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

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

Why is this so crucial?

Well... building a startup is like navigating that crazy maze in Harry Potter. The one where the walls keep moving. Just when you think you've figured out the path, the walls shift, and you're facing a whole new set of challenges.

In this environment, treating every experience – good or bad – as a learning opportunity isn't just nice to have. It's essential for survival. But how do you evaluate something as intangible as a "learning mindset"? Hustle Fund investor Shiyan Koh has some thoughts on the topic. Let's dive in to her strategies.

What we're looking for

It's no secret that Hustle Fund's investment team doesn't look at pedigree when evaluating an early-stage investment opportunity. And while we do look at things like market pull and team, we also place a super high value on the learning mindset.

So when a founder tells us about her outstanding accomplishments, here's what we're really looking for:

1. The ability to extract meaningful lessons from past experiences – triumphs and face-plants.
2. How those learnings are being applied to the current startup.
3. The founder's "learning model" – aka, how they approach new information and challenges.
4. Openness to new ideas. (Are they excited by fresh perspectives, or do they cling to their existing worldview?)

Putting it into practice

Here are a few examples of how we use this process:

1. Organizational learning: How do they apply lessons from their previous work environments? Did they absorb the best practices from BigTech Company X, or are they trying to recreate that exact culture in their 5-person startup?
2. Talent assessment: What insights have they gained about building and managing teams? Have they learned from past hiring mistakes, or are they still chasing the "perfect" resume?
3. Regulatory understanding: How well do they navigate constraints – and opportunities – in their industry? Are they proactively learning about potential roadblocks, or are they crossing their fingers and hoping for the best?
4. Technical vs. non-technical balance: For technical founders, have they learned anything about distribution and go-to-market strategies? For non-technical founders, how have they improved their ability to work with engineering teams?
5. Industry-specific transitions: If a founder is moving from, say, e-commerce to B2B software, how are they adapting their approach? Do they recognize that selling to enterprises is a whole different ballgame compared to consumer marketing?

Questions to ask

"Great, but how do I actually uncover this stuff in an interview?" - you, probably

Here are some questions that can help you dig deeper into a founder's learning mindset:

1. "Tell me about a significant challenge from a past role. How did that experience shape your approach to your current startup?"
3. "How has your understanding of talent acquisition and management evolved throughout your career?"
5. "What have you learned about working with [technical/non-technical] teams that you're applying to your new company?"
7. "You're moving from [previous industry] to [current market]. What elements do you think will transfer over? What do you need to learn to be successful?"

Honestly? These questions are just starting points. The real gold lies in the follow-up questions and the depth of the conversation that follows.

Reading between the lines

Alright, you've asked the questions. Now comes the fun part: decoding the responses. Here's what we're listening for:

1. Depth of reflection: Are they giving surface-level answers, or have they really processed their experiences?
2. Practical application: Can they give concrete examples of how they're applying their learnings?
3. Openness to change: Do they show a willingness to adapt based on new information, or are they set in their ways?
4. Cross-domain thinking: Can they take insights from one context and apply them creatively to another?
5. Continuous learning mindset: Is there evidence that they're actively seeking out new knowledge and skills?

It's not just about what they say, but how they say it. Are they excited when talking about new learnings? Do their eyes light up when discussing a challenge they overcame?

Pay attention – these cues can tell you a lot about a founder's true relationship with growth.

This mindset matters more than ever

Millions of startups are launching every year. Competition for investor dollars, for market share, and for top talent is steep. The founders who can learn, unlearn, and relearn quickly are the ones who will not just survive, but thrive.

They're the ones who can pivot when necessary, who can spot opportunities others miss, and who can build resilient teams capable of weathering any storm. Now all you have to do is spot them 🔭.