Spencer Rascoff is a serial entrepreneur who co-founded Zillow, Hotwire, Pacaso, dot.LA, Queue, heyLibby and 75 & Sunny Ventures. He served as Zillow’s CEO for a decade and teaches entrepreneurship at Harvard.

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Guest Resources

Pacaso – Luxury vacation home ownership, elevated. Own your family’s dream vacation home, today.

Invest in Pacaso – Be part of Pacaso’s growth as an early shareholder.

75 & Sunny – 75 & Sunny is an LA-based startup studio and venture fund that incubates and invests in bold solutions to everyday problems.

3 Value Bombs

1) Once you found success in business, you will be able to redirect your interest and enthusiasm to other things. Success driven people are satisfied and they don’t feel the need to continue to strive to build and run larger organizations.

2) You need passion when you are starting something because you will encounter enormous challenges and in order to overcome it, you need to run through walls and be super fired up about it.

3) Surround yourself with people who are better than you. Entrepreneurship is not a solo endeavour. In real life there are teams and team of teams. Entrepreneurship is a team sport so make sure you surround yourself with great teams.

Show Notes

**Click the time stamp to jump directly to that point in the episode.

Today’s Audio MASTERCLASS: Changing the Way We Own Homes.

[1:30] – Spencer shares something that he believes about becoming successful that most people disagree with.

Once you found success in business, you will be able to redirect your interest and enthusiasm to other things. Success driven people are satisfied and they don’t feel the need to continue to strive to build and run larger organizations.

[2:25] – Spencer gives an overview of his background.

He grew up in New York and Los Angeles to an affluent family. He went to college not sure of what he wanted to do and started investing in banking but he wasn’t satisfied so he moved to private equity but still was not satisfied.
He then wanted to do start ups. He started Hotwire, an online travel company and experienced ups and downs through Sept 11. He sold it, moved to Seattle and worked with Expedia before he started Zillow which was a new chapter of incubating new start ups.
In Zillow, he is mentoring, teaching and advising younger people in the early stages of their career to learn from his success and experience.

[4:03] – Spencer talks about starting Hotwire , Zillow and 75 & Sunny.

You need passion when you are starting something because you will encounter enormous challenges and in order to overcome it, you need to run through walls and be super fired up about it.
When he started Hotwire at 23, he was excited in providing the ability for people to travel and save a lot of money or get a 4 star hotel for a 2 star price. He was able to become a leader in the online discount travel space.
In the early stage of Zillow in 2005, brainstorming was boring and slow and lasted for a couple of months until they decided to look into the problems they are experiencing in their own lives and that time they were all buying homes. He was shocked to see how ineffective the tools that are available online and that there is no leading real estate internet sites that empowered consumers but only empowered the real estate agent.
The original idea of Zillow is a consumer-prioritized product and the killer feature is trying to figure out how much each home is worth putting a price in every rooftop. It had a lot of virality and even crashed the website on the first day because a million of people used it. After a month, 4 million people used it.
After he left Zillow, he started 75 & Sunny. He had a great run being the CEO of Zillow for 15 years , he accomplished a lot and achieved what he wanted to achieve. He didn’t know what to do next, he commuted from Los Angeles to Harvard Business School and taught a course of managing tech ventures every week for a semester.
He used teaching as a ‘palate cleanser’ to clear his head and after a year of teaching experience, he started 75 & Sunny which today is a start up studio and incubator for start ups and early stage investors in start ups.

[8:13] – Spencer talks about the origin of Pacaso.

Owning a second home is awesome and it allows you to be a better version of yourself when you are in a vacation home, however, its really expensive and generally not available to most normal people.
What they endeavour in Pacaso is democartized access to second home ownership so more and more people can experience the benefits to ownersuo of a vacation home.
You can do that to fractualization which is taking a luxury vacation home and sell it in eights to be co-owned by 8 families. You buy eigth of the property price and have it for 6 weeks in 1 year. Pacaso will furnish and manage the property. There is a Pacaso App to schedule the visits and handles everything.
They have now sold $1 Billion of this properties in many places around the world and have raised a $200 M of venture capital with the idea resonating with their thousand of owners recommending it to their friends and families.

[10:36] – Spencer talks about when did he think Pacaso might work.

He started it with his former folks from Zillow and thought that its going to be a great idea but was not sure of the logistics of scheduling or owning a second home with strangers. It only became clear when they were already in operation that they can handle the small details with enough ingenuity and innovation.
Start ups is a roller coaster ride but they knew quickly that something is going to work.

[12:15] – A timeout to thank our sponsors!

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[14:49] – Spencer talks about how the model work and what are some successes to date. Revolutionizing start ups to raise capital and Pacaso launched a Reg A.

There has been a gap between private venture capital and public markets. Pacaso raised $200M of private venture capital from leading venture capital but they were not ready to publicly traded.
Fortunately, the government under the job act called Reg A and under the Reg A, companies can live in their middle ground IPO like Pacaso to file audited financials with SEC (Securities Exchange Commission) 2x a year rather tha 4x a year to sell shares to the public which don’t actually trade the way the stock market does.
This is a way to democratized access to investing in the asset class private venture backed companies. Reg A allows retail investors and regular people to buy shares in this company before they go public. Reg A allows companies to raise $75M per year which is the maximum that they permit and Pacaso launched this fall of 2024.

[17:54] – Spencer talks about the future of startups and IPO market.

There is a high bar for companies to get public. Part of that is good for investors and companies but there are certain regulations that may get more difficult.
The creation of Reg A means that these regulation are reduced and there is a middle ground.
We also see a growth in secondary offerings where companies that choose to stay private for a longer time are providing their employees and early investors with equity that turn their shares in the company with actual cash having new investors come in and buy existing shares with owners. A good examplof it is Space X.

[20:11] – Spencer gives his key take away.

Surround yourself with people who are better than you. Entrepreneurship is not a solo endeavour. In real life there are teams and team of teams. Entrepreneurship is a team sport so make sure you surround yourself with great teams.

[20:50] – Call to action.

Pacaso – Luxury vacation home ownership, elevated. Own your family’s dream vacation home, today.
Invest in Pacaso – Be part of Pacaso’s growth as an early shareholder.
75 & Sunny – 75 & Sunny is an LA-based startup studio and venture fund that incubates and invests in bold solutions to everyday problems.

[23:18] – Thank you to our Sponsors!

HubSpot: When you combine the power of Marketing Hub and Content Hub, you can have your best quarter, every quarter. Visit Hubspot.com/marketers to learn more!
ThriveTime Show: Attend the world’s highest rated business growth workshop taught personally by Clay Clark & NOW featuring Rich Dad Poor Dad Author Robert Kiyosaki and Eric Trump at ThrivetimeShow.com/eofire!

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