S7E1: Spencer Rascoff, Co-Founder of Zillow, Gives Advice for Entrepreneurs Amidst a Macroeconomic Downturn

Episode 1 October 04, 2022 00:36:40
S7E1: Spencer Rascoff, Co-Founder of Zillow, Gives Advice for Entrepreneurs Amidst a Macroeconomic Downturn
The Room Podcast
S7E1: Spencer Rascoff, Co-Founder of Zillow, Gives Advice for Entrepreneurs Amidst a Macroeconomic Downturn

Show Notes

Welcome back to The Room Podcast. We kick off Season 7 with Spencer Rascoff, co-founder and previous CEO of Zillow. Spencer walks us through how he and the team came up with the idea for Zillow and the unforgettable “Zestimate” feature. Prior to Zillow, Spencer had been the founder of Hotwire, which sold to Expedia for $685 million. Currently, Spencer is an active angel investor in more than 100 companies and is incubating several more through his startup studio and venture capital firm, 75 & Sunny. He serves as executive chair of dot.LA, a news site covering the Los Angeles tech scene and he is co-founder and board chair of Pacaso, the company pioneering a new way to own a second home.

In our conversation today, we explore insights and themes such as the art of a killer feature, like the Zestimate, managing team morale and execution amidst a macroeconomic downturn, and why the future of real estate is fractional. 

For The Room Podcast in your inbox every week, subscribe to our newsletter.

5:05 - Where did Spencer grow up and how did that change his view of the world?
6:33 - Did Spencer always want to be a founder?
7:38 - What was the public opinion of the internet when Spencer was at Harvard?
11:23 - What did Spencer learn about being an entrepreneur from his experience at Harvard?
13:23 - What was the aha moment that sparked the launch of Zillow?
15:51 - How did Spencer and the team hone in on the specific product feature for Zillow?
19:04 - Did Big Data play any role in the start of Zillow? What was the data stack at the time?
21:15 - Who was the first external investor to say yes to investing in Zillow?
21:53 - What is the best case board dynamic?
26:04 - How did Spencer balance internal and external stakeholder management through his founding journey?
29:52 - What advice would Spencer give to entrepreneurs navigating “the early stages of our recession?”
31:49 - What is Spencer hoping to accomplish with Pacaso and “fractional ownership” of property?
34:08 - What is the user journey of purchasing a Pacaso home?
35:09 - What is one sector that Spencer believes is undervalued at the moment?
35:33 - Who is a woman that has had a profound impact on Spencer and his career?

WX Productions

Other Episodes

Episode 6

February 22, 2022 00:40:06
Episode Cover

S5E6: Mac Conwell of RareBreed Ventures is Serving His Community by Turning LP Relationships Upside Down

In The Room with Mac Conwell, the Managing Partner and founder of RareBreed Ventures.  After founding a few of his own startups, Mac’s life changed when he learned about the world of VCs and funders. This inspired him to start RareBreed Ventures, a pre-seed fund that invests in founders outside of large tech ecosystems. Mac and RareBreed provide resources, capital, and financial education to new and underrepresented founders.  This episode discusses; strategies for bridging the gap between funders and marginalized founders, the unique uses of TEDCO, a state-sponsored VC that provides resources to early stage companies in Maryland, and how Mac is utilizing Rule 506(c) to publicly fund new founders.  For The Room Podcast in your inbox every week, subscribe to our newsletter.  0:17 - Where did Mac grow up and how did that shape his view of the world? 1:21 - How did Mac’s early career start put him on a path to entrepreneurship? 3:15 - At what point did Mac decide to quit his job and become an entrepreneur?5:06 - What resources are available now versus when Mac started his career?5:53 -  Who did Mac start his first company with?8:59 - How did Mac’s experience as a founder lead him to venture?12:27 - What is it like to be primarily investing in your home state?16:19 - Is there a “top of the funnel” issue when it comes to who is receiving funding and financial education?18:13 - What is TEDCO and how is it tying venture to state funding?20:13 - Why did Mac start RareBreed Ventures?21:31 - How and why does Mac have a ...


Episode 4

September 07, 2021 00:30:53
Episode Cover

S4E4: Danielle Cohen-Shohet on the future of beauty and disrupting tech for hyper-local businesses

Welcome to another episode of The Room Podcast! In this week’s episode, co-hosts Madison and Claudia chat with Danielle Cohen-Shohet, Co-Founder and CEO of GlossGenius. Danielle, a freelance hobbyist makeup artist, started GlossGenius when she knew that there had to be a better way to manage a business and engage with clients. From scheduling to booking and payments, GlossGenius meaningfully helps freelancers and small businesses in US salon and studio spaces.    In this episode, Danielle talks about building for a specific need and passion, developing a tech platform for hyper-local businesses, and where the beauty industry is going next. Let's open the door.    Season 4 of The Room Podcast is sponsored by our friends at SVB and Cooley. This episode is now live on all podcast streaming platforms, including Apple Podcasts and Spotify.  ...


Episode 4

October 25, 2022 00:40:44
Episode Cover

S7E4: How Jamie Norwood and Cynthia Plotch of Stix Are Transforming Women’s Health, Starting With How Women Shop for Their Health Essentials

We have another incredible episode in store with Cynthia Plotch and Jamie Norwood, the founders of Stix, the company transforming women's health experiences. Stix was founded to “create a convenient, discreet, and judgment-free way to get the products you need.” Cynthia and Jamie walk us through their negative personal experiences that drove them to create Stix. Plus, they share their ideas to evolve Stix past being just a DTC brand and becoming an entire community of women who can help each other with anything health related. Cynthia and Jamie also explain what led them to go down the VC route for funding this journey. Themes in this episode include knowing when is the right time to fully commit yourself to your passion project, today’s women’s health climate, and what's next in DTC. For The Room Podcast in your inbox every week, subscribe to our newsletter. 4:30 - What were the first few years of Jamie’s career like?5:17 - What brought Jamie to Hungry Harvest and broke her into the world of D2C?6:18 - How did Cynthia’s early career influence her decision to start Stix?9:35 - Did Cynthia and Jamie always plan on being founders?11:26 - When did Cynthia and Jamie know that they were ready to go full-time on Stix?16:41 - How would Cynthia and Jamie describe Stix?17:52 - What was the initial mission for Stix when Cynthia and Jamie founded it?19:29 - How has Stix been connecting to its community and helping solve their problems?23:30 - What prompted Cynthia and Jamie to raise VC funding?25:39 - What advice would Cynthia and Jamie give to founders thinking about starting in D2C? ...