As an investor, you probably rely on pattern recognition more than you realize.
You’ve seen countless pitches. You know what good deals tend to look like, which markets are gaining momentum, and what business models have worked before.
That experience is valuable. But there’s a potential downside: the patterns that help you make decisions quickly can also make it harder to recognize something genuinely new.
That’s the tension Holly Uber explored in her Summer Expo 2026 keynote, The Curiosity Edge. Her argument is that curiosity can give investors an advantage because it helps them notice when their “map” is incomplete—and gives them the courage to redraw it.
When Familiarity Becomes the Filter
Think about the last company you evaluated. Did you find yourself thinking, “This reminds me of…”?
There’s nothing inherently wrong with that. Pattern recognition is one of the advantages experience gives an investor. The problem starts when familiarity becomes the filter.
If one company doesn't look like the companies you've seen succeed before, it can be tempting to dismiss it. Maybe the market seems too early. Maybe the business model doesn't fit your thesis. Maybe the entrepreneur doesn't have the background you typically associate with the category.
But what if the unfamiliarity is exactly what deserves another look?
Holly describes this as having an incomplete “map.” If you're only looking through the map you already have, you may miss what's outside it.
So if you're looking for the next exceptional company, ask yourself: Does it really have to look like the companies that came before it?
Ask Yourself: “What Am I Missing?”
This is where curiosity becomes an investment discipline.
Instead of asking only, “Does this fit the pattern?”, try asking: “What am I missing?”
That question can change the conversation.
You might discover why an entrepreneur chose an unconventional approach. You might find that a market you considered too small has an unexpected entry point. Or you might uncover customer behavior that challenges your initial assumptions.
You aren't abandoning your investment thesis. You're testing it.
Holly describes curiosity as the discipline of asking questions and noticing when your map is incomplete. But the harder part, she says, is having the courage to expand that map.
And real curiosity begins when the answers don't confirm what you already believe.
Look Beyond the Company Today
There’s another reason to look beyond familiar patterns: companies change.
Markets change. Technology changes. Customers change. Sometimes, the business itself changes.
That’s why Holly says she pays particular attention to capability when evaluating deals, alongside feasibility, desirability, and viability. She wants to know whether the business can adapt to change and turn it into an advantage.
That gives you another lens for diligence. Instead of asking only, “Does this company work today?”, ask: Can this team recognize when something needs to change? Are they willing to challenge their own assumptions? Can they learn quickly and act on what they learn?
Those answers may tell you more about the company's long-term potential than a snapshot of today's business.
Ask the Founder What Surprised Them
Holly shared one question she likes to ask entrepreneurs:
“What’s one thing that surprised you when you talked to a customer? And how did it change your product?”
Try it in your next conversation with an entrepreneur. You're not just asking for a customer story. You're looking for evidence that the founder listens, learns, and adapts.
A leader who can tell you what surprised them—and what they changed because of it—is showing you something important: they don't treat their original assumptions as the law.
And that's valuable when you're investing in a future nobody can predict perfectly.
Pause. Ask another question. Look again.
A company might look ordinary from one angle. So the next time a deal looks ordinary to you, shift your perspective, and you might see a different customer problem, a new market, an unconventional business model, or a team capability you hadn't considered.
So the next time a startup doesn't immediately fit your pattern, don't automatically move on.
*This blog is inspired by Holly Uber’s keynote “The Curiosity Edge” at the Summer Investor Capital Expo 2026.