Episode 58: The $10M Restlessness, AI IPO Stock Decisions, and Heirloom Construction

Episode 59: Family Property Tax Traps, I Bonds vs. Treasury Ladders, and Rethinking the Prenup with Aaron Thomas

A couple owns three properties across two states and has been letting their adult children and grandchildren use them freely. Their CPA recently raised concerns about imputed rental income and gift tax. Stephan walks through where the real risk actually sits, why personal use among family typically doesn't trigger imputed income rules, and when the picture genuinely changes — namely, when a property is also being rented commercially. The bigger takeaway may be that it's time for a second opinion. Next, a listener sold a business eighteen months ago and is sitting on twelve million in cash split between a high-yield savings account and a money market fund. With a two to five year horizon, is there a real case for Series I bonds, a Treasury ladder, or both? Stephan addresses the I bond purchase limits, why they can't meaningfully move the needle at this scale, and the tax efficiency case for direct Treasuries versus money market funds. He also raises the more important question hiding underneath: how much of that cash should actually be sitting on the sidelines at all. Then in From the Field, Stephan sits down with Aaron Thomas, a Harvard Law graduate, three-time winner of Atlanta's Best Divorce Attorney, founder of Prenups.com, and author of the Amazon bestseller The Prenup Prescription. Aaron has represented more than a thousand clients in high-stakes family law cases. Together they reframe prenuptial agreements as a foundation for financial clarity rather than a defensive measure, walk through the mine, yours, and ours framework, explore how to approach the conversation without leading with the word prenup, and discuss how families with generational wealth can protect assets built over decades while still honoring the full partnership of marriage. Stay in touch beyond the podcast: Newsletter: https://scholarfinancialadvising.com/newsletter [https://scholarfinancialadvising.com/newsletter] Start your planning journey: https://scholarfinancialadvising.com/welcome [https://scholarfinancialadvising.com/welcome] Submit a question for the show: https://scholarfinancialadvising.com/podcast [https://scholarfinancialadvising.com/podcast] Disclaimer: The information provided in this podcast is for general informational and educational purposes only and should not be considered financial, investment, or professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investments involve risk, including possible loss of principal, and past performance does not guarantee future results. Listeners should consult with a qualified financial advisor before making any financial decisions based on the content of this podcast. Always consider your individual financial situation, objectives, and risk tolerance. Thanks for listening!

Episode 58: The $10M Restlessness, AI IPO Stock Decisions, and Heirloom Construction

"In this episode, we hear from a business owner in his mid-forties with around ten million saved who has noticed that every financial milestone, hitting his first million, paying off the house, watching the number keep climbing, has failed to bring the sense of arrival he expected. Stephan walks through why the pattern is so common, how the marginal value of every additional dollar changes once basic needs are met, and the mistakes that follow when someone ties their identity to a number rather than to what the wealth actually enables. Next, we hear from a software engineer at one of the major AI companies heading toward what could be the largest IPO in history, sitting on equity worth more than fifteen million if everything holds. With SpaceX, Anthropic, and OpenAI all approaching potential liquidity events, Stephan explains why the pre-IPO window is where the most planning leverage exists, how ISOs and the alternative minimum tax create real liquidity problems, how the one-and-two-year holding periods unlock long-term capital gains treatment, and where charitable planning through a donor-advised fund can fit in before the event rather than after. In our From the Field segment, we are joined by Matt Lutz, Managing Director of Flatwater Homes, a luxury residential construction firm based in Milwaukee with more than 40 years of experience delivering some of the most technically extraordinary private builds in North America. We talk about a one-of-a-kind glass-walled natatorium, an underground 30-car garage, the features that push the boundaries of what is possible, and what an ongoing relationship between a family and their builder actually looks like across decades. ---------------------------------------- Stay in touch beyond the podcast: Newsletter: https://scholarfinancialadvising.com/newsletter [https://scholarfinancialadvising.com/newsletter] Start your planning journey: https://scholarfinancialadvising.com/welcome [https://scholarfinancialadvising.com/welcome] Submit a question for the show: https://scholarfinancialadvising.com/podcast [https://scholarfinancialadvising.com/podcast] ---------------------------------------- Disclaimer: The information provided in this podcast is for general informational and educational purposes only and should not be considered financial, investment, or professional advice. The opinions expressed by the hosts and guests are their own and do not necessarily reflect the views of any affiliated organizations. Investing involves risk, including the potential loss of principal. Past performance is not indicative of future results. Listeners should consult with a qualified financial advisor or professional before making any financial decisions based on the content of this podcast. The hosts and guests are not responsible for any actions taken based on the information shared. Always consider your individual financial situation, objectives, and risk tolerance. Thanks for listening!

Episode 57: Q&A Speed Round with Noah and Evan: AI Investing, Living Off Dividends, 529-to-Roth, and More

This week we're doing something a little different. Instead of the usual two-question format with a guest interview, we're handing the mic over to Associate Financial Advisors Noah Lewis and Evan Mills for a Q&A speed round covering eight shorter questions from listeners. The first half focuses on investing. Noah and Evan discuss how to think about AI as a structural shift without taking on outsized concentration risk, why international allocation still has a place in a portfolio even after a decade of US outperformance, and whether a retiree should restructure to live off dividends or take a total return approach with strategic selling. They also work through why an intermediate-term bond ETF like BIV might be preferred over a money market fund, and where I-bonds and TIPS fit into the current rate environment. The second half turns to planning. The conversation covers smarter ways for grandparents to fund private school tuition beyond just writing a check, how the new SECURE 2.0 provision for rolling overfunded 529 balances into a Roth IRA actually works, and the differences between charitable remainder trusts and donor advised funds and when each one makes sense. ---------------------------------------- Stay in touch beyond the podcast: Newsletter: https://scholarfinancialadvising.com/newsletter [https://scholarfinancialadvising.com/newsletter] Start your planning journey: https://scholarfinancialadvising.com/welcome [https://scholarfinancialadvising.com/welcome] Submit a question for the show: https://scholarfinancialadvising.com/podcast [https://scholarfinancialadvising.com/podcast] ---------------------------------------- Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor who can assess your individual financial situation, objectives, and risk tolerance. Thanks for listening!

Episode 56: $200K a Year in AUM Fees, Buying Your Nanny a Car, and Education with Lindsay Tanne Howe

A listener with $18 million at a wirehouse advisor is paying just over $200,000 a year in AUM fees and was told by his advisor that there's no way he could handle a portfolio that size on his own. Stephan separates the management of money from the advice on money, walks through why the AUM model scales well for advisors but poorly for clients, and gives a real answer on where the threshold for self-management actually sits. Spoiler: it's much higher than most advisors will admit. Then, a family with a longtime nanny on payroll wants to provide her a safe new vehicle now that the daily drive to private school has changed the job. Stephan walks through three structures, including the option most families overlook, and explains why insurance is the biggest risk most people miss when a personal vehicle starts getting used for what looks like commercial work. To close, Lindsay Tanne Howe, founder and CEO of LogicPrep, returns to the show for a conversation on how education is increasingly driving where families choose to live. Stephan and Lindsay discuss the big-fish small-pond question that comes up in places like Greenwich, the rise of new family hubs from Lisbon to South Florida, when families should start planning for college (earlier than most assume), and how AI is reshaping both the admissions process and what colleges are teaching once students arrive. ---------------------------------------- Stay in touch beyond the podcast: Newsletter: https://scholarfinancialadvising.com/newsletter [https://scholarfinancialadvising.com/newsletter] Start your planning journey: https://scholarfinancialadvising.com/welcome [https://scholarfinancialadvising.com/welcome] Submit a question for the show: https://scholarfinancialadvising.com/podcast [https://scholarfinancialadvising.com/podcast] ---------------------------------------- Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor who can assess your individual financial situation, objectives, and risk tolerance. Thanks for listening!

Episode 55: 529 Superfunding, Evaluating Memberships After a Liquidity Event, and Concierge Nursing

When you have a $40 million estate and four grandchildren, superfunding 529s can feel like an obvious estate planning move — but the math isn't always as clean as it looks. Stephan explains how the five-year election works, how it interacts with your annual gifting strategy, and why at this level of wealth, 529s may be the wrong vehicle entirely when compared to trusts, GRATs, or direct giving. Next, Stephan addresses the very common situation that follows a major exit: everyone wants a piece of it. From an $85,000 golf club initiation to fractional aviation cards to family office intro services, the pitches are relentless and they all sound reasonable. Stephan offers a clear framework for how to evaluate each category — and why the answer for most of them, at least right now, is probably no. Finally, Jasmine Bhatti of NaviNurses [https://navinurses.com/] joins to pull back the curtain on what personalized healthcare looks like for families who want more than the standard of care. The conversation covers private duty nursing, how to use long-term care policies strategically before hitting an exclusion threshold, post-surgical recovery at home versus skilled nursing facilities, and the broader concierge healthcare ecosystem — from longevity medicine to integrative physicians to nurses as connectors across the entire care landscape. Stay in touch beyond the podcast: Newsletter: https://scholarfinancialadvising.com/newsletter [https://scholarfinancialadvising.com/newsletter] Start your planning journey: https://scholarfinancialadvising.com/welcome [https://scholarfinancialadvising.com/welcome] Submit a question for the show: https://scholarfinancialadvising.com/podcast [https://scholarfinancialadvising.com/podcast] Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor who can assess your individual financial situation, objectives, and risk tolerance. Thanks for listening!