I Wish Somebody Told Me

Jason Malone

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 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. 

Episodes

  1. Aug 18

    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 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 willWhy owning assets doesn't necessarily mean you control what happens to them after your deathHow unclear estate planning can create costly family and legal disputesThe difference between a will and a revocable living trustWhy creating a trust isn't enough — it also needs to be properly fundedHow estate planning can help you maintain greater control over your home, business, investments, and legacyHoward 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.

  2. Aug 16

    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 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.

  3. Aug 15

    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 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.

  4. Aug 15

    Estate Planning 101: Wills, Revocable Trusts & Irrevocable Trusts Explained

    Most people think estate planning is only about what happens after you die. It is not. Visit 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.

  5. Aug 15

    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 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

About

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 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.