Welcome back to Don’t Retire… Graduate! In today’s episode, we’re exploring one of the most critical and overlooked aspects of retirement: transitioning your identity, purpose, and fulfillment as you move into the next chapter of life. Joining me for this conversation is Jack Calhoun, the founder and president of Encore Career Lab. Jack isn’t just a seasoned entrepreneur after leading a wealth management firm from $50 million to over $1.5 billion in assets and selling the business in his early 50s, Jack faced the emotional and identity challenges that often come after a primary career ends. Through his own post-career journey of “wondering and wandering,” Jack discovered firsthand that financial planning alone is never enough.

Jack and I dove into the parallels between our journeys, both as liberal arts majors and as people who built companies, stepped away from the top job, and then wondered “what’s next?” Together, we unwrapped the deeply personal and often daunting process of redefining yourself and finding meaning once the “what do you do?” The question no longer has a simple answer. Jack candidly shared the psychological hurdles many face upon retirement, especially for high achievers who tied their identity so closely to professional success.

We discuss the pitfalls of thinking retirement is only about “doing the math,” and the dangers of the so-called Striver’s Curse where career-driven people lose their sense of purpose and can become rudderless once the striving ends. Jack’s experiences and research led him to develop Encore Career Lab, a program designed to help successful professionals regain their “rudder,” starting with “why,” then the “what,” and finally, the “how.” We explore his three-phase approach to post-career transformation, the importance of generativity (the drive to give back and pass on wisdom), and why building a roadmap for fulfillment, not just finances, is vital in modern retirement.

5 Key Takeaways:

1. Identity Challenges After Retirement: Jack illustrated how even strong, career-driven individuals can underestimate the existential impact of leaving their professional roles, discovering that so much of our identity is tied to what we do and contribute.
2. Purpose Is More Important Than Leisure: We debunked the myth that endless recreation leads to fulfillment, revealing that humans are wired for purpose, meaning, and generativity and that’s what produces happiness beyond financial freedom.
3. Start with Why: Jack’s work with Encore Career Lab emphasizes discovering your “why” before choosing what you’ll do and how you’ll do it post-career; clarity on purpose leads to choices that align with your values and lead to true fulfillment.
4. The Risk of Losing Your Rudder: Without intentional planning, retirees often become overwhelmed, dabble without direction, or feel paralyzed by too many options; a structured process is vital to avoid feeling rudderless or self-conscious about your next steps.
5. Generativity as the Common Thread: As people mature, the drive to give back and share accumulated wisdom becomes a universal impulse. Jack observed that everyone drawn to his program feels a compulsion to help others and leave a legacy making mentorship, teaching, and service recurring encore themes.

Join us for this inspiring conversation on redefining the very nature of retirement from a finish line to a commencement. If you or someone you know is approaching a new phase of life and seeking more than just financial security, this episode will open your eyes to the possibilities of true graduation. Don’t forget to subscribe, rate, and share this episode with anyone eager for a purpose-filled future!

Welcome back to Don’t Retire… Graduate! In this inspiring episode, we’re exploring how to break free from financial overwhelm—especially for those whose brains are wired a little differently. Joining me today is Andrea Ewalefo, founder and CEO of Modern Lady Vibes. Andrea is dedicated to empowering neurodivergent women by helping them harness their unique strengths to build real wealth with her signature 5-step VIBES framework. With her background as a JD, MBA, and former financial advisor, Andrea brings both professional expertise and personal experience to the conversation. In today’s discussion, Andrea and I dove into the world of neurodivergence—what it means, how it manifests, and why traditional financial advice often doesn’t resonate for people whose executive function operates outside typical norms. Andrea shared her story of being featured in CNBC, her passion for helping women (and men!) who’ve been overlooked by conventional financial education, and the challenges that come with both neurodivergence and societal expectations, especially for women. We explored Andrea’s VIBES framework, which stands for Vision, Intention, Baseline, Engineer, and Streamline. Andrea explained how automating financial habits, removing unnecessary decision-making, and reducing shame around money management can open doors to financial independence—even if staying “consistent” has always felt impossible. We discussed how different life experiences—gender, late diagnosis, social expectations—impact financial behaviors, and how anyone, regardless of diagnosis, can benefit from a shift away from shame and toward practical, sustainable systems. 5 Key Takeaways:

1. Redefining Neurodivergence in Finance:Neurodivergence includes ADHD, autism, dyslexia, and other ways of thinking outside the “typical” brain. Traditional personal finance guidance usually isn’t built for these experiences—so it’s time for new, more compassionate systems.
2. The VIBES Framework:Andrea’s 5-step approach—Vision, Intention, Baseline, Engineer, Streamline—centers self-acceptance, automation, and upfront decision-making to minimize overwhelm and maximize financial empowerment.
3. Eliminating Shame and Embracing Automation:Regular budgeting advice often causes guilt and decision fatigue. By automating savings, bill payments, and allocations for fun money, you can break negative cycles and focus energy where it matters.
4. Societal & Gender Differences:Women are often diagnosed later with neurodivergence and taught to overcompensate—masking symptoms and fueling perfectionism. Andrea’s approach emphasizes why it’s crucial to address these unique pressures.
5. Community and Support:You don’t have to be diagnosed as neurodivergent—or even a woman—to find value in Modern Lady Vibes. If traditional advice leaves you overwhelmed, Andrea’s inclusive, strengths-focused community and resources might be a game-changer.

Join us as we challenge outdated financial norms and encourage everyone to create a more sustainable—and joyful—path to financial freedom! Don’t forget to subscribe, rate, and share this episode with friends, family, or anyone who’s felt lost trying to fit typical financial advice into their unique life. [embed]https://youtu.be/nTMifPiZQQU[/embed]

Mentioned in this episode:

Don't Retire... Graduate! is presented by BFG Financial Advisors

BFG Financial Advisors helps individuals and families design a financial future that supports the life they want to live—not just the numbers on a page. From retirement income and tax strategies to legacy planning and investment management, our team builds personalized plans designed for clarity and confidence. Ready to take the next step? Visit bfgfa.com to schedule a free consultation and start planning your next chapter.

BFG Financial Advisors

1. Growth Beyond the Textbook: Kobe Bolanos emphasizes that real financial advising isn’t just about technical knowledge; it’s about understanding clients’ emotions and unique situations—skills you only build through experience.
2. Importance of Emotional Intelligence: Emotional intelligence is crucial, especially when guiding clients through transitions, losses, or fears. Effective advisors translate technical concepts into language clients can relate to, tailoring advice on a client-by-client basis.
3. Early Advocacy for Estate Planning: Kobe Bolanos is committed to bringing estate planning awareness to younger generations, having witnessed firsthand the financial and emotional impact of being prepared—or not.
4. Building Young Professional Networks: By connecting with the Young Lawyers Group and leading professional organizations, Kobe Bolanos is fostering relationships that will shape the future of the industry, proving the value of starting early in building a professional community.
5. Learning from Mistakes: Neither career nor personal growth happens without a few stumbles. Kobe Bolanos’s ability to laugh at himself, learn, and roll with mistakes demonstrates resilience—an invaluable trait for any professional.

In today’s Office Hours, Eric answers Ben's question: "Is it better to pay in cash for daily purchases or use a credit card?”

This answer can vary based on your spending habits, so Eric is here to outline who may benefit from each option.

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome back to Don’t Retire… Graduate! With Veterans Day coming up, we have a very special guest to talk about how she uses her own experience with finance and military service to serve the Veteran community.

Dr. Ann James is a veteran of the U.S. Air Force, a Certified Financial Coach, and the CEO of Financial Freedom Battle Buddies, and is on a mission to help fellow veterans transform their financial well-being. 

We thank Dr. James and all her fellow veterans for their service and are proud to share her story with you today. 

In this episode we’ll talk about:

• Dr. Ann James’s story of military service, single parenthood of a child of special needs, and how she found her passion for personal finance.

• The importance of financial planning as a parent of a child with special needs.

• The B.A.T.T.L.E. plan for financial freedom.

• The loss of financial security many military families feel when they leave the service.

• Necessary versus unnecessary debt.

• The unique challenges that are faced by the military community and the challenges that come with working with the community.

• Advice for military members who are still serving for transitioning out of the military.

• What comes next and what Dr. James wants to be when she grows up.

About Dr. Ann James

Dr. Antoinette (Ann) James began her career as an enlisted member in the U.S. Air Force. Over her military career, she held numerous positions which included personnel administration and financial management. Upon earning her commission, she was responsible for executing multi-million-dollar operating budgets within the U.S. and overseas. After 21 years of proud service, she retired and went on to earn her Doctorate of Education. 

 Currently, as a Certified Financial Coach and CEO of Financial Freedom Battle Buddies, Dr. Ann is on a mission to educate and equip military veterans on how to transform their financial well-being using her B.A.T.T.L.E method. She’s been featured and cited on several platforms such as USA Today and the Penny Hoarder. In her free time, she enjoys traveling, reading and spending time with family and friends. 

www.drannjames.com

Visit dontretiregraduate.com for a full transcript of this episode.

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In today’s Office Hours, Eric answers Michelle's question: “what's one big purchase you've made and regretted later?"

Everyone experiences buyer's remorse at some point in their life, and Eric is no different. Hear what he has regretted purchasing in his life, and send us a message about your biggest spending regrets.

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome back to Don’t Retire… Graduate! Today’s guest is Tiffany Grant, a financial counselor and the host of the Money Talk with Tiff podcast. 

Tiffany is a fantastic content creator within the personal finance space—except for her online quiz that must be broken if Eric did not get a perfect score—and is one of the many money nerds making financial literacy accessible to the public. 

Listen to her story and take her online quiz (after you listen to Eric giving out the answers, of course) to see if you can beat Eric’s 92%. 

In this episode we’ll talk about:

• Tiffany’s upbringing that led her to financial and professional success 

• Student loans and how to go through graduate school without paying tuition and/or getting paid

• Financial literacy and the lack of education in most schools

• Extra credit assignments and why those who need help aren’t the ones who seek it

• The Money Talk with Tiff podcast and how it’s helping to spread financial education

Visit dontretiregraduate.com for a full transcript of this episode.

About Tiffany Grant:

Where do I start? I am a self-proclaimed money nerd and proud of it! I live and breathe finances. After years of giving impromptu advice to family and friends, I said why not start a blog? This way all of the knowledge will have an online platform and reach even more people!  

From a young age, I was always money-conscious. I remember being as young as 6 and clipping coupons. Did anyone use them? Nope, but I found joy in going through the motions. When I got my first job at 16, I used coupons to get more bang for my buck. Once I saw how helpful they were, I used coupons for everything! Cashiers were impressed by a teenager leaving with a cart full of items for only $20.  

​As time progressed, I wanted to do more with my money. I started investing at the age of 19. I had amassed a few thousand dollars but decided to sell it all when times got rough. Big mistake but I had to do what I could.  

I bought my first house at the age of 26. How? By saving, keeping a close eye on my credit, and living well below my means. Frugal is my middle name! Wealth-building is all about having goals and being laser-focused on accomplishing them. My next goal is to be debt-free (except the house) by age 30.

What makes this even more amazing is I did it all while being a single mother of two little boys, working full-time, and going to school. Now, what's your excuse? Let's get started! Time is ticking!

I have a Bachelor in Business Administration with a concentration in Management, Master of Business Administration (MBA), Accredited Financial Counselor (AFC), SHRM-CP, Lean Six Sigma Yellow Belt, and years of experience helping people like you!

https://www.moneytalkwitht.com/

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In today’s Office Hours, Eric answers Emily's question: “how does the 2022 market correction compare to prior market corrections and what should investors do?"

The factors causing the current market conditions are unique, but there is a common factor that exists between all the corrections we've seen in the past: fear. This episode will explain what is happening in the markets right now and what investors should be doing.

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome back to Don’t Retire… Graduate! Today’s guest is Natalie Torres-Haddad MPA, AWA, a two-time TEDx speaker, award-winning author, and the host of Financially Savvy in 20 Minutes.

Natalie’s story of being raised by immigrants during the LA Riots, experiencing the cultural differences between the rich and poor, and learning about money the same way she learned a second language should serve as inspiration for anyone struggling to reach financial independence. 

We are so glad to have her here to share her story, discuss what it’s like to be successful in an industry in which you’re underrepresented, and that sometimes you just need to give yourself a little grace. 

In this episode we’ll talk about:

• Natalie’s upbringing and personal finance became a language she had to learn

• Being patient with yourself and figuring out what you can learn in 20 minutes each day 

• Generational and familial differences and how we all struggle differently 

• The field of finance and how breaking through it as a woman and/or a person of color is still a challenge 

• Figuring out what works for you and giving yourself grace

• Learning from your mistakes more than when things go well

Visit dontretiregraduate.com for a full transcript of this episode.

About Nathalie Torres-Haddad:

She is an international award winning author, educator and bilingual podcast host of Financially Savvy in 20 Minutes. Her expertise has been featured in Forbes, Huffington Post, LA Times, and many news outlets like Telemundo and Fox. 

A two time TEDx speaker known for her talk “The foreign language of financial literacy”. 

Some of her videos have received over a million views and is a sought out keynote speaker all over the country as a financial literacy and mental health advocate. A first generation college graduate from CSULB, in Finance and International Business with a Masters from CSUN, she focuses on helping those with debt and working toward financial independence. Her first children's book in 2020 Made the #1 best seller on Amazon: "A dress to remember" based on the nonprofit LA's Prom Closet she had for several years. Born in El Salvador, and raised in Inglewood she quickly understood that the lack of financial literacy limits her community of basic human rights and equality in resources. She started investing in real estate at age 24 and began her career advocating for financial literacy.  

http://financiallysavvyin20minutes.com/

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In today’s Office Hours, Eric answers Tony's question: “What's the easiest way for a beginner investor to get started?”

The first step of any journey can be difficult, but in this case we think education is a great place to start. After that, it can depend on your goals and will take practice.

Have a question? Tweet it to us at @BrotmanPlanning, or post it on our Facebook and it may be used in a future episode of Office Hours!

Visit dontretiregraduate.com for a full transcript of this episode.

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Welcome back to Don’t Retire… Graduate! Today’s guest is Joseph Hogue, CFA®, the host of Let’s Talk Money! With Joseph Hogue, joining us to break down the art and science of investing and share his rules for making money in the stock market. 

Investing has become entertainment media and everyone wants to be slinging stocks, but Joseph shares his ideas about why very few people should really own individual stocks and why funds are better for the vast majority. Plus, hear his three rules to follow to not lose money when investing. 

In this episode we’ll talk about:

• What investing really is and how it can give everyone a taste of entrepreneurship 

• The reason people are scared or intimidated by investing 

• Human behavior and how we tend to make the wrong choices with our money

• Looking at stock market crashes as flash sales

• How to tell the difference between good financial advice and not-so good advice 

• Who should or should not own individual stocks and how to balance your portfolio for growth 

• The 3 rules to not lose money on stocks 

• When you should or should not sell your shares 

• Concentrated stock positions and overweighting your portfolio in one investment, including your own company 

• Income risk and financial risk in choosing your investments 

Visit dontretiregraduate.com for a full transcript of this episode.

About Joseph Hogue

Born and raised in Iowa, Joseph Hogue graduated from Iowa State University after serving in the Marine Corps. He worked in corporate finance and real estate before starting a career in investment analysis. He has appeared on Bloomberg and CNBC and led a team of equity analysts for a venture capital research firm. He holds a master’s degree in business and the Chartered Financial Analyst (CFA) designation. 

Joseph left the corporate world in 2014 to build his online businesses, first through creating websites and later through his YouTube channel, Let's Talk Money. He's since grown the community to over 550,000 and reaches more than 1.8 million people a month through the blogs, YouTube and a weekly market newsletter. 

https://www.youtube.com/c/LetsTalkMoneywithJosephHogueCFA

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In today’s Office Hours, Eric answers Julia's question: “I'm getting divorced. How do I know if I'm getting a fair split of marital assets?”

This can be a hard situation to navigate, but bringing in a financial professional is a great way to start.

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Season 5 is here and Don’t Retire… Graduate! is back to share more actionable strategies for reaching financial independence and talk to more money nerds about what they want to be when they grow up. 

And your eyes are not deceiving you—this season we’re recording in VIDEO! If you’re on an audio-only player, thank you so much for listening. If you’re watching our first time doing this on camera, thank you and welcome! 

Starting a new season is exciting enough, but we wanted to really kick it off, so we brought back one of our favorite guests and all-time favorite Stacker, Joe Saul-Sehy, host of the Stacking Benjamin’s podcast and co-author of the book STACKED: Your Super Serious Guide to Modern Money Management. 

Joe is back to share some of his experiences from his past life as a financial advisor, including the best and worst advice he’s ever heard and the red flags he’s seen from other advisors that should have you running for the office exit. 

In this episode we’ll talk about:

• Social media and the harmful financial advice that can be found on it

• What compliance means and how it keeps financial advisors from sharing bad information

• Identifying the filters, credentials, and backgrounds of the people you get advice from online

• Bernie Madoff, undisclosed insiders, and schemers to look out for 

• Red flags of financial advisors you can see just walking into the office—from what’s on the television to the layout of the furniture

• Asking who, not how when you need to do learn something new—like writing a great book with Emily Guy Birken 

Visit dontretiregraduate.com for a full transcript of this episode.

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1. Life Insurance Is an Asset: Life insurance isn’t just “death insurance”—it’s a buy-and-manage asset that can be valued, sold, and leveraged for retirement, business liquidity, or charitable giving.
2. The Life Settlement Market: Many policyholders don’t realize they can sell their policies in a regulated secondary market, often for more than the surrender value. This liquidity can solve long-term care needs, support philanthropy, or keep a business afloat.
3. Insurability Matters: Buying life insurance for children or grandchildren can preserve their insurability for life, opening doors for future financial planning—even if health challenges arise later.
4. Charitable Solutions and Giving While Living: Life settlements can fund significant charitable gifts, allowing donors to witness the impact of their generosity now rather than waiting for a bequest after passing.
5. Don’t Throw Away Your Policy—Value It First: Before surrendering or lapsing a policy, policyholders should explore its market value. Life insurance can be worth tens, hundreds of thousands, or even millions—and could change the trajectory of a family, business, or community.

In today’s Office Hours, Eric answers Jesse's question: "What advice do you have for someone interested in a career in finance or as an advisor?”

The career path for a financial advisor is not well-defined, but there are several ways to get into the industry for a successful career. 

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

Visit dontretiregraduate.com for a full transcript of this episode.

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Welcome back to Don’t Retire… Graduate! As part of our summer throwback series, we’re bringing back some of our favorite episodes from seasons passed.

This episode, originally released in season 3, features Heidi Herman, author of On with the Butter: Spread More Living onto Everyday Life. At 93 years old, Heidi’s mother made a list of 93 new experiences she wanted to try before she turned 94—from paragliding in Iceland to visiting the Great Barrier Reef to ziplining through the Mall of America. Now, Heidi joins us on the show to talk about the experiences her and her mother tried together and how they are inspiring others to embrace life fully.

In this episode we’ll talk about:

• Heidi’s mother and her secret to embracing life
• Ideas for exciting new experiences and ways to find something new you can try regardless of age or ability
• Thinking about what you want to be when you grow up and what you want to do when you’re no longer tied to a career
• The icelandic saying of Áfram með Smjörið and how it inspired Heidi and her mother

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In today’s Office Hours, Eric answers Ryan's question: “When and how do you come with a hard figure goal for your retirement savings?”

Setting a savings goal for retirement is trying to hit a moving target, so you should be revisiting this question regularly. But if you're trying to do the math, this episode can help. 

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome back to Don’t Retire… Graduate! As part of our summer throwback series, we’re bringing back some of our favorite episodes from seasons passed.

Today, we’re welcoming back Kristy Schiano, Yogi and owner of the Mindful Movement Center, to tell her story of tragedy, loss, strength, and resilience. While training for a triathlon, Kristy was hit by a truck and suffered severe physical and mental injuries, causing her to lose nearly everything—including the ability to walk and talk—but she held strong to hope and joy. Her recovery has centered around helping others manage their chronic pain through yoga and meditation. Listen to her story and take her extra credit assignment seriously (even if it won’t be graded)!

*Please note this episode is rereleased from season 1, and we will NOT be taking a break. Come back next week for another episode of Office Hours!*

In this episode we’ll talk about:

• Kristy’s story of being hit by a truck while training for a triathlon and needing to relearn everything we take for granted
• Financial, physical, and spiritual wellness and how they interact in our daily lives
• Using meditation and breathing techniques in times of stress and anxiety
• Pivot points we experience throughout our lives, both expected and unexpected
• Financial wellness, paying yourself first, and having a plan for the future
• Spirituality, religion, and the spiritual journey Kristy experienced through yoga
• The power of empathy and compassion

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In today’s Office Hours, Eric answers Brianna's question: “What is the real reason that financial advisors have asset minimums?”

Take a look under the hood to understand how financial advisors generate revenue, what asset minimums are for, and how BFG is doing things differently with Financial Planning for All. 

Have a question? Post it in the comments, tweet it to us at @BrotmanPlanning, or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome back to Don’t Retire… Graduate! As part of our summer throwback series, we’re bringing back some of our favorite episodes from seasons passed.

Today, we’re welcoming back our very own Yanni Niebuhr, CFP®, Chief Investment Officer here at BFG Financial Advisors. Originally released way back in our first season, this episode is still as relevant as ever and covers the financial planning from the perspectives of the Millennial and Gen X generations, and how people are planning differently about the next chapter of their lives. And please join us in congratulating our guest, who, in the time since this episode was recorded, welcomed his second baby boy!  

In this episode we’ll talk about:

• How retirement planning is a marathon, not a sprint, and why planning should start early
• How Yanni, a Towson University grad, got his start in financial planning and what he wants to be when he grows up
• The sandwich generation and multigenerational financial planning
• How millennials and adults in their twenties or thirties can be doing to prepare for retirement
• The average debt and student loans for recent grads and how it can hurt your financial independence
• Deciding what your financial priority should be
• Legacy planning and leaving behind things more important than money – freedom, independence, vision, values
• Talking about money within families and how views can vary with your parents, spouse, or grandparents
• Side hustles and how they’re impacting the idea of FIRE (financially independent retire early)
• Entrepreneurship and small business self-employment and how it can help you pursue your passions
• Social awareness and the importance it holds with younger generations
• Pensions, three-legged stools, social security and other antiquated retirement ideas being replaced by “you’re on your own”
• Living in two-income society vs older generations able to live on a single income
• Transferring wealth between generations, to children and grandchildren, in tax-efficient ways through life insurance, trusts, and 529 College Savings Plans without creating a Billy Madison situation
• Unemployment and underemployment, and the shrinking value of college degrees

Visit dontretiregraduate.com for a full transcript of this episode.

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In today’s Office Hours, Eric answers April's question: “Why do some advisors say that taking 5% or more of your retirement nestegg out every year is dangerous?”

Determining a reasonable withdrawal rate depends on factors including your asset level, retirement timeline, and age. Eric explains three different asset structuring strategies that can help you avoid outliving your money. 

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome back to Don’t Retire... Graduate! As part of our summer throwback series, we’re bringing back our very own Lena Nebel, CFP®, Chief Operating Officer here at BFG Financial Advisors. This episode, originally released in Season 3, dives into the topics around marriage that people don’t necessarily want to talk about, like how much to spend on the engagement ring, how to ask for a prenup, and what to do when you and your partner don’t agree on money topics.

In this episode we’ll talk about:

• The major purchase of engagement rings and best practices for budgeting, choosing a ring, and getting it insured
• When to talk about finances with your partner and what you should be talking about
• Who should be considering a prenuptial agreement and how do you address it
• Roles and responsibilities in the relationship and how to merge them as a couple
• Combining finances and determining which account should be separate and who is financially responsible for what
• Finding the happy medium when a spender marries a saver
• How to handle inheritances after marriage and determining if it’s a marital asset
• Estate planning as a married couple
• Looking at benefits and beneficiaries with the possibility of widowhood in mind

Visit dontretiregraduate.com for a full transcript of this episode.

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In today’s Office Hours, Eric answers Shelby's question: “what do you think every student should know before taking out student loans?”

Student loans can be confusing and there is a lot to know. We're talking about a few different factors including return on investment and whether or not the loan is subsidized. 

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Summer is in session but we’re not taking off! Throughout the season, we’ll be bringing back listeners’ favorite episodes from past seasons and answering brand new Office Hours questions!

Today’s episode from season 2 (originally released at the height of the COVID-19 pandemic) features Cait Lockwood (formerly Caitlin Pyle), founder of Work-at-Home School and Proofread Anywhere, talking about how she went from being fired from a job to building a seven-figure company she could run from home. Listen to this great conversation about how you can build your own business without leaving the house—even if you’re already retired.

In this episode we’ll talk about:

• Remote work and unemployment during and after the COVID-19 pandemic
• Cait’s journey from being fired to building two businesses
• Discovering the viability of full-time freelance work
• What it takes to be entrepreneurial and create your own company
• Advice for someone looking to change careers or generate additional income
• The three-step system for success as a freelancer
• Identifying the lies we’re programmed to believe that can keep us from reaching our full potential
• Breaking past the self-doubt that can hold you back and replacing them with truths
• Abundance mindset vs scarcity mindset
• Leveling up by identifying existing skills and learning new ones
• The importance of confidence in successfully launching as a freelancer
• Changing the way we see retirement and throwing out conventional idea of retirement
• The reality of fixed income and how you can un-fix it
• Thinking outside—or breaking out of—the box you’re in to make more money and reach financial independence
• Inflation rate and how it affects retirees and seniors more than the rest of us
• The main things seniors spend money on – leisure, health care, education for grandkids, and scratch-off lotto tickets
• The investment of online courses for building new skills
• Millennials, participation trophies, and accepting failure as a lesson
• Vetting online courses and creators and filtering out scams
• Understanding affiliate marketing and how you can use it to make commission income
• Using social media and your existing networks for market research and finding clients

Visit dontretiregraduate.com for a full transcript of this episode.

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1. Embracing Career Change: Hannah’s journey from teaching to finance demonstrates that transferable skills, like collaboration and data-driven thinking, are invaluable—even across vastly different industries.
2. Data-Driven Marketing: By applying her experience as a teacher, Hannah transformed our marketing approach—utilizing data to determine which initiatives, webinars, and podcast episodes best engage our audience.
3. The Power of Collaboration: Moving from a solo teaching role to a team environment at BFG allowed Hannah to learn from colleagues, share new ideas, and innovate more effectively than ever before.
4. Adapting to Growth and Change: Hannah’s advice to “slow down, trust the process, and implement change gradually” is a lesson for anyone stepping into a new role or industry.
5. Looking Ahead—Interactivity and Fresh Content: With “Diary of a Financial Advisor” moving to a webinar format on BFG University, our content will become more timely, interactive, and driven by what you—our listeners—want to see.

In today’s Office Hours, Eric answers Jenna's question: “how much should I have in an emergency fund?”

This can vary based on a lot of factors, and emergency funds don't need to just be in the form of savings accounts. Eric explores the different layers that can make up your emergency fund and the rules of thumb for how much money is safe. 

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome to the season four finale of Don’t Retire... Graduate! We’ve had amazing guests this season and couldn’t be more excited to finish with today’s guest. Dr. Daniel Crosby is a psychologist and behavioral finance expert who helps organizations understand the intersection of mind and markets and explores the way our brains affect our choices when it comes to money. He is here to talk about the way mental biases can affect our decision making and make us uniquely stupid when it comes to money (his words, not ours). 

In this episode we’ll talk about:
•Behavioral finance and looking at the role psychology plays in our financial lives 
•How people are uniquely stupid when it comes to money and how the brain reacts when thinking about money
•The biases we all can fall victim to that can negatively affect our investments 
•Decision making styles applied to money versus everywhere else in our lives
•The performance of Amazon stock over the past twenty years
•Day trading and how active investors tend to underperform 
•Action bias, confirmation bias, investing alongside your political party, investing alongside your morals, loss aversion, the house money effect, and mental accounting and how they all affect our financial choices 
•The value of a financial advisor versus doing it yourself 
•Results of studies on financial advising, including investors working with advisors accumulating far more wealth than those without advisors 
•The meaning of the term fiduciary and how it applies to finance and psychology 
•Giving up on dreams of professional sports careers
•Positive psychology, PERMA, and Dr. Martin Seligman’s contribution 
  
Visit dontretiregraduate.com for a full transcript of this episode.

Dr. Crosby's Book 

About Daniel Crosby

Dr. Daniel Crosby is a psychologist and behavioral finance expert who helps organizations understand the intersection of mind and markets. Dr. Crosby's first book, Personal Benchmark: Integrating Behavioral Finance and Investment Management, was a New York Times bestseller. His second book, The Laws of Wealth, was named the best investment book of 2017 by the Axiom Business Book Awards and has been translated into 7 languages. His latest work, The Behavioral Investor, is a comprehensive look at the neurology, physiology and psychology of sound financial decision-making.  

https://www.standarddeviationspod.com

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The truth is, you can do it all yourself or with the help of a few vendors. A financial planner is not necessarily needed. But which way is right for you?

Have a question? Post it in the comments, tweet it to us at @BrotmanPlanning, or post it on our Facebook and it may be used in a future episode of Office Hours!

Visit dontretiregraduate.com for a full transcript of this episode.

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Welcome back to Don’t Retire... Graduate! Today we’re going back to school with Rob Phelan, a high school math and personal finance teacher and author of the children’s book M is for Money. Rob is here, live from his classroom, to talk about money and the roadblocks we’re facing while advocating for personal finance education for kids. 

In this episode we’ll talk about:

•The difference between math and personal finance 
•Why we overestimate our abilities in nearly all aspects, but doubt our abilities to understand and make money
•Money stories and how we’re shaped to make decisions as children
•Why it’s so hard to create a formal education in personal finance
•The struggles teachers face when creating personal finance curriculums
•Nonprofit organizations that have resources available for schools and students 
•How kids can start learning about money as early as preschool and how we can teach money concepts at different ages
•Entrepreneurship, pre-selling a business idea, and crowdfunding
•Understanding regret and buyer’s remorse as a child
•The ice cream theory of teaching patience and delayed gratification to toddlers

Visit www.misformoneybook.com to learn more about Rob's book.
  
Visit dontretiregraduate.com for a full transcript of this episode.

About Rob Phelan

Rob Phelan is a high school math and personal finance teacher in Frederick, Maryland, a Certified Financial Education Instructor, business owner, and author of the recently published children’s book, M is for Money. 

Rob is a passionate advocate for greater levels of financial education to help our youth make better financial decision moving into their futures. 

Rob Phelan Facebook

Rob Phelan Twitter

Rob Phelan Instagram

Rob Phelan LinkedIn

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In today’s Office Hours, Eric answers Matthew's question: “is it better to pay over the asking price for a house or just rent?"

There is so much going on in the market right now that is making purchasing a home -- especially your first home -- particularly difficult and expensive. Do you go for it or wait it out?

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

A full transcript of this episode can be found at dontretiregraduate.com.

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Welcome back to Don’t Retire... Graduate! Our guest today did what nobody thought was possible: left Eric speechless. Sharita Humphrey has a remarkable story of grit and resilience. From a homeless mother of two living out of a motel, Sharita promised her sons that she would change their situation and did not rest until she did. The now award-winning financial educator is here to share that story and spread her message that just because you lose things, you can never lose hope. 

In this episode we’ll talk about:
• The importance of having money conversations at home 
• Sharita’s story of becoming a mom early, the feelings of failure that came with losing her home, and her experience living in a motel for close to a year
• How financial literacy education can change your financial trajectory 
• How it feels to leave traditional employment and scratch an entrepreneurial itch
• Keeping experiences as a line item on a budget 
• Creating a safety net by building an emergency fund 
• Creating jobs and abundance through agriculture 
• Seeing your budget as a blueprint to keep you in the driver’s seat 
  
Visit dontretiregraduate.com for a full transcript of this episode.

www.sharitamhumphrey.com

www.changeinmotion.co

About Sharita M. Humphrey

Sharita M. Humphrey is a nationally recognized, award-winning finance expert and money mentor. Having previously been broke and homeless herself, Sharita knows first-hand that financial freedom has a blueprint and she’s committed to helping individuals change the financial trajectories of their lives.  

Sharita is a certified financial educator, speaker, and coach. At her namesake financial consulting company, Sharita helps minority women better understand, manage, and grow their money. Sharita also helps Black and Brown entrepreneurs learn how to accelerate their businesses and secure funding through her other company, Change In Motion, which offers a comprehensive education program.  

In 2020, Sharita was named National Financial Educator of the Year for her work within her local community and across the country. She is a regular contributor to entrepreneurial publications and has been featured in top-tier media including CNBC, iHeartMedia, Forbes, Yahoo Finance and BBC World News.  

This year, Sharita and her family set a goal of purchasing hundreds of acres of land over the next few years to build a family-run farm. During their journey, Sharita is teaching minority farmers how to obtain monies to acquire farmland and helping them to retain their land for generations to come.  

Sharita M. Humphrey Facebook 
Sharita M. Humphrey Instagram
Sharita M. Humphrey Linkedin

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In today’s Office Hours, Eric answers Mark's question: "if you won the lottery and had the option of $30 million upfront or a million dollars a year for 30 years, which is actually the better option?"

Unfortunately this is not a circumstance many of us will see ourselves in, but let's talk about it anyway. What are the realities of winning the lottery?

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

Visit dontretiregraduate.com for a full transcript of this episode.

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Welcome back to Don’t Retire... Graduate! We have a very fun episode today and couldn’t be more excited to have Emily Guy Birken here. She is a lifelong money nerd, award-winning writer, and the co-author of STACKED: Your Super Serious Guide to Modern Money Management, written with longtime DRG friend, Joe Saul-Sehy. Emily joined us to talk about how to look at your money like a game of Tetris, the way gamification can be a powerful tool for change, and, of course, to set the record for the number of times “hemorrhoid” has ever been said on this show. 

In this episode we’ll talk about:
• Emily’s goals for every day
• How to see your finances as a Tetris game and use it to help with budgeting 
• How an emergency fund is the Easy Spin of budgeting 
• Taking control of your money rather than seeing it as something out of your control
• Gamification of money and when it is good versus when it can be harmful
• The mental activation that comes with gamification and identifying what behavior is being rewarded 
• Hiring an advisor who won’t bleed you dry and the three questions you should ask a financial advisor  
• How to know if your advisor is actively doing the work to help you meet your goals and recognize your money values
• Why you want an advisor who works with people similar to you
•  Paying attention to professional designations and understanding the regulations and standards that come with them
• Why a CFP (Certified Financial Planner) is the gold standard of financial advisors
• Understanding what an advisor does for his/her clients
• Who the perfect Stacked reader is
• Emily’s retirement readiness checklist and the things you should be thinking about to be ready to retire
• Identifying one good thing everyday   

No Stacking Benjamins hosts were harmed in the making of this episode. 

Visit dontretiregraduate.com for a full transcript of this episode.

Download Emily's Retirement Readiness Checklist at emilyguybirken.com/DRG

About Emily Guy Birken

Emily Guy Birken is a former educator, lifelong money nerd, and a Plutus Award-winning freelance writer who specializes in the scientific research behind irrational money behaviors. Her background in education allows her to make complex financial topics relatable and easily understood by the layperson.  

She is the author of several books, including The 5 Years Before You Retire, End Financial Stress Now, and the brand new book Stacked: Your Super Serious Guide to Modern Money Management, written with Joe Saul-Sehy.   

Emily lives in Milwaukee with her family. 

www.emilyguybirken.com

Facebook: Emily Guy Birken

Twitter: @EmilyGuyBirken

Instagram: @EmilyGuyBirken 

LinkedIn: Emily Guy Birken

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In today’s Office Hours, Eric answers Felix's question: what is the most valuable employee benefit I should take advantage of?

This is a great question and the answer varies by person, but there are a few employee benefit options that most people underutilize and even ignore.

Find a full transcript of this episode at dontretiregraduate.com.

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

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Welcome back to Don’t Retire... Graduate! We have two guests today, Steven and Lauren Keys, who did something pretty incredible: retired before they turned 30. They came on the podcast to talk about how they reached financial independence at a young age, how they saved their nest egg without large salaries, and their plan for the rest of their retirement. 

In this episode we’ll talk about:
• Cutting expenses to save money and pay off debt
• Living frugally without sacrificing your lifestyle 
• Using your passions to bring in extra income 
• How to make a full-time income with part-time work 
• Dispelling the myth that retirement means not working at all 
• Living with an abundance mentality rather than a scarcity mentality 
• Employee benefits without an employer
• Insurance considerations when in an early retirement 
• How money experiences growing up can affect your perspective on money as an adult
• Gamifying your finances to motivate you towards your goals
• Overconsumption and how to avoid it
• Using money to buy freedom rather than stuff
• The Financial Roadmap

Steven & Lauren's Financial Roadmap: https://www.tripofalifestyle.com/roadmap/

Visit dontretiregraduate.com for a full transcript of this episode. 

About Lauren ad Steven Keys:

We’re Lauren and Steven, a middle-class couple who managed to bank enough money to retire from our full-time jobs at age 29. By making a few lifestyle tweaks soon after graduation, we grew a buffer of cash and investments that gave us a ton of flexibility and enabled us to do some really fun stuff too, like taking six months off to explore Hawaii and another seven months to travel to every National Park in the US. Now we’re hoping to help other people (like you!) do something similar.

TripofaLifestyle.com

Facebook: Trip Of A Lifestyle

Twitter: TOALifestyle

Instagram: Trip Of A Lifestyle

Linked In: Trip Of A Lifestyle

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1. Pain to Purpose: Matt’s journey shows that personal pain can be transformed into service and purpose—helping others find hope and resilience amid their own struggles.
2. Recovery Is Lifelong: Addiction recovery, whether chemical or behavioral (like debt or spending), is a lifelong process. Accountability, support, and “speaking the truth in love” are critical for lasting change.
3. Financial Wellness Is Holistic: True financial wellness goes beyond dollars and cents—it's deeply linked to mindset, emotional health, and the support systems we build. Financial anxiety can persist even after basic needs are met, especially when rooted in past trauma or scarcity.
4. Generational and Individual Challenges: Our experiences around money, independence, and mental health are shaped by generational patterns, cultural backgrounds, and personal histories. There’s no “one-size-fits-all”—every journey is unique.
5. The Importance of Vision and Purpose: Building a vision for our future—even if it feels difficult or intimidating—is essential. Whether planning for retirement, caregiving, or breaking out of survival mode, a clear purpose helps us create better present and future outcomes.

In today’s Office Hours, Eric answers Gary's question: Are all financial advisors and planners fiduciaries?

This is a great question and the simple answer is no. Listen to hear Eric explain what a fiduciary is, why it's important to know if your advisor is a fiduciary, and how you can tell.

Have a question? Post it in the comments, tweet it to us at @BrotmanPlanning, or post it on our Facebook and it may be used in a future episode of Office Hours!

Find a full transcript of this episode at dontretiregraduate.com.

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Welcome back to Don’t Retire... Graduate! Today’s guest is the most educated individual we know in this industry. Dr. Mary Bell Carlson is a financial behavioral expert who has worked with the government, military, and financial educational organizations, is an adjunct professor of financial planning, and is the founder of Chief Financial Moms. She’s here to talk about gender differences in personal finance, money histories, and how we can get just one point better every day.

In this episode we’ll talk about:

•The asset shift from baby boomer men to women that will be taking place over the next decade
•How women and men look at financial advice and manage money differently 
•The need for women in financial planning
•Personal financial literacy education and how to know if your school is teaching it
•Understanding your money history and starting conversations about it as a couple
•How you can get even half a point better each day

Visit dontretiregraduate.com for a full transcript of this episode.

Resources mentioned in this episode: 

https://checkyourschool.org/

https://www.jumpstart.org/

https://freeguide.chieffinancialmom.com/

About Mary Bell Carlson

Dr. Mary Bell Carlson is a financial behavior expert and has worked in both the military and government communities for the last decade. From the bowels of the Pentagon to international audiences, Dr. Carlson has presented numerous financial seminars and worked on a variety of financial planning and education projects.

After getting married and having her two daughters, she started Chief Financial Mom.com, a personal finance education platform to help busy moms. Currently, she also works as adjunct faculty for the financial planning programs at both the University of Georgia and Texas Tech University.

ChiefFinancialMom.com

Facebook @ChiefFinancialMom 

Twitter @ChiefFinanceMom 

Instagram @ChiefFinancialMom 

YouTube Channel @Chief Financial Mom 

Linkedin @Mary Bell Carlson, Ph.D., CFP®, AFC® 

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In today’s Office Hours, Eric answers Alex's question: As a financial advisor, what is the most common mistake you see people making with their personal finances?

This was a hard question to answer because there are a LOT of mistakes people make. The common factor for all of them? Emotions.

Have a question? Post it in the comments, tweet it to us at @BrotmanPlanning, or post it on our Facebook and it may be used in a future episode of Office Hours!

A full transcript of this episode can be found at dontretiregraduate.com.

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Welcome back to Don’t Retire... Graduate! Today’s guest came ready for a debate and didn’t disappoint. Andrew Hallam, best-selling author and educator, is here to talk about his latest book, Balance, and investment techniques and ideologies that don’t necessarily match ours. If you’re interested in learning about index funds, passive asset management, and the true meaning of success in retirement (whether you’re retiring early or not), you won’t want to miss this episode. 

In this episode we’ll talk about:

• The cost and opportunity cost associated with Ivy league education.
• Recognizing a financial advisor that is great and one that just wants to sell you something
• The role psychology plays in financial services
• Debating controversial topics in personal finance: passive versus active portfolio management, index funds versus value index
• The traditional definition of retirement, why it is unhealthy, and how to do it better
• FIRE community and the FIRE movement, and the life satisfaction research that suggests it may not be the best goal
• The four legs of the success table: money, relationships, health, and purpose

https://andrewhallam.com/balance/

Visit brotmanmedia.com/podcasts for a full transcript of this episode.

About Andrew Hallam:

Andrew Hallam is the international best-selling author of Balance: How to Invest and Spend for Happiness, Health and Wealth; Millionaire Teacher: The Nine Rules of Wealth You Should Have Learned in School and Millionaire Expat: How To Build Wealth Living Overseas. Profiled on such media as CNBC, and The Wall Street Journal, he's also the first person to have a #1 selling finance book on Amazon USA, Amazon Canada and Amazon UAE. He has written columns for The Globe and Mail, Canadian Business, MoneySense, Swissquote and AssetBuilder. Since 2016 he has spoken at businesses and international schools in over 30 different countries.

Links:

https://andrewhallam.com/
https://www.facebook.com/groups/445218675653782 https://www.facebook.com/millionaireteacher
https://twitter.com/aphallam
https://www.linkedin.com/in/andrew-hallam-44b81627/

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We're seeing inflation in a way we haven't for generations, and there are things you can do to be better prepared.

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

Visit brotmanmedia.com for a full transcript of this episode.

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Welcome back to Don’t Retire... Graduate! We have a very special episode in honor of International Women’s Week. Kara Perez, the founder of Bravely Go, joins us to talk about financial feminism and how we can start breaking down the gender roles and inequalities we see in our culture. 

In this episode we’ll talk about:

• The meaning of financial feminism.
• The difference in financial power between men and women/non-binary individuals. 
• How the wage gap can affect financial security in retirement.
• The importance of having assets in your own name and checking your beneficiary designations. 
• The need for large-scale financial literacy education and where it can come from.
• Gender roles in our culture and their effect on financial equity. 
• Paying down debt and saving money on a low salary. 
• How Kara founded Bravely Go, the feminist financial education company. 
• Looking at personal finance from a broader lens.

Visit brotmanmedia.com/podcasts for a full transcript of this episode.

About Kara Perez:

Kara Perez is the founder of Bravely Go, a feminist financial education company. Bravely Go focuses on bringing actionable, intersectional and accessible financial education to people via pop up events and online community. Kara has been featured in the New York Times, Forbes, NPR, Glamour, ABC Nightline News, and US News and World Report as a financial expert. Additionally, Kara co hosts the award winning podcast The Fairer Cents, which has been named the top money podcast for women by Forbes and The Balance.

Links:
https://www.instagram.com/webravelygo/
https://twitter.com/bravelygo
https://www.facebook.com/webravelygo
https://www.tiktok.com/@webravelygo?lang=en
https://www.bravelygo.co/

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In today’s Office Hours, Eric answers Yazan's question: What are the pros and cons of using a robo-advisor for investing?

A robo-advisor has its place, and Eric explores this question from two perspectives: simple investment management and comprehensive financial planning.

Have a question? Tweet it to us at @BrotmanPlanning or post it on our Facebook and it may be used in a future episode of Office Hours!

Visit brotmanmedia.com/podcasts for a full transcript of this episode.

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Welcome back to Don’t Retire... Graduate! Today’s guest has had an amazing journey that led to retiring at age 27. Rachel Richards is the best-selling author of Money Honey and Passive Income, Aggressive Retirement and is here to tell her story and share her tips on how you can create your own passive income streams. 

In this episode we’ll talk about:

• How Rachel retired at 27 with $20,000 of monthly passive income
• Self-publishing tips for personal finance writers
• Why Money Honey was written to begin with
• Seeing market dips as a sale on stocks and an opportunity for a good deal
• The misconception of how you lose money in the stock market
• The value of time in growing wealth 
• Strategies for creating passive income streams and retiring early 
• The steps you take to designing your dream life
• Having a plan for what you want to do with your time in retirement, whether you’re retiring early or at a traditional age
• The importance of writing down your goals
• Recognizing if a financial advisor is a fiduciary or a scammer

Free budgeting worksheet: www.moneyhoneyrachel.com/worksheets 

Visit brotmanmedia.com/podcasts for a full transcript of this episode.

About Rachel Richards:

At the age of 27, Rachel Richards quit her job and retired, living off $15,000 per month in passive income. Rachel is the bestselling author of “Money Honey” and “Passive Income, Aggressive Retirement.” She built a real estate portfolio of 38 rental units by the age of 26. She is a former financial advisor, and has been featured in CNN and Business Insider. By making the topic of money management fun, entertaining, and simple, Rachel has helped thousands of millennials work their way out of financial despair.

Links:

• www.moneyhoneyrachel.com
• www.facebook.com/MoneyHoneyRachel
• www.instagram.com/moneyhoneyrachel

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In today’s Office Hours, Eric answers Jonathan's question: What are some realistic lifestyle changes that save money?

There are two ways to look at this question, and this episode covers both. How do you create the habit itself, and what are those changes? 

Have a question? Tweet it to us at @BrotmanPlanning and it may be answered in a future episode of Office Hours!

For a full transcript of this episode, visit brotmanmedia.com/podcasts.

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Welcome back to Don’t Retire... Graduate! Today’s guest is podcast royalty: the host of the Stacking Benjamins podcast Joe Saul-Sehy! Joe is here to talk about his latest book, Stacked, his take on the real estate and cryptocurrency crazes, and share his top tip for stacking your wealth.

In this episode we’ll talk about:

• Joe’s journey from financial advisor to teacher to writer to podcaster
• Building financial careers without financial backgrounds
• How, despite the massive amounts of financial resources available, people are still being left behind
• How many people end up crying over money, even if they’re making six figures
• The disconnect between our values and what we do with our money
• Social media’s effect on the popularity of real estate investing, cryptocurrency
• The idea of getting rich quick with cryptocurrency that can be dangerous for a lot of investors
• The evolution of the Stacking Benjamins podcast
• The important role that automation plays in growing wealth

Visit brotmanmedia.com/podcasts for a full transcript of this episode.

Link to the study: https://www.nonfiction.co/reports

Link to Joe's book: https://www.stackingbenjamins.com/stacked/

About Joe Saul-Sehy:

Joe is the creator and co-host of the Stacking Benjamins podcast and co-author of STACKED: Your Super-Serious Guide To Modern Money. Current board member at large of The Plutus Foundation. Former board president and Board Member of Partnership For The Pathway.

While Joe’s “money expert story” includes being a former financial advisor (16 years) and representing American Express and Ameriprise in the media. His real story is how he was a money disaster in his early life, pulled his financial house into order, and left his business at age 40 to pursue an entirely different path.

Joe was the “Money Man” at Detroit television WXYZ-TV, appearing twice weekly. His advice has appeared in Bride, Best Life, and Child magazines, the Los Angeles Times, Chicago Sun-Times, Detroit News and Baltimore Sun newspapers. He’s also appeared online in more than 200 different places, including CNBC.com and WSJ.com.

The Stacking Benjamins Show was called the “Best Personal Finance Podcast” by Kiplinger. Lifehacker listed the show as one of the top 10 of 2021. Joe and the SB team have won five Plutus Awards and the Academy of Podcasters “Best Business Podcast” award (beating well-known shows like The Tim Ferriss Show, How I Built This, and Gimlet’s StartUp).

The Stacking Benjamins Show is created in Joe’s mom’s basement in Texarkana, Texas, where Joe lives with his spouse Cheryl and their cat Cooper.

Links:

• www.stackingbenjamins.com
• www.joesaulsehy.com
• Twitter: @SBenjaminsCast
• Twitter: @AverageJoeMoney
• Instagram: @stackingbenjaminspodcast
• YouTube: StackingBenjamins
• Facebook: IStackBenjamins

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1. The Power of Professional Community: Andrew emphasized that working together with other financial advisors through the Financial Planning Association fosters collaboration, knowledge-sharing, and positive impact—rather than rivalry.
2. Legislative Advocacy Matters: Involvement with the FPA and similar organizations keeps financial advisors aware of regulatory changes and provides a voice to influence legislation that affects both advisors and their clients.
3. Financial Wellness for All Levels: Our corporate wellness program brings personalized financial guidance directly to employees, helping them understand complex benefits packages and make informed decisions regardless of their asset level.
4. Holistic Wellness is Essential: True financial planning goes beyond numbers—it’s about providing peace of mind, making sure beneficiaries and wills are in place, and reducing stress for both advisors and their clients.
5. Never Stop Growing: Andrew’s journey reminds us that ongoing professional development, community engagement, and the desire to elevate those around us are keys to a fulfilling and impactful career in financial planning.

In today’s Office Hours, Eric answers Sara's question: Should I be trying to pay off my mortgage early with extra payments or put that money to a different use?

Of course, this is another case of "it depends." Listen to Eric explain when it may be a good idea to invest that extra money and when it's okay to make that mortgage number start falling.

Have a question? Tweet it to us at @BrotmanPlanning and it may be answered in a future episode of Office Hours!

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Welcome back to Don’t Retire... Graduate! Today’s guest is a comedian, best-selling author, and activist who turned being told they are bad with money into a success career in finance media. Gaby Dunn hosts the Bad with Money podcast, which talks about money in a way that is raw and honest, and the author of Bad with Money: The Imperfect Art of Getting Your S*** Together. We are so excited to have them here to talk about the taboos and baggage around money and how humor may be able to change it.

In this episode we’ll talk about:

• How to get YouTube famous and be broke at the same time
• Gaby’s journey as a content creator and how they got started in personal finance
• The shame and embarrassment we feel about our net worth, whether its high or low
• The relativity of wealth 
• Investing and finance apps gamifying investing and the danger it can impose on users
• Getting addicted to stock trading and checking the markets
• Student loans and the debt crisis
• Student loans vs medical debt vs other types of debt
• The difficulties that Millennials and Gen Z face that is different than any generation before them
• How paying attention to your finances is the first step—and maybe the hardest—to being good with money

Visit brotmanmedia.com/podcasts for a full transcript of this episode.

About Gaby Dunn:

Gaby Dunn (they/them) is a New York Times bestselling author, comedian and LGBTQ advocate living in Los Angeles. Gaby has served as a writer on BIG MOUTH (Netflix) and has developed original television pilots with MTV, 20th Century Fox, YouTube Originals, FX and Netflix. Gaby is the host and creator of the podcast, Bad With Money with Gaby Dunn, now in its eighth season, where they have interviewed guests like Suze Orman, Andrew Yang, and Elizabeth Warren. A non-fiction book based on the podcast was published by Simon & Schuster in 2019. Gaby co-wrote the novels I Hate Everyone But You, a New York Times bestseller in 2018, and the sequel Please Send Help… published in 2019. Gaby’s debut original graphic novel, Bury The Lede, in partnership with BOOM! Studios is currently being adapted as a television series and both of Gaby’s latest novels garnered a placement on The 20 Best LGBTQ Books of 2019 list by Harper’s Bazaar. Most recently, they created, and starred in the Audible Original series Apocalypse Untreated. They are also the co-host of the Just Between Us podcast on the Forever Dog network.    

Links:

• www.gabydunn.com
• Bad with Money podcast: https://podcasts.apple.com/us/podcast/bad-with-money-with-gaby-dunn/id1144712710 
• Instagram: @GabyRoad 
• Facebook: https://www.facebook.com/groups/398914378105641 

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In today’s Office Hours, Eric answers Robert's question: If your close friend is a financial advisor and keeps telling you how to manage your money, how do you get them to stop?

This can be an uncomfortable situation and sometimes you don't want to mix business and friendships. And it goes both ways. Are you an advisor constantly being pestered for free advice on your time off? Here's how to handle it. 

Have a question? Tweet it to us at @BrotmanPlanning and it may be answered in a future episode of Office Hours!

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