Why the Hardest Markets Come With the Strongest Moats

Conventional wisdom on market selection rewards speed over staying power. Founders are told to look for an obvious buyer and a short sales cycle, because both lead to early revenue, and early revenue is what most boards and investors want to see first.

However, after twenty years inside healthcare, I’ve watched well-built companies stall while patient ones grow, and the pattern has become difficult to miss. The markets everyone avoids end up protecting the companies willing to learn them, and the difficulty everyone complains about turns out to be the most durable competitive advantage.

This is not a romantic argument for suffering. Plenty of companies walk into hard markets and die there, usually with strong products and hard-working teams. The difference between the companies protected by complexity and the companies killed by it has little to do with product quality and nearly everything to do with whether anyone studied the market’s structure before deploying capital against a well-informed strategy. The moat prizes residents and drowns tourists, and both walk in through the same gate.

The advice holds up until you price it

An easy market gives you validation fast, with revenue settling the argument before the next board meeting. What rarely gets priced is the other side of the ledger. Every condition making a market easy for you makes it equally easy for whoever comes next. Competitors show up fast, features converge faster, and before long, price is the only argument left. The speed of validation and the speed of commoditization are the same speed.

The market’s founders get warned away from behaving in reverse. Healthcare, government contracting, financial services and defense all share long procurement cycles, buying committees, and regulators with opinions. They are miserable to enter. Once you earn your place, few competitors can take it from you.

Healthcare makes the case in its most extreme form

Take a typical hospital purchase. The doctor or nurse using the product usually isn’t the one paying for it, and one person almost never signs off alone. HIMSS finds that nearly 60% of organizations involve five or more people in technology purchases, including 23% with buying teams of ten or more. Budgets get set by the quarter. And regulation touches nearly everything, for good reasons, like patient safety, privacy and clinical accountability.

Founders coming from software often find all of this maddening. They see a broken system. I see a system doing what it was built to do, which is keeping out companies that haven’t prepared.

AI in radiology shows what happens when you ignore this. The algorithms read scans better than the baseline, and hospitals saw real-time savings. Adoption is still stalled. 

I had Sunny Kumar, a partner at GSR Ventures, on the Outcomes Rocket podcast, and he’s watched this happen from the investor side more than once. His view is simple: strong technology without go-to-market discipline tends not to “never take off.” With radiology AI, nobody figured out what each person in the deal needed. The physician wanted one thing, the finance lead wanted another, and the payer and the patient each had their own priorities. Nobody agreed on what success meant.

I coached teams through these buying patterns when I was running the Healthcast commercial business at Medtronic. FDA clearance secured, clinicians genuinely enthusiastic, a committed champion inside a large health system, and the deal still sat for nine months in front of a value analysis committee nobody had budgeted for. 

The plan had prepared one argument when the sale required three: reimbursement for the payer, institutional return for the hospital and workflow fit for the clinician. The product was never the problem. How our team positioned the technology across the various stakeholders eventually unlocked the opportunity and got us the win.

Complexity filters out most of your competition

This is the part I wish more founders understood. Complexity kills the underprepared, and the underprepared make up most of the competition in any complex market. My firm’s 2026 State of B2B Go-to-Market report surveyed 511 B2B professionals across the U.S. and the U.K. Only 37% treat go-to-market as one integrated revenue framework, and 21% have no defined owner for it. Roughly 24% of go-to-market spend traces back to no commercial outcome at all.

Effectively, nearly a quarter of the go-to-market budget gets allocated with no line back to revenue. From a critic’s seat, that is a waste. From a competitor’s seat, it is an opening. If your competitors are like that survey, ~25% of the money deployed against you is being spent by teams borrowing plays from easier industries and blaming the market when nothing converts.  If you are deploying GTM capital and effort that way, you no longer have an excuse, and the opportunity for you to gain an advantage is possible. 

What crossing the market moat looks like

Three practices separate the companies that cross from the companies that drown.

1. Write the strategy down, communicate it and confirm understanding and alignment. A written plan everyone follows beats a brilliant one sitting in one executive’s head. A good one covers the personas and ICPs, every buyer in the deal and what each one cares about, the main decision cycles, where those buyers spend their time, and how the product solves their specific problems. The important part is keeping it in use after the person who wrote it leaves. These sales cycles often run longer than people stay in their jobs.

2. Map every yes. Every person who needs to approve the deal goes on paper. If there are fewer than five names, someone’s usually missing. For each person, write two sentences: what would get them promoted, and what would get them blamed. If you have both answers for everyone, you understand the deal. If you don’t, you have a good relationship, and good relationships are where a lot of healthcare deals start, but also quietly stall.

3. Put the gates in the timeline. Evaluation periods, compliance reviews, and committee approvals are stages of the sale. Give each one an owner, an evidence package and its own success criteria before the sale begins. Teams treating these gates as an afterthought lose months they never budgeted for, deals are improperly forecasted, and, in a long cycle, stalled momentum rarely comes back.

Years ago, Peter Senge, senior lecturer at the MIT Sloan School of Management, co-founder of the Center for Systems Awareness, wrote, “Today’s problems come from yesterday’s solutions.” The structures slowing you down were built for reasons, and no pitch deck makes them disappear.

You have a choice. You keep running the playbook from easier markets with more effort and keep wondering why it doesn’t convert, or you learn how this market buys and build your approach around it.

Conventional wisdom on market selection rewards speed over staying power. Founders are told to look for an obvious buyer and a short sales cycle, because both lead to early revenue, and early revenue is what most boards and investors want to see first.

However, after twenty years inside healthcare, I’ve watched well-built companies stall while patient ones grow, and the pattern has become difficult to miss. The markets everyone avoids end up protecting the companies willing to learn them, and the difficulty everyone complains about turns out to be the most durable competitive advantage.

This is not a romantic argument for suffering. Plenty of companies walk into hard markets and die there, usually with strong products and hard-working teams. The difference between the companies protected by complexity and the companies killed by it has little to do with product quality and nearly everything to do with whether anyone studied the market’s structure before deploying capital against a well-informed strategy. The moat prizes residents and drowns tourists, and both walk in through the same gate.