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Elad Gil: “A Startup is An Act of Desperation” and Other Wisdom from one of Silicon Valley’s Best Investors

Elad Gil

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It is not a stretch to call Elad Gil one of Silicon Valley’s best investors.  In a world where one big hit can make a venture capitalists’ career, Elad has invested in…Well, here’s a partial list Airbnb, Airtable, Anduril, Brex, Checkr, Coinbase, Deel, Figma, Flexport, Gitlab, Gusto, Instacart, Notion, Opendoor, PagerDuty, Pinterest, Retool, Rippling, Samsara, Square, Stripe, TripActions, Wish.

It seems almost impossible.  But there it is. 

Elad’s career includes working at Google, founding a company acquired by Twitter, and founding Color Genomics (you probably heard about them during the COVID response).

He is also author of the book High Growth Handbook: Scaling Startups from 10 to 10,000 People.

In this wide-ranging discussion, Elad shares his thoughts on everything from building companies to crypto, AI, and more.

Elad’s home page:

Elad on Twitter:

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Adrian Fenty: From Washington DC Mayor to…Venture Capitalist

Adrain Fenty
MaC Venture Capital

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There are a few – very few –non-traditional paths into venture capital.  Adrian Fenty may have one of the most unusual ones.  Adrian was the Mayor of Washington D.C., winning that post at the age of 35 (making him Washington D.C.’s youngest mayor ever).

In this episode we discuss his path to becoming mayor and his refreshing style for governing in that office.  But being mayor of a major US city was just the beginning.

Adrian became a special advisor to the venture firm Andreessen Horowitz, where he had the chance to observe its founders in action.

Today, Adrian is a Managing Director of the venture firm he founded, MaC Venture Capital.

MaC Venture Capital

Something Ventured

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Michelle Tandler: An Entrepreneur’s “Growth Path”, and “What’s the Matter with San Francisco?”

Michelle Tandler
Founder, Growth Path

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Michelle is an entrepreneur – founder of “Growth Path”, a provider of audio courses for professional development.  Her goal is to teach soft skills and management at scale.  She previously worked at tech firms Thumbtack and Yammer, as well as the venture capital firm Trinity.

In this episode we discuss her entrepreneurial journey,. She gives us a candid look at the highs and lows of being an entrepreneur.

Michelle has also become a (fairly popular) voice of reason concerning the state of affairs in San Francisco.  She regularly poses thoughtful questions about various policies. She sheds light on the byzantine corners of San Francisco politics.  Here, she shares her thoughts on a range of issues, providing pretty thoughtful solutions, and frank explanations of various head-spinning policies.

Michelle Tandler on Substack

Michelle Tandler on Twitter

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Max Chafkin on Peter Thiel: “The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power”

Max Chafkin
Author, “The Contrarian”

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Max Chafkin is the author of “The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power”.  Max is a technology reporter for Bloomberg Businessweek.  “The Contrarian” isn’t just about Thiel.  It’s about that, too, of course — from PayPal to his Facebook investment to his failed hedge fund, etc.  But it’s also about “Silicon Valley’s political coming-of-age”, as the New York Times describes it.

We discuss how Peter Thiel came to wealth, the many controversies surrounding him.  We also discuss the calculations that led him to back Donald Trump’s presidency, and ultimately take a role in Trump’s transition campaign.

Max Chafkin on Twitter

The Contrarian: Peter Thiel and Silicon Valley’s Pursuit of Power

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Howard Morgan: From Renaissance Technologies to First Round Capital, and Beyond

Howard Morgan
B Capital Group Chairman

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Howard Morgan is one of those few – very few – people who have built multiple game-changing firms.  He is co-founder of Renaissance Technologies (sometimes known as “RenTec”).  While a professor at the Wharton School of the University of Pennsylvania, he divined the opportunity to apply emerging computer technologies to investing.

The resulting firm – Renaissance Technologies — is one of the most famous, and successful, hedge funds.  It pioneered systematic trading using quantitative models derived from mathematical models.  It famously hires people who are incredibly smart – but don’t have previous investing experience.

While some might consider that enough of a career for one lifetime – Howard went on to co-found First Round Capital with Josh Koppelman.  First Round is one of the most respected seed venture capital firms, with investments in firms like Notion, Roblox, Uber, and Square.

At last Howard is ready to retire….wait no.  No, Howard is now the chairman of B Capital Group, the global investment firm founded by Eduardo Saverin.

In this episode we discuss how this remarkable journey unfolded, and what he sees for the future.

B Capital Group

Renaissance Technologies

First Round Capital

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Jenny Lefcourt: Freestyle Capital Partner’s Path from Entrepreneur to VC

Jenny Lefcourt of Freestyle Capital. from Barron’s “100 Women Shaping the World of Finance”

Jenny Lefcourt is a partner at Freestyle Capital, a seed stage venture firm overseeing $450 million in seed investments. Jenny dropped out of her Stanford MBA program – before that was cool — to co-found online wedding registry startup (with classmate, Jessica Herrin)

After The Knot acquired, Jenny started another company – Bella Pictures – also subsequently acquired.  Today she is a partner at Freestyle Capital, and was recently named one of Barron’s “100 Women Shaping the World of U.S. Finance”.

In this conversation we discuss her path through these entrepreneurial experiences to becoming a prominent Silicon Valley venture capitalist, and co-founder of All Raise. She shares what it’s like to join and then become partner of a venture firm that already has a couple high-profile partners; why she thinks entrepreneurs make great VCs, and the role of All Raise in Silicon Valley.

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Freestyle Capital

Something Ventured Podcast

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Joe Hudson: The Coach Behind Silicon Valley’s Unicorn CEOs

Joe Hudson

I talk to a lot of founders and CEOs in Silicon Valley.  They started telling me “you know, I couldn’t have done it without…” When I heard that multiple times, I just had to meet the guy they were talking about – Joe Hudson.

Turns out, Joe Hudson is a sought after executive coach and creator of The Art of Accomplishment, an online learning platform for personal development.  And get this – he quit his job as a venture capitalist to become a coach.

Yep — as a venture capitalist Joe found that the most rewarding aspect, and the part he was most successful at, was the mentorship and coaching of the leadership of his portfolio companies. This insight moved him to his present role as a coach, business consultant and teacher.  He now coaches 12 CEOs and leaders in prominent companies and runs transformative programs for both individuals and businesses. He is says he is practicing a craft that makes big, lasting, and overwhelmingly positive impacts on the lives of people in his programs and in the companies he works with.

In this episode we discuss his journey, why he only coaches 12 people a year – and how you can participate (since you’re not one of those 12 people!) (Hint:  Go to and use code “VENTURED”)

The Art of Accomplishment.

Something Ventured Podcast

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Eliot Brown on the Crazy Life and Wild Times of WeWork Founder Adam Neumann

Eliot Brown, along with Maureen Farrell, is author of “The Cult of We: WeWork, Adam Neumann, and the Great Startup Delusion”.  As a reporter for the Wall Street Journal he became intrigued by the messianic founder who had raised billions of dollars, and developed a cult-like following at his startup WeWork.

“In little more than a decade, Neumann transformed himself from a struggling baby clothes salesman into the charismatic, hard-partying CEO of a company worth $47 billion – on paper. With his long hair and feel-good mantras, the six-foot-five Israeli transplant looked the part of a messianic truth teller. Investors swooned, and billions poured in.

Soon, however, WeWork was burning through cash faster than Neumann could bring it in. From his private jet, sometimes clouded with marijuana smoke, he scoured the globe for more capital. Then, as WeWork readied a Hail Mary IPO, it all fell apart. Nearly $40 billion of value vaporized in one of corporate America’s most spectacular meltdowns.”

In this episode Eliot Brown shares what he learned studying WeWork and it’s larger-than-life founder.

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Brad Feld: “Friedrich Nietzsche is the Patron Philosopher of Today’s Entrepreneurs”

Brad Feld’s latest book (with David Jilk) is “Entrepreneur’s Weekly Nietzsche (A Book for Disruptors)”. Those familiar with Brad’s “Feld Thoughts” blog, will find the unexpected title – unsurprising.

While reading Nietzsche (um, yes) Brad noted that his favorite personality was a “free spirit: An obsessed individual with a vision of the future and the will to make it so, a rebel who creates the future with childlike enthusiasm.”  That, thought Brad, sounded a lot like…an entrepreneur.

The book is “a modern Art of War, connecting the dots to our high-tech business environment”.

Each short chapter takes a quote from Nietzsche and applies it to an area of entrepreneurship.

Brad Feld has been a famous venture capitalist for a long time.  He has been an early stage investor and entrepreneur since 1987. He currently runs Foundry group, which he co-founded. Before that Brad co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars.

Brad is a writer and speaker on the topics of venture capital investing and entrepreneurship. He’s written a number of books as part of the Startup Revolution series and writes the blogs “Feld Thoughts” and “Venture Deals”.

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Auren Hoffman — Silicon Valley’s Hyper-connected Founder, CEO and Investor Shares his Wisdom

Auren Hoffman

Auren Hoffman is one of the most connected people in Silicon Valley.  In a place where the currency of the land is connections – Auren is near the top of the heap.

Auren is a Founder and CEO — He founded SafeGraph in 2016, and previously founded LiveRamp, which is now public (NYSE: RAMP) – a leading data platform.

Auren is also an investor – he has invested in more than 120 active technology companies.

Auren went to UC Berkeley a B.S.E. in Industrial Engineering and Operations Research from UC Berkeley.

But perhaps most importantly – Auren shares his wisdom:  Often in napkin sketches, shared on Twitter.  In this podcast we discuss Auren’s journey, his wisdom and his view from his unique perch in Silicon Valley.

Safegraph’s podcast: “World of DaaS” | Safegraph | Auren on Twitter

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