Hope is a strategy. Optimism is not.

An entrepreneur is both arrogant and vulnerable. They are optimistic, hopeful and project fierce confidence in the face of terrible success probabilities. And they are not simply young people throwing caution to the wind. The average age of Founders in the US ranges from the late 30s to the early 40s so the professional and personal financial risk is real as is the opportunity cost. A Founder must believe that what they are about to build or are building will work and solve real problems for customers. But when they encounter operational delays, funding pressures, resource exhaustion, and the fanfare from their friends and family have died down, then how do they evolve? How do they sustain their mindsets for the long haul when the destination may be clear (financial exit) but the timeline is unknown? In those early months and years optimism and hopeful mindsets are their currency. But optimism alone does not survive contact with reality. What is sustainable for Founders is hope: as defined by psychologist C.R. Snyder as agency ("will power") and pathways ("way power") working in tandem. Small, visible progress, focused on controllables, can catalyze future outcomes.

OPTIMISM

James Stockdale, a senior commanding Naval officer, was shot down over North Vietnam in September 1965. He spent over seven years at the "Hanoi Hilton," and he was the senior officer among the other prisoners. Even in confinement and being repeatedly tortured, Stockdale led the other prisoners to endure extreme hardship.

In Jim Collins's 'Good to Great' Stockdale talked about which prisoners didn't make it out of the camp. "Oh, that's easy, the optimists." The rest of the discussion centered on prisoners who thought for sure they'd be released by Christmas. And when that date passed, they'd say Easter, and then Thanksgiving, etc. until the repeated disappointment broke their spirit. Collins called this the "Stockdale Paradox." Optimism tied to specific dates and outcomes was problematic in his observations.

"You must never confuse faith that you will prevail in the end - which you can never to afford to lose - with the discipline to confront the most brutal facts of your current reality, whatever they might be." - Admiral James Stockdale

As a Founder myself, my darkest moments have been when I was nowhere near the progress goals I had set versus timelines. My vision board in 2015 certainly did not have me running three small venture funds after more than a decade of hard work, persistence, and adaptation. But I'm still operational, adapting as quickly as possible.

I think what draws so many professionals to the world of startups and technology is the unbridled enthusiasm and optimism Founders display in those early years. When the known failure rates are immense and most people tell them it won't work…. they adapt and overcome. Everything seems possible all at once. And there's a certain freedom in going it alone, betting on oneself, and taking full control of your daily priorities. I've learned that this optimism starts to evolve when Founders approach their first, significant pre-Series A financing. They've been working full time in the business at 100+ hrs/week, marshaled every resource and network connection possible, and worked through at least their first iteration of the product. For most, they realize their thesis and initial timeline projections were flawed and must adapt. Many then must take additional dilutive (venture) capital to bridge their companies or reduce salaries or fire the handful of teammates they could afford. These are critical moments, so I try to extend empathy when companies are adapting to survive; keeping the shot clock from running out while searching for the breakout opportunity. I think this is the essence of the Stockdale Paradox; Founders must face "the brutal facts of their current reality." They must unlock the components of hope they launched the company with: will power and way power.

POWER OF HOPE

Snyder et al (1991) defined Hope as the combination of Agency (the belief that you can start and sustain movement towards a goal, aka 'will power') and Pathways (the perceived ability to generate workable routes to the goal, aka 'way power'). In 2002 Snyder discussed how "high-hope" people encounter blocked paths and immediately look for alternative routes, while "low-hope" people view blocked paths as an end state.

I often see Founders adapting and surviving solely without a go-forward plan or intentionality. They are just existing. I've been guilty of this in moments in my own entrepreneurial journey. This is where purpose is important to me-the WHAT and the WHY of the company when it was launched. The HOW can and should change often as obstacles are encountered, but is the company drifting from its purpose? A company adapting is brutally honest with the current state and is continuously seeking advice and counsel on next steps to take. But a company that is drifting is not open to external ideas or feedback, refuses to face financial reality, and is paralyzed with fear.

Hmieleski & Baron (2009) found that Founders who expect positive outcomes "even when such expectations are not rationally justified" had worse startup outcomes. Hope, in Snyder's framework, is tied to specific goals, and the individual must have two beliefs: ability to move towards a goal (agency) and that you can find routes to get there (pathways). For me, hope is more goal oriented. As a Founder, I've generally had the faith that I will prevail - that I have agency over my actions, standards, and effort. The greater challenge for me has been the pathway. So much of a venture firm's activities are tied to its capital resources, so finding a pathway to scale has been my greatest obstacle. Power and influence in venture tend to follow fund size, and fund size doesn't always track with performance, added value to Founders, or even trustworthiness.

CONTROL WHAT YOU CAN CONTROL

"…managers and their stakeholders tend to develop illusions that the world is more controllable and predictable than it actually is, and these illusions can entail costly errors in modern society." (Liu & de Rond, 2016)

I believe that probably half (or more) of the outcomes for venture-backed startups are randomized or attributable to luck. Many Founders and their VC firm backers will vigorously disagree, but the data and influence of Power Law are hard to ignore. The vast majority venture funds from 2017 to present are unprofitable right now (<1.0 DPI). Research also reveals that in these "noisy" outcome environments Founders should focus on decisions and effort; not allowing any single outcome to define them. This is easier said than done, especially with major pressure from investors and customers.

Dealing with Investors
The support Founders receive from their investors varies widely, and in my experience, it depends more on the individual Partner than on the VC firm. Nearly every firm talks about its playbooks, networks, and domain expertise. What I've found is that only a small percentage of these investment partners show up with the judgment and leadership that matter in a Founder's critical moments. I try to hold our own firm to a higher standard.

I've also witnessed tremendously skilled and competent Founders struggle to raise small, straightforward rounds of capital. Raising capital is often an illogical process and holistically time dilutive to a Founder's number one priority: leading the company's execution. But they must do it. This comes with powering through erratic due diligence processes, habitual lack of follow-through by individuals at investment firms, and exploring the gaps between what a venture firm says they look for and how they operate in reality. Founders must remain optimistic with each iteration with potential investors as they need the capital. The power dynamic here is in the hands of the investor.

Building a Repeatable Customer Base
Our companies are primarily selling to enterprises where sales cycles have averaged 180-270 days or longer for $100k+/year engagements. Founder-led sales are common, and on top of everything else they must present a confident and optimistic view of what their solution can achieve for a customer. The customer generally will not have the budget for their product or platform so Founders must try to land a pilot or trial, relentlessly overdeliver, and pursue follow-ups until a contract is in the discussion. And then comes price negotiations, legal reviews, procurement hoops, etc. Repeat.

Some of our companies sell to US and Allied militaries which have even longer sales cycles, burdensome procurement requirements, and opaque budget requirements. As with enterprises Founders must inform and educate stakeholders as to how their solution is needed. A trend that I find disappointing is that small startups are now having to fund lobbying firms and spend Founder time meeting US Congressional leaders, like the large companies do, to garner budget favor for the next fiscal budgeting cycle. Founders must smile, display their domain expertise, and resist growing frustrations. Many times, the key leader acknowledges the need, expresses a desire to move quickly, but lacks the budget or budget authority to do anything about it.

Dealing with investors and building a customer base are two major focal areas for Founders. Both lanes are highly inefficient, at times illogical, and most outside of the Founder's control. But how they embrace these tasks, govern their attitudes and manage their effort, are areas within their control. And they must sustain these over years, not just the "fun" early months of a startup. Founders must project optimism with both stakeholder groups and run on grounded hope internally.

CONCLUSION

The research on hope suggests that what sustains leaders and teams is not blanket optimism that deals will close, the product will work, the startup will scale rapidly, customers will love it, etc. It is grounded hope: confronting the facts honestly (the Stockdale Paradox), building multiple pathways forward (Snyder), and focusing on what can be controlled. For me it is telling how a Founder evolves after the first 12-month "glory period" of the startup to those middle years of pain, complexity, and sustained hyper vigilance. Whereas hope and optimism were easy at the outset of their journey, Founders must manage their emotions, expectations, and energy over the long haul to sustain high-quality decisions. Small, visible progress is what keeps will power and way power sustainable over years. Hope, in this sense, isn't wishful thinking. It's discipline: a goal, the will to attack it, and the willingness to be brutally honest with adaptations. That's a strategy.

SOURCES

Snyder, C. R., et al. (1991). The will and the ways: Development and validation of an individual-differences measure of hope. Journal of Personality and Social Psychology, 60(4), 570-585. https://doi.org/10.1037/0022-3514.60.4.570
Snyder, C. R. (2002). Hope theory: Rainbows in the mind. Psychological Inquiry, 13(4), 249-275. https://doi.org/10.1207/S15327965PLI1304_01
Collins, J. (2001). Good to great. HarperBusiness, Chapter 4, "Confront the Brutal Facts."
Stockdale background: U.S. Navy, "Return with Honor".
Hmieleski, K. M., & Baron, R. A. (2009). Entrepreneurs' optimism and new venture performance: A social cognitive perspective. Academy of Management Journal, 52(3), 473-488. https://doi.org/10.5465/amj.2009.41330755
Liu, C., & de Rond, M. (2016). Good night, and good luck: Perspectives on luck in management scholarship. Academy of Management Annals, 10(1), 409-451. https://doi.org/10.5465/19416520.2016.1120971
Walker, P., & Dowd, K. (2026, June 4). VC fund performance: Q1 2026. Carta. https://carta.com/data/vc-fund-performance-q1-2026/.