In this episode of Keep Hustling, host Aaron Gordon sits down with Chris Picciurro, CPA and founder of Teaching Tax Flow, to dig into practical tax planning strategies for entrepreneurs and working families. Chris shares his journey from Detroit newspaper boy to tax expert, highlighting how early entrepreneurial experiences shaped his mission to educate others. The conversation covers why everyone needs a "personal boardroom," tax tips for side hustlers, the difference between tax prep and tax planning, and common financial pitfalls - plus actionable advice for building wealth at any income level. Chris also discusses the generational shift in retirement mindsets and the importance of financial literacy for achieving long-term success. If you're ready to take control of your finances, gain strategic tax insights, and keep your hustle moving forward, this episode is packed with must-hear wisdom.

Get To Know Chris Picciurro Chris Picciurro, CPA, MBA, PFS, ARA

Integrated CPA Group (Co-Founder and Executive Officer)

Teaching Tax Flow (Founder)

Monthly Recurring Revenue Institute (Founder)

Educator

Podcaster

Chris is a highly respected expert in US-based Tax Planning and Strategy for Real Estate Investors, with international recognition as a presenter on the subject. He is based in Franklin, TN, where he currently resides with his family.

Chris holds several accreditations, including a CPA, MBA, PFS, and ARA. He is an accomplished public speaker, recognized for delivering informative and engaging presentations at notable events hosted by organizations such as the National Association of Tax Professionals (NATP), Michigan Association of CPAs, and the Memphis Investment Group.

He also previously participated as an Adjust Professor at Baker College and Davenport University.

He served on the Intuit Tax Council (2017-2020) and is an active member of several professional organizations, such as the MICPA (task force leadership), TNCPA, NARPM, and Dave Ramsey. He is a Co-founder and Executive Officer of the Integrated CPA Group (ICPA), and the Founder of Teaching Tax Flow (TTF) and the Monthly Recurring Revenue (MRR) Institute.

Chris' passion for tax planning and strategy led him to start his private CPA practice in Algonac, MI, in August 2002, with a 100% member-based subscription model focused on real estate investors and entrepreneurs. This led directly to the creation of Teaching Tax Flow, an online community dedicated to helping taxpayers, tax professionals, CPAs, and implementation partners legally and ethically reduce the taxes paid over their lifetime.

Aside from his professional life, Chris enjoys hobbies such as pickleball, travel, outdoor exercise, real estate investing, and spending time with his family. He also enjoys his time in front of the mic, co-hosting the Teaching Tax Flow podcast and frequently appearing as a guest on other shows in his limited spare time.

Chris' commitment to bringing tax planning and strategy to the masses is evident in his efforts to bring his experience and proprietary tax planning system accessible to all. He believes in empowering taxpayers with the knowledge to make informed decisions and reduce their tax liabilities.

Website

Teaching Tax Flow Podcast LinkedIn Instagram Faceboook

3 Episode Key Takeaways 1. Understand Your Financial Boardroom:Chris Picciurro drives home the importance of building both a personal and professional "boardroom" - a network of trusted advisors like accountants, attorneys, and insurance experts. He stresses that no matter your income level or background, everyone deserves access to guidance that can unlock smarter decisions and better financial outcomes. Don't be intimidated; being proactive and asking questions can transform your financial future.

2. Turn Tax Planning into Empowerment:A central lesson from Chris is that successful tax planning isn't just for high earners - it's essential for entrepreneurs and everyday hustlers alike. By understanding that tax agencies are your "involuntary business partners," you can take ownership over how much you pay, using proactive strategies to reduce your lifetime tax burden legally. Even simple moves, like tracking deductions and considering retirement account options, can yield significant long-term benefits.

3. Reject Limiting Beliefs About Income & Investing:The episode challenges the mindset that you need to be wealthy to benefit from tax planning or start investing. Chris shares real examples—like saving on taxes as a DoorDash driver or starting with small, consistent investments in Roth IRAs—to show that smart financial habits and wealth-building are attainable at any income level. The key is to start with even the smallest steps, avoid excuses, and believe that your hustle today can create a more secure tomorrow.

Show Overview: 00:00 Cursed Jets, Blessed Mets

05:41 Customer Service Lessons from Paper Route

08:01 Empowering Entrepreneurs Through Tax Strategy

10:46 Empower Yourself: Choose Your Tax

14:20 Entrepreneurial Mindset for Retirement Planning

19:23 Building Wealth: Start Early Habits

22:01 Retirement Liquidity Challenges for Seniors

24:39 Success Defined by Happiness

27:59 Planning Mobility and Home Investment