What's in a Name?

Your story, in 1 word.

One of my favorite questions to ask a founder in a first meeting is why they picked the name for their company. It says a lot about a person — what they value, what they hope to communicate to the world around them, how they want to show up. Whether you gave it thought or not, it says a lot.

Venturing as a practice

I named this writing project "The Art of Venturing" because it represents my personal creative effort to venture outside my own comfort zone, while also acknowledging and celebrating how much art (versus science) actually goes into the process of venturing into something new — something most people might define as "risky" or uncharted. Whether you are starting a new company, climbing Kilimanjaro, or writing a new book, there is always a moment just before you take the leap into the unknown. That moment is so pure, so human — it is when you suspend all logic and disbelief, and despite most voices in your head telling you to stop and avoid danger, you just do it anyway. I'm obsessed with that moment, and have become even more obsessed with understanding how and why people decide to take that leap.

What drives the human desire to venture into the unknown?

A LOT of people talk about doing this or that, starting this or that… we know them, we are them. But we all know how hard it is to really start something, and even harder to keep going. Every day, showing up and putting one foot in front of the other… it never seems like much progress is being made, until years later, you look back and realize — wow, I've come pretty far. You look forward again and think, wow, I've got a long way to go.

Venturing as a job

I've been in the business of investing in startup founders and companies for about 15 years now. It's long enough to know I'm not bad at the job, but not quite long enough to know if I'll meet the bar for "exceptional." I'd objectively say I'm pretty good. I have a lot of winners, certainly if the IPO markets would stabilize. I've returned a lot of money back to my LPs (limited partners / investors). I've had the privilege of supporting incredible people as they build some generation-defining companies that have changed people's lives. I'm now old enough in the industry where when I say I'm old, no one says anything back, they just nod and occasionally note that I look great (for my age).

Not gut-instincts — Heart instincts

What often comes with this hard-earned "wisdom" is the question:

How do you pick the winners? How do you know?

I've spent some time reflecting on this simple yet nuanced question.

• Did I really "know" something was going to be a huge winner when I first invested?

• Did I really "know" how the market dynamics were going to play out?

• Or did I just have a sense of something special in a founder, in an idea, and then just decide to do it?

When I look at investment opportunities now, I am most drawn to the ones where deep in my heart I feel like if I don't play a part in bringing this to life, I'll regret it.

This company or idea just HAS to exist in the world.

That's a pretty tight filter to get through when I'm seeing 1000+ deals a year. But you'd be surprised, there are some amazing founders out there passionate about solving really important problems. But of course I can't back them all. I have to be true to my own strengths and focus on the problems I'm best positioned to solve.

Seeing the unseen

But coming back to the name, The Art of Venturing… so much of that final "leap" I take before making an investment is in the art of seeing what can't yet be seen. I notice ripples of behavior, subtle changes in sentiment. I notice the feeling, not just the numbers or the technology. Those are easy to assess (and I do assess them) — they are tangible and quantifiable. But to really gauge whether something can have an outsized impact on the world, you have to know people. You have to know what we care about, where we hurt, and what brings us joy.

Maybe that sounds crazy, but practically speaking, some of my biggest winners are: a dog food company, a luggage company, an acne medication company, a sleep tracker, a sport nutrition retailer, an edge-computing based AI platform, and a budgeting app. That list doesn't sound terribly exceptional by any stretch of the imagination.

Except to me, I saw: a company delivering healthy food for my precious best friend (The Farmer's Dog); a company that represents my home away from home and brings out the spirit of wanderlust and curiosity deep inside me (Away); a company that helps me be more confident and naturally beautiful (Curology); a foundational health tool that helps me be healthier every day (Oura Ring); a place to get the nutrition I need while I push myself to my limits (The Feed); the only AI company looking out for my privacy and security (WebAI); and the first financial services platform to bring wealth planning and management to everyone, not just the already rich (Monarch Money).

I can honestly say, every single one of these investments did feel like Must-Have, Must-Win investments from the very beginning.

But of course between start and now, a LOT of ups and downs ensued (and continue to ensue). Some will make it all the way and drive outsized venture returns. Some won't because they got caught in the unfortunate market cycle or a black swan event (you can imagine COVID wasn't awesome for the travel industry).

What Matters

This is why I love asking about company names in first meetings. It's not small talk — it's a window into someone's soul. The founder who named their company after their grandmother reveals something about legacy and family values. The one who chose a made-up word that sounds like "trust" or "growth" tells you they think about brand and perception. The one who picked something completely functional shows you they're focused on the product above all else.

Each choice reveals what matters most to them. And in venture, understanding what matters most to someone is everything.

When I named this project "The Art of Venturing," I wasn't just picking a catchy title. I was declaring that this work — whether it's investing, writing, or any creative endeavor — is fundamentally about courage, intuition, and the willingness to leap into uncertainty. That the best decisions come not from spreadsheets and market analysis (though those have their place), but from that deeper place where logic meets instinct.

Every name tells a story. Every story reveals what we value. And every value system shapes how we see the world and what we choose to build in it.

So next time someone asks you about your company name, your project name, even your own name — remember that you're not just explaining etymology. You're sharing a piece of who you are and what you believe is worth creating in this world.

That's pretty powerful.