California man mysteriously seems to jet off on around-the-world adventure: Part 1

Chris Smith’s family says they received emails in 2010 saying he had made an agreement with his business partner to sell his part of their company, and then he took off.
9:22 | 01/25/20

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Transcript for California man mysteriously seems to jet off on around-the-world adventure: Part 1
Chris Smith was a real surfer. He dedicated his life to this. And he loved it. Chris was tall, dark, and handsome. Women were drawn to him. Very all-American, surfer/business casual, professional guy. Chris grew up in watsonville, California, which is outside of the beach town Santa Cruz. It was a place where he got really into things like wakeboarding and surfing. A good place for a guy who was athletic and liked to do stuff outdoors. I don't know many brothers that are as -- were as close as we just had a unique bond. Ever since I was really little, he felt like he was there to protect me, to provide for me. Were he and Paul always as close as they were towards -- you know, the later years? Always. Always, they're just the best of friends. We had just a great childhood. You know, my dad was a firefighter. My mom was a preschoolteacher. We lived on a private ski lake, so we grew up water skiing and wakeboarding. Chris Smith. Chris wasn't a gifted student. He was dyslexic but devilishly smart. Where he really excelled was in sports, and especially water sports. Chris was almost like an adrenaline junkie. He had more of a drive than anybody else out on the lake. Chris was known for his audacious tricks. He would try things that other people thought were simply too dangerous, and it was doing one of those tricks that he blew out his Achilles tendon, and that was it for his pro wakeboarding career. The water was his source of relief. He loved to surf, loved to be at the beach. He was a lot of fun. I felt like he was always the life of the party. Like, people just gravitated towards him. He was always full of adventure. If you think about Chris Smith, you got to remember, he loved the ocean, loved action, loved beautiful cars. So he had that sort of quest for adrenaline. He liked that. Thrived on that. Outwardly he was the jock, the surfer, the extreme sports guy. He looked the part. He just sort of fit that stereotype of the beach guy. But his friends say that he always had ambitions, he had plans. He was very passionate about what he did, but he was very interested in being successful and making money. He wanted it all. His dreams involved, you know, having a good amount of cash. And so he was striving for to be able to travel the world, to be very successful in business. Chris Smith is doing great. He's living in Orange county. He's got an apartment in Laguna beach. Orange county attracts very wealthy people. Rich people, famous people, just south of Los Angeles. A lot of the movie stars, a lot of the famous athletes wind up moving to Orange county, particularly in the area that Chris lived in. Beautiful houses, beautiful boats, beautiful cars, all of that. He's driving a range rover. He's surfing whenever he wants. He's encountered great business success in the lead generation business. Debt 10,000 offers services to get you out of debt fast. Chris becomes involved in this extremely lucrative part of the advertising and marketing industry that sells sales leads from people calling into 800 numbers. And he teams up with a man named Ed shin, another young, promising entrepreneur, and together they form a company called the 800xchange. 800xchange got to be very successful. They reached a point where they were making millions of dollars. After years of that free-spirited beach-guy lifestyle of chasing waves and beautiful women, well, guess what happens? Chris meets perhaps the one. A wonderful woman named Erica, and she seemed to fill every void when it came to romance. Tell me about his girlfriend, Erika. She was sweet. Yeah, I was looking forward to having her as a sister-in-law. Did it seem like it was serious? Yeah, I could tell that he really liked her. And he had expressed to me that, you know, he was thinking about getting even more serious, in terms of proposing to her. So I knew he really liked her. She had said then she just loved him so much, and he had told his father he loved her. Did you think that, you know, he may propose? We did. We thought he was. He was talking about it. You know, if you looked at Chris from the outside, you would see this hunky guy living in beautiful southern California who has this incredibly lucrative job, this beautiful ballet dancer with dazzling green eyes as a girlfriend. And you think, he has it all. But there were signs of stress. The company that he had founded with Ed shin, it starts to look like it could be in jeopardy. Chris was always talking to his friends about, hey, we should go. We should quit all this. He had visions of these faraway places and that he could live a simpler life there. If you knew Chris, you would know about how he believed in conspiracy theories and certain things. He was, like, anti-government and taxes. Like, we shouldn't pay taxes, that kind of thing. He wanted to make it big so that he could cut out. He was quite dissatisfied in many ways with the modern world. It looks like 32-year-old Chris Smith finally makes the decision to do just that -- sever all ties and just get off the grid. Chris emails his family telling them that he and Ed met and they reached an agreement. Ed had bought him out of his share of the company they founded, 800xchange. Everyone knew that Chris was a free spirit and that he wanted adventure. But it was a little bit surprising when suddenly, unannounced, they find out through emails that Chris is off the grid. He's leased a yacht. He's gone on a world traveling adventure. But nobody knew about it until they got these sudden emails. Monday June 7, 2010. I'm going on a vacation. Probably three-week trip to galapagos and Costa Rica. Love you too. It made total sense to you that Chris would just up and leave it all? Yeah. I remember him in the kitchen saying, I'm so over all of it, I'm just gonna be done. I'm gonna go be a bartender on the beach. Amazing sailing for the past two weeks. There's no internet or phones. Just us and the sea. Every surfer has this dream of sailing off into the sunset with a bunch a money and a beautiful woman. In this case, the problem is it was not Erika. Chris sends Paul an email, and attached to it is a picture of his traveling companion, and she is stunning. She's former playboy playmate, Tiffany Taylor. This may seem like Chris' dream trip, but it's nothing but a nightmare for Erika. So through a message from Chris, she learns she's been tossed overboard. You know, most people would be like, a playboy playmate? Come on. But Chris was good-looking enough. Yeah. Wealthy enough that that actually made total sense. Yep. I remember I got one e-mail from, and she was really mad. She was like what the -- is going on? Is he bipolar? I said, no, sometimes he just needed to get away. There's only my friend and me and the crew. I miss you guys too. I see things so much more clearly now because I've unplugged myself of that crazy society and fast lane, something I should have done so much sooner. She was saying, I'm headed to Peru. I'm going travel a bit. And I remember saying, wow, I love you. Take pics. Have a great time. I'll be home probably around early to mid-august. Want to get up to buenos aires if possible. The seas are choppy, sometimes smooth. At first Chris said that this trip would last a couple of weeks. Those weeks turned into months. And suddenly he's on this sort of around the world epic Hey guys, I just finally docked in ushuaia, a port in Argentina. We have 20 to 25 islands to explore. The question as these emails develop are, is he running to something or is he running away from something? Because as time went on, originally it looked like he just needed a break. And then the emails started to look like he might have been

This transcript has been automatically generated and may not be 100% accurate.

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