The Scholar Wealth Podcast

This week, Stephan breaks down what to consider before converting a 401(k) to a Roth — from comparing current and future tax brackets to using partial conversions and asset location to minimize taxes. Next, he turns to the headlines about gold hitting record highs and explains how investors should think about gold’s role in a portfolio without getting caught up in short-term performance. And in ou...

This week: two listener questions that highlight the tension between family, finances, and legacy. First, we explore how couples can approach disagreements over whether to spend more now or preserve more wealth for their children. Next, we break down the risks of concentration when a large share of net worth is tied up in a family business, and how to weigh reinvesting versus diversifying. In our...

This week, we take on three listener questions that reveal the real-life complexity of wealth planning. First, how should parents handle fairness in gifting when one child values a large family wedding and another prefers a smaller celebration but asks for the same amount in cash? Next, a tech executive with most of his $6 million net worth tied up in stock options faces the uncertainty of an upco...

We start with a question from a couple who each set up SLATs during the high exemption years. With inflation and rising living costs, they’re now wondering whether to adjust trust distributions with cost-of-living increases or more flexible payout provisions. Stephan explains the options for modifying SLATs, the role of HEMS standards, and the trade-offs between flexibility, asset protection, and...

This week’s episode starts with a question from a couple who inherited complications after their parents passed with wills only. Now that their own estate is $5 million, they want to avoid the same outcome for their kids. Stephan explains when it makes sense to move from wills to a trust and the benefits of control, protection, and probate avoidance. Next, we hear from an investor pitched on a pri...

Is keeping all your cash and investments at one major bank simply convenient, or a hidden risk? Stephan explains the differences between FDIC and SIPC insurance, what each actually protects, and if splitting accounts across banks and custodians can provide a valuable safeguard for liquidity and access. Next, we explore how to select a distribution schedule for a nonqualified deferred compensation...

In this episode of the Scholar Wealth Podcast, Stephan Shipe answers three listener questions that highlight the real-world decisions families face at different stages of wealth. First, we look at a parent’s dilemma when their 23-year-old daughter wants to invest $50,000 in crypto. How can families encourage curiosity and independence in investing while setting guardrails to protect long-term weal...

This week’s episode opens with a listener wondering whether to help their brother with a down payment on a new home. The brother plans to repay the funds after selling his current house, but how do you balance protecting your wealth with supporting family? Stephan breaks down the risks, protections, and alternatives to consider. Next, we hear from an attorney preparing to make partner at their law...

In this episode of the Scholar Wealth Podcast, we tackle big wealth strategy questions. First, Stephan answers whether now is the right time to sell a gold coin collection worth $250,000, with gold prices at record highs. We cover how to value a gold collection, when to sell gold coins, and how to identify a fair auction house commission versus being taken advantage of. Next, we explore currency d...

This week’s episode starts with a question from a business owner preparing for a future liquidity event, with about $20 million currently tied up in private company stock. Stephan walks through how to manage the risk of overconcentration, ways to diversify before the sale, and how to preserve your business legacy through thoughtful planning. Next, we hear from a listener deciding whether to join a...

This week’s episode starts with a question from an executive who has about half of their net worth tied up in company stock. Stephan walks through why that level of concentration can be risky, how a 10b5-1 plan works, and the tax and compliance considerations that come with diversifying. Next, we hear from a parent who has been funding their kids’ 529 plans for years and is close to fully funded....

This week’s episode starts with a question from a family debating whether to keep their fractional jet ownership or buy a midsize jet outright. Stephan walks through the tax benefits, depreciation rules, and hidden costs that factor into the decision—and why the math isn’t as simple as cost per hour. Next, we hear from an executive with a large stock option package who wants to exercise wisely wit...

We kick off this week's episode with a question from a divorce attorney who listens to help his clients make smarter financial decisions. Stephan shares what really matters when dividing assets like real estate, retirement accounts, and taxable investments... and why equal isn’t always equitable. Next, we hear from a physician couple in their late 30s who just paid off student loans and want to kn...

Thinking about buying a rental property or vacation home? We start this episode with a listener question on whether real estate still makes sense in today’s market. We walk through the impact of high interest rates, what kinds of returns to expect, and when alternatives might be a better fit. Next, we tackle a tricky family planning question: how to handle gifting down payments to children who liv...

Thinking about launching a solo consulting business? We kick off this episode with a listener question about whether to choose a sole proprietorship or LLC—and how that decision affects taxes, liability, and retirement account options like a Solo 401(k). Then we shift gears and tackle a timely economic topic: why the Federal Reserve hasn’t cut interest rates yet, even as inflation cools. We break...

This week on the Scholar Advising Podcast, we’re tackling three client questions about managing wealth for the next generation and preparing for future tax changes. First, we look at how an irrevocable trust can help families lock in today’s higher estate tax exemption before the 2026 sunset—and how to align trust planning with long-term gifting goals. Next, we dive into pre-IPO planning: what to...

This week on the Scholar Advising Podcast, we’re tackling three thoughtful listener questions—each one focused on what to do when your plan, or someone else’s, needs a reset. We start with inflation: if it doesn’t cool down as expected, should you revisit your numbers? We’ll walk through how to adjust spending, allocation, and expectations without derailing your long-term goals. Next, we address h...

What’s the real return on your vacation rental—and how should you plan for taxes, depreciation, and long-term upkeep? In this episode, we talk through how to evaluate income property profitability and when to treat it like a true investment versus a lifestyle asset. Next, we explore what to consider before relocating to a no-income-tax state—including often-missed costs, estate tax rules by state,...

Three physicians. Three very different financial questions. In this episode, we unpack real scenarios from high-income earners navigating career growth, variable income, and burnout. First, we address retirement planning for locum tenens physicians—what options exist when there’s no employer-sponsored plan? Next, we talk strategy with a private practice physician whose income varies with revenue s...

What happens when your net worth is concentrated in a single asset—like a family business—and you want to diversify without triggering a big tax bill? In this episode, we talk through real scenarios from clients navigating legacy planning, lifestyle transitions, and wealth transfer decisions. We cover strategies for reducing concentration risk using gradual sales, ESOPs, and hedging tools like opt...

Sitting on cash, whether in a corporate account or on the sidelines of the market, can feel safe, but is there a more strategic move? In this episode, we chat through real questions from business owners and high-net-worth investors looking to make smarter use of their wealth. From deciding whether to reinvest profits or take a distribution, to reentering the market after sitting in cash, we explor...

Managing wealth after a big payout or a high-earning career isn’t always straightforward. In this episode, we chat through real scenarios from tech founders and medical professionals who are facing complex financial choices. From weighing mortgage payoff against retirement investing to setting up charitable funds, we explore how to prioritize goals while keeping an eye on long-term tax efficiency....

In this episode of the Scholar Wealth Podcast, Stephan Shipe discusses how to strengthen both sides of your financial partnership—at home and with your advisor. He begins with a common concern: one spouse often manages most of the household finances while the other stays less involved. Stephan explains why it’s essential for both partners to understand the family’s financial picture and how simple...

In this episode of the Scholar Wealth Podcast, Stephan Shipe explains the crucial difference between tax planning and tax advice—and how collaboration between your financial advisor and CPA can prevent costly surprises. He outlines when to bring your accountant into the process, how proactive modeling can help hedge against future tax increases, and why complex events like IPOs, business sales, an...

In this episode of the Scholar Wealth Podcast, Stephan Shipe tackles two practical questions that come up often for hands-on investors: Can you just buy the same financial planning software advisors use and do it yourself? Stephan explains where consumer tools fall short, the hidden complexity behind professional financial models, and why the real value of a financial plan isn’t in the software—it...