Case Studies
Real Voices. Real Results.
Case Study #1
Lost On Where to Start
Challenge:
Genevieve came to me cranking it in her business but not sure exactly if she was making any money. In the past, she wrote out her expenses on a legal pad, gave this and her income info to her husband to take to the accountant, and hoped for the best. She had no idea if her business was making money at the end of the year or if it was doing better year over year, other than the amounts she saw in her bank account. However, even that was messy because her business income and expenses were coming into and out of her personal bank account.
What We Did:
- Set up a dedicated business bank account and credit card.
- Helped her get an EIN and walked her through how her business numbers show up on tax returns.
- Created a roadmap so she could finally track her income and expenses properly.
Result:
- She now knows exactly where her business stands financially.
- She can make informed decisions on growth.
- Financial discussions with her family are now clearer and more productive.
Case Study #2
The Side Hustle Wasn’t the Problem
Challenge:
Kira came to me in December. She has a W-2 job, making low 6 figures each year. She also has a side hustle company that she is trying to grow. She works with an accountant but the accountant doesn’t give advice; he simply processes the information she provides. She keeps owing large sums when filing her taxes each year and figures that her business income is causing the problem. As a result, she keeps buying equipment and materials to neutralize her business profits but realizes that this approach isn’t sustainable.
What We Did:
A deep dive into her finances revealed the real problem—her W-2 withholdings were too low, not her business profits. We:
- Built a plan to catch up on what she owed.
- Adjusted her W-2 withholdings to prevent future surprises.
- Helped her ask the right questions to her accountant and provided referrals to better-suited professionals.
Result:
- No more tax season surprises.
- She knows exactly what’s going on with her finances.
- She can grow her business without the constant stress of unexpected tax bills.
Case Study #3
The self-employed professional with income but no retirement savings or idea where to start
Challenge:
Sunny had been self-employed for years, making good money but figuring things out as she went when it came to taxes and bookkeeping. Sometimes she used a tax professional, sometimes she didn’t. Now that her business had stabilized, she wanted to start saving for retirement but had no idea where to begin—and previous experiences with financial advisors talking down to her had left her wary of asking for help.
What We Did:
- Evaluated her income and business structure.
- Compared three retirement plan options that offered the most flexibility and tax advantages.
- Walked her through where to open an account and what questions to ask.
Result:
- Sunny finally started saving for retirement.
- She’s now keeping several thousand dollars in tax savings each year.
- She has a clear plan in place—no more guesswork.
Case Study #4
The (Almost) Lost $250,000 in Capital Losses
Challenge:
Bob and Lana had used an accountant for years, but Bob decided to try DIY tax filing. When reviewing his past filings, I discovered that he had completely missed carrying forward over $250,000 in capital losses—something the IRS doesn’t track for you.
What We Did:
- Amended past returns to restore the missing losses.
- Strategically applied them against future gains to maximize tax savings.
Result:
- Saved approximately $50,000 in federal and state taxes.
- Made sure they never missed out on tax savings like this again.
Case Study #5
Maximizing Inheritance and Investment Assets: How One Couple Saved $40K in Taxes on Their $200K Down Payment
Challenge:
Tanner and Mackenzie were in a strong financial position—Tanner was an early employee at a successful startup, and Mackenzie owned her own business. However, when Mackenzie’s father passed away unexpectedly, she inherited a low six-figure sum entirely in retirement funds.
With home prices rising in their high-cost area, they needed $200,000 for a down payment on their first home. They had a mix of investments, cash savings, and inherited retirement accounts but weren’t sure how to access the funds in the most tax-efficient way. They wanted to minimize penalties and long-term financial consequences while preserving as much of their assets as possible.
What We Did:
- Reviewed their tax brackets, both current and projected over the next 3–5 years, to determine the best timing for withdrawals.
- Evaluated different asset liquidation strategies to identify which would have the lowest tax impact.
- Recommended a plan to withdraw from investments instead of touching the inherited retirement accounts, ensuring they avoided penalties and unnecessary tax liabilities.
Result:
- Over $40,000 saved in taxes from a single strategy session.
- A clear financial roadmap that allowed them to secure their down payment while keeping their long-term investment goals intact.
- Confidence in their decision, knowing they minimized their tax exposure and set themselves up for future financial success.
Case Study #6
Retirement Relocation: What Makes Financial Sense?
Challenge:
Carly and Bill were debating whether to stay in Connecticut or move to Vermont, New Hampshire, New York, or Virginia. They wanted to consider cost of living, taxes, and overall lifestyle factors.
What We Did:
- Conducted a full analysis of how their retirement income would be taxed in each state.
- Compared property taxes, insurance costs, and overall cost of living.
Result:
- They realized staying in Connecticut was the best financial move.
- Avoided expensive moving costs for a change that wouldn’t have benefitted them.
Case Study #7
When to Close a Business Because It Isn’t Working Anymore
Challenge:
This one is a personal case – colleagues and I entered into a business together to build a hand-held reference guide to tax professionals called FingerTip Tax Facts. It was a super handy, compact and useful reference guide at a low price point and easy to grab while looking for a piece of information during tax season. It was a great product, but we ran into significant challenges:
- We lacked the time and marketing resources to scale.
- Each partner was in a different state, making sales tax compliance a nightmare.
- Our audience was small and fragmented.
What We Did:
After three years, we had an honest conversation: Was this worth the effort? The answer was no.
Result:
- We made the strategic decision to close the business before losing more money.
- No hard feelings—just a smart financial move.
