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About This Podcast
Becoming Work Optional is the go-to podcast for millennial business owners and executives who want to defy traditional retirement expectations by living a financially independent, work-optional life before their 60s.
Join Rachael and Matt as they leverage expert interviews, real-life case studies, and almost two decades of experience advising high-net-worth clients to share actionable tips that help you save money on taxes, invest for your future, and align your money with your ideal life.
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Recent Episodes
S1E30 #030 - Overrated Financial Planning Topics
In this episode of Becoming Work Optional, Matt and Rachael focus on overrated financial planning topics, emphasizing the importance of distinguishing between effective strategies and those driven by…
S1E29 #029 - Everything you Need to Know About Electing S-Corp
In this episode of Becoming Work Optional, Matt and Rachael focus on the benefits and considerations of electing S-Corp status for business owners, particularly regarding self-employment tax savings.…
S1E28 #028 - Building a Lifestyle Business in 30hrs/Week
In this episode of Becoming Work Optional, Matt and Rachael interview Matt Chiappetta, a CPA turned solopreneur, shares insights on his journey to achieving work optional status while emphasizing the…
S1E27 #027 - Aleksandr Volodarsky and his journey from Soviet Union to Entrepreneurship
In this episode of Becoming Work Optional, Matt and Rachael interview Aleksandr Volodarsky, CEO of Lemon.io. They discuss his journey growing up in the Soviet Union to building a successful tech…
S1E26 #026 - 2025 Tax Planning For Your Business
In this episode of Becoming Work Optional, Matt and Rachael focus on proactive tax planning strategies for business owners to optimize their financial outcomes in 2025. Key topics include the…
S1E25 #025 - How to Start a Business Without Destroying Your Financial Goals with Justin Peters
In this episode of Becoming Work Optional, Matt and Rachael interview Justin Peters where they discuss the concept of achieving work optional status, focusing on the balance between financial…
S1E24 #024 - "Retirement" After a Life of Serial Entrepreneurship
In this episode of Becoming Work Optional, Matt and Rachael interview Carl Landau, an entrepreneur who has built and sold multiple businesses and now embraces a lifestyle of "unretirement" through…
S1E23 #023 - Tax Hacks from $250MM Founder Ankur Nagpal: Do These 6 Moves Before Year-End
In this episode of Becoming Work Optional, Matt and Rachael interview Ankur Nagpal, a successful entrepreneur who shares insights on achieving work-optional status and the importance of tax savings…
S1E22 #022 - Being Poor Sucks: How to Change the Money Beliefs Holding You Back with Dr. Brad Klontz and Adrian Brambila
In this episode of Becoming Work Optional, Matt and Rachael interview Dr. Brad Klontz and Adrian Brambila, discussing their new book "Start Thinking Rich," which explores 21 harsh truths about money.…
S1E21 #021 - Liz Giorgi on Building a Business That Gave Her Financial Freedom in Her 30’s
In this episode of Becoming Work Optional, Matt and Rachael interview Liz Giorgi, Emmy Award winner and CEO of Soona, discussing her entrepreneurial journey, emphasizing the importance of financial…
S1E20 #020 - What To Do With A Bonus or Windfall
In this episode of Becoming Work Optional, Matt and Rachael discuss what to do when receiving a large bonus or windfall. They emphasize the importance of tax planning and working with a team of…
S1E19 #019 - The Reality of Dividend Investing
In this episode of Becoming Work Optional, Matt and Rachael delve into the nuances of dividend investing, discussing both its advantages and tax implications. They break down the concept of…
S1E18 #018 - From Bankruptcy to Billionaire: How Ron Carson Overcame a Financial Scarcity Mindset
In this episode, Rachael interviews Ron "Omani" Carson where he shares his journey from a challenging childhood in Nebraska to becoming a successful financial advisor and business owner, emphasizing…
S1E17 #017 - The Shift to Impact Work
In this episode, Rachael and Matt discuss the mindset shift required when transitioning to a fully work optional status. They emphasize the importance of shifting focus from money to impact work and…
S1E16 #016 - Making the Most of Employee Stock Options
Episode Summary:In this episode of the 'Becoming Work Optional' podcast, Matt and Rachael delve into the intricacies of employee stock options, exploring both their benefits and complexities. They…
S1E15 #015 - Generational Wealth
In this episode, Matt and Rachael discuss the concept of generational wealth and the goals that clients have for helping their children financially. They explore different tools and strategies, such…
S1E14 #014 - What You Should Expect From a Financial Advisor
In this episode, Rachael and Matt discuss the important steps and expectations to consider when choosing a financial advisor. Whether you’re looking for comprehensive financial planning or need help…
S1E13 #013 - Traditional vs. Roth
In this episode Rachael and Matt discuss the traditional versus Roth debate when it comes to retirement contributions. They emphasized the importance of considering individual variables such as tax…
S1E12 #012 - Avoid the Most Common Financial Mistakes
In this episode, Rachael and Matt tackle common financial mistakes and delve into the complexities of insurance coverage, investment strategies, and tax planning. From the misallocation of savings to…
S1E11 #011 - Sacrifices required for a Work Optional life
Episode Summary: In this episode of "Becoming Work Optional," hosts Rachael and Matt discussed the concept of becoming work optional, emphasizing the importance of giving up status games, living…
Frequently Asked Questions
Becoming Work Optional has published 30 episodes since December 2023, covering topics in Business, Entrepreneurship.
Becoming Work Optional is currently dormant with new episodes every 2 weeks. Average episode length is 42m.
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