Episode 54: Mortgages, Trusts, Hedge Funds, and More: Live Q&A from Our Annual Conference

Episode 62: The SpaceX IPO, the Magnificent Ten, and What's Quietly Breaking Underneath the Market

This quarter's Scholar Big Picture conversation runs the full episode. Deon Strickland, financial advisor at Scholar Advising, in-house economist, and finance professor at Wake Forest University, joins Stephan to work through the most consequential shift in public markets right now: the SpaceX IPO and what its $2.5 trillion valuation says about how investors are pricing the tail scenarios on AI. From there the conversation moves into the concentration problem underneath the headlines, with the Magnificent Ten approaching forty percent of the S&P 500 and Anthropic and OpenAI likely to add another four to five trillion dollars in market cap to that same narrow window. They close on what it means to build a portfolio for clients who have not felt real market pain in nearly two decades, why bonds and gold are starting to look more like insurance than drag, and what Deon is watching as a new Fed chair takes over heading into the next inflation print. Stay in touch beyond the podcast: Newsletter: https://scholarfinancialadvising.com/newsletter [https://scholarfinancialadvising.com/newsletter] Submit a question for the show: https://scholarfinancialadvising.com/podcast [https://scholarfinancialadvising.com/podcast] 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 61: Preparing the Spouse Who Doesn't Manage the Money, When Vacation Rental Income Disappears, and Preparing Heirs with Jessica McGawley

This week we open with a listener in her early sixties who has managed every dollar of her family's nineteen-million-dollar balance sheet for thirty years, while her husband has never opened a statement. A recent health scare has forced the question of what happens when the spouse who runs everything is suddenly out of the picture. Stephan walks through the operational knowledge gap that shows up in long marriages with significant assets, why the family balance sheet matters more than the portfolio statement, and how to bring the non-managing spouse into the relationship before it becomes a crisis. Then we hear from a couple at 63 whose beach house income just disappeared overnight. A county zoning change killed short-term rentals on their street, and the ten thousand a week they were factoring into their plan is gone. The house is worth around four million, they have another nine million invested, and they don't strictly need the income. The conversation reframes the decision entirely: this is not a real estate question, it's an asset purpose question. Would you buy this house today at four million if you were starting from scratch? And in From the Field, Jessica McGawley, founder of Dallington, joins us on what gets missed when families prepare wealth for the next generation. For more than a decade, Jessica has worked with the rising generation across multigenerational families and family enterprises, building curriculum and coaching around the things traditional estate planning leaves out. We talk identity, isolation, the three options every family business actually has, and why preparing the people matters as much as preparing the documents. 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] 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 60: Buying a Business in the Era of Mass Retirement

Brandon Mendez, Ph.D., CPA, Professor of Finance at the Darla Moore School of Business at the University of South Carolina, joins Stephan in the studio for a conversation on the wave of business acquisitions reshaping private markets right now. With a generation of business owners hitting retirement age at the same time, private equity firms are moving fast, and individual buyers are competing in a market that is more crowded and more complex than it has ever been. Brandon and Stephan work through how to evaluate multiples and what seller discretionary earnings actually obscure, why PE has a structural advantage that individual buyers rarely overcome on price alone, how AI is beginning to shift the talent calculus for anyone acquiring a business, and what the financial statement red flags look like before you sign an NDA and after. 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] 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 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!