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James Iles

An Interview With Jason Calacanis: Angel Investor and Owner of 20.com

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By James Iles, Jan 26, 2016
  1. James Iles

    James Iles NamePros Writer PRO Gold Account VIP Trusted Blogger

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    Today, we have the great pleasure in bringing you an interview we conducted with Jason Calacanis. For those of you who don't know about him, Jason is a very successful angel investor and the creator of some of the Internet's most valuable websites.

    Some of @jason calacanis's achievements include creating the website Mahalo.com, co-founding Weblogs Inc, and most recently creating the LAUNCH festival, an annual event with an average of 10,000 attendees.

    Jason has made many notable investments as an angel investor in companies such as Tumblr, Uber, and Evernote. He also happens to be the owner of one of the most sought after domain names on the Internet: 20.com.

    Having acquired the domain name in 2006, Jason can now expect to sell this asset for a multiple seven-figure sum. In the interview below, we ask Jason a number of questions related to domain names, 20.com, new gTLDs, and his advice for startups in relation to domain names.


    NP: What drove you to buy 20.com for $75k in 2006? Was it for a specific company or did you see intrinsic value in it?

    Jason: I wanted to start a Wikipedia-like search engine, where consumers would rank the top 10 or 20 links. My thinking was, well, you’re never going to need more than 20 links about a topic. I had also bought kokua.com and mahalo.com at the same time; after testing the names with people, I found everyone loved Mahalo.com.


    NP: We've noticed that over the years you've received increasingly larger offers for 20.com. Were you ever tempted to sell the name at a lower price, considering your original acquisition fee?

    Jason: I’ve been super busy angel investing and never considered what it was worth. Given that I’m getting 20 emails a week, I think it’s time for me to let someone use it. It’s kind of a waste to let these premium domains sit and collect dust in my mind.


    NP: Would you consider yourself to be a domain investor? Do you plan to make more domain purchases after selling 20.com?

    Jason: No, I’m not a domainer, I’m an angel investor. I run launch.co, which includes an incubator, conferences and my angel fund. Domains are awesome assets for startups, but startups are driven by founders -- so I chase the founders, not the domains.


    NP: What is the most expensive domain you've ever purchased? Can you share the domain name and/or the price that was paid?

    Jason: Tied: Inside.com and 20.com, around the same price (and same value today I would bet).


    NP: What's your favorite domain that you own?

    Jason: Kokua.com, Loaa.com or ADAY.com.


    NP: What was the first domain you ever purchased?

    Jason: Can’t remember!


    NP: What level of importance do you place on a domain in your marketing stack?

    Jason: It’s awesome if a startup can own a premium domain -- eventually. You don’t need it from day one. Eventually, if your business succeeds, it’s a great checkbox to own Uber.com or Calm.com.


    NP: What do you think about the new gTLDs such as .club, .tech, .technology, .xyz? Would you recommend that startups use them?

    Jason: I think these domains are great for starting out, but eventually you need to get the .com version of your name. Ironically, the more gTLDs they create, the more valuable the .coms become. It’s like a bunch of cities popping up around Manhattan: as they go up in value, the city in the center goes supernova.


    NP: Do you advise startups on domain name acquisitions? If so, can you share some of your common recommendations?

    Jason: I do this often, and the conversation is usually “fake it until you make it.” So, there is no problem being TeslaMotors.com forever. Obviously the car and people who make the car are the most important aspect of the success of that company.

    However, if the person with Tesla.com decides they want to buy a nice condo or house, sure, it’s a great idea to spend $500k or $1m buying that name. If the person with Tesla.com waits too long, they miss the opportunity to take 10% of the purchase price in stock (or some kicker like that). They also risk pissing off the management team at a startup, who will eventually realize, “well, our cars are the best in the world and this domain name is not essential.”

    --

    Thanks to Jason for taking the time out of his very busy schedule to take part in this interview.
     
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  4. James Iles

    About The Author — James Iles

    James is the lead writer for NamePros' Blog and founder of Iles Media, a domain name broker working on both acquisitions and outbound sales. For all inquiries relating to stories and interviews, please email: [email protected]

    This is James Iles's 140th blog post on NamePros. View all blog posts

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  5. Comments (25)

  6. Skyvisum

    Skyvisum Top Member VIP

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    Thanks again for the write you James.Keep up the good word.
     
  7. DNabc

    DNabc Established Member ★★★★★★★★★★

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    Jason was always a smart investor and knew the value of domains while others were saying that they weren't necessary because of Google, apps, etc
     
  8. Skyvisum

    Skyvisum Top Member VIP

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    He must be really good
     
  9. Brandingtheweb.com

    Brandingtheweb.com 123Capital.com VIP

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    NP: What's your favorite domain that you own?
    Jason: Kokua.com, Loaa.com or ADAY.com.

    Interesting these are his favorites when he owns 20 and inside .com's.
     
  10. Jasonn

    Jasonn Top Member VIP ★★★★★★★★★★

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    he seems to have a lot of money to throw around. earned or born into it?
     
  11. Eric Lyon

    Eric Lyon Member Services, NamePros Super Moderator PRO Gold Account VIP Trusted Contest Holder

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  12. MikeHu

    MikeHu Established Member

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    Great interview!
    Thanks a lot James and good luck Jason :)
     
  13. vickyhunter

    vickyhunter Domain Spider Gold Account

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    There you go ! Excellent interview. Thanks @James Iles
     
  14. ismailbiz

    ismailbiz Established Member

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    Awesome interview. Thanks you very much
     
  15. techname

    techname Established Member

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    Thanks, interesting stuff.
    I was a little surprised to hear that Jason thought that Inside.com was worth around the same as 20.com, maybe because Inside has been developed?
     
  16. korganian

    korganian Top Member VIP ★★★★★★★★★★

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    You mean Kombucha?
     
  17. nvdomains

    nvdomains Established Member

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    Good interview. If every entrepreneur/investor have this clarity of domain names and their importance, we will see golden days.

    I liked his clarity on .coms and gTLDs - unfortunately, even several domainers are not understanding that simple logic.
     
  18. deez007

    deez007 The More I Learn The Less I "Know" VIP

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    Awesome interview and a very refreshing perspective indeed from some one with massive street cred!
     
  19. CrocodileDundee

    CrocodileDundee Top Member VIP

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    Great Interview, I love the domain Mahalo.com :D
     
  20. Domain Shane

    Domain Shane Top Member DSAD.com Staff PRO ICA Member VIP ★★★★★★★★★★

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    Does Jason own any part of Namepros? There has been a lot of coverage of his 20.com and he has the money and the interest. Can anyone confirm or deny :)
     
  21. Eric Lyon

    Eric Lyon Member Services, NamePros Super Moderator PRO Gold Account VIP Trusted Contest Holder

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    I can confirm that he does not, but some of us are fans of his work. :)
     
  22. Jasonn

    Jasonn Top Member VIP ★★★★★★★★★★

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  23. Edward Smeu

    Edward Smeu Top Member PRO VIP

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    He invested in a lot of companies, including Uber and he did a great job.

    There is a quite big and comrehensive interview with him on Quora which was just released and it is a must read!
     
  24. pablohc86

    pablohc86 Top Member VIP

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    why mahalo is liked so much? i don't like so much that name..
     
  25. coconut

    coconut Established Member ★★★★★★★★★★

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    Great interview - thanks James.
     
  26. techname

    techname Established Member

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    I think because it means "thank you" (also gratitude, admiration, praise, esteem, regards, or respect) in Hawaiian, so it conjures up a very positive image or feeling, which is a good thing for any business.
     
  27. pablohc86

    pablohc86 Top Member VIP

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    Now it make sense. Thanks for explaination
     
  28. Keith DeBoer

    Keith DeBoer Top Member PRO VIP

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    Awesome insights!!
     
  29. okinno

    okinno New Member

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    Nice article
     
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