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Founders are often told to chase capital wherever they can find it. In the early days, that advice sounds practical. In reality, it’s dangerous.
Not all angel groups are created equal, and the wrong group can cost you far more than basic dilution. It can slow decisions, distort governance, create misaligned expectations, and introduce social dynamics you’ll be managing long after the check clears.
The best founders don’t ask, “Who will invest?”
They ask, “Who do I want on my cap table for the next ten years?”
The answer starts with culture. But don’t be foolish, you need funding, be smart and efficient.
Watch the Room Before You Pitch
The fastest way to evaluate an angel group is to observe how its members behave when you’re not the center of attention. Sit in on a meeting if possible. Watch the interactions before presentations begin. Are conversations thoughtful or performative? Are people listening — or waiting to speak?
“There is always a halo effect, it can mean additional investment”
During Q&A, pay attention to the quality of questions. Strong groups ask direct, occasionally uncomfortable questions that reveal real risk but aren’t gotcha questions.
The rubber meets the road after the presentations.
Avoid Groups That Confuse Consensus With Intelligence
Some angel groups operate like herds. Everyone waits for a respected lead to speak, then quietly aligns. This may feel efficient, but it’s fragile. When outcomes disappoint — and some always will — these groups unravel quickly.
Founders should prefer groups where investors think independently. Respectful disagreement in the room is a feature, not a flaw. It signals that investors are doing their own work and will remain engaged even when momentum fades.
Pay Attention to the Margins
The real value of an angel group often shows up outside the pitch itself. The strongest groups come alive after presentations end — in small clusters, side conversations, and follow-up discussions.
These moments matter. They reveal whether investors are genuinely curious, willing to lean in, and capable of forming relationships that extend beyond the initial check.
Founders should be wary of groups where everyone disappears immediately after the formal agenda ends.
Understand the Hidden Capital
Successful angel groups are rarely limited to the people in the room. Around the core membership is often a broader halo of capital — friends, former colleagues, family offices, and trusted peers who follow the group’s judgment.
Founders who earn the confidence of a strong angel group often unlock this secondary network organically. That hidden layer of capital can matter more than the initial round itself, especially in follow-on financings.
Ask yourself: Does this group amplify momentum, or does it end at the check?
Respect Groups That Charge Real Membership Fees
From a founder’s perspective, annual membership fees are a positive signal. Groups that charge meaningful dues tend to filter out spectators and service providers, leaving investors who are prepared to deploy capital and engage thoughtfully.
Free groups often attract noise. Paid groups tend to attract commitment.
Look for Investors Who Understand the Long Game
Angel investing isn’t transactional. The best groups know this. Their members understand that capital comes with responsibility — to founders, to each other, and to the process.
Founders should look for groups that talk openly about risk, failure, and time horizons. If a group avoids these topics, it likely hasn’t lived through them.
Choose People, Not Just Checks
Every angel group will tell you about exits. Pay more attention to how they talk about losses. Healthy groups analyze failures without blame. Weak ones go quiet or rewrite history.
You are not just raising capital — you are choosing a community of owners. The right group will challenge you, support you, and stay rational when things get hard.
That matters far more than the valuation on your first term sheet.
— The Letter
