
Uncomfortable with Jeffrey Gabriel
The Uncomfortable Podcast
Nobody ever succeeded by coasting in their comfort zone.
Hosted by Jeffrey Gabriel, Founder & CEO of Saw.com, the Uncomfortable Podcast has a the simple mission - encouraging more professionals to take a step out of their comfort zone so they can thrive (not just survive!) in the modern working world.
Through open and, insightful conversations with business owners, industry experts and thought leaders, the podcast will shares stories, tips secrets and strategies from people who’ve been there, done it and got the t-shirt when it comes to achieving the extraordinary results.
Always unscripted. Always unfiltered. Always Uncomfortable.
About your host, Jeffrey Gabriel:
Jeffrey Gabriel is one of the world’s leading domain brokers, contributing over $500m in domain sales and previously holding the Guinness World Record for highest domain sale of a .com (sex for $13m) and a .org (poker for $1m) as well as Ai.com in a multi-million dollar deal.
He wholeheartedly believes that in order to succeed in business, you need to take a permanent step outside of your comfort zone. And that’s exactly what he did in 2019 when he left a well-paying dream job in the Cayman Islands as VP of Sales at Uniregistry to start his own company, Saw.com.
Since then, he’s seen plenty of success, but also his fair share of failure. He’s won clients. He’s lost clients. He’s closed deals. He’s missed deals. He’s hired people. He’s fired people. He’s been liked. He’s been disliked. But, throughout his life, he’s always made a conscious effort to keep trying new things that make him ‘uncomfortable’.
Uncomfortable with Jeffrey Gabriel
A Solo Special - Jeffrey's Story | Saw.com
Join us on the podcast as we unravel the intriguing journey of Jeffrey Gabriel, a man whose career path was anything but ordinary. From a lackluster college graduate with no clear direction, Jeffrey ventured into the world of sales, starting out as a novice selling mortgages. He quickly ascended to become a top salesperson at his firm, before pivoting to a role that had him driving across New England, pitching to human resources professionals in his trusty 1997 Ford Ranger.
The economic crash of 2009 upended his career, leaving him jobless and uncertain of his next steps. It was during this tumultuous time that Jeffrey stumbled into the domain selling business. Within just two years, he had sold millions of dollars in domains, including the record-breaking $13 million sale of Sex.com, a feat that landed him in the Guinness Book of World Records.
Jeffrey's story doesn’t stop there. He later moved to the Cayman Islands, where he built a formidable sales team and led an industry-leading domain brokerage, generating over $500 million in sales. Despite his monumental success, Jeffrey chose to leave it all behind to chase his own entrepreneurial dreams.
Tune in to hear how Jeffrey Gabriel navigated the highs and lows of his remarkable career journey. This episode promises to be a wild ride, packed with lessons on resilience, reinvention, and the relentless pursuit of one’s dreams.
About Jeffrey:
Jeffrey M. Gabriel is the founder of Saw.com, a boutique brokerage that specializes in acquiring, selling, and appraising domains. With over 14 years of experience in the domain industry, Jeffrey has a proven track record of closing multimillion-dollar deals and delivering exceptional value to his clients.
Jeffrey's core competencies include remote team management, online marketing, and strategy. He is passionate about helping businesses and individuals achieve their online goals and dreams. He has been involved in some of the most notable domain sales in history, such as Ai.com, Sex.com, and Poker.org. He is also a Guinness World Record holder and a frequent speaker and writer on domain-related topics.
Follow us on social media:
Facebook: https://www.facebook.com/sawcom/
LinkedIn: https://www.linkedin.com/company/saw-com/
Twitter: https://twitter.com/sawsells
Today on the Uncomfortable Podcast. You got me as your guest telling my story, my struggles and a little bit of what I've learned along the way Giddy up. So I'm going to start kind of like one of my guests in Mark Huba, where we kind of go over his life and kind of go through the trials and tribulations and ending up in the domain industry and where I'm kind of sitting today and you know I'm going to skip over some parts of my life that might not be relevant to this show, but you know I'm going to start around the college time. I will say I was never a great student. I always found myself in trouble but I was never like fighting or rude to teachers. It was just I couldn't keep my mouth shut. I wasn't extremely focused all the time and I think the material that I learned in high school mostly, and a big portion at least to the first half of college I always felt that it had no meaning to me and it didn't really matter. Like I didn't really care that much about physics. I liked history because I found it to be interesting and you can always learn from the past. Mathematics the basics, weren't interesting to me. They got interesting when I started getting into finance and learning what makes a stock price change, learning about money, learning about things that mattered. That's when my brain started to turn on and I got better as school went on. But as a high school student I was usually in trouble because of my grades, because of talking in class. I was stuck sitting in the front row.
Speaker 1:But I did graduate and went to college. I actually wanted to go to college to become kind of like a radio DJ or a shock jock. I used to love listening to Howard Stern and these other guys on different radio stations. I even was an intern at a radio station when I was a senior in high school, but anyways. So I graduated college with a degree in finance and risk management and, I believe, a minor in communications. I get out of school I'm not sure exactly what I want to do yet, but there certainly was discussions in my family and I grew up with a great childhood with a lot of friends, a lot of fun times, supportive parents, supportive family. I had all four grandparents until after I graduated college, who I was close to each of them and getting older you realize how lucky I was to have that. Most of my friends and even my kids don't have their grandparents around as much because we live far away.
Speaker 1:But yeah, so I graduated college and I actually started working at a warehouse because I couldn't really find much work or I wasn't really sure what I wanted to do. And it was a little disappointing because I heard like different friends had these awesome jobs in New York or in Boston or working at financial institutions like Fidelity. I remember this guy, bill, who's a very good friend of mine, and also Anthony were working at Fidelity and I think Bill at the time and this is 2002, was making like $25 an hour and I thought if I can make $25 an hour I would be set for life. And that's when I was working at the warehouse. But there was know, there was a little bit. In my family are some lawyers and my dad's a lawyer and his brother is a lawyer and his dad was a lawyer and his dad's brother was a lawyer. So there was a little bit of pressure on me to also go to law school. But you know there was discussions of it and I took the LSAT to get into law school.
Speaker 1:I ended up getting into law school, but during that time I actually also started selling loans, mortgages, and when you're 22, 23 years old, in your first sales job, after leaving the warehouse and you start making some good paychecks. And then the summer is ending and you're supposed to be starting law school in September. I didn't want to go. My dad said, well, you can go to law school at night and you can work during the day. And I was working during the day, making good money and going out with my friends, and I just knew at the time in my life that I probably wouldn't be focused on law school and that to me seemed like another one of those situations that I was in in high school where the material was not something that was ultimately important, that would stick in my brain and I would not be able to learn it that easily. I'd have to force myself, and to have to do that through, I believe, three years of law school would probably end in failure. So I had the tough discussion with my dad. He said, well, what are you going to do? And I said, well, I'm going to sell loans and see how it goes. He was a real estate lawyer and he actually got me into it. He didn't get me the job, but he said you should go sell mortgages, and I got a job right out of the newspaper working at a mortgage company in Worcester Mass and did that and then ended up working with working. You kind of bounce around a little bit more looking for better splits and things of that nature. So I did that for a number of years.
Speaker 1:What I loved about it and I realized about sales in general which there's certain parts of sales that I enjoy and there's different types of sales and what made me excel in mortgages was I really like talking to people and it's something everybody says when they say they like sales but I like hearing their stories, just like I'm doing on this podcast today. Hearing a doctor what kind of doctor? Oh, why are you that kind of doctor? Or a construction guy what do you specialize in? And then hearing about what they're trying to accomplish, whether it's a refinance, to take money out to put on an addition or pay for a kid's college or pay off debt or buy a dream house or buy a second home, and you're learning about also, what are they really making, how much money are they really making? And it opened my eyes to the world as to how much money people made, how much they saved and what their situations were credit-wise. And then I learned also how do you fix credit? How do you approach the agencies if there's a mistake? How do you approach the agencies even if there isn't a mistake and you're hoping they don't respond? How do you approach the agencies if you owe money to a defunct company and help someone's credit?
Speaker 1:There's a lot of things to do with mortgages and working at a few different places. You get into this situation where the mortgage company will always advertise the lowest rate possible on a 30-year fix at least where I lived, in the newspaper or in other places online, and then that gets the phone to ring and the moment you pick up the phone, all it is is what's your interest rate and what does it cost to get it? And now what you're doing doesn't really matter. And I learned one of my first things in sales was it wasn't always about the rate and it isn't always about the cost. You can kind of twist things. It's about payment. What I sold based on payment and I also sold based on other value propositions, like I would give everybody a free home equity line who did a refinance with me. I even got to a point where people would be referred to me as the guy who would get the free home equity line. But everyone could sell or give a free home equity line. It was a very simple thing to do.
Speaker 1:I also learned that in sales that if you want to be good at what you do in sales and any job in sales is you have to use the resources around you to make you great. And what does that mean? Well, you know, when you talk to the old, grizzled guy who's been doing it for 20 years, you should probably listen to what he has to say as to what he does, his process, how things should work. That's all very important, you know. There's also, on the other hand, understanding the guidelines and the requirements that different banks have to approve loans, and you start to figure out what banks like. Different flavors of people, those with bad credit, those who are self-employed, those that just started a new business All of those different things can make your life a lot easier. And just understanding the process I've done the same in domain names is understanding every single facet and then taking it a step further, meeting and knowing the vendors and the players in the space. So same with the demand space is that I know all the different vendors. I know the different people that sell different domains that sell, and understand how different registrars work, how the registries work. I go to the ICANN conferences.
Speaker 1:When I was selling mortgages I would read the guidelines. I would actually call and talk to some of the underwriters. I would get to know they had account reps that used to come into the office so you'd talk to them about types of loans they want and so whenever somebody calls in and they have a situation that's outside of the box, you are prepared and a big part of sales isn't necessarily selling, it's about providing solutions to a problem that somebody has. So when they come to you and they say, hey, I want this and it's not normal like maybe it's a mixed-use property, meaning that they want to live on the top floor and their store is on the bottom floor, or they live in an earthquake zone or a flood zone or they have some other problem with the property you can immediately know without a doubt and saying and talking to them intelligently about what's happening. This happens regularly in the domain business and some people think that being a domain broker is very easy.
Speaker 1:Being a loan officer can be very easy and same with. Being a domain broker can be an easy job if you wanna be really bad at it, but if you challenge yourself to understand the market, to understand what's happening, to know all of the vendors, to know what all is happening, that's what I did as a loan officer in my first job. It took time I mean, it wasn't like minutes that I figured this out, but that's what I did figure out. And after doing that for a number of years I realized that this might not be something that I want to do my entire life. And while I was doing this, while I was selling loans and doing this, you know, I kind of had this entrepreneurial itch and I remember buying some book that was talking about how to start a business and making a business plan and doing all these things. I actually had these big poster boards on the wall in my room that I had this idea for selling mortgage leads online and people would click on the ads and mortgage companies would pay money for the clicks. Brilliant idea. That was already thought of. I didn't realize that PPC advertising was already happening in the early 2000s. But that was something that I already thought of. I didn't realize that PPC advertising was already happening in the early 2000s, but that was something that I was thinking about.
Speaker 1:Anyways, I ended up leaving the mortgage business and I joined a company called JobFox. Jobfox is similar to like a monstercom or career builder, and what I would do is it's usually with a lot of these job websites is they advertise to candidates. So if you look for a job, you go and you put your resume on there for free and then people like me will sell access to the database to companies. And if you don't realize this, like a hospital for example, they always need nurses and if they're going to pay a headhunting firm to find a specific nurse a lot of the times a nurse the expense for a nurse is one year's salary for a headhunter to get a nurse for you, which is a lot of money. So when you walk into a company and you say, hey, we have a database of nurses of different skills and abilities and they're fresh, these are people that put their resumes in recently, you know all they had to do is get one or two placements off of our product and that would pay for the service for a year.
Speaker 1:So my job at JobFox was cold calling all day into HR departments, to small businesses, large businesses I mean from Staples to a small nonprofit in Worcester, mass, and driving around really New England, with my projector in my 1997 Ford Ranger. And so I would cold call my way in. I would hit the road, go do a presentation, bring donuts, coffee, beer, whatever if it was on a Friday, sandwiches go in there, set up a projector and do a presentation, and you know it's funny with over 100 salespeople. After being there a while and when I was hired, I was one of the few people that didn't have experience in the job board space, but I fought my way up to being number two and again I applied the same logic. I got to sit next to a gentleman that was in the job board space, who worked at Monster for a number of years, and I picked his brain. I try to understand calling in and institutional selling, because institutional selling and decision-making process is much different than talking to a guy and his wife about buying their first home and the decision-making process and much different than talking to a guy and his wife about buying their first home and the decision-making process and how they go about it. Right, yeah, and I became number two out of about a hundred salespeople. I know I was beaten by someone who worked in the New York city area and all she had to do was either take the subway or walk to her appointments, where sometimes I'd be in Rhode Island in the morning and New Hampshire in the afternoon. It would burn my whole day I'd be on the road. So, anyways, but again, as long as I could learn every aspect of the sales process, the industry and understanding recruiting of these companies wanted and all these things, it became a lot easier for me to go in there and just have frank conversations.
Speaker 1:And at first I had, oh, the company gave us this like 20 slide PowerPoint presentation and it was. It was like it was nicely done and it was professional, but it was extremely long and I knew like halfway through I'd be losing the crowd. I mean, I remember one time I was doing this presentation to a college and I looked out into the crowd. And I mean, I remember one time I was doing this presentation to a college and I looked out into the crowd and there was a woman who was asleep and I realized that I needed to make a change and that this presentation wasn't me and I cut it down to like eight or nine slides and changed them quite a bit. And when I did that and made it more of an interactive presentation, my conversions went up and through the roof.
Speaker 1:And, strangely enough, one of the days, like so, I was doing really well and it started to catch attention of some of the upper management and they're based in Washington DC and they wanted to know, like you know, what I was doing and they talked to me about it. And one of the days I went with the one of the C-level guys out for a sales meeting and I was working so hard to get this meeting for so long and I was debating should I do their presentation or mine. And because I worked so long to get the appointment, I knew that their presentation would probably be boring and I was on practice with it at this point. So I decided you know what, what the hell, I'm just going to do mine. And I did it anyway. And um, needless to say, he wasn't impressed. We had to talk about it, um and um. But it worked out. I got the deal, but in um. So I went from being, uh, you know, the top of the company in March of, I would say, 2008. Then, by the end of 2008, because we went down to Atlanta for a sales meeting around then and that's when I got the award.
Speaker 1:And then, by the fall of 2008, the market crashed and I don't know if some of you folks remember this, but Lehman Brothers crashed. Washington Mutual, who I used to get my home equity lines from, crashed. We sell this other product called an option arm from Washington Mutual. That bank collapsed and Bank of America bought them. Lehman Brothers went under. I think Merrill Lynch ended up as part of Bank of America as well, and it became very obvious that when the market was crashing, that my company probably wasn't going to last either, and it went from being a very large company with VC funding and everything looking like it was going in the right direction to us going to work and nobody answering the phones.
Speaker 1:And it turned into us actually driving around to these technology parks that are in the Boston area and knocking on doors and asking them if they wanted to buy our services or if they're interested, and pretty much getting laughed at. And it ended up resulting in us pretty much calling early days and going to the pub and having some drinks and really just waiting for that time to happen. And one day I got an email that at it was like 10 or 11 o'clock we were going to have a meeting and the CEO was going to talk to happen. And one day I got an email that at it was like 10 or 11 o'clock, we were going to have a meeting and the CEO was going to talk to us. And before the meeting I called my buddy, dave, and I said I think I'm going to get laid off here. And he said well, I got two tickets to Celtics, knicks and I'm like almost courtside they were like one behind courtside. He got them from a client or somebody he goes. So if you get laid off, let me know why don't you come down to New York? So we sit in the meeting and then the CEO his name was Rob McGovern, was actually the person who created CareerBuilder. It was a very intelligent, great CEO, very calculated, polished, knew his space. I would definitely do business with him again Gave us the bad news that the company wasn't doing well.
Speaker 1:They gave us a decent severance and gave us as much as they could and I went on my way. So I left there. I headed straight to New York. I was there and things got really grim really fast. I remember sitting at home and at the time my wife she was my girlfriend was moved in with me and I remember sitting in my bathrobe like really trying to get a job for hours every day. Between that and playing Zelda I started, you know, just really working hard to apply for jobs. I felt worthless. I remember calling in and being told oh yeah, we have a great outside sales job for you. Then going in for the interview and they're like oh, we changed our mind. We want you to do lead gen. If you don't know what lead gen is, it means you just bang the phone all day and if you get someone who wants to bite then you transfer the call to the real salesperson.
Speaker 1:And after what I've been able to accomplish and what I've been able to do, there was no way I was going to do that. But that was really the only thing that was nibbling and that went on for a number of months of just banging my head against the wall, really just feeling not very good. I actually rototilled or cultivated some people's gardens because it was the springtime to make some money doing some landscaping, trying to make it happen. But I knew that as hard as if I just kept trying hard that, no matter what happens in the market, great salespeople are always needed, and you know it was grim. So, anyways, I went back and I thought about it and I said to myself I need to think more strategically about how I'm going to get this job or how am I going to get a new opportunity.
Speaker 1:I went back and went over a list of companies that when I was at JobFox, that I tried to sell into or I sold to, and then I just started calling them and saying hey, I came into your office, I did a presentation you know I cold called in. You know I don't mind getting on the phone. I presented myself well, do you have any sales jobs open? And I got a lot of nibbles that way, and one of them was Cito, and Cito gave me a chance. The problem with Cito was it was over an hour and a half away from my house. I lived in Worcester, massachusetts. Cito is based in Cambridge, but I was delighted to get it. They gave me a waitress's salary I think it was about $20,000 a year and a percentage of any sale I could get. And in reality I even told them at the interview what you're offering me is actually less than I'm making on unemployment, but I want to. I think I can do this. I'm excited about this.
Speaker 1:I read about domains and I was like I'm doing this, I'm going all in. So I started there in May of 2009. After the long weekend, I always mix it up with Memorial Day and Labor Day I think it's Memorial Day and so June was like my first full month there, but I was kind of training. I did like a week in May and then training. In June. I sold my first domain called work Zilla. Looks like a developed company now. I sold it to a mark who was brother Funny enough, we also share the same birthday and then in July I sold 770. I sold actually more than that. I sold servercom for 770,000.
Speaker 1:I sold omgcom to Yahoo and did a significant amount of money. I think I did over a million bucks in sales my first month in it. The following month I sold some other names. That equaled a few hundred thousand dollars and when I spoke to my boss there she said she thought it was a fluke. By the end of that year I sold the highestorg sale ever pokerorg for a million bucks.
Speaker 1:And what I did again let's go back to the recipe is. I got to sit with people like Matt Rosebrook, who is now a broker, at Afternoon Go Daddy. He helped teach me a ton about the business. I picked his brain constantly. There were others there, like Jay Finnan and Tessa Holcomb obviously as well. She was there just asking a lot of questions and then talking to the customers, the sellers. There were others there, like Jay Finnan and Tessa Holcomb obviously as well. She was there just asking a lot of questions and then talking to the customers, the sellers, really getting to know them, and then attending different conferences.
Speaker 1:And then, while I was there, I was given the opportunity to take sexcom on to sell and that was a very huge challenge because the expectations of the price of the domain were extremely high. But back in, at this point in time, it was uh, 2000,. Uh, it was July in 2010 when I was given the opportunity to sell uh, sexcom and um, when I was given the opportunity to sell sexcom. And or was it 2000, july 2009. I don't, I don't remember July. I think it was July 2010.
Speaker 1:I was given the opportunity to sell sexcom and people told me in the industry I go to a conference, talk to people about it Like good luck. There's no way you're going to sell this for that price. Might be worth three or five million dollars or whatever it is. And it was additionally challenging because people in the adult business a lot of the time say they work for advertising companies. And not only do they say they work for advertising companies. When you call into these advertising companies, a lot of the time they don't use their real names, and it makes sense that they do that.
Speaker 1:But it was challenging getting a hold of people in the adult business to try to sell the domain to them and also got a lot of hate email and stuff from people who were against it, which was surprising. But I stuck with it worked extremely hard. I remember coming down to the wire and we actually had somebody who offered more than the 13 million. He, I believe, offered 15 or 16 million for it, but it was over a period of time and the court wanted cash. They want to pay off all the debt when something's in, because sexcom was in bankruptcy. So when something is in bankruptcy, the job of the court is to pay off all the people that are owed money. It's not to get necessarily the best price, because the best terms was the cash. I think if I owned it outright I would have taken the payment plan, but anyways, at that point in time the adult business was still paying extremely well and the tube sites hadn't killed the revenue on it yet, so we were able to get a good price for that.
Speaker 1:I made that sale and there's not many companies that would give a guy like me a chance just to get in the business and get that job and then give me the opportunity to break a world record. And you know, ceto will obviously have a special place in my heart. But I also knew working there that if I still work there today I would have the exact same job I had as when I started. It just didn't seem like there was much of a path for me to grow as a professional and a salesperson and that entrepreneurial spirit that has always itched me kind of remained. And it wasn't like they promised me anything when I started working there. The job was to be a broker, and so I don't slight them for that. It's all positive things that I can say about them and again I'm very grateful for the opportunity.
Speaker 1:But I decided to leave and I started Domain Advisors, which became igloocom, with Tessa Holcomb and Greg McNair. Tessa has been a domain broker probably a year longer than me in the domain industry. We hit it off at CETO and she's a great salesperson. And then Greg we call him Triple G. Greg McNair has been in the traffic side of the business. He's a serial entrepreneur. When I met him he was growing tuna in a fish tank in Spain. Last time I spoke to him. He's been working on solar and he's always been in real estate Working with him and Tessa. I got to say that I pretty much got a master's in business over the time that I was with them. Just the whole, starting from absolute zero, from not even having email addresses to getting a website, going to hiring people, having them work for us, payroll, keeping the books, doing those things, traveling as a business owner. And you know from Greg being really I mean, he's an entrepreneur, but I have to say he's one of the best business development people I've ever met in my life. He's very good at just walking into a room, meeting people, being memorable, putting deals together, and I learned a lot from him from there and at the time with domain advisors, slash Igloo.
Speaker 1:We also had Brooke Hernandez, who's is working with me now at Sauce. She came along from the commercial real estate business. You can hear more of her story. I interviewed her a couple of months ago. We had Amanda Waltz, who I started Sotarcom with, but her and I kind of split up. And Christina Auckland was another salesperson, and then another person named Gina Aubrey who worked for us. So we used to call them Jeffrey's Angels because it was me and a group of women that were selling and I learned a lot from them.
Speaker 1:And one of our customers at the company was Frank Schilling, and Frank, if you don't know him, was one of the more famous domain investors in our industry and he owns about 350,000 at the time 350, 350 or 360,000 domains and his right-hand man, vern Jurevic. They grew up together, they were good friends and him and I became friendly at the shows. We spoke to them and they actually hired Dan Adamson, who I worked with at Uniregistry for seven years, but I'll get to him in a few minutes. So, anyways, they were a client of ours and what they would do was is that we were doing brokerage, we would be selling domain portfolios, we were selling exclusive big names, we would be have sales landers have opportunities coming in. We actually had a what the hell is it called A like an email list where we do a newsletter with domains on it and and business was going well and I was pretty happy at the time.
Speaker 1:I lived down the Cape, right near the beach on a beautiful golf course in Cape Cod and New Seabury. Life was good. The business was going in the right direction. I really liked working with Tessa and Greg and the other women, and what would happen on a daily basis would be that Frank hired Dan Adamson and a woman named Maureen, and Frank's portfolio was generating about 1,000 inquiries a day and they couldn't really keep up with them and at the time they didn't really even have a CRM, and so Vern would send us all of the old leads that they would respond to or they didn't go anywhere and we would work on those. And we also got to put our phone number on the landers, so we would get a lot of opportunities from there and going to look for his own feed and he got his own and he started internet traffic, but he hadn't launched domain name sales yet. So I ended up talking with Vern and Roy was one of the developers and Dan and helped them design the beginnings of domain name sales.
Speaker 1:And then it kind of got to a point where Frank is seeing parking earnings going down and because there was a period of time that he wasn't interested in selling really any of his names because the parking payouts were so high. But now the parking payouts were going down and he saw an opportunity in making more sales. And so he called me one day and he said you know, I think you and your team are doing a great job and you know, obviously I'm a client of yours, but I think it would be better if we did this together and it wasn't, you know, just me as a client. And he asked if I could fly down and came in and talk to him and Dan Adamson was there at the time, and so I flew down there. He asked me to go that day. I think I was. I remember I was shaving and he asked me if I could go down that day and I said how about tomorrow?
Speaker 1:So I flew down the following day, looked around the island, went in his office and we talked and he said how would you like to come down here and build up the team and really ramp this up and grab my portfolio by the horns and really turn this into a machine. He had developers sitting there in the office. He wanted me to hire brokers. He wanted me to really use the technology to add my book of business, of sellers and domainers to the platform and really turn up the heat. And I remember calling my wife at the time we were married at this point, no kids though and said I'm torn I really love working with Greg, I like working with Tessa and the girls, and we've done a lot. But I feel like if this doesn't work out with Frank, I can go back and I can start another brokerage. But I don't think an opportunity like this is ever going to present itself again in my life, especially getting to live abroad, on a beautiful island, you know, with a guy that really is excited about accomplishing goals. He had plans for the registrar. He was the GTLDs were. You know the application process was going on. You know he had it. It was all happening over there and there was just a lot of action and he had the developers and he had the money and he had the desire. And, um, I said you know what, fuck it. So I told Melissa I think you know Frank and I made a deal. I told Melissa, like you know you're going to, I think we got to move, and she didn't even go to Cayman once, so, sight unseen, uh, we packed everything up and um and move there. So I was there like mid-December. I was there January 3rd the following year in 2013.
Speaker 1:Working at Uniregistry when I got there, it was domain name sales and internet traffic at the time was interesting. You know, what I love about it is the startup feel, where it's not as everything isn't so established, like we didn't have an HR department, we didn't have, you know, all these different things and people. It was more like a fleet, free flowing ideas, with a person who is truly passionate about the business, and that is the kind of environment that I really love and that we can try new things and you know everybody's on board to achieve these goals and trying new things and trying little things and big things, and if they bomb, it's okay, and it was a really exciting time. And then getting to start to hire salespeople, putting together trainings and shipping them down there or hiring from the island was great, you know, yeah, and my goal there, which was extremely challenging, was I had to sell, no matter what, a million dollars a month, come hell or high water. And it wasn't just me, obviously, but it was myself, dan Adamson, a group of salespeople. There was about four salespeople. So really we had to hit that number every single month, come hell or high water. We had to find a way, and the best analogy that I can give you is it's like putting on a massive like show, like a circus, every month to just try to get it in down to the wire and then it, you start at zero again and Frank is on you to hit that number.
Speaker 1:You know, and to get there we obviously tried to hire and retain the best talent. We tried to train them the best we could in just sales in general in the industry, trying to share my idea of like knowing everything you possibly can. We had to pay them well to stick around and to live in Cayman. It wasn't cheap, you know. We needed to work on commission structures and different strategies, and then we had sellers, like other sellers, joining us and then trying to separate the work between different brokers, like who's going to work on Frank's stuff, who's going to work on our customers things? Because you know, let's be honest here when Frank sold the domain, he did pay into domain name sales and uniregistry to make payroll, but he got 85% of what he sold versus we would get 15% if we sold something for a customer. So just think of the difference in revenue. Like you sell a million dollars for customers and a million dollars for Frank, you know you get 150k from there and he gets 850 from himself and he also profits from that because the business was running at a surplus. You know that makes the most sense.
Speaker 1:But as time went on, the portfolio remember we did this for seven years got thinner and thinner and you know we weren't replacing many names on a regular basis, you know. So the job got a little harder. Now we did add better technology to do better with following up. You know we had a team that went over old leads. We had a thing that pulled phone numbers and we called them phone follow-up leads and the guys would call all the old leads over and over and over again. You know we really just rinsed it out and got more and more efficient with pricing and sharing the inventory all over the world and really getting it going and sharing the inventory all over the world and really getting it going and what I really liked about working for Frank was that was different than working with Greg is Frank really loves new ideas. He really has. That's where he gets excited, you know, and it could be even the littlest idea that changes something in some way or gives you a chance at making money.
Speaker 1:And we would make calculated decisions and talk about these ideas and go through them and design them and they'd come true and they would be released. And some of them worked quite well. Others bombed and when they bombed, frank frank didn't care. He'd want you to learn from it, because it might have cost him thousands of dollars or tens of thousands of dollars, like we made an affiliate program when he won all the um, the 20 gtlds. We made an affiliate program on parking that we thought would get a lot of registrants. It didn't get many, so we got rid of it. But that was. Building the affiliate program with the developers took a lot of resources, time, energy and money and it bombed and we just moved on from it where some other people can't let that go, and I think working with Frank that was a great thing that allowed us to try new things. He didn't want you to make the same mistake twice. God help you if you did, but he was definitely supportive of those things and that's what you know.
Speaker 1:I really loved about working there and we were able to roll out some really great products some different sales landers, different sales strategies. We built a payment plan product. You know. We did all kinds of different stuff, which was always exciting and there was always something going on at the company, built the company up to on my side of the business, built the brokerage and customer service to over 50. Dan Adamson, who helped me do this, and obviously there's you can't do this stuff alone. This isn't the Jeff Gabriel show. We did it with a lot of people who are part of this.
Speaker 1:Developers were a big part of our business. Obviously, frank was part of these conversations. We had different project managers and other people and designers helping and then obviously asking a lot of the salespeople what do you need? What do customers tell you they want? How can we build this better? What can make your life easier? How can you be more efficient? You know, talking in that way and then building the sales team up and customer service to over 50 people, which you know I managed for a period of time and Dan Adamson was at a point.
Speaker 1:He was from England, that he moved back, and so we opened an office in England, and so I would go back and forth to the English office and they would handle most of our European leads. So we would really have, you know, a 14 hour or 15 hours of people sitting at their desk answering the phones and the business was rolling. And you know, it was an experience, um, that I'll never forget, um, I think that my time there taught me an immense amount of about management, about myself, about sales, um, about empathy. I think having children makes you realize it's not all about you anymore either, and we had both of our children on the island. I made friends there that I'll have for a lifetime. I'm friends with Wade Smith, who works at GoDaddy, and Andrew Mathias and Vinny we're still friends, I still talk to him all the time Dan Kenny I'm friends with this other family called the Piers, who are there on the island. I made other friends with my friend Simon. I just go on and on and on. These are people that I met in Cayman that either I worked with or I didn't work with, that I've been friends with since and they're like family to me, but it came a time where things started to change at Uniregistry and in some ways the things that we invested in or Frank invested, in some ways the things that we invested in or Frank invested in, like the registrar and the GTLDs, didn't grow as much as was anticipated and the expenses to carry those things was immense.
Speaker 1:Looking at the books, you know, and, and honestly, having 50 salespeople and customer service and HR and all those different things to snacks and coffee and food and rent, you know, and parties and travel and conferences and sponsorships and marketing and all these other things, the weight of those expenses throughout the company became quite heavy. And you know, we did experience a round of layoffs. I had to let go a lot of people one day and that was a very stressful, hard day in my life, in my business career. But not just that, it's just the business changed and got much more corporate-y, which happens in the succession of a business, and I knew that it kind of got to a point that I did everything that I felt that I could do and I just felt like I was just going through the motions and it wasn't with the same excitement and energy and again I got that entrepreneurial itch. It hit me again. And so I started talking to my wife about it in probably about April that that was something that I wanted to do it and probably about April that that was something that I wanted to do.
Speaker 1:And around I got back from a conference in Portugal Cache Cache, I think it's called and I said I think it's time that I move on. I told my wife I've made the decision and so I called Frank. It was in the beginning of July. He didn't answer, he was on vacation. And then I ended up speaking to him. It was July 4th that I resigned and I gave plenty of notice to say that I was going to move on and do something else.
Speaker 1:And the moment I hung up the phone I just said what the fuck did I do to my wife? We had a beautiful house in Cayman, we had a life that people potentially would just absolutely love to have, and I gave it all away. And I said to my wife we might end up on my parents' couch eating a can of beans. And she said I support you. She said this is what you want to do. You know you want to go, do your own thing. You've always wanted to do your own thing and I think the time is now.
Speaker 1:You're 40. I just turned 40 in April. Well, I really turned 39. So sorry, I turned 39. She's like this is this is the time If you're going to do it in your life, you got to do it. So we sold the house. Well, we put the house on the market, we started selling all of our items, our materials, of possessions, and then my wife left the island to go, actually moved in with some friends back in Boston and I stayed behind to close up our affairs. Tune in next week for part two of my story, where I talk about moving home, readjusting to non-island life, launching sawcom, the lockdowns, overcoming countless challenges sleepless nights, self-doubt, a failing business, covid, technical issues, two children, a partridge in a pear tree and much more to find success on the other side of the rainbow.