Late last year, Spencer Rascoff, the former CEO of Zillow, reached out and invited me to be part of a new advisory board for his latest real estate start-up, Pacaso. I knew Spencer when he was at Zillow and we kept in touch over the years. I don’t sit on many advisory boards, but I thought the idea behind Pacaso was pretty cool and I agreed to participate. In a nutshell, Pacaso makes second homeownership more accessible by allowing buyers to purchase shares in a vacation home rather than having to purchase the entire property. It works like this: Pacaso purchases the home, then sells ownership shares of a limited liability company to up to eight individuals who share ownership and occupy the property at different times, proportionately. Pacaso manages the properties including moving in and out the personal property of each owner when they stay in the property. Financing is available, and a buyer can purchase a share of a $3.2M property in markets like Napa Valley, Park City, Malibu, and Palm Springs for as little as $400K. Potentially, this can make second homeownership much more attainable for a lot of people.
Spencer started the company with Dotloop founder Austin Allison who serves as the company’s CEO. The latest round of financing valued the company at roughly $1 Billion, making it the fastest company in U.S. history to achieve so-called unicorn status. Pacaso says that second homes sit vacant more than 90% of the time, while Pacaso properties are occupied year-round, which is safer for communities, and more supportive of local businesses such as restaurants, grocery stores, and beauty salons. It makes a lot of sense. The biggest challenge for Pacaso is convincing local residents and municipalities that they are not a timeshare company or just another Airbnb. I recently spoke at a city council meeting on behalf of the company and did my best to make the case that Pacaso lowers barriers for buyers, improves local economies, and adds diversity to communities that are not always known for it. Pacaso also lists their properties on the MLS and pays commissions to real estate agents.
Besides supporting what I think is a good business, I’m enjoying watching two elite entrepreneurs build a world-class start-up. These guys know how to play at the big table, but I can also tell you that Austin and Spencer have an appealing combination of intelligence and humility. They are both young and incredibly successful, but always seem to be eager to listen and learn. I have no doubt that Pacaso will continue to be successful and I look forward to helping out.
In this episode, I share my perspective on the tragic killing of Renée Nicole Good and why moments like this demand clarity, restraint, and leadership rather than instant conclusions. We’re living in a time when emotion travels faster than facts, and division often fills the space where understanding should live. My goal here isn’t to inflame, but to add context, acknowledge pain, and encourage thoughtful reflection while the facts are still coming into focus. I hope you’ll watch with an open mind and consider what responsible leadership looks like in moments that test all of us.
In this episode, I talk about why progress rarely comes from perfect ideas or moral certainty—and why waiting for purity often keeps us stuck. Idealism can feel virtuous, but history shows that real change happens when people are willing to act, accept imperfection, and move forward anyway. For our community, that means choosing momentum over stagnation, results over symbolism, and responsibility over comfort. If we’re serious about building power, dignity, and lasting progress, this is a conversation we need to have—honestly and without illusions.
In this episode, I talk about something we’re almost never encouraged to say out loud: wealth is power—literally. Not likes, not outrage, not visibility. I break down why real influence comes from ownership and leverage, not consumption; why income feeds families but equity builds dynasties; and why a wealthy Latino with a clear purpose shouldn’t be seen as a problem, but as proof of what’s possible. If you’ve ever felt uneasy talking about money or ambition, I’d love for you to watch this one and think about what “owning more” could look like for you and our community.