
#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. ...
12 Feb 202536min

#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 ...
29 Jan 202558min

#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 compa...
15 Jan 20251h 2min

#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 importan...
1 Jan 202544min

#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 independ...
11 Des 20241h 8min

#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 pod...
27 Nov 20241h

#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 fo...
13 Nov 20241h 2min



















