The What-If Gap

Uncertain middle ground between a conversation and a decision

Happy Thursday, 👋

A few months ago, we applied to participate in a venture conference. The application was submitted, the initial conversations seemed encouraging, and then came the waiting.

Waiting should be easy because there is technically nothing left to do. Rarely, however, is it passive. Once an opportunity begins to feel plausible, the mind starts filling in the missing pieces. We imagine the people we might meet, the introductions that might follow, and the momentum the event could create. Nothing has happened, but the possible future starts to feel surprisingly real.

When the rejection finally arrived, it was disappointing. It was also clarifying. The answer closed one path, ended the uncertainty around it, and allowed our attention to move elsewhere. What surprised us most was not the rejection itself, but what had happened during the gap between the last conversation and the final decision.

Founders live in this gap almost every day. They meet an investor and wait for a follow-up. They have a promising customer conversation and wait for the order. Each situation creates the possibility of a positive outcome, and that possibility can quietly influence what the founder does while waiting.

The Founder’s Advantage Can Become a Risk

Founders need the ability to imagine what does not yet exist. They must see a product before it is built, a market before it is obvious, and a company before there is much evidence that anyone else will believe in it.

That ability is one of a founder’s greatest advantages. It allows them to sell investors on a future that has not arrived and persuade customers to adopt a product that may still be evolving. During periods of uncertainty, however, the same power can become a risk. Once an investor appears interested, the founder can imagine the round closing. Once a customer asks for pricing or schedules a technical review, the founder can picture the contract being signed. The imagined outcome begins to feel close enough that behavior starts changing before the result is real.

George Loewenstein’s research on anticipation suggests people receive psychological value from thinking about a desirable future before it happens. The possibility itself can be rewarding. Most of us experience a simple version of this after buying a lottery ticket. We know the odds are terrible, yet during the period between purchasing the ticket and the drawing, we still find ourselves thinking about what we might do with the winnings.

Founders may be especially vulnerable to this effect because imagination is already part of the job. The challenge is not to eliminate hope but instead prevent hope from becoming the operating assumption of the startup.

When Possibility Starts Changing the Plan

There is an important difference between believing an opportunity may work and beginning to plan as though it will.

Consider a founder raising capital. After weeks of outreach, several investor meetings go well. One investor asks detailed questions. Another introduces a partner. A third says the company looks interesting and promises to follow up internally. The founder sees encouraging signs and begins to feel that the fundraising process is gaining traction.

Ironically, this can be the moment when fundraising momentum begins to slow.

The founder may reduce new investor outreach because the existing conversations feel promising. More time goes toward preparing for follow-up meetings and less toward expanding the top of the funnel. The team may begin discussing how the capital will be deployed, which hires will be made, or how quickly the company can accelerate once the round closes.

None of those thoughts are unreasonable. The problem is that the company’s behavior has started to change around capital that has not been committed. It’s the process of deciding which house to buy with your lottery winnings before the drawing happens.

Customer conversations create the same risk. We have seen founders slow or stop outbound sales activity because one large customer appeared close to signing a contract. The customer completed multiple meetings, brought senior executives into the discussion, and requested changes to the proposal. The probability of success seemed high enough that the founder shifted attention away from prospecting and toward implementation.

Then the contract stalled, the budget was frozen, or a new executive changed the priorities. The deal that felt almost certain disappeared, and the startup discovered that several weeks of new pipeline development had disappeared with it. The loss was both the contract and momentum while waiting for the decision.

The Gap

The period between engagement and decision deserves more attention because it can appear harmless. Work is still getting done, just not with the same urgency. It can feel a bit like trying to focus during the week before a long vacation. The calendar remains full, but our focus starts to shift.

The hidden danger is that a promising outcome can make creating additional options feel less necessary. One fewer investor email gets sent. A customer list is reviewed tomorrow instead of today. A marketing program is slowed because a large order appears close. No single decision seems consequential, but over time the changes compound and the company becomes increasingly dependent on an outcome it does not control.

Our minds are very good at filling in blanks during periods of uncertainty. Founders also tend to be inherently optimistic, so silence can be interpreted as continued interest and small signs of progress can feel more meaningful than they are. Optimism is still valuable, but it becomes dangerous when the possible outcome starts becoming the reason for making decisions.

Stick to the Original Plan

We are not suggesting everyone become a sudden pessimist. To attempt anything difficult, we must believe there is some chance of success. The better approach is to separate emotional optimism from operating discipline.

Before the uncertain outcome appeared, there was probably already a plan. A fundraising plan might call for contacting a certain number of investors each week. A sales plan might include a target number of outbound contacts, meetings, or proposals. Those activity levels were established before one conversation began to feel unusually promising.

A successful investor or customer meeting does not change the original plan. What changes is the founder’s perception of the need to keep following the plan. Recognizing this shift is important because perception of success can often become a powerful force even when the facts have not yet changed.

Buying a lottery ticket does not change our bank balance. We can enjoy imagining the possibilities, but we still get up the next morning and go to work. A promising investor discussion or customer meeting should be treated the same way. It may improve the odds, but it does not yet change the company’s resources.

Following the plan becomes most difficult when the finish line appears close. It can seem inefficient to keep calling investors when several are already engaged, or to continue customer outreach when a large contract looks days away from being signed. Yet this is precisely when maintaining the original pace matters most. The founder controls the process, but the final decision still belongs to someone else.

A simple discipline is to keep the activity targets unchanged until the outcome is real. Continue investor outreach until the capital is committed. Continue building the sales pipeline until the contract is signed. Prepare for the positive outcome, but do not allocate resources or reduce other activity based on an unsigned result. This protects the company if the opportunity disappears and creates more options if it succeeds.

Imagining the what-ifs is a normal and necessary part of building a company. The goal is to give those thoughts a boundary. What feels like a company-defining customer today may become one of many as the business grows. A million-dollar contract can be transformative for an early startup, but building the rest of the pipeline is what eventually makes that same contract less existential. Embrace what could happen, celebrate the possibility, and then return to the original plan.

Final Thoughts

Building a company requires living in what-ifs. Founders must believe customers will adopt something unfamiliar, employees will join something uncertain, and investors will fund a future that exists mostly in presentation slides and conviction.

It’s this imagination that powers a startup. During the gap between engagement and decision, it can also become a curse.

A few encouraging conversations can make the future feel close enough to touch. The temptation is to lean toward that future and reduce the effort required to create other options. Yet the period that feels most promising may also be the moment when operating discipline matters most.

The goal is not to become cynical or assume every opportunity will disappear. It is to keep an imagined outcome from replacing the original operating plan. Hope for the yes, prepare for the yes, but keep executing while the answer remains unknown.

Wishing everyone a great weekend,

-Eric.