Scott is the leader of the firm’s tax planning team and co-chair of the firm’s private equity industry team. The scope of Scott’s tax practice encompasses tax planning for business formations, ownership arrangements, LLC agreements and M&A transactions. Scott’s corporate practice extends to handling M&A transactions, equity compensation arrangements and general corporate law matters.
Scott is recognized for his tax planning work with founders, investors, and businesses with respect to their qualified small business stock (QSBS) issues. Scott has written numerous articles addressing QSBS planning issues, and he has developed a national practice handling Section 1202 and 1045 issues. Scott’s focus is on securing and maximizing Section 1202’s generous tax benefits for his clients.
Scott has represented companies, founders, investors, management teams, executives, PE sponsors, family offices and individuals across a wide variety of industries, including healthcare, direct marketing, gaming, industrial and commercial real estate development, distributorship, software and hospitality. Scott applies his expertise and experience to assist clients in achieving their business objectives, whether that means limiting an exposure to contingent liabilities or finding the most tax efficient structure for a business transaction.
Scott Dolson and Frost Brown Todd’s tax planning team have substantial expertise and experience handling tax planning for corporations, S corporation and pass-through entities, including choice of entity planning, equity compensation planning and M&A planning.
The tax planning team’s Section 1202 and Section 1045 work involves tax planning and implementation of planning ideas for founders, investors, venture firms, venture funds, PE firms, PE funds, family offices, wealth planners, investments bankers, accountants and attorneys, including (i) helping clients navigate through their choice of entity decision, and in particular their decision whether to operate as a C corporation with the hope of benefiting from the Section 1202 gain exclusion; (ii) helping client satisfy Section 1202’s and Section 1045’s eligibility requirements; and (iii) helping clients prepare for a potential future IRS audit by documenting their eligibility to claim the Section 1202 gain exclusion.
FBT’s QSBS practice encompasses the following:
Assisting businesses:
Assisting founders and service providers:
Assisting investors:
Assisting investment funds:
Assisted business owners with their business succession planning, culminating in ESOPs, sales to family members, management or other investors, or to outside financial or strategic buyers.
Handled or managed M&A work for financial buyers acquiring targets in a variety of industry areas.
Assisted PE firms with development of their internal and portfolio company governance and compensation documents.
In connection with handing M&A work for business owners, assisted with structuring and implementing tax favored equity rollovers, including the tax and governance (minority owner) issues.
Developed and coordinated both general and specialized due diligence projects for lower-middle and middle market PE firms (e.g., an immigration-focused due diligence investigation of a Southwest US construction general contractor which utilized a network of independent contractors with their own construction teams).
Managed the firm’s outside general counsel services for PE firms’ portfolio companies (with legal needs ranging from managing world-class IP portfolios to negotiating collective bargaining agreements).
For a leading skilled nursing and personal services company, developed and implemented a specialized and comprehensive due diligence examination of a target company’s independent contractor arrangement.
Handled the structuring of numerous real estate development projects involving industrial or commercial properties, including associated partnership tax planning and LLC governance issues, in transactions often involving property owners, developers and investors.
Handled tax and business issues associated with the conversion of a closely-held LLC to a public company, including the roll-up of franchisee stores.
Handled transactions involving a Heisman Trophy Winner, an NFL Hall of Fame member and Super Bowl champion, a Triple Crown winner, and a PGA player of the year.
Advised numerous clients regarding LLC controlling and minority governance and fiduciary duty issues.
Structured and drafted hundreds of closely-held business, investment, family business and wealth and real estate investment and development limited liability companies.
Advised clients in connection with their tax planning, including structuring closely-held business and investment arrangements and transaction tax planning.
Advised clients in connection with the organization and operation of employer assistance organization public charities and other employer assistance vehicles.
Health Care: home health, personal care, nursing homes, drug treatment clinics, pharma (cancer; macular degeneration), and hearing aid manufacturer and retailer.
Manufacturing: environmental cyclones, after-market automobile parts, chemical storage tank, specialty glass, and metal fabricating.
Entertainment and hospitality: numerous fast-food and casual dining restaurant concepts, including Long John Silvers and Texas Roadhouse, hotels, minor league baseball team, racetrack and gaming operations, and sports and entertainment agencies.
IP/software: blue tooth company, printing, direct mail, developer of optical cables and engines, various software developers and licensing companies, and e-commerce B2B and B2R businesses.
Insurance: title insurance, surety bond, bail bond and general lines agencies and surety bond underwriters.
Retail: convenience stores, specialty pet products, equine, personalized apparel, auto dealerships, funeral homes and printing houses.
Advertising: general advertising agency and auto industry direct marketing.
Construction and real estate: general contractors, asphalt plants, replacement windows, ready-mix concrete, numerous industrial and commercial property projects, rock quarries, underground and surface coal mining and oil and gas.
Waste: waste collection, landfills, metal recycling and hazardous waste incinerators.
Professional: lawyers, accountants and physicians.
University of Virginia School of Law, J.D.
Harvard College, A.B., with honors
Chambers USA, Corporate/M&A, 2005, 2008–2024
Selected for inclusion in Kentucky Super Lawyers®, Tax, 2007-2016
The Best Lawyers in America®, Corporate Law, 2006-2025; Mergers & Acquisitions Law, 2007-2025; Tax Law, 2010-2023, 2025; Business Organizations (including LLCs and Partnerships), 2024-2025, “Lawyer of the Year,” 2025
Peer Review Rated, Martindale-Hubbell®
Louisville Free Public Library Foundation, Legal Counsel
“Dolson’s Limited Liability Company Forms,” University of Kentucky College of Law/Office of Continuing Legal Education Books
“Kentucky Limited Liability Companies, Business Succession, Planning and Kentucky Corporations Handbook,”
University of Kentucky College of Law/Office of Continuing Legal Education Books
“Professional Services Corporations,”
University of Kentucky College of Law/Office of Continuing Legal Education Books
Assisted in drafting the Kentucky Business Corporation Act, the Kentucky Limited Liability Company Act, and the Kentucky Registered Limited Liability Partnership Provisions
September 30, 2024 | Blogs
Section 1202 provides for a substantial exclusion of gain from federal income taxes when stockholder...
September 4, 2024 | Publications
This article is one in a series of articles and blogs addressing planning issues relating to qualifi...
July 22, 2024 | Tax Law Defined™ Blog
Section 1202 provides for a substantial exclusion of gain from federal income taxes if a stockholder...
April 25, 2024 | Blogs
Stockholders must satisfy several eligibility requirements before they can claim Section 1202’s ge...
April 16, 2024 | Publications
The Simple Agreement for Future Equity (SAFE) was introduced in 2013 on the startup accelerator Y Co...
April 12, 2024 | Blogs
The Simple Agreement for Future Equity (SAFE) was introduced in 2013 by startup accelerator Y Combin...
March 19, 2024 | Blogs
Section 1202 provides for a substantial exclusion of taxable gain from federal income taxes when sto...
January 17, 2024 | Blogs
The combination of the 21% corporate federal income tax rate and the possibility of qualifying for S...
October 26, 2023 | Tax Law Defined™ Blog
Section 1202 provides for a substantial exclusion of gain from federal income taxes when stockholder...
October 12, 2023 | Blogs
The combination of the 21% corporate income tax rate and the possibility of qualifying for Section 1...
July 3, 2023 | Blogs
Section 1202 provides for a substantial exclusion of gain from federal income taxes when stockholder...
October 6, 2022 | Blogs
There are numerous tax and business issues associated with equity compensation planning for employee...
September 12, 2022 | Blogs
Section 1202 allows stockholders to claim a minimum $10 million federal income tax gain exclusion in...
May 17, 2022 | Blogs
During the past several years, there has been a marked increase across the country in the use of C c...
May 13, 2022 | Blogs
When Section 1202 was enacted in 1993, a 50% gain exclusion applicable to the sale of qualified smal...
April 19, 2022 | Blogs
Section 1045 allows stockholders to reinvest on a pre-tax basis, proceeds from the sale of qualified...
April 19, 2022 | Blogs
Section 1045 allows stockholders to reinvest on a pre-tax basis, proceeds from the sale of qualified...
April 19, 2022 | Blogs
A stockholder must hold qualified small business stock (QSBS) for more than five years in order to c...
February 16, 2022 | Blogs
We have discussed in previous articles the potential benefits of operating a start-up as a C corpora...
January 26, 2022 | Blogs
Section 1202 allows taxpayers to exclude gain on the sale of QSBS if all eligibility requirements ar...
November 3, 2021 | Blogs
On September 13, 2021, legislation emerged from the House Ways and Means Committee that included an ...
September 30, 2021 | Blogs
The number of private companies electing to go public through a transaction (referred to in this art...
September 29, 2021 | Blogs
This article addresses the consequences of “transfers at death” of qualified small business stoc...
September 16, 2021 | Blogs
When Congress enacted Section 1202, it noted that the gain exclusion was intended to “encourag...
September 3, 2021 | Blogs
Congress enacted Section 1202[i] based on the premise that the possibility of a $10 million gain exc...
September 3, 2021 | Blogs
This article addresses the importance of having bona fide (non-federal income tax) business and pers...
May 21, 2021 | Blogs
During the past several years, there has been a marked increase across the country in the use of C c...
April 15, 2021 | Blogs
During the past several years, there has been a marked increase across the country in the use of C c...
March 24, 2021 | Blogs
Synopsis The distribution of a C corporation’s assets to its shareholders often triggers a hea...
March 10, 2021 | Blogs
On January 13, 2021, the IRS posted final Treasury Regulations for Section 1061 of the Internal Reve...
March 10, 2021 | Blogs
Hedge fund, private equity and real estate professionals are often compensated through the grant of ...
February 22, 2021 | Blogs
Only the issuance of “stock” triggers the running of Section 1202’s five-year hold...
February 19, 2021 | Blogs
Many M&A transactions are structured to include a rollover of some percentage of the target comp...
January 28, 2021 | Blogs
During the 21st century, financial buyers such as private equity sponsors (PE firms) have dramatical...
January 27, 2021 | Blogs
A typical part of the sale of a business is the rollover of some equity by the target company’...
October 26, 2020 | Blogs
Beware of Mixing Section 1202’s Version of Oil and Water – S Corporations and QSBS Our Section 1...
September 18, 2020 | Blogs
With the corporate tax rate reduced from 35% to 21%, we have experienced a heightened awareness that...
August 5, 2020 | Blogs
With the corporate federal income tax rate reduced from 35% to 21%, there is a renewed interest in c...
June 11, 2020 | Blogs
As the M&A market begins to resume activity, what are the key areas for attention as transaction...
May 19, 2020 | Blogs
Navigating through recapitalizations, reorganizations, stock splits, reverse stock splits, tax free ...
May 8, 2020 | Blogs
In an earlier article titled “Rollover Equity Transactions 2019,” we discussed the vario...
April 8, 2020 | Blogs
Code section 139 excludes from taxable income “qualified disaster relief payments” made to reimb...
March 2, 2020 | Coronavirus Response Team
Employers are in search of ways to help employees who have been severely and unexpectedly impacted i...
February 17, 2020 | Blogs
This article is a guide for investors and fund sponsors who purchase, own and sell qualified small b...
January 17, 2020 | Blogs
This article is one of a series addressing planning issues relating to qualified small business stoc...
November 21, 2019 | Blogs
Revisiting Holding the Carried Interest Through an S Corporation Eighteen months ago, we published a...
November 1, 2019 | Blogs
A basic checklist of qualification requirements to help business owners and tax professionals consid...
October 21, 2019 | Blogs
PE buyers and target company owners are rightfully focused during the M&A process on the terms o...
July 16, 2019 | Publications
It isn’t unusual for shareholders holding vested stock in their target company to roll the sto...
July 6, 2019 | Blogs
A “golden parachute” is defined as an agreement between an employer and employee that tr...
June 14, 2019 | Blogs
Hedge fund, private equity and real estate professionals value the carried interest because it allow...
May 24, 2019 | Blogs
Why are tax opinions especially relevant today? Recent changes in the tax laws have left taxpayers a...
April 3, 2019 | Publications
I recently published an article focusing on the choice of entity decision for main street businesses...
January 2, 2019 | Blogs
During the past year, numerous articles have summarized and analyzed the changes made by the Tax Cut...
August 20, 2018 | Blogs
Under IRC § 1202, 100% of gain on the sale of QSBS acquired after September 27, 2010, is generally ...
July 26, 2018 | Publications
During the past decade, private equity investors and other financial buyers (referred to generally i...
July 26, 2018 | Blogs
During the past decade, private equity investors and other financial buyers (referred to generally...
April 24, 2018 | Blogs
Investment fund managers value compensation in the form of carried interests, which allows them to ...
March 12, 2018 | Blogs
The 2017 Tax Cuts and Jobs Act (the “2017 Tax Act”) ushered in several benefits for C corporatio...
February 26, 2018 | Blogs
During the past decade, the White House, Congress and the IRS have threatened on numerous occasions ...
February 5, 2018 | Blogs
Taxpayers who qualify for the IRC § 199A deduction (the “Deduction”) will be one of the...
January 22, 2018 | Blogs
In the aftermath of the 1986 tax act and the introduction of LLCs, pass-through entities (LLC and S ...
December 21, 2017 | Publications
New laws governing IRS partnership audits (the “New Audit Rules”) were enacted during 2015 and a...
May 5, 2015 | Blogs
On April 1, 2015, Kentucky Governor Steve Beshear signed into law House Bill 440, which includes s...