🤝 This week’s edition is sponsored by Alumni Ventures

Ever notice how the juiciest venture deals skip past regular investors?

Not an accident. They're usually saved for institutions with the right connections. AV Syndicates is Alumni Ventures' way of crashing that party.

Alumni Ventures enables accredited investors to co-invest alongside name-brand VC firms like a16z, Sequoia, and Bessemer in early-stage startup deals once reserved for the institutional table. They’re no rookie, either: TIME crowned AV a Top 20 VC firm of 2025, the only one in the top 50 built for everyday investors, with past bets on Groq, Oura, and Axiom Space.

Membership's free, zero pressure to invest, and every deal comes with its own diligence memo.

_{Disclosure: Not an offer to sell, or solicitation of an offer to buy, any security. Venture capital investing involves substantial risk, including risk of loss of all capital invested. Co-investors are provided for illustrative purposes only, do not represent all organizations with which AV co-invests, and are not guarantees of investment outcomes.}

📰 Today's topic: Why Chaos Makes the Case for Spreading Your Bets

The old advice was concentrate.

For years, the venture playbook rewarded conviction. Pick a few names, do all of their follow on rounds, and if you're right, you're really right.

But when you genuinely can't predict how the new technology will shake out, that whole approach starts to wobble.

Nobody knows how this plays out

Look at the pace of disruption right now. In one recent stretch, a single AI company shipped 120 features in 90 days.

Think about what that does to a startup's competitive position.

Innovation is moving faster than anyone's ever seen, throwing challenges at founders that simply didn't exist before.

So if you can't pick the winner with any real confidence, maybe don't try to pick just one.

Bet on teams, spread the risk

This is the counter-narrative. When the ground is shifting, a big, diversified portfolio gets more compelling.

The logic is simple. You're not betting on one product surviving the chaos. You're betting on great teams who can pivot fast when the market moves under them.

A scrappy founder moving at lightning pace can dodge disruption. A concentrated bet on one company can't.

Most of your checks won't work out (and that's fine)

With a diversified portfolio, the majority of your companies don't need to succeed.

You're building for the handful that return the whole thing.

Say you write twenty $2k checks. That's $40k across twenty founders. You're not hoping all twenty become winners.

You're hoping one or two get big enough (50x-100x+) to carry the rest. The other eighteen can fizzle and you're still fine.

That's the power law doing its job. A few outcomes carry everything.

Why now more than ever

We believed in spreading bets back when Hustle Fund was founded in 2017 and we believe it even more today.

When the future is genuinely unknowable, breadth isn't timid. It's the smart play.

– Brian from Angel Squad

📕 Startup term you should know

Ever heard of No Shop Clause?

Basically, this is the "no peeking at other offers" clause. When an investor puts a no-shop clause in a term sheet, they're telling the founder: don't take these terms and go shop them around to other investors to see if you can squeeze out a better deal.

My insider scoop: Brad Feld explains in "Venture Deals" that no-shop clauses usually run 30-60 days, giving investors room to finish due diligence without getting outbid mid-process. Translation for angels: you can ask for exclusivity if you're serious, but founders will only say yes if your terms are competitive and you can move fast.

Overheard in SF…probably

“Investors keep asking about our 'retention.' We're going with the Clubhouse strategy - hope nobody notices we don't have good retention until after the Series B.”