Something Ventured -- Silicon Valley Podcast

There are only so many iconic social networks in the world – and Nextdoor is one of them.  While perhaps not as fast-growing as Facebook or even LinkedIn, Nextdoor has steadily become the hub for neighborhoods around the world.

Sarah Leary founded Nextdoor, along with Nirav Tolia, Prakash Janakiraman, and David Wiesen.

In this episode, Sarah tells the story of getting Nextdoor off the ground.  She talks about the painstaking work they did to figure out how to build a healthy community around a neighborhood, before they were ready to scale.

We talk about the impact COVID-19 had on Nextdoor communities, and how and why she decided to become a venture capitalist at Unusual Ventures.

Notable Episode Quotes

On Starting Her Career at Microsoft

“I joined Microsoft at really a golden time:  The early 90s.  I was on the product team that launched the first version of Microsoft Office, and that was an all-star team. It was a time when Microsoft was just taking off and went from being this software company that some people had heard of to a household name. I was fortunate enough to, for example, be on stage where we launched Office ninety five with Bill Gates and Jay Leno.  We were writing the script as we went along and that was an amazing learning curve.”

On the “Pivot” from Fanbase to Nextdoor

“If you don't get the seeds of a community right in the beginning, it becomes very difficult to fix it. And after about six months, we actually offered to give the money back to Bill Gurley, who was the lead investor in Fanbase. He said, ‘That's the easy way out. I'll give you three months to work on some new ideas. It doesn't have to be directly related to Fanbase. But why don't you guys take another crack at it?’ That was hard. It was very hard to step back and say.  ‘This isn't working and confess to each other that we didn't think it was going to be the next ESPN’, but I'm so glad that we did.”


On the Earliest Days of Nextdoor

“The idea of Nextdoor changed pretty dramatically in those early stages before we ever wrote a line of code. And thankfully, it's probably saved us from years of going down the wrong path and frankly, probably losing faith in what it was that we were trying to. The prototype was actually launched in the Bay Area and with one neighborhood in Menlo Park, and it worked. People wanted to talk to their neighbors, but we were very cautious and said, OK, that's not enough. Let's try some other ones. In Seattle, Washington, we had one in upstate rural New York. We had one outside of Washington, D.C., and one in Tennessee. And we just started to see how people were using the platform. And that gave us the confidence after we did about five of those to say, ‘OK, this is the winning idea and we're going to double down on it’.”


Unusual Ventures:

Something Ventured:


Direct download: 147_Sarah_Leary_of_Nextdoor.m4a
Category:general -- posted at: 7:28pm EDT

Trae Vassallo is co-founder and partner at Defy, a venture capital firm she built with Neil Sequeira.  She was previously a general partner at Kleiner Perkins.

Trae made her way to Silicon Valley from…rural Minnesota.  As a girl, Trae fell in love with coding – on an Apple II.  She went, sight unseen, to Stanford University, where she studied mechanical and electrical engineering.  After a stint at design firm IDEO, she co-founded and led product at Good Technologies.

In this episode we discuss Trae’s path to Kleiner Perkins, and her experiences being one of relatively few female venture capital partners in Silicon Valley. She contrasts the treatment of women in Silicon Valley before, and after, Ellen Pao’s lawsuit (Check out Episode 101).  We discuss why she struck out on her own rather than staying at Kleiner, and how she and her partner came together to form Defy.

Finally, Trae discusses a health scare that led to her discovery of integrative medicine and lifelong quest for healthy living.


On Her Early Experience with Computers

“It was like third or fourth grade where I have vivid recollections of seeing Oregon Trail (a video game), playing that game, and then learning how to build simple graphics programs. And that really was a spark for me:  That, you can logically build a sequence of steps and then have it go execute. And that kind of problem solving to me was incredibly exciting. And so that was the spark that made me realize I'm a problem solver, I'm a creative.”

On Palm Pilot and Women Leaders

“I was fortunate to get on the engineering team that worked on the Palm V. And through that, I got to work with Donna Dubinsky (Palm’s CEO) and Jeff Hawkins (Palm’s Founder). And this was when they were justgetting started and they had this runaway kind of success. That was my first exposure to a startup into what it meant to be an entrepreneur and frankly, a female CEO, a woman CEO who is just amazing at her job. And so I thought, OK, I love this engineering thing, but I want to do what she's doing.”


On Integrative Medicine

“When I left Kleiner, one of my top goals was” I'm going to get my health back.  I want to feel better than ever. I started reading up and looking at less conventional options, because I literally had been to Mayo and Cedars and Stanford and UCSF and nothing. Nothing, nothing. And I finally found this whole world of integrative medicine, which I'm now a huge fan of. The thesis behind it is really about root cause analysis instead of giving you a drug to alleviate the symptom of that issue.  Rathere, we're going to figure out why you have that issue to begin with and get to the root cause and solve that problem so we don't have to cover up your symptom.”


Something Ventured:

Direct download: 146_Trae_Vassallo.m4a
Category:general -- posted at: 8:06pm EDT

William Davidow is a Silicon Valley pioneer, former Intel VP, and renowned venture capitalist.  He is author of the new book, with tech journalist Michael Malone, THE AUTONOMOUS REVOLUTION: Reclaiming the Future We’ve Sold to Machines (Berrett-Koehler, February 18, 2020).  It’s a provocative look at how to safeguard humanity from our autonomous future and how to harness its benefits.

According to Davidow and Malone, for the third time in the history of humanity civilization is undergoing phase change.  The first was the Agricultural Revolution, the second the Industrial Revolution, and we are now in the midst of the Autonomous Revolution.

Some ideas discussed:

  • How to adapt society to our new era and transform our relationship with intelligent machines the authors propose in the new book

  • Creating tiered personal information “safety deposit boxes” over which users would have complete control to protect internet privacy;
  • Imposing a tax on sending emails, time spent on social networks, and gaming;
  • Programs that automatically block phone use while we’re driving;
  • Regulation that puts limits on Artificial Intelligence;
  • Proactive investment in the infrastructure of the future to offset inevitable job loss.


More on William Davidow: 

William Davidow is a Silicon Valley pioneer who ran the microprocessor division at Intel at the dawn of the chip revolution and was later senior vice president of marketing and sales. Prior to Intel Corp., Bill worked in various managerial positions at Hewlett Packard and General Electric. He cofounded Mohr Davidow Ventures, one of the Valley's premier venture capital firms, in 1985. Bill serves on the boards of California Institute of Technology and the Stanford Institute for Economic Policy. He is the author of three books and the coauthor of two, including The Virtual Corporation, which sold more than 100,000 copies.


Episode Exerpts:

On the Evolution of Technology Innovation

“When I was at Intel, you know, we used to get up and feel like we were putting on our Superman shirts and going out and changing the world. And what we were doing was automating existing processes: In other words, we made a stoplight run better or we made a typewriter into a word processor.

But if you looked at it, there was still a factory or there was still a stoplight. We didn't change the structure of things. And what is different today is that our technologies are changing the social and economic structure of things.”

The Problem of Virtual Worlds like Facebook

“We have real problem that people are choosing to live in a virtual world. It turns out that you evolved in a physical world, YOU controlled the physical world. A tree was not created to be firewood. You managed the world and made the tree firewood.   The physical world had no purpose and you were running the physical world. But when you go to a virtual world, a virtual world DOES have a purpose. And the purpose of the virtual world is to control your behavior. you you're down to two senses, both of which are impaired. “

On the Accelerating Pace of Job Destruction

We keep finding new work for people to do, so we keep creating opportunities, I think today the challenge is that we may not be able to create the opportunities fast enough. I mean, these technologies have such broad impact. Netflix put Blockbuster Video out of business, when Blockbuster Video had nine thousand stores and 60,000 employees. And Netflix, I think, had one thousand employees. And those are the kinds of things will continue to happen. It’s going to turn everything upside down. I believe in a free market, but free markets have their flaws. They do not allocate wealth based on social contribution, they allocate wealth based on your ability to make money. In the future we may be living in a society where we're going to have to find ways to compensate people based on their social contribution as opposed to whether they're just a great high speed trader. “

Kent Lindstrom (host):

William Davidow:        

Something Ventured: 

Direct download: 145_William_Davidow.m4a
Category:general -- posted at: 7:51pm EDT

Rob Chesnut is an advisor to Airbnb, where he was previously Chief Ethics Officer and general counsel.  His recently released book is Intentional Integrity: How Smart Companies Can Lead An Ethical Revolution.

Rob started his career as a federal prosecutor, but decided he could do more good in the world by working for companies like eBay and Chegg.

Eventually joining Airbnb, he helped Brian Chesky navigate issues such as racial discrimination by Airbnb hosts.  He also helped Airbnb create a culture of “Intentional Integrity”.

In this episode we discuss Rob’s journey to and through Silicon Valley, and his experience creating ethical cultures those companies.  We also discuss what happened to Airbnb when the COVID crisis hit.

Hear what Brian Chesky said as Airbnb was faced with lawsuits over discrimination by its hosts

Rob Chesnut Episode Excerpts

On leaving the role of federal prosecutor to work for tech companies:

“After a while, it's a real negative. It has a negative aspect to it.  You're putting young people in jail for long periods of time, and you feel like you're not contributing in a positive, proactive way to society.”

 “On the Future of Travel”

“I don't think that the pandemic is going to push people to stay in their homes forever. I think that people are going to travel. But what I think we're going to see is that there's a maybe a different type of travel. One thing that there's a trend, I think, that may come out of the pandemic, which is really going to help Airbnb and that is ‘work anywhere’. So if you can work and do your job from literally anywhere that has Internet access, that suddenly frees you to go places and do things 52 weeks a year that you might otherwise have only been able to do three weeks a year.”


On Intentional Integrity

“I think that integrity is a word that people are often uncomfortable talking about because it gets to people's morals, their purpose, maybe even their religion. And so leaders are uncomfortable talking about it and what they do is outsource it to lawyers and it becomes compliance. There's a difference, though, between compliance and integrity. So the point of the title is we have to get over the discomfort, we have to have the conversation. And if we want integrity to be part of our company, we can't just assume that it's going to happen, that we're just going to hire good people and that it's going to happen. We have to make an intentional effort to weave it into our culture. And so the point of that title, is a call for getting through that discomfort and taking affirmative steps to make it part of what you do in business.”


Intentional Integrity


Rob Chesnut


Something Ventured


Direct download: 144_Rob_Chestnut_of_AirBnB.m4a
Category:general -- posted at: 6:51pm EDT