Asher's Blog

I have not met a successful founder who was less optimistic about the company’s future than the average member of the team.

That does not mean founders are cheerful every day. It does not mean they are blind to risk, untouched by anxiety or permanently certain about every decision. It means that beneath the changing emotions, they carry a persistent belief that progress is possible and that their actions can help produce it.

This is one of the founder’s greatest advantages. You start a company because you believe something can be better than it is today. You hire people because you believe the work can become larger than what you can do alone. You build a product because you believe customers will eventually choose it. You raise capital because you believe the money can be converted into much greater value. Every serious entrepreneurial act contains a claim about the future.

If a founder no longer believes that things can get better, it will soon become visible in the company. Preparation declines. Standards fall. Difficult conversations are postponed. The founder begins to preserve what remains instead of creating what comes next. Even if the resignation has not been submitted formally, the founder may have already resigned internally.

Optimism keeps founders moving. But not every statement of confidence deserves to be called optimism. Sometimes it is flattery. Sometimes it is fundraising theatre. Sometimes it is fear wearing an impressive presentation. Credible optimism must leave evidence.

Optimism is not a prediction that everything will be easy

Founders do not need to believe that every event will favour them. That would be fantasy. Markets change, products fail, employees leave, regulations shift, deals collapse and companies occasionally encounter problems they could not reasonably have predicted.

Optimism is the belief that a constructive response remains possible. Martin Seligman’s work on learned optimism focuses partly on how people explain setbacks to themselves. A pessimistic explanation tends to make a problem feel permanent, universal and personal: this will always happen, it will damage everything, and it proves that I am incapable. An optimistic explanation treats the setback as more limited and changeable: this happened under particular conditions, it affects a defined area, and there may be actions I can take.

That difference is enormously important in entrepreneurship. When a customer says no, the pessimistic founder hears that the market does not want the product. The useful optimist asks whether the wrong customer was approached, whether the value proposition was unclear, whether the price was wrong or whether the product needs to improve. When an investor declines, the founder does not automatically conclude that the business is worthless. They examine the investor’s thesis, the company’s evidence, the timing of the round and the quality of the pitch.

Optimism does not deny the rejection. It refuses to give one rejection authority over the entire future.

The founder lends belief to the company

In the early years, a company has little institutional confidence of its own. The brand is not yet established; the revenue may be inconsistent. The product is incomplete. The team has not accumulated decades of shared achievement. The founder’s conviction becomes one of the assets from which everyone else temporarily borrows.

Employees borrow it when a project takes longer than expected. Customers borrow it when they decide to trust a young company. Investors borrow it when they imagine that today’s small operation can become tomorrow’s important institution. Partners borrow it when they attach their reputations to an organisation whose future is still uncertain.

This is why optimism is contagious. People often take emotional cues from the person carrying the clearest responsibility for the outcome. If the founder communicates that every setback is a disaster, the team becomes afraid to take initiative. If the founder pretends there are no problems, the team stops trusting leadership. But if the founder can say, “This is serious, this is what we know, and this is what we are going to do next,” anxiety can be converted into action.

The founder does not have to perform excitement. Authentic optimism can be calm. It can acknowledge that the situation is difficult while insisting that the team is capable of thinking, learning and acting. Hope becomes leadership when it gives people something intelligent to do.

Delusion has no mechanism

What separates credible optimism from delusion? The mechanism.

A founder says the company will grow ten times. That is a prediction. The mechanism is the combination of product improvements, distribution, sales capacity, pricing, customer retention, capital and execution that could make the prediction true.

A founder says a fundraising round will close. The mechanism includes the milestones already achieved, the investors whose theses fit the company, the strength of the data room, the quality of the narrative, the amount being raised, the proposed valuation and the process for creating enough investor interest.

A founder says a new product will work. The mechanism includes the customer problem, evidence of demand, the superiority of the proposed solution, the team’s ability to build it and the channel through which customers will discover and adopt it.

This is what I mean when I say you should be able to see the algorithm. It is not necessarily a computer algorithm. It is the set of connected actions and assumptions expected to produce the outcome.

The optimistic founder should be able to explain:

• what they believe will happen;
• why they believe it;
• which assumptions must be true;
• what the team is doing to test those assumptions;
• which early results would indicate progress;
• what could make the theory wrong; and
• what the company will do if the original approach fails.

Delusion usually jumps from desire to outcome. Disciplined optimism builds a bridge between them.

Optimism should change the quality of the work

I do not judge optimism mainly by how confidently a founder speaks. I look at what their belief causes them to do.

If you genuinely believe a product can become important, the belief should appear in the care with which you build it. You will listen to customers, recruit capable people, test the experience and correct failures. You will not keep offering poor work to the market while using vision as an excuse.

If you believe you can multiply shareholders’ capital, that belief should appear in how you allocate money. You will understand the unit economics, protect cash, look for leakage and measure whether expenditure is producing value. You will communicate difficult facts instead of hiding them.

If you believe you can close an important customer, optimism should make you prepare more thoroughly. You will understand the customer’s problem, identify the decision-makers, anticipate objections and build an argument that is better than the available alternatives.

Optimism is reflected in the calibre of people you hire. A founder preparing for a meaningful future does not assemble a team that can only manage the present. The founder looks for people whose judgment, energy and experience can carry the company into its next stage. Your work is the receipt for what you claim to believe.

Optimism creates effort, but evidence must correct it

Psychological research generally associates optimism with persistence, adaptive coping and continued effort. That makes intuitive sense: people are more likely to invest energy when they believe their actions can improve the outcome.

However, research on entrepreneurs also supplies an important warning. Optimism is not automatically associated with superior company performance. In some studies, excessive optimism has been linked to poor results because founders underestimate competition, exaggerate demand or continue investing in a weak idea. Tali Sharot’s work on optimism bias similarly shows that expecting positive outcomes can be beneficial, but it can also cause people to discount unwelcome information.

The correct lesson is not that founders should become pessimists. A person who sees no possibility is unlikely to attempt something difficult. The lesson is that optimism must be updateable.

I think of this as a simple loop:

1. Believe: Form a strong view of what could become possible.
2. Build: Translate that belief into a product, team, process or experiment.
3. Measure: Decide what evidence should appear if the belief is correct.
4. Learn: Study what actually happened without manipulating the interpretation.
5. Adjust: Improve the method, revise the timetable or abandon an assumption.
6. Continue: Carry the learning into the next serious attempt.

Optimism supplies energy to the loop. Evidence supplies direction. Without optimism, the company may stop moving. Without evidence, it may move confidently in the wrong direction.

Your numbers should be allowed to disagree with you

A founder can persuade themselves of almost anything if the numbers are not permitted to speak.

Revenue is “about to grow.” The pipeline is “very strong.” Customers “love the product.” A major partnership is “almost complete.” These expressions can continue for months because they are difficult to falsify.

Operational optimism requires definitions. How many qualified opportunities are in the pipeline? What percentage moves from one stage to the next? How long does conversion take? How often are active customers using the product? What percentage renews? What is gross margin after the true cost of delivery? How much cash is available, and how long will it last under conservative assumptions?

The numbers do not contain the whole truth. A new opportunity may not yet be visible in historical performance, and a founder sometimes has to act before sufficient data exists. Nevertheless, numbers are valuable because they resist flattering narratives.

Your metrics should be able to prove you wrong. That is not pessimism. It is intellectual honesty, and intellectual honesty makes optimism more credible. Investors, employees and partners are more likely to trust a founder who understands the weaknesses in the business and can explain what is being done about them.

Fundraising requires an argument, not excitement

Optimism is especially visible during fundraising. The founder is asking an investor to purchase part of a future that does not yet exist.

Confidence matters. If the founder does not appear to believe in the opportunity, it is difficult to expect the investor to believe. But excitement alone is not an investment case.

The argument must make sense. Why does this problem matter? Why now? How many people or businesses experience it? Why is the company’s approach better than the alternatives? What evidence shows that customers care? Why is this team unusually capable of executing? What will the capital unlock? Which milestones should become possible before the next round?

The founder’s optimism should drive the preparation required to answer those questions. Investors do not invest simply because your argument is enthusiastic. They invest when the possible reward, the evidence, the team and the terms create a sufficiently compelling decision relative to other places they could deploy capital.

Even then, nothing is definite. Investors have different mandates, portfolios, time horizons and appetites for geography or risk. A strong business can receive several rejections. Therefore, the founder must remain optimistic enough to continue while learning enough to improve the case.

The best fundraising optimism sounds less like “You will regret missing this” and more like “Here is the future we see, here is why it matters, and here is the evidence that we are already moving towards it.”

A founder must tell the truth without spreading helplessness

Some founders fear that honesty will weaken the team. They think optimism requires them to conceal cash pressure, minimise a product failure or speak positively about an employee they know is not performing.

That is not optimism; it is the destruction of trust. People can usually sense when leadership is withholding reality. In the absence of honest information, rumours become the company’s operating system. The team imagines circumstances worse than the truth or, just as dangerously, continues working under assumptions that are no longer valid.

A founder can communicate difficult news optimistically by separating facts, interpretation and action:

• The fact: What has happened?
• The meaning: What does it affect, and what does it not affect?
• The action: What are we doing now?
• The responsibility: Who owns each next step?
• The review: When will we assess progress again?

For example: “We lost this customer, and it reduces monthly revenue by this amount. The cause was partly a gap in this part of our product and partly a change in the customer’s strategy. We are fixing the gap, speaking with these replacement prospects and reducing this expenditure. We will review the position in two weeks.”

That is more hopeful than vague reassurance because it gives the team agency.

Hire people who can strengthen your optimism

The founder may be the company’s most persistent optimist, but the founder should not be its only source of possibility.

Hire people who can look at a difficult target and begin thinking about how it might be achieved. Hire people who bring options, not only objections. Hire people who can challenge an assumption without becoming emotionally committed to failure.

At the same time, do not build a leadership team of professional encouragers who tell you whatever preserves your mood. You need colleagues who can say, “I believe we can win, but the current plan will not get us there.”

That sentence contains both loyalty and intelligence. An effective team creates productive tension around the founder. The founder stretches the organisation beyond what appears immediately comfortable. Capable leaders interrogate the assumptions, improve the plan and expose risks. Together, they turn optimism into execution.

The goal is not to make every employee think exactly like the founder. The goal is to create a culture in which difficult goals are taken seriously and difficult facts can be spoken freely.

Optimism can be practised

Some people appear naturally more optimistic than others, but useful optimism is also a discipline.

First, remember previous problems you have solved; this is not nostalgia. It is evidence that circumstances can change through intelligent action.

Second, reduce a frightening outcome into solvable components. “The company may fail” is emotionally overwhelming. “We need to close a monthly cash gap of this amount within ninety days” is a problem that can be examined.

Third, replace helpless questions with agency questions. Instead of asking only, “Why is this happening to us?” ask, “What remains within our control?”

Fourth, spend time with builders. Pessimism also spreads socially. If every conversation ends with an explanation of why nothing can work in Nigeria or Africa, possibility gradually begins to feel naïve. Serious builders do not ignore structural constraints, but they search for designs that can work within or around them.

Fifth, create small proofs. A first paying customer, a successful pilot, a working prototype or one outstanding hire can provide more durable confidence than a month of motivational speeches.

Finally, stay close to the reason you began. Optimism becomes easier to sustain when the problem still matters and the work remains connected to a purpose larger than the founder’s ego.

Believe enough to do the work

Optimism is an advantage because companies are built through actions whose rewards arrive later. You invest before the revenue appears. You recruit before the organisation reaches its full potential. You improve the product before every customer understands why it matters. You continue after a rejection because you believe the next attempt can be better informed than the last one.

But optimism must never become permission to lie—to investors, employees, customers or yourself.

The founder should be able to point to the mechanism. Show the hypothesis. Show the preparation. Show the people you recruited, the value you improved, the opportunities you pursued and the lessons incorporated after failure. Show how today’s work could produce tomorrow’s result.

You do not need certainty; founders rarely receive it. You need a belief strong enough to make you act and a mind honest enough to let reality improve that belief.

Optimism is not the absence of evidence. Optimism must leave evidence. —

References and further reading

• Martin E. P. Seligman, Learned Optimism: How to Change Your Mind and Your Life.
• Tali Sharot, The Optimism Bias: A Tour of the Irrationally Positive Brain.
• Tali Sharot, The Optimism Bias, TED.
• Peter Schulman, “Applying Learned Optimism to Increase Sales Productivity,” Journal of Personal Selling & Sales Management.
• Keith M. Hmieleski and Robert A. Baron, “Entrepreneurs’ Optimism and New Venture Performance,” Academy of Management Journal.
• Jim Collins, Good to Great.
• Ben Horowitz, The Hard Thing About Hard Things.