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

Perhaps the best way to get good at investing is to listen in on an experienced investor's pitch meetings with founders. Not read about it. Actually watch it happen.

When Angel Squad hosted a Shark Tank-style session where a founder pitched Elizabeth Yin live in front of the community, it was one of those rare moments where you could see exactly how an experienced investor thinks in real time. What questions she asked, why they mattered, and what she was really listening for beneath the surface.

Here is what we learned.

The Partnership Risk Question

One of the first things Elizabeth dug into was the company's key business relationships. In this case, the startup (Colorfull, a corporate food delivery company) had built its model around a partnership with a major ghost kitchen brand.

Elizabeth's question: What happens if that partner decides to go after this market themselves?

This question is brilliant because it does three things at once. It tests whether the founder has thought about the biggest existential risk to the business. It reveals how dependent the company is on a single partner. And it shows you how the founder thinks about de-risking.

The founder, Garrett Serviss, explained that while the ghost kitchen partnership would dominate the first year, he was already in talks with other ghost kitchens to diversify. Even if his primary partner decided to compete (which he was confident they would not, given their prior failed attempt at the same thing), he was building relationships with alternatives.

That is what de-risking looks like in practice. Not just acknowledging the risk, but actively building contingency plans.

For any startup built on top of another platform or partner, ask this question. What happens if that partner changes terms, raises prices, or decides to compete? A founder who has not thought about this is sitting on a time bomb.

The Questions Behind the Questions

Elizabeth has a framework she uses across every pitch. From Hustle Fund's "Raise Millions" guide, here are the categories she cares about most and the specific questions within each.

On the team, she wants to know: why is your team uniquely motivated to solve this problem? When was the last time you disagreed on a business issue, and how did you resolve it? These questions reveal coachability, communication, and whether the co-founding relationship can survive stress.

On unit economics and customer acquisition, she digs deep: how are you currently getting customers? How much does it cost to acquire one? How have different channels performed? She wants to see that the founder can slice and dice their numbers across time and across channels. That level of specificity shows the founder actually understands what is driving the business.

On the problem: what is the specific problem you are solving, how big is it, and who has it? A founder who cannot clearly articulate the problem they solve is a founder who has not done enough customer discovery.

Elizabeth has noted that most VCs look at teams first. But her background as an entrepreneur is why she looks at ideas and unit economics above all else. If the economics work, many teams can execute. If they do not, even an incredible team will struggle.

The "Must De-Risk" Analysis

After every pitch, Elizabeth runs what she calls a "must de-risk" analysis. Each company has a specific set of things that are critical to get right. Those things are different for every business.

For a company building a design tool, the product and UX have to be exceptional. For a company building a CRM, the team has to dominate at sales. For the food delivery company she evaluated, the two critical things were unit economics and enterprise sales.

This is one of the most useful frameworks for any investor. Instead of trying to evaluate everything about a company equally, identify the one or two things that absolutely must work for the business to succeed. Then dig hard into those specific areas.

If the founder can show progress on their must-de-risk items, the deal gets much more interesting. If they cannot, it does not matter how good the rest of the pitch is.

The Question Most Investors Forget

At the end of the pitch, Elizabeth asked: "What can I answer for you?"

This surprises people. The power dynamic in pitch meetings feels clear. The investor holds the cards. The founder should feel lucky to have the meeting.

But giving the founder space to ask questions does two important things. It shows respect. And it often reveals how the founder thinks. Are they asking about your decision timeline? That is practical. Are they asking about your portfolio and how you support companies? That shows they are evaluating you too, which is a green flag.

Elizabeth also made a point of saying "we WILL get back to you" at the end. So many investors ghost founders after a pitch meeting. It is disrespectful and a waste of the founder's time. If you are going to pass, say so. The founder will remember how you treated them during a "no" far longer than the investors who said yes.

If you want to watch experienced investors evaluate deals in real time and develop your own pitch evaluation instincts, Angel Squad hosts live sessions exactly like this one. Join 2,500+ members sharpening their skills at Angel Squad.

The right questions do not just evaluate a company. They reveal everything about how the founder thinks.