Chapter 9

The Best Buyer You Can't Reach Is a Bad First Buyer

Reachability Is a Commercial Variable

Reachability sounds like a marketing problem until you realize it can change which market is commercially useful to you.

Suppose you identify a buyer who appears nearly perfect. The problem is expensive. The organization has money. The person you want has authority. There is a plausible reason to act now. You can find their name, title, company, email address, LinkedIn profile, and perhaps a surprising amount of information about what they ate at a conference three years ago.

That does not necessarily mean you can reach them.

I am using reach here in a stricter sense than obtaining contact information. A prospecting database can give you an email address. That is useful infrastructure. It is not the same thing as having a credible path to a commercial conversation.

The distinction matters because we often measure accessibility technologically. Can I find the company? Yes. Can I identify the role? Yes.

Can I obtain an email address? Probably.

Can I send a message?

Absolutely. Modern software has made sending messages to strangers one of the least technically constrained activities available to civilization.

But the commercial question is different:

Can I create a situation in which this particular buyer is reasonably likely to give the problem serious attention?

That is a much higher bar.

A founder can technically contact ten thousand people and have almost no practical access to the market. The messages arrive in inboxes already competing with vendors, recruiters, internal requests, newsletters, automated follow-ups, calendar changes, security warnings, expense reminders, and several emails whose subject lines insist that they are the recipient’s final opportunity to do something nobody remembers asking to do.

The message being delivered is not the same thing as the buyer being reached. This is where early market selection gets more interesting than building a list of companies that fit your ICP.

Imagine two buyer groups.

Buyer Group A has problems worth perhaps ten times more than Buyer Group B. The contracts could be much larger. The organizations are recognizable. If the product succeeds there, the long-term economics look excellent.

But you know nobody in Group A.

You have no existing customers resembling them. Nobody who works with them is willing to introduce you. You do not yet have a reputation in their professional community. When you contact them, you are one unknown vendor among many.

Buyer Group B has smaller contracts. The pain is still meaningful, but the total dollars are lower. However, you have worked in their industry. You know several people who perform the workflow. A former colleague can introduce you to two owners. You belong to a professional group where these people already discuss the problem. One prospective buyer has agreed to look at what you built.

Which market is better? For the eventual company, I do not know. For obtaining high-quality evidence next week, I have a strong preference. The second group can answer questions the first group currently cannot because the first group is not participating in the experiment.

This is an important correction to how we normally think about market attractiveness. We tend to imagine buyer characteristics as belonging entirely to the buyer.

They have the problem. They have the budget. They have authority. They have urgency. Reachability is different because it exists partly in the relationship between you and the buyer. The same buyer can be highly reachable to one founder and nearly inaccessible to another.

A founder who spent ten years working with regional accounting firms may be able to get five serious conversations with firm owners in a week. I could build the identical product, target the identical firms, write equally competent outreach, and struggle to get one.

Nothing about the buyers changed. The access path did. The reverse could be true in another market where my own professional relationships, credibility, or experience create a more natural opening.

That makes reachability an awkward variable for market-sizing exercises because it is not cleanly contained in the market. You cannot look at an industry report and find a column labeled Probability Oliver Gets a Meaningful Conversation.

Unfortunately, that column matters early.

I want to be careful not to overstate this. Reachability does not make a weak buyer strong.

If your cousin owns a company and will answer every call you make, that is wonderful access. If his company does not have the problem, cannot pay, or has no reason to change, easy conversation does not magically create a market.

Likewise, I would not abandon a genuinely attractive market simply because the first twenty cold messages were ignored. As we established earlier, silence does not tell you enough to make that conclusion. Your message may be poor. Your contact may be wrong. Your timing may be bad. You may have chosen a channel the buyer barely notices.

Reachability is not a binary label that says reachable or unreachable forever. It is a constraint to include in the hypothesis. That changes the way I think about early buyer selection.

Instead of asking only, “Who would benefit most from this product?” I also want to ask, “Among the people who could plausibly buy this, where can I actually get close enough to observe a buying decision?”

Those are different questions.

The second one becomes especially important when you have little commercial evidence. If your assumptions about buyer, urgency, price, value, or implementation are wrong, you need interactions capable of exposing that quickly. A market that gives you one serious conversation every two months creates a very slow learning loop.

You can spend six months with almost no idea whether your theory is improving.

This is one reason early founders can appear incredibly busy while their commercial evidence barely changes. They build enormous prospect lists. They enrich records. They automate sequences. They send hundreds of messages. They optimize subject lines. They move contacts through CRM stages with admirable administrative precision.

And still, very few qualified buyers ever seriously evaluate the proposition. The activity is real.

The access is weak.

I do not want to turn this chapter into a discussion of acquisition channels. That comes later. At this point, the issue is more basic than whether you should use outbound, content, partnerships, search, communities, events, or something else.

Before choosing how to scale access, notice whether access exists at all. Can you name several plausible buyers with whom you could realistically have a substantive conversation? Can you get close enough to ask what they do today, show them the product, put a real price in front of them, hear the objection, and ask for the next appropriate commitment? If the answer is yes, you have something valuable even before you have a customer. You have a place where commercial learning can happen.

If the answer is no, the market may still be attractive. But your evidence from that market is likely to arrive slowly, and your ability to distinguish a bad buyer hypothesis from a bad access path will remain limited.

There is also one more complication. Getting the conversation does not mean the buyer will believe you. You can be completely reachable and still be commercially distant.

That distance is trust.

First Buyer Versus Eventual Market

The buyer you want first is not necessarily the buyer you want most.

That distinction sounds obvious once stated. In practice, founders blur it constantly.

They choose a market by asking where the largest budgets are, where the most painful problems exist, or which customers would make the company look most credible. Those are reasonable questions when designing the eventual business.

They are not always the right questions when choosing where to begin. Your first market has a different job. It has to give you evidence.

You need buyers close enough to the problem to tell you whether your understanding is accurate, reachable enough to engage, authorized enough to act, and commercially serious enough to make the conversation matter. Ideally, some of them can move from interest to evaluation to payment without requiring your company to become something it cannot yet be.

That can lead you toward a market that looks smaller than your eventual opportunity. This is not the same as deciding to build a small business. It is deciding the order in which you learn.

Suppose you build software that helps large organizations detect expensive operational problems. Your long-term market may genuinely be companies with thousands of employees and complex systems. The economics might be excellent. A successful deployment could justify a six-figure annual contract.

But today you have no references in that category, no established enterprise sales motion, and no realistic way to get through a nine-month purchasing process without first proving the product somewhere. There may be a smaller version of the same problem in companies that can evaluate the product in weeks. Those customers may never justify your eventual enterprise price. That does not make them irrelevant. They may let you discover which part of the product buyers actually care about, what language they use for the problem, which objections appear repeatedly, which implementation burden matters, what results they need to see, and what they will pay before you spend a year discovering those things one enterprise meeting at a time.

The smaller market can be commercially useful without being strategically permanent. This is one of those areas where ambition gets in the way of sequencing. A founder says, “I don’t want to sell to small companies.” Fine. You do not have to build the company around them.

But if three smaller customers can give you the evidence required to become credible with the larger customer you actually want, refusing to learn from them because they do not match the eventual vision is a strange form of discipline. The first customer does not have to define the last customer. There is a danger in the other direction too. Some founders get traction with an accessible market and assume that market must therefore be the business. It does not. A customer group can be excellent for learning and poor for scale.

Perhaps the buyers are easy to reach but their budgets are tiny. Perhaps churn is structurally high. Perhaps supporting them requires too much labor. Perhaps the problem is real but not valuable enough to support the economics you eventually need.

Early traction is evidence. It is not a lifetime commitment. This is why I prefer to separate two questions.

First:

Where could this become a strong business?

Second:

Where can I learn enough to determine whether I deserve to pursue that business?

Sometimes the answer is the same market. That is ideal.

You have a buyer with meaningful economic pain, sufficient budget, reasonable access, manageable trust requirements, and a short enough path to a real decision. Nothing says your first market has to be small.

If you already have deep relationships inside large organizations, recognized expertise in the field, an internal champion, and a plausible procurement path, enterprise may be exactly where you should begin. The point is not “start small.” The point is “start where evidence can move.”

That difference matters.

A five-person company is not automatically a good first customer simply because the owner answers email. A Fortune 500 company is not automatically a bad one because it has procurement.

The useful comparison is between the commercial value of the buyer and the amount of friction between your current position and a meaningful buying decision. Early on, I am willing to trade some theoretical contract value for a much shorter path to evidence. Not forever. Long enough to learn. This can also prevent premature product distortion.

Imagine you target your eventual enterprise market from day one. Every conversation surfaces something an enterprise might eventually require.

Advanced permissions. Custom reporting. Multiple approval layers. Centralized administration. Special deployment options.

Security controls. Integration requests. You may need all of them eventually. But if the organization is still six months from being able to buy, it becomes difficult to know which requests are genuine commercial requirements and which are simply characteristics of an enterprise evaluation.

A more accessible buyer can force a cleaner question:

Does the core thing create enough value that someone will pay for it? That answer is useful before you build the machinery required to serve your eventual market at scale. There is no virtue in winning small customers merely because they are easier. There is also no virtue in choosing the hardest possible customer because success there would feel more impressive. Prestige is not evidence.

The useful first buyer sits somewhere between trivial accessibility and impossible ambition. They have a real problem. The problem matters economically. They can act. You can reach them.

The amount of trust required is within range. The organizational path to a decision is understandable. And if they say yes or no, you learn something you can use. That last part is easy to overlook.

A first buyer is valuable not only because of the revenue they might produce. They are valuable because they compress the distance between assumption and reality.

Once you start thinking about market entry this way, another question follows naturally. If your eventual buyers are not yet directly accessible, how do you get close enough to the right early buyers to learn? You need a credible access path.

Credible Access Paths

Reachability is not only a property of the buyer. It is also a property of the path.

That path can be direct or indirect, formal or informal, obvious or slightly accidental. What matters is that it gives the buyer a reason to give you enough attention for a real commercial interaction to occur.

A cold email can be a credible access path. So can a former colleague. So can a trusted partner, a professional community, a customer referral, a conference conversation, a piece of work that establishes relevant expertise, or a relationship you already have from another context. The specific route matters less here than the principle. The buyer should encounter you in a way that makes evaluation plausible.

That is different from merely being able to deliver a message. Consider two founders selling essentially the same product into the same industry.

The first has spent years working with the people who now constitute the target market. They know the language, the workflows, the constraints, and several of the people involved. When they ask someone to look at the product, the request arrives with context.

The second founder knows the market only through research. They may understand the problem well. Their product may even be better. But every conversation begins from zero.

The second founder is not necessarily in the wrong market. They simply have a longer path. That difference should affect how we evaluate the opportunity.

Founders are often encouraged to think in terms of total addressable market, segment size, growth rate, average contract value, and competitive intensity. Those are useful variables.

For an early company, I would add another:

How does the first credible conversation happen?

Not the thousandth. The first. If you cannot answer that question at all, you do not yet have a complete market-entry hypothesis. That does not mean you need an existing network.

Cold outreach works. Public work can create credibility. Communities can create proximity. Partners can create introductions. A narrowly useful product can sometimes earn attention on its own.

Access can be built. But “we can probably figure out how to reach them later” should not receive the same weight as an access path that already has some evidence behind it. This is where founders sometimes mistake the existence of a channel for the existence of access. LinkedIn exists. Email exists.

Conferences exist. Ads exist. Search exists. That does not tell you whether any of them will put you in a serious conversation with the buyer you have selected. A channel is infrastructure.

An access path is a plausible sequence from your current position to buyer attention. Those are not the same thing. Suppose your target buyer is a chief compliance officer at a large financial institution.

You can find thousands of them online. You can send messages. You can publish content. You can buy ads.

But if none of those actions has yet produced meaningful interaction, your current access path remains uncertain. Now suppose a cybersecurity consulting firm already advises ten of those institutions and is willing to introduce your product where it fits. The buyer did not change. The path did. And because the path changed, the commercial usefulness of that market changed with it.

This is why relationships can matter without turning the lesson into “network more.” A relationship is useful only when it reduces uncertainty between you and a relevant buyer. Knowing many people is not the same as having access to buyers.

Likewise, an introduction is not valuable merely because someone agreed to make it. If the person receiving it has no reason to care about the problem, the introduction gives you proximity without commercial relevance.

The path has to connect to the right decision. There is also a difference between borrowed credibility and borrowed demand. A trusted person can get you into the room. They cannot make the buyer need the product. A respected partner can reduce some trust distance.

They cannot manufacture urgency. A strong personal reputation can earn attention. It cannot rescue an offer that does not matter. This boundary is important because founders can overvalue warm access just as easily as they undervalue it. A friend who introduces you to a senior executive may feel like a breakthrough.

It might be. But if the executive is not close to the problem, has no reason to evaluate the product, or politely agrees to a demo as a favor, the evidence remains weak. The purpose of access is not to collect meetings. It is to reach buyers under conditions where their behavior can teach you something. That means the best access paths often have a useful kind of specificity.

You know who the buyer is. You know why the problem is relevant. You know why the conversation is occurring. And there is a plausible next commercial step if the buyer cares. That might be a deeper evaluation.

A pilot. A price discussion. An introduction to the person who owns the budget. A commitment to test the product on a real workflow. The exact step depends on the product and market.

What matters is that the path can continue. A meeting that has no believable route to a decision is better than no meeting, but it should not be mistaken for commercial access. This becomes particularly important when comparing markets. Suppose Market A appears twice as valuable on paper but you have no idea how to get beyond mass outreach. Market B has smaller contracts, but you can already identify ten relevant buyers, get into serious conversations with several of them, and ask for real commitments. The correct choice is not automatically Market B.

But Market B has something Market A currently lacks:

A working mechanism for turning assumptions into evidence. That mechanism has value. Especially early. You can expand a market later. You can build credibility later.

You can develop additional channels later. You can move into larger customers later. What is much harder is learning anything from a market that never meaningfully interacts with you. So before I become attached to a segment, I want to know more than whether the buyers look good on paper. I want to know whether there is a believable path from where I stand today to a buying conversation.

Once that path exists, we can evaluate the buyer more rigorously. Not just for pain and budget, but for whether they are a useful early commercial target at all.

Choose for Learning Velocity

A first market does not need to be easy. It needs to be informative. Those are not the same thing.

An easy buyer may say yes quickly because the purchase is trivial. That can feel encouraging while teaching you very little about whether the product solves an important problem.

A difficult buyer may produce the opposite problem. The commercial value may be obvious, but the path to a decision is so long that months pass before you learn whether the buyer will actually commit.

What I want early is a buyer who can return meaningful evidence at a useful speed. That is learning velocity. The idea is simple: how quickly can this market turn your assumptions into observable buyer behavior? Not opinions. Not compliments.

Not impressions from people who think the product is interesting. Behavior. Will they take the meeting? Will they show you the real workflow? Will they introduce the person who owns the budget?

Will they evaluate the product with actual data? Will they accept the price? Will they agree to a dated pilot? Will they pay? Each step reduces a different kind of uncertainty.

The faster you can move through those steps with relevant buyers, the faster you can tell whether the commercial hypothesis deserves more investment. This is one reason the biggest market is not always the best place to start.

Imagine two segments.

Segment A could eventually support $100,000 annual contracts. It takes six weeks to get the first serious conversation, another month to identify the right internal owner, and several months after that to reach a decision.

Segment B could support $12,000 annual contracts. You can speak with five qualified buyers this month. Two will let you observe their current process. One can authorize a paid pilot without a committee.

I am not saying Segment B is the better business. I am saying it is capable of producing commercial information much faster. That information may eventually help you win Segment A. Or it may tell you that the product is not nearly as valuable as you believed, which is also useful. Founders sometimes resist this because learning sounds less important than revenue.

Revenue is better. But before reliable revenue exists, learning is what improves your chances of finding it. The problem is that not all learning is equally valuable. You can spend a month conducting interviews and emerge with fifty pages of notes that change no decision. You can spend the same month putting a real offer in front of ten qualified buyers and discover that eight reject the price for the same reason.

The second month may feel worse. It is probably more useful. Learning velocity therefore depends on both speed and quality of evidence. A market that gives you rapid but weak feedback can be deceptive.

If hundreds of people happily sign up for a free product, you have learned something about interest and perhaps utility. You have not necessarily learned whether the business works.

A market that produces one purchasing decision every six months has the opposite problem. The evidence may be excellent, but the feedback loop is painfully slow.

The useful early market sits somewhere between those extremes. You can reach enough relevant buyers. The problem matters enough that they will engage seriously. The buying process is short enough to observe commitment. And the decisions they make are meaningful enough to change what you believe.

That final condition matters.

Commercial learning is not collecting reactions. It is reducing uncertainty in a way that affects the next decision.

Suppose you believe operations managers at small manufacturers will pay $500 a month for your application. You speak with twelve of them. Eight describe the problem as expensive. Four agree to evaluate the product. Two tell you $500 is reasonable.

One agrees to a paid pilot beginning next month. That sequence has changed your knowledge.

You still have enormous uncertainty. One pilot does not prove a market.

But you now know substantially more than you did when the product existed only as a founder hypothesis. Now imagine instead that you spend the same period trying to reach vice presidents at global manufacturers. You send hundreds of messages. One assistant forwards your note. Two people accept LinkedIn connections.

Someone tells you the idea sounds interesting. You may have performed far more commercial activity while learning less. This is why volume can be such a misleading comfort. A large number of attempts does not guarantee a large amount of information. The relevant unit is not activity.

It is evidence returned per unit of time and effort. That is the lens I would use when choosing between plausible early markets. Which buyer can I actually get in front of? Which one can evaluate the product under realistic conditions? Which one can expose whether the pain is strong enough to act?

Which one can make or influence a financial commitment? Which one can tell me something meaningful soon enough that I can still change course? The answer may not be your most glamorous buyer. Good. Prestige is expensive when you are still wrong about important things.

There is also a psychological advantage to faster commercial feedback. Long feedback loops give founders room to tell themselves stories. The enterprise prospect is still interested. The timing is just difficult. The budget will open next quarter.

The executive has been busy. Security is taking longer than expected. The champion sounded enthusiastic. Any of those explanations may be true. The problem is that several months can pass while nothing forces the underlying hypothesis to become more precise.

Shorter learning loops are less forgiving. A buyer either takes the next step or does not. A price either survives contact with the market or it does not. A pilot either becomes dated and real or remains conversational. The evidence is not always pleasant, but it is harder to romanticize.

That is valuable. You do not need every customer to be easy to reach forever. You do not need to avoid complex organizations. You do not need to optimize the entire company around whatever buyer gives you the fastest first sale. You need enough commercial contact with reality that your strategy stops being protected by distance.

That is what a good first market gives you. Not certainty. Not proof that the company will succeed. A faster way to become less wrong. So when two markets both appear attractive, I would not ask only which one is larger.

I would ask which one can return stronger evidence sooner. When two buyers both have real pain, I would not ask only who could eventually pay more. I would ask which one can move far enough through the buying process to teach me something now. And when a founder tells me they have identified the perfect customer, I want to know whether that customer is close enough to make a decision. Because until buyers begin making decisions, nearly everything about the commercial side is still a hypothesis.

The product has had its vote. The founder has certainly had theirs.

Now the market gets one.