Sin City CFO

Sin City CFO Tax Saving Strategies , Bookkeeping & Virtual CFO for Online Business Owners

09/17/2026

A Safe Harbor 401k requires more than just choosing a retirement plan.

Business owners need time to complete plan documents, payroll integration, employee eligibility setup, and plan administration before the October 1 deadline.

Starting early helps ensure your 401k plan setup is completed correctly and your business is prepared to offer retirement benefits without last-minute issues.

If you’re considering a Safe Harbor 401k for your company, review your timeline with your retirement plan provider or advisor.

Related: Safe Harbor 401k, 401k plan setup, small business retirement plans, business owner retirement, employee benefits, payroll integration, retirement plan administration, 401k deadlines, business tax planning, IRS retirement rules

09/16/2026

Running your own S Corp payroll on Gusto or ADP?

If your Solo 401(k) employee deferrals aren't reported in Box 12 of your W-2 by January 31st, the IRS won't count your deduction.

As an S Corp owner, you are both the employer and the employee. While the cash funding deadline for your employer contribution can extend into the fall, your employee elective deferrals must be properly processed through payroll and recorded on your W-2 by January 31st.

When you report your 401(k) deferrals correctly on your payroll platform:

Your W-2 is Generated: Your traditional deferrals reduce your Box 1 taxable wages while appearing in Box 12 (Code D).

The SSA & IRS Sync: Your business files the W-2 with the Social Security Administration, which automatically shares that data with the IRS.

Your Tax Return Matches: Your CPA uses that W-2 to prepare your individual Form 1040. If Box 12 is blank, your personal CPA cannot retroactively deduct employee 401(k) contributions on your tax return.

Payroll platforms like Gusto, ADP, or Paychex do not automatically know what you intended to defer into your self-administered Solo 401(k). You must manually enter your elective deferrals into their system or submit a year-end adjustment before W-2s are generated on January 31st.

Small payroll details create huge tax filing headaches if they're missed.

Want to ensure your S Corp payroll and W-2 reporting are set up correctly before January 31st? Send me a message or book a call.

Listen to the full episode 96
“Build Your Wealth Muscle” podcast. Wherever you listen.

related: S-corp 401k, Solo 401k, W2 deadline, 401k W2 reporting, payroll and 401k, W2 compensation, S-corp retirement planning, 401k employee contributions, small business taxes, S-corp owner

09/15/2026

If you’re an S-corp owner with a Solo 401k, the paperwork and timing matter.

Your 401k has an employee side and an employer side. The employee side is tied to your W2 compensation, which is why your salary and payroll need to be planned correctly.

January 31 is the general W2 deadline, not the general Solo 401k contribution deadline. So you don’t want to wait until you’re filing your taxes to figure this out.

The employer side has a different deadline and can generally be handled by your business tax-filing deadline, including extensions.

There are some great opportunities with an S-corp, but there are also rules and paperwork you have to get right.

Listen to the full episode 96
“Build Your Wealth Muscle” podcast. Wherever you listen.

related: S-corp 401k, Solo 401k, W2 compensation, 401k deadlines, S-corp retirement, 401k contributions, S-corp taxes, small business taxes, business retirement plan, tax planning

09/12/2026

If your smartest investor complains that your 401(k) menu is too basic, good.

A retirement plan is built to get your entire team to actually save, not for day traders.

When business owners set up a 401(k), a common mistake is offering a bloated, 50-fund menu to satisfy experienced investors. Research consistently shows that giving non-investors too many options triggers "choice paralysis," causing them to delay enrolling altogether.

Tier 1: Qualified Default (QDIA)
- Target-Date Funds (TDFs)
- Automatically rebalances over time
- Designed for first-time savers
- Protects employer under ERISA 404c

Tier 2: Self-Directed Brokerage
- Open access to stocks/ETFs/funds
- Requires formal risk waiver signed
- For advanced/sophisticated traders
- Isolates fiduciary liability

By making Target-Date Funds (TDFs) your Qualified Default Investment Alternative (QDIA), employees who don't know how to pick stocks automatically get a professionally managed, age-appropriate portfolio.

If you want to keep the main menu simple for beginner savers without frustrating your experienced employees, use a Self-Directed Brokerage Option (SDBO):

The Core Menu (10–15 Funds): Keep the main lineup clean with low-cost index funds, target-date funds, and core bond funds. This serves 90% of your staff effortlessly.

The Brokerage Window (SDBO): Allow advanced investors to opt into a side window giving them access to thousands of individual stocks, ETFs, and mutual funds.

Your goal as a plan sponsor isn't to provide infinite options. It's to build a compliant, low-cost structure that gets your employees to participate and build wealth safely.

Setting up or benchmarking a 401(k) plan for your business?

Send me a message or book a call to review your plan design and fiduciary options.

Listen to the full episode 96
“Build Your Wealth Muscle” podcast. Wherever you listen.

related: 401k investment options, target date funds, 401k investing, employer 401k plan, employee retirement plan, retirement investment choices, diversified funds, business owner retirement plan, 401k plan design, retirement planning

09/11/2026

If you looked at your old company 401k and thought “That sucked. I only had a handful of investment choices,” there’s actually a reason many plans are structured that way.

Employers don’t just throw unlimited investments into a 401k and let employees figure it out.

The people responsible for the plan have fiduciary responsibilities when selecting and monitoring the investment options available to participants.

They have to follow a prudent process and act in the interests of the people in the plan.

That doesn’t mean every investment is guaranteed to perform well. It means there are responsibilities behind the investment menu you’re given.

So having fewer choices isn’t always a bad thing. Sometimes a curated selection is part of how a plan is designed and managed.

Listen to the full episode 96
“Build Your Wealth Muscle” podcast. Wherever you listen.

related: 401k investment options, 401k investment choices, employer 401k, 401k fiduciary responsibility, retirement plan investments, 401k plan design, retirement investing, employer retirement plan, 401k investment menu, retirement planning

09/09/2026

Not every 401k’s works the same way.

You might hear that you can borrow from a 401k, then ask your employer about it and get told no.

That doesn’t necessarily mean 401k loans aren’t allowed. It may simply mean that your specific plan doesn’t offer them.

A 401k plan can allow participant loans, but the employer isn’t required to include that option in the plan.

The same goes for fees. 401k fees have generally come down over the years, especially investment expenses, but you should still pay attention to what you’re paying because fees can vary from plan to plan.

The plan matters just as much as the type of retirement account.

Listen to the full episode 96
“Build Your Wealth Muscle” podcast. Wherever you listen.

related: 401k loans, 401k loan rules, can you borrow from a 401k, 401k plan fees, retirement plan fees, 401k retirement planning, employer 401k plan, participant loan, retirement account rules, 401k benefits

09/08/2026

When we talk about retirement plan deadlines, remember this: the paperwork deadline and the contribution deadline aren’t always the same thing.

Getting the plan set up is one step but actually putting the money into the account can be another step with a different deadline.

So if you’re thinking about starting a retirement plan but don’t have all the cash ready yet, don’t automatically assume you’ve missed your opportunity.

The deadlines depend on the type of plan and the type of contribution, so make sure you’re looking at both before making a decision.

Listen to the full episode 96
“Build Your Wealth Muscle” podcast. Wherever you listen.

related: retirement plan deadlines, Solo 401k deadlines, SEP IRA deadlines, retirement contributions, business owner retirement plan, 401k contribution deadline, SEP IRA contribution deadline, small business retirement planning, tax planning, retirement plan setup

09/07/2026

Business owners, your next tax deadline is coming up! September 15 is the deadline for your Q3 estimated tax payment if you’re self-employed, a business owner, or making quarterly tax payments to the IRS.

Don’t wait until the last minute — missing your estimated tax deadline could lead to interest charges, underpayment penalties, and unnecessary stress. Reviewing your income, expenses, deductions, and tax strategy now can help you stay prepared and avoid surprises when tax season arrives.

Save this reminder and make sure your business taxes are on track before September 15.

Related: Q3 estimated tax payment, September 15 tax deadline, IRS quarterly tax deadline, small business tax planning, self employed tax payments, business owner tax tips, estimated tax payments, avoid IRS penalties, quarterly tax strategy, entrepreneur tax planning

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