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

The dirty secret about angel investing is that you're competing against thousands of other people trying to do exactly what you're doing.

At Hustle Fund, we've watched the angel investor landscape explode over the past few years. Our Angel Squad community now has over 2,000 members across 40 countries.

That's incredible for founders who need capital. But it also means that if you're an angel investor trying to get into competitive deals, you need to think carefully about what makes you actually useful to founders.

Most angels don't. They think having money is enough. It's not.

The Actual Competitive Landscape

There's more capital chasing deals right now than most people realize. Elizabeth Yin, co-founder and GP at Hustle Fund, has talked about this extensively. When she moved from operating to investing, one thing shocked her: "I did not appreciate how much money there is in this world."

She points out that what she thought was a differentiated strategy wasn't nearly differentiated enough. At the end of the day, this is all about supply and demand, and there's a lot more capital out there than worthiness to park it.

The result is founders in hot deals can pick and choose. They're not just looking at your check size. They're evaluating what you bring beyond capital.

So what actually matters?

Three Forms of Differentiation That Work

Deep domain expertise in a specific sector. Not "I worked in tech." Not "I invested in SaaS companies." Real, specific knowledge that helps founders avoid mistakes or accelerate growth. If you spent 10 years building fintech infrastructure, that's useful to fintech founders. If you ran growth at three different marketplaces, that matters to marketplace founders.

The key is being narrow enough that founders recognize your value immediately. General business advice is commoditized. Specific tactical knowledge about scaling operations in healthcare compliance or navigating FDA approval processes or optimizing CAC for vertical SaaS? That's scarce.

Access to customers, distribution, or partnerships. Money is everywhere. Intros to your first 50 customers? That's gold. One of Hustle Fund's portfolio founders, Steven Fitzsimmons, broke down his seed round anatomy and noted that his smallest investor, who invested just $5,000, was his most helpful. Small checks can lead to both introductions and more checks.

If you have a network that can materially impact a founder's trajectory, that's real differentiation. But be honest with yourself about whether you actually have that or just think you do.

Track record of helping companies succeed. As Hustle Fund investor Nicole Sanchez noted in a recent Angel Squad event, there's no better way to prove a track record than putting your own personal capital to work. It shows you're really bought into the founders you're investing in, and you've developed a process for sourcing deals, diligencing them, and getting to conviction.

Your portfolio performance speaks louder than your credentials. If your angel investments went on to raise follow-on rounds or achieve meaningful growth, that's evidence you know how to spot talent and add value.

What Doesn't Differentiate You

Here's what founders don't care about as much as you think they do:

Your corporate job. Sorry, but being a VP at a Fortune 500 company doesn't automatically translate to helping a three-person startup figure out their go-to-market strategy.

Your LinkedIn following. Social media presence can help with deal flow, but Elizabeth Yin has said that from a deal flow perspective and track record perspective, networking with other angels who like you and will send deals your way is more effective than broadcasting to the public. "People send companies to people they like, not necessarily because they're famous."

The amount you're willing to invest. Bigger checks sometimes matter, but not always. Plenty of founders prefer strategic $5,000 checks over passive $50,000 ones.

Finding Your Lane

The investors who win competitive deals aren't trying to be everything to everyone. They've found a specific lane where they can genuinely help.

This is exactly what Hustle Fund did when raising their own fund. After realizing the market was flooded with "AI funds" and "SaaS funds" with little real differentiation, they went deeper. They realized that 81% of the economy being underinvested was too vast, so they needed to find their specific lane within that. With that concentration, they got more compounding because deals in the periphery just fell away.

The same principle applies to angel investors. Pick a sector, a geography, a founder demographic, or a go-to-market motion that you genuinely understand. Then build real expertise and relationships there.

Proving Your Value

Actions matter more than words. Don't just tell founders you can help. Show them.

Write content that demonstrates your knowledge. Make intros without being asked. Share tactical insights that founders actually use. The investors who get into hot deals are the ones who've already proven their value to other founders.

At Angel Squad, we see this play out constantly. The most sought-after investors in our community aren't the ones with the biggest checks or fanciest credentials. They're the ones who've helped portfolio companies hire key people, land initial customers, or navigate tricky strategic decisions.

If you want better deal flow, focus less on your positioning statement and more on becoming genuinely useful to a specific type of founder. The differentiation will follow.

And if you're serious about developing these skills and getting connected to quality deal flow, consider joining communities where you can learn alongside other angels who are also building their track records. 

Angel Squad offers access to vetted deals, education on investment frameworks, and a network of investors who can help sharpen your approach to finding and winning competitive deals.