The Aggressive Investor

Financial Planning Strategies

Profile Overview

This Investor is typically older than 45 years old with a net worth between 1-9 million dollars. They are sharp, have a high income, and excellent financial acumen. They are well on their way to financial independence with multiple streams of income. These investors are business owners or executives in large companies. This investor enjoys many perks, including vehicles, gas cards, cell phones, pensions, profit sharing, and stock options. This Investor has spent significant time studying personal finance and has met with CPA’s, tax, and financial planners. This person has a mortgage but could pay it off if they wanted to. When the home is paid off, they set up a HELOC to use for emergencies or to jump on deals. It is common for this Investor to have a personal corporation used to hold investments mitigating investment risk and taxes. The aggressive investors have multiple retirement accounts, maxing them out every year. (401K. IRA, HSA, defined benefit plan) Most have a detailed budget and use or to track assets.

Most importantly, this person has a working knowledge of leverage, diversification, and passive income. They often have mentors and trusted advisers, guiding them through business and financial decisions. This person has typically developed an abundance mindset valuing time, education, and helping others.

“To maximize your net worth, you have to get into a high paying profession or own profitable business. Aggressive investors can either use a Robo-advisor or engage a low fee financial adviser. The advantage of the low fee financial adviser is the coaching and mentoring that comes with the engagement. Aggressive investors begin to focus less on the traditional 401K’s and IRA’s and look at where the returns are higher, and taxes are limited. These Investors can become very wealthy over time.”

Suggested Plan

    1. Build an emergency fund with 6-12 months worth of living expenses.
    2. Pay off all debts outside of your mortgage.
      • Decision: Pay off your low-interest mortgage or invest the money. Open a HELOC if you decide to pay off the mortgage.
    3. Aggressive investing (make it automatic).
      • Max out your HSA, 401K OR if you own a business- SEP IRA / SIMPLE IRA.
      • Strongly consider a Roth 401K if available.
      • Take full advantage of any pension, profit-sharing and stock options
      • Max out your Roth or Traditional IRA (use the backdoor Roth strategy if needed)
      • Consider a 529 plan to fund children’s college
      • Brokerage account- Increase your automatic monthly contributions. Decide if you want to continue using an index strategy,  Robo-advisor, or if it’s time to engage with a low fee financial advisor.
      • Explore IUL or Whole life insurance plans.

Entrepreneurs and business owners should consider #4.

4. Personal LLC Strategy: Consult with your CPA and attorney about setting up a personal corporation to hold additional investments. Options could include:

    • Debt Financing- lend money to businesses, builders, developers, individuals.
    • Equity in businesses
    • Real Estate
      • Direct commercial or residential portfolio
      • Passive- Crowdfunding equity or debt real estate deals
      • Land development
    • Alternative Investments
      • Life settlements funds
      • Litigation finance funds
      • Private Equity funds
      • Websites / Blogs / Books

Please consult with your CPA or attorney before making specific investments.


  • Maximizing your income is the most critical step to growing your wealth
  • Automate your investing- Step 3 needs to fund automatically. (pay yourself first)
  • Don’t try and time the market or pick individual stocks.
  • Use a budget- see where your money is going and pay yourself first.
  • Invest in things you understand and start as young as possible. (compounding interest)
  • Get a term life insurance policy if you have dependents
  • Set up your will and Living trusts
  • If you make too much for a Roth IRA. Use the backdoor Roth IRA strategy.
  • Meet with an attorney and set up your living Will and Trusts.
  • Create an “If I die”spreadsheet- list of all accounts with points of contact.
  • Physicians- study up on student loan forgiveness programs
  • Don’t blow chunks- Invest the big chunks of cash that come your way.
  • If you sell a business, don’t invest all your money in another start-up and assume you will hit it big again.  Move to safe money strategies.

Tax Strategies

  • It is very important you hire a tax professional at this stage
  • Understand standard deductions vs. itemized deductions- use whichever is better in a particular year. Maximize your tax deductions/ deferrals. Basics include mortgage interest, property taxes, child tax credit, charitable contributions, 401K, HSA, FSA, 529, Municipal bonds, Roth IRA, IUL Section 179.
  • Donate appreciated stock to tithe. (most churches accept this form of donation, and it will save you 20-24% on capital gains)
  • Explore opportunity zones- a new program that allows real estate investors to defer gains.