Money Made Simple with Oakwood Wealth Partners

You have a will. Maybe you've even created a trust. But when was the last time you reviewed either one? And are you confident those documents will actually accomplish what you intended?

In this episode of Money Made Simple, Mike and Nick Lockwood welcome estate planning attorney Danielle Guerrero, Esq. of Elegy Law for a conversation about the estate planning decisions families often put off. From understanding the difference between a will and a trust to choosing the people who will make important decisions on your behalf, Danielle breaks down why estate planning involves much more than deciding who inherits your money.

The conversation explores how trusts can help families plan for incapacity, manage inheritances and provide protection for future generations. Mike, Nick and Danielle also discuss how estate planning intersects with retirement accounts, tax considerations and the financial decisions families make throughout their lives.

Perhaps most importantly, they examine what can go wrong when a trust is never funded, documents remain unsigned or an estate plan goes untouched for decades. Whether you're starting from scratch or already have documents in place, this episode offers practical reasons to revisit the conversation you've been putting off.

Chapters:

00:00 Welcome & Meet Danielle Guerrero

02:26 Why Do You Need an Estate Plan?

05:53 Wills vs. Trusts: What's the Difference?

09:00 When Should You Create or Update a Trust?

13:17 The Essential Estate Planning Documents

18:00 Understanding Powers of Attorney

26:35 Trust Design: How Should Your Assets Be Distributed?

36:17 Retirement Accounts & Trust Beneficiaries

40:00 Estate Planning Red Flags

43:30 Outdated Trusts & Changing Tax Laws

46:45 When Should You Review Your Estate Plan?

48:30 Family Dynamics, Inheritance & Final Takeaways

The word "annuity" can bring out some pretty strong opinions. For some people, it's a valuable retirement planning tool. For others, it's a financial product they'd never consider touching. So who's right?

In this episode of Money Made Simple, Mike and Nick Lockwood are joined by Matthew Manskar for an honest conversation about why annuities have developed such a controversial reputation. They share real-world examples of annuities that didn't fit the client's situation, discuss the fees and surrender periods that investors need to understand, and explain why simply labeling an annuity as "good" or "bad" misses the bigger picture.

The conversation also explores the different roles an annuity can play in a financial plan, including creating guaranteed income, supplementing a pension, providing accumulation and downside protection, or serving as a tax-deferred alternative to other conservative investments. The team also gets into an often-overlooked issue: what happens to an annuity when it's passed from one generation to the next?

Ultimately, the message is simple: the right financial product depends on the person, the plan, and the purpose. Whether you already own an annuity or are considering one, understanding what you have and why you have it is the place to start.

Chapters:

0:00 The $250,000 Annuity Horror Story

3:22 Why Are Annuities So Controversial?

5:53 Understanding Annuities: Guarantees, Risks & Fees

8:20 When Annuities Go Wrong

12:15 Income vs. Accumulation Annuities

15:30 When Does an Annuity Make Sense?

20:00 Annuities, Tax Deferral & Downside Protection

24:10 What Happens to an Annuity When You Die?

29:35 Are Annuities Good or Bad?

32:35 Real-World Examples & What to Do If You Own One

36:00 Final Takeaways

Social Security has become one of the most talked-about topics in retirement planning, yet it's also one of the most misunderstood. Every election cycle seems to bring new headlines, predictions, and uncertainty, leaving many Americans wondering what it all means for their own financial future.

In this episode of Money Made Simple, Mike and Nick Lockwood are joined by Oakwood Wealth Partners Financial Planner Mike Kish to separate fact from fiction. Together, they explore how Social Security works, why concerns about the program's future continue to dominate the news, and what today's workers and retirees should actually be paying attention to.

The conversation examines the unique perspectives of different generations, from those approaching retirement to younger investors who question whether Social Security will still exist when it's their turn to collect benefits. The team also discusses claiming strategies, the importance of integrating Social Security into a broader retirement plan, and why building your own financial independence remains one of the smartest long-term decisions you can make.

Whether retirement is just around the corner or decades away, this episode offers practical guidance to help you make informed decisions without letting fear or headlines dictate your future.

Chapters:

0:00 Welcome Back & Meet Mike Kish

1:40 SpaceX Update & Episode Introduction

4:10 How Social Security Began

8:15 How Social Security Works Today

13:20 Is Social Security Really Running Out?

19:10 Different Generations, Different Perspectives

25:15 When Should You Claim Social Security?

32:05 Should You Take Benefits at Age 62?

38:15 Social Security, Taxes & Retirement Income Planning

43:05 Building a Retirement Plan Beyond Social Security

47:15 Key Takeaways & Closing Thoughts

Everyone loves talking about stocks when they're going up.

The harder conversation is figuring out what to do after they've gone up.

In this episode of Money Made Simple, Mike and Nick Lockwood welcome Kevin Campbell to discuss one of the most common challenges facing investors today: managing concentrated stock positions and navigating the complexities of equity compensation.

Whether you've purchased shares of a company you believe in, accumulated stock through your employer, or watched a single holding become a significant portion of your net worth, success can create a new set of risks. The conversation explores why some investors become overconfident, why selling can be emotionally difficult, and how concentration can quietly reshape a financial plan.

The discussion also dives into the world of equity compensation, including restricted stock units, employee stock purchase plans, and stock options. While these benefits can create tremendous wealth-building opportunities, they often come with tax considerations, timing decisions, and planning complexities that many employees do not fully understand.

Through real-world stories and practical examples, Mike, Nick, and Kevin explain why stock ownership should be viewed within the context of an overall financial plan, not as a standalone decision. If you've ever wondered when to sell, how much risk is too much, or whether your company's stock has become too large a part of your financial future, this episode is for you.

Chapters:

0:00 Introduction & Meet Kevin Campbell

2:00 Why Stocks Are Back in the Spotlight

6:50 The Risks of Concentrated Stock Positions

11:10 SpaceX, NVIDIA, and the Appeal of Individual Stocks

16:15 Managing Risk While Chasing Opportunity

19:50 What Is Equity Compensation?

26:00 RSUs, ESPPs, ISOs & NQSOs Explained

30:35 Real Client Stories: When Stock Success Creates New Risks

34:50 The Big Question: When Should You Sell?

36:40 Taxes, Capital Gains & Planning Opportunities

38:30 Building a Strategy Around Company Stock

42:20 Key Takeaways & Final Thoughts

There are certain conversations every family knows they should have. Most just don’t know how to start.

In this episode of Money Made Simple, Mike and Nick Lockwood sit down with Celeste Gurule to unpack one of the most avoided but important topics in life planning. What happens when your parents can no longer make decisions for themselves, and how do you prepare for that moment before it becomes a crisis?

This conversation goes beyond finances. It explores the emotional realities that keep families stuck. Parents fear losing independence. Children fear overstepping. Both sides avoid the discussion, often for the same reason. They are trying to protect each other. But waiting comes at a cost, especially when the reality is that most families will face some form of long-term care need at some point.

Celeste introduces the concept of a Future Living Plan, a framework designed to help families think through not just money, but identity, community, health, living arrangements, and the roles each person will play over time. The goal is not perfection. It is progress. It is clarity. And most importantly, it is making sure your wishes are understood before someone else has to guess.

This episode is not about having all the answers. It is about starting the conversation early, approaching it with care, and recognizing that planning ahead is one of the most meaningful gifts you can give your family.

For more information surrounding the Future Living Plan and an Inventory of Information Checklist, visit the link below:

https://drive.google.com/drive/folders/1FB1agwW4ZsnCHMhmNa6zWIl2bD_MTVa3?usp=sharing

Chapters:

0:00 - Introduction

1:37 - Celeste's background and career

4:18 - Personal experiences with future living plans

7:32 - Dealing with cognitive decline

11:45 - The 7 areas to address for future living

17:40 - Starting these conversations early

27:37 - Why these conversations are so hard

34:48 - Key takeaways

39:50 - Don't let perfect be the enemy of good

41:40 - Closing remarks

Some of the most important financial conversations are also the hardest ones to have.

In this episode of Money Made Simple, Mike and Nick Lockwood step into a reality many families face but few feel prepared for. What happens when a spouse passes away or a marriage ends, and one person is suddenly left to navigate a financial life they were never fully involved in?

Drawing from personal experience and years of working with widows, widowers, and individuals going through divorce, Mike and Nick walk through both the emotional and financial sides of becoming suddenly single. This is not just about accounts and documents. It is about grief, uncertainty, and the overwhelming question most people ask in that moment. What do I do now?

The conversation focuses on helping listeners slow things down and take the next right step. From understanding what you have, to identifying what needs immediate attention, to thinking through income changes and long-term stability, the episode provides a framework for navigating an incredibly difficult transition. It also highlights the importance of preparation for those who are still married, encouraging couples to communicate, stay involved, and ensure both partners understand the full financial picture.

At its core, this episode is about more than planning. It is about protecting the people you love, reducing confusion in moments of crisis, and making sure no one is left to figure everything out alone.

Chapters:

0:00 - Introduction

3:10 - This is personal for us

6:10 - What a financial leader is doing regularly

15:15 - You've lost your spouse. Where to start?

18:40 - What do I even have?

21:10 - What do I need to do right now?

27:06 - What changes and what stays the same?

32:56 - Lean on the support of your wealth manager

36:25 - Get your copy of Decision Decade

37:50 - Closing remarks

The economic story right now can feel confusing. One month the headlines warn about a recession. The next month strong job numbers suggest the opposite. At the same time, interest rates remain elevated, the U.S. dollar has begun to weaken, and investors are trying to figure out how emerging technologies like artificial intelligence might shape the future.

In this episode of Money Made Simple, Mike and Nick Lockwood sit down with Dominic Pappalardo, Chief Multi-Asset Strategist at Morningstar Wealth, to bring clarity to the conversation. Together they break down what the current economic environment actually looks like beneath the headlines and what investors should truly be paying attention to. The discussion explores how interest rates may evolve, why the dollar’s movement matters even for investors who never leave the United States, and whether international markets may finally be positioned for a stronger run.

The conversation also takes a closer look at artificial intelligence and its impact on both markets and the workforce. Is the excitement around AI justified? Where might the real opportunities exist beyond the largest technology companies? And how should investors think about a future where technology could reshape entire industries?

For investors who feel like the economy they see on television does not match the one they experience in their daily lives, this episode aims to provide perspective. Markets change, economic cycles evolve, and new technologies emerge, but understanding the bigger picture can help investors stay focused on what truly matters for their long term financial plans.

Chapters:

0:00 - Introduction

2:14 - Dom's background in investment management

7:50 - Does this really impact you?

16:05 - Savers vs. spenders with interest rates

23:11 - Building out investment portfolios

31:39 - AI's impact on investment management

36:01 - Focusing on the long-term vision

38:45 - Closing remarks

Everyone has heard of a ROTH IRA. Most people have been told they should have one. Very few people truly understand how it fits into their financial life.

In this episode of Money Made Simple, Nick and Mike unpack the bigger picture behind ROTH strategies and why they have become such a central part of retirement conversations. This is not just about checking a box or following generic advice. It is about understanding how taxes, timing, and long-term goals intersect. The conversation explores how different ROTH options can create flexibility, reduce future tax pressure, and potentially reshape the way wealth is transferred to the next generation.

At its core, this episode challenges listeners to think beyond “Do I need a ROTH?” and instead ask better questions. What might my tax world look like later? How do today’s decisions affect my retirement income? How do I position my assets wisely for my family? As with most financial strategies, the answer is not automatic. It depends on your situation. But when used intentionally, a ROTH can be more than just a retirement account. It can be a powerful planning tool.

Chapters:

0:00 - Introduction

1:43 - The history behind ROTH

5:30 - Pre-tax vs. ROTH contributions

10:15 - Breakdown on ROTH 401k and 403b plans

16:18 - What is a ROTH Conversion?

25:00 - Leveraging unused 529 money for ROTH IRA

26:20 - Nick's strategic approach to pre-tax vs. ROTH

29:40 - Mike's approach to pre-tax vs. ROTH

36:15 - ROTH creates flexibility in planning

49:45 - Your free copy of Decision Decade

40:30 - Closing remarks

In this episode of Money Made Simple, Mike and Nick Lockwood explore a reality they see every day while working with employer groups. While retirement plans are often the starting point, the financial questions employees bring to the table go far beyond plan enrollment and contribution limits.

From the employer perspective, Mike shares what consistently shows up in conversations with leadership teams. There is a growing lack of financial literacy, uncertainty around who employees should turn to for guidance, and a desire to support teams without always knowing how. Retirement plans are important, but they are only one part of a much bigger financial picture.

From the employee side, the questions come fast and often feel overwhelming. How much should I contribute. Should I choose pre tax or Roth. How do I balance saving for retirement while trying to buy a home or support my family. Beyond the basics, deeper planning questions surface around trusts, Social Security timing, pension decisions, insurance needs, and ultimately the question everyone asks at some point. When can I retire.

Throughout the conversation, Mike and Nick emphasize a core truth in financial planning. The answer to most of these questions is, it depends. Context matters. Education matters. And having a trusted team to help connect the dots makes all the difference.

Chapters:

0:00 - Introduction

4:02 - What's creating stress among employees?

10:22 - Large employers struggle to properly educate

14:34 - "Americans are confident in retirement, but scared of daily finance"

19:35 - Goal-setting and aligning your financial plan

24:53 - When can I retire?

31:01 - The opportunity that exists for employers

35:22 - Sharing a client story

37:12 - Closing remarks

In this episode of Money Made Simple, Mike and Nick Lockwood tackle one of the most common—and most damaging—challenges people face with their finances: confusion. When there’s no clear direction or understanding, progress stalls. Confusion leads to inaction, inaction leads to messy outcomes, and before long, people lose focus on what truly matters for their families and their future.

The conversation explores why so many individuals feel overwhelmed by financial decisions and why having a coach or teacher is often the missing piece. Mike and Nick discuss how poor experiences—such as being sold products that weren’t fully explained or receiving advice that felt overly complex—can create frustration, distrust, and long-term paralysis. They also address a common refrain they hear from clients: “I don’t understand my advisor.” When conversations move too fast or focus only on investments instead of goals, clarity is lost.

A central theme of the episode is the power of simplicity. While comprehensive financial plans are important, they’re only effective if people can follow through. Mike explains why Oakwood emphasizes breaking plans down into clear, digestible action steps—because a simple plan that gets executed is far more valuable than a complex one that sits on a shelf.

Chapters:

0:00 - Introduction

1:06 - What keeps you up at night?

8:24 - Making sense of your data and developing a plan

14:42 - Inaction typically stems from a lack of a coach

19:35 - "I can't understand my financial advisor"

25:58 - First steps you can take towards financial clarity

29:27 - Have key financial discussions with your spouse

33:00 - Closing remarks