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151 Fortune’s Jeff John Roberts on “Kings of Crypto” and the Rise of Coinbase

Jeff John Roberts
“Kings of Crypto” Author

Listen on Spotify, iTunes or…anywhere.

In 2013, Fortune’s Jeff Roberts visited “Satoshi Square” in New York.  It was the name of the location where a group of crypto anarchists and Wall Street traders bought and sold Bitcoin in the open air. Since that day, Jeff became fascinated with Bitcoin and new forms of money. That fascination led him to write the book “Kings of Crypto:  One Startup’s Quest to Take Cryptocurrency Out of Silicon Valley and Onto Wall Street”.

Said Fortune Senior Writer Robert Hackett, 

“Kings of Crypto tells the story of a ragtag band of rebels who saw the future of finance before anyone else and who wrenched the revolution into their orbit. Reading this book is like using a stethoscope to open the vault containing the cryptocurrency industry’s origins. Click, click, click—and a wealth of secrets spills out. Learn what made Coinbase, one of the most improbably successful Silicon Valley startups, hit it big—and what makes its founding ‘Vulcan Swiss bankers’ tick. As long as Satoshi Nakamoto’s identity remains secret, this is the closest you’ll come to understanding the rise of crypto—and where it’s all headed.”

In this episode, Jeff John Roberts discusses his fascination with cryptocurrency, the rise of Coinbase, and the potentially world altering-ascendance of Bitcoin.

Jeff John Roberts Website

Twitter  @jeffjohnroberts.

“Kings of Crypto”

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150 Hooman Radfar: The Rise of the ‘Business-of-One’

Hooman Radfar
Collective Founder

Listen on:

Hooman Radfar is co-founder and CEO of Collective, an online back-office platform designed for freelancers, consultants and other ‘businesses-of-one’. He is also a Venture Partner at Expa, a San Francisco-based start-up venture firm and studio where he was a founding partner (along with Uber Co-Founder Garrett Camp). Previously, he was co-founder and CEO of AddThis.  AddThis was acquired by Oracle in 2016.

Recently, Hooman took the somewhat rare step of leaving a perfectly good venture capital job to start a company. In this episode, he describes why the idea he is pursuing felt so compelling he had to make the move.  He also discusses his path to building and selling a company, as well as his immigrant parent’s path to the US.

On How Startups Emerge from their Initial State

There’s this murky period prior to figuring things out which people tend to write out of history. Where you’re kind of trying to find out what’s now called ‘product market fit’. Instagram went through it with Brbn, Twitter went through it with Odeo. You know, you get a group together, you create a chemistry, you start working on projects, and maybe that project works or it doesn’t work. But it takes that initial leap to get that precipitate and go.”

On the Time People Mocked Websites that Were “Collecting Eyeballs”

‘I think the way to express it in modern terms is that when you have a flywheel with effectively a cost of acquisition of zero, it’s uncommon. And I think now people realize how hard that is and how valuable it is because they know the distribution has value, that data has value. There are a LOT of monetization models:  premium, ad-supported, data-supported.” 

On Why He Started Collective

“There are ‘businesses-of-one”:  Freelancers, consultants and whatnot. It’s the largest set of entrepreneurs in the country. And ultimately, if you believe in the next ten years, it could be fifty percent of the workforce. Not just the largest set of entrepreneurs, but the largest part of the workforce. And that’s all I’ve been doing my whole career. And I said, wow, this is amazing. It looks like a straight line in hindsight.”

Hooman Radfar on Twitter


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149 Fabrice Grinda: Four Incredible Stories from the OLX and FJ Labs Co-Founder

Fabrice Grinda
FJ Labs

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

Fabrice Grinda is a wildly successful entrepreneur and investor.  In this episode he recounts in detail four stories that any entrepreneur – any person, really – will find fascinating.

The first is the story of building one of Europe’s first marketplaces before eBay got there – and what happens when you turn down $100 million for your company.

The second is the story of Zingy, and what it’s like to grind without capital and miss payroll 27 times, before ultimately succeeding.

Third, Fabrice talks about building OLX, the global trading platform, after Craig Newmark refused his offer to fix Craigslist.  Learn what happened when OLX and its competitor go to war and spend billions on – TV advertising.

Finally, Fabrice offers his considered view of the future:  On how climate change is being addressed through technology, and how COVID has affected startups that will ultimately change the world.

FJ Labs:

Fabrice Grinda

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148 Jaclyn Hester: Foundry Group’s New Partner!

Jaclyn Hester
Partner, Foundry Group

Jaclyn Hester has just become a Partner at Foundry Group.  So first, “Congratulations, Jaclyn”.

Listen on iTunes: Spotify or wherever you get your podcasts

Jaclyn joined Foundry Group – the Boulder-based tech company and venture fund investor — after a few years at big law firms.  As a lawyer, she worked on everything from startup formation and financing to large M&A processes. 

During graduate school at CU Boulder, she caught the entrepreneurship bug and immersed herself in the local startup community, serving as the Executive Director of Startup Colorado. She has also built a startup with her husband, Anders.   Their family’s bootstrapped tour and activity software company was successfully acquired in 2018 by She becomes a partner Foundry just as it raises its first Foundry Group Next (“FG Next”) fund.  

Episode Quotes:

On Her Path from Lawyer to Entrepreneur

“I always had a feeling that there was something more interesting about the businesses themselves than about the legal aspect. I think for me, it felt like being the attorney was just a way to be connected to the business. And I enjoyed going to law school. It was an incredible education.  But I must have known that I liked the businesses, maybe, better.“

On the Purpose of the FG Next Fund

“It is important to remember that the pools of capital at the institutional level — so the pension funds, the endowments — these are multi billions of dollars.  Venture capital is just a teeny tiny thumbnail inside of their private asset or private equity asset class, which itself is one a bunch of other asset classes that they invest in. And so it’s probably among the riskiest highest reward of the things that they invest in. But it’s a really small piece. So if you think about, a 10, 20, 30 billion dollar pool of capital spending time on making 1 to 10 million dollar investments in a venture capital fund — just doesn’t make sense.”

On COVID-19’s Impact on Companies

“We’ve always believed that you can build great, great companies anywhere and that the talent is not concentrated in the Bay Area. That trend is accelerating with more openness to remote work. Not having to have everyone in the same place means that people are thinking about talent differently.”

Foundry Group

Jaclyn on Twitter

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147 Sarah Leary: Nextdoor’s Co-founder Becomes a VC

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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:

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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

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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. “

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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

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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 

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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

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