Douglas Leone

By the time I was leaving, I was all the people driven investor.

You know, Doug Leone had this statement.

I never understood it in the beginning.

In venture, you can lose 1x your money, but you can make 100x your money.

So I just think those are the variables I look for.

And if those traits start coming together, even if it's not perfect, I start leaning in.

I think the thing I realized, you know, Doug Leone had the statement years ago, like I'd listened to it and I never understood it in the beginning.

uh his point was like hey if you in venture you can lose one x your money but you can make 100 x your money so if you're on the fence you should lean in and when i first heard it i candidly thought but how will that work because then you'll do a lot of investment i get the asymmetric risk reward but you'll create a portfolio that will become like drowning of the time what i realized is his statement holds true only if you have a high bar on founder quality If you have a high bar on founder quality, which is rarely are you impressed with people, then when you're on the fence, you should lean in.

And I went really deep on Sequoia.

You know, there was Doug Leone was there and this this is kind of refiltered in years since.

But, you know, Doug Leone is the kind of guy and he used to run the firm where you'd show up at 4 a.m. at the office hoping you were the first one there and like he's already there.

Or it's like, oh, I went swimming.

I worked out at 4.30. What were you doing? And I've taken phone calls after midnight from him about stories.

So I think that's what you want from him.

But you could be a great... sort of product helping or strategy helping VC where you want something very different.

So I think like in every firm, you know, look at Sequoia, you have the Doug Leone type, and then you have Alfred Lin, who has been number one on the Midas list a few times, who has his own like legendary portfolio.

You can ask one question that you find most revealing of a founder quality.

Doug Leone's to me was the one I remember most, and he always says, "What's your worst reference?"

So, you know, that's a great question.

I generally ask your five best friends, right, and imagine they're in a room, and if I had to ask them three words to describe you, what would that be? That's the question I normally ask people.

Typically, the executive chair or chair of a venture or private equity firm is the senior managing partner or founder of the firm.

For instance, the chairman at Menlo Park California-based Sequoia Capital, an early investor in Apple and Google and which reportedly manages more than $85 billion in funds, is Doug Leone, the former managing partner of the firm.

Similarly, at the Carlyle Group, a Washington, D.C.-based private equity firm managing $485 billion, the co-chairman is David Rubenstein, former co-CEO and co-founder of the firm.

Noraya had no prior role at any venture firm or as a venture investor.

His task is no longer to prove that a Brazilian startup can beat the Goliaths at home or in its neighborhood, but that it can compete and win on a global stage.

In the course of reporting this story between Sao Paulo and Miami, I spoke with Doug Leone, the longtime partner at Sequoia Capital, who backed NewBank in its earliest years.

"'There are the Elon Musks and Steve Jobses of the world, and they're fantastic,' he told me.

"'But there are also these people who were still early enough in their careers that we don't fully see what they might become.' Bill Gates wasn't Bill Gates for the first 20 years.

Between the summers of 2008 and 2010, he spent more and more of his time and energy on financial services.

By the fall of 2010, He decided to return to Stanford for business school, which he envisioned as a vacation during which he'd figure out what business to start.

Then a classmate, David George, learned through Doug Leone that Sequoia was looking at Latin America and introduced him to Vélez.

A couple weeks into his first quarter of business school, Velez drove the two miles from Stanford to Sequoia's Sand Hill Road office to meet with Leone.

I, I, we're a family friendly podcast, so I can't share the specifics.

I would tell you that Doug Leone has some like rules for relationships that are obscene and ridiculous, but they're true.

And so, you know, if you ever get into a conversation with him and you ask him his rules, you're you will nod your head and you will be like, I can't believe you said those things out loud.

But those are things that I occasionally think about.

And if you need a quantum computer to basically protect yourself from a quantum computer, it's too late.

I, I highly recommend, um, Doug Leone, um, one of the, the very senior people at Sequoia, recently did a long podcast with David Senra.

And he said, "You know, there's a reason why we all sell too early as VCs." He says, "It's because in general, most companies, if you follow them out a few decades, they go away.

And why do they go away? Because they don't innovate enough to not be replaced by new tech," right?

So we're still using that.

And there was an inksign letter, and no one sends any letters anymore, from Doug Leone and Mark Kwame to my father stating that the Silicon Valley is awashed of capital.

And to be honest with you, immigrant generation, I didn't look at what awash meant, so I Googled it.

Flooded.