Online Angel Investing Through Remote Communities

Brian Nichols is the co-founder of Angel Squad, an angel investing community where aspiring and active angels learn from Hustle Fund’s approach, review curated deal flow, and connect with peers.

A startup pitch can reach your laptop without a trip to a local event. Finding people who can help you understand it takes more work. Online angel investing communities bring deal discussions and investor relationships into your week, but you still need a process for evaluating opportunities and deciding how to participate.

What an online angel investing community does

Angel investing means putting your own money into private startups, usually in exchange for ownership or a security that can convert into ownership later. An online community can help you learn the mechanics, meet founders and investors, and discuss potential investments.

At Angel Squad, we combine that peer learning with opportunities sourced by our early-stage venture firm, Hustle Fund. We share deal memos through our community platform and email, covering the company, founders, terms, and why we invested. You choose whether to invest, with no obligation to write a check.

The community and the investment structure have separate jobs. A community provides education and connections. An offering platform can handle a transaction; a special purpose vehicle (SPV) is a legal entity that pools investors' money for a particular investment. Joining a discussion gives you neither ownership nor a guaranteed allocation.

Online startup investing also includes Regulation Crowdfunding offerings through registered intermediaries, with their own eligibility and investment rules. A remote community isn't automatically a crowdfunding intermediary.

Startup investments are speculative and illiquid: you may be unable to sell when you want, and you may have to hold indefinitely. Most of your bets may fail. The Securities and Exchange Commission's (SEC) private-placement guidance highlights potential total loss and limited disclosure. Community membership doesn't remove those risks.

How remote communities build connections beyond your city

Local relationships remain useful. Remote participation lets you learn alongside people you wouldn't meet through your own city's events, provided the community makes room for interaction across time zones.

Our first cohort began in January 2021. As our 2022 community account describes, members wanted deeper connections. We introduced monthly Squad Pals pairings among people in the same time zone. Members also shared their conversations with the wider online group, giving others a reason to reach out.

At that stage, designer members also offered office hours to portfolio founders. Connections took the form of both peer conversations and hands-on founder support.

Our co-founder Elizabeth Yin makes the case for “more varied life perspectives” in Democratizing Knowledge. Different work and life experiences can produce different questions about the same company.

In a hypothetical fintech pitch focused on Brazil, an operator familiar with local customers might ask about onboarding friction that another investor missed. That question needs evidence from customers and the founder. A member's familiarity with a market is a starting point for diligence, the work of investigating an investment.

Build a repeatable remote deal-review process

A written process helps you separate your own reasoning from the enthusiasm in a call or discussion thread. You can practice it while learning, including on deals you pass on.

1. Read the memo and actual documents. Identify what you're buying, how the company plans to use the money, and which claims support the case for investing. Separate founder-provided information, work the lead investor has done, and questions that remain open. A summary doesn't replace the governing documents.
2. Write specific questions before the discussion. For example, ask how customers use the product, what makes them renew, and how much cash the company has left. Our guide to evaluating early-stage founders adds questions about the team's experience and execution.
3. Hear others' reasoning and record your own. Note where you agree, where you disagree, and what information changed your view. Distinguish direct experience from speculation. Written discussion and replays can help across time zones when the provider offers them; a long thread isn't proof that a claim is true.
4. Follow up on unresolved issues. Speak with relevant customers and references when access is available and appropriate. Bring legal and tax questions to independent qualified advisers. If essential information remains unavailable, that uncertainty belongs in your decision.
5. Decide whether to pass or invest. Consider eligibility, the offering's terms, your risk budget, and whether you can leave the money committed for the long term. Passing is a complete decision. Record the reason and revisit your assumptions as new information becomes available.

In Democratizing Knowledge, Elizabeth Yin writes, “The more disciplined you are in your thought process/rubric, the more you can improve over time.” Keeping the same questions and decision notes across opportunities gives you something concrete to learn from. Other investors can challenge your reasoning without making the decision for you.

Questions to ask before joining a remote community

The useful evidence is in the community's operating details. Our broader community selection checklist covers fit and incentives. For remote participation, start with these questions:

1. Will the schedule work? Request a recent calendar. Which sessions are live, which have replays, and how can members in your time zone ask follow-up questions?
2. Where do opportunities come from? Who selects them, using what criteria? Request a sample memo and an explanation of what “curated” means in practice.
3. Who does the diligence? What work does the lead perform, what remains your responsibility, and can members raise concerns or speak with founders?
4. What are the economics and conflicts? Request written membership and transaction charges, including carry, a share of investment profits. Who receives fees? Which vehicle documents govern your investment and rights?
5. Who can invest? Membership and offering eligibility are separate. Our community welcomes learners without accredited-investor status, a legal qualification based on financial or professional criteria. Investing in our relevant offerings requires it. Country restrictions and other requirements depend on the specific offering.
6. How are information and relationships protected? Ask about confidentiality, member privacy, sharing recordings, unsolicited pitches, and moderation. Access to a private discussion doesn't grant permission to circulate a founder's materials.

Offering availability depends on your jurisdiction and eligibility. Curation is the provider's selection process. A Form D notice supplies basic offering information; it carries no SEC approval.

Relationships still need follow-through

A recurring online session creates an opportunity to meet people. Relationships develop through follow-up: sharing a useful question, making a relevant introduction with permission, or offering a skill a founder needs.

You may find it harder to get to know someone through a large video call. Smaller conversations and optional local gatherings can help. Our community's Amsterdam meetup is one example of online connections extending into an in-person meal.

A friendly meetup tells you something about the people you might spend time with. It doesn't establish the quality of an investment. Keep the relationship decision and the investment decision separate, and leave room for thoughtful disagreement.

If you want to learn our approach, discuss startup opportunities, and build relationships with fellow investors through a remote community, apply to Angel Squad.

This content is for educational purposes only and is not investment, legal, or tax advice. Private startup investments are speculative, illiquid, long-term investments with a risk of total loss. Eligibility and terms vary by offering. Seek independent review of the governing documents and your circumstances from qualified legal, tax, and investment professionals before investing.