DomainSherpa – Down The Rabbit Hole – September 11, 2025: The King and Us

As we say on DomainSherpa – all roads lead to domains. And our work with domains has us venturing “down the rabbit hole” into different things all the time. So this is a tech-adjacent, domain name, digital asset, tangent-positive podcast – where we go deep into whatever topics are interesting to us and our audience.

In this episode, JT is joined by Drew and Rick Schwartz — the legendary “Domain King” and one of the key pioneers of the domain industry — to share his candid take on the current state of the market and where the domain space is headed.

The Sherpas dive into Rick’s use of AI, including his custom AI agent “Betty,” his perspective on .ai domains, and some incredible war stories from his career — like the blockbuster sale of Candy.com.

So tune in and jump down the rabbit hole with us!

Down The Rabbit Hole (101:09): Watch | Listen/Download Audio |

Down The Rabbit Hole


This interview is promoted through a media partnership with Escrow.com and Unstoppable Domains.

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DomainSherpa: Down The Rabbit Hole, Audio Only

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This Show’s Sherpas

Andrew Rosener
Andrew Rosener
Andrew Rosener is the CEO of the industry-leading domain name broker Media Options.

Andrew is widely considered a thought leader and expert on domain name value & methodology as well as domain name sales & acquisitions. With 20 years experience with domain names, Andrew has leveraged his knowledge and expertise to make MediaOptions the go-to domain name firm for startup & company domain acquisitions as well as high value domain name sales.

More shows with Andrew Rosener »

Jonathan Tenenbaum
Jonathan Tenenbaum (JT) is an accomplished Internet industry veteran and digital asset expert. An attorney by trade, he spent over 14 years with Web.com in various legal and business roles, including nearly 5 years managing NameJet, the leading domain name aftermarket platform.

Now Chief Operating Officer & General Counsel of MediaOptions, the top domain brokerage agency, Jonathan is also the Host & Executive Producer of DomainSherpa - where they cover all types of digital assets, including crypto and NFTs, and where "all roads lead to domains"!

More shows with Jonathan Tenenbaum »

Rick Schwartz
Rick Schwartz
Rick Schwartz is known worldwide as The Domain King® ̶ the man who turned an $1,800 credit card gamble in 1995 into a portfolio of digital real estate worth hundreds of millions.

He didn’t follow the crowd. He didn’t chase fads. He saw what everyone else missed: that a category-defining domain name isn’t just a piece of internet real estate, it’s a company’s World Headquarters.

Over the last three decades, Rick has sold and leased premium domains earning more than $100 million
in lifetime revenue from his names. And that figure doesn’t even include the current market value of his portfolio, which contains some of the rarest, most powerful domain assets in existence.

While SEO gurus and search “charlatans” told entrepreneurs the name didn’t matter, Rick was closing deals that proved otherwise. From 7- and 8-figure sales to long-term leasing structures, he pioneered the model of treating domains as appreciating digital real
estate instead of throwaway marketing tools.

Rick’s philosophy is simple but uncompromising:
• A great domain name is the foundation of any serious business.
• It’s not optional. It’s not a luxury. It’s your World Headquarters. The difference between a race car and a junker stuck in the driveway.

• Get the mixture right (50% advertising, 50% branding), and your business has lift-off. Get it wrong, and you’ll spin in circles until the money runs out.

For 30 years, Rick has been the voice that scolds, warns, and challenges entrepreneurs to stop renting and start owning. His blunt, unapologetic style has earned him a reputation as the greatest domain investors of all time ̶ voted #1 by his peers.

- Voted Greatest Domain Investor of All-Time 2021
- Voted 3x Greatest Domainer of All-Time
- Epic Pioneer Award 2010
- Domainer of the Year 2005
- Domain Hall of Fame 2006

More shows with Rick Schwartz »

DomainSherpa – Down The Rabbit Hole – September 11, 2025: The King and Us

As we say on DomainSherpa – all roads lead to domains. And our work with domains has us venturing “down the rabbit hole” into different things all the time. So this is a tech-adjacent, domain name, digital asset, tangent-positive podcast – where we go deep into whatever topics are interesting to us and our audience.

In this episode, JT is joined by Drew and Rick Schwartz — the legendary “Domain King” and one of the key pioneers of the domain industry — to share his candid take on the current state of the market and where the domain space is headed.

The Sherpas dive into Rick’s use of AI, including his custom AI agent “Betty,” his perspective on .ai domains, and some incredible war stories from his career — like the blockbuster sale of Candy.com.

So tune in and jump down the rabbit hole with us!

Episode Transcript

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