📣 24 hours until our first ever Small Bets LIVE: Angel Investing 101

Tomorrow, we’re hosting a LIVE Angel Investing 101 Bootcamp - with the same Small Bets punch you know and love.

We’ll be covering the basics of angel investing along with an actual founder pitch to Hustle Fund GP, Eric Bahn. Whether you've been investing for years or you're just getting curious about this space, you’ll love it.

📰 Today's topic: Your $5K check isn't the point

Your first angel check is probably going to be small. Maybe $5,000. Maybe less.

That's totally fine. But here's what most new angels get wrong: they think the check is the product. 

It's not. The check is just the entry fee.

The real question founders are asking is: what else do you bring?

Eric Bahn, GP at Hustle Fund, learned this on his very first angel investment - a little company called Webflow.

Today, Webflow is worth north of $4 billion.

How a Product Manager won his way into a Unicorn

When Eric invested in Webflow, he was working as a product manager and didn't have a ton of money to angel invest.

So, he pitched the founders not just on his capital, but on his skills. Specifically, he promised to help with product strategy. And he actually followed through.

One of the first things Eric did was run a persona exercise with the team. (Get all the key people in a room and define, in obsessive detail, who your ideal customer is.)

Not just "freelancers" or "small business owners."

• How much money does this person make? 

• What music do they listen to? 

• And what frustrates them about their current tools?

The Webflow team and a persona named Brad

They defined roughly 60 characteristics for this ideal customer. And from that point forward, whenever the team hit a fork in the road, they'd ask one question: 

What would Brad want?

That single framework helped an early-stage team make faster, more aligned decisions. And it came from an angel investor - not a board member or a fancy consultant.

Eric didn't stop there. He reviewed their product roadmap. Gave feedback on features. Worked directly with team members on specific projects. And, even helped assemble their first IKEA furniture in their first office.

Why this matters for you

A $5,000 check into a company raising $500K is 1% of the round. It doesn’t do much to move the needle financially.

But a $5K check plus a superpower? Now you're interesting.

• Sales background? Help a founder prep for their first enterprise pitch.

• Marketing experience? Run a landing page audit or help nail their positioning.

• Recruiter? Help them source their first two hires.

• Operations nerd? Help set up systems before everything breaks.

Whatever skill you've spent years building, there's an early-stage team that desperately needs it.

TL;DR

Eric put it bluntly: the Webflow founders didn't remember the dollar amount he put in. They remembered who showed up and did the work.

So before your next angel investment, ask yourself: if I took the money away entirely, would this founder still want me involved?

If yes, you're doing it right.

– Brian from Angel Squad

🪽 Angel Investors Come from Everywhere

Spoiler alert: You don't need to be in Silicon Valley or have a trust fund to be a great angel investor.

Ryan Heger | Seattle, Washington

American Diplomat → Startup Transition

Nearly a decade as an American diplomat with global experience in program management, cybersecurity, and risk mitigation. After moving into enterprise sales, Ryan saw that generating inbound demand was the single biggest challenge for companies, which led him to build ContentFork. He also founded SimplCyber to give SMBs access to the kind of enterprise-level cybersecurity normally reserved for Fortune 500s.

Why this matters: Ryan has spent his career tackling complex problems and building trust with people in high-stakes environments. That same focus on problem-solving and relationships now drives how he builds companies.

Ryan is in our angel investing community, Angel Squad. Small Bets subscribers can grab a 30 day guest pass to join them.

Overheard in SF…probably

“Market research is for cowards. We're building what the market doesn't even know it needs yet. Henry Ford vibes.”