
#402: Tax Mitigation Strategies: Keeping More of What You Earn with Roger Roundy
08/29/24 • 54 min
In this episode of Independence by DesignTM, Ryan Tansom sits down with Roger Roundy, a tax mitigation strategist with a unique approach to helping business owners keep more of their hard-earned money. Roger explains the three phases of wealth—accumulation, preservation, and distribution—and how each phase requires different tax mitigation strategies to maximize wealth. He emphasizes the importance of understanding the tax code as a set of incentives designed to encourage certain behaviors rather than something to be feared. Roger argues that when properly understood, the tax code allows business owners to legally and ethically partner with the government to reduce their tax liabilities, all while staying in compliance with audit protection.
Watch on YouTube
Throughout the episode, Roger shares his journey of becoming a "tax architect," detailing how his firm helps small to mid-sized businesses utilize the same tax-saving techniques employed by Fortune 500 companies. Listeners will gain insights into various tax mitigation strategies, the distinction between tax preparation and tax strategy, and how to proactively manage taxes throughout the wealth-building journey. Roger also discusses why his solutions are audit-proof, eliminate any grey areas, and show how business owners can leverage a team of advisors to optimize their financial strategy.
Roger Roundy is the CEO of Strategic Associates a Risk Mitigation firm focused primarily on the education and implementation of tax mitigation strategies. Throughout his years of risk management and tax mitigation services, Roger has helped 100’s of business owners and individuals find solutions to protect their incomes from the wealth-eroding factors of risk and taxes. As the CEO and Director of Operations for Strategic Associates, Roger thrives on providing value using innovative but sound tax mitigation strategies to help his clients reduce their tax liability and provide options for properly positioning those savings. "Work hard, play harder, and provide opportunities for others to do the same" has been his M.O. during his business life. Roger has been married for 24 years and is the father to 5 wonderful children. He is an avid outdoorsman and loves to spend any spare time he can find, either biking, skiing, snowmobiling, or hunting. Life is busy, and a passion for working with other successful business owners has directed his path to tax mitigation and the extreme value and opportunity it provides to his clients.[Text Wrapping Break]
Chapters:
- (00:00) Introduction and Background, Roger Roundy’s Journey to Becoming a Tax Architect
- (07:20) The Role of CPAs vs. Tax Consultants, Understanding Tax Mitigation and Its Importance
- (21:00) Tax Planning and Strategy vs. Tax Preparation
- (32:00) The Three Phases of Wealth and Tax Mitigation
- (35:00) Googling Tax Information
- (38:15) How to Proactively Manage Your Taxes
- (41:17) Managing your wealth and cash flow, Partnering with the Government, Understanding the Tax Code
- (47:08) Advice for Business Owners on Reducing Tax Liabilities, Risk Management
- (48:36) Final Thoughts and Call to Action
Ryan Tansom is a seasoned entrepreneur, speaker, and the founder of Independence by DesignTM, a transformative ownership framework for growth-oriented business owners. After turning around and selling his family business in an eight-figure exit, Ryan spent over a decade dissecting the lessons learned from his journey. His mission is to help other business owners avoid the pitfalls he encountered by providing them with the tools and knowledge to align their business operations with their personal and financial goals.
With a deep understanding of the challenges faced by owner-operators, Ryan developed Independence by DesignTM to empower owner-operators to create sustainable cash flow, grow their company’s equity value, and achieve true independence. He has shared his insights on hundreds of stages, including Vistage, EO, and industry associations, and has reached over 500,000 listeners through his podcast.
Ryan is passionate about helping business owners get unstuck from the day-to-day grind and design a business that serves their life, not the other way around.
Resources:
Strategic Associates https://www.strategicag.net/
Book a Tax Strategy Call with Roger
Roger Roundy LInkedIn https://www.linkedin.com/in/roger-roundy-tax-mitigation/
Independence by DesignTM Owner’s Workshop
In this episode of Independence by DesignTM, Ryan Tansom sits down with Roger Roundy, a tax mitigation strategist with a unique approach to helping business owners keep more of their hard-earned money. Roger explains the three phases of wealth—accumulation, preservation, and distribution—and how each phase requires different tax mitigation strategies to maximize wealth. He emphasizes the importance of understanding the tax code as a set of incentives designed to encourage certain behaviors rather than something to be feared. Roger argues that when properly understood, the tax code allows business owners to legally and ethically partner with the government to reduce their tax liabilities, all while staying in compliance with audit protection.
Watch on YouTube
Throughout the episode, Roger shares his journey of becoming a "tax architect," detailing how his firm helps small to mid-sized businesses utilize the same tax-saving techniques employed by Fortune 500 companies. Listeners will gain insights into various tax mitigation strategies, the distinction between tax preparation and tax strategy, and how to proactively manage taxes throughout the wealth-building journey. Roger also discusses why his solutions are audit-proof, eliminate any grey areas, and show how business owners can leverage a team of advisors to optimize their financial strategy.
Roger Roundy is the CEO of Strategic Associates a Risk Mitigation firm focused primarily on the education and implementation of tax mitigation strategies. Throughout his years of risk management and tax mitigation services, Roger has helped 100’s of business owners and individuals find solutions to protect their incomes from the wealth-eroding factors of risk and taxes. As the CEO and Director of Operations for Strategic Associates, Roger thrives on providing value using innovative but sound tax mitigation strategies to help his clients reduce their tax liability and provide options for properly positioning those savings. "Work hard, play harder, and provide opportunities for others to do the same" has been his M.O. during his business life. Roger has been married for 24 years and is the father to 5 wonderful children. He is an avid outdoorsman and loves to spend any spare time he can find, either biking, skiing, snowmobiling, or hunting. Life is busy, and a passion for working with other successful business owners has directed his path to tax mitigation and the extreme value and opportunity it provides to his clients.[Text Wrapping Break]
Chapters:
- (00:00) Introduction and Background, Roger Roundy’s Journey to Becoming a Tax Architect
- (07:20) The Role of CPAs vs. Tax Consultants, Understanding Tax Mitigation and Its Importance
- (21:00) Tax Planning and Strategy vs. Tax Preparation
- (32:00) The Three Phases of Wealth and Tax Mitigation
- (35:00) Googling Tax Information
- (38:15) How to Proactively Manage Your Taxes
- (41:17) Managing your wealth and cash flow, Partnering with the Government, Understanding the Tax Code
- (47:08) Advice for Business Owners on Reducing Tax Liabilities, Risk Management
- (48:36) Final Thoughts and Call to Action
Ryan Tansom is a seasoned entrepreneur, speaker, and the founder of Independence by DesignTM, a transformative ownership framework for growth-oriented business owners. After turning around and selling his family business in an eight-figure exit, Ryan spent over a decade dissecting the lessons learned from his journey. His mission is to help other business owners avoid the pitfalls he encountered by providing them with the tools and knowledge to align their business operations with their personal and financial goals.
With a deep understanding of the challenges faced by owner-operators, Ryan developed Independence by DesignTM to empower owner-operators to create sustainable cash flow, grow their company’s equity value, and achieve true independence. He has shared his insights on hundreds of stages, including Vistage, EO, and industry associations, and has reached over 500,000 listeners through his podcast.
Ryan is passionate about helping business owners get unstuck from the day-to-day grind and design a business that serves their life, not the other way around.
Resources:
Strategic Associates https://www.strategicag.net/
Book a Tax Strategy Call with Roger
Roger Roundy LInkedIn https://www.linkedin.com/in/roger-roundy-tax-mitigation/
Independence by DesignTM Owner’s Workshop
Previous Episode

#401: Discovering the Truth About Economics & Money: Joe Brown on Inflation, Investments, and Independence
In this inaugural episode of the Independence by DesignTM podcast, Ryan Tansom sits down with Joe Brown, founder of Heresy Financial, to dive deep into the intricacies of the economy and financial systems. Driven by personal experiences and a relentless curiosity, Joe explores the mainstream financial narratives and advocates for a deeper understanding of economic fundamentals. He underscores the importance of aligning financial decisions with personal values and addressing root causes of economic issues, rather than merely treating symptoms.
Watch on YouTube
The discussion spans critical topics like the effects of money printing, the escalating costs of education and healthcare, and the quest for financial freedom. Joe and Ryan also dissect the evolution of money as a debt system, the value of time, and strategies for managing wealth amid inflation and taxes. They provide practical insights into business ownership, portfolio diversification, and the challenges posed by government bond refinancing and its impact on regional banks. Tune in to gain valuable perspectives on mastering your financial future and understanding the system that shapes it.
Key Takeaways:
- Aligning one's values with their financial decisions is crucial for personal fulfillment and moral integrity.
- Understanding the root causes of economic problems is more important than focusing on symptoms.
- Education and individual decision-making play a significant role in improving one's financial situation.
- Money printing, rising costs of education and healthcare, and the erosion of financial freedom are key issues in the current economic landscape. Money has evolved over time from a debt system primarily.
- Time is the most valuable resource for individuals, but it is also the most replaceable thing to others.
- Starting a business allows individuals to provide value that is not denominated in their time and can lead to escaping the limitations of trading time for money.
- Diversifying investments across savings, business, and income-producing assets can help protect wealth and provide stability.
- Understanding how the financial system works and taking control of one's wealth is crucial in navigating the challenges and uncertainties of the future.
In This Episode:
- (00:00) Introduction and Background - Joe Brown of Heresy Financial
- (04:45) Joe's Journey into Understanding the Economy
- (10:00) The Curiosity to Understand the Economic Cycle
- (13:13) Stepping Stones to Understanding the Economic Cycle
- (18:00) Aligning Work with Your Values
- (23:00) Questioning the Narrative and Seeking Understanding
- (26:00) Starting the Conversation about the Economy, Silent QE by Commercial Banks
- (29:30) The Historical Perspective on Money and Trust, What happened in 1971?
- (33:15) Analyzing Economic Narratives and Policies
- (42:00) The Value of Time and Escaping the Time-for-Money Trap
- (44:55) Starting a Business, Owner/Operators and Cash Evaluation
- (47:56) Case Studies, Diversifying Investments, Protecting and Growing Wealth
- (59:00) Looking Forward, Navigating Challenges and Uncertainties
- Share, like and subscribe to hear all of our informative upcoming episodes!
About Ryan Tansom/Independence by Design:
Ryan Tansom, host of the Independence by DesignTM podcast, is dedicated to empowering business owner-operators to achieve true independence. After transforming his family's $21 million business and selling it for eight figures in 2014, Ryan embarked on a decade-long journey to refine business ownership strategies. His experiences led him to create the Independence by DesignTM Framework, designed to help owners build sustainable cash flow, increase equity value, and escape daily operational grind. Through the podcast, speaking engagements, and coaching program, Ryan shares his expertise to help others thrive in their business ventures.
Resources:
Next Episode

#403: Cash Flow Broke and Balance Sheet Rich with Eric Roman
In this episode of Independence by DesignTM, Ryan Tansom is joined by Eric Roman, a former dentist turned entrepreneur and business coach, who shares his powerful story of building and exiting a successful dental service organization (DSO) worth $40 million. Despite his company’s impressive valuation, Eric felt cash flow broke and balance sheet rich, struggling with significant personal life issues. He believed the only way to solve his problems was to sell the business and pull the ripcord. However, after the exit, he realized that selling the business didn’t resolve the deeper issues in his personal life.
Watch on YouTube
Eric dives into the challenges of managing growth, the impact of business on personal life, and how implementing the Entrepreneurial Operating System (EOS) transformed his business. He also reflects on how he wishes he had an ownership framework like Independence by DesignTM to guide him on the ownership side of decision-making, which could have provided the clarity he needed beyond the operational insights of EOS. Eric discusses the importance of having a personal operating system and how the One Life System helps entrepreneurs achieve both professional and personal success. Throughout the episode, Eric offers insights into balancing business demands with family life, the significance of personal clarity, and the necessity of having a support system to navigate the entrepreneurial journey.
Eric Roman has over a decade of experience running high-powered, multi-location dental companies. From inception through exit, Eric understands all facets of what it takes to build transformational companies and, most importantly, personal joy. His breadth of expertise covers topics such as Executive team development, EOS (The Entrepreneurial Operating System), Culture Development, Managing Millennial and Post-Millennial Workforces, Developing High-Performing Associate Dentists, Work-Life Harmony, Personal Performance Habits, and much more. However, Eric's value isn't limited to his accomplishments: He has a unique ability to inspire and empower others to live abundant, impactful lives.
Chapters:
- (00:00) Eric Roman's journey scaling his dental practice to $40M valuation
- (06:49) EOS in Transforming Business Operations, Balancing Business Success with Personal Fulfillment
- (14:00) Ownership Goals, Trade-Offs Between Immediate Cashflow And Long-Term Equity Growth, Personal Scorecards And Understanding Life Experience Costs
- (16:00) Building “a $100 Million company,” Managing Control And Expectations To Reduce Anxiety And Stress
- (24:39) Navigating the Challenges of Business Growth and Personal Life
- (36:15) Finding a “System”, The Power of Community and Support Systems for Entrepreneurs
- (40:33) Overcoming Identity Crises and Finding Meaning Beyond Business, Transition From Success To Significance
- (55:31) The One Life System: A Framework for Personal and Family Success
- (1:05:02) Final Thoughts and Call to Action
Ryan Tansom is a seasoned entrepreneur, speaker, and the founder of Independence by DesignTM, a transformative ownership framework for growth-oriented business owners. After turning around and selling his family business in an eight-figure exit, Ryan spent over a decade dissecting the lessons learned from his journey. His mission is to help other business owners avoid the pitfalls he encountered by providing them with the tools and knowledge to align their business operations with their personal and financial goals.
With a deep understanding of the challenges faced by owner-operators, Ryan developed Independence by DesignTM to empower owner-operators to create sustainable cash flow, grow their company’s equity value, and achieve true independence. He has shared his insights on hundreds of stages, including Vistage, EO, and industry associations, and has reached over 500,000 listeners through his podcast.
Ryan is passionate about helping business owners get unstuck from the day-to-day grind and design a business that serves their life, not the other way around.
Resources:
Eric Roman LinkedIn https://www.linkedin.com/in/drericjroman/
One Life System - A system designed to help entrepreneurs balance their professional and personal lives. https://1life.drericjroman.com/
Book: "The E-Myth Revisited" by Michael E. Gerber
Book: "Traction" by Gino Wickman
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