Failing Forward: How One CPA Found Success in Tax Entrepreneurship

On this episode, Chris Picciurro shares his experiences as a CPA and entrepreneur, discussing his journey to creating a successful practice and launching Teaching Tax Flow, a community focused on tax planning and strategy. He emphasizes the importance of time blocking and finding a balance between work and personal life, and shares his advice for his younger self to trust himself and have confidence in the future.
  • (00:00) - People aren't being taught how to be entrpreneur's
  • (00:26) - Thank you to Engineered Tax Services
  • (01:05) - Welcome to the Healthy, Wealthy, & Wise Accountants Podcast
  • (01:55) - Welcome Chris to the show
  • (05:42) - Some background on Chris
  • (09:17) - How do you manage your client relationship working remotely?
  • (12:52) - Availability is your best ability
  • (14:58) - Tell me about the path of your career
  • (17:52) - How do you use technology to help you and your firm?
  • (22:54) - Was it difficult to transition to a subscription based model?
  • (26:15) - What else are you working on and where are you evolving?
  • (31:50) - How do you monetize Teching Tax Flow and that structure?
  • (35:17) - Are you afraid that you're giving too much information away?
  • (37:52) - What makes you tick? What is your passion?
  • (42:07) - Do you have time now for your personal life? How do you balance everything?
  • (46:44) - What do you know now that you would tell your 20 year old self?
  • (48:20) - Wrap up and where to reach Chris and learn more about TTF
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This Podcast is brought to you by Engineered Tax Services. To learn more visit

Creators and Guests

Heidi Henderson
Heidi Henderson
I am a Tax Consultant and Real Estate Investor, and podcast host of Healthy, Wealthy & Wise. I advise clients on the application of Tax Efficiencies relating to their investments both directly and indirectly. My education is in Accounting but my entrepreneurial spirit has led me through many business ventures. But I love finding money for people who didn't know it was there! Cost Segregation, 179D deduction, 45L credits, R&D tax credits, Historical Tax Credits, Conservation Easements, Opportunity Zones, Alternative Investments, and Captive Insurance are a few tools we can help you with. As the Executive Vice President and Board Member of Engineered Tax Services I help plan for growth and operational improvements internally, while working externally with investment minded individuals to optimize their investment. I also teach over 30+ Continuing Education courses annually to CPA's, Design Build Professionals and Real Estate Professionals across the U.S. If synergies are apparent, please send me a connection request and let's see how we can work together.
Failing Forward: How One CPA Found Success in Tax Entrepreneurship
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