Venture Fund Lessons on Evidence, Risk and Better Business Decisions

Better decisions come from a repeatable process

Launching a venture fund in Las Vegas gave Len Jessup a practical test of how leaders should act under uncertainty. His experience points to a useful discipline: gather enough evidence to make a reasoned move, keep early commitments manageable, then turn the outcome into a better decision process. The value lies less in feeling certain than in knowing what remains untested and who will be affected if an assumption proves wrong.

Jessup, managing partner at Desert Forge Ventures, traces the approach to an earlier lesson from a doctoral seminar. He once held back from speaking until he felt sure he was right, a habit that protected him from embarrassment but also limited his growth. He later set himself a different standard: take on enough challenge to risk being wrong, then learn from it. In entrepreneurship and venture investing, he formalized that idea as “Act, Adjust, Absorb.”

The framework has direct relevance for business decisions where information is incomplete and commitments have consequences. It asks leaders to distinguish the evidence they have from the certainty they may want, and to adapt as new information arrives.

Act when the evidence is sufficient

Starting before every detail is settled can be sensible; acting without evidence is a different matter. Jessup’s account of forming Desert Forge Ventures shows how he tried to reduce uncertainty before committing to the fund’s direction. He consulted people familiar with venture capital and the startup communities he hoped to serve, then used their input to refine the opportunity.

One early conversation was with his nephew, who is closely involved in Silicon Valley. That exchange helped Jessup frame the fund and prepare for the wave of artificial intelligence startups he expected to emerge. He also spoke with a friend in Tucson who had founded funds focused on the University of Arizona. The friend’s experience helped Jessup sharpen the fund’s positioning in Las Vegas and provided legal documents from an earlier fund as a working template.

The point of those conversations was not simply to collect encouragement. For consequential decisions, useful outside input should test the premise, expose what’s missing and clarify the conditions required for success. Questions such as “What am I missing?”, “What has to be true?” and “Where could this fail?” make it harder to mistake enthusiasm for evidence.

There’s a limit to analysis, too. More discussion can stop reducing risk and start delaying a decision that already has enough support to proceed. The judgment call is recognizing when the available signal is sufficient for the next step, even though certainty remains out of reach.

Keep early commitments small enough to adapt

The fund’s first investments showed how a sound thesis can still create pressure if the pace of commitments outruns the resources available. Jessup initially focused on deep technology emerging from university labs. The first two investments fit that focus, but both companies sought substantial lead investments. The fund was still raising the capital needed to support them, and Jessup agreed to proceed anyway.

That choice left the fund in a difficult position. Jessup responded by accelerating fundraising, recalibrating discussions with investors and communicating timelines more deliberately to both investors and the companies. The experience sharpened a distinction with broad business relevance: decisions that are easy to reverse can often be made early; decisions that create obligations for other people call for greater care.

For a leader weighing a commitment, the practical questions are specific. What assumption is this move testing? What is the smallest credible step? What conditions must hold for it to work? Who will depend on the organization after it says yes? And what evidence would prompt the team to speed up, change direction or stop?

These questions connect the size of a decision to its learning value and its exposure. A smaller move can test an assumption while preserving room to respond. A larger commitment may be justified, but it can bring other people’s plans and expectations into play. Jessup’s experience suggests that leaders should make those dependencies visible before they commit.

Absorb the lesson before the next decision

Acting and adjusting are only part of the process. Jessup argues that leaders often move on too quickly after a decision, leaving useful information behind. A regular review can help turn an isolated outcome into a better operating habit. He recommends making time each week to address one conversation, question or decision that has been avoided, then asking: What did I expect? What happened? What did I learn?

That review helps separate what a leader knew from what they believed and what still needed testing. It also makes it easier to identify whether the original assumptions held, whether the timing or commitment was poorly calibrated, or whether new information changed the picture. The aim is not to remove mistakes from entrepreneurial work; it is to make each experience more useful to the next decision.

Jessup says his experience with the fund changed how he defines readiness. He now considers not only whether he is prepared to move, but also whether the people and resources affected by the choice are prepared. He deliberately seeks out people who will challenge his thinking, giving disagreement a role in the decision process before commitments are made.

Use uncertainty to calibrate judgment

Push beyond the comfort zone is common entrepreneurial advice. Jessup’s framework adds a way to judge what happens after taking that step. Comparing feared outcomes with actual results builds evidence over time: asking a question that feels basic may reveal that others share the same confusion, while respectful disagreement may prove less costly than expected. That feedback can help leaders distinguish operational risks from anxieties that have not been tested.

Uncertainty, in this view, is not proof that a leader is unprepared. It marks the area where judgment is being formed. Confidence can follow from acting on sufficient evidence, adjusting when circumstances teach something new and absorbing the lesson before the next call. For business leaders, the concrete takeaway is to make the next move proportionate to the evidence, account for who will rely on it, and use the result to improve the decision that follows.