Road Trip!

Eight days into my current trip and the sense of adventure is finally returning.  I forgot how exhausting it is to pack up and head to a new city every few days, however the new gear is definitely making things A LOT easier.  This 16-day road trip has served as a really good test of my gear.  I’m definitely making some tweaks and ordering stuff on Amazon that I didn’t think I’d need (Mica insulated jacket, travel shaver, etc).  I’ll have to finalize my packing list and then I’ll do a gear post for y’all.

Miami, FL

We started our adventure with a flight from SF to Miami.  While Miami isn’t really part of “The South”, it was definitely worth checking out.  Miami Beach was a lot of fun, but really wasn’t up my alley.  It felt pretty touristy, and I don’t think we heard anything but club music the entire time.  The beach was great and the water was warm.  I heard LOTS of Spanish and had several opportunities to practice with non English speakers.

I think we were the only straight roller-bladers on the beach that day…

Everyone seemed to always be trying to out-flash each other.

At least they are getting straight to the point.

Savannah, GA

This was a huge contrast to Miami Beach.  Tons of white-haired folks on tour busses.  I think we were the youngest people in our hotel by 35 years.  The nearby beach was virtually empty with only a few middle-aged couples wandering around and a couple fishermen.  The town was really pretty but we just felt a little out of place.  We managed to find a few local watering holes and even convinced them to play the presidential debate live at one.  It was a pretty tense experience and everyone was relieved when it ended and they put the music back on.

You don’t want to know how hard it was to get these state line pictures.

The local shopkeep…

Watching the debate in the bar.

John singing a non-country song.  Nobody was interested in our Yankee music.

I thought I sold my M5 in Portland.  I don’t know what it’s doing down here…

Columbia, SC

We were originally going to head up to Atlanta, but heard from several different sources that it wasn’t worth checking out.  So we decided to change the plan and spend a night in Columbia and a night in Asheville.  Seemed to be a good choice, but I have no idea what Atlanta would have really been like.

Columbia didn’t seem to be anything particularly special.  Just a medium-small sized city that had a little bit of a blue-collar/college vibe.

I love these places.

Asheville, NC

This was a funky little town that felt a little out of place in “The South”.  It sort of reminded me of downtown San Luis Obispo, but without the college influence and with southern accents.  We were surprised by the number non-locals that were living there.

Nashville, TN

So far, this has been my favorite city we’ve visited this trip.  It feels a little bit touristy, but the tourists seem to also be from the south.  Lots of friendly southerners and really good live music.

I can’t believe how friendly the staff were here.  We need these on the west coast.


We’re taking it easy here in Nashville today, which is really needed after a hectic 8 days in a row.  Tomorrow, we’re making the 3 hour drive down to Birmingham, AL to visit a college friend and his wife.  We’ll spend a few days with them, and then we’re headed even further south to celebrate Halloween in New Orleans.  We spend 4 nights there and then fly back to San Francisco.  So far this trip has exceeded my expectations and we’re only half-way through!


One year ago I was dying to settle down somewhere.  I had become exhausted with bouncing around for months at a time with nowhere to call home.  I wanted to live in a house, drive a car, buy a motorcycle, and have hobbies.  I wanted to have a core group of friends, roommates, and was even willing to entertain the idea of possibly being in a relationship.

One year into this stability and I am itching for another adventure.  The only problem is that I didn’t realize how hard it would be to say goodbye to my life in Portland.  The final few weeks were truly an emotional roller coaster.  On one hand, I was excited to break free from my day-to-day and explore the world again.  Also, the rain had finally returned to Portland, and I couldn’t fathom the idea of another wet and dark winter.  On the other hand, it was incredibly difficult to say goodbye to everyone who I had spent so much time with in Portland.

It has been less than a week and I still can’t think about everyone I miss in Portland without being overcome with anxiety.  While I’ll probably see everyone I want to see again sometime in the future, its so scary not knowing when that will be or if it will ever happen for sure.  I was in a relationship for several months before leaving.  Saying goodbye to her only added to the heart-wrenching departure.  With all the travelling I’ve done in the last few years, I’ve had to prematurely “pause” several relationships, both romantic and friendly.  Right now, I feel like I’m becoming burnt out from this lifestyle.  I’ll probably feel better once I settle down in Colombia, but at this moment, the goodbye’s are still very fresh in my memory.

On the bright side, the sense of adventure is starting to kick back in.  I just spent the weekend in Miami Beach, and I’m en route to Georgia.  Miami was fun, but that place is really not for me.  It was tolerable for the weekend, but the flashy club-scene of Miami Beach isn’t my style.  I did get to practice plenty of Spanish though!

My road trip will continue with visits to Savannah, South Carolina, Nashville, Birmingham, New Orleans, Austin and Dallas.  From there I’m headed straight to Medellin, Colombia to start my new life in Espanol.  Maybe I’ll do all future posts in Spanish from now on.  Who knows.  The adventure continues…

I’ll keep this updated with new stories, pictures and chronicles of my journey.  I’ve loaded up on entirely new gear for this trip, so I’ll be showcasing what items I’ve chosen to bring along this time.


Up until now, this process has been mostly dealing with automated processes, statistics, numbers, math, databases, etc.  Contacting the owner is a whole new ballgame.  I honestly feel like I could write a whole book on this subject, but I’ll do my best to summarize in one single blog post.

Once you narrow down a list of target websites, you can start contacting the owners to see if they would be willing to sell.  In my experience, I’ve found that you only end up buying ~1% of the sites on your target list.  But if your list is 1,000 domains long, that’s 10 sites!  You can’t go into this attached to any single website.  Most sites aren’t for sale.
I Built an Email Script

I built a semi-auto script to make it very easy and quick for me to send off custom-looking initial emails to the domains on my list.  It was simply a web form with the fields: Email, Domain, Low, High, SUBMIT!.
When you hit submit, this email gets sent off:
$to = “$email”;
$subject = “Interested in purchasing $domain_name”;
$message = “I’m interested in purchasing $domain_name – both the domain and content.  I’d likely be able to pay in the $low – $high range for it.  Let me know whether or not you are open to hearing a formal offer.
(My Name)
(My Company)
(My United States Address)
(My USA Telephone Number)”
Let’s break this down:

  • To Email –  This is sometimes tough to find.  Obviously, start by checking the “whois”.  Be sure to also look through the site to see if they left a contact email anywhere.  If you find multiple email addresses of potential owners, you can send off multiple initial emails.
  • Domain - Duh, the domain that you want to buy.
  • “both the domain and content” – You want to make it clear right off the bat that you want both the domain and content.  Sometimes sellers are only willing to let go of the domain, and have some emotional attachment to the content.  The sites I would target (and the ones you are also probably targeting) rank well because of their content.  I typically wouldn’t ever buy a domain without the content.
  • Low/High – This is going to be your off-the-cuff estimate for the site’s value.  On my spreadsheet, I had all the data about each site right there in front of me (alexa, SEMRush, Compete, etc.)  I used some Excel magic to come up with a low and high range of value for each domain.  The reason I include this on the initial email is to help weed out the owners that have an insane valuation of their website.  It also helps show that I’ve spent some time examining the value of their website, and having a dollar amount portrays a more serious buyer.  The values would be rounded to the nearest $100, so they would come out looking like ($3,200 to $7,800).
  • “open to hearing a formal offer” – This is to show them that you have ran the numbers to come up with a hard offer, but will spend the time to do so if they are actually willing to sell.
  • Name/Company/Address/etc – A lot of the time, a website owner might think this is a scam, being offered money out of nowhere for their website that they had forgotten about.  A proper email signature with an address in a familiar city might help ease their nerves.

While I built a web-form to help speed up the process of sending initial emails, these emails might end up getting caught in spam filters more often.  If you manually wrote the emails straight in Gmail or whatever, it might make it into the owner’s inbox more frequently.

Then I Built a Follow-up Script

I would give them a few weeks, and then throw their contact info into the follow-up-anator 5,000.  This is another script that I made that will send a follow up email once every 2 weeks until I remove them from the follow-up list.  It will randomly send out one of several pre-scripted messages that make it look like I’m a real human who is not trying to scam them.  Here’s an example follow-up email:


I’m contacting you because I’m interested in purchasing $domain – both the domain and content.  I sent you an email some time ago, but never heard back.

Since your site was started way back around $year, there’s a chance you don’t use this email address anymore.  If I don’t hear back from you, I’ll keep following up and trying to find different ways to contact you (other email addresses, facebook, telephone, snail mail, carrier pigeon, ESP, etc.)

If you aren’t interested in selling for any price, kindly let me know and I won’t ever bug you again.

If there is a chance you are willing to make a deal, let me know and we can talk more.

Looking forward to hearing from you!”

If I were to do this again, I’d create some sort of email series that they receive for a set time if they don’t respond in a given amount of time.  You can then tweak this series of emails to best suit your needs.  Also, you’ll know when they finish the series of emails unsuccessfully, and be able to go to more extreme methods of contact to get in touch with them.

If you STILL don’t get a response

Which, you probably won’t.  I’d say that at least 50% of people NEVER respond.  Don’t get broken-hearted.  There are a few more steps I sometimes do to get a hold of the owner:

  • Pick up the phone – The whois will often times have a contact phone # listed.  Call them.  If they don’t answer, leave a message explaining that you’ve been trying to get a hold of them regarding the sale of the site, and since the domain is so old, you’re going to assume that if you never hear back, your calls/emails are getting lost in cyberspace.
  • Snail mail – The whois will also have an address.  Print out a letter and mail it to them.
  • Scour the website for contact possibilities – Maybe the site has a guestbook?  Contact us form?  Comment system?  Anything that can be used to notify the owner that you want to give them cash money for their website.
  • Be a detective – Sometimes they will list personal information, such as their name, business name, location, anything.  Use Google, Facebook, Linked In, Bing, Twitter, MySpace, Youtube, Google+,  or whatever to try and dig up some alternative way of getting in touch with the owner.  The owners who are hardest to get a hold of are probably your best profit opportunities.
  • Check the expiration date and backorder – If the owner is completely MIA, they might not pay to renew the domain.  You can scoop it up for under $100 (just the domain though) through a backorder service like

When you FINALLY get a response

You’ll get a variety of responses.  A lot of them are very unique, so simply require common sense and negotiating skills.  Here are the most popular and how I’ll typically respond:

  • “No thank you” – Great.  You can cross this one off your list.  Be sure to respond with something open-ended and nice: “Totally understandable.  Thanks for getting back to me.  Let me know if you ever have a change of heart!”
  • “What an insult!  My website is worth $100 billion” – At least you get to cross them off your list.  I will come back with something passive-aggressive like: “It is understandable that you may value your website highly.  I simply cannot justify making an offer above $xxx for (domain).”
  • “Actually, says my website is worth $xyz!” – Man, this annoys me so much.  There are dozens of those automatic website value calculators out there.  I’ve seen some that show a value for my website which is less than I make in a month!  I’ve also seen them value websites that make NOTHING at tens of thousands!  Anyway, I usually come back with a few points.  I try to word it in a way that isn’t too mean:
    • “Its good that you are doing your research before selling the website you’ve worked so hard on…”
    • “There are dozens of these online calculators, all with very different values” – then I’ll go through and link them to 5 different value calculators that show a considerably lesser value.
    • “Value calculators do the estimate automatically without actually looking at your site”.
    • “I have cash behind my offer, and am ready to buy your site; these value calculators do not represent cash real offers”.
  • “Maybe, but I don’t want to sell you the content!” – I will typically let them know that the content is a big part of the deal.  Sometimes its just a matter of removing their name from the site, or just a portion of the content.  If they are still hesitant about the content, just come back with a super-low-ball offer for just the domain, and then get a cheap writer to come up with your own content.
  • “What are you planning on doing with it?” – They typically don’t want you to turn their baby into a porn site.  I’ll usually say something to the effect of: “I specialize in acquiring older sites and fixing them up.  I’ll start by applying a modern-looking template, improve the navigation, add user-interactive features such as a comment/question/answer system, and then try and recuperate my costs by selling a few ad slots”.
  • “I don’t know how to transfer a website, you seem like a scammer!” – Most people think that anyone on the internet is a scammer.  Kindly let them know that you’re willing to send them payment however they prefer (paypal, paper check, bank check), and you are the one sending them money.  Also, show them your facebook page, twitter account, past sites you’ve bought, personal blog, etc.
  • “Yes, lets do it!” – Finally they agree.

Congrats, you’ve just finished a 1,600 word post!  Next up: Making the Payment and Transferring the Website.