The first ninety days after closing are when the 75% regret statistic becomes real. Most exit planning ignores this phase entirely. Here's what actually happens—and how to navigate it without losing yourself.

The Second-Bite Trap catches founders who accept deal structures that look like an opportunity but function as a constraint. Earnouts and rollovers can work beautifully—or lock you into years of golden handcuffs.

Most founders treat exit planning as a transaction to optimize. The Exit Blueprint approach starts with where you're going, not what you're leaving—building a business that's attractive to buyers AND serves your specific goals.

Most founders prepare the business but not themselves. The Clarity Gap—lacking a clear post-exit vision—affects every decision during the exit and explains why 75% of founders regret selling within a year.

The Individual Hero Problem happens when high-performing functional leaders optimize for their own metrics at the expense of collective outcomes. The result is a team where everyone hits their numbers—but the company underperforms.

The Assumed Alignment Trap happens when leadership teams believe they share values because they've never explicitly tested it. Then a hard decision comes along, and suddenly it's clear that people have fundamentally different ideas about what matters.

The Nice Team Problem happens when leadership teams prioritize politeness over productive conflict. The debates that should happen in the meeting room happen in the hallway instead—or not at all. Building a team that fights well is the key to decisions that stick.

The Consensus Trap happens when leadership teams pursue agreement from everyone instead of clarity about who actually decides. Clear decision rights beat unanimous agreement every time—and they let you move at the speed your business requires.

The Peer Pressure Gap is the pattern where leadership team members hold their direct reports accountable but won't call out their peers. When all accountability flows through the founder, you've built a hub-and-spoke team that can't scale.

The Blurry Boundaries Problem happens when roles are defined by title or department but not by clear accountability for specific outcomes. The symptoms don't look like a "roles" problem—they look like missed deadlines, duplicated effort, and finger-pointing when things go wrong.

The Founder's Shadow is the pattern where culture exists only because the founder maintains it. The team is great, the standards are high, but it all flows through one person. Buyers see this as risk—and founders who can't let go of their cultural attachment often struggle with exit. Building transferable culture requires ego work as much as systems work.

The Firefighting Trap catches founders who pride themselves on getting things done. But if progress depends on your constant attention, you don't have a business that runs—you have a business you push. Buyers want systems that execute without founder heroics, and building those rhythms is what makes a company transferable.

The Concentration Curse hits founders who've done everything right—landed major accounts, built deep relationships, delivered great work. But when one client represents 20% or more of revenue, buyers see dependency, not success. Diversification takes 12-24 months, which is why this is one of the first things to address in exit planning.

The Rainmaker Risk is one of the most common valuation killers in exit planning. When the founder is the primary sales engine, buyers see a business that can't sustain revenue after the transaction closes. Building transferable sales systems isn't optional—it's what makes your company worth buying.

Founders who know every detail of last year's financials often freeze when buyers ask about next year's projections. This gap between historical clarity and forward visibility—the Rearview Mirror Problem—is one of the most common reasons deals fall apart or valuations get discounted.

Most founders don't realize their lack of documentation is a valuation problem until buyers start asking questions. The Tribal Knowledge Trap—where operations work only because specific people know how to make them work—creates risk that acquirers price into every offer.

The Values Poster Problem happens when founders create values that sound inspiring but don't differentiate or drive behavior. If your values could belong to any company, they're not doing their job. Real values require trade-offs—and the willingness to hire, fire, and make hard decisions based on them.

The Runway Blindspot hits founders who confuse a profitable P&L with a healthy business. Growth consumes cash—often faster than profit generates it. Without understanding your capital requirements, you can scale yourself broke while celebrating record revenue.

The Accountability Illusion happens when founders distribute ownership so broadly that no one feels truly responsible. Commitments get made, deadlines pass, and somehow no one is on the hook. The real cost isn't missed deliverables—it's a culture where promises stop meaning anything.

The instincts that got you here won't get you there. The Gut Instinct Gap is the pattern where founders keep making strategic decisions the way they always have—fast, intuitive, from the gut—long after the company needs something more rigorous.