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

I get asked this question constantly: "Should I join Angel Squad, invest through a rolling fund, or just raise my own micro-VC?"

It depends on whether you want to learn, whether you want to manage other people's money, and whether you have about five years to burn.

The Economics Are Wildly Different

Let's start with the money, because that's what everyone cares about but nobody wants to talk about directly.

Angel investing communities (like Angel Squad): You pay a membership fee (around $875/quarter or $3,500 for lifetime access). Then you deploy your own capital into deals, typically $1K-$5K per company. You keep 100% of your returns. No carry, no management fee on your investments.

Rolling funds: You're the GP. You collect 2% management fees and 20% carry. Sounds great until you do the math. A $2M rolling fund gives you $40K/year to live on before expenses. Good luck.

Traditional VC fund: Same 2-and-20 model, but you raise it all upfront. A $10M fund nets you $200K/year in management fees, split among partners. After rent, travel, and legal fees, each partner might take home $50K-$60K. For ten years of work.

Most fund managers don't make real money until carry kicks in, which takes 7-10 years. Elizabeth Yin has written about this: even successful fund managers often have worse cash positions than the startups they back.

Time Commitment

Angel investing community: Maybe 2-5 hours per week. Attend some pitch sessions, do your own diligence, write checks. You control your time.

Rolling fund: This is a full-time job pretending to be a side project. You're constantly fundraising (quarterly!), managing LP relationships, sourcing deals, doing diligence, and handling compliance. Plan for 40+ hours per week.

VC fund: Also full-time, but at least you fundraised once and can focus on investing for a few years. Still, expect 60-hour weeks between deal flow, portfolio support, and LP management.

Most people romanticize the GP title without counting the hours. If you have a day job you actually like, running a fund will destroy it.

Deal Flow Reality Check

This is where things get interesting.

Angel communities give you curated deal flow from established funds. Angel Squad members see deals Hustle Fund has already vetted from their 1,000+ monthly pipeline. You're not sourcing, you're selecting. That's a huge advantage when you're learning.

Rolling funds force you to source your own deals. Unless you're already well-known in startup circles, you're chasing deals that better-known funds passed on. It's not impossible, but it's hard.

VC funds have brand power working for them. A $10M fund can still attract decent deal flow if the partners have good reputations. But you're competing with everyone else for the best companies.

Deal flow isn't about seeing lots of deals. It's about seeing the right deals. Quality over quantity. Angel Squad members get 2-3 highly vetted opportunities per month from a fund that's backed companies like Webflow (where a $1K investment would now be worth $500K). That's often better than seeing 50 cold inbound deals.

The Learning Curve Problem

Angel communities are designed for learning. You see pitch decks, hear founder pitches, watch experienced investors ask questions, and gradually build pattern recognition. It's like a paid apprenticeship.

Rolling funds assume you already know what you're doing. Your LPs expect you to be the expert. There's no room to admit "I'm still learning how to evaluate pre-revenue SaaS companies."

VC funds same deal. You're the professional. Nobody cares about your learning curve.

The math is simple: if you need 20-30 investments to build solid pattern recognition, you better have a structure that supports that learning without risking other people's money first.

Regulation and Headaches

Angel communities: Zero regulatory burden. You're investing your own money. Done.

Rolling funds and VC funds: Welcome to compliance hell. You need fund admin, lawyers, tax accountants, and someone to handle K-1s. Hustle Fund has written extensively about why international investments create tax nightmares and why non-Delaware C-corps are a pain.

For a $2M rolling fund, expect to spend $30K-$50K annually on fund admin and legal. That comes out of your already-thin management fees.

The Path Most People Should Take

Here's the honest path for 95% of people reading this:

Start with an angel investing community. Make 10-15 investments of $1K-$3K each. Build your pattern recognition. Figure out your thesis. Make mistakes with your own money, not LP capital.

After 2-3 years and a portfolio of 15-20 companies, if you're seeing deal flow nobody else sees and founders are begging you to invest, maybe consider a rolling fund.

If that rolling fund works for 2-3 years and you've got strong returns and happy LPs, then maybe, possibly, consider raising a traditional fund.

But skipping straight to fund management is like trying to play in the NBA after one season of high school basketball. Technically possible, theoretically impressive, practically disastrous.

What Angel Squad Members Actually Do

About 10% of Angel Squad members go on to start their own funds or syndicates. But they do it after gaining the experience and network to actually succeed.

The other 90% keep angel investing, keep learning, and keep building their portfolios without the headache of managing other people's money. They're probably happier and, in many cases, making more money than the fund managers.

One Squad member put it perfectly: "I'd rather own 100% of my $50K portfolio's upside than 20% of a $2M fund's upside, especially when the math probably works out the same and I keep my day job."

The point of angel investing isn't to become a VC. It's to build wealth by backing great founders while learning about startup ecosystems. If that leads to fund management, great. If it doesn't, also great.