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

Most angels overthink this.

They spend weeks analyzing market size. They build financial models. They request 17 follow-up meetings. Then they miss the good deals because while they were analyzing, someone else wrote the check.

At Hustle Fund, we see thousands of deals per year. I've invested in over 800 companies personally. You know how long it takes me to know if something is interesting? About 10 minutes.

That's not because I'm smarter than other investors. It's because I know what actually matters at the early stage. And I've learned to ignore everything else.

The Only Three Questions That Matter

Can this team build the product? This is about technical ability and execution speed. Have they built things before? Do they have the skills needed for this specific product? Can they move fast?

You can usually tell from their story. If they've shipped products before, they'll tell you about them. If they're first-time founders with no technical co-founder trying to build complex software, that's a red flag.

Look for builders, not talkers. The founders who've already built a prototype are more credible than founders with beautiful pitch decks and no product.

Can they sell this product? Customer acquisition kills more startups than anything else. The best product in the world doesn't matter if nobody buys it.

Ask: "How will you get your first 100 customers?" If they say "we're going to try a few different things," that's a bad answer. If they say "I'm going to email everyone I know from my last job because they all complained about this exact problem," that's a good answer.

At pre-seed and seed, we don't even care if they have revenue yet. We care if they have a clear, repeatable plan for how they'll get it.

Will this be a big business? Market size matters but probably not how you think. I'm not looking at TAM slides claiming the market is $100 billion. I'm asking: "If this works perfectly, how big could this company realistically become?"

A $50 million outcome doesn't return a VC fund, but it's a fantastic outcome for angels. So I'm less concerned about market size than most investors. What I care about is whether there's a path to meaningful scale.

Can this go from $1 million in revenue to $10 million? From $10 million to $50 million? If the business model makes that impossible (like brick-and-mortar retail), it's probably not VC-backable.

The 30-Minute Evaluation Framework

First 10 minutes: Let the founder pitch. Don't interrupt. Just listen to their story. How clearly do they explain the problem? Do they have personal connection to it? Does the solution make intuitive sense?

Most pitches fall apart here because founders can't explain their business simply. If I don't understand what you're building in two sentences, your customers won't either.

Next 10 minutes: Ask questions. I have a standard set:

• How did you come up with this idea?
• Who's the customer and why do they care?
• How will you reach them?
• What have you built so far?
• What's your revenue model?
• Who else is working on this problem?
• Why will you win?

The answers to these questions tell me everything. Good founders have crisp answers. They've thought about these questions deeply because they live with them every day.

Bad founders are vague. They pivot to talking about TAM when you ask about customer acquisition. They name competitors they clearly haven't researched. They can't articulate why they're uniquely positioned to win.

Final 10 minutes: Dig into concerns. Every deal has at least one thing that worries me. Maybe the market seems crowded. Maybe the founding team is unbalanced. Maybe the business model requires huge upfront capital.

I tell them exactly what concerns me and see how they respond. Good founders address the concern directly. They've already thought about it and have a plan. Bad founders get defensive or dismissive.

This part also tests for coachability. If they can't take critical feedback in a pitch meeting, they definitely can't take it when things go wrong.

What Busy Professionals Get Wrong

The biggest mistake busy professionals make is thinking they need deep industry expertise to invest. You don't.

Some of my best investments have been in industries I knew nothing about. Domain expertise helps with sourcing deals and helping portfolio companies. But it's not required for making good investment decisions at the early stage.

The second mistake is analysis paralysis. You'll never have perfect information. At pre-seed and seed, you're betting on trajectory, not current state. By the time you have enough data to be confident, the valuation will be 3x higher and someone else will have led the round.

I've watched so many smart people pass on great companies because they wanted one more meeting. Meanwhile, three other angels wrote checks after a single conversation. Speed matters.

The Red Flags That Show Up Immediately

Some things disqualify a deal in the first five minutes.

If the founder isn't working on this full-time, I'm out. Part-time founders signal lack of commitment. Starting a company is hard enough when you're all-in. Part-time? It's not going to work.

If they can't articulate their business model clearly, I'm out. "We'll figure out monetization later" is fine for consumer social apps with millions of users. It's death for B2B SaaS.

If they've been working on this for two years with nothing to show, I'm out. Great founders ship fast. If they've been "building in stealth" for years, they're either perfectionists or can't make decisions. Both are fatal.

If they badmouth previous investors or co-founders, I'm out. Sometimes people have legitimate grievances. But if everyone they've worked with was terrible, that tells me who the actual problem is.

If their valuation is crazy relative to progress, I'm out. I don't care if they raised at a $50 million cap from some other investor. If they have no revenue and no product, I'm not paying that price.

How to Use Pattern Recognition

After you've seen 50 deals, you start recognizing patterns. Certain types of founders succeed more often. Certain business models work better at early stages. Certain pitches that sound good always fail.

For example, I've learned that founders with previous startup experience perform better, even if their last company failed. They've seen the movie before. They know what's coming.

I've learned that marketplace businesses are incredibly hard at the early stage. Two-sided networks require massive user acquisition on both sides simultaneously. Most fail.

I've learned that "we're 10x better than the existing solution" is usually BS. Customers don't switch just because something is better. They switch when the pain of their current solution becomes unbearable.

These patterns help me make faster decisions. When I see a marketplace pitch from first-time founders at a $20 million valuation, I know within 30 seconds this isn't for me.

Why Your Instinct Is Usually Right

There's academic research showing that first impressions are remarkably accurate. The gut feeling you get in the first 10 minutes of meeting someone is usually right.

This doesn't mean ignore data. It means trust your instincts about people. If something feels off about the founder, it probably is. If they seem brilliant and driven, they probably are.

I've talked myself into deals against my better judgment. Every single time, my initial instinct was correct. The founder I thought seemed scattered was scattered. The market I thought seemed too competitive was too competitive.

Now I trust my gut more. If I'm not excited after 30 minutes, I pass. Life's too short to invest in companies you're not excited about.

The Follow-Up Process for Busy People

If you like a deal after 30 minutes, what's next?

For me, it's customer calls. I need to talk to two or three people who are using the product or who would be customers. This takes maybe an hour total and tells me if the founder's story is real.

Then I check cap table and terms. This is a 10-minute exercise. Who else invested? At what valuation? Are there any weird terms? If everything looks clean, I'm ready to commit.

Total time investment: maybe two hours from first pitch to writing the check. Compare that to VCs who take eight meetings over six weeks. As an angel, your superpower is speed.

Why Fast Decisions Actually Work Better

Making faster decisions often leads to better outcomes.

When you overthink, you talk yourself into or out of deals for the wrong reasons. You start optimizing for things that don't matter at the early stage. You miss obvious red flags because you're focused on market analysis.

Fast decisions force you to focus on what matters: the team and their ability to execute. Those are the only things that predict success at the pre-seed stage anyway.

Plus, founders appreciate investors who move quickly. When you can say "I'm in" after one conversation, they remember that. They'll come back to you for their next round. They'll refer other founders to you.

The best angels aren't the ones who spend months analyzing. They're the ones who've seen enough deals to recognize quality quickly and have the confidence to act on it.

Learning to make fast decisions gets easier when you're comparing notes with other investors. Angel Squad members share how they evaluate deals, what questions they ask, and which signals they've learned to trust. Because investing while working full-time isn't about having more hours in the day. It's about having better pattern recognition from seeing what actually works. And that comes from learning from people who've already evaluated thousands of deals.