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A quick note on audio: We experienced some technical gremlins with the microphones during this recording. While the sound quality isn't perfect, the quality of the information is 10/10.

Is your business sitting on digital gold, or did you buy a liability? In this episode, we sit down with Jeffrey Gabriel, the founder of Saw.com and the man who broke the Guinness World Record for the largest domain sale in history, brokering the sale of a domain for $13 million. Jeff takes us behind the scenes of the high-stakes world of "online real estate." Whether you are a bootstrapper looking for a creative way to secure a premium .com, or an investor looking to understand the wild valuation swings between .net, .ai, and .io, this episode is a masterclass in digital assets. We dive deep into how to value a name, how to negotiate deal structures that require $0 down, and why the "Chinese Chip" market and AI trends are reshaping the internet.

In this episode, you’ll learn:

The $13M Deal: The true story behind the complex bankruptcy sale.

Valuation Framework: The specific metrics Jeff uses to determine if a domain is worth $5,000 or $500,000 (Length, CPC, and Universality).

Creative Financing: How to acquire a six-figure domain name using "Earnest Money" and lease-to-own structures, perfect for cash-strapped startups.

The TLD Debate: Why .net is the "New Balance" of domains, and when you should actually buy a .ai or .io.

Market Trends: From the "Chinese Chip" market to the Crypto crash and the current AI boom.

Timestamps:

(02:36) From selling loans to selling the internet: Jeff’s entry into the domain space.

(11:49) Breaking the World Record: The logistics of selling [suspicious link removed] for $13 Million.

(15:32) Business Strategy: Should you buy the .com, .net, or .ai?

(20:50) The Friend.com case study: Spending $2M on a domain for viral marketing.

(23:51) The Valuation Formula: How to calculate the worth of a URL.

(30:29) Deal Structuring: How to use options and milestones to buy domains without full capital upfront.

(37:34) The history of domain trends: From Ringtones to Chinese "Chips" to AI.

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Jeffrey M. Gabriel, founder and CEO of Saw.com, is a domain industry veteran with over 15 years of experience and over $550 million in completed transactions. Known for high-profile deals like the Guinness World Record-breaking sale of Sex.com for $13 million, the top .ORG sale of Poker.org for $1 million, and the recent sales of Diamond.com, AI.com, Media.com, Data.ai and countless others. Jeffrey and his team have a reputation for delivering exceptional value to clients. Previously, he held key roles at Uniregistry, Igloo.com, and Sedo. An active industry expert, Jeffrey has contributed to Forbes and is a member of the Internet Commerce Association, frequently sharing insights on domain acquisition, sales, and strategy.

Website - https://saw.com/

LinkedIn - https://www.linkedin.com/in/jeffreymgabriel/

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The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/