PCH Driven: What Serial Entrepreneur and Angel Investor Spencer Rascoff Looks for in a Founder

Jamie Williams
­Jamie Williams is the host of the “PCH Driven” podcast, a show about Southern California entrepreneurs, innovators and its driven leaders on their road to success. The series celebrates and reveals the wonders of the human spirit and explores the motivations behind what drives us.
PCH Driven: What Serial Entrepreneur and Angel Investor Spencer Rascoff Looks for in a Founder

In this episode of the PCH Driven podcast, Spencer Rascoff shares what drives him as the co-founder and former CEO of Zillow; and co-founder of Hotwire, dot.LA, Recon and his VC firm 75 & Sunny.


Rascoff talks about the future of real estate, how having a diverse staff can help companies make smarter decisions, how he chooses which startups he invests in and offers advice on recruiting talent and building out teams for startups.

He also shares some candid feelings about how the tragic death of his brother when he was 15 changed how he viewed the world, and spurred his ambition and drive.

"I would need a psychiatrist to determine if it's because I was trying to achieve what he might have gone on to achieve, which he wasn't able to, or [whether] I was trying to make him proud," Rascoff says. "I have observed in myself that it was a motivator and continues to be."

That drive, in part, led Rascoff to Goldman Sachs and, from there, to TPG Capital, where he got the opportunity, at the age of 23, to run a discount travel startup alongside some of the firm's largest clients, many of which happened to be airliners. They called it Hotwire.

"And you know, I was far too young for that level of responsibility," Rascoff says. "I always like the quote, 'luck is what happens when preparation meets opportunity'. So yes, I was lucky to be there. But I was also prepared. And I found myself in a situation of opportunity and, and took a big risk by leaving the private equity firm to go do this startup."

Rascoff talks about what he looks for in entrepreneurs, especially young founders starting their first company. Beyond looking for good product people or technologists, Rascoff says he looks for proof of passion — along with some earlier success they've had.

"The best situation is if they've had a taste of success, but haven't knocked it out of the park yet," he says. "Someone with a chip on their shoulder, someone with something to prove."

Founders, he says, will need that drive if they're going to "jump through walls" they'll eventually face, and succeed. Beyond that, he's looking for ideas that go beyond successful companies -- ideas that can be scalable, if they're to receive funding.

"I, as an angel investor, have to believe that there's a potential multibillion-dollar exit," he says."There are some things that are good ideas, but they're just not fundable. But it doesn't mean that you shouldn't pursue it as an individual. And I think that a lot of founders don't understand that distinction."

Click the playhead to hear more of the conversation, and subscribe to PCH Driven on Apple, Stitcher, Spotify, iHeart, Google or wherever you get your podcasts.

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Energy Shares Gears Up To Bring Equity Crowdfunding to Retail Investors

David Shultz

David Shultz reports on clean technology and electric vehicles, among other industries, for dot.LA. His writing has appeared in The Atlantic, Outside, Nautilus and many other publications.

Energy Shares Gears Up To Bring Equity Crowdfunding to Retail Investors
Photo by Red Zeppelin on Unsplash

The Inflation Reduction Act contains almost $400 billion in funding for clean energy initiatives. There’s $250 billion for energy projects. $23 billion for transportation and EVs. $46 billion for environment. $21 billion for agriculture, and so on. With so much cash flowing into the sector, the possibilities for investment and growth are gigantic.

These investment opportunities, however, have typically been inaccessible for everyday retail investors until much later in a company’s development–after an IPO, usually. Meaning that the best returns are likely to be captured by banks and other institutions who have the capital and financing to invest large sums of money earlier in the process.

That’s where Pasadena-based Energy Shares comes in. The company wants to help democratize access to these investment opportunities and simultaneously give early-stage utility-scale energy projects another revenue stream.

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Why These Ukrainian Entrepreneurs Are Making LA Their Home

Aisha Counts
Aisha Counts is a business reporter covering the technology industry. She has written extensively about tech giants, emerging technologies, startups and venture capital. Before becoming a journalist she spent several years as a management consultant at Ernst & Young.
Why These Ukrainian Entrepreneurs Are Making LA Their Home
Joey Mota

Fleeing war and chasing new opportunities, more than a dozen Ukrainian entrepreneurs have landed in Los Angeles, finding an unexpected community in the city of dreams. These entrepreneurs have started companies that are collectively worth more than $300 million, in industries ranging from electric vehicle charging stations to audience monetization platforms to social networks.

Dot.LA spent an evening with this group of Ukrainian citizens, learning what it was like to build startups in Ukraine, to cope with the unimaginable fear of fleeing war, and to garner the resilience to rebuild.

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