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...