The first sentence of my Sequoia profile reads: “Happenstance has been a theme in my life—that, and being open to opportunities.”

Partnering with Sandstone is Exhibit A.

I was introduced to CEO Nick Fleisher by Genevieve Forslund from our talent team. She had flagged Nick as an up-and-comer—someone we should consider either for Sequoia itself or for one of our portfolio companies. She also introduced him to the CEO of a cybersecurity company we’d partnered with.

That CEO fell in love with Nick immediately and gave me explicit marching orders: “Your mission is to help close Nick.”

I happened to be spending a month in New York. Over a few Negronis, I got to know him.

What stood out right away was Nick’s intensity—the hunger to achieve. As a McKinsey alum, I was especially impressed that he made engagement manager at the firm in just 18 months by, in his words, “hacking the system.” McKinsey is famously time-based, but Nick figured out that early specialization—becoming a true domain expert—was the fastest way to short-circuit the ladder. His trampoline was legal tech, which also turned out to be the preamble to his founder story.

At the time, I was very much in pitch mode, trying to recruit him to our cybersecurity portfolio company. Nick’s verdict: “If I were to take a job, this would be the one. But I really want to try my luck starting my own company.” Fair enough, I thought. And of course, the next best thing to recruiting Nick into a portfolio company was partnering with him on his own entrepreneurial journey.

My first question was simple: “What will the company do?”

“Legal tech,” he replied. He told me he’d spent his entire McKinsey career serving general counsels and overlooked mid-market in-house legal teams. Nick knew that AI could give these understaffed and overworked teams real leverage.

That’s where the serendipity kicked in.

Back in 2019, before joining Sequoia, I had seriously considered starting a legal tech company myself. I had just left Google, and I was traveling the world, plotting my next move. The idea came from my time at VMware, where it had taken a team of 10 people to manually extract 62 key terms from licensing contracts. That stuck with me.

I started calling GC friends in the Valley and quickly realized: everyone was doing some version of this. Spreadsheets as databases. Manual toil everywhere. The MVP became obvious—use ML to extract key contract terms and populate a searchable system. This was pre-LLMs, but even then it felt doable. 

Had I started that company, it could easily have evolved into Sandstone: an AI-native workflow engine for in-house legal teams. Sandstone learns from a company’s legal intelligence to execute work and simplify business operations, transforming their roles from reactive to strategic.

At Sequoia, we often talk about the idea of a prepared mind—doing the work on big market shifts before the opportunity shows up. In a sense, I’d been preparing for Sandstone for years. Happily, so had Nick. When he told me his idea, I dusted off my 2019 Product Requirements Document and sent it to him. That may have sealed the deal. 🙂

Historically, legal tech hasn’t been an easy market. But AI has fundamentally changed the dynamics. We’re now seeing multiple legal AI companies scaling quickly, driven by two forces:

1. Law is the perfect LLM use case—the profession is based on text in, text out.
2. AI is most powerful when it automates expensive human toil, and few professions rely so heavily on highly trained people doing repetitive work.

Before Sandstone, Sequoia had already partnered with Harvey (AI lawyer), Crosby (AI-enabled law firm), and Ironclad (AI contracting and contract lifecycle management), so we’d seen these dynamics play out firsthand.

Two months after meeting Nick, we led Sandstone’s pre-seed. Along the way, we got to know his co-founder Jarryd Strydom—another McKinsey alum, and a rare combination of attorney and builder.

Nick and Jarryd accelerated from a standing start. They built the MVP in weeks, put it in front of customers immediately, and recruited an outstanding founding team that matches their intensity. The energy in their Brooklyn office is palpable, and it comes from the top. One of my favorite anecdotes: after a dinner together in NYC, we wrapped around 11pm—and both Nick and Jarryd went straight back to the office.

That speed and execution gave us the conviction to double down and lead Sandstone’s seed round.

And this is just the beginning. Sandstone is well on its way to transforming how legal teams operate and how business gets done.