Press "Enter" to skip to content

Something Ventured Posts

146 Trae Vassallo: Defying Gravity in Silicon Valley

Trae Vassallo of Deefy
Photo by Chris Michel

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.  Rather, 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.”

Listen on Spotify, iTunes, Amazon, etc.


Trae Vassallo on Twitter: @trae

Comments closed

145 William Davidow: “Civilization is Facing Its Third Phase Change”

Bill Davidow of Mohr Davidow

Listen on Spotify, iTunes or wherever you find podcasts.

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).  It’s a provocative look at how to safeguard humanity from our autonomous future and how to harness its benefits.

Some ideas discussed

  • 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.

Davidow, having worked in the high tech sector even before there was a Silicon Valley, and Malone provoke a much-needed discussion about how we can navigate the autonomous revolution.


On the Evolution of Technology Innovation

“When I was at Intel, 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. “

Comments closed

144 Rob Chesnut: Airbnb’s Former Chief Ethics Officer on Intentional Integrity

Rob Chestnut

Listen on iTunes, Spotify or wherever you get your podcasts.

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.

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

Comments closed

143 Deena Shakir of Lux Capital on her Amazing Journey; The Post-COVID Future

Deena Shakir
Lux Capital

Deena Shakir is a partner at Lux Capital, a venture capital firm that manages more than $2 billion.  She is particularly interested in entrepreneurs building breakthrough companies enabling human and environmental health, access, and productivity.

While her immediate background before joining Lux sounds familiar – she was a partner at GV (previously “Google Ventures”) – her path before that is a bit more unusual.  As a journalist, Deena once hosted the pilot episode of a bilingual Arabic-English TV news series modeled after 60 Minutes.  

Deena was also a Presidential Management Fellow at the U.S. Department of State under Secretary Clinton, where she helped launch President Obama’s first Global Entrepreneurship Summit in 2010. 

She is the first-generation daughter of immigrants from Iraq and speaks fluent Arabic and French.

In this episode, we discuss a range of topics, from her experiences as an Arab-American to her path from Washington to Silicon Valley.  We also discuss the impact COVID is having on the venture business, and families like hers.  Also covered:  The unique craziness of online parenting groups.


On Education

“Education, is an area I’m passionate about, where I’ve made investments like that in a company called Mos. Mos is using artificial intelligence to make the process of searching for financial aid easier. Clearly, there were already platforms for you to search for scholarships. However, they’ve made that much more sophisticated, and the process is so much easier now. And this was meaningful for me personally because that was a process I went through. I paid for college by myself, patching together all these scholarships. And now that is something that is changing the lives of students on a daily basis.”

On Women in Venture Capital

“ In terms of women in venture, I think we’ve obviously we’ve come a long way, particularly in the last three years. I joined the venture world maybe three months before that moment, if you want to call it that, where everybody realized this was an actual problem.  It was in the summer, I think, of 2017 when a lot of this came to light. I think we still have a very long way to go. Some of the solutions may have potentially created additional problems around tokenism, for example, around cliques around  certain folks or groups taking up all the oxygen in the room, et cetera. But that being said, I’ve seen some really great progress.” 

On Software

“When it comes to software specifically, the democratizing piece of it is what gets me really excited. I get really excited about technology that streamlines analog industries — that allows people to do things more quickly — whether that means grassroots organizing or whether it means accounting.”

On the Impact of the 9/11 Attacks

“Being in high school, a teenager, during 9/11 — being a Muslim and Iraqi American, that was a really pivotal moment for me. It was the first time where I felt like these two parts of my identity that really always felt like they were fluid and just part of who I am — all of a sudden it seems like they weren’t to some people.  That really was troubling for me.” 



Lux Capital                   

Something Ventured 

Comments closed

142: Wag! CEO Garrett Smallwood on Pets in a Time of COVID-19

Garrett Smallwood

Garrett Smallwood was recently promoted to CEO of Wag Labs, the popular on-demand dog-walking service backed by venture firms from Freestyle Capital to Softbank.

New York Times said about the company “”Most dog owners should consider installing Wag on their phones just to have as a backup option. It is the best-designed and most efficient app for summoning a dog walker with some or no advance notice.”

Garrett previously founded Finrise, a startup that Wag acquired.

In this episode, find out what happened to the market for walking dogs and checking in on pets during COVID-19.  It’s not as obvious as you might think.

We also discuss what happened to Wag’s employees — and how they responded  — when COVID forced them out of the office.  

Finally, we answer the questions – is there a market for cat walking?

Listen on iTunes, Spotify or wherever you get your podcasts!

Wag’s investors also include:

  • Tuesday Capital 
  • Structure Capital 
  • Social Leverage 
  • Slow Ventures
  • RRE Ventures
  • Ludlow Ventures
  • Haystack
  • Greylock
  • General Catalyst
  • Sherpa Capital

Comments closed

141 Domm Holland: The Fast CEO on Guiding a Rocket Ship Through a Pandemic

Domm Hollad
Co-Founder and CEO of has raised over $20 million from firms like Kleiner, Index and Stripe.  It bills itself as the world’s fastest checkout – one click, no passwords.  A fascinating but typical story, such as it is, in Silicon Valley.

But then there’s this: Domm didn’t go to Stanford.  He isn’t even from the US. He’s from Australia, where his first business was…a towing company.  A more than $50 million business.

His co-founder is a woman.  He met her on Twitter.

So in this episode – find out how Domm made his way from Australia to Silicon Valley, and how he used his status as a Twitter power user to build his business.  Also learn what it’s like when your rocket ship startup is hit by a global pandemic.

Listen on iTunes, Spotify or wherever you get your podcasts!


Something Ventured

Comments closed

140 Brad Feld: Thoughts on Startup Communities in a Post-COVID-19 World

What makes communities of startups thrive, and how have they been impacted by the recession, COVID-19, and the remote work trend?

Brad Feld
Foundry Group

Brad Feld addresses these questions in this episode and in his new book “THE STARTUP COMMUNITY WAY: Evolving an Entrepreneurial Ecosystem” and the second edition of his book “STARTUP COMMUNITIES: Building an Entrepreneurial Ecosystem in Your City.”

You may know Brad as the legendary investor who co-founded the Foundry Group, and who has been an early stage investor and entrepreneur since 1987. Brad previously co-founded Techstars, and was an early investor in Harmonix, Zynga, MakerBot, and Fitbit. He writes the widely followed Feld Thoughts and Venture Deals. He currently is chair of the National Center for Women & Information Technology and on the boards of Path Forward, the Kauffman Fellows, and Defy Ventures. 


On the Chemistry of Silicon Valley

“Today’s Silicon Valley, if it started from scratch, could not create Silicon Valley.”

 On Initial Conditions of Startup Communities

“The punch line of that is that you don’t have a deterministic outcome. When you have a child, raising a child is a complex system. You can’t say that when the child is twenty-four years old, these are the things that child will be doing and will have done and how they will be living. All of the interaction effects over time in the moment affect what happens in the evolution of that child. Same thing with the startup community.”

On Racism in Startups and Venture Firms

“There is no question that empirically the number of non-white, black and brown voices and black and brown founders’ is a very low single digit percentage of the (startup and venture) population. And if you add in women into that mix and say black or brown women, that’s an even smaller percentage of the population. And so then the question is in now, what do you do? Its a complex system so you can’t just say, ‘OK, here are the new rules and this is what’s going to happen’.   Rather you’ve got to have participation of ALL of the different actors that have influence and ability in order to change things.”

On the Effect of COVID-19 on the Importance of Place for Startups

“Startup communities are complex systems that go through phase changes. In February, if you had said to anyone: “In three months, ninety nine percent of office workers around the world will be working from their houses.” That person would have said, you’re crazy, that’ll never happen. It can’t happen. The technology won’t support it. People won’t tolerate it. Not possible. But lo and behold, that’s what happened. And it works OK. We understand that place still has a lot of importance, especially around startup communities. However, the notion of connecting places together and building things that have a virtual component or that have a bigger geographic spread is also important.”

Listen on iTunes, Spotify or wherever you get podcasts.

Foundry Group

Feld Thoughts

Comments closed

139 Parker Conrad: Rippling’s CEO on His Entrepreneurial Journey

Parker Conrad
Rippling CEO

Parker Conrad lists himself as “customer support” at Rippling, but he is its co-founder and CEO.  He previously founded Zenefits.  In this episode he traces his journey from a journalist at Harvard, to founder and CEO of a company that has raised over $50 million.

Episode Highlights:

The specific thing he likes about sales
“I really liked sales. I enjoyed it. But I liked it in a very specific way:  I enjoyed selling something that I had built. I didn’t want anyone else explaining why it was great or what was so awesome about it, because they were going to screw it up somehow. They were not going to get it right when they were talking to people and telling them what’s great about this. I wanted to build the thing that I was selling.”

His fundraising ‘trick’
“Just find a way to be the Twitter guys (a fast growing company at the time which VCs were throwing money at) That was really the answer. And I think that that’s actually the right answer for most entrepreneurs.  Most of the “tactics” around fundraising don’t really matter. They’re such a rounding error. The important thing is to build a business that’s so compelling that they can’t afford to ignore you. And then all the other rules go out the window. And then it’s like very easy to raise. And if you can’t build something that is that compelling, then God help you.”

Why he’s motivated to build an HR management company
“I am an unusually resentful of the sort of busy work, administrative work. It’s why I was so resentful of having to of fax in insurance applications at my first company. If you can connect all of those underlying system and you can automate that and make it really seamless, that all disappears. And so in this sort of perverse way I really get excited about stomping that out for customers, because I’m the primary user of our product.”.


Listen on iTunes, Spotify or wherever you get your podcasts

Comments closed

138 Scott Simpson: From Amazon to Apple to Comedy, a Comedian’s take on the Future of Comedy

Scott Siimpson
Cheaper Than Therapy

Scott Simpson worked on digital books at Amazon, then podcasting at Apple.  Thus, a key guy on two technologies that revolutionized the “long tail” of content.  And then…he left to start a standup comedy show.  “Cheaper Than Therapy”,  housed in San Francisco’s Shelton Theater, presents about 6 standup comedy shows a week, almost always sold out.  

Then Covid hit Cheaper Than Therapy and standup comedy everywhere.  In this episode we discuss Scott’s path from tech to comedy, and the affects of Covid on the future of comedy.  We discuss how well jerry-rigged alternatives to standup comedy are working, as well as the dire state of performance businesses in general.

Listen on iTunes, Spotify or wherever you get podcasts.

Scott’s podcast:  California King

Cheaper Than Therapy

Scott on Twitter:


Comments closed

137 Promise Phelon: A Growth Warrior’s Trajectory from BEA to CEO to Venture Capitalist

Promise Phelon
Growth Warrior Capital

“As an entrepreneur, tech CEO and venture capitalist who is also a woman of color, I am well aware of the challenges most entrepreneurs face when it comes to raising capital.”  

So Promise Phelon summarizes with typical grace what she has learned in an amazing career.  Her book, “The Way of the Growth Warrior” – well you can’t get it yet.  You can pre-order it in the link below.  In the meantime, you can hear her story in this episode.

Promise Phelon started that career at BEA Systems, where she became Head of Product Marketing.  While a Black woman running marketing at BEA in the 1990s might be its own story, it was just her beginning.

Listen on iTunes, Spotify or wherever you get your podcasts.

The Growth Warrior

Something Ventured

Comments closed