Your Personal Tax Strategist to Supercharge Your Existing Financial Team
The Premier Tax Strategist to Supercharge Your Existing Financial Team
Who Needs a Tax Strategist?
Tax-saving strategies are needed when you are in one or more of these circumstances:
- High-Income Earners - Paying more than $100,000 in tax annually and need to reduce your taxable income.
- Highly-Appreciated Asset Sales - A desire to keep more of the proceeds from the sale of a business, crypto, appreciated stock, or other asset.
- Lumpy Income Earners – Settlement or deferred compensation payouts that can create very high single-year tax headwinds.
An effective tax planning strategy can help reduce taxes regardless of stock market or real estate performance. These tax-saving strategies allow you to save more as you earn more.
Do you want to learn about the solutions they use and seamlessly integrate those into your existing plan?






Why Do You Need a Tax Strategist?
Tax planning services focus on lowering your overall tax rate. For example, if you are in the top bracket, you’ll pay the federal government 37% of your income. If you have a state income tax, that number goes higher. Without any planning, most Americans earning over $250,000 are slated to pay 40% - 55% to the government. We employ legal and ethical solutions to both reduce your taxable income while growing your wealth.
What is a Tax Planning Strategy?

A tax planning strategy is a method of managing potential tax liability in the current year versus the following year. Many options can be explored during the current year, such as maximizing deductions and credits, selecting tax-advantaged investments, and timing income and expenses in a way that suits your financial plan.
Simply put, tax planning is like looking through your front windshield while thinking about taxes so that you can navigate the challenges ahead. In contrast, accounting involves looking through the rearview mirror to see what has happened in the past without the ability to make changes.
What are the Characteristics of Tax Planning?

Tax planning has a risk/reward spectrum, like investing in stocks and bonds. An appropriate strategy has the following characteristics.
- Understanding client goals such as the desire to impact future family generations, charitable inclination, and business ownership.
- Knowledge of the personal and or business income and potential capital gains.
- Commitment level – one year or multiple years.
- With this information, plans can be crafted to maximize future goals tax-efficiently and compliantly.
Tax Planning Strategy Experience

Who We Are
Erik Flegal
Erik began his financial services career while still in college at the University of California – Los Angeles. After training advisors and updating the financial interface and planning systems, he managed the Rolling Hills and Glendale, CA branches of a Morgan Stanley predecessor firm.
His desire to provide his clients with the best solutions motivated him to create a fiduciary multi-family office for high net worth families.
Erik has a passion for education. A frequent speaker at local offices and events, Erik was a member of the faculty at UCLA Extension where he taught classes on the Art and Science of Investments and the Fundamentals of Investing for the Financial Certificate program.
Erik is the founder of Red Carpet Charleston. This is an invitation-only event series for new residents to quickly integrate into the fabric of Charleston – both professionally and personally. Focusing on high level executives and decision makers who are new to the area, the series is designed to provide meaningful introductions, connections and recommendations with established leaders in the community.
In addition to the BA in English he earned at UCLA, Erik also received an MBA from University of Southern California. He was a member of the UCLA Volleyball team and the Youth Olympic Volleyball team – winning a Gold Medal during international competition in Canada. He’s also an amateur magician and a member of the Academy of Magical Arts in Hollywood, CA. Erik resides in Mount Pleasant, SC with his wife Hollyann, two daughters, Savannah and Annabelle, and two sons, Joshua and Jonathan.
Matt Dailey
Matthew is a dynamic professional with a diverse background and a passion for serving others. With 13 years of experience as a dedicated school administrator and principal, he nurtured educational environments that fostered growth, learning, and student success. Prior to his career in education, Matthew enjoyed an illustrious career as a professional baseball player, honing his skills and embodying the spirit of teamwork and determination.
Recognizing the importance of financial planning and security, Matthew transitioned into a role leading the integration of professionals and services to clients at Family Fortune Financial. He provides invaluable guidance to individuals and families seeking to create a solid financial. His expertise in this field ensured that clients were equipped with the necessary tools and strategies to navigate their retirement with confidence.
With a rich and diverse professional background, Matthew brings a unique perspective and a commitment to exceptional service in everything he does. Whether it’s leading educational institutions, empowering clients towards a secure future so they can pursue their own passions, Matthew consistently demonstrates dedication, leadership, and a drive to make a positive impact. Matt lives in Summerville, SC with his wife Elizabeth, three daughters and Harley the family dog.
Jake Graefe
Jake is a Senior Financial Planner with extensive experience collaborating with financial advising teams nationwide. He holds multiple industry certifications, including Series 66, Series 7, SIE, and Health and Life Insurance, showcasing his deep expertise.
Jake earned a Bachelor’s degree in Mechanical Engineering and a Master’s in Business Administration from Grand Canyon University. Initially, he began his career in the aerospace sector but later transitioned to financial advising to better connect with clients and make a meaningful impact on their financial and personal goals.
Outside of his professional life, Jake cherishes time spent with family and friends. He enjoys a variety of activities, including golf, volleyball, and skiing, and loves creating lasting memories with his wife, Emily.
Jeffrey Smith
Jeffrey is Family Fortune Financial LLC’s Chief Compliance Officer. Jeffrey is a highly-experienced securities lawyer, chief compliance officer, and business attorney with over 23 years of experience strengthening the legal and compliance functions of investment advisers, broker-dealers, and investment vehicles.
He has also represented companies at all stages of maturity with their capital and debt-raising efforts via private offerings and public offerings. He has also served as Chief Legal Officer and Chief Compliance Officer for NorthRock Partners LLC and Virtue Capital Management LLC; Chief Executive Officer and Co-founder of RIA Compliance Firm LLC, and Founder and Managing Attorney for LawVisory.
He previously served as Chief Compliance Officer of Griffin Capital Company LLC and Research Affiliates LLC, where he also served as Assistant General Counsel.
Amanda North
With over 14 years of experience in the insurance industry, Amanda has strong expertise in underwriting, case management, and client services. She also has a giant rolodex. Her focus on creating innovative practices and workflows is a game changer in the complex life insurance world.
Amanda’s passion for making process of life insurance simple and white glove made her a natural part of the team. She’s compassionate and thorough by nature, continually leaving clients impressed by her attitude and ability to get things done.
Amanda graduated from Bay Path University with a Bachelor’s in Business Administration and MBA in Entrepreneurial Thinking and Innovative Practices. She currently lives in Connecticut with her husband and two children.
Karch Perkins
Karch is a Senior Paraplanner and Financial Advisor at Legacy Private Wealth Partners, with more than three years of experience in the industry. He’s passionate about helping people achieve their financial goals and committed to providing personalized service and sound financial advice.
Karch holds a Series 66, Series 7, and SIE® license, and an undergraduate degree in philosophy, accounting, and communication from University of Colorado Boulder. He previously worked at Fidelity Investments as a Client Service Representative.
Outside of work, he enjoys working out, spending time with friends and family, and playing or watching sports. Karch also enjoys volunteering in his community.

Our Process
Our tax strategists add simplicity, not complexity.
- Discovery - Where are you now?
- Design - Customize your tax savings plan
- Implement - Put your strategy to work
- Year-End Customization - Dial year-end numbers up or down
- Tax Season Oversight - Help with K1s and questions
Tax Planning Services FAQs
Real World Case Study
A tax strategist can add significant wealth to an estate over time when tax-saving strategies are deployed correctly. This case is a sample of how one family reduced their taxes to single digits.
- Client Income - $4,000,000, with an additional $750,000 in long-term capital gains.
- Initial Tax Bill - $1,991,100.
- Savings - $1,345,582.
- Client Commissions - $168,500.
Bottom Line Impact - Tax savings of $1,536,082 or a new effective tax rate of 9.58% of income and gains for the year. Additionally, the client kept all $3 million that they invested in these strategies growing for their future benefit.
A South Carolina couple filing jointly makes $4 million in annual income ($3 million from various business interests + an additional $1 million from rental income). They also had a $750,000 long-term capital gain from a business sale.
Their annual estimated tax would be $1,991,100 with no tax planning ($1,783,200 Federal/FICA + $207,900 State).

This client used three tax-saving strategies to reduce taxes. All three follow the IRS code.
- Intangible Drilling Cost (IDC) Tax Deductions
Invested $1,600,000 into Oil and Gas Drilling Ventures.
To be clear, this is not “wildcatting” or looking for oil. This is simply drilling in areas where oil is known to exist, often in tandem with major oil companies in an ESG-compliant fashion. The Intangible Drilling Cost (IDC) Tax Deduction has been codified since 1913. The intangible expenditures of drilling (labor, chemicals, mud, grease, etc.) are usually about (65 to 80%) of the cost of a well. These expenditures are considered “Intangible Drilling Cost (IDC),” which is 100% deductible during the first year. For example, a $100,000 investment could yield up to $80,000 in IDC tax deductions during the venture's first year. These deductions are available in the year the money was invested, even if the well does not start drilling until March 31 following the capital contribution. (See Section 263 of the Tax Code.)
In addition to the tax benefit, the investor would also be eligible to participate in the economics of the drilling project, which has historically yielded between 100% and 200% cash on cash returns over the last 40 years.
As a tax strategist group, we worked with an independent accounting firm to determine the amount and impact on each investor. In this example, we would invest $1,600,000 in the Drilling Strategy.
- Opportunity Zones
Invested $750,000 to defer all long-term capital gains through 2026.
Opportunity Zones were created in the 2017 Tax Cuts and Jobs Act that meet one of three criteria under the definition of “low-income community” in Internal Revenue Code Section 45D(e). You can only invest with capital gains, but the benefit of investing in opportunity zones is significant. Capital gains are deferred through 2026, and if held for ten years, all investment gains are tax-free.
In this case, the clients had a business sale that netted $750,000 in long-term capital gains. Regardless of the initial investment, the gains are the only way to open the door to an opportunity zone. Most opportunity zone investments pay an annual dividend and have a ten-year growth plan.
In this case, we invested $750,000 into the Opportunity Zone Investment and deferred the entirety of the capital gain through 2026.
- Enterprise Risk Insurance Policies
Invested $1,000,000 to offset business liability and deduct the entire amount.
Because these clients are business owners, they can use Enterprise Risk Insurance to insure their low-frequency, high-severity items. Through shared risk, the claims history is around 2% annually. We work with a licensed and regulated International Insurer in the U.S. Commonwealth of Puerto Rico. It is regulated by Puerto Rico's Office of the Insurance Commissioner, an accredited member of the National Association of Insurance Commissioners (NAIC), and the Asociación de Supervisors de Seguros de Latinoamérica (Assal). Act 399 and Act 400 in Chapter 61 of the Puerto Rico Insurance Code were adopted to establish the basis for the International Insurance Center (IIC), which provides a competitive environment for insurers and reinsurers to cover risks outside of Puerto Rico under a secure and flexible regulatory system, with attractive tax benefits.
We work with an outside actuary to dial in the premiums and coverage. This is based on the companies' gross revenues. Once determined, the entire premium is categorized as an ordinary and necessary business expense. It can be invested and grow tax-free until removed, which is at the policyholder's discretion.
In this case, the premium we’d recommend would be $1 million.
Bottom Line Impact
- The initial tax bill was $1,991,100.
- Their savings was $1,345,582.
- The commissions returned to the client were $168,500.
The bottom line impact was a savings of $1,536,082 or a new effective tax rate of 9.58% of income and gains for the year. Additionally, the client kept all the $3 million they invested in these tax-saving strategies growing for their future benefit.
Grown at a 6% rate, this $1.5 million would be worth $2.75 million in 10 years (or $3.68 million in 15 years).





