🤝 This edition is sponsored by Alumni Ventures

AI companies, deep tech, quantum computing, cybersecurity, space — they don't exactly show up in your inbox. They go to the big VC firms first. a16z, Bessemer, Y Combinator. You know the names.

Alumni Ventures lets accredited investors get into those same deals. Like, literally co-investing alongside those firms. No, we're not joking.

And it costs nothing to join. You browse the deals, you invest if something catches your eye, and you walk away if it doesn't. Zero obligation, zero pressure.

📰 Today's topic: Yes, money complicates relationships. Do it anyway.

Most angel investing content sells you the financial upside. The 100x exits. The Uber comps. The math.

What gets undersold? The relationships. They're often the best part of the whole thing.

But money amplifies every relationship it touches. Both directions. The wins feel bigger. The losses feel more personal. Once you get that, you can lean into it instead of being scared of it.

Why this is a good thing

Every $5k check you write puts you on the cap table of someone building something hard. You're not just a line item. You're someone they remember.

Founders never forget who showed up early. The check from a stranger gets cashed and forgotten. The check from a believer gets remembered for a decade.

That relationship pays you back in ways that don't show up on a spreadsheet. Intros to other founders. Invites to closed-door dinners. First looks at their next company. Sometimes a champion who walks you into rooms you'd never get into on your own.

The hard parts are real, but rare

I'm not going to pretend the messy moments don't happen. They do.

Sometimes a friend's company fails and they get weird about it. Sometimes a founder pivots without telling you. Sometimes you and another angel disagree about a deal and a friendship cools.

Elizabeth Yin, GP of Hustle Fund, puts it plainly:

"The #1 complaint I've heard about startup investing is that people don't realize they would have to mediate or deal with lots of people problems."

None of this should scare you off. It just means you go in with eyes open.

Three habits that handle most of it

You don't need a 50-page playbook. Three habits cover the vast majority of situations:

• Treat the check as gone. Decide upfront that if the company fails, the money is fine. You'll never resent a friend over $5k you already wrote off.

• Set the communication rhythm early. Quarterly updates? When things blow up? Say it once, then stop wondering.

• Never bring up the money. The worst angels are the ones who keep asking when they'll get paid back. Don't be that person.

Lean into it

Money amplifies relationships. That's the feature, not the bug.

The angels I admire most have built networks of founders who'd take their call in a hurricane. That happens because they wrote early checks, helped where they could, and never made it weird about the money.

– Brian from Angel Squad

🍫 A snack for the road: A taste of Angel Squad

Ever wonder what it's like to learn angel investing from people who do it for a living? Here’s a sneak peak on Angel Squad — Hustle Fund's community for the next wave of angel investors.

Inside, you'll find a quick highlight reel and a full 60-minute event.

Angel Squad is built for both brand-new and seasoned investors : weekly events, tactical courses, and the actual tools you need to make smarter bets. Oh, and members get to put their learning to work by writing $1k+ checks into Hustle Fund's top portfolio companies.

The content usually lives behind a members-only wall, so this is a freebie. If you like it, we'd love for you to schedule a call at the end of this course.

Check it out here →

Overheard in SF…probably

“Yeah we're down to 2 months runway, but remember - Airbnb sold cereal boxes to stay alive. We haven't tried cereal yet.”