate planning actually means
Why estate planning is not just for wealthy people
The four questions every estate plan should answer
Revocable living trusts explained
Trusts vs wills
The biggest mistake people make after creating a trust
Irrevocable trusts explained
Revocable vs irrevocable trusts
Asset protection and estate tax planning
Business succession and legacy planning
Choosing the right estate planning structure
00:00 Estate Planning Is About More Than Death
02:15 What a Complete Estate Plan Should Include
03:40 Revocable Living Trusts Explained
06:05 Irrevocable Trusts Explained
08:15 Asset Protection, Taxes and Legacy Planning
10:05 Revocable vs Irrevocable: Which Is Right for You?
This content is provided for educational purposes only and is not intended as individualized legal, tax, investment, or financial advice. Estate planning laws and strategies vary based on individual circumstances and jurisdiction. Consult qualified legal, tax, and financial professionals regarding your specific situation. Estate planning services provided by Fortitude Financial.
15 Aug 2026
What Is an IUL and Why Every Business Owner Needs to Know About It
Most business owners are looking for ways to protect their income, grow their wealth, and leave something behind for their family. Visit fortitudefinancial.co (https://fortitudefinancial.co) to build your estate plan and take the first step toward protecting everything you have built. What most business owners never hear about is one of the most powerful tools available to do all three at the same time. In this episode we break down Indexed Universal Life insurance and how business owners can use it as more than just a death benefit. We cover how an IUL builds cash value tied to a market index with a floor that protects you from losses, how that cash value grows tax deferred and can be accessed tax free, and how it fits inside your estate plan to protect and transfer everything you have built. If you have been looking for a way to grow wealth outside of the stock market, protect your business, and create a tax advantaged legacy for your family this episode is for you. What we cover in this episode: what an Indexed Universal Life policy is and how it works, how business owners use IUL for tax advantaged wealth accumulation, how IUL fits inside a trust for estate planning purposes, the difference between term life and permanent life insurance for business owners, how to use your policy cash value while you are still alive, and why an IUL inside an irrevocable life insurance trust protects your estate from unnecessary taxation. This episode is for informational purposes only and does not constitute legal or tax advice. Estate planning services provided by Fortitude Financial.
00:00 – Universal Life Insurance for Business Owners
01:48 – Building Your Cash Value Asset Base
03:04 – Using Life Insurance for Business Growth
05:08 – Universal Life Insurance & Estate Planning
07:27 – Wealth Transfer, ILITs & Legacy Planning
08:20 – Final Thoughts
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
1 ratings
Contact I Wish Somebody Told Me
Guest appearances
Does not typically book guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Host of I Wish Somebody Told Me?
Claim your podcast to manage its listing and keep your show details accurate.
Pod Engine is an independent podcast discovery and analytics service and is not affiliated with or endorsed by this podcast. Artwork and show content belong to their owners. Full legal notice.
Explore this show Podcast research with Pod Engine
