Scale to Sell

Episode 73: How to Do a Roth Conversion Without Draining Your Retirement Savings to Pay the Taxes

Back in 2010, the income limits on Roth conversions went away, and Steve Burton expected clients to line up at the door. They did not. Most people agreed a conversion made sense right up until the moment they had to write the check to the IRS.

In this episode, Steve sits down with Ed Lyon, J.D., our certified tax and business advisor and co-author of How to Beat the IRS, Legally, to talk about why so few people convert and what has changed. Ed explains why the traditional CPA approach of converting a little each year guarantees you pay at least your current tax rate on every dollar, and how the Roth Accelerator strategy uses business and investment vehicles that create depreciation deductions and tax credits to offset some or all of the income from the conversion.

Ed calls the future tax bill inside a pretax IRA a tumor. It will not kill you, but it is going to hurt, and it grows every year you leave it alone. For a business owner with a couple million dollars in a 401(k) at age 50, those required minimum distributions could become $1 million a year of taxable income they never needed.

If you have half a million dollars or more sitting in pretax accounts, this conversation is worth your time.

In this episode:

• Why people did not rush to convert when the 2010 income limits disappeared
• The fundamental challenge of a Roth conversion: recognizing the income now
• Why the "fill up your bracket" CPA strategy still leaves you paying today's rate
• How the Roth Accelerator offsets conversion income with depreciation and tax credit strategies
• Where the money goes after it leaves the pretax environment
• The ideal candidate: roughly $500,000 or more in IRAs, 401(k)s, TSPs, or 403(b)s
• How required minimum distributions at age 73 can turn into a tax problem you do not need
• The real risk of converting: making a big decision without knowing future tax rates
• Why bringing your effective conversion rate down to around 10% makes a mistake much less likely
• Why your kids would rather inherit $1 million in a tax-free bucket than $1 million in an IRA (and the 10-year rule)

About our guest: Ed Lyon, J.D., is a tax attorney, a certified tax and business advisor, and co-author of How to Beat the IRS, Legally. He works with business owners and families to legally reduce income taxes, capital gains on business and real estate sales, and the future tax burden sitting inside retirement accounts.

Ready to see your numbers? There is no downside to getting an MRI on your pretax money. Schedule a discovery call and our team will run the analysis, show you what your future tax bill looks like, and tell you whether a Roth conversion strategy makes sense for you. Book your discovery call at ScaletoSell.com/discovery

Catch these episodes next:

• Episode 58: How business owners can legally pay less in taxes, with Ed Lyon
• Episode 71: How to Beat the IRS Legally and Tax Planning Strategies for Business Owners

Listen to all episodes

Connect with Scale to Sell: Website: ScaletoSell.com Free Business Valuation: ScaletoSell.com/value Podcast: ScaletoSell.com/podcast Facebook: facebook.com/ScaletoSell Instagram: @scaletosell YouTube: Scale to Sell on YouTube Email: [email protected] Phone: 757-313-4080

This episode is for educational purposes only and is not tax, legal, or investment advice. Every situation is different, so talk with a qualified professional before making changes to your retirement accounts.

Giac Biscotti joined the Navy at 18, fresh out of Brooklyn, and retired 26 years later as an air traffic controller. He spent the next couple of years inside a large company, where he learned how the business world works and noticed how much he missed the camaraderie of the military. When the government asked him to serve as deputy program lead on a brand-new landing system, he and his wife Holly (a fellow Navy air traffic controller) talked it over, prayed about it, and started ATCSI, a veteran-owned business built on the values they learned in uniform.

Today Giac is CEO of ATCSI and Dynamic Science Inc., an air traffic control company close to 80 years old that he and Holly acquired because its leaders shared their values. Their teams work coast to coast, in Japan, in Europe, and as far out as the Marshall Islands. That kind of reach makes micromanagement impossible, which suits Giac fine. He hires the right people and trusts them to use the talent they have.

In this conversation with Steve Burton, Giac talks about what changed when the quarterly checks to the IRS grew larger than anything he expected to earn, and why tax strategy for business owners is a different job than tax preparation. His longtime CPA, a great guy who once worked for Giac's brother, told him he had outgrown the relationship. Giac's picture of the difference is simple. A CPA who prepares your return is driving while looking in the rearview mirror, and a tax strategist is looking out the front window.

For Giac and Holly, the money they keep matters because of what it makes possible (veterans making the SkillBridge transition, causes they believe in, young people looking for their first job). As Giac puts it, God does not bless us so we can hold on to it. He blesses us so we can be a blessing to someone else.

Steve and Giac discuss:

• Why Giac left a large company after two years and what the corporate world taught him about business
• How 26 years as a Navy air traffic controller shaped the way he leads and why he pays attention to the small details
• Why ATCSI acquired Dynamic Science, a nearly 80-year-old company that already shared their values
• Leading teams across the U.S., Japan, Europe, and the Marshall Islands without micromanaging
• How Giac and Holly divide the work as husband and wife and as business partners
• The difference between a CPA who files your return and a tax strategist who plans ahead
• Why the physician who gives you a checkup is not the one you want doing your surgery, and what that means for your taxes
• How faith and stewardship shape what they do with what they keep
• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value
• Book your free discovery call with us today! www.scaletosell.com/discovery
• Get your copy of How to Beat the IRS, Legally www.scaletosell.com/discovery
• Listen to Episode 071: How to Beat the IRS Legally and Tax Planning Strategies for Business Owners

Connect with Giac Biscotti:

• ATCSI: atcsi.com
• Dynamic Science Inc.: dynamicscience.com
• LinkedIn: Giac Biscotti

Connect with Our Team:

• Website: Scale to Sell
• [email protected]
• Facebook: Scale to Sell
• YouTube: Scale to Sell
• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton
• LinkedIn: Steve Burton

Episode Summary

"My CPA of almost 30 years has never brought me anything that's helped me save anything in taxes."

That's not a stranger talking. That's Steve Burton, describing his own accountant, before he spent two decades looking for someone who actually did tax planning instead of tax reporting.

In this episode, Adam and Steve sit down to talk about How to Beat the IRS, Legally, the new book Steve wrote the foreword for alongside tax planner Ed Lyon. They break down the real difference between a CPA who keeps you compliant and a tax planner who actively works to reduce what you owe, using real examples, including one where a $500,000 capital gains bill on a piece of real estate was legally brought down to $50,000.

Adam and Steve discuss:

• Why Steve spent over twenty years looking for a CPA who actually did tax planning, and the "red light, green light" distinction the book uses to explain the gap between compliance and strategy.
• A real example where a business owner's CPA told him to write a $500,000 check on a real estate sale, and how proactive tax planning brought that bill down to $50,000.
• Why $400,000 in income tends to be the pain point where tax bills start to sting, and why tax planning has to happen in the current year, not the one you're filing for.
• Why these strategies, once reserved for the ultra-wealthy, are becoming available to business owners and upper middle class individuals who are paying more than they realize.
• And more!

Resources:

• Get your free copy of How to Beat the IRS Legally (while supplies last) at scaletosell.com/discovery
• Get your free personalized report at www.scaletosell.com/value
• Unlock your business's potential with our free Scale to Sell self-assessment
• What Your CPA Isn't Telling You About Your Exit (Ep. 69)

Connect with Our Team:

• Website: Scale to Sell
• [email protected]
• LinkedIn: Scale to Sell
• Facebook: Scale to Sell
• YouTube: Scale to Sell
• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton
• LinkedIn: Steve Burton

Episode Summary

Only 20 to 30% of businesses that go to market ever actually sell. Of the ones that do sell, most owners aren't happy with the outcome a year later. Somewhere between those two numbers sits a set of assumptions that feel true right up until the moment they cost you.

In this episode, Adam and Steve Burton walk through six misconceptions they hear constantly from business owners: about dependency, personal finances, taxes, life after the exit, timing, and industry multiples. Each one feels reasonable in the moment. Each one quietly limits what an owner actually walks away with.

Adam and Steve discuss:

• Why "the business can't run without me" feels like a badge of honor but is actually an inverse relationship with value, and how owner dependency shows up as risk to any buyer.
• Why personal and business finances aren't separate conversations, using a real client example where a couple's stated income was less than half their actual income once every benefit was counted.
• Why "I'll figure out what I want to do with my life after I sell" leads to regret, since most owners never build a picture of their next chapter before they're standing in it.
• Why "a good industry multiple means I'll get a good outcome" is a myth, since two businesses with identical revenue can land on completely different multiples depending on systems, leadership, and what the transcript calls the business's "intangible capital."
• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value
• Unlock your business's potential with our free Scale to Sell self-assessment
• Book your free discovery call with us today!
• What Your CPA Isn't Telling You About Your Exit (Ep. 69)

Connect with Our Team:

• Website: Scale to Sell
• [email protected]
• LinkedIn: Scale to Sell
• Facebook: Scale to Sell
• YouTube: Scale to Sell
• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton
• LinkedIn: Steve Burton

Episode Summary

Your CPA has never gotten you in trouble with the IRS. Deadlines are met, forms are filed, and everything looks fine. So why does the exit conversation still end with a massive, avoidable tax bill?

Most business owners assume that when they sell, the tax hit is just something they'll deal with when it comes. Their CPA rarely brings it up first, because a CPA's job is compliance and reporting on what already happened, not proactive planning for what's ahead.

In this episode, Adam and Steve Burton break down the difference between a CPA who prepares your taxes and a team that plans them, using a real client example where proactive tax strategy took a projected $3.4 million capital gains bill down to roughly $100,000.

Adam and Steve discuss:

• Why most CPAs are historians, not strategists, and why that distinction only becomes expensive at the moment of exit.
• The difference between tax preparation and tax planning, and why timing (years before a sale, not after) determines which options are even available.
• A real client example where proactive planning reduced a projected $3.4 million capital gains tax bill to around $100,000 on a $13.1 million business sale.
• Why paying hundreds of thousands or millions in income taxes is itself a signal that it's time for a specialized tax planning team, not just a compliance-focused CPA.
• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value
• Unlock your business's potential with our free Scale to Sell self-assessment
• Book your free discovery call with us today!
• Revenue vs. Enterprise Value (Ep. 65)

Connect with Our Team:

• Website: Scale to Sell
• [email protected]
• LinkedIn: Scale to Sell
• Facebook: Scale to Sell
• YouTube: Scale to Sell
• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton
• LinkedIn: Steve Burton

Episode Summary

You've built a business worth millions. So why does a lender's spreadsheet get the final say on whether your deal actually closes?

Business valuation is not just a number for a business owner's own curiosity. It is the foundation of every conversation that follows, from what a buyer is willing to pay to what a lender is willing to finance. Too many business owners skip this step entirely, tracking cash flow and growth without ever finding out what their business would actually sell for.

In this episode, Steve Burton talks with Jeff Snell, Founder and Principal Broker of ENLIGN Advisors, about what really drives a business sale, from risk mitigation and add-backs to the debt service coverage ratio that can cap a deal regardless of what a seller thinks their business is worth.

Steve and Jeff discuss:

• Why most business owners have never had a real valuation done, and why that gap becomes a problem the day they decide to sell.
• How buyers evaluate risk across culture, employee relationships, client contracts, and vendor dependencies, and why ENLIGN tracks 141 separate risk mitigation touch points.
• The difference between Seller's Discretionary Earnings and EBITDA, and why the crossover point around $750,000 in profit changes how a business should be valued.
• Why the debt service coverage ratio can cap a deal even when buyer and seller agree on a price, and the creative structuring options (rollover equity, seller financing, seller forgivable notes) that bridge the gap.
• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value
• Unlock your business's potential with our free Scale to Sell self-assessment
• Book your free discovery call with us today!
• Solving for the Debt Service Coverage Ratio in a High Interest Rate Environment (ENLIGN case study)

Connect with Our Team:

• Website: Scale to Sell
• [email protected]
• LinkedIn: Scale to Sell
• Facebook: Scale to Sell
• YouTube: Scale to Sell
• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton
• LinkedIn: Steve Burton

Connect with Jeff Snell:

• Website: ENLIGN Advisors
• LinkedIn: Jeff Snell

Episode Summary

You started your business to create freedom. So why does taking a vacation, stepping away for a few days, or even unplugging for an afternoon still feel impossible?

If your business depends on you to make every important decision, solve every problem, or keep operations moving, you've likely built an owner-dependent business. While that may feel like a sign of success, it can quietly limit your growth, reduce your business valuation, complicate succession planning, and create unnecessary stress for you and your team.

In this episode, Adam and Steve Burton explain why building a business that runs without you isn't about doing less. It's about creating stronger leadership, better systems, and a more transferable business that gives you greater freedom today while increasing your options for tomorrow.

Adam and Steve discuss:

• Why owner dependency is one of the biggest barriers to building a scalable, valuable, and sellable business.

• How to identify the systems, processes, and leadership gaps that keep you stuck as the bottleneck in your business.

• Why buyers place greater value on businesses with documented processes, empowered teams, and operational consistency.

• Practical strategies to reduce founder dependency, strengthen business continuity, and build an exit-ready company that can thrive without your daily involvement.

• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value

• Unlock your business's potential with our free Scale to Sell self-assessment

• Book your free discovery call with us today!

• AI Adoption Is a Leadership Problem, Not a Technology Problem (Ep. 66)

Connect with Our Team:

• Website: Scale to Sell

• [email protected]

• LinkedIn: Scale to Sell

• Facebook: Scale to Sell

• YouTube: Scale to Sell

• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton

• LinkedIn: Steve Burton

Most business owners see AI as a technology opportunity. Adam Burton sees it as a leadership opportunity. The businesses that get the most value from AI won't necessarily have the newest tools. They'll be the ones that build cultures of learning, adaptability, and continuous improvement.

In this episode, Adam Burton explores why successful AI adoption starts with leadership, not software. He discusses how business owners can help teams embrace change, create psychological safety around learning, and use AI to build stronger systems that support long-term growth and transferable value.

Adam discusses:

• Why successful AI adoption starts with leadership, not software

• How creating psychological safety encourages innovation and learning

• The difference between AI dabblers, operators, builders, and architects

• How AI and stronger systems can reduce owner dependency and increase transferable business value

• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value

• Unlock your business's potential with our free Scale to Sell self-assessment

• Book your free discovery call with us today!

Connect with Our Team:

• Website: Scale to Sell

• [email protected]

• LinkedIn: Scale to Sell

• Facebook: Scale to Sell

• YouTube: Scale to Sell

• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton

• LinkedIn: Steve Burton

What if your business isn't worth what you think it is?

In this episode, Adam and Steve Burton discuss a mistake they see business owners make all the time: confusing revenue with value. Using a real client story, they walk through what happened when a business owner believed her company was worth $9 million, only to discover its actual value was far lower because the business depended too heavily on her.

Adam and Steve discuss:

• Why revenue and enterprise value are two very different numbers

• How owner dependency can limit growth, freedom, and exit options

• The role systems, leadership, and recurring revenue play in business value

• Why two businesses with similar revenue can have very different valuations

• How building for value today can create more flexibility and opportunity in the future

• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value

• Unlock your business's potential with our free Scale to Sell self-assessment

• Book your free discovery call with us today!

Connect with Our Team:

• Website: Scale to Sell

• [email protected]

• LinkedIn: Scale to Sell

• Facebook: Scale to Sell

• YouTube: Scale to Sell

• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton

• LinkedIn: Steve Burton

Adam and Steve Burton just returned from one of the biggest exit planning conferences in the country, and one concept came up over and over again: most business owners are building businesses that still depend entirely on them.

In this episode, Adam and Steve discuss what truly drives a business's value beyond just increasing revenue. They explain the idea of reaching a "freedom point," when the business no longer depends entirely on the owner, and how the right systems, leadership, and planning can help create more flexibility, stronger growth, and better long-term options.

Adam and Steve discuss:

• Why growing revenue does not always increase the value of your business

• The "freedom point" concept and how to know when work becomes optional

• How do personal planning, business planning, and financial planning all work together

• Why so many owners regret selling their business, even after getting paid

• Generational differences in how owners approach growth, money, and work-life balance

• And more!

Resources:

• Get your free personalized report at www.scaletosell.com/value

• Unlock your business's potential with our free Scale to Sell self-assessment

• Book your free discovery call with us today!

Connect with Our Team:

• Website: Scale to Sell

• [email protected]

• LinkedIn: Scale to Sell

• Facebook: Scale to Sell

• YouTube: Scale to Sell

• Instagram: Scale to Sell

Connect with Adam Burton and Steve Burton:

• LinkedIn: Adam Burton

• LinkedIn: Steve Burton