Q&A: Retirement Investing for Entrepreneurs, Medical School Debt, & Our Favorite Books and Podcasts

Dec 25, 2025

This discussion dives into maximizing financial stability for midlife tech earners and the advantages of using an LLC with S-Corp election for tax savings. The hosts break down the nuances between S-Corp payroll versus distributions and their impact on overall costs. They also explore the emotional balance between paying off low-rate mortgages versus investing. Listeners get insights on building a rental investment base and favorite resources for 2025, including key investing tools and recommended reading.

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ADVICE

Diversify Employer Stock And Build A Cash Buffer

Diversify away from concentrated employer stock and build indexes or real-assets exposure.
Keep 4–6 months of expenses in a high-yield cash account and consider non-market diversification like REITs or precious metals.

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ADVICE

Keep Low-Rate Mortgage; Consider A Recast

Avoid paying off a very low-rate mortgage because positive arbitrage favors investing cash.
Consider a mortgage recast to lower monthly payments while keeping the 2.6% rate for stability if job risk rises.

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ADVICE

Use An S‑Corp And SEP IRA When Earnings Are High

If you earn >$100k as a contractor, form an LLC and elect S-corp to pay a reasonable salary and take distributions.
Use a SEP IRA from W-2 compensation to reduce taxable income and boost retirement savings.

Get the Snipd Podcast app to discover more snips from this episode

Maximizing Stability for Midlife Tech Earners

02:53 • 8min

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Using an LLC with S‑Corp Election

11:03 • 5min

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S‑Corp Payroll vs Distributions Example

16:28 • 54sec

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When S‑Corp Strategies Help Employees

17:22 • 6min

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Paying Off a Low‑Rate Mortgage Versus Investing

23:16 • 5min

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SMAs, Military Pay, and Homebuying Advice

27:48 • 1min

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Saving Strategy for a First Rental Purchase

28:54 • 5min

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Favorite Books, Podcasts, and Tools of 2025

34:06 • 4min

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Why Whole‑Life/IUL Policies Often Lose

• Mentioned in 36 episodes

Millionaire Mission

Craig Ruby

#16

• Mentioned in 368 episodes

Think and Grow Rich

Napoleon Hill

Published in 1937, 'Think and Grow Rich' is a seminal work in the self-help genre. The book is the result of over twenty years of research by Napoleon Hill, who studied the habits and achievements of more than 500 successful individuals, including Andrew Carnegie, Thomas Edison, and Henry Ford. Hill distills their wisdom into thirteen principles that, when practiced with persistence and faith, can transform dreams into reality. These principles include the power of desire, faith, specialized knowledge, organized planning, and the role of the subconscious mind. The book emphasizes the importance of maintaining a positive mental attitude, setting clear and specific goals, and taking consistent action to achieve success. It also explores the concept of the 'Master Mind' alliance and the need to overcome fears and doubts to achieve one's objectives.

#263

• Mentioned in 82 episodes

The Five Types of Wealth

Sahil Bloom

• Mentioned in 1,178 episodes

Atomic Habits

James Clear

Atomic Habits by James Clear provides a practical and scientifically-backed guide to forming good habits and breaking bad ones. The book introduces the Four Laws of Behavior Change: make it obvious, make it attractive, make it easy, and make it satisfying. It also emphasizes the importance of small, incremental changes (atomic habits) that compound over time to produce significant results. Clear discusses techniques such as habit stacking, optimizing the environment to support desired habits, and focusing on continuous improvement rather than goal fixation. The book is filled with actionable strategies, real-life examples, and stories from various fields, making it a valuable resource for anyone seeking to improve their habits and achieve personal growth.

#1668

• Mentioned in 22 episodes

The Little Book of Common Sense Investing

John Bogle

#342

• Mentioned in 70 episodes

The Richest Man in Babylon

George Clason

This book, written by George S. Clason, uses a series of parables to convey fundamental principles of personal finance and wealth accumulation. Published in 1926, it remains highly relevant today, offering practical advice on saving, investing, budgeting, and financial discipline. The parables are engaging and easy to understand, making complex financial concepts accessible to readers of all backgrounds. Key principles include paying yourself first, living within your means, and making money work for you through wise investments. Despite its historical setting, the book's core lessons are adaptable to modern financial practices and have had a profound impact on countless readers worldwide.

#27

• Mentioned in 288 episodes

Zero to One

Notes on Startups, or How to Build the Future

Peter Thiel

In 'Zero to One,' Peter Thiel argues that true innovation comes from creating something entirely new, going from 'zero to one,' rather than incrementally improving existing ideas. He emphasizes the importance of vertical progress through technology and the benefits of monopoly in driving innovation. Thiel also discusses the need for long-term planning, the importance of finding the right co-founders, and the power law in startup success. The book challenges conventional wisdom and encourages readers to think critically and aim big to build the future.

#162

• Mentioned in 115 episodes

One Up On Wall Street

Peter Lynch

In 'One Up On Wall Street,' Peter Lynch explains how average investors can outperform professionals by leveraging their everyday experiences and knowledge. Lynch advocates for investing in companies and products that are familiar and understandable, rather than following trendy or complex investments. He provides easy-to-follow advice on analyzing financial statements, identifying different types of companies (such as cyclical, turnaround, and fast-growing companies), and maintaining a long-term investment strategy. The book emphasizes the importance of simplicity, patience, and fundamental analysis in achieving successful investments.

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Disclosure: All investing involves the risk of loss, including loss of principal. Brokerage services for US-listed, registered securities, options and bonds in a self-directed account are offered by Public Investing, Inc., member FINRA & SIPC. Public Investing offers a High-Yield Cash Account where funds from this account are automatically deposited into partner banks where they earn interest and are eligible for FDIC insurance; Public Investing is not a bank. Cryptocurrency trading services are offered by Bakkt Crypto Solutions, LLC (NMLS ID 1890144), which is licensed to engage in virtual currency business activity by the NYSDFS. Cryptocurrency is highly speculative, involves a high degree of risk, and has the potential for loss of the entire amount of an investment. Cryptocurrency holdings are not protected by the FDIC or SIPC.

Alpha is an experimental AI tool powered by GPT-4. Its output may be inaccurate and is not investment advice. Public makes no guarantees about its accuracy or reliability—verify independently before use.

*Rate as of 11/6/25. APY is variable and subject to change.

See terms and conditions of Public’s ⁠⁠⁠⁠⁠⁠⁠ACATS & IRA⁠⁠⁠⁠⁠⁠⁠ Match Program. Matched funds must remain in the account for at least 5 years to avoid an early removal fee. Match rate and other terms of the Match Program are subject to change at any time.

Hankwitz Group LLC has an existing business relationship with NEOS Investment Management LLC. The opinions expressed are those of the author, and the author owns several NEOS ETFs.

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