Tag: Retirement Life
Important Tax Mistakes to Avoid {That CPAs Wish You Knew} (Ep.22)

Important Tax Mistakes to Avoid {That CPAs Wish You Knew} (Ep.22)

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In this episode, Michelle Gessner sits down with Madison Ross, co-founder of Ross & Connor LLP, a CPA firm based in Fort Worth, Texas. Together, they dive into why proactive tax planning and working with professionals is essential to avoid costly mistakes and optimize tax strategies.

Madison, an expert in small business, real estate, and individual taxation, shares common tax pitfalls to avoid, including the main problem with gifting property during your lifetime to loved ones, why titling real estate to an S-corporation may not be a good idea for business owners, tax essentials for cryptocurrency owners and navigating Roth conversions. Michelle and Madison also explain how avoiding unintended consequences like Medicare surcharges and leveraging the right software can make tax planning more efficient and effective.

Take note as Michelle and Madison cover: 

  • Gifting property during one’s lifetime may lead to high tax liabilities due to the loss of a step-up in basis
  • Roth conversions require careful planning to avoid higher tax brackets and unintended consequences 
  • Risks of using an S-Corp for real estate for business owners Consulting  professionals can help prevent costly tax mistakes
  • And more

Connect with Madison Ross:

Connect with Michelle: 

About Our Guest: 

Madison Ross is a Tax Partner and co-founder of Ross and Connor LLP. His focus is on Small Business, Real Estate, and Individual taxation. The firm incorporates tax planning strategies, which provide clients with a roadmap for tax savings and wealth building. Madison is a member of the Main Street Business Certified Tax Advisory Network, which consists of hundreds of CPAs, Enrolled Agents, and Lawyers from across the country who meet weekly to discuss up-to-date tax strategies. He received a certification in Cryptocurrency Taxation from Main Street Business in 2022. Madison is licensed as a CPA in Texas and New Mexico and is a member of the AICPA.

About Michelle Gessner: 

As a CERTIFIED FINANCIAL PLANNER™ professional, Michelle is passionate about building a life plan for her clients and helping them see that they have choices, which often comes to them as a pleasant surprise. She is an independent thinker and a huge advocate of her clients’ interests. Her greatest joy is working to do what is right for them and be their voice.

Michelle has a B.S. in Finance from the University of Colorado, Boulder, and an M.S. in Management from Boston University, Brussels. Growing up in Montana and moving to Colorado for college, she took out student loans and worked her way through all four years. After graduating in 1987 with honors, she accepted a job at Shell Oil in Houston, and worked her way up the corporate ladder to a management position before leaving in 1992 for Brussels, Belgium, where she lived for 4 years. In Brussels, she learned about different cultures and basic conversational French as well as pursuing and earning a graduate degree in management. 

As a CERTIFIED FINANCIAL PLANNER™ professional,  she is held to the highest standards set forth in the industry. She surrounds herself with a back office of experts in tax and investment research so that her clients have the best of both worlds – the resources of a large firm with the caring, dedication, and personal service of a small firm.
Will Social Security Run Out of Money and Optimizing Your Benefits (Ep. 21)

Will Social Security Run Out of Money and Optimizing Your Benefits (Ep. 21)

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If you want to make the most of your Social Security benefits, this episode is a must-listen!

Join Michelle Gessner as she breaks down the facts behind the Social Security debate—will it run out, or is it just a myth? Plus, Michelle shares essential strategies whether you’re married, divorced, or a surviving spouse, to help you secure every dollar you deserve.

Don’t miss out! Listen now and empower yourself with Michelle’s expert guidance to navigate the complexities of Social Security with confidence.

Resources:

Connect with Michelle Gessner: 

About Michelle Gessner: 

As a CERTIFIED FINANCIAL PLANNER™ professional, Michelle is passionate about building a life plan for her clients and helping them see that they have choices, which often comes to them as a pleasant surprise. She is an independent thinker and a huge advocate of her client’s interests. Her greatest joy is working to do what is right for them and be their voice.

Michelle has a B.S. in Finance from the University of Colorado, Boulder, and an M.S. in Management from Boston University, Brussels. Growing up in Montana and moving to Colorado for college, she took out student loans and worked her way through all four years. After graduating in 1987 with honors, she accepted a job at Shell Oil in Houston, and worked her way up the corporate ladder to a management position before leaving in 1992 for Brussels, Belgium, where she lived for 4 years. In Brussels, she learned about different cultures and basic conversational French as well as pursuing and earning a graduate degree in management. 

As a CERTIFIED FINANCIAL PLANNER™ professional,  she is held to the highest standards set forth in the industry. She surrounds herself with a back office of experts in tax and investment research so that her clients have the best of both worlds – the resources of a large firm with the caring, dedication, and personal service of a small firm. 
Behind The Curtain: What You Need To Know About Annuities (Ep.20)

Behind The Curtain: What You Need To Know About Annuities (Ep.20)

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Are annuities a smart addition to your retirement portfolio? 

Join Michelle as she breaks down different types of annuities—fixed, fixed index, and variable annuities—explaining how they can fit into a comprehensive financial plan. Understand the tax advantages and risks associated with each type, and learn why annuities might not be as bad as you think, if used in moderation and understood. 

Featuring practical examples, this episode aims to educate and empower you to make informed decisions about your financial future.

Key episode discussion points include:

  • The difference between fixed annuities and fixed index annuities
  • How annuities can offer financial security without market risk
  • Variable Annuities: Market-based investments with potential for growth but accompanied by higher fees
  • Deferred and Immediate Income Annuities: Lump-sum vehicles  that convert your money  into an income stream that you cannot outlive 

Resources:

Connect with Michelle Gessner: 

About Michelle Gessner: 

As a CERTIFIED FINANCIAL PLANNER™ professional, Michelle is passionate about building a life plan for her clients and helping them see that they have choices, which often comes to them as a pleasant surprise. She is an independent thinker and a huge advocate of her clients’ interests. Her greatest joy is working to do what is right for them and be their voice.

Michelle has a B.S. in Finance from the University of Colorado, Boulder, and an M.S. in Management from Boston University, Brussels. Growing up in Montana and moving to Colorado for college, she took out student loans and worked her way through all four years. After graduating in 1987 with honors, she accepted a job at Shell Oil in Houston, and worked her way up the corporate ladder to a management position before leaving in 1992 for Brussels, Belgium, where she lived for 4 years. In Brussels, she learned about different cultures and basic conversational French as well as pursuing and earning a graduate degree in management. 

As a CERTIFIED FINANCIAL PLANNER™ professional,  she is held to the highest standards set forth in the industry. She surrounds herself with a back office of experts in tax and investment research so that her clients have the best of both worlds – the resources of a large firm with the caring, dedication, and personal service of a small firm. 
Retirement Checklist: 6 Questions To Ask Yourself (Ep.19)

Retirement Checklist: 6 Questions To Ask Yourself (Ep.19)

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Are you ready for retirement? Let’s find out! 

On today’s show, Michelle Gessner, CFP® shares a checklist that includes six questions to ask and answer before you decide to hang up your career hat.

With her co-host, Michelle discusses the necessity of professional help with investments, the decision to retain money in an employer’s retirement plan, and the importance of stress-testing your retirement strategy.

She also shares some key insights on finding purpose in retirement, ensuring both financial security and personal fulfillment. 

By listening to this episode, you will:

  • Better understand why professional investment advice can lead to greater success and diversification
  • Learn the pros and cons of keeping your retirement funds in your employer’s plan versus rolling them over
  • Determine if you are getting the tax planning you need
  • Discover how to stress-test your retirement plan against unexpected financial changes and ensure your assets are protected
  • Gain valuable insights into finding purpose and happiness in retirement, beyond the financial aspects
  • And more

Resources:

Connect with Michelle Gessner: 

About Michelle Gessner: 

As a CERTIFIED FINANCIAL PLANNER™ professional, Michelle is passionate about building a life plan for her clients and helping them see that they have choices, which often comes to them as a pleasant surprise. She is an independent thinker and a huge advocate of her client’s interests. Her greatest joy is working to do what is right for them and be their voice.

Michelle has a B.S. in Finance from the University of Colorado, Boulder, and an M.S. in Management from Boston University, Brussels. Growing up in Montana and moving to Colorado for college, she took out student loans and worked her way through all four years. After graduating in 1987 with honors, she accepted a job at Shell Oil in Houston and worked her way up the corporate ladder to a management position before leaving in 1992 for Brussels, Belgium, where she lived for 4 years. In Brussels, she learned about different cultures and basic conversational French as well as pursuing and earning a graduate degree in management. 

As a CERTIFIED FINANCIAL PLANNER™ professional,  she is held to the highest standards set forth in the industry. She surrounds herself with a back office of experts in tax and investment research so that her clients have the best of both worlds – the resources of a large firm with the caring, dedication, and personal service of a small firm. 
Long-Term Disability Insurance: What You Don’t Know Can Hurt You (Ep.18)

Long-Term Disability Insurance: What You Don’t Know Can Hurt You (Ep.18)

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Are you undervaluing the importance of long-term disability insurance in your financial plan?

This episode reveals the common myths and misunderstandings that could cost you and your loved ones dearly. Michelle dives into why even retirees need to grasp the nuances of disability insurance policies and how overlooking the benefits could expose gaps in your financial safety net.

Discussion points include:

  • How misconceptions around long-term disability insurance often lead to inadequate coverage
  • Understanding the fine print of your policy, including the monthly cap on benefits
  • How locking in coverage when you’re young and healthy helps ensure lower premiums and protection against future health issues.
  • The leading causes of long-term disability claims
  • And more

Connect with Michelle: 

About Michelle Gessner: 

As a CERTIFIED FINANCIAL PLANNER™ professional, Michelle is passionate about building a life plan for her clients and helping them see that they have choices, which often comes to them as a pleasant surprise. She is an independent thinker and a huge advocate of her clients’ interests. Her greatest joy is working to do what is right for them and be their voice.

Michelle has a B.S. in Finance from the University of Colorado, Boulder, and an M.S. in Management from Boston University, Brussels. Growing up in Montana and moving to Colorado for college, she took out student loans and worked her way through all four years. After graduating in 1987 with honors, she accepted a job at Shell Oil in Houston, and worked her way up the corporate ladder to a management position before leaving in 1992 for Brussels, Belgium, where she lived for 4 years. In Brussels, she learned about different cultures and basic conversational French as well as pursuing and earning a graduate degree in management. 

As a CERTIFIED FINANCIAL PLANNER™ professional,  she is held to the highest standards set forth in the industry. She surrounds herself with a back office of experts in tax and investment research so that her clients have the best of both worlds – the resources of a large firm with the caring, dedication, and personal service of a small firm. 
Turning Your Hobby Into a Paid Passion with Lee Rathbun (Ep.16)

Turning Your Hobby Into a Paid Passion with Lee Rathbun (Ep.16)

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“Find a job you’ll love and you’ll never work a day in your life.”’

But how?

Michelle Gessner is joined by special guest Lee Rathbun, a part-time sports official who shares his journey of turning his hobby into a paid gig. They explore the theme of “What are you going to do in retirement,” emphasizing the importance of not just planning for financial security but also planning for a fulfilling retirement lifestyle.

Lee Rathbun shares his experience of transitioning from baseball to football and lacrosse officiating, highlighting the physical activity, competition, and enjoyment he derives from his role as a referee. 

This installment of Retire To A Life You Love® discusses:

  • How Lee turned a hobby into paid opportunities
  • The benefits of doing something you like both for your physical and mental well-being
  • Dealing with pressure on and off the field
  • The shortage of referees & why you should consider becoming a sports official if you have a passion for sports
  • And more

Resources:

Connect with Michelle Gessner: 

Connect with Lee Rathbun:

About Lee Rathbun:

Lee Rathbun has lived in Houston since 2012 but is originally from Gaithersburg, Maryland. He has a bachelor’s degree in business with a master’s in telecommunications, both from the University of Maryland, and spent 9 years serving in the US Navy.  With a career in the transportation industry in logistics, Lee spends a lot of his free time as a high school football and lacrosse referee across metro Houston and in Pennsylvania where he lived before arriving in Houston. He’s also been found participating in various mud runs like the Spartan race. Lee has been a referee in his free time since 2005, about 19 years.  He is assigned anywhere between 2-4 games per week and sometimes more.  

FEATURE
Medicare: A Comprehensive Guide with Joanne Giardini Russell (Ep.15)

Medicare: A Comprehensive Guide with Joanne Giardini Russell (Ep.15)

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After the successful release of “Understanding Medicare: A Guide for Beginners,” Michelle was prompted to ask Joanne Giardini Russell back to the show to provide a deeper look into Medicare.

Let’s gain further knowledge about how to make informed decisions regarding your healthcare and insurance options as Michelle and Joanne discuss: 

  • Recommendations to prepare for Medicare six months before eligibility 
  • Seek professional guidance to avoid common enrollment mistakes
  • The importance of annually reviewing your drug plans
  • Growing concerns surrounding predatory marketing/scams 
  • The Inflation Reduction Act and its impact on pharmaceuticals 
  • And more

Resources:

Connect with Michelle Gessner: 

Connect with Joanne Giardini Russell:

About Joanne Giardini-Russell:

Joanne Giardini-Russell is the owner of Giardini Medicare, an independent agency that provides Medicare products to the public. She and her team of Medicare nerds at Giardini Medicare specialize in the “transition” to the Medicare system. Do you need Medicare? If so, how do you get there in a stress-free and logical fashion? Having spent years in the financial and insurance industries, Joanne recognized an enormous and unfilled niche. Namely, the lack of quality education and assistance in “best practices” in getting yourself into the Medicare system.

She and her team of agents have grown a firm that can help assess the “Do I need Medicare,  how do I get it, how does it work” questions and more. They assist in the transition from the workplace era and into the Medicare years and enroll people in the proper Medicare products. 

Joanne routinely leads Medicare sessions for financial advisors, CPAs, Credit Unions, and the public. Additionally, she often writes Medicare content for publications and websites such as  Advisor Perspectives, SixtyandMe.com, and InsuranceNews.Net. She and Cameron Giardini produce the “Transition to Medicare” Podcast. , He produces the company’s YouTube channel while she handles TikTok. The company website is https://gmedicareteam.com/ 

Joanne resides in Michigan with her husband, Jeff. Three of her adult children work with her at Giardini Medicare; creating what they affectionately refer to as the “First Family of Medicare”.  

FEATURE
Retiring Abroad: How Glenda Cole is Living Her Storybook Life in Portugal (Ep.14)

Retiring Abroad: How Glenda Cole is Living Her Storybook Life in Portugal (Ep.14)

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A lot of us spend time planning for our retirement from a financial perspective, which I will never tell you is a bad thing. However, how much thought have you given to HOW you will spend your retirement?

Everyone deserves to Retire to a Life You Love®, and today’s guest has done just that! Glenda Cole shares what it’s like living her storybook life in Portugal including details surrounding what led her to choose to leave the US. She gives insight and helpful tips about living abroad including the relaxed lifestyle, and affordable cost of living.

Gain insight into living abroad as Glenda shares:

  • Her journey of retiring to Portugal and what led her to this “leap of faith” decision
  • The perks and drawbacks of living abroad including tax implications
  • How she maintains her relationships in the United States
  • A day in the life of a retiree in Portugal (Yes, it’s as amazing as it sounds!)
  • And more

Resources:

Connect with Michelle Gessner: 

Connect with Glenda Cole: 

About Glenda Cole: 

Glenda Cole’s career culminated as the Vice President of Marketing and Sponsorship for a U.S. developer of luxury shopping malls.  She managed a team of just under 100 professionals and a budget of over $60 million.  She was responsible for the marketing strategy for some of the most prestigious malls in the U.S., including upscale properties in most of the major markets in America.  She was awarded the prestigious International Webby Award for internet excellence and two Silver Caddys for copywriting.  

Glenda was the company spokesperson for marketing and was featured in television, radio, internet, and print interviews.  She created partnerships with many brands, including Disney’s Frozen, Fox Studios Ice Age, the Broadway show Wicked, Microsoft, and American Express.  Glenda is most proud of being recognized as the “most inspirational executive” in the company.  Since retiring to Portugal, Glenda has written a column in the Portugal Resident and has been the Social Secretary for the Casa social club.  She currently writes, creates internet content, and appears as a speaker for International Living magazine.  

FEATURE
Top Takeaways from 2023 (Ep.13)

Top Takeaways from 2023 (Ep.13)

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A new year provides opportunities for growth and self-improvement, and this extends to your finances too! 

But before we look too far ahead, let’s revisit a few 2023 episodes of Retire To A Life You Love® for the top takeaways that you can carry into the new year.

Gain insight as Michelle highlights practical reminders and nuggets of financial wisdom like:

  • The value of understanding and implementing tax strategies for your retirement
  • Tips for your Roth 401(k), Roth 403(b) including converting pre-tax money  
  • Benefits of a Qualified Charitable Distribution (QCD) strategy
  • Key issues for estate planning for yourself but also your aging parents

Resources:

Connect with Michelle Gessner:

About Michelle Gessner: 

As a CERTIFIED FINANCIAL PLANNER™ professional, Michelle is passionate about building a life plan for her clients and helping them see that they have choices, which often comes to them as a pleasant surprise. She is an independent thinker and a huge advocate of her client’s interests. Her greatest joy is working to do what is right for them and be their voice.

Michelle has a B.S. in Finance from the University of Colorado, Boulder, and an M.S. in Management from Boston University, Brussels. Growing up in Montana and moving to Colorado for college, she took out student loans and worked her way through all four years. After graduating in 1987 with honors, she accepted a job at Shell Oil in Houston and worked her way up the corporate ladder to a management position before leaving in 1992 for Brussels, Belgium, where she lived for 4 years. In Brussels, she learned about different cultures and basic conversational French as well as pursuing and earning a graduate degree in management. 

As a CERTIFIED FINANCIAL PLANNER™ professional,  she is held to the highest standards set forth in the industry. She surrounds herself with a back office of experts in tax and investment research so that her clients have the best of both worlds – the resources of a large firm with the caring, dedication, and personal service of a small firm.