How a Nerd Who Got His First Kiss at 21 Built a $30 Million ‘Sugar Daddy’ Dating Empire

How a Nerd Who Got His First Kiss at 21 Built a $30 Million ‘Sugar Daddy’ Dating Empire
Benny Luo
May 7, 2015

“Love is a concept invented by poor people.” – Brandon Wade

One of the best ways to create a great product is to simply come up with a solution for your own biggest problem.
For entrepreneur Brandon Wade, his problem was relationships. For a long time, he struggled to find a quality girlfriend. Desperate for an answer, he created is a dating site that pairs rich men aka “sugar daddies” with young, unestablished women aka “sugar babies.” The site essentially lets men pay for dates and relationships with women. The site has been so successful that it currently takes in $30 million a year in revenues.
While the site has experienced fast growth and tremendous success, it’s also aroused controversy by challenging the fine line between dating and prostitution. Wade told the Wall Street Journal:

“Because there is chemistry involved in these relationships. It’s not a one-time exchange of money for sex. Most people who meet on the site don’t have sex on the first date. After a relationship forms, sex becomes part of the relationship. It’s not very different from a rich husband or boyfriend giving money to a wife or girlfriend.”

Wade, now 45, considered himself a nerd in high school. He won multiple science fairs and math olympiads in his home country of Singapore. He went to an all-boys school up until the 10th grade, an experience he says greatly hindered his experience with women:

“In 11th grade, I wanted to approach this girl at school that was so beautiful, I didn’t know how to do it. I was reading a book about shyness and talking to my dad about it. He said, ‘You have a fundamental problem. You are afraid of making a fool of yourself. So just do it! If you make a fool of yourself, you are a fool already, so you don’t have to be afraid of it.’

It seemed so logical at that time, so I approached her one morning after practicing what I was going to say. I was gonna walk up to her and say, ‘Listen, I’m very shy, and I don’t do this normally, but I really like you,’ so something very sort of natural, but instead I paced the school cafeteria and eventually I walked up to her and I tripped and fell. I stepped on her foot as I was standing up. I then blurted out ‘I’m shy.’ The rest of it just went to hell. She was laughing the whole way. Ever since that day, I just avoided her every time I saw her at school, because it just reminded me what a bloody fool I was.”

Brandon representing Singapore at the International Science Fair in Sydney Australia.
Seeing that his father’s advice didn’t work, he consulted his mother, who said:

”Just focus on school and study hard. Someday you’ll be successful, and all the girls will be there, so don’t worry.”

With that in mind, Wade continued working hard and eventually went to MIT for college. At 21, he got his first kiss from his then-girlfriend.

“She was from Malaysia. So she was from sort of where I was from. We started as friends. We would hang out a lot. She was here over the summer, doing a summer job just like I was. So we would literally hang out after work every single day, and just one thing led to another. It wasn’t like I was pursuing her or anything, it just happened naturally. So obviously that’s great for me because I didn’t have to make my moves. But when I had to make my moves, that’s when trouble happens.”

Recently, NextShark stopped by Brandon Wade’s office in Las Vegas, Nevada, for an interview where he revealed more details about his life, relationships and entrepreneurship.
The first thing I noticed when I walked in is that you don’t have your own office. You sit with your team in an open environment. Why is that?

“In the past, I never liked the corporate structure with lots of people with many levels and everyone is sort of defensive about what they own. At the end of the day, we are here as a team. We have a common goal. So let’s sort of row the boat together, so I want everyone to be able to approach me with their issues without worrying about whether the superior is going to have an issue with going over their heads. For that reason, I don’t even have cubicles here. If you see all our desks, there is no partition. I mean, it’s a little bit noisy at times, but it encourages a free exchange of information. I can see what anyone is doing at their desk at any given point in time, just like anybody can see mine. They can hear me say things, or we can shout in the room if we have to, so it’s the open environment that encourages teamwork and also communication.”

What inspired you to create

“After college, I was successful and making six figures but I was still awkward. So I would be at nightclubs and parties, standing and holding my beer bottle feeling out of place. It was many years later and I was still having a lot of difficulties dating. That’s when my mom’s advice really came back, and I said, well, it’s time to really take matters into my own hands., Yahoo Personals, those were not really working for me. I would create an account and get no response. I spent hours writing emails, no response. From there, I guess SeekingArrangement was born.”

Did you aspire to start a company before college?

“Yup! At MIT, my first goal was to become a millionaire by the time I turned 25. But it took much longer to achieve that. At MIT, I was participating in the 10K contest — now it’s called 100K — actually, it might be up to a 250K business plan competition. My team actually got the runner-up for that, but a lot of businesses launched that way, writing a business plan and participating in these business competitions. So I was no different; I was very entrepreneurial.

I wanted to start businesses and launched quite a few. One of the businesses I launched back in 1999 raised $10 million from VCs. Along with the dot-com bust, that business sort of was dissolved. Since then, I launched a few other things, both high tech businesses as well as low tech businesses, I was involved in a retail, I was in a tour company in San Francisco. Of course, I chanced at SeekingArrangement afterwards.”

Were other ventures successes or failures?

“The dot-com was a failure, but I returned half of the money back to the investors. Unlike most companies that continue to run until they are out of cash, the key point being is to look at opportunities, and if the market is no longer in the right spot, then you need to make a decision as to whether it’s best served that the investors get their money back or to continue until you run out of cash.

The rest has been a series of failures. I’ve failed many times, and I picked myself right back up and restarted again. Of course, then I chanced on SeekingArrangement, which is kind of interesting because that’s my sort of problem that I’m trying to solve. I have this fundamental belief that if you wanna start a business, try to solve your own problem, because that’s where you usually are most passionate about the issue, because it’s your problem and therefore has the most chance of success. You are solving the problem that you have, and therefore you’ll be its number one customer.”

Regardless of SeekingArrangement, would you say your mom’s initial advice was correct?

“I would say that’s the sort of traditional Asian parents’ thinking, right? They are very practical, and it’s always pragmatic. You are rich, you are gonna get girls! She’s telling my sister, ‘Study hard, because you need to find a good husband, and you are gonna find him at an Ivy league school.’ It’s pragmatic advice.

But in hindsight, there are many ways they accomplish the same goals. If you want to be more confident with women, then you could be out there practicing, getting the skills and becoming confident in the process. That took me a long time to learn. At the end of the day, it’s not necessarily about wealth, it’s about confidence. Wealth perhaps makes you more attractive and therefore gives you the opportunity to build up your confidence.”

Brandon’s Wife Tanya.
For a person that got his first kiss so organically, why would you create such a seemingly superficial site that’s so transactional?

“I would say organic is a great way to go, but organic does not happen all the time or very frequently. So it could happen, but it might happen to you only once or maybe three or four times in a lifetime. So why restrict yourself to the chance that it happens in such a seldom manner? Creating a website where you could go and just meet people literally tonight if I wanted to, I could meet somebody on I have dramatically improved my chances and increased the opportunity that’s available to me to find ‘the one.’ Not everyone is finding the one; some people are maybe looking for fun. Some people are maybe looking to fulfill themselves in the short term, but I think it’s a journey to find the one.”

Do you believe in true love?

“It’s kinda funny because I’ve been quoted as saying love doesn’t exist, and what I really meant is the infatuation type of love doesn’t really exist. I think we feel the chill down the spine and we get crazy about somebody we’ve just met, but given time, once you’ve known the person for a while, the magic is gonna disappear.

So the question is, can real, true love ultimately grow from that? That’s the true kind of love, understanding kind of love, the real selfless kind of love which would be absent of, say, jealousy, things that are most self-serving. So the answer is, yes, it does exist.

I’m married now, and I think me and my wife have a really good understanding of the fact that we care about each other in a selfless way, and we are also best friends. This is my third marriage, so I’ve failed many, many times, and that’s the point. There are a lot of people that think you meet someone and you get crazy about them and that’s true love, but that’s not always the case, because a relationship is a really tough journey.”

As a successful entrepreneur, do you ever fear attracting gold diggers?

“Of course it’s a thought to me! Perhaps that’s why I was so attracted to my wife when I met her, because she was very conscious of money and how she spends. So the concept of gold diggers, everyone wants a good life, all of us are looking to become independently wealthy and what not — that’s the American dream. So is it wrong to want things and to want luxury? The answer is no. So the question is, if somebody is only after you only because of the money, and they don’t care about you beyond that, then obviously you should be concerned about that, because the the last thing you want is to have somebody who loves you because of the money. But the question is, can that love really extend beyond the desire for a better lifestyle? The answer is yes.

A lot of sugar babies quit the website, and when we ask them why they quit, the answer surprisingly is that they found love not with the rich man, but the poor guy. So if they find love, all of the sudden materialistic stuff doesn’t really matter as much anymore. Of course, we also hear a lot of members find love on the website. Why? Because it’s a lot easier to find love when you are wealthy. You can wine and dine and have a wealthy and luxurious lifestyle, and it’s just so much more romantic than the poor lifestyle.

There are two ways to view it, and one way is, you are gonna use whatever you can to improve chances. So if it’s your amazing good looks, then so be it. If it’s your wealth and your wallet, then why not? If it’s your amazing ability to pick up, then use it.

But at the end of that day, whether the person is ultimately the one, you have to filter through all those checklists that you have. Does she care about me only for me, or is she willing to sacrifice the good life in case bad things happen? Will she still be with me in that case? That’s what you find out, the second point being that finance unfortunately is a very important component in any relationship. Fifty percent of all marriages fail because couples have financial issues; they disagree on how to manage their funds. The other one is spending too much, so being able to understand that upfront and communicate your financial expectations and making sure that gels well between two people is very important for any relationship.”

Brandon’s newly launched site for couples looking to explore polygamy.
As a man who’s been married three times already, do you feel you’ve finally mastered finding quality relationships?

“I don’t think I’ve mastered it, but I think I’m on the right path to achieving it by being very open with the person that I care about and want to be with for the rest of my life, meaning that problems might happen in the future, the monogamy might become very monotonous, and we may then sit down — and I know my wife will be very open to that, for me to sit down and really address the issue with her in a very honest manner. That might involve being monogamish or dating other people, that might involve a third or fourth person, it might involve other things, but I think it’s hard work. It requires two people to be really open-minded about how they are going to address their issues and understanding that they wanna continue this journey together.

I always go on these cruise boats and cruise ships, and I see couples married for 50 years. Obviously everyone in the audience is like, “aww” and “wow.” We are all so happy, and we applaud, but that’s not necessarily for everyone. Also, it’s not a necessarily easy thing to accomplish.”

What sort of challenges did you face building SeekingArrangement?

“I mean, we had issues. I’m not gonna kid. Vegas is a tough place to hire. Good people are not easy to find here. Obviously Zappos has perfected a formula for hiring good people, but even Tony [Hsieh] will tell you, slow to hire, quick to fire. We have experienced a lot of issues with HR in the past two years. Just growing pains.

I hired a guy who lied about his degree. He actually forged an MIT degree, so I thought for a long time he was an alumni, and obviously a search of the alumni database revealed his name wasn’t there. So I was like, ‘How come you are not in the database? I went to your house and saw your degree, looks just like mine. How come you are not in the database?’ He told me, ‘I’ve been in some secret military program through Lockheed Martin, and the government got me a degree that way.’ So I called the registrar’s office and found out that there is no such a program.

I’ve had two employees steal. The most recent employee was threatening us for some stuff. It’s just their issues, so we would try our best to make sure that the gatekeepers are more diligent in terms of interviewing people and making sure that we are hiring the best.

So now everyone has a background check and even more than that now. I’m actually requiring a credit check. If somebody has a really bad credit and is not organized in his personal life, the chances are you are hiring a desperate person who could become a disgruntled employee. Desperation might lead them to do what you don’t want them to do in the future.”

How have mobile sites like Tinder affected your business? What’s your plan to adapt as you go along?

“Tinder is kind of interesting because it’s sort of the rebirth of Hot or Not. I was at a dating conference earlier this year. Most of the dating site owners say that Tinder actually led to more people joining their dating sites and causing an increase in revenue, so I think Tinder is at a very high level raising the tide for everyone.

The other thing that I heard from obviously a lot of people is they are on Tinder, and they are looking for something. They find hookup situations, and they realize that they are not gonna find what they are looking for. So they then join all the niche sites to accomplish what they want. So Tinder actually has not caused our revenue to go down; it’s actually increased our revenue just like it has with all the other dating websites out there.”

In terms of entrepreneurship, what would you say was your biggest lesson you’ve learned so far? Did you have any mentors that helped you along the way?

“I’ve had mentors all along. When I was at General Electric, I had a few mentors there. Obviously when I was at MIT, I had a lot of mentors, especially with the entrepreneurship center. But nothing replaces going out there and failing. I would say the biggest mentor is all the failures I’ve had. Every time I fail, I learned the lesson that sticks, so I will not repeat the same mistake again. Somebody can tell you, ‘Do this,’ but you’re never gonna really take it to heart until you experience that failure yourself. So it’s kinda unfortunate, but failure is almost a necessity to success. So I would say to go out there and take the risk and don’t be afraid.

The other point I would say is that I have used many approaches to starting businesses in the past, obviously getting VC-funded, losing control of the company that way, using my credit cards, using my credit-taking loans and all the stuff. Obviously through those lessons, I’ve learned that it’s best to be a little bit more conservative. So with SeekingArrangement, at the very least I took a very conservative approach where I didn’t take loans, I didn’t use VCs, I was really able to bootstrap the whole effort.”

Speaking of money, you said you wanted to become a millionaire by 25. Were you driven by money? Or has that changed over the years?

“It has changed over the years. Obviously money was my mom’s practical approach, right? (laughs) Money is everything. So the monetary focus was the big one when I was younger. Now it’s different.

The point is, once you have a few million, does it really matter if you have even more? I mean, true, you might need a lot of money to buy a private jet, but do you really need a private jet? You don’t. So at some point, the quality of life becomes just as good no matter how much money you have. I think once you’ve reached that — I would say between $3-5 million level — you are probably just as comfortable as any other wealthy guy.

At this point, it is really about game, the excitement of being even more successful. As I tell my entire team, my goal now is to make all of you millionaires because that would cement for me that I can be even more successful than being just a one-trick pony, so to say.”

Are there any other exciting projects you are working on?

SeekingArrangement is going to take a huge step forward this year. Obviously we are going to launch a mobile app. That’s been a long time coming, and a lot of it is how we positioned our website in the past. In fact, a major TV network is about to launch a show about the website, or the lifestyle promoted by the website. It’s not so much sugar daddy dating anymore, but more about dating successful people. So there are ways in which we can position what the website is.

Beyond that, we are actually working on a new dating concept that is between a dating website and a matchmaker. As you know, if you go to a matchmaker, you would probably have to pay her $7,000 or $10,000 or $15,000, and she is gonna find you people that you can date. Whereas a dating website, you can pay $50 and you get sort of all-you-can-eat tons of emails. We are gonna be introducing something right in between. There is no such concept out there today. We are hoping to launch that out there by the summer.

Follow Brandon Wade on Twitter and check out his website.
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