Exiting a business is not a dramatic movie scene with violins and confetti. It is more like tidying a workshop after a long project, deciding which tools to keep at arm’s reach and which to store away. For a holding company, the decision to exit is not about winning or losing.
It is about whether the asset still serves the mission, the people, and the future. The trick is to use crisp criteria, keep our emotions on a short leash, and accept that every dollar and every hour could be doing better work somewhere else.
We care about return on capital, but we also care about return on time. Capital can compound in a spreadsheet. Time compounds in experience, focus, and energy. If a business consumes huge amounts of attention yet grows like a sleepy houseplant, it fails a key test.
The companion test is risk. Not the theoretical kind that lives in footnotes, the practical kind that sloshes through payroll season, regulatory shifts, and customer concentration. When time and risk are mispriced, an exit conversation is not only appropriate, it is overdue.
A business can be perfectly healthy and still be wrong for the portfolio. Maybe our direction changed, or the company’s market did. We ask whether the asset still supports our core capabilities, our brand promise, and our flywheel of shared services. If the answer is a polite shrug, that is a signal. Strategy is not a museum; it is a living map. Assets that no longer belong on that map get a bright circle and a calendar date for a serious review.
Every operation has momentum. Some glide with tailwinds from network effects, cost advantages, or irreplaceable relationships. Others push a grocery cart with one squeaky wheel. We look for compounding advantages, even small ones. A loyal niche can be a moat.
A small recurring upsell can be a moat. If nothing is compounding, and every inch of progress feels like a trench, then we are not building a castle, we are building a treadmill. Treadmills are fine at the gym, not in the portfolio.
Revenue is charming. Margins tell the truth. We underwrite unit economics as if the weather turns gray for a while. Are we profitable after fully loaded costs, not just the flattering ones? Does growth improve cash conversion, or does growth devour it?
If the business makes money in fair weather but needs heroic assumptions when the forecast shifts, we put away the hero cape and rework the plan. If rework cannot produce durable economics, that is a strong exit cue.
A tired team can keep the lights on, yet it cannot light a fire. We pay attention to morale, succession depth, and the ratio of problem solving to problem reliving. If leadership attention is constantly borrowed from healthier businesses, the borrowing cost is invisible but steep.
We also ask whether the team has a meaningful path to win. If the best available path leads through more churn, more reactivity, and more midnight emails, we owe our people something better than endurance.
We do not wait for a perfect dataset. We watch for clusters of signals. Persistent misses against realistic forecasts. Customer churn that rises after hard-won wins. A sales pipeline that grows in meetings but not in money. Vendor terms that tighten when cash is already tight.
A market where competitors set the pace and we jog to keep up. No single signal decides the future. The pattern does. When enough signals point in the same direction, we schedule the conversation that every operator secretly knows is coming.
We start with a pre-mortem. If we keep this business for two more years and it fails, what did we miss today? That clears the fog of optimism. Then we run a bare-bones model with conservative inputs. We compare the business against a credible alternative use of the capital and, crucially, the people. The same diligence we use for acquisitions applies here.
We solicit candid views from those closest to the customer and from those who only see the numbers. The meeting is not a courtroom. It is a workshop. At the end, we ask a plain question: would we buy this asset today at its implied hold price? If not, the answer is already visible.
Exits should feel like closing a well-organized toolbox. We gather documentation, document daily rhythms, and list the three vital relationships that must be handled with care. We map the handoff plan by calendar week, not wishful thinking. We simplify pricing and service terms where possible so the buyer can understand the value quickly. We remove pet projects that only make sense to us. A clean handoff makes the asset easier to love, and easier to value fairly.
An exit is a human event dressed in financial clothing. We communicate early with managers, then with teams, then with key partners. We avoid surprises. We define retention needs and severance plans with decency and clarity.
We preserve reputations because reputations are assets. We keep obligations we can keep, and we are honest about those we cannot. The way we exit one business is the way future sellers and employees expect we will behave in the next one. That memory compounds.
Sometimes the exit file goes back in the drawer. A business may have ugly headlines but beautiful fundamentals. Maybe the cost structure is fixable with one brave decision. Maybe customer love is strong, even if conversion is not. We hold when the moat is real, even if it is muddy.
We hold when a specific operational change has clear math behind it and a leader who will own it. We hold when alternative uses of capital look shiny yet flimsy. Holding is not inaction. It is a decision with its own discipline, its own calendar, and its own scorecard.
Owners fall in love with narratives. We remember the first big customer. We remember the month the graph turned up and to the right. Nostalgia is warm, but it can be expensive. We remind ourselves that businesses are not children and we are not failing them by choosing a better home.
The right buyer might unlock value we never could. Letting go can feel like selling a beloved car, but if someone else will drive it farther and faster, the honest choice is to hand over the keys with gratitude and move on.
Exiting a business is not quitting, it is curating. We keep what fits the plan and serves the people. We part with what drains attention, misprices risk, or simply belongs in someone else’s story. The work is rigorous and sometimes uncomfortable, yet it pays in clarity and momentum. Decide with clean criteria, run a thoughtful process, protect the humans, and let the portfolio breathe. That is how exits stop feeling like endings and start feeling like progress.
Ryan Schwab serves as Chief Revenue Officer at HOLD.co, where he leads all revenue generation, business development, and growth strategy efforts. With a proven track record in scaling technology, media, and services businesses, Ryan focuses on driving top-line performance across HOLD.co’s portfolio through disciplined sales systems, strategic partnerships, and AI-driven marketing automation. Prior to joining HOLD.co, Ryan held senior leadership roles in high-growth companies, where he built and led revenue teams, developed go-to-market strategies, and spearheaded digital transformation initiatives. His approach blends data-driven decision-making with deep market insight to fuel sustainable, scalable growth.
