What does it look like to turn a hobby into a thriving business — with no roadmap, no industry model to follow, and a drafty warehouse as your starting point? Melissa Joy, CFP®, sits down with Christy Howden, CEO and co-founder of Wolverine Pickleball, to trace an extraordinary entrepreneurial journey from stay-at-home mom to leader of one of the country’s first pickleball-centric destination facilities.

Christy shares how a 2017 New Year’s resolution sparked a business she never could have predicted, and how she and her business partner bootstrapped their way from rented school gyms to a 38,000 square foot facility that has become a community hub for connection, play, and purpose. Along the way, Melissa Joy, CFP®, weighs in on what financial planners can and cannot say about investing in private businesses and why having a frank conversation with your advisor matters more than the answer you get.

What You’ll Learn

• How Christy and her business partner built Wolverine Pickleball from the ground up with sweat equity, community volunteers, and a minimum viable product mindset
• Why 80% of their investors were women and what it means to make a lifestyle investment that overrides professional financial advice
• How Melissa Joy, CFP®, approaches conversations about investing in small businesses and passion projects
• The funding realities female entrepreneurs face and why the statistics around fundraising make building community capital even more important
• How a second act business can emerge from a life transition and why community is often the renewable energy source behind entrepreneurial endurance
• Practical ways listeners can support small businesses beyond just showing up

Connect with Christy: wolverinepickleball.com

https://www.instagram.com/wolverinepickleball/

https://www.facebook.com/WolverinePickleball/

Third-party rankings and recognition from rating services or publications are no guarantee of future investment success. Working with a highly rated advisor does not ensure that a client or prospective client will experience a higher level of performance or results. These ratings should not be construed as an endorsement of the advisor or by any client, nor are they representative of any one client’s evaluation. Generally, ratings, rankings, and recognition are based on information prepared and submitted by the advisor. This ranking is based on data as of 12/31/2025. The ranking was released on 02/12/2026. Pearl Planning and Melissa Joy did not pay any compensation to be considered for this rating and does not pay an annual fee for marketing usage of the logo. The methodology used to determine The Michigan 50 Companies to Watch award can be found here: Please visit the ranking methodology page for more info.

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

The financial news cycle moves fast, but the fundamentals of investing have not changed. Melissa Joy, CFP® sits down with Ben Carlson, Director of Institutional Asset Management at Ritholtz Wealth Management and author of five books including his latest, Risk and Reward, to explore what history actually teaches us about markets, human nature, and the psychology behind smart long-term investing. Ben brings equal parts data and storytelling to make the case that understanding the past is one of the most underrated tools an investor can have.

From the inflationary spiral of the 1970s to lost decades and the dot-com aftermath, Ben and Melissa walk through the market cycles that shaped today's investing environment and what those periods reveal about our own tendencies as investors. They also dig into the coming wave of wealth transfer, why women will increasingly control the bulk of financial assets, and why the financial advice industry is not yet ready for it.

What You'll Learn

• Why studying financial history matters and what it reveals about the range of possible outcomes
• How inflation in the 1970s shaped investor psychology in ways that still resonate today
• What the lost decade of 2000 to 2010 teaches about diversification and why that lesson keeps getting forgotten
• Why simplicity in a financial plan beats complexity almost every time
• How to build a portfolio durable enough to survive a wide range of outcomes without requiring you to predict the future
• Why preparation is more valuable than prediction when it comes to investing
• What the great wealth transfer means for women and why the financial advice industry needs to catch up
• How human nature is the one investing variable that never changes across market cycles
• What Ben's list of 20 investing beliefs reveals about discipline, self-awareness, and behavioral finance
• Why the best financial plan is the one you can actually stick with through difficult markets

About Ben Carlson

Ben Carlson is the Director of Institutional Asset Management at Ritholtz Wealth Management and the author of five books on investing and personal finance, including his latest, Risk and Reward. He is the creator of the blog Wealth of Common Sense and co-host of the Animal Spirits podcast.

Book: Risk and Reward

Blog: awealthofcommonsense.com

Podcast: Animal Spirits

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Nearly a quarter of Americans have no traditional next of kin, yet the financial planning industry has long operated as if everyone will eventually have children. Melissa Joy, CFP® sits down with Maddy Roche, co-host of the Child Free Life by Design Podcast and Chief Growth Officer of Partnerships for Child Free Trust, to talk about what changes and what becomes possible when you are building a financial life without kids.

Maddy brings both personal and professional perspective to the conversation. As someone who is child free by choice, she shares how a financial plan created specifically for her shifted her entire mindset around spending, legacy, and the concept of dying with zero. She and Melissa dig into why estate planning has been so hard for this demographic to complete, why that needs to change, and how Child Free Trust is filling a gap that trust companies and traditional advisors have largely left open.

What You’ll Learn

• Why child free people represent a distinct and underserved financial planning demographic
• How planning assumptions tied to children create blind spots for advisors working with this group
• Why long-term care insurance matters more than life insurance for most child free people
• What the die with zero philosophy means and how it gives child free people a financial permission slip to spend and experience more
• Why upwards of 70 percent of child free people do not have a legally binding estate plan in place
• How to reframe estate planning as contingency planning and why it matters long before death
• What roles are required in a complete estate plan and why they are especially hard to fill without children
• How Child Free Trust serves as a professional fiduciary in the roles of medical and financial power of attorney, executor, and trustee
• Why hourly billing rather than assets under management makes professional fiduciary services more accessible
• How the Child Free Trust care document captures everything from pet care plans to end of life wishes

Estate Planning and Membership: ChildFreeTrust.com

Thought Leadership, Podcast, and Community: ChildFreeInsights.com

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

A new type of savings account has entered the conversation, and if you have young children, you need to know about it. Melissa Joy, CFP® sits down with Ann Garcia, CFP®, returning guest, college funding expert, and author of How to Pay for College, to break down the newly created Trump accounts. Also known as 530A accounts, these IRA-style vehicles are generating a lot of buzz, and Ann helps separate the hype from the reality so families can make smart decisions about whether and how to use them.

The conversation goes beyond the new accounts. Melissa and Ann also respond to a widely shared Wall Street Journal article about a financial planning expert who is skipping 529s for his own kids, and explain why that strategy works for a very small slice of the population but could leave most families short. They close with practical wisdom on how to talk to your kids about money at every age, and why starting simple is always better than waiting until you have the perfect lesson plan.

What You’ll Learn

• What Trump accounts (530A accounts) are and how they work
• How to open an account and claim the free government funding your child may be entitled to
• Why Trump accounts are generally not the best vehicle for college savings, and what to use instead
• How the kiddie tax affects withdrawals and why it matters for your planning
• The difference between how Trump accounts and 529s are treated on the FAFSA
• The Wall Street Journal article making the case to skip 529s, and why Ann and Melissa push back
• Why the 529 remains one of the most flexible and tax-efficient tools for college savings
• When and how to help your young adult children get their first Roth IRA open
• Why automating your financial life is the antidote to always being in triage mode

Connect with Ann Garcia, CFP®

Website: howtopayforcollege.com

Book: How to Pay for College

The Mather Group: themathergroup.com

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

What would it look like to stop working at 50? Or to step away from a high-powered career and spend your time doing something that lights you up instead?

For many women, this is not just a dream. With the right plan, it is a very real option. Melissa Joy, CFP® sits down with Bridget Grimes, founder of Wealth Choice and co-founder of Equita Financial Network, to talk about what retiring in your 50s or 60s actually requires, from knowing your cost of living to healthcare coverage, Roth conversions, and finding purpose on the other side.

Bridget is a financial planner, CFP Board Ambassador, and fierce advocate for women and women-led financial firms. She works with breadwinner women every day who are building toward financial independence, and in this conversation she pulls back the curtain on the planning conversations that make early retirement possible.

What You’ll Learn

• What Coast FIRE is and why it resonates with so many high-achieving women
• Why knowing your actual cost of living is one of the most important retirement planning inputs
• How a stair-step retirement, with part-time or passion work, can meaningfully improve your financial picture
• Why healthcare is the biggest wild card for anyone retiring before Medicare eligibility at 65
• How to think about COBRA, the ACA exchange, and HSAs as part of your early retirement plan
• Why having multiple account types, taxable, pre-tax, and Roth, gives you flexibility and tax options
• How Roth conversions work as a multi-year strategy and why doing them all at once can backfire
• What the Rule of 55 means for 401k access and how it differs from IRA rules
• Why rebalancing your investment allocation matters when you stop earning and start drawing
• How to give yourself permission to think about what you actually want your life to look like
• Why early retirement is as much a social and emotional transition as it is a financial one
• What to look for in a financial advisor if you are planning to retire earlier than traditional ages

Connect with Bridget Grimes

Website: wealthchoice.com

LinkedIn: linkedin.com/in/bridget-venus-grimes-cfp

Facebook: facebook.com/wealthchoice

Instagram: wealthchoice_

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Most people know they need an estate plan. Far fewer actually have one, and even fewer have had the conversations with their families that make that plan meaningful. Melissa Joy, CFP® sits down with Nicole Adkison, estate planning attorney and wealth strategist, to talk about what thoughtful estate planning really involves, from the foundational documents to the deeper family conversations that give those documents their purpose.

Nicole works with families and their advisors to design forward-looking plans that protect assets and preserve family harmony. In this conversation, she brings both the technical framework and the human heart of estate planning into focus, including why the why behind your decisions matters just as much as the what.

What You'll Learn

• What estate planning actually is and why a will alone is rarely enough
• Why probate is a process worth avoiding and how a revocable trust helps you do that
• What powers of attorney and healthcare directives do and what happens without them
• Why complexity in an estate plan does not just mean complex assets
• The most common source of family conflict after a death and how to address it before you are gone
• Why being named trustee is rarely the honor it is treated as and how to choose the right person for the job
• How to have age-appropriate conversations about money and legacy, even with young children
• What purpose statements inside your estate plan can do that the documents alone cannot
• Why unequal distributions are sometimes the fairest choice and how to explain them to your family
• How dynasty trusts work as a family bank rather than a windfall and why that matters for long-term legacy
• Why your estate plan should be reviewed regularly and what a good advisor relationship looks like over time
• The role your financial advisor and estate planning attorney should play together

Connect with Nicole Adkison:

Website: adkisonlaw.com

LinkindIn: https://www.linkedin.com/in/nicole-adkison-7236408/

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

No one expects to get in an accident. But when you do, and when injuries are involved, navigating the insurance system and legal landscape can feel overwhelming. Melissa Joy, CFP® sits down with Megan Burns, founder of Mirador Law and personal injury trial lawyer, to pull back the curtain on what actually happens after an accident and how to protect yourself before one ever occurs.

Megan brings both professional expertise and personal experience to this conversation, having been seriously injured in a bike accident in her early twenties. From understanding your auto insurance coverage to knowing when you need a lawyer and when you do not, this episode gives listeners a practical, honest roadmap for one of the most financially and emotionally complex situations a person can face.

What You'll Learn

• Why your insurance policy is a financial hedge and how to treat it like one
• The difference between fault states and no fault states and what that means for your coverage
• Why uninsured and underinsured motorist coverage is one of the most important protections you can have
• How Michigan's 2020 no fault law changes affect what you are actually covered for
• Why disability insurance may be as important or more important than life insurance
• When you absolutely need a personal injury attorney and when you do not
• How to find a quality personal injury lawyer and the red flags to avoid
• Why hiring a trial lawyer specifically makes a significant difference in outcomes
• What to expect from the legal process after signing with an attorney
• How umbrella liability insurance works and why it matters for protecting your assets

Connect with Megan: Website: www.miradorlaw.com

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...

Most people think investing means picking the right stocks and getting rich. But according to Cullen Roche, founder and CIO of Discipline Funds and author of Your Perfect Portfolio, that mindset is one of the most costly mistakes investors make. Melissa Joy, CFP® sits down with Cullen to unpack what investing actually is, why time horizons matter more than almost anything else, and how to build a portfolio you can stay loyal to when markets get uncomfortable.

From the three fund portfolio to dividend strategies to the growing world of high fee distribution ETFs, Cullen breaks down a wide range of investment approaches with honesty and clarity. This is not a conversation about hot stocks or market timing. It is a conversation about building something that actually works for your life.

What You'll Learn

• Why investing is better understood as a reallocation of savings than a path to getting rich quick
• How thinking about time horizons can transform the way you build and manage a portfolio
• Why planning toward averages, including average life expectancy, can set investors up to fail
• What the three fund portfolio is, why it works, and where it may fall short for some investors
• The pros and cons of dividend focused portfolios and what investors often misunderstand about them
• Why distribution ETFs are not the income generating bond alternatives they are often marketed as
• How an asset liability matching approach can help investors align their money with real life goals
• Why managing your own behavior is the most critical component of long term investment success
• What the financial media gets wrong and how to tune out the noise without missing what matters

Connect with Cullen:

Website: https://disciplinefunds.com

LinkedIn: https://www.linkedin.com/in/cullenroche

X: https://x.com/cullenroche

The previous presentation by PEARL PLANNING was intended for general information purposes only. No portion of the presentation serves as the receipt of, or as a substitute for, personalized investment advice from PEARL PLANNING or any other investment professional of your choosing. Different types of investments involve varying degrees of risk, and it should not be assumed that future performance of any specific investment or investment strategy, or any non-investment related or planning services, discussion or content, will be profitable, be suitable for your portfolio or individual situation, or prove successful. Neither PEARL PLANNING’s investment adviser registration status, nor any amount of prior experience or success, should be construed that a certain level of results or satisfaction will be achieved if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. PEARL PLANNING is neither a law firm nor accounting firm, and no portion of its services should be construed as legal or accounting advice. No portion of the video content should be construed by a client or prospective client as a guarantee that he/she will experience a certain level of results if PEARL PLANNING is engaged, or continues to be engaged, to provide investment advisory services. A copy of PEARL PLANNING’s current written disclosure Brochure discussing our advisory services and fees is available upon request or at https...