Financial Literacy – Ideas By Mike™ Podcast

The 10% Problem Facing Third-Generation Family Businesses | Ideas by Mike™ EP61

By Ideas by Mike | October 26, 2026

Why do so few family businesses make it to the third generation? In this episode of the Ideas by Mike™ Podcast, Mike Milligan, CFP sits down with Jason Shupp, and he shares how his family’s St. Louis roofing company navigated generational change—and what business owners can learn from its story. Jason reflects on his grandfather’s beginnings, his father’s role in growing the company, and his own unexpected return to the family business after years away.

He explains the challenges third-generation leaders face as they balance changing circumstances with the values and reputation built by earlier generations. Together, Mike and Jason explore the practices that helped the business endure: a strong work ethic, professional advisors, and a commitment to stewardship. Jason also explains how advisory boards can help business owners step back from day-to-day operations, think strategically, and find a trusted sounding board for important decisions.

In this episode, you’ll hear about:

Why third-generation family businesses face a difficult path to survival
How work ethic and professional guidance can support a successful transition
What it means to preserve a family business’s values and brand
How an advisory board helps owners gain perspective and plan for the long term
Why a trusted board can reduce uncertainty and build confidence in business decisions
How curiosity and listening can deepen empathy and understanding

Jason is a podcast host, speaker, and empathic collaborator. Before joining his family’s business, he worked in a range of roles, including as an EMT, whitewater raft guide, snowmobile tour guide, martial arts instructor, and high-works rigger. After nearly two decades helping lead a legacy business, he now brings his experience to advisory work and creative projects. He also hosts From There to Here, a podcast exploring the stories and experiences behind people’s paths. This conversation is for family business owners, founders, and next-generation leaders thinking about succession, growth, and how to build a business that can last.

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Do you have any financial inquiries wanting to get answered?

Leave us an email – contact@mikemilligancfp.com
Call/Text Mike Milligan to help you out – 757-909-7151
Visit our website at: www.1oakfinancial.com
Read our blogs to learn more insights: 1.oak Financial Blogs page

Episode 61 of Ideas by Mike™ with Jason Shupp is also available on YouTube!

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IRMAA Explained: The Hidden Medicare Surcharge That Costs Retirees Thousands | Ideas by Mike™ EP60

By Ideas by Mike | October 9, 2026

Did you know crossing an income line by just $1 in retirement could cost you and your spouse thousands of dollars every year?

In this episode 60 of the Ideas by Mike™, Mike Milligan, CFP sits down with Mark Annese, IRMAACP™, a technologist, data analyst, and creator of the IRMAA Certified Planner designation (now merged with the National Social Security Association).

Mark Annese explains how the Income-Related Monthly Adjustment Amount (IRMAA) acts as a hidden tax surcharge on Medicare Part B and Part D premiums—and why most retirees don’t realize they’ve triggered it until it’s too late.

Don’t forget to subscribe and leave a comment below!

Do you have any financial inquiries wanting to get answered?

Episode 60 of Ideas by Mike™ with Mark Annese, IRMAACP™ is also available on YouTube!

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Find Your One of a Kind: From Knowing the Problem to Fixing Your Retirement | Ideas by Mike™ EP41

By Ideas by Mike | July 31, 2026

Are you living your own dream—or performing a script someone else wrote for you?

We had a big podcast planned that was never produced that we will get to at the end of 2026 called 51 miler.

This will serve as the prequel to that podcast and a bookmark for the mysterious 41st podcast that was never dropped.

In this raw, unfiltered episode of Ideas by Mike™, host Mike Milligan, CFP®, steps up to the microphone alone to deliver a urgent message about sociology, borrowed desires, and what it truly takes to break free from the sea of financial sameness.

Drawing inspiration from Canadian artist TALK’s hit songs Run Away to Mars and GTFU, sociologist Erving Goffman, and philosopher René Girard’s concept of “mimetic desire,” Mike explores how so many hardworking professionals end up on a stage they never chose, chasing someone else’s version of retirement.

A portfolio built on envy, a career built on someone else’s expectations, or a legacy built on corporate templates is NOT a One-of-a-Kind Life. Learn what is the true process to be One of a Kind. We’d love to hear your thoughts, listen, share and download.

Don’t forget to subscribe and leave a comment below!

Do you have any financial inquiries wanting to get answered?

Episode 41 of Ideas by Mike™ is also available on YouTube!

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The Massive Structural Differences When Evaluating Bitcoin vs Crypto | Ideas by Mike™ EP55

By Ideas by Mike | July 17, 2026

Is your financial advisor still stuck in the 1960s? In this episode of Ideas by Mike™, host Mike Milligan, CFP sits down with Eric Runge, a third-generation entrepreneur and founder of Veritas Wealth, to discuss the institutionalization of financial planning and why standard commoditized products like the 60/40 portfolio are failing modern investors.

What You’ll Learn in This Episode:

– The Problem with Big Banks: Why institutions like Merrill Lynch and Edward Jones have more incentive to sell what has always worked instead of staying on the cutting edge.

– The History of Money: How walking off the gold standard in 1971 accelerated government debt and consumer inflation.

– Bitcoin vs Crypto: Why Bitcoin is a completely separate structure from the thousands of other cryptocurrencies on the market.

– The Future of Digital Currency: How SEC regulations, institutional family offices, and payment rails are shifting the landscape for Bitcoin.

Watch it on YouTube!

Click this link: Watch Now!

About our Guest:

Eric Runge Eric Runge is a third-generation entrepreneur who transitioned from corporate America to establish his own path in independent wealth management. In 2017, he founded Veritas Wealth to escape corporate compliance constraints and better serve his clients with fully customized decisions. He has since specialized his practice into a highly specific niche, establishing himself as a registered investment adviser expert in Bitcoin.

Drawing from a rich family history of business ownership—ranging from his grandfather’s heavy equipment rental shop to his father’s real estate business—Runge brings a direct, transparent, and agile entrepreneurial mindset to his practice. He caters extensively to high-net-worth investors and family offices, translating complex economic shifts into clear, actionable financial strategies.

Do you have any financial inquiries wanting to get answered?
Leave us an email – contact@mikemilligancfp.com
Or Call/Text Mike Milligan to help you out – 757-909-7151

Visit our website at: www.1oakfinancial.com

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Financial Therapy 101: How Your “Money Scripts” Controls Your Future | Ideas by Mike™ EP54

By Ideas by Mike | July 3, 2026

In this latest episode of Ideas by Mike™, our guest speaker, Erika Wasserman shares a deep-frame work and explains the history why retirement as an emotional and subconscious journey, drawing in listeners searching for deeper understanding. It then unpacks Erica’s key insights with concrete examples, tools, and frameworks—highlighting tangible benefits and outcomes.

Erica Wasserman, a renowned financial therapist, reveals how childhood stories, cultural beliefs, and subconscious patterns shape your money decisions today—and how recognizing these stories can transform your retirement journey. Erica guides us through how to identify and reframe these deep-rooted beliefs, so they serve your future—not sabotage it.

You’ll discover the surprising power of renaming your retirement accounts to boost motivation, learn simple exercises to connect with your retirement vision, and understand why emotional readiness is equally vital as financial planning.

With practical tools like conversation cards and a step-by-step framework, Erica shows how even the toughest talks—about money, aging parents, or transitioning roles—can be approached with confidence and clarity.

This episode breaks down the common money myths that keep couples silent, explores the critical conversations for harmony, and shares how to create a flexible, meaningful retirement—what Erica calls Phase Three—where passion, purpose, and financial security blend seamlessly.

If you or your clients are approaching retirement or questioning their money mindset, this is your essential guide to navigating it with emotional intelligence and purpose.

Perfect for financial advisors, couples preparing for retirement, or anyone ready to make their money story work for them—not against them.

Don’t let subconscious scripts define your future; learn to tell a new, empowering story today.

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About Our Guest:

Erika Wasserman is CEO of Your Financial Therapist, which she founded in 2019. As a Certified Financial Therapist CFT™, a sought-after certification held by only 100 people in the world, she combines her education in finance and international economics with her passion for helping others, empowering individuals, couples, and companies to reshape the way they think about money.

Visit her website at: https://yourfinancialtherapist.com/

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Also Get the Book “The One of a Kind Financial Plan” on Amazon: https://a.co/d/hAOPAgM

Stream all past episode of Ideas by Mike™ Podcast on YouTube: https://www.youtube.com/playlist?list=PLZ3KupZ4PKZW7NBOjRRQxRCSOSpS0G2ok

(Ep. 53): The Non-financial Side of Early Retirement – https://www.youtube.com/watch?v=luxc4m-mU2U&t=17s

Follow our Socials for more updates:
Mike Milligan, CFP® – https://www.linkedin.com/in/mikemilligancfp/
1.oak Financial Website – https://www.1oakfinancial.com/
LinkedIn Company Profile – https://www.linkedin.com/company/102585896/
Facebook: 1.Oak Financial – https://www.facebook.com/ideasbymike
Instagram: @1oakfinancial – https://www.instagram.com/1oakfinancial/
Ideas by Mike on Spotify Podcast – https://open.spotify.com/show/4Nxq9bIB3MRbetP3nXtQlk?si=dc4ee5e8ee564501
Ideas by Mike on Apple Podcast – https://podcasts.apple.com/us/podcast/ideas-by-mike/id1750701949

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Do you have any financial inquiries wanting to get answered?
Leave us an email – contact@mikemilligancfp.com
Or Call/Text Mike Milligan to help you out – 757-909-7151

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How to Retire into a Dream Job: The Emotional Nature of Retirement | Ideas by Mike™ (Ep. 52)

By Ideas by Mike | June 5, 2026

In this latest episode of Ideas by Mike™, Dr. Ives Machiz, PhD, CFP®, a fee-only pioneer, shares lessons from 4 careers on retiring into purpose. Learn how coaching and financial education build self-sufficiency & reduce anxiety.

Join Ideas by Mike™ host Mike Milligan, CFP® & Dr. Ives Machiz, PhD, CFP®, a clinical assistant professor and financial planning pioneer, shares the wisdom gained from his extraordinary four-part career: founding a fee-only firm in the 1980s, teaching high school, navigating a family business exit, and earning a PhD.

They both tackled and discusses the emotional nature of retirement and business transitions, the core lessons of self-sufficiency from coaching basketball, the relationship between financial education and health, and the advisor’s critical role in building client trust to mitigate financial anxiety.

This episode offers essential retirement advice for pre-retirees seeking to leap from working to living a one-of-a-kind life.

Key Takeaways:

Objective Advice Requires Total Alignment: True fiduciary planning centers entirely on the individual’s specific long-term goals rather than a high-pressure push for a specific item, commission, or asset product.
Master the Fundamentals First: Successful retirement planning is built on basic, non-glamorous behaviors: consistent long-term saving, clear spending budgets, and maintaining discipline through fluctuating financial environments.
Transitions Are Emotional First: Selling a business, leaving a job, or entering retirement forces individuals into an identity vacuum. You must establish a clear plan for your lifestyle and purpose before executing the final financial liquidation.
The Inherent Value of a Third-Party Fiduciary: Much like medical professionals who refuse to treat their own families, everyday investors need neutral professionals to remove toxic emotion from highly personal wealth decisions.

About our Guest:

Dr. Ives Machiz, PhD, CFP® earned his doctorate in Personal Financial Planning from Kansas State University. He is currently a Clinical Assistant Professor in the personal Financial Planning program at Arizona State University. (Source link)

Connect with Dr. Ives on LinkedIn

Subscribe to our YouTube and Tune in to find your starting line!

Also Get the Book “The One of a Kind Financial Plan” on Amazon: https://a.co/d/hAOPAgM

#moneymanagementpodcast #financialplanningpodcast #Finance #Inflation #RetirementPlanning #EconomicHistory #IdeasByMikePodcast

**We’d love to hear your thoughts! Don’t forget to subscribe and leave a comment below!**

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Family Wealth Strategy: From One Generation to the Next | Dr. Megan McCoy (EP. 50)

By Ideas by Mike | April 24, 2026

Are your childhood memories secretly managing your money? 🤔

We ALL have these stories.

On this week’s episode of the Ideas by Mike podcast, I sat down with Dr. Megan McCoy, one of the top academic minds in financial therapy. We went deep into the psychology of how we handle money across every generation.

Dr. McCoy even shared her own vulnerable money story about how wanting to “save the world” made her think she had to take a vow of poverty—and how she rewrote that narrative. It was absolute podcast gold.

If you’ve ever felt paralyzed by a financial decision, or if you’re arguing with your spouse about money, this episode is basically a free therapy session.

Connect with Dr. Megan McCoy:
LinkedIn: https://www.linkedin.com/in/megan-mccoy-phd/

Watch the full episode here: YouTube Link

To learn more about us, visit www.1oakfinancial.com | Don’t forget to subscribe to our YouTube Channel for latest updates!

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Tax Strategies for High-Income Earners Who is “Time Poor But Cash Rich” with Keshav Kolur (EP. 49)

By Ideas by Mike | April 10, 2026

Is your wealth over-concentrated in company stock? In this episode of Ideas by Mike podcast, host Mike Milligan, CFP, sits down with Keshav Kolur—a former software engineer at Amazon and Meta who walked away from the cubicle to build Clive Capital.

Keshav reveals how he applies a “tech brain” to evaluate real estate, oil, and gas deals to minimize downside risk. If you are a high-income earner who is “time poor but cash rich,” this episode is your blueprint for rewriting your financial story through passive income and sophisticated tax strategies.

In this episode, you’ll learn:

Why tech employees are often dangerously over-concentrated in RSUs.
The specific “engineering guardrails” Keshav uses to vet private equity deals.
How to legally and ethically slash your tax bill through alternative assets.
The journey from Georgia Tech robotics to managing a multi-million dollar fund of funds.
Alternative Investments 2026 and the Passive Income for Tech Employees.
Real Estate Syndication Strategies and how to do RSU Diversification.
Tax Saving Strategies for High Earners.
Meta & Amazon Employee Wealth.
Oil and Gas Passive Income and doing Engineering Mindset in Investing.

Connect with Keshav Kolur:
Website: https://www.clivecap.com
LinkedIn: https://www.linkedin.com/in/keshavkolur
Free Resource: 100+ Question Due Diligence Checklist – https://www.clivecap.com/alternative-assets

Watch the full episode here: YouTube Link

To learn more about us, visit www.1oakfinancial.com | Don’t forget to subscribe to our YouTube Channel for latest updates!

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(Ep. 47) 3 Communication Mistakes Financial Advisors Make (And How To Fix Them) | Deirdre Van Nest

By Ideas by Mike | March 13, 2026

Cut through the “sea of sameness” in financial advice by using communication as your competitive edge. In this episode of Ideas by Mike (Ep. 47), Mike Milligan, CFP, talks with communication expert Deirdre Van Ness about the three common mistakes advisors make, why effective speaking starts with strong content and emotional resonance, and how AI and gender dynamics are shaping the industry.

Main points: three advisor mistakes, content-first speaking, emotional connection, AI’s role, fewer women in finance.

Like, comment, and subscribe for more episodes on financial communication and advisor growth.

Episode Summary: This episode of Ideas by Mike features Deirdre Van Ness discussing how financial advisors can escape the “sea of sameness” through powerful communication.

Main Topics:

The Power of Communication: Using communication as a “superpower” to build trust and influence.
Three Communication Mistakes: Avoiding common pitfalls by treating every conversation as a leadership audition.
Human-AI Collaboration: Leveraging AI for efficiency while using the human element to customize the Final Output.

To learn more about us, visit www.1oakfinancial.com | Don’t forget to subscribe to our YouTube Channel for latest updates!

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(Ep. 46) Real Reason Why Rich People Pay Less in Taxes – Tax Planning Tips & Tricks with KC Chohan

By Ideas by Mike | February 27, 2026

In this 46th episode of the Ideas by Mike podcast, host Mike Milligan, CFP interviews KC Chohan, founder of Together CFO, who specializes in tax strategies for high-net-worth individuals and entrepreneurs.

KC shares his journey from working in a Fortune 500 company to becoming a fractional CFO, emphasizing the importance of understanding tax loopholes and structures to optimize financial outcomes.

The conversation covers various topics, including the future of taxes, the differences between W-2 employees and entrepreneurs, charitable giving, and real-time tax planning scenarios. KC also warns about scams in the tax planning space and stresses the importance of understanding tax strategies before signing any agreements.

YT Link: Ideas by Mike Podcast Episode 46 – Click this link to watch it on YouTube

About our Guest:

KC Chohan is a tax strategist and the founder of Together CFO, a firm dedicated to helping entrepreneurs, solopreneurs, and high-net-worth individuals legally minimize their tax liabilities. He specializes in transitioning business owners into family office structures to protect their assets and optimize their long-term wealth.

Connect with KC Chohan on LinkedIn
Together CFO – (YouTube –‪@TogetherCFO‬)
Instagram – Kc Chohan Together CFO

To learn more about us, visit www.1oakfinancial.com | Don’t forget to subscribe to our YouTube Channel for latest updates!

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