I didn't go to an Ivy League school, so breaking into VC felt impossible.

Instead, I found my way through the side door. I started at Lyft during the pink mustache days, co-founded their employee syndicate, and helped 300+ employees deploy $30M into startups.

That led me to help other tech companies (Airbnb, Square, Pinterest, Stripe) build their own alumni investing communities.

Eventually, I realized my real passion was making angel investing accessible to people who aren't in the traditional VC club.

That's how Angel Squad was born.

Today, I run Angel Squad at Hustle Fund. It's a community of 2,000+ professionals learning how to angel invest. TechCrunch called us the "YC of Angel Investing."

We've deployed $30M+ together, and our members include everyone from Google PMs to airline pilots to physical therapists. Basically, anyone who wants to learn how to write $1k checks into startups.

I also write Small Bets, a weekly newsletter where I share lessons on startups and angel investing - the wins, the losses, and everything in between.

If you're curious about angel investing or just want to learn more about the startup world, let's connect.

Brian Nichols

Last week my 7-year-old and I built a math app together. No code. Done in an afternoon. Genuinely better than the games I've paid for on the App Store.

That same week, one of our GPs cut her email workload by 50% using a personal AI agent she built herself. I got the bug bad enough that I splurged on a Mac Mini.

Something has crossed a threshold. Tools like Claude Cowork and Claude Code aren't "AI helps you write emails" territory anymore. We're talking agents that take over your browser, triage your inbox, draft responses, and run tasks on a schedule while you sleep. 

I say this as someone who is decidedly not a software engineer: the theoretical just became very, very tangible.

Every major platform shift creates a new generation of massive companies - and founders are right now building the infrastructure for how AI agents browse the web, make purchases, and communicate with each other. 

Think the internet in 1995, except the entire web needs to be rebuilt for machines, not humans.

That's a lot of companies that need to get built fast.

Which, makes this one of the best windows in history to be an early-stage investor. 

When kicking around the idea for this event, I realized that this is the first generational platform shift where $1k checks are a legitimate entry point. 

You don't need to be a GP or a big-shot angel writing $100k minimums to participate. The best angels in our network started small, stacked reps, and built real networks along the way.

Those days of "you can't play unless you're already in" - they're over. So for the first time ever, I’m taking my Small Bets newsletter LIVE for an Angel Investing 101 Bootcamp. 

45 minutes. 

You’ll hear my thoughts on why now is an incredible time to be an angel, and get to watch a fundraising founder pitch Hustle Fund GP Eric Bahn live. 
 
🦞 RSVP while we have space. This one’s gonna be big: https://luma.com/t6n3x6kl

Founder of Angel Squad | I write about startups, investing, and hard-earned lessons | Small Bets newsletter

Open article: 🎥 Small Bets LIVE: Angel Investing 101 Bootcamp · Zoom · Luma by luma.com

🎥 Small Bets LIVE: Angel Investing 101 Bootcamp · Zoom · Luma

Almost 2.5x more people joined Angel Squad so far to start this year vs. last year.

That number surprised me a little.

But what surprised me more was who joined.

+ A former Major League Baseball player. 
+ A pharma professional investing on the side. 
+ A private funds lawyer whose VC clients finally convinced her to write her own checks. 
+ A robotics engineer. 
+ A Stanford sophomore. 
+ A Harvard Law-trained AI strategy consultant. 

The professions are all over the place too:

+ ML scientists and senior engineers at big tech companies
+ Fintech operators, fractional CFOs, startup lawyers
+ Product managers, UX designers, enterprise sales reps
+ Ex-Goldman analysts, ex-McKinsey consultants
+ Founders who've exited and are ready to back others

Members joined from Europe, Southeast Asia, East Asia, LATAM, MENA, Australia, Kenya, Taiwan - and nearly every region of the US.

This is what I kept hoping Angel Squad would become.

Not another room full of Sand Hill insiders passing deals to each other. 

A place where the robotics engineer and the startup lawyer and the ex-baseball player can all learn this asset class together - and actually invest alongside each other.

Oh, and don't forget the best part...they all meet our strict "no a-holes allowed" policy.

AI captured nearly 50% of all global venture funding last year. Over $200 billion.
Most people have no way to access these companies before they IPO.

Every major tech wave creates a new generation of massive companies. The internet gave us Google and Amazon. Social gave us Meta. Mobile gave us Uber and Airbnb.

We're in the middle of the next one. 

Founders are building new infrastructure for how AI agents browse the web, make purchases, and talk to each other. It's like 1995 for the internet, except the web is being rebuilt for machines, not humans.

A lot of companies need to get built. 

A lot of opportunities for early investors to get in.

The best news is that this wave is different because you don't need to be a full-time VC or write $100K checks to participate.

Most of the best investors in our Angel Squad community start with $1K-$5K checks. Learned from the reps. Built real networks along the way.

We're taking our Small Bets newsletter (55K+ subscribers) live for the first time ever. 45-minute bootcamp. 

We already have 300+ RSVPs.

I'll break down how angel investing actually works and why the timing is so good right now.

Then a real founder is going to pitch Eric Bahn, GP at Hustle Fund, on the spot. 

Shark Tank style (except Eric is super nice).

You'll watch Eric evaluate the deal in real time, and he might invest on the spot. 

Whether you're an experienced investor or you're just getting curious about the space, come hang.

RSVP below. We'll send the recording to everyone who signs up.

👉 https://luma.com/t6n3x6kl

Paul Thorogood

Designer // Product Love //  Inventor // Customer Experience Builder // Traveller

Paul, a seasoned Designer, Product Executive, and brand builder, adeptly navigates the convergence of our digital and physical realms. With over 15 years of experience in delivering thoughtful, well-crafted products, brands, and experiences, his mission is to forge indelible data-driven connections for companies and their customers. This is achieved through a symbiotic relationship between the consumer, product, brand, storytelling, data, and technology, propelling growth and fostering stability.

Paul thrives in the dynamic environments of early-stage start-ups and established businesses seeking new horizons. His success lies in his ability to unite technology and design-focused teams, laying the groundwork for future growth with confidence and finesse.

As an internal entrepreneur, Paul has led product vision and strategy across B2B and D2C environments at MOO.COM, Packlane, Teespring, and Crane Stationery. He has always established new levels of innovation, leveraging human-centered design and his experience to create growth and increase customer loyalty.

Paul has carved a niche for himself as a unique expert in on-demand product personalization and direct-to-consumer e-commerce across diverse categories, including packaging, apparel, jewelry, and print. His direct collaborations with industry giants and startups have been instrumental in driving innovation, leaving a lasting impression on the industry.

His work has connected tens of millions of consumers to physical products through online interactions and in-store immersive experiences that capture the imagination.

Paul’s skills bring together all the departments needed to support and execute groundbreaking product strategies and launch companies.

 International Jury Member

Good AI is…

🔹  as little AI as possible.
🤫  quietly woven into the work.
👯  built around human control and expectations.
🫶  a teammate, not a replacement.

In the 2010s, we had a Bluetooth arms race.

For a few years, everything needed Bluetooth.

Toothbrushes. Luggage. Water bottles.

Not because the job required it.

But because it was the new shiny feature listed. 

We’ve entered the same phase with AI.
Add a chatbot.
Add a copilot.
Add “AI-powered” to the homepage.

But when technology matures, it stops being the headline.

Research is already pointing in that direction.

Nielsen Norman Group has shown that bolted-on AI features reduce usability and trust. Measured integration outperforms spectacle.

Penn State researchers found that when systems meet expectations, people don’t even need explanations. When they don’t, trust drops.

MIT Sloan and Microsoft research both point to the same conclusion: performance improves when humans stay engaged. Not when they step aside.

That’s the thread.
Good AI reduces friction.
It reduces error.
It reduces waste.
It shouldn’t reduce humans.

If a customer can feel the system working better, but doesn’t need to be told why — that’s usually the right balance.

I’m optimistic about AI in the workflow.

I’m cautious about AI as theatre.

Bluetooth didn’t disappear.

It was absorbed to make the product effective.

The same will happen here.

What will remain are the systems in which the technology disappears, and the human feels more capable.

That’s the leverage.

At the consumer level, AI is a feature, not the product.

#AI #ProductDesign #HumanCenteredDesign #Innovation #FutureOfWork

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