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March 25, 2014

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Course Correction: Why Commercial Airline Pilot Bob Olea is Now Banking on Domains as Well as Planes  

By Ron Jackson 

There is something about the domain business that attracts people from all walks of life and every step on the economic ladder. We've got everything from butchers and bakers to candlestick makers plying a trade that has made more than a few people millionaires. Some of those have been teenagers, some have been septuagenarians and all have been people who have proven that, no matter who you are, this is a business where anything is possible for those who can master the ins and outs of this unique occupation. 

The flip side of that is that many others have washed out, seduced by the undeniable opportunity but unable to connect the dots in a puzzle that looks much easier to solve than it really is. Like many tech based businesses, this is one where the winds are constantly changing, making it a bumpy ride for everyone, including those who eventually reach the summit. 

With no one knowing what is around the next corner, I imagine that navigating the domain business might be a bit like trying to fly a 747 in zero visibility with all of the instruments down. That's why I was curious to know what a guy like veteran commercial airline pilot Bob Olea, who already has a successful career, is doing in a wild and wooly business like this? 

Bob Olea 

I know the economy is rough and a lot of people are holding down two jobs, but Olea doesn't have to do that. Bob has his reasons of course and, as I suspected, there is a fascinating story behind his decision to continue cultivating a domain business he started in 2006 while continuing to fly people around the world for United Airlines. It's a story filled with more ups and downs than a hang glider in a hurricane. From being forced out of his childhood home by a bulldozer to having his life upended by 9/11 to riding domains to redemption, Olea has lived a life that would be full for someone twice his age. If you don't know Bob, you should - so allow me to introduce you.

Gloria & Frank Olea - Bob's parents in a photo 
shot shortly before they were married in 1958.

Bob Olea is a rare bird on many levels. In addition to being the only airline pilot/domainer that I am aware of, Olea is living proof that at least one creature previously thought to be mythical actually exists  - he is a Los Angeles area resident who was actually born in Los Angeles! "Yes, I am one of the few LA  natives," Olea laughed. "My mother Gloria was born in LA too! She met my father Frank when they were both attending college classes in the late 50s. He was a young banker at the start of what would be a long career and she was attending a local college deciding what to do after graduating with highest honors from St. Mary's Academy, a private LA Catholic prep school that she'd attended on a full scholarship."

After Olea's parents married in May 1958, they began a family that would grow to six children, Bob and his four brothers, plus one sister. Frank and Gloria's decision to raise their kids in 

one particular neighborhood would wind up having a huge influence on Bob. "We grew up in Westchester, a cozy suburb right next to Los Angeles International Airport (LAX) - literally a couple of blocks away from the runways!," Olea exclaimed. "I remember sneaking onto the airport grounds with my brothers and the other neighborhood kids via the sewer tunnels so that we could watch the big jets land. Try doing THAT today!," he laughed, noting that it was a much simpler and safer time back then. 

Bob Olea (3rd from right) with his parents, sister and four brothers in a shot snapped a year
before older brother Mark (at far right) suggested they take flying lessons together.  

"In the summer of 1969 we heard that the very first 747 was finally going to fly into LAX. We all went down to the end of the street to see it come in. It was the marvel of the day and we were amazed at how enormous it was! I had no idea then, but living next to a big airport and seeing and hearing the jets all day would later play a big role in my life," Olea said.

Plane landing at Los Angeles International Airport
Image from Bigstock

Even so, it took a while before Bob knew exactly what he was meant to do, partially because "progress" uprooted his family from their home next to his beloved runways. In the mid 70s the city of Los Angeles starting buying and demolishing older homes to make way for expansion. With the growth of the airport and arrival of bigger modern jets, a noise buffer zone was needed and the neighborhood Olea grew up in was literally bulldozed to the ground to help provide it.

"We relocated to Hacienda Heights, a very nice community that was about 40 miles inland and way too quiet," Olea recalled. "It was very strange not hearing the jets anymore! I was the typically unfocused and carefree teenager, but in my senior year of high school 

Mark, one of my older brothers, suggested that we enroll in a Private Pilot ground school class being held at night. It sounded really interesting so I happily agreed. I was immediately hooked, and at the ages of 17 and 18 we started taking flying lessons as well. I still vividly remember that first flight lesson – when I pulled back on the controls and we lifted off I had my first 'lightbulb moment', and the inspiration that I needed to finally start making a plan for my life. I looked right at the instructor and said “From now on, I'm going to be a pilot!” Olea declared.

"I immediately enrolled in extra classes so I could graduate early, instead of wasting any more time in high school. At 17 I enrolled at Mt SAC, a local community college that offered an Associate of Science degree in Commercial Flight. On a funny side note – Rick Schwartz (AKA "The Domain King") and I discovered a few years ago that we were both attending Mt SAC at the same time! We probably passed each other on the quad a few times. WAY before the Internet unfortunately!," Olea laughed.

"I felt like I was finally in my element. I went from lackluster grades in high school to actually making it to the top of the Dean's List! I had recently read Napolean Hill's classic book Think And Grow Rich, an inspirational classic that I would recommend to anyone. I applied some of his timeless ideas to my newfound career path. For me it was more like 'Think And Be A Pilot'!"

Just as Olea's life took that exhilarating turn, fate would deal him another card and this was not a good one. "Tragically, my closest brother and best friend Mark, the one that had sparked my initial interest in flying, was unable to stay enrolled in college or keep flying due to the onset of a debilitating lifelong illness. So I abruptly lost my best friend and wingman," Olea ruefully remembered. 

Olea decided to press on alone but his close  relationship with Mark taught him a lesson that would pay dividends for the rest of his life. "I learned that if you want to be successful in any area of endeavor, you need to be around 

Mark Olea

like minded and successful people in that field. That concept is also very true in the domain business," he observed. "Some people don't understand the value of going to domain conferences like T.R.A.F.F.I.C., but the domain business, like many businesses, is a PEOPLE business. In this business, your network is much more important than some people may realize. One of the best ways to start or grow your network is to go to a domain conference," Olea said.

Through the early and mid 80's the airlines were going through a major downturn but Olea refused to sit still, knowing the tide would eventually turn and we wanted to be ready when it did. "It's a very cyclical business, so I spent most of those years working on my various flying licenses and ratings, while finishing my college degrees," Olea said "I worked at the usual assortment of night, weekend and summer jobs. Anything to get an extra hour or two in the air! Flight training has always been a big financial commitment, and I looked at every expense in terms of 'flying units'. I was really struggling to keep my momentum when something very unexpected happened." 









"I had the good fortune to work at Mt SAC with a very classy lady from the South, Henrietta Gregory. Her husband had actually been a World war II fighter pilot! Although we were almost 40 years apart in age we instantly became lifelong friends,"  Olea related. "Out of that friendship she altruistically offered me a private scholarship with no strings attached! I was completely overwhelmed by her generosity and when I told her that I had no idea how I could ever pay her back she told me that it was a gift. I was floored and humbled! She only asked that I consider doing something similar for somebody else one day. She asked me to 'Pay It Forward' light years before it was trendy!," Olea said. 

Image from Bigstock

That has something Bob has done many times time then, including one instance that drew a lot of media attention when Olea purchased JeffBezos.com in an aftermarket auction and turned the domain over to the founder of Amazon.com at no charge - an unexpected gesture that was highly appreciated by the legendary Internet entrepreneur.

He is currently working on something dramatically bigger with PPX International Chairman Gregg McNair - a planned charter flight to Africa some time in 2013 to raise funds and awareness for The Water School, a charitable organization that has been strongly supported by the domain industry. Their goal is to fill a large jet with people from the domain and entertainment industries who want to help change thousands of  lives for the better. 

With the generous help Olea got from Henrietta Gregory he was able to finish up the requirements for his Commercial Pilot License and his Associate's Degree in Commercial Flight in 1980. However with the industry going through the downturn at that time his new credentials sat unused while Olea waited for the cycle to shift. "I never let go of the dream," Olea said. "I had already seen the path and built a mental road backwards to where I was, and nothing was going to stop me in my quest! In the meantime I just kept going to classes, and kept working on finishing my college degrees. At that time a Bachelor's Degree was a standard requirement for any aspiring airline pilot."

"I finally finished up my Bachelor's Degree at Cal State LA in 1985 and started looking for ANY flying job. The airlines were just starting to do some limited hiring, so it was  really important to just get a toe in the water. I answered an ad in a local aviation paper, the Pacific Flyer, for a job towing banners. I had my first flying job – for a  whopping $7 an hour! It was fun for a couple of months, but I ended up doing it for almost an entire grueling year," Olea said.

A Convair 440 in flight (public domain image)

"Fortunately that job allowed me to meet another pilot that helped me get a job flying Convair 440s – a great classic 50-seat radial engine plane from the 1950's airline era. It was the perfect plane to really cut your teeth on. An amazing amount of dials and switches, all manual cables and analog instruments, and no autopilot or fancy navigation gear!," Olea recalled with so much enthusiasm you would have thought he had just gotten Airplanes.com for $50.

"About a year later, with the help of another friend I was able to land my first job flying big jets, as a DC-8 copilot. I spent the next couple of years flying all over the world, with 

a succession of different airlines, but I still always kept my eyes on the prize. I would spend a Saturday every month or so typing out pilot applications and sending updates to  airlines. I think when I finally threw those copies away it was a stack about 2 feet high!," Olea said.

"The travel and experience I gained in those years was amazing, but I sure wouldn't want to do it again. I also wouldn't trade that time and experience for anything either! Seeing the world like that is a great teacher, and it really makes you appreciate where you live and your family," Olea observed.

Bob Olea getting ready to take off on his 
1st flight
as a United Airlines Captain in 1997.

Olea's perseverance finally paid off and big things started coming his way. "In 1989, after living in Texas, Michigan, Florida, and South America for about four years, I was hired for my dream job – as a pilot for United Airlines. The following year I had the good fortune to meet the love of my life – and soon to be my wife, Trudie, on a blind date. In love, it's always better to be lucky!" 

"One of the real highlights of my life was the day in 1997 when Trudie came to Orange  County Airport with our young children to surprise me at the gate when I arrived on my very first flight as a brand new A-320 Captain. It  had taken me exactly 19 years to the day to go from my first solo in a Cessna 150 to my first Captain flight in an A-320! Flying from Denver to Orange County airport, with my family at the gate meeting me with smiles and balloons - BIG box FINALLY checked!!," Olea said, still smiling broadly at the memory.

Trudie Olea paying a visit to Bob's "offfice"

Unfortunately, just as the the airline business is cyclical, so is life. It would have been nice to end this story with "...and they live happily ever after" following the day Olea donned his Captain's hat. Over the next decade Olea did enjoy mostly blue skies and a growing family (he and Trudie have three children) but then one historic event changed his world and just about everyone else's in America - 9/11 - the terrorist attacks that brought down the Twin Towers in New York. 

"We were all blindsided and in a few spellbinding hours everything that we had all worked years for was in jeopardy," Olea remembered. "I was actually in downtown New York City on the night of 9/10/11. We had mechanical delays that night on the last leg of a multi day trip and we almost cancelled our flight home from Newark to LAX. I was an A-320 Captain for a major airline, livin' the dream, and just starting to enjoy the sweet spot of my airline career. I was happily married to a beautiful woman, and together we were growing a family of our own. Suddenly, in a day, everything had changed!"

Still, as Alexander Graham Bell famously said, ""When one door closes another door opens." Olea recalls his doors very well today. "Sometimes when people ask me how I became a domainer I tell them that “Terrorism caused it!,” Olea said. "An odd twist but actually very true. After the disastrous events of 9/11 I realized that I was a single skill set, single employer and single income source person. Not a good place to be in today's world! With the future of United in bankruptcy court and now doubtful, we were facing massive pay cuts and trashed pensions. With a family of five to care for by now, I felt that I needed a backup plan real quick! After some 

New York City - 9/11/2001
Image from Bigstock

research I decided that a good option would be to become a real estate appraiser. It fit well with my flight schedule, and it would allow me to put food on the table if United dissolved," Olea said. 

"I also decided to obtain my real estate broker license so that I would be able to do pretty much anything that I wanted to do in the real estate field. After working part time for a few different companies I decided to become an independent broker. The airlines were stabilizing and I didn't want or need another job anymore. It was now 2006, and I had already been looking around for some domain names for my real estate business. I kept bumping into the same owners and after a few more weeks of research I made the all important intuitive leap that domains are virtual real estate! I decided to switch my business activities to the domain business and I've never looked back!," Olea declared.

"Probably the one event that finally made me pause and take a closer look at domains as a business was the now well known article in the December 2005 issue of Business 2.0 titled 'Masters of Their Domain' by Paul Sloan. It hit my mailbox right when I was looking for some domain names for my real estate business. It reinforced what I was already feeling and it gave me a deeper insight into the depth of the market and the possibilities in domaining. By the time that the magazine's closing issue with Kevin Ham on the cover was delivered (featuring another Sloan article, 'The Man Who Owns the Internet') I was already smitten," Olea said. 

"I started devouring anything that I could find online about domains. Reading DN Journal's Wednesday sales report is absolutely mandatory for anybody serious about the business of domaining! I found out about the T.R.A.F.F.I.C. conference and figured out Rick Schwartz's email. After a few exchanges he invited me to attend. I didn't know a soul, and I arrived late to one of the evening parties. At the time I didn't know even one other domainer, so I must've stuck out like a sore thumb, or at least a party crasher! As I wandered around Barbara Neu (wife of T.R.A.F.F.I.C. Co-Founder Howard Neu) noticed me and asked her son Ray to go over and talk to me. After discovering that I actually had paid to come to the show Ray and I ended up talking more and discovered our mutual love of airplanes. We've been the best of friends ever since!," Olea said. 

"The names that I flew in to try to bid on at the show's auction ended up going for way more money than I wanted to spend, but I did end up buying a few nice lending names anyway. I still own them, and I'm (still!) planning on developing them," Olea added.  

Pals Ray Neu and Bob Olea at the
2009 T.R.A.F.F.I.C. Silicon Valley Conference

The opportunity Olea has had to travel the world has given him a lot of insight into how domains are used in places outside the United States. "In Germany and some other parts of Europe you see domains with dashes," Olea noted. "In Australia you see a lot of .com.au names but very few .coms. In Japan you don't see domains used as heavily in visible advertising as in some other parts of the world. There are many other good examples that others could speak to better than me, but overall I'd have to say that in many countries ccTLDs are preferred for local business, but for big business .com is still the king."

Image from Bigstock

At the top of this article I mentioned the constant changes that roil this industry. Perhaps the biggest ever, the introduction of hundreds or even thousands of new gTLDs, is expect to start happening in next year or two. Obviously, those have not escaped Olea's attention. "I have some mixed feelings about the coming launch of all the new gTLD's," Olea said. "On one hand it may be one of the biggest opportunities in years. In the same way that a rising tide floats all boats. On the other hand, it may partially deflate the established gTLD marketplace, as money that would normally have gone into the current name space is diverted into the flood of new strings. Simple supply/demand economics. I think that it's really going to depend on public acceptance and the level of execution by the new registries. There will likely be some solid winners, and possibly a few losers," Olea opined.

"Like any inflection point – there's going to be some very unexpected outcomes," Olea continued. "Mostly because 'The Law of Unintended Consequences' usually reveals itself in very unexpected ways, and almost always after the fact. From the inevitable changes there's going to be some people and a few companies that will seize the moment in a large and very successful way. It's been that way for hundreds of years. You can't change the wind but you can adjust your sails. I'll be watching the leaders and following the money. Regardless, the sky won't fall, and there will continue to be demand for good generic names, especially memorable names with traffic. That won't change until the Internet as we currently know it radically changes or ceases to exist," Olea concluded.

One thing Olea won't do is sit around and wait to see what happens. Just as he did while rising through the aviation ranks, he is taking a proactive approach to domains. "I'm active in the domain business every day," Olea affirmed. "I still look at and scan the drop lists almost every day that I can. I consider myself to be a 'working' domainer, but most days I enjoy what I do so it doesn't really feel like it's work. We recently went live with our own  brokerage website DomainSalesPlus.com. We're a very lean operation, just five of us right now."

"One of the highlights of my domain career was last year, when Frank Schilling asked me if I wanted to be an affiliated broker on his DomainNameSales.com platform. I happily accepted, and I've enjoyed working directly with clients on their world class sales platform since then. The platform is beautifully designed to provide the right tools to interact with and properly identify buyers. It also adds instant credibility when working with uneducated buyers or large companies," Olea noted.  

"The happiest change this year though is the addition of my oldest son Brian to the family business. Along with his very talented girlfriend Caitlin Carpenter, he's been working on some local initiatives, SEO, web 

Bob Olea and son Brian

design, and domain sales as well. It's great to finally have one of my kids in the family business! We also have a sales assistant and a web designer to round out the mix. Our office is in San Clemente, California, just a few miles from home."

"We're working on developing some of our own inventory right now, names like Oceanside.com, HomeRefinance.com and WirelessHeadphones.com. We plan to keep developing good and underutilized names for ourselves and others. It's always good to have multiple sources of revenue," Olea noted. "Our income is a mix of direct sales of our names, commissions, lease income, and parking. Affiliate and lead gen income will be a big focus for us going forward. We own some great lending names that will do well once developed, and we also have some legal names to work with. I feel that there's still a big disconnect between the affiliate/lead gen space and the domainer space. LOTS of opportunities there! Any domainer that has gone to a lead gen or affiliate conference would probably agree, although I've only ever seen a few at any of the ones that I've been to."

"One of the advantages of being lean is that you can quickly adjust as needed to take advantage of good opportunities. But for now it's an interesting time and I'm trying to just enjoy the moment. Life seems to move faster as you get older, and it's easy to lose sight of what's really important. For me - what drives it all though is my family, my only really good names - Trudie, Brian, Shelby and Alexander. Without them it just wouldn't be the same. And without Trudie holding down the fort I wouldn't be able to do even a fraction of what I do. Anybody with a loving and supportive wife understands this. It truly is one of the most important keys to success!," Olea declared.

The Olea family (L to R): Shelby, Alexander, Trudie, Brian and Bob

When asked to share some tips from his experience that might help others reach new heights in the domain business Olea came up with this list:

  • "Try to get involved and interact on a few domain forums. The only one that I'm active on right now is the private forum DomainBoardroom.com, run by long time domainer Donna Mahony. Loads of talent and respect over there - a great and fun group! Another forum that I would highly recommend is DNForum.com, run by Adam Dicker."

  • "Realize that the domain space is still a small world in some respects, and your reputation and network is vitally important. Guard your rep – it's way too hard to unburn the barn!"

  • "Watch the auctions and sales reports religiously! Real world current market intel creates a strong foundational knowledge of the domain space. And sometimes - when it feels 'right' - jump in! Some of my best domain decisions were made in a moment, based on a gut feeling. But they were (usually) backed up with a bit of knowledge and some experience."

  • "Try establishing a daily routine. Most of the other working domainers that I know have a set of tasks that they work on EVERY DAY! For some it may be scanning drop lists. For others it's trolling the auction marketplaces. Some are happy to just sit back and let the world come to them. Regardless of what your routine is – you need one. You'll find that over time it will evolve and usually for the better."

  • "Read EVERYTHING that you can before investing any significant amount of money. Like most things in life, there's a bit of a learning curve, and most domainers have tripped a few times before they figure out what works."

  • "Above all – try to have a little bit of fun with it! Life is short, and it shouldn't feel so much like 'work'! If it does - you might be in the wrong business! Domainers are typically a fun and very talented group of entrepreneurs. So many stories and interesting connections! Reach out and try connecting with a few people in the space. I promise that if you go out of your comfort zone you'll usually find a few unexpected connections!"

While Olea would be considered a major success by anyone's standards he said, "I still don't  consider myself to be a big success yet - at least not on the same level as some of the other brilliant people that have graced your stories over the years. But I've never really measured success by the thickness of my wallet either. I'd rather be happy and live an interesting life. So I guess that I'm successful in that way more than any other."

"I'm happy just to be in the game, steadily working in my small corner of the domain sandbox. I work at it every day, and I feel like I get better at 'The Domain Game' every year.

Bob & Trudie Olea

I hear that same comment from other domainers that steadily keep at it as well. It's a process and some 'Get It' sooner than others," Olea noted before closing with this final bit of good advice - "I always try to help people in the business when I can, fully realizing that others have helped me along the way. It's a good thing to give back to the community when you can. That kind of help creates unexpected and interesting opportunities as well!"


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