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 angel investors are terrible storytellers.

They lead with numbers that don't mean anything. They bury the interesting parts under jargon. They forget that investing is fundamentally a human activity driven by conviction, pattern recognition, and narrative.

At Hustle Fund, we've reviewed over 30,000 pitches. We've also watched angel investors try to tell their own stories about why they're good at this. The gap between effective storytelling and what most people actually do is massive.

Here's what works.

Why Story Matters More Than You Think

When Elizabeth Yin and her co-founders raised money for Hustle Fund, they quickly realized that raising a fund is completely different from raising money for a startup. "I see building this VC as building a startup in itself, it's just that our product is money," Elizabeth noted in an interview.

There's no directory of fund investors. You can't just pitch the same story to everyone. Instead, they used multiple storylines, all true to their mission, to appeal to different investors. Every investor has different motivations for putting capital to work. Your job is to understand what resonates with each person and frame your story accordingly.

The same principle applies when you're syndicating deals or building relationships with other investors. The narrative you construct about why a company matters, why you're the right investor for it, and what success looks like determines whether people want to follow your lead.

The Components of Investment Storytelling

The differentiated insight. The core of any good investment story is a belief about the world that not everyone shares yet. This is where most investors fall flat. They say things like "AI is growing" or "this market is huge" or "the team is great." Those aren't insights. They're observations anyone could make.

Elizabeth Yin has talked about how fundraising is predicated on having a really good differentiated story. She shared an example of a portfolio company that couldn't raise because investors said the space was too crowded and the company wasn't doing anything differentiated enough. The founder noticed a new customer persona emerging among his customers. He rejiggered the story to focus on that persona, which became the basis for a highly differentiated pitch. From there, tweaking the story and business helped generate momentum.

Sometimes it's just a matter of changing the story. A few years ago, Hustle Fund backed a media company at Elizabeth's previous firm. VCs weren't excited about media businesses. The story turned into a "data story" instead, talking about having all these subscribers and learning about them, with that data being useful for many things over time. A differentiated pitch stands out from the crowd.

The founder/company journey. People connect with narrative arcs. Where did this company come from? What problem did the founder experience firsthand that led them here? What has the journey looked like so far?

One of the most memorable pitches Elizabeth Yin has ever seen was from a company called Tales. They created a personalized story for her showing what they were trying to achieve with their mission and business. You could click into subplots around different aspects of their business, from the business model to the product. The story showed they had done their homework on Hustle Fund and what they believe in, talking about removing gatekeepers in publishing and increasing access to aspiring writers. It was informative, creative, unique, and clever. "And yes! I did offer to invest," Elizabeth noted.

The evidence that builds conviction. Stories need substance. What proof points support your thesis? This is where traction, team background, market signals, and competitive dynamics come in.

But here's the thing: you don't need perfect numbers. Eric Bahn, GP at Hustle Fund, values great products and fast shipping. Elizabeth Yin tends to care more about the team and less about whether she believes the current product is great or whether they can fundraise easily. As she shared in Hustle Fund's public data on investment decisions, "even if we don't believe the current product is great or we don't believe the team can fundraise, we're often still willing to make the bet anyway."

What matters is showing ability to execute. Think about traction more in terms of ability to execute rather than specific numbers. Your numbers don't have to be great, but early-stage investors want to see that you can move quickly and experiment with different tactics.

Framing for Different Audiences

When Elizabeth Yin was raising money for Hustle Fund, she and her co-founders realized that different investors cared about different things. They developed multiple storylines, all true to their mission but emphasizing different angles depending on who they were talking to.

The number one angle for everybody? Convincing people of the ROI potential of the fund.

But beyond that, some investors cared about democratizing access to capital. Others were excited about backing underestimated founders. Still others wanted to be part of an innovative firm doing things differently than traditional VCs.

Same fund. Different stories for different audiences.

This applies to individual angel investments too. When you're syndicating a deal or trying to get other investors excited, you need to understand what they care about. Some investors are motivated by impact. Others want the highest possible returns. Some love being associated with exciting companies. Some just want to learn.

Frame your story to match what resonates with each person without being dishonest about the fundamentals.

What Kills a Good Story

Complexity. If someone needs to read your investment thesis three times to understand it, you've lost them. As Hustle Fund advises in their fundraising guide, keep your pitch deck short—ideally 5-10 slides. You should be able to pitch to someone outside your industry and not leave them scratching their heads.

Generic language. Avoid phrases like "leveraging synergies" or "cutting-edge technology" or "robust growth potential." These mean nothing. Use specific details that paint a picture people can actually visualize.

Missing the human element. At the end of the day, investors invest in people. The story needs to include why the founders are uniquely positioned to build this company. What about their background, their relationships, their skills makes them the right team?

As Hustle Fund emphasizes, when evaluating early-stage companies, team matters most. Looking at their public investment data, the team category consistently scores highest across all partners when they decide to invest.

Building Your Storytelling Practice

Great storytelling isn't a natural gift. It's a skill you develop through practice and iteration.

Write investment memos for every deal you do. Force yourself to articulate why you're investing, what you believe, and what success looks like. Over time, you'll develop your own voice and style.

Study how others tell stories. Read investor updates from founders you admire. Notice what makes certain pitch decks compelling. Pay attention to which investment theses stick in your mind and why.

Get feedback. Share your reasoning with other investors and ask what landed and what didn't. The fastest way to improve is to put your ideas out there and see what resonates.

At Angel Squad, investors develop these skills by engaging with a community of 2,000+ angels across 40 countries. You learn by seeing how others frame deals, by discussing investment theses with people who have different perspectives, and by getting real-time feedback on your thinking.

Good stories create momentum. They help people see what you see. They build conviction and make people want to participate. If you're serious about improving your ability to source, evaluate, and win competitive deals, developing your storytelling skills is as important as any other part of your process.