Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups.

Lachy Groom has one of the most impressive angel investing track records of the last five years. He's backed companies like Figma, Notion, Lattice, and Ramp before they became household names in the startup world.

But here's what makes studying Lachy Groom investments interesting: he's not a traditional VC. He started as an operator at Stripe, then transitioned to full-time angel investing with a strategy that's both disciplined and contrarian.

Let me break down what makes his approach work and what early-stage investors can learn from it.

Who is Lachy Groom?

Lachy joined Stripe in 2014 as one of the company's early employees. He spent several years there in various roles, eventually leading growth initiatives. That experience gave him a front-row seat to how one of the decade's most successful startups scaled from small team to multi-billion dollar company.

In 2018, Lachy left Stripe to focus on angel investing full-time. And he's been killing it ever since. His portfolio includes some of the fastest-growing B2B companies of the last few years.

What's wild is that Lachy doesn't run a traditional fund. He invests his own capital, stays super selective, and focuses on being genuinely helpful to founders rather than deploying massive amounts of capital.

What Makes Lachy's Investment Thesis Different?

Looking at Lachy Groom investments, some clear patterns emerge that separate him from typical angel investors:

He invests in tools that developers and operators love first, then monetize later: Figma started as a design tool that designers loved using. Notion was a productivity tool that individuals adopted before companies paid for it. Lachy understands this bottom-up adoption model better than most investors because he lived it at Stripe.

He backs technical founders solving painful workflow problems: Almost every company in Lachy's portfolio is building software that makes knowledge workers more productive. These aren't consumer apps or marketplaces. They're tools that save people time and make their work better.

He gets in early and writes meaningful checks: Lachy isn't writing $5k angel checks to 100 companies. He's writing $100k-$500k checks to a handful of companies where he can actually be helpful. This approach means he's selective, but it also means founders take his involvement seriously.

Breaking Down Specific Lachy Groom Investments

Let's look at some actual investments and what they reveal about his thinking:

Figma

Lachy invested in Figma's Series A in 2018 when the company was valued around $94 million. At the time, most people thought Adobe had design software locked up. But Lachy saw what was happening with bottom-up adoption among designers.

Figma eventually sold to Adobe for $20 billion. That's a roughly 200x return in about four years. Not bad.

But here's the insight: Lachy didn't invest because he predicted Adobe would acquire Figma. He invested because designers were switching from Sketch to Figma organically, and the product enabled real-time collaboration that existing tools couldn't match.

Notion

Notion is another perfect example of Lachy's thesis in action. When he invested (reportedly in 2019), Notion was mostly used by individuals for personal productivity. But Lachy saw how it could expand into team and enterprise use cases.

The key insight? When individual contributors love a tool and advocate for it internally, that creates a path to enterprise sales without traditional top-down selling. This is the same playbook that worked for Slack, Dropbox, and (surprise) Stripe.

Ramp

Ramp is a corporate card and expense management platform. On the surface, this looks like a crowded category. You've got Brex, Divvy (acquired by Bill.com), and traditional corporate card providers.

But Lachy invested in Ramp's seed round because the founders (who previously built Paribus, acquired by Capital One) understood fintech deeply and were building a product that finance teams actually wanted to use.

Again, the pattern: painful workflow problem, bottom-up adoption, technical founders with domain expertise.

Lattice

Lattice builds performance management software for HR teams. Lachy invested early (around 2016-2017) when the company was still figuring out product-market fit.

This one's interesting because HR software has historically been terrible. But Lattice was building software that managers and employees actually wanted to use for feedback and goal-setting, not just software that HR departments mandated.

Same playbook: make the end users love the product, then expand from there.

What's Lachy's Secret Sauce?

After studying Lachy Groom investments for a while, I think his edge comes down to a few things:

He has deep operational expertise from Stripe: Lachy isn't just writing checks and hoping for the best. He knows what it takes to scale a company from $10M to $100M in revenue. He understands go-to-market, pricing, hiring, and product development at a level most angel investors don't.

He focuses on product-market fit signals, not vanity metrics: Lachy doesn't care if a company has impressive PR or raised from famous VCs. He cares if users love the product and are spreading it organically. That's way harder to fake than growth metrics.

He invests in markets he understands: Almost every Lachy Groom investment is in B2B SaaS, productivity tools, or developer infrastructure. He's not investing in consumer apps, healthcare, or climate tech. He stays in his lane.

What Can Early-Stage Investors Learn?

Here's what Lachy's approach teaches us about early-stage investing:

1. Specialize in What You Know

Lachy built his entire investing strategy around insights from working at Stripe. He understands B2B SaaS, bottom-up adoption, and how companies scale. He doesn't pretend to have expertise in areas he doesn't.

For angel investors, this means: invest in industries where you have unfair advantages from your career. If you spent 10 years in healthcare, invest in healthcare companies. If you built developer tools, invest in developer tools.

2. Look for Organic Adoption, Not Paid Growth

Lachy invests in products that spread through word-of-mouth and genuine user love. If a company needs to spend heavily on ads or sales to acquire customers, he's probably not interested.

This is a great filter for early-stage investors. Ask founders: "How are you acquiring your first 100 customers?" If the answer involves heavy paid marketing, be skeptical.

3. Write Bigger Checks to Fewer Companies

Lachy doesn't spray and pray. He makes concentrated bets where he can add real value. For angel investors with limited capital, this is actually smart. It's better to write $25k checks to 4 companies where you can be helpful than $5k checks to 20 companies where you're basically irrelevant.

4. Value Access Over Brand

Lachy doesn't lead rounds or need his name on the cap table for ego reasons. He invests in companies where he genuinely believes he can help and where the founders want him involved. That approach gets him access to the best deals because founders actually want to work with him.

The Reality Check

Here's the thing about Lachy Groom investments: he has an unfair advantage that most angel investors don't have. He worked at Stripe during its hypergrowth phase. That gives him credibility, network, and pattern recognition that takes years to build.

But the principles still apply even if you don't have that background. Focus on industries where you have expertise. Look for organic adoption. Be helpful to founders. Write meaningful checks to companies where you can add value.

If you're looking to connect with other early-stage investors who take this operator-first approach to investing, Angel Squad brings together people who've built companies and want to back the next generation of founders doing the same.

Key takeaways:

• Invest in bottom-up adoption models where end users love the product first
• Back technical founders solving painful workflow problems
• Focus on industries where you have genuine expertise
• Write bigger checks to fewer companies where you can actually help
• Look for organic growth, not paid acquisition

Lachy's success isn't magic. It's pattern recognition from operating experience, discipline to stay focused on what he knows, and genuine helpfulness to founders. Those are all things early-stage investors can learn from and apply, regardless of whether you have a Stripe background.