Jason Sheppard

What country are you based in?

The United States.

Do you feel your location has an effect on your domain investing?

I think it might skew my interests away from some of the non-repurposed ccTLDs.  I have not dabbled much in .co.uk, .de or any of the country code extensions that are primarily used for their respective geography.

How long have you been involved in domains?

I bought my first domains for investment purposes in 2017.  Funny thing is that I profitably sold a handful of domains in the early 2000s to someone working on a “project”.  In retrospect, I’m confident it was a domain investor, but I have not been able to determine who it was.

Are you a full time domainer?

Domain investing is my primary source of income.  It’s not all that I do though, and it does not currently take up anywhere close to the amount of time that I would be at work if I had a “real job”.  While building up my portfolio, the hours were probably longer than many full-time jobs though.

How did you find out about domain investing?

I was doing some online marketing for a real estate agent friend and stumbled upon GoDaddy Auctions while looking for a domain for him.

How many domains do you currently hold?

I have right at 7000 personally and solely manage a 1400 name secondary portfolio as part of a partnership arrangement.

What's your favourite non .com tld/nTLD/gTLD?

I would have to say .vc.  I unintentionally kicked off a feeding frenzy on that TLD when I had two $5000 sales within 24 hours back in the summer of 2020.  I’m also a fan of .io and .xyz, although both are very underrepresented in my portfolio.

What's the best advice you've been given by another domain investor, either directly or through something they've said on twitter or in an interview?

I remember Braden Pollock talking on a Domain Social about how important it was to have a war chest held back for renewals.  Up until then, I was flying by the seat of my pants and wholesaling/liquidating names to make ends meet.  Fortunately, this advice came at a time when my portfolio was reaching critical mass and starting to generate regular income.  Were it not for this nugget of wisdom, I probably would have continued my old ways and still be liquidating to cover renewals on a monthly basis.

What kind of goals do you set yourself?

I’m not great at setting long range goals, and it is something I need to focus on.  That said, my short-term goal and what I consider my mission is to incrementally improve my portfolio a bit every single day.  Whether it is adding one or more names that improve it or dropping dead weight that is dragging it down.

Who are your top 3 domain investors?

I feel like the proper response to this is the Admiral Ackbar “It’s a trap” meme.

Realistically there are way more than three that I like, respect and owe a debt of gratitude to. The three that I would take a literal bullet for are Mike Cyger, Braden Pollock and Shane Cultra. These three have shaped the way that I invest from my earliest days, and I am proud that in addition to them being domaining colleagues, I consider them all friends now.

What's the toughest part of domain investing?

As a purely passive investor, it would have to be avoiding self-doubt when there is a lull between sales.

How do you structure the domaining part of your day?

I am presently not in heavy acquisition mode, so domain investing does not require me to follow a set schedule.  I will say that when I am growing my portfolio, the hours from 1pm Eastern to 5pm eastern are taken up with last minute decision-making about backorders, scouring ExpiredDomains.net for potential purchases and bidding on auctions.  Nowadays, when I do have accumulated tasks that need to be done, the best way for me to have the energy and focus needed is to knock them out in the morning, the earlier the better.

How do you manage your portfolio?

Not as well as I would like!  I keep things simple by transferring everything to one of my two primary registrars: GoDaddy and Dynadot.  I do still keep my .vc at Epik though, but I am not adding to my holdings in that TLD very often.  Any acquisitions that I make that end up at registrars other than GoDaddy or Dynadot get transferred out in batches 3-5 times per year.  As for the day-to-day management, I would say it all revolves around spreadsheets.  Oodles and oodles of spreadsheets. 

Do you also have any NFTs or Crypto in your portfolio?

I do.  The bulk of my investment in this area centers around the NFT based horse racing game, Zed Run but I do have quite a few worthless PFP NFTs cluttering up my OpenSea wallet.  I have not dipped my toe in the ENS names yet though and my straight crypto holdings are relatively small.

What's the most you've ever spent on one domain?

For me personally, it was $20,000 and for the partnership, $30,000.

Have you ever done outbound? If so, were/are you successful?

I have not.  It is not something that interests me, but I have the utmost respect for the people in our industry that do find outbound rewarding.

You're given $10k to spend on domains, how do you spend it?

I would start by submitting 25 unregistered names per day to BrandBucket.  While those were in the review process, I would start buying great keyword names at GoDaddy auctions using a very specific strategy where I go one bid more than Huge Domains on names in the $500-1000 range. My goal for the auction purchases is to spend about half the capital.  As the BrandBucket approvals start rolling in, I would track my hit rate and build up a pool of even more names to submit based on how many I thought I could get for the remaining capital.  As sales started to come in, I would allocate a portion of the proceeds to future renewals/transfers and reinvest the remainder with a goal of getting to 2500 names as quickly as possible.

Outside of domains, what other business/wealth/personal growth figures do you look up to?

The book that has impacted me the most in recent years was “The One Thing” so I would have to say the authors Gary Keller and Jay Papasan.  

What do you do when you're not domaining?

Mostly, I play Zed Run.  I also do some online marketing and ticketing work for a couple of comedy clubs. Last year I took a two-month road trip which was incredible. I will pack a little bit of road tripping into my drive to Austin for NamesCon later this year, but nothing like last year unfortunately.  

What advice would you give to people just starting out in domains?

Only invest in .com names until you have a profitable track record.  If you can stick with two words domains of less than twelve characters with good keywords, you minimize your risk of having to drop names later.  Make sure you can visualize a business using any domain you before you even consider purchasing it. Most importantly, DON’T SPAM TWITTER THREADS WITH YOUR DOMAINS UNLESS INVITED. (Sorry for the all-caps, but I wanted to make sure they heard me in the back).




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