Retirement savings
Business, Economy, Finance, Investment, Retirement, TaxesMaggie Tredwell

The $200,000 Retirement Contribution Most Business Owners Don’t Know Exists

The $200,000 Retirement Contribution Most Business Owners Don’t Know Exists

By Brian Wheeler, Principal, Keystone Wealth Advisors 

Many business owners assume their retirement plan is already doing everything it can.

 

After all, they’re contributing to their 401(k), their employees have a plan available, and their payroll provider handles the administration. Everything seems to be working.

Retirement savings

But Here's the Surprising Reality:

Many successful business owners are leaving six-figure tax deductions on the table every year.

 

Not because they’re doing anything wrong — but because their retirement plan was designed for simplicity, not optimization.

The Hidden Opportunity

Most retirement plans set up through payroll providers are prototype 401(k) plans. These plans are convenient and easy to administer, but they are typically designed to serve the broadest possible group of employers.

 

That means they often don’t take full advantage of the flexibility available under the tax code.

 

For business owners with strong income and stable cash flow, there may be an opportunity to significantly increase retirement contributions through a more customized plan design.

When a Retirement Plan Becomes a Strategic Tool

In the right situation, combining a 401(k) plan with a Defined Benefit plan can dramatically increase the amount a business owner is able to contribute each year.

 

Depending on factors such as age, income, and employee demographics, total contributions can sometimes reach: $150,000 – $300,000+ annually. 

 

These contributions are typically:

 

  • Tax deductible to the business
  • Compounding tax-deferred for retirement
  • Building wealth outside the business

For owners in their peak earning years, this strategy can become one of the most powerful ways to reduce taxes while accelerating retirement savings. 

Why Plan Design Matters

Retirement plans are not one-size-fits-all.

 

The amount a business owner can contribute depends heavily on how the plan is structured. Key factors include:

 

  • Owner age and income
  • Number and age of employees
  • Compensation structure
  • Business profitability
  • Long-term retirement goals

A properly designed plan can allow owners to maximize their own contributions while still providing meaningful benefits to employees and remaining fully compliant.

The Limits of “Off-the-Shelf” Plans

Payroll providers often offer retirement plans as a convenient add-on to payroll services.

 

While these plans are easy to implement, they are typically built using standardized designs that may not incorporate strategies such as:

 

  • Age-weighted allocations
  • Cross-tested profit sharing
  • Cash balance or defined benefit integrations
  • Advanced plan design techniques

For high-income business owners, these limitations can translate into missed opportunities for significant tax savings.

Beyond the Business

For many entrepreneurs, the business itself becomes their largest asset.

 

But relying on the eventual sale of the business alone can create risk.

 

A well-structured retirement plan allows owners to systematically move wealth out of the business and into personal assets while benefiting from meaningful tax deductions along the way.

A Question Worth Asking

If your business is having a strong year, it may be worth asking:

 

Is my retirement plan designed for convenience… or designed to maximize opportunity?

 

The difference can be substantial.

Better Together

At Keystone, our teams work together across tax, wealth advisory, and business consulting to help business owners design retirement strategies that align with both their business success and their long-term financial goals.

 

If you’d like to explore whether your retirement plan could be working harder for you, we would be happy to start that conversation.

business deal
Business, Economy, Finance, Investment, RetirementMaggie Tredwell

Buying a Business? That’s an Estate Planning Event (Whether You Realize It or Not)

Buying a Business? That’s an Estate Planning Event (Whether You Realize It or Not)

By Brian Wheeler

For many business owners, acquiring a company feels like a growth decision — a strategic move to increase revenue, expand capabilities, or create long-term value.
 
What often goes unrecognized is this: a business acquisition is also a major estate planning event.
 
Not in the dramatic sense. Not because something went wrong. But because ownership, control, valuation, and future outcomes just changed — sometimes significantly — and estate plans are rarely built to keep up automatically.
business deal

When Business Evolves Faster Than Estate Planning

Most estate plans are created during relatively calm seasons of life. A business is established, assets are identified, beneficiaries are named, and documents are signed. At the time, everything makes sense.
 
Then life — and business — happens.
 
  • A company is acquired
  • New entities are formed
  • Ownership percentages shift
  • Debt or earn-out structures are introduced
  • The overall value of the business changes materially
Yet the estate plan often remains untouched. This isn’t neglect. It’s reality.
 
Estate planning documents are static by nature, while businesses are dynamic. Over time, the assumptions that once made the plan effective can quietly become outdated.

Why acquisitions matter more than most people realize

When a business acquisition occurs, it can impact estate planning in ways that aren’t always obvious:
 
  • Ownership structure changes How assets are titled and who controls them can shift overnight.
  • Control and decision-making matter Voting rights, management authority, and successor control may not align with what estate documents assume.
  • Valuation assumptions change A business that was once valued modestly may now represent a significant portion of a family’s net worth.
  • Liquidity expectations shift Estate plans may assume liquidity that doesn’t exist — or fail to account for future liquidity events.
  • Buy-sell agreements may conflict with existing plans Well-intentioned agreements can override or contradict wills and trusts if they’re not coordinated.
Each of these changes can affect outcomes for spouses, children, business partners, and future generations — even when everyone involved has the best intentions.

Selling a business can be an even bigger estate planning event

For sellers, the shift can be even more dramatic. A business that once represented largely illiquid value may suddenly become cash, marketable securities, or structured payments — often all at once.
 
That transition can:
 
  • Change the size and composition of an estate overnight
  • Create new tax planning considerations
  • Alter how assets should be titled, gifted, or protected
  • Shift legacy goals from business continuity to wealth transfer
Without coordination, sellers may find that their estate plan reflects the business they used to own, not the wealth they now have.

The most common issue we see: outdated plans

One of the most consistent patterns across business owners is this: “I have an estate plan… I just haven’t looked at it in a while.”
 
That “while” often includes:
 
  • Business growth
  • Acquisitions or mergers
  • Business sales or partial exits
  • Changes in partners or ownership percentages
  • Shifts in family dynamics
  • Changes in tax law
An estate plan that hasn’t been reviewed alongside these changes may still be legally valid — but strategically misaligned.

Estate planning — and the legal profession — has evolved

Estate planning hasn’t changed in isolation. The legal profession itself has evolved alongside increasingly complex business ownership and wealth structures.
 
Many estate planning attorneys today:
 
  • Work within more sophisticated ownership and succession models themselves
  • Rely on technology to model outcomes, track changes, and improve coordination
  • Focus less on one-time document creation and more on ongoing strategy
This evolution reflects a broader reality: modern estate planning works best when it’s timely, collaborative, and aligned with real-world business dynamics — especially after acquisitions, restructures, or ownership changes.

A coordinated approach leads to better outcomes

When estate planning is addressed proactively — whether following an acquisition or a sale — it allows for:

 

  • Clear alignment between business agreements and estate documents
  • Thoughtful planning around control, liquidity, and succession
  • Fewer surprises for heirs and business partners
  • Greater confidence that intentions will translate into outcomes
Most importantly, it gives business owners peace of mind knowing that major transactions won’t unintentionally create complications for their family or legacy.

A Simple Takeaway

Whether you’re acquiring a business, preparing to sell, or have recently completed a transaction, it may be time for a coordinated review — not just of the deal itself, but of how your estate plan aligns with it.
 
Estate planning works best when it keeps pace with life and business, and when the right professionals are working together with clarity and intention.
 
You don’t have to navigate that alone — and you don’t have to wait for a problem to start the conversation.
retirement planning
Business, Economy, Finance, Investment, RetirementMaggie Tredwell

“I’m Eligible for Social Security Soon… So When Should I Actually Take It?” (A decision that feels simple — until it isn’t.)

“I’m Eligible for Social Security Soon… So When Should I Actually Take It?”

(A decision that feels simple — until it isn’t)

By Brian Wheeler

For many people nearing retirement, Social Security feels like a finish line. “I paid in for decades… now when do I start collecting?”

 

Turns out, that question has real financial consequences, and the “right” answer is rarely the same for everyone.

 

Let’s break it down — clearly, concisely, and without putting you to sleep.

retirement planning

The Three Social Security Ages (Think: Early, On Time, or Fashionably Late)

Age 62 – The Early Bird Option Yes, you can start Social Security at 62. But there’s a catch: your benefit is permanently reduced — often by 25–30% compared to waiting until Full Retirement Age.

 

This can make sense if:

 

  • You need income now
  • Health or longevity is a concern
  • You plan to stop working entirely

But remember: early means smaller checks for life.

Full Retirement Age (FRA) – The “No Penalty” Zone For most people today, FRA is 66–67, depending on birth year.

At this point:

 

  • You receive 100% of your calculated benefit
  • You can earn income without Social Security penalties
  • Spousal strategies become more flexible

For many retirees, this is the “default” choice — but not always the optimal one.

 

Age 70 – The Patient Optimizer if you delay benefits beyond FRA, your benefit grows by 8% per year until age 70.

That’s not hypothetical math — it’s a guaranteed, inflation-adjusted increase backed by the government.

 

This option often shines if:

 

  • You expect a longer lifespan
  • You want higher lifetime or survivor benefits
  • You’re still earning income or have other assets to bridge the gap

So… What’s the “Best” Age?

Here’s the honest answer: Social Security is not just a claiming decision — it’s a planning decision.

 

The best time to start depends on:

 

  • Your health and life expectancy
  • Marital status and spousal benefits
  • Other income sources (work, pensions, investments)
  • Taxes (yes, Social Security can be taxable)
  • How long your money needs to last

In other words: the check is simple — the decision is not.

A Common (and Costly) Mistake

Many people claim early simply because they can, not because they should. We often see:

 

“I didn’t want to leave money on the table.”

 

Ironically, that mindset can do exactly that — just in the opposite direction.

The Bottom Line

Social Security is one of the few guaranteed income sources most retirees will ever have.

 

Deciding when to turn it on can impact hundreds of thousands of dollars over a lifetime. It’s not about maximizing a benefit in isolation — it’s about coordinating Social Security with the rest of your financial life.

 

And no… this is not a decision you have to make alone.

 

Thinking about Social Security soon? A second set of eyes can make all the difference — especially when timing, taxes, and long-term outcomes are on the line.

 

(Because “I think this is right” and “I know this works” are very different feelings.)

Finance, Investment, RetirementChris Meredith

No More Government Checks

Big changes are coming to the way the federal government handles payments. On March 25, 2025, the White House announced an executive order titled “Modernizing Payments To and From America’s Bank Account” (EO 14247). Beginning September 30, 2025, the federal government will stop issuing paper checks for most payments. This includes IRS tax refunds, Social Security benefits, veterans’ benefits, and even vendor payments. The order also directs that payments to the federal government, such as taxes and fees, must be made electronically as soon as practicable. For taxpayers, the easiest option is to use the IRS website to make payments online.

Continue Read
1 2

Business sales and transactions through Keystone Business Brokers are executed by Michael D. Bosma, CPA / Business Broker Lic. #S.191008 / BUSB #7085, who is affiliated with NAI Alliance and operates under that license while doing business as Keystone Business Brokers. NV License S.191008 / Business Broker Permit #7085. NAI Alliance dba Keystone Business Brokers. Copyright © 2025 Keystone CPAs, All Rights Reserved. Advisory services are offered through Keystone Wealth Advisors, LLC, An Investment Advisor in the State of Nevada. | Site By Design On Edge