max_levchinLast year the well-heeled, Wall Street-y and mostly male audience at All Things D’s annual conference were flummoxed watching a demo of True & Co., a company that helps women alleviate the anxiety of bra shopping. Many of them shifted uncomfortably in their seats murmuring things like “Is this a joke?” and “This is really a problem?”

True is actually a compelling solution to a real problem. But somehow it didn’t seem like the time or place to discuss it.

This year Max Levchin one-upped that by demoing a product no one expected him to create next — and repeating the phrase “cervical mucous” half a dozen times during his pitch.

You may know the name Max Levchin. He was the co-founder of PayPal, one of the dons of the PayPal mafia, and the founder of Slide. He was also one of the primary subjects of my first book, “Once You’re Lucky, Twice You’re Good.” From 2006 to 2008 I followed Levchin around, along with others driving the early days of the Web 2.0 movement. Out of gratitude, I have mostly given him a break from me since. In fact, the last time I wrote about him was when he sold his second company, Slide to Google. So I didn’t know what he was up to before he took the stage to launch Glow, his big data fertility app.

The demo was the talk of D. Aging entrepreneurs and female attendees who’ve struggled with fertility issues were captivated by it, and everyone else was just…well, surprised. I doubt even the shrewdest Valley insiders would have guessed this would be the problem Levchin would tackle next. For one thing, he’s a guy. For another, he and his wife haven’t had issues with fertility.

But as someone who has spent years delving into Levchin’s entrepreneurial psyche, I was smiling broadly watching his demo. It may not seem like it, but this is such a Max Levchin company. It’s all about math and science and solving real, hard problems that almost no one else cares about.

He’s back. He’s done throwing virtual sheep, and he’s playing to his strengths again. And for anyone who cares about this space, that’s very much a good thing.

First, some context. Levchin is one of the most data- and research-obsessed people I’ve ever met. He’s gone through life graphing nearly everything. He even once graphed girlfriend’s bra sizes over time to see how his taste in women was changing. When he proposed to his long time girlfriend, Nellie, he researched diamonds trying to determine the empirically perfect engagement ring to give her — finally settling on one that was 3.14 carats. Romance, Pi-style.

Levchin is also intensely competitive, intensely driven, and well, just generally intense — even by Valley standards. I’m not sure what he wears in between companies, because his wardrobe is only company T-shirts during the process. I never met anyone who lives, breathes, and wears each challenge in quite the same way. His second company Slide was born more out of a desire to build something bigger than PayPal than it was a passion for the product itself.

It showed. What started out as push media morphed into glitter slideshows for blinging out a MySpace page and then morphed again into the company that allowed you to throw sheep over Facebook in the early days of its platform. Slide continually evolved into whatever widget the early and evolving social Web could support — as Levchin assiduously minded the data and pruned the product to the demands of the teenaged girls who used them.

The way he built Slide was more emblematic of who Levchin is than the product itself ever was. It always seemed strange that someone so serious, cerebral, and intense brought us something so seemingly frivolous. But there was nothing frivolous about his approach to it. And while Slide was ultimately sold for far less than PayPal, less than its venture valuation, and the product was ultimately scrapped — it was still an acquisition valued in the hundreds of millions. That’s far more than almost all of the early widget and Facebook platform companies, more than most of them combined. It was a testament to his sheer force of will to make something that wasn’t that compelling into something a company like Google would actually value.

People would always question why I wrote so much about Slide in the early days, alongside LinkedIn, Facebook, Yelp, and Twitter. But it wasn’t Slide the product that impressed me, as much as Levchin the entrepreneur.

By contrast, with Glow, Levchin is making something he cares about, and perhaps that’s what’s surprising about it if you last saw Levchin during the PayPal or Slide days. His stage of life has changed a lot. This is what happens when Valley wunderkinds age — their sense of what the world needs does as well.

Not only does the app help women time the best moment to get pregnant and collect easy-to-enter data they can hand off to a fertility doctor, it also functions as an insurance substitute. (Although they can’t legally call it one.) As I understood it from the demo, hopeful parents pay $50 a month into a pool, and if they wind up needing treatments, that money helps cover it. Levchin has put a whopping $1 million of his own money into the pool to give people the convince that it’ll get to critical mass if they contribute.

It’s probably Levchin’s most heartfelt startup to date. PayPal — like Slide– morphed around until it found a reason to exist. In PayPal’s case that was largely facilitating eBay payments. Enabling the purchase of PEZ dispensers wasn’t anything Levchin was particularly passionate about. Like Slide, what mostly appealed to Levchin was the way he helped build PayPal. His epic race with fraudsters around the globe who wanted to kill the company and working with a team that included intellectual and strategic heavyweights like Peter Thiel, Reid Hoffman, David Sacks, Roelof Botha, and Elon Musk.

When he talks about Glow, it seems different. Sure, he leads with all the stats about what a big market healthcare is and suggests this is just the first of many similar apps that will bring big data and machine learning prowess to the healthcare industry.

But it’s also personal. Levchin has two kids, and while he says he and his wife didn’t have any fertility challenges, many of their friends have. He said on stage that he loves his kids so much, that he couldn’t live without them. They have changed how he sees the world. To see other people not be able to have that kind of love just felt wrong. So he’s using his particular talents, connections, and wealth to try to change that.

As someone who’s gone through a similar transformation in recent years, I was touched hearing this. Combined with his stoic Russian manner, Levchin can frequently appear robotic — a claim also levied at his long time friend and fellow PayPal co-founder Thiel. But he’s not a robot. He’s an incredibly sensitive, empathetic and loyal friend, albeit one with a taciturn interface. I always secretly wondered how having kids would change someone like Levchin. (Ditto, someone like Mark Zuckerberg.) He’s so intense about everything his life touches, it was impossible to imagine him as a passive, absentee dad.

It’s heartening that he’s channeled the overwhelming love for his children into something so positive. That alone makes me want Glow to succeed. But it also makes me hopefully that we’re on the cusp of a whole new kind of Internet company.

Levchin and I are the same age and moved to Silicon Valley around the same time — along with so many other Web entrepreneurs like the YouTube guys, Blogger, and Twitter co-founder Evan Williams, and many others whose names you know, whose names you’ve forgotten, and whose names you never heard to begin with.

It was just after the Netscape IPO, in the thrust of the dot com boom, and the world had never seen anything like it. The Valley had some 40 years of development under its belt by then, and plenty of storied companies and wealth had been created. But it hadn’t become the fodder for popular media until the consumer Web.

The Web made technology feel attainable for the masses for the first time, and with it, high growth entrepreneurship seemed attainable. The Valley was a magnet for a broad base of talent in a way it never had been before. People like Levchin are something akin to the “baby boomer” generation of the Valley — people who came here in the bubble, survived the bust, and took several years to come to grips with the carnage before believing in the Web and entrepreneurship again. Most of that generation were the architects of the social media wave — or at least the funders, mentors, and early believers in it.

While most of them crammed a lifetime of business successes and failures into less than 10 years, many didn’t start building a family and truly putting down social roots until just a few years ago. And because this generation was the first to build tech companies primarily inspired by their own everyday desires, I predicted a few years ago that we would see a flood of family-oriented startups.

We didn’t back when I predicted it. But it may be possible I was more early than wrong.

That’s what Nirav Tolia told me when we spoke about this recently at the headquarters of his newest startup, Nextdoor. Tolia is also part of this class and has recently had his first child. The experience has changed how he’s building his company compared to previous ventures and it’s influenced what he is building as well.

Nextdoor is a company that’s all about neighborhoods, communities, and families. When other people hit the point where they long for a friendly cul de sac where their kids can ride their bikes, they move to the suburbs. When a Web entrepreneur does, he builds a site to force the world to become that again.

Elsewhere in San Francisco, Web entrepreneurs and new parents like Twitter co-founder Biz Stone and Lightspeed’s Jeremy Liew have co-founded or joined boards of brand new schools, inspired by what they want for their kids. San Francisco was long known as a place families didn’t stay to raise their kids for a host of reasons. In another 10 years, this generation may change that.

Levchin’s explanation of why he’s starting Glow struck me much the same way. I am biased — clearly —  but I think this is the Valley’s “greatest generation,” since the Fairchildren. They were the first to mash up hard core technology with media and entertainment and a distribution engine that every person in the world could use. This generation of entrepreneurs had a relatively easy time raising money, and many made it quickly as well. They were the predecessor of the hacker ethos that now characterizes the Web and helped topple the sales ethos of the Valley’s earlier eras. They cheat and alter reality until it’s the way they want it.

Is it the first generation to discover with some surprise how rewarding children can be? No. But it is the first generation with this particular skill set, connections, wealth, and a mentality to just change reality if it doesn’t suit them or their changing stage of life. And that’s good for families — and those who’d like to have families — everywhere.

[Image via allthingsd.com]