Christ follower | Providing comprehensive financial planning for young professionals, athletes, and HNW individuals | Tweets ≠ advice | Opinions are my own
Three of the biggest IPOs in history are lining up at once. SpaceX, Anthropic, and OpenAI are all racing toward the public markets, and the FOMO is everywhere. In this month’s edition of The Compass, we look at why the most hyped IPOs in history might not belong in your portfolio, paired with two charts that caught our eye on surging airfares amid the Iran War and a lesser-known asset class that quietly beat the S&P 500. For more: https://t.co/EF39FndZCj
A lot of taxpayers walked away from this filing season with bigger balances due than expected. Strong 2025 markets, RSU vests, and bonus income outpaced what default withholding could absorb. In the first edition of The Compass, we look at why May is the cheapest month to course-correct, paired with two charts that caught our eye on AI and a rare equity streak. For more:
https://t.co/PC7LOvSGKh
Whether it's market volatility, elite athletic performance, or the rising cost of your favorite shows, the data behind the headlines is always worth a closer look. This month's charts break down a few trends we think are worth your attention, from Wall Street to your living room. The numbers don't always make the front page, but they often tell a more complete story than the headlines do. For more: https://t.co/jeENiQ2sbd
Rory McIlroy just won The Masters and captured his second straight green jacket, a weekend that also happens to be a perfect reminder of a tax strategy named after Masters site.
The Augusta Rule could let you generate tax-free income from your own home, legally. Here's how it works:
What the Augusta Rule actually is
- Under IRC Section 280A, you can rent your home for up to 14 days per year
- That rental income is completely tax-free, you don't even report it
- It gets its name from homeowners near Augusta National who rent their homes during The Masters each year
How business owners can use it
- Your business pays you rent to use your home for legitimate business meetings
- The business deducts the expense, reducing taxable business income
- You receive the rental income completely tax-free
- Done correctly, it creates a deduction on one side with no taxable income on the other
What makes it work
- Meetings must be legitimate and well documented
- Rental rate must be reasonable and market-based
- The 14-day limit cannot be exceeded or the income becomes taxable
- Works best for S-Corp or LLC owners with regular business activity
The Augusta Rule is a legitimate, IRS-recognized strategy, but the details matter. Done right, it's one of the few ways to generate truly tax-free income.
LLC vs. S-Corp isn’t a business decision, it’s a tax decision that can save you thousands. If you have self-employment income, understanding the difference matters more than you think. Here's how:
What an LLC actually does
- It’s a legal structure, not a tax strategy
- Provides liability protection for your personal assets
- By default, income is taxed as self-employment income
What an S-Corp actually does
- It’s a tax election, not a different entity
- Allows you to split income between salary and distributions
- Can reduce self-employment taxes if structured properly
Where the tax savings come from
- LLC income is subject to full self-employment tax
- Example: On $150K of income, the full amount is exposed to SE tax
- With an S-Corp, you might pay a $100K salary and take $50K as distributions
- That $50K avoids self-employment tax, creating meaningful savings
When it actually makes sense
- Typically once net income is ~$75K–$100K+
- When tax savings outweigh added costs (payroll, filing, admin)
- When you’re consistent and profitable, not just starting out
There are many things to consider when electing a filing status with self employment income. Be sure you think through options before making decisions. https://t.co/nxN6kCNrjV
RSUs feel like a bonus, but they can quietly create major concentration risk. If a large portion of your net worth is tied to one stock, that’s a risk worth managing. Here's what you need to know if you have RSU's:
Understand what you actually own
- RSUs are taxed as income when they vest
- After vesting, they’re no different than holding company stock
- Your financial exposure can be larger than you realize
Avoid overconcentration
- Too much in one stock increases downside risk
- Your income and investments may both depend on the same company
- Diversification reduces the impact of a single bad outcome
Have a plan
- Consider selling shares as they vest
- Set target allocation limits for company stock
- Remove emotion from the decision-making process
Plan for taxes proactively
- Vesting can significantly increase your tax bill
- Coordinate sales with your broader tax strategy
- Don’t let tax hesitation override risk management
RSUs can be a powerful wealth builder if you treat them like part of a plan, not a perk. Managing the risk is just as important as earning the reward. For more: https://t.co/nxN6kCNZ9t
As income grows, so do the opportunities for smarter tax planning, but also the potential for costly mistakes.
We often see high earners doing all the right things on the surface, but still leaving significant money on the table when it comes to taxes.
Here are five common ways it happens:
1. Overloading Pre-Tax Accounts
Maxing out pre-tax accounts can be helpful, but doing it exclusively can create a future tax problem. Without tax diversification, you may end up with limited flexibility when it comes time to withdraw.
2. No Roth Strategy
Many high earners assume they’re phased out of Roth contributions and stop there. Strategies like backdoor Roth contributions or conversions can create valuable tax-free growth over time.
3. Ignoring Capital Gains Planning
Not all investment income is taxed the same. Being intentional about when and how gains are realized can meaningfully reduce your tax bill over time.
4. Not Using an HSA
An HSA is one of the few accounts that offers triple tax benefits: tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified expenses.
5. Poor Timing of Income
Bonuses, equity compensation, or large distributions can sometimes be timed more efficiently. Without planning, you may end up pushing yourself into a higher tax bracket unnecessarily.
Tax planning becomes more valuable as income increases. It’s not just about what you make, it’s about how much you keep.
For more: https://t.co/nxN6kCNZ9t
Our previous website was designed in-house (by me as an intern!). I'm certainly not the creative/ designer type and while it got the job done, we’ve given it a fresh new look.
Check out our updated site here: https://t.co/fkAtp8IlhP
With tonight’s win, @NoahRoss1011 and @nolanhodge_7 got the 99th of their careers.
That ties them with @KhamariMcgriff for all-time winningest players in UNCW history.
March Madness is all about upsets, momentum swings, and spotting the underlying trends others might miss. No Cinderella stories needed in this month’s charts- we break down a few interesting patterns, from surging ETF demand to long-term shifts in consumer spending. Sometimes the numbers tell a story that’s even more interesting than the headlines. https://t.co/7m3zyb6z45
When people plan for retirement, they usually think about the big items like housing, groceries, and travel. But in reality, there are several expenses that tend to get overlooked and they can add up over time.
Here are five retirement expenses we often see people underestimate.
1. Healthcare Costs
Even with Medicare, retirees are still responsible for premiums, supplemental insurance, prescriptions, and out-of-pocket expenses.
2. Taxes
Retirement income from IRAs, pensions, and even Social Security can all have tax implications that many people don’t fully account for.
3. Home Maintenance
Owning a home in retirement often means ongoing repairs, upgrades, and unexpected projects that can cost thousands over time.
4. Helping Family
Many retirees end up providing financial help to children or grandchildren whether it’s college support, gifts, or helping during tough times.
5. Inflation
Even modest inflation can significantly increase expenses over a 20–30 year retirement, which is why planning for rising costs is important.
Planning for retirement isn’t just about saving enough, it’s also about understanding the expenses that may show up along the way.
For more: https://t.co/nxN6kCNZ9t
Congrats to @NoahRoss1011 on being a finalist for the Nolan Richardson Award.
The definition of the heart and soul of his team, and a leader on and off the court.
March Madness is here for NCAA basketball and college athletes across the country are in the spotlight. For many, that spotlight also means new NIL opportunities and income.
The games may be chaotic this month, but your finances don’t have to be.
Here are 5 smart things every athlete should consider doing with their NIL income.
1. Set Aside Money for Taxes
Most NIL payments don’t have taxes withheld, so it’s important to save a portion of every deal so you aren’t surprised with a tax bill later.
2. Build an Emergency Fund
Athletic careers can change quickly, and having cash set aside gives you flexibility if opportunities or circumstances shift.
3. Start Investing Early
Many athletes earn meaningful income earlier than most people, which creates a huge advantage if you start investing sooner.
4. Track Your Expenses
If you’re earning NIL income, you’re essentially running a small business- keeping track of expenses throughout the year can help at tax time.
5. Surround Yourself With the Right Team
Having the right advisors, mentors, and professionals around you can help you make smarter decisions with your NIL opportunities.
NIL income can be a great opportunity, but making a few smart moves now can help ensure it benefits you long after the final buzzer.
For more: https://t.co/nxN6kCNrjV
By the time March rolls around, most people are focused on filing their taxes.
But the real value of tax season isn’t just submitting the return- it’s identifying planning opportunities for the year ahead.
Here are five of the most common tax planning misses we see this time of year:
1. Not Reviewing Your Return for Planning Opportunities
• Your tax return is one of the most valuable financial planning documents you have.
• It can reveal opportunities around deductions and income planning that often get overlooked once the return is filed.
2. Missing Prior-Year Contribution Opportunities
• Certain contributions can still be made for the prior tax year up until the April filing deadline.
• For example, IRA or Roth IRA contributions for 2025 can still be made until April 15, 2026, which can create last-minute tax savings or additional retirement contributions.
3. Overlooking the Backdoor Roth IRA Strategy
• High earners are often phased out of direct Roth IRA contributions.
• The backdoor Roth strategy remains one of the most effective ways to build tax-free retirement assets.
4. No Strategy for Capital Gains or Investment Taxes
• Many investors wait until December to think about tax loss harvesting or capital gains management.
• Reviewing realized gains early in the year gives more flexibility to plan.
5. Ignoring Withholding and Estimated Taxes for the Current Year
• A large refund or a surprise tax bill often means withholding wasn’t aligned with actual income.
• Adjusting withholding early in the year can improve cash flow and prevent surprises next April.
Tax season shouldn’t just be about looking backward.
For many households, it’s the best opportunity each year to identify smarter planning opportunities for the year ahead. For more: https://t.co/nxN6kCNrjV