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Something Ventured Posts

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

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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

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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

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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:


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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

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136 Codepath’s Michael Ellison: How Black CS Students View Silicon Valley / The Daily Reality For a Black Man in San Francisco

Michael Ellison

“Most Black computer science students think Silicon Valley companies are racist.”  If you didn’t know this already – you should really sit down and listen to this episode.

No one educates more Black students in computer science than Codepath.  Codepath is the non-profit co-founded by Michael Ellison to eliminate educational inequity in technical careers.  Every year Codepath teaches hundreds of college students the skills they need to get jobs at companies like Facebook, Google and Amazon.

In this episode, Michael shares his stark assessment of how Silicon Valley treats Black engineers, including CS students who may have not gone to a ‘top’ school.  He discusses the toll both Covid and the recent events like the George Floyd killing have taken on Black students.

Michael shares what Silicon Valley leaders – venture capitalists and companies alike – can do to empower Black engineering students who seek jobs, or seek to start companies in Silicon Valley.

Listen on iTunes, Spotify or wherever you get podcasts.

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135 VC Monique Woodard — Monique is NOT “Doing Fine”

Monique Woodard

Monique Woodard is a venture capitalist in Silicon Valley.  She is one of the very rare Black, female General Partners in venture capital.  Previously on Something Ventured we explored Monique’s unique path to becoming a venture capitalist, and what she invests in.

As events drove the Black Lives Matter (“BLM”) movement to accelerate worldwide, Monique was gracious enough to come back and share her thoughts.

She discusses what she believes is the state of the BLM movement in general, and Silicon Valley’s dismal record on supporting Black investors and entrepreneurs in particular. She offers pure, unvarnished advice about what Silicon Valley can do – actually do – to begin fixing its problem.

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

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134 IVP’s Somesh Dash: In Divisive Times, Is Silicon Valley Doing Enough?

Somesh Dash

Hold fast to dreams

For if dreams die

Life is a broken-winged bird

That cannot fly.

Not every podcast includes a Langston Hughes quote.  Not every venture capitalist is Somesh Dash.  Somesh is a partner at the venture capital firm IVP.  IVP is one of the largest, most established venture firms in Silicon Valley.  From his post there, Somesh has seen several cycles of Silicon Valley’s ups and downs.

In this episode, we contemplate recent events:  Racial issues converging with US 2020 presidential politics and a country on edge from Covid. Looking to the leadership of Ailene Lee and All Rise, we contemplate what more Silicon Valley might do to be supportive of black Americans.  Not just the few (too few) black VCs and Founders in Silicon Valley, but All black Americans.

We turn to the long arc of investing in Silicon Valley – from the early days of IVP, the dot com crash, the 2008 financial crisis, the last 10 years and – the great unknown that is next.  

We finish with how VCs have reacted to Covid, and what is REALLY going to happen with ‘working from home”. Finally – we end on a positive note, with the poem that begins this introduction.

On iTunes, Spotify or anywhere you get your podcasts.


Somesh Dash on Twitter

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133 Eric Tarczynski of Contrary Capital: College – The Definitive Episode on Investing in Startup Founders in College

Eric Tarczynski of Contrary Capital

(Note:  This episode was recorded before the Covid crisis. It includes a brief introduction with Eric Tarczynski to update the status of his fund and college investing, post Covid.)

Eric Tarczynski is the founder of Contrary, a venture capital firm focused on investing in college students starting companies.  In this episode, Eric discusses how he built a network of college entrepreneurs, and how he created a venture fund focused on investing in college students.  We discuss the unique benefits and risks of investing in young founders, many with no work experience, as well as the lessons from famous college founder – Mark Zuckerberg.  

Colleges Contrary includes in its network are:  Boston College, Boston University, BYU, Brown, Carnegie Mellon, Columbia, Cornell, Dartmouth, Duke, Emory, Georgia Tech, Harvard, NYU, Northeastern, Ohio State, Penn State, Princeton, Rice, Stanford, Texas A&M, Tufts, Berkeley, UCLA, UCSD, University of Chicago, UC Boulder, University of Illinois, University of Maryland, University of MIchigan, Notre Dame, Penn, USC, University of Texas, Virginia, Vanderbilt, University of Washington, Yale, and Waterloo.

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

Contrary Capital:

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132 Lyft’s Raj Kapoor: World Without Covid

Raj Kapoor
Lyft Chief Strategy Officer

Raj Kapoor contracted Covid in mid-March.  He and his family are recovered and well. But Raj is taking aim at shortening the path to a post-Covid world.  He partnered with Clara Health to create  The site let’s people register to help researchers worldwide accelerate their race to find better testing, treatments, and vaccines.

Raj has been a venture capitalist (Mayfield) and a entrepreneur (SnapFish).  He is currently the Chief Strategy Officer at Lyft.  

In this episode we discuss Raj’s journey from contracting to recovering from Covid.  We also discuss the path to finding a treatment, and the why’s and how’s of California’s lockdown.  We also discuss (Caifornia Governor) Gavin Newsom’s “6 Criteria for lifting quarantine”, and the current state of the US Presidential race.

We turn to Lyft, and the future of transportation (the original topic of this episode):   How Lyft is faring during the Covid crisis, how will change cities, and how Lyft affect climate change.

Finally, we briefly discuss the effect Covid might ultimately have on the music industry.

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

World Without Covid


Clara Health

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