John Malone, JD

John Malone, JD

Co-CEO, Anomaly CPA

John Malone is the Co-CEO of Anomaly along with Greg O'Brien, CPA. He focuses on complex client issues as well as leads the company's operations and management team. John is a multi-faceted advisor with a passion for working with entrepreneurial clients and early stage businesses as they navigate complex tax and financial issues. John understands that your business and life are intertwined, requiring a management strategy that considers the right now in conjunction with your company's financial longevity and wellbeing. John is dialed in on his clients’ futures, centering his approach around proactive and advanced tax planning. John is a Certified Tax Coach as designated by the American Institute of Certified Tax Planners. John was a 2023 40 Under 40 and has helped lead Anomaly to the #1186 ranking on the Inc5000 list.

Education

Bentley University BS Economics & Finance; Suffolk Law JD

Expertise

Tax Law; Startups

Highlight

2023 40U40

If you’d like to explore more ways to grow your businesses financial operations and tax strategies, connect with us at anomalycpa.com/connect.

Articles by John Malone, JD

Maximizing customer lifetime value: Formula, strategies, and insights
Maximizing customer lifetime value: Formula, strategies, and insights
Learn what customer lifetime value (CLV) is, how to calculate it, and strategies to boost retention and profitability for your business.
5 ways small business owners can reduce taxes in 2025
5 ways small business owners can reduce taxes in 2025
Learn five effective strategies on how to reduce business taxes through year-round planning. Optimize your entity structure, deductions, and retirement options to save more money.
Preparing for an IRS business tax audit
Preparing for an IRS business tax audit
An IRS business tax audit reviews a company's tax return and financial records for accuracy, triggered by random selection or risk factors. Businesses can prepare by understanding triggers, maintaining proper records, and seeking professional representation to navigate the audit process smoothly. Learn strategies to minimize audit risk and handle audits effectively with our comprehensive guide.
Founders guide to navigating secondary transactions
Founders guide to navigating secondary transactions
Explore the mechanics, benefits, and complexities of secondary transactions for startup founders seeking liquidity. Understand legal frameworks, valuation challenges, and tax implications to navigate these transactions effectively. This guide helps founders align with investors for mutual benefit while maintaining strategic cap table management.
Don’t be surprised by state excise taxes
Don’t be surprised by state excise taxes
Unlock strategies to manage state excise taxes effectively with our detailed guide. Learn how different business structures impact tax obligations and explore state-specific examples such as Massachusetts, Tennessee, Ohio, and Washington. Equip yourself with the knowledge to enhance your financial planning and prevent unexpected tax liabilities as you start and scale your business.
How profits interest equity grants work
How profits interest equity grants work
Dive into the benefits of profits interests as a strategic equity compensation tool for LLCs. Understand how profits interests work, their tax advantages, and the legal considerations. Ideal for founders and early-stage business owners looking to attract top talent and align employee goals with long-term company success.