Community Spotlight
Q&A: Lane Carrick on What Happens When Founders Wait Too Long to Sell
Lane Carrick has spent much of his career around founder-owned businesses. He grew up in the Holiday Inn franchise business his father built, completed a leveraged buyout in his twenties, and later founded and exited a wealth management firm. Today, he runs Optima Mergers & Acquisitions, a boutique middle-market investment bank he launched in 2024, and teaches M&A and alternative investments at SMU.
Carrick compares his work to that of an emergency room physician. Many owners come to him after a triggering life event. By then, the question is no longer whether they should prepare for a sale. It is how quickly they can get one done. He draws a clear line between planned exits and what he calls emergency room transactions, and the owners in the strongest position are the ones who start preparing well before any buyer appears.
One of the recurring problems he sees is the unsolicited offer. Private equity firms approach founders directly, and owners who enter a process with a single buyer have little context for judging price, deal structure, or the likelihood that the transaction will actually close. A competitive process gives the seller that context. It allows the owner to compare private equity firms, search funds, and strategic acquirers on price, execution risk, chemistry, and what happens to the business after closing.
Carrick also emphasizes setting valuation expectations before going to market. He first establishes a realistic range, and if the owner is unwilling to sell within it, the better option may be to improve the business before initiating a sale process. He points to specialized M&A legal counsel as another decision that shapes outcomes, along with clear communication between founders and institutional buyers, where breakdowns routinely put deals at risk.
The emotional side of selling gets equal weight in the conversation. Carrick says emotions, more than economics, are usually what put deals at risk, and sellers commonly begin to second-guess the transaction as it approaches the finish line. He describes this as self-sabotaging behavior and says advisors need to recognize it early.
That is why he encourages owners to plan for identity and purpose after the sale. For someone who has spent decades running the same company, selling removes more than just an income stream. The lesson for owners is that exit planning starts well before a buyer appears. Assessing whether the business is sellable, setting realistic expectations, and deciding what comes after the sale all create options. Waiting until circumstances force the decision means solving those problems at the moment the owner has the least time to do so.
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Governance Feed
Higher rates and tighter lending standards are pushing more owners to weigh sale-leasebacks against traditional debt. Bank financing typically advances only a percentage of a property's value and comes with covenants, leverage tests, and refinancing risk at maturity, while a sale-leaseback converts the full value of owned real estate into capital without diluting ownership. The trade is a long-term rent obligation that never amortizes, making the structure best suited to businesses with durable cash flow.
A business built to last is not automatically built to transfer. An estimated six million small and medium-sized businesses face ownership transitions by 2035, representing up to $5 trillion in enterprise value, yet Gallup research finds roughly half of US owners either plan to close when they step away or have no plan at all. The more useful question for an owner is whether the business can function without them, tested through revenue resilience, team decision-making, and documentation that lives outside the founder's head.
Selling a business to your children requires more than a handshake. An independent valuation keeps the price fair and prevents future family conflict. A tax advisor determines whether selling, gifting, or a hybrid transfer minimizes the burden, and a written agreement defining ownership, control, and responsibilities protects both the business and the relationships. The emotional aspect matters just as much, since children taking over often carry the weight of expectations from parents and employees alike.
Burnout is a legitimate reason to start exit planning, but a poor reason to set the timing and terms of a sale. The warning sign is when an owner's goal shifts from maximizing the outcome to simply finding relief, and the strongest exits usually begin two to five years before going to market. One owner who assumed he had missed his window instead spent 14 months preparing and closed a transaction that exceeded his original expectations.
Thesis Principle
Every advisor involved in a business sale has an incentive that shapes their advice. A Main Street broker earning a 10% to 12% commission is paid to close, which means the last $300,000 of value matters far less to them than it does to the seller. A lower-middle-market advisor collecting a $5,000 to $15,000 monthly retainer benefits from a longer engagement. A wealth advisor who charges fees on assets under management prefers maximum cash at closing over an installment sale or a seller note.
Resources & Events
📅 Virginia Capital Connection (Richmond, VA - September 30-October 1, 2026)
Virginia Capital Connection, hosted by ACG Richmond, brings together private equity firms, independent sponsors, lenders, investment bankers, and M&A advisors for two days of DealSource meetings, educational sessions, and networking. The program focuses on lower-middle-market transactions across business services, manufacturing, distribution, healthcare, and government contracting, with participants from across the Mid-Atlantic and Southeast. Details →
📅 Texas Association of Business Brokers 2026 Annual Conference (Lakeway, Texas - September 17-19, 2026)
TABB's annual conference brings Texas business brokers, intermediaries, and advisors to Lakeway Resort on Lake Travis for three days of education, certification courses, and networking under the theme Ignite Your Purpose. Pre-conference courses run before the main sessions, and the event includes a keynote, exhibitor floor, and golf outing. TABB is an IBBA affiliate, so the program supports continuing education for brokers pursuing or maintaining the Board Certified Broker designation. Details →
📊 Report Spotlight: The Net-Proceeds Report (Windsor Drake)
Windsor Drake's research desk examines why a founder's ownership percentage rarely matches their share of sale proceeds. Sale proceeds flow through a liquidation waterfall set in the company charter, and common shareholders sit at the bottom of it. In one case, a founder owning 47% of the company received 23% of the proceeds, and participating preference terms shifted roughly $10 million between investors and common holders. The report finds that 98% of deals carry a 1x preference, and 95% of preferences are non-participating, based on 2025 deal activity across software, fintech, AI, and cybersecurity. Read →
For the Commute
Lessons from Building Heritage Holding (Masters in Small Business M&A)
In this episode, Peter Lehrman speaks with Alex de Pfyffer and Ross Porter, co-founders of Heritage Holdings, about their journey to building an investment firm with nearly 50 acquisitions across 12 active platform companies. The conversation explores how they evaluated customer concentration and key-person risk in their first acquisition, why relationship-driven sourcing ultimately proved more effective than broad outreach, and how founder trust influenced transactions long before a Letter of Intent was signed. They also discuss building acquisition platforms, maintaining discipline on deal size, and partnering with founders through long-term ownership strategies.
