By: Jessica Williams
As millions of owner-led firms approach transition, incremental AI adoption is redefining documentation, underwriting, and deal viability.
Across the United States, ownership transitions in the lower market and lower middle market are becoming a core economic issue rather than a niche transactional concern. As federal agencies incrementally expand the documented use of artificial intelligence to improve workflow clarity and information management, private-sector operators positioned near public missions are experiencing similar pressures around data structure, underwriting readiness, and diligence standards.
The U.S. Government Accountability Office reported that identified generative AI use cases across federal agencies increased from 571 in 2023 to 1,110 in 2024, and formal generative AI applications grew from 32 to 282 (GAO, 2025). This shift does not represent a rapid overhaul; instead, it signals a gradual institutional movement toward systems that expect cleaner documentation and verifiable information.
This evolution intersects with a demographic reality. Approximately 2.9 million U.S. businesses owned by Baby Boomers employ nearly 32 million workers and produce an estimated 6.5 trillion dollars in annual revenue, subject to ownership change (Project Equity, 2025). Without effective transitions, many of these firms will close rather than transfer, reducing the local institutional capacity that supports tax bases, employment, and municipal function. The exposure is not theoretical; it is measurable and approaching.
Banking data reinforces what transition environments require. The FDIC’s 2024 Small Business Lending Survey notes that community banks hold a minority share of national banking assets yet originate a disproportionate share of small-business lending. The most frequent causes of declined acquisition financing remain insufficient documentation, unclear working capital needs, and incomplete diligence files (FDIC, 2024). In markets where public-sector revenue, regulatory oversight, or government contracting obligations are present, these documentation lapses can eliminate deals that would otherwise preserve local continuity.
God Bless Retirement (GBR), a Fort Worth–based brokerage serving the lower middle market and Main Street, is adopting AI-powered capabilities to improve file preparation, accelerate document review, and create clearer pathways for lender engagement. GBR’s relevance does not imply that it solves a national problem. Instead, the firm aims to demonstrate how responsible use of workflow tools can increase deal flow, keep regional lenders active, and lower capital issuance costs by reducing underwriting friction. In practice, AI-supported packaging is deployed to make transactions more navigable, not more abstract.

Photo Courtesy: God Bless Retirement
(Left: The Chicotsky family, which leads the Fort Worth-based business brokerage, God Bless Retirement. Right: Blake Oliver, Associate Broker at God Bless Retirement.)
“Small business owners deserve a transition that matches the value they built over years of work,” said Blake Oliver, Associate Broker at God Bless Retirement. The firm’s managing principal, Dr Brandon Chicotsky, adds, “AI is being incorporated to strengthen, not displace, the judgment of lenders, brokers, and operators. Thus, we host civic gatherings, with some of them focused on AI, to help professionals understand these tools together in an environment where informed use may improve the likelihood that Main Street and lower market businesses transfer rather than disappear.”
Rather than focusing on panels or programming as endpoints, GBR’s approach is to bring together professionals in the service of capital, lenders, investors, operators, and advisors, to normalize expectations around information standards and underwriting transparency. The intended downstream effect is a transaction environment in which documentation is cleaner, loan submittals are more viable, and community banks remain flush and competitive, enabling more favorable loan terms locally and regionally. In doing so, local stakeholders gain both an informational and positional advantage, reducing the frequency of failed transactions that remove productive assets from the economy.
GBR’s year-launch gathering will convene leaders spanning public policy, finance, technology, and capital formation. Participants include Tan Parker, Texas State Senator for District 12, whose legislative work has focused on economic vitality and governance reform; John Nichols, Innovation Technical Lead for AI & Innovation within Ernst & Young’s Government & Public Sector practice; and Chase Friedman, Managing Partner at Alpine Anchor, an AI automation firm focused on operational scaling for small and mid-sized enterprises.
The program also includes civic and financial leadership, with Gilbert Little, Private Banker at First Horizon Bank, serving as invocation leader, and Dr. Andrea Sasha Ortiz, international award-winning clinical psychologist and Miss World International 2024, leading the U.S. and Texas pledges for attendees. Together, these contributors add a spirit of patriotism and purpose, which represent the cross-institutional perspectives required to address modernization, underwriting transparency, and ownership transition in Main Street and lower middle-market environments.

Photo Courtesy: God Bless Retirement – a promotion of their January 2025 professional gathering on AI
Professional gatherings that bring private capital together may help accelerate deal flow and technological adoption. Such gatherings are catalyzed by a bigger mission. For example, in addition to convening capital professionals, God Bless Retirement formally aligns its events with nonprofit organizations supporting veterans and military families. Partner organizations include the Special Forces Foundation, which provides mental health, transition, and family support services for U.S. Army Special Forces personnel and Gold Star families, as well as Roll Call, Halo for Freedom, Cloud Dancer Foundation, and Undaunted.
GBR also recognizes veteran community leadership through individuals such as Alexia Tuttle, Managing Partner at Tuttle Equity, whose work focuses on connecting veteran-led enterprises with capital networks. These partnerships reflect a broader view of economic stewardship, one that links ownership transition, institutional continuity, and service to those who have supported the country’s civic and financial infrastructure.
By pairing stewardship values with incremental technological adoption, GBR shows how brokerage firms can reinforce, rather than replace, relationship-driven finance. This work emphasizes market conditioning, aligning participants for an orderly transfer of ownership at a time when the country’s economic structure benefits from continuity and stability. As GBR’s Associate Broker, Blake Oliver, says, “Technological advancement is inevitable, and so it’s no surprise our strongest strategic partners are getting deals done to dignify proprietors who are liquidating, as well as buyers aiming to strengthen their vertical or assume a new cash flow entity. And the ones doing it best are those who are intentional adopters of AI functions.”
Contact God Bless Retirement:
References
- Federal Deposit Insurance Corporation. (2024). FDIC Small Business Lending Survey: Findings and Observations. FDIC. https://www.fdic.gov/publications/2024-report-small-business-lending-survey
- Finance & Commerce. (2025, July 22). Economic shifts create challenges for aging entrepreneurs. Finance & Commerce.
- Government Accountability Office. (2025). Artificial Intelligence: Federal Agencies’ Use of Generative AI and Early Management Approaches (GAO-25-107653). U.S. Government Accountability Office. https://www.gao.gov/products/gao-25-107653
- Project Equity. (2025, March 14). Business owner demographics and exit exposure in the United States. Project Equity.
Disclaimer: The information provided in this article is for general informational purposes only. The content is not intended to serve as professional advice and should not be relied upon as such. Readers are encouraged to seek professional guidance for their specific circumstances.