Lane Carrick on Founder Psychology, Deal Sabotage, and the M&A Emergency Room

Today's guest is Lane Carrick, founder of Optima Mergers & Acquisitions, a boutique lower middle market investment bank he launched in 2024. Lane brings a “renaissance man” profile and personal story to the M&A advisory seat: he grew up in the Holiday Inn franchise business his father built, completed a leveraged buyout in his 20s without knowing it, founded and exited a wealth management firm, cofounded B.B. King's Blues Club, and now teaches M&A and alternative investments at SMU as an adjunct professor.  He’s also a published author.  

Lane and Peter discuss the founder's exit journey through a business sale. Drawing on his experience as both an entrepreneur and advisor, Lane explains why some owners begin thinking about an exit only after a triggering event, why he often feels like an emergency room physician for founders, and how emotions are usually what put deals at risk. 

The conversation also covers private equity's complicated reputation among business owners, the importance of buyer chemistry, how sellers begin to second-guess a transaction as it approaches the finish line, and what to do about it.

Discussion Points:

• Lane Carrick’s entrepreneurial upbringing and early business influences
• Lessons learned from his father’s successful Holiday Inn exit
• Building and exiting his own wealth management business
• Why owners often decide to sell only after a triggering life event
• The difference between planned exits and emergency-room transactions
• Challenges of unsolicited acquisition offers from private equity firms
• The risks of negotiating with a single buyer versus running a competitive process
• Communication breakdowns between founders and institutional buyers
• The importance of specialized M&A legal counsel
• Setting valuation expectations before going to market
• Recognizing self-sabotaging behavior during the sale process
• Common misconceptions about private equity buyers
• Evaluating execution risk across private equity, search funds, and strategic buyers
• The importance of chemistry, trust, and cultural fit between buyers and sellers
• Building buyer relationships versus focusing on founder relationships
• How his new book helps owners assess sellability, optimization, and exit readiness
• Planning for identity and purpose after the sale of a business

Masters in Small Business M&A is produced by its host Peter Lehrman and the team at Axial (www.axial.com). Axial makes it easy for small business owners to confidentially explore growth capital and exit transactions with top-ranked lower middle market M&A advisors and professional capital partners. In every episode, we explore the dynamic world of small business M&A, interviewing a mix of proven and emerging owners, operators, acquirers, and M&A advisors whose strategies and methods are being put to the test.

If you’d like to go deeper, head to Axial.com, where we make available the Axial member directories, downloadable tools for dealmakers, the Axial quarterly lower middle market investment banking league-table ran...