If your business relies on one-time sales, every customer is a dead end. The transaction closes, the relationship ends, and you start over. You are hunting: tracking down one target at a time, consuming what you catch, and heading back into the forest for the next one.

Hunting works when the forest is full and you only need to eat today. But forests thin out. The easy targets disappear first, and each successive hunt takes more effort and covers more ground for the same yield. If every customer you acquire has to fund the acquisition of the next one from a single transaction, and acquisition costs don’t decrease as you exhaust the easiest-to-reach segments, the math never balances.

This is the death spiral of one-time sales. Acquisition costs are recurring, but revenue isn’t.

Marketing and Sales Are the Same Problem

Marketing and sales are the same problem. The goal of one determines the method and outcome of the other.

If your sales model is one-time purchases, your marketing must constantly find fresh customers. Every batch you acquire has to be replaced by the next batch, and you need the money from the current batch to fund finding the next one. When cash flow from one-time sales can’t keep pace with the cost of acquiring new customers, both marketing and sales collapse together. The math can work if you are hunting whales and each transaction is large enough to fund the next hunt, but most businesses aren’t operating in that market.

Subscriptions change the equation entirely. Each acquired customer keeps paying. In month one, 100 subscribers fund your marketing budget. By month six, 500 subscribers fund it. The math compounds in your favor instead of against you, and marketing shifts from desperate acquisition to retention and upsell.

The Expectation Trap

One-time purchases concentrate all customer expectation into a single transaction. A customer who pays $500 once expects the product to deliver everything they imagined at the moment of purchase. The bar is set at the point of sale, and it only goes up from there. You will struggle to reach what people expect of you when their entire investment happened in one moment.

Subscriptions distribute expectations across time. A customer paying $15 per month evaluates the product continuously against a lower threshold. Each month is an opportunity to deliver value, build trust, and demonstrate improvement. The relationship has room to grow because the stakes of any individual payment are low enough that customers stay through imperfection.

This also creates a natural path to upsell. A customer who started at $15 per month and gradually discovered they needed more is far more receptive to a premium tier than a customer who already paid $500 and feels shortchanged.

The low commitment cuts both ways, and that is a feature. Subscribers can leave, and that is one of the major reasons they sign up in the first place. The low barrier to exit is also a low barrier to entry. “We’ll make it up in volume” is the oldest self-deprecating joke in business, but with subscriptions it is actually true. People come and go as circumstances change, and many come back when circumstances change again. A one-time buyer who leaves is gone forever. A former subscriber is a warm lead who already knows your product.

Even Microsoft Figured This Out

If there was ever a company that could sustain one-time sales indefinitely, it was Microsoft. Office dominated the market for decades as boxed software. Businesses bought bulk licenses and individuals paid once per version. Microsoft had the brand, the distribution, the market share, and the switching costs to keep that model running longer than almost anyone else could.

They abandoned it anyway. The numbers tell you why: when Office 365 subscription revenue first surpassed perpetual license revenue, only about 10% of Office’s total user base was on subscriptions. Ten percent of users on a recurring model generated more revenue than the other 90% buying one-time licenses (Computerworld). That ratio alone tells you everything about why Microsoft made the shift and why the one-time model was already dead before they formally moved away from it.

If Microsoft looked at one-time licenses and decided the model wasn’t working, smaller companies don’t stand a chance trying to make it work.

Get Chickens First

The instinct for many businesses is to chase the big deal. Land the whale, close the enterprise contract, win the marquee client. That is big game hunting, and it has the same problem as all hunting: it’s unpredictable, resource-intensive, and doesn’t compound.

Start with chickens instead. Chickens aren’t glamorous and they don’t make for exciting board presentations, but they produce eggs every day without drama.

In practice, this means offering a cheap or free tier that the majority of users can access with minimal friction. Free for the 80%, affordable subscriptions for most of the rest, and premium pricing for the power users who need more. The cheap tier generates cash flow and builds a user base. The premium tier captures the customers who have already proven they need what you offer.

And chickens don’t just lay eggs; they produce more chickens. Subscribers are better referral sources than one-time buyers for reasons that compound on each other. A one-time buyer disappears after the transaction, but a subscriber stays connected, which means you can involve them in polls, feedback loops, and community conversations that deepen their investment in the product. That involvement creates satisfaction that goes beyond the product itself; people advocate for things they feel part of, not things they bought once.

The low price point also makes referrals frictionless. “Try this, it’s $15 a month” is a far easier recommendation to make than “you should spend $500 on this.” And if you build a community culture around your subscriber base, you create advocates who do your marketing for free because they genuinely want others to share the experience. Your customers become your marketing engine, and that referral channel costs you nothing. Hunting never gets cheaper. Chickens compound.

With chickens producing steady cash flow, you can pursue big game selectively. Enterprise deals and high-value contracts become supplemental wins rather than survival necessities. When you aren’t desperate, you negotiate better, qualify opportunities more carefully, and walk away from deals that don’t fit. Big game is rarer and more valuable precisely because you don’t need it to keep the lights on.

The Long Term Only Arrives if the Short Term Doesn’t Kill You

One-time sales feel like progress because money arrives in visible chunks. But each sale is a dead end that resets the clock, and the short term is self-serving enough to consume every resource you have before the long-term strategy ever materializes.

Not every business can make this shift, and I won’t pretend to understand every nuance of every market well enough to make a universal claim. But for software and repeatable services, the math is unambiguous. Sell it cheap if you must. A $10 subscription that renews every month is worth more than a $200 one-time sale by month 21, and the customer relationship is still alive. The early months will be lean, but a one-time sales business at month 12 is in the same position it was in at month 1 while a subscription business at month 12 has compounding revenue and a customer base that makes the company worth acquiring if you ever want that option. Subscriptions solve the cash flow problem, the marketing sustainability problem, and the customer expectation problem simultaneously. They turn every customer from a dead end into a compounding asset.

Get chickens, let them lay eggs, and then go hunt big game when you can afford to be selective about it.