Office Hours with Spencer Rascoff

Office Hours with Spencer Rascoff

Spencer Rascoff is a New York Times bestselling author who co-founded four tech companies, invested in over 50, and was CEO of Zillow for a decade. His first startup, Hotwire, sold to Expedia for $685 million, and his second startup, Zillow, is now a real estate colossus, worth around $10 billion dollars. Now, he’s cofounded dot.LA, a media company covering the cutting-edge LA tech scene. Hear Spencer discuss with other CEOs and business leaders – with a special focus on his hometown of Los Angeles -- how to manage, how to lead, and how to win in business.

Episodes

April 1, 2021

My friend, serial entrepreneur and legendary real estate coach, Tom Ferry, shares his career trajectory from sales to coaching phenom, the single biggest pitfall for work performance and his take on California’s business climate.

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Chris Webb rejected attending college in favor of diving into a finance career at eighteen years old. Now, he’s the CEO and co-founder of ChowNow, an app and online ordering system for restaurants that doesn't charge the onerous fees required of other delivery services. Hear Chris share how his education steeped in Wall Street and his mother’s surprise restaurant investment came together to ultimately inspire ChowNow.

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Shoeboxes full of invoices and receipts ignited the idea of Service Titan for Ara Mahdessian, the company’s CEO and cofounder. An Armenian immigrant from Iran, Ara came to the U.S. with his family as a young boy. He watched his parents assimilate to their new country while toiling into late hours of the night in order to give their family a good life. Their hard work paid off. Ara attended Stanford where he studied software enginee...

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Before PayPal, there was Bill Point, a company cofounded in the late 90s by Keith Richman, now cofounder of Boosted Commerce, which buys top-rated companies on Amazon and other e-commerce ecosystems and helps take them to their next level. Hear how the arc of his serial entrepreneurship follows the trajectory of the internet, what Boosted looks for in their acquisitions and what Boosted offers their companies to help them grow.

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As a self-taught teenage computer programmer in Brazil, Henrique Dubugras launched his first company, Pagar.me at age 16. After he sold it, Henrique was accepted and enrolled at Stanford, but dropped out early to follow his entrepreneurial instincts. This led him to co-found Brex with Pedro Franceschi, a business-to-business fintech unicorn disrupting the century old industry of banking small businesses.

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Birds were the first dwellers Austin Allison, CEO and co-founder of Pacaso, served with his boyhood bird-house business. Now, with Pacaso, the serial entrepreneur aims to democratize second home ownership by enabling people to co-own an amazing second home --- for 1/8 the cost. Hear his take on what it meant to have his first company acquired, his number one tip on how to keep his crew focused and how to best navigate what seems li...

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If there’s one thing to be learned from CEO and co-founder of Health-Ade, Daina Trout, it’s to pay attention to the opportunity in front of you and be prepared to pivot. Hear how Health-Ade Kombucha evolved from a hair-loss remedy to a huge brand of healthy drinks, learn about Daina and Spencer’s philosophy around hiring and gain insightful learnings around fundraising.

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Hear from GOAT cofounder and CEO Eddy Lu about big, public and most importantly, resolved founder fights, insight on when to know it’s time to pivot or quit, how GOAT differentiates itself from other sneaker e-commerce sites -- and one of GOAT’s early and clever growth hacks to convince consumers the company had more merch than they actually did.

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The burgeoning Los Angeles start-up and tech scene led to the founding of dot.LA one year ago. Today, we hear from its CEO and Spencer’s cofounder, Sam Adams, on how its mission both celebrates and holds accountable the burgeoning Los Angeles tech and start-up scene, how it’s baked DEI into its mission -- and why LA is the place for entrepreneurs to dig roots.

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Ynon Kreiz served on the board of Mattel before stepping in as CEO in 2018. Hear about how Mattel is leverage its massive brand portfolio across multiple platforms, from toys to films, how Mattel is working towards environmental sustainability and the priority Mattel places on DEI. Also, hear the answer to a burning UNO game question hotly debated in Spencer’s family.

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A free-flowing conversation packed with entrepreneurial lessons with serial entrepreneur, Beauty Counter founder, Gregg Renfrew. Hear what to look for in an investor, ideas about scaling, her passion for multi-channel business -- and why people should get rid of non-stick pans.

   
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Cameo’s highly-anticipated 2017 launch tanked. Its only talent was furious. But the startup persisted, and through grit has grown massively. Hear Steven Galanis, founder and CEO of Cameo, share the colorful story of the young company’s turnaround, how Galanis breaks down the best way to handle employee dysfunction and how he built up Cameo’s roster of tens of thousands of celebrities and influencers ready to send custom-crafted mes...

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Bill Gurley, Legendary Silicon Valley venture capitalist, is a general partner at Benchmark and famously known for investing early in trailblazing companies including Uber, GrubHub, my company, Zillow and so many others. Hear a conversation he and I had at the recent dot.LA Summit where we discuss marketplace-based companies, how work-from-home will accelerate business opportunity and why startups, though they might be attached to ...

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Huge musical success is not enough for the electronic musical group, The Chainsmokers, made of Alex Pall and Drew Taggart. As part of their hunger to grow and learn, they've started their VC firm, Mantis, where they focus on investing in Seed and Series A startups. Hear about how they see the similarities between building startups and making music, the value add they give to companies beyond their fame and reach, how they write...

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How tough is it to infuse a retail website with entirely new products every day? Very. Nonetheless, that’s what Zulily, an ecommerce site that sells unique retail brands primarily to women, did when it went live in 2010. Ultimately, Zulily sold for $2.4 billion in 2015. Hear Darrell Cavens, founder and former CEO of Zulily, Spencer and Harvard Professor Jeffrey Rayport discuss the why behind Zulily’s astonishing success and some gr...

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It’s not easy to turn around a company. But some executives seek out that challenge. An experienced turnaround expert, Brad Stewart is the relatively new CEO of Fair, an app to lease used, affordable cars for as long as desired. Brad started out in management consulting before becoming CEO of then-struggling XO Jet. After seven successful years at XO Jet, Brad now brings to Fair a wealth of experience. Hear his insight on the steps...

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Years of work experience, largely solving business problems for his family, gave Jiake Liu a fundamental understanding of how to run a successful business. It also fed his entrepreneurial thirst and ultimately led to his cofounding and leading Outer, an outdoor furniture and lifestyle company. Hear some hard-earned lessons from Jiake about startups, his Shark Tank pitch day experience and how he maintains investor relationships eve...

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Too many fashion options is a pain point Terry Boyle, cofounder and CEO of Behold, aims to solve with his newly launched retail platform. Hear how Terry, who’s been in fashion tech for over ten years with most of that time spent at the venerable Nordstroms, is competitively positioning and running his trailblazing company.

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Inspired in the midst of the MeToo awakening, Claire Schmidt founded All Voices. It’s a platform that allows employees to anonymously share feedback with company administration without fear of reprisal. Hear Schmidt, CEO, share the problems All Voices is trying to solve, how the communication process works -- and an early lesson learned that forced All Voices to quickly make a radical pivot. And yes, All Voices uses All Voices!

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On a mission to improve healthcare for every American, by offering steeply discounted prescription drugs, Doug Hirsch, cofounder and CEO of GoodRx, speaks with Spencer about how he built the business with a slow and steady attitude, how paranoia keeps him on his toes -- and why naivete is an entrepreneurial strength.

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