Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

In the world of early-stage startups, many investors look for impressive stats and past achievements. Things like "built a 2 million person community" or "helped launch Amazon's big product" or "raised $40M at my last company."

Those accomplishments are nice. But at Hustle Fund, we are seeing another quality that might be the secret ingredient to a winning startup: a learning-first mindset.

Building a startup is like navigating that crazy maze in Harry Potter. The one where the walls keep moving. Just when you think you have figured out the path, everything shifts and you are facing a completely new set of challenges. In that environment, treating every experience as a learning opportunity is not just nice to have. It is essential for survival.

Hustle Fund investor Shiyan Koh has spent a lot of time thinking about how to evaluate this quality. Here is what we look for.

What We Are Actually Looking For

When a founder tells us about their background and accomplishments, here is what we are really trying to understand beneath the surface.

Can they extract meaningful lessons from past experiences, both successes and failures? How are those lessons being applied to their current startup? What is their "learning model," meaning how do they approach new information and challenges? And are they genuinely open to new ideas, or do they cling to what they already believe?

That last one is a big deal. We have backed founders who had no relevant background in their industry but learned so fast that within a year they were the most knowledgeable person in the room. We have also passed on founders with incredible resumes who were so locked into their existing worldview that they could not adapt when the market shifted.

How to Actually Spot It

Saying "I want to invest in learners" is easy. Figuring out who actually has this quality in a 30-minute conversation is the hard part. Here are some angles that help.

Look at how they talk about past roles. Did they absorb the best practices from their previous company, or are they trying to recreate that exact culture in their 5-person startup? A founder who learned the right lessons from BigTech Company X is very different from a founder who is blindly copy-pasting a playbook that was designed for a 10,000-person organization.

Look at how their thinking about talent has evolved. Have they learned from past hiring mistakes? Can they articulate what they got wrong and how their approach has changed? Or are they still chasing the "perfect" resume without questioning whether that is the right filter?

Look at cross-domain transitions. If a founder is moving from e-commerce to B2B software, are they adapting their approach? Do they recognize that selling to enterprises is a completely different game from consumer marketing? A founder who thinks "sales is sales" has not learned the lesson yet.

And for technical founders specifically, have they developed any instinct for distribution and go-to-market? Elizabeth Yin has pointed out that most VCs look at teams first, but she looks at ideas and unit economics above all else, because if the customer acquisition works, many teams can execute. A technical founder who has learned to think about distribution, even imperfectly, is far more valuable than one who only cares about the engineering.

The Questions to Ask

Here are some questions that help uncover the learning mindset:

"Tell me about a significant challenge from a past role. How did that experience shape your approach to your current startup?" You are listening for depth of reflection, not a polished answer. Did they actually process the experience or are they giving you a rehearsed response?

"How has your understanding of hiring evolved throughout your career?" This one is revealing because almost everyone has made hiring mistakes. The question is whether they learned from them.

"You are moving from [previous industry] to [current market]. What elements transfer and what do you need to learn?" You want to hear honest self-assessment, not overconfidence about how everything they know applies perfectly.

The real gold is in the follow-up questions. Push deeper on anything that sounds surface-level. A founder with a genuine learning mindset will get more articulate and engaged the deeper you go. A founder faking it will start to run out of substance.

Reading Between the Lines

Pay attention to more than just the content of the answers. Are they excited when discussing challenges they overcame? Do they light up when talking about something they figured out? Those cues tell you a lot about someone's relationship with growth.

Watch for founders who can take insights from one context and apply them creatively to another. Cross-domain thinking is one of the strongest signals of a learning mindset. The founder who says "I noticed this pattern in healthcare and realized it applies to our logistics problem" is showing you exactly the kind of adaptability that matters in early-stage companies.

Millions of startups launch every year. The founders who can learn, unlearn, and relearn quickly are the ones who survive. They are the ones who can pivot when necessary, spot opportunities others miss, and build teams capable of weathering real adversity. At Angel Squad, members develop the founder evaluation skills to spot these qualities, drawing on Hustle Fund's experience across 600+ investments. Explore it at Angel Squad.

Now all you have to do is spot them.