Andrew Rosener — The Path from Scallop Kingpin to Selling 8-Figure Domains, Achieving Financial Freedom, and How to Live a Contrarian Life (#711)


Artist's rendering of Andrew Rosener.
Illustration via 99designs

“As far as I can tell, all greatness is achieved through novelty. It’s doing things that other people don’t want to do, doing things that other people are afraid to do, doing things that other people wouldn’t even think about doing.”

— Andrew Rosener

Andrew Rosener (@andrewrosener) is the founder and CEO of MediaOptions, which has been the #1 domain broker in the world for the last six consecutive years. Since 2008, Andrew has been involved in more than $600 million dollars in domain sales and has played a pivotal role in numerous high-profile domain-name transactions, including to Elon Musk, to Zoom, and and to Amazon, as well as thousands of others. 

Andrew is an inductee of the Domain Name Hall of Fame; he was named Domain Investor of the Year by TRAFFIC; and he is the creator of the Rosener Equation, a formula for objectively valuing domain names, widely adopted by the industry.

Andrew is also the owner of, the industry’s leading educational podcast. 

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#711: Andrew Rosener — The Path from Scallop Kingpin to Selling 8-Figure Domains, Achieving Financial Freedom, and How to Live a Contrarian Life

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Want to hear another episode with a different kind of broker? Listen to my conversation with superstar agent Rich Paul, in which we discussed lifelong lessons learned from youthful street gambling, creating an enduring relationship with client LeBron James, beating bigger competition, entrepreneurial impulses that lead to darkness, best investments, influential confidence builders, and much more.

#697: Rich Paul — The Power Broker and Superstar Agent Behind LeBron James, Draymond Green, and Others

What was your favorite quote or lesson from this episode? Please let me know in the comments.



  • Connect with Andrew Rosener:

Website | Twitter

Website | YouTube | Twitter | Facebook | LinkedIn

  • The 10 (now 15) Tenets of Charlie Tuna:
  1. I’m not Mother Teresa; I’m here for a profit.
  2. You can’t run a whorehouse without any whores.
  3. Get your ducks in a row before you pull the trigger.
  4. Pay for the mic, say what you want (as Reagan said to Bush during a debate, “I paid for this microphone”).
  5. Don’t crowd the mourners (a reference to not overstepping your boundaries).
  6. Don’t offend my sense of logic.
  7. Play stupid and see what you can learn (go play Mickey the Dunce).
  8. Don’t be backward about going forward.
  9. When you woke up today, what did you tell yourself?
  10. Tire-kickers are like leeches, they suck your time.
  11. Once the toothpaste is out of the tube, you can’t put it back in.
  12. Pay peanuts, get monkeys.
  13. Cheap is always the most expensive option.
  14. Do what you say you are going to do.
  15. Gutter money is good money.


  • [07:06] Who is Charlie Tuna, and what are his tenets?
  • [30:11] Presidential ham and the value of owning coveted domains.
  • [34:35] Tess Diaz enters the picture.
  • [39:25] A domain industry overview.
  • [43:14] Domain investors vs. domain squatters.
  • [46:21] Getting a late start in the game.
  • [50:16] Brokering the sale of
  • [56:50] Why relocate to Panama in the midst of building a business that needed to make $250 per day?
  • [1:00:40] Leasing vs. buying a domain as a startup.
  • [1:10:36] Leasing vs. selling a domain as a holder.
  • [1:13:42] How important is securing your brand as a .com?
  • [1:15:50] Negotiating equity in lieu of cash.
  • [1:19:35] Are we in the early stages of a digital real estate boom?
  • [1:22:03] Why did Andrew buy
  • [1:25:29] Anger management.
  • [1:31:18] Email management.
  • [1:33:57] How will AI affect the domain industry and SEO business?
  • [1:39:53] Alternative uses for domains.
  • [1:48:35] Finding Andrew and his projects online.
  • [1:49:28] Pursuit of happiness.
  • [1:55:08] Avoiding attraction to unnecessary pain.
  • [2:03:13] Three most important influences.
  • [2:06:05] Parting thoughts.
  • [2:08:15] Hunting bigger fish.


“As far as I can tell, all greatness is achieved through novelty. It’s doing things that other people don’t want to do, doing things that other people are afraid to do, doing things that other people wouldn’t even think about doing.”

— Andrew Rosener

“Show me one meaningful piece of art that came as a result of rainbows and butterflies and happiness. Great art comes from pain, suffering, heartache, mental illness, just terrible circumstances. Great art comes from the darkness, not from the light, but you need both. And if you ignore the darkness, you will never get the light — or you’ll always be chasing the light. The light will always be in the distance, but you have to lean into the pain.”

— Andrew Rosener

“I was able to build a business that makes a lot of money and fits my lifestyle. I’ve optimized it for exactly the way I want to live. I don’t want to build, I don’t want to scale it. I don’t want to have 60 employees. I want to have four, five. I want to just keep doing what I’m doing.”

— Andrew Rosener

“I don’t necessarily pursue happiness, I pursue contentment.”

— Andrew Rosener

“I fundamentally believe that we are still in the early stages of domain names and domain value, the early stages of digital commerce and the internet.

Most people in the world have been online for less than 25 years. That’s a pretty short period of time. As we see commercial real estate sort of dying and all the distress in commercial real estate, we’re seeing digital real estate boom. And there’s a direct correlation there — I want to say a causation.”

— Andrew Rosener

“You’d be hard-pressed to tell me a company valued over $1 billion that isn’t on a .com. I think there’s only one Fortune 1000 company that is not on a .com.”

— Andrew Rosener

“I think that a long-enduring, mostly loving marriage is one of the most underrated elements of success in the world. Maybe the most underrated.”

— Andrew Rosener


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for “Best of Apple Podcasts” three times, it is often the #1 interview podcast across all of Apple Podcasts, and it’s been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.


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