…In physics, complex systems with many variables become chaotic the moment randomness is introduced. Humanity is a complex system of seven billion nodes, but each node is capable of learning. Despite the inherent chaos, if we all individually learn from each other, all seven billion nodes will eventually self-adjust into perfect flow. My idea to spread is for people to truly understand how their own minds work, as that directly dictates how you feel, think, and experience life…
We had the pleasure of talking with Brandon Wade and Dana Rosewall. They are the unlikely duo at the helm of Seeking.com, a dating empire that is currently in the middle of a massive identity shift. Wade, an MIT-educated engineer and former self-proclaimed cynic, founded the platform. Rosewall, a Gen-Z economics graduate with a mind for strategy, is his co-CEO. Their story is uniquely modern, not just because they run a massive tech company together, but because they actually met on the very platform they now control. It is a rare collision of business and romance, and they are using their own relationship as the blueprint for an ambitious corporate turnaround.
Their shared drive was planted long before they met, rooted in childhoods defined by strict expectations. Growing up in Singapore, Wade learned early that success was the only option. He recalls a childhood where poor grades led to harsh discipline. Looking back, he sees it as the foundational truth that dictated his life. Rosewall had a similar awakening as a young girl wandering a mall, pointing at things she wanted. Her mother told her plainly that she had better study hard if she wanted those things. That shared focus on education and ambition is the glue that holds their partnership together. They are able to run the business effectively, Rosewall notes, because they value the same things from a childhood perspective.
Wade’s early career was defined by an extreme, almost obsessive focus on climbing the corporate ladder. After finishing his MBA, he landed at General Electric, rubbing shoulders with corporate titans. He remembers a conversation with a top executive who bluntly told him that if he wanted to reach the absolute pinnacle of success, there was no such thing as work-life balance. That advice sent Wade on a relentless path. He launched multiple tech startups, failing and returning venture capital several times along the way. He admits today that those early ventures collapsed because he took shortcuts and made incorrect strategic decisions. But those failures paved the way for Seeking, a site born out of his own frustrations with romantic rejection. He vividly remembers being terrified to talk to women until his father gave him a piece of blunt advice. His dad told him, “If you walk up and make a fool of yourself, then you are a fool and you no longer have to worry about being one. Why don’t you just walk up to her?”
That willingness to face rejection is something Rosewall shares, living by the strict motto to never take no for an answer. She views a rejection merely as a sign that she is talking to the wrong person, a mindset that proved useful when launching their recent marketing initiatives. Instead of just targeting people ready for romance, she wanted to reach those who were jaded and fresh out of a relationship, an untapped market that required complex coordination of influencers and outreach. This sheer stubbornness serves her well as she navigates the reality of redefining a controversial brand. Seeking is currently undergoing a massive rebrand, shifting away from its chaotic past. Rosewall is clear-eyed about the challenge, admitting that the narrative of the past version of the site did get out of control. She anonymously sat in on user focus groups to hear the unvarnished truth about the platform. What she heard inspired her to look past the revenue and focus on how the product actually impacted human lives. To execute this pivot, they have had to shed a portion of their user base, alienating people who no longer fit the new vision. Wade acknowledges that it is painful to watch revenue fluctuate, but insists that the right customers will stay, and the wrong customers will leave.
The dynamic between the two leaders is a delicate balance of power and humility. Wade openly admits that years of success had surrounded him with people who only told him “yes,” allowing him to become self-centered. Rosewall, who originally planned to go to law school and loves a good debate, refused to play that game. When Wade was acting poorly, she told him upfront. Because he loved and respected her, he couldn’t just brush off the criticism. He had to sit with it. Rosewall firmly believes that keeping people around who just agree and never push back is a massive liability.
Today, they are trying to fix what they see as a broken dating landscape. They believe modern dating is crippled by a lack of honesty, caught between the exhausting endless swiping of Tinder and the overwhelming questionnaires of eHarmony. They want a platform where people can just state their true intentions without fear of judgment. Behind the scenes, the couple survives the intense pressure of running a global tech company through a rigid self-care routine. They use a Chinese oxygen chamber to recover from travel fatigue, take brutal cold plunges to snap out of workday stress, and completely shut off their phones every Saturday. It is a highly regimented life, but they believe it is necessary to achieve their ultimate goal. Wade views humanity as a complex system of seven billion nodes, and he believes that if they can fix the foundational piece of romantic love, society as a whole will begin to positively shift.
Brandon Wade and Dana Rosewall, it’s a delight to meet you both. Usually, we start by asking about an origin story, but I know we asked that a little bit in our first interview. I’ll ask it a little differently. Looking back to when you were young, was there a story from your childhood that you think planted a seed for the success you have now? We’ll start with Brandon, and then we’ll go to Dana. Was there a story that you think planted a seed?
Brandon: It was my mother. She was always doling out advice to me, telling me to study hard and things of that nature. When you’re young, you’re very rebellious. You don’t know why she is doing it; I only wanted to have fun. However, when you grow up, you realize much of what she told me became the foundational truth that I always fall back on, and that dictated how I conducted my life later on. Her advice was extremely valuable and made me who I am today.
You’re saying listening to your mother was what gave you…
Brandon: Absolutely. It’s funny because back in the old days, specifically in Singapore, you got spanked when you didn’t study or when you got bad grades. Today, you would call that abuse, but looking back, I’m truly grateful for those experiences.
Dana: For me, a moment when I knew I wanted to work my way up to CEO and become something bigger was when we were walking around the mall. I was quite young, and I kept telling my mom, “I want that, I want that.” She told me something similar to what Brandon’s mom told him: you had better study hard if you want those things. Ever since then, it has always been education first. I believe that is why our values are so similar and we get along so well. We can run the business effectively because we value the same things from a childhood perspective.
Each of you probably has many amazing stories from different parts of your career, and I’m sure this is hard to single out. Brandon, can you share one or two stories that stand out most in your mind from your career?
Brandon: There are quite a few. When I first finished my MBA, I was a management consultant, and after that, I joined General Electric. I was doing very well then, and Robert Nardelli was the CEO of GE Power Systems. He later left when he didn’t become the CEO of GE; he was one of the three finalists to take Jack Welch’s position and ended up at Home Depot. I recall him telling me that if you want to be like Jack Welch, there is no such thing as a work-life balance. He said it is either one or the other. That put me in a specific mindset to be extremely focused on my career early on. Later in life, I came to the realization that once you achieve success, you need to have balance; otherwise, you will burn out. However, my experience at GE set me on a specific path. Focus and attention are absolutely required if you are aiming for success and career advancement. Once you get there, you need to slow down and work on other aspects to make life a little more well-rounded.
What do you say, Dana? Is there a story that stands out from your career?
Dana: I came into this position from an economic researcher role, which was a lot of fun. I worked with professors and wrote reports for the Economic Forum. One of the moments that really stands out in my career as a CEO is that one of the first things I did was ask for a focus group because I wanted to hear directly from our users. It was very surreal because I wasn’t visibly on the call. They couldn’t see my face, which was important because they might have warped their answers if they knew the CEO was present. Sitting anonymously in the back of these focus groups was incredibly interesting. It set my mind up for success from the customer’s perspective because I was able to hear what paying customers thought and how the product changed their lives. Those stories stuck with me and inspired me to run the business with a holistic view, rather than just prioritizing revenue. Revenue is still important, but it was amazing to hear our customers talk about how the product changed their lives. It motivated me to work harder for the people whose lives we are changing.
That is a great story. There’s a saying that ‘no’ is not rejection but redirection. Do you have a story where you received a ‘no’ to an opportunity, but it led to an unexpected blessing or success?
Dana: The motto I live by is to never take ‘no’ for an answer. It has worked out very well for me. Recently, I reached out to an influencer I wanted as a spokesperson for a campaign, and their agent said no. I thought to myself that I really wanted to work with them and I would figure it out; I was simply speaking to the wrong person. I utilized my entire network and found a way to collaborate with that person. It caused us to redevelop the scope of what we wanted them to do, and it actually became even more successful than our original plan. That is a recent example, but I absolutely live by that motto.
Brandon: It is similar for me. A ‘no’ tells me that we should look for a different way.
Dana: Exactly. You are just not asking the right person.
Brandon: We have always faced rejections all the time. Specifically in dating, you have to learn to be okay with hearing ‘no’. During my childhood, I was very afraid of getting rejected. I preferred not to put myself in a situation where I could be rejected. By doing so, you end up closing a lot of doors and opportunities. My dad gave me great advice once when I told him I was too afraid to walk up and say hi to a girl. He asked me why I was afraid, and I told him I was afraid of being rejected and looking like a fool. He said, “Well, if you walk up and make a fool of yourself, then you are a fool and you no longer have to worry about being one. Why don’t you just walk up to her?” I did exactly that, and I did make a fool out of myself.
Dana: Honestly, the rejection redirected you. That is what built Seeking in a sense, right? Getting those rejections and building a site that worked for you.
Brandon: Yes. It would be a problem if you kept hearing ‘yes’. Being surrounded by ‘yes’ people is problematic.
There’s a related idea that sometimes our mistakes can be our greatest teachers. Do you have a story about a mistake you made when you were first starting and the lesson you took away from it?
Brandon: I’ve made a lot of mistakes in my life. Over time, as you gain more experience and success, you can become a bit self-centered. Meeting Dana and having her tell me upfront when I was acting poorly forced me to self-reflect and realize my mistakes. The ability to have someone you can listen to, take input from, and use to recognize those mistakes is key.
Dana: A mistake I’ve learned from is keeping people around — whether in your personal life or on your team — who are not there for the long term. Keeping people around you who aren’t aligned with you, even if it feels like they provide a specific benefit or you cannot get rid of them, is actually more harmful than helpful.
That is great advice. Brandon, were you saying that Dana’s feedback actually changed you? That it polished you?
Brandon: Yes, because in the past when people would criticize me, I would naturally defend myself and move on. With Dana, I cannot do that. I love and respect her, and her feelings matter to me. If she thinks I am in the wrong, I want to know why.
Dana: I was actually planning to go to law school when I met Brandon, so I wanted to fight for a living and I am very good at debating. Having ‘yes’ people around you all the time, which was his situation, is an issue. Having someone step in and ask, “But what if you thought about it this way?” is incredibly beneficial from both a personal and professional perspective. It is a problem when everyone around you just agrees and never pushes back.
Brandon: Mistakes are great because they give you an opportunity to improve. I failed in numerous businesses and startups before I successfully launched Seeking. I can name at least two or three dot-com failures where I raised venture funds and had to return the money because the businesses did not work out. They failed because we took shortcuts and made incorrect strategic decisions. I made a lot of mistakes along the way.
It is amazing that you have the humility to admit that and be so self-aware.
Brandon: We will continue to make mistakes moving forward, but we always want to learn from them.
Dana: If there is one thing people should know about Brandon, it is that he has a tremendous amount of humility. He is able to step back, re-evaluate a situation, and overlook his initial beliefs. That is a very important personal habit.
What has been the most challenging project or role you have taken on so far, and why?
Dana: Coming into the CEO position from my last role was challenging; on paper, I was not supposed to be here. However, I have learned that if you put yourself in a situation and do the best you can, it yields good results. A recent project that was very challenging was a massive, holistic marketing campaign called the Breakup Campaign. Most dating sites target people who are ready for a relationship. I wanted to target people who just got out of a relationship and were feeling jaded. That is a market that hasn’t really been tapped. Putting together an entire campaign with PR boxes, influencers, surveys, and landing pages was extremely challenging, particularly getting the team to communicate effectively and execute the campaign on time.
Brandon: Coming back from retirement and traveling the world to now being responsible for this rebrand with Dana has been quite challenging. It is almost a 180-degree turn. Convincing people that this change is real is difficult. As my dad used to say, actions speak louder than words. When I told him I was coming back to change the business, he reminded me of that. I realized I have to convince everyone over time through our actions; I cannot convince people simply with a phone call.
That is what struck me the most. I have never seen a company try to do a 180-degree switch so authentically and sincerely. To me, it is an amazing redemption story. I would love to hear the thought process behind that and how it is going. What has the response been so far?
Dana: The response has honestly been excellent. You hit on the main point: you have to be sincere. You have to be honest, address what you did in the past, explain how the narrative got out of control, and show how you are trying to take it back. The narrative of the past version of the site did get out of control, and we wanted to reel it back in because it no longer aligned with Brandon’s original intentions, nor did it align with why I originally joined the site. Being authentic about our goals and slowly making product and messaging changes helps people adapt without shocking them.
Brandon: The right customers will stay, and the wrong customers will leave. That is just the nature of a rebrand. Part of the challenge has been watching our revenue fluctuate and not panicking, but we have to stick to our vision because we are building something with a strong foundation. It is going to be painful at times.
Dana: The truth is, during a rebrand, you have to shed some users who no longer align with your vision. That is okay. We still have a core group of people on our site who believe in it and have found success. That is what keeps us running. The adoption rate for the new direction has been incredibly high, and our revenue has made a complete rebound, which is fantastic news for any business owner. Knowing you are building a strong foundation makes the experience better for you, your employees, and your customers.
As you know, people are becoming jaded about dating. What do you think people really need, and how can you address that? People desperately want to connect with others, but they are having a hard time using technology to do so. What do you think people need to help them make that connection?
Dana: I think they need honesty. People often join dating sites and misrepresent their intentions. If you honestly stated, “I am looking for a relationship but I am about to move,” that clarity would help people align much better. Right now, people are too general with their profiles, making it difficult to gauge their true intentions. Clear communication brings authenticity back into the process. The industry has become highly gamified with endless swiping and virtual roses. We avoid all of that because we want our platform to be effective. We don’t want to play games; we simply want people to state what they want and find someone who matches that.
Brandon: The eHarmony approach, where users are asked hundreds of questions, doesn’t work very well. Conversely, the Tinder approach, where you can sign up in five minutes and start swiping immediately, is also flawed. The right approach is to start with honesty and vulnerability if you are truly looking for a connection. Many people avoid this because they fear rejection or presenting themselves in a way others might dislike. However, honesty is the crucial first step to finding someone who will like you for who you truly are.
Can you share a story about customers whose lives were changed by your platform? I know people love hearing success stories, and I am sure you have thousands, maybe millions of them.
Dana: I am actually one of them! My entire life changed the day I met Brandon. Outside of my own experience, we have many stories. Brandon’s best friend is a great example.
Brandon: Yes, my best friend Mark used the site and found his wife. We have many people in our circle who have found love this way. I have a female best friend who used the site and is now married to a man she met on Seeking as well. Even within our inner circle, quite a few friends have used the site successfully.
Dana: We had one particularly memorable story involving our CTO down in Miami. He saw a huge parade of yachts with people celebrating with champagne. When he asked what was going on, he learned it was a couple getting married. They had met on Seeking, and the bride went to Columbia University. Seeing their love celebrated in such a massive gathering made our CTO feel incredibly proud to work for a site that facilitates those types of connections.
Brandon: The best success stories are when you see people completely in love, their lives forever changed for the better. It truly fills your soul.
Dana: We like to say the ultimate success story is that Brandon is the only founder of a dating site who has ever used his own platform to successfully find love.
Brandon: I would say that is true. No other dating site founder has used their own product to find love, which almost makes you question their business models.
Do you have any exciting new initiatives? You mentioned the breakup initiative, is there anything else you are working on?
Dana: We have a ton of initiatives. We are currently doing Q2 planning, which includes many marketing campaigns focused on changing our messaging. We are shifting toward in-real-life marketing. For instance, we will be at the Revolve Festival, an exclusive influencer event tied to Coachella, doing a live activation. We will focus heavily on real-world events and influencer partnerships this year, with several fun campaigns launching in the next two quarters.
Brandon: Dana’s goal is to take our brand voice and project it outward. She wants people to not just see it, but hear, experience, and feel the possibilities of what can happen when two great people fall in love and prioritize each other.
Dana: We are also working on a rendering of an AI feature designed to make dating more effective. We are still in the testing stage. Every dating site is rushing to implement AI, but I believe our approach is very strong. I reviewed a model of it recently and was very impressed. I am hopeful that this will provide people with a much more efficient dating experience in the future.
Brandon: A project I would love to launch down the road involves helping more people achieve success in their careers. I firmly believe a “career first, love second” approach is the right path. It provides a strong foundation for solving problems, facing difficulties, and creating an abundance to share with a partner. I hope to help people figure out how to find their passion and succeed professionally.
Are you saying that Seeking might add a section for mentors or business networking, or do you mean something else?
Brandon: Perhaps that. Or perhaps creating more self-help content focused on career development and providing resources to help users succeed.
Dana: It really breaks down into two paths. First, for people who haven’t reached financial success yet, we want to create educational content explaining how successful users built their careers. Second, regarding networking, we have definitely considered it because our database is highly unique, featuring many affluent, high-net-worth individuals. Linking them up for business networking, not just romantic relationships, has been discussed. It would require a major product update, but we are actively talking to our customers to gauge their interest.
Brandon: I know Bumble attempted something similar with Bumble Bizz.
Dana: The issue there is that their database differs greatly from ours. We have a very specific concentration of highly successful people. Most men on our site are entrepreneurs, CEOs, and founders, so a networking feature inherently makes sense for our platform.
Brandon: It will likely focus on showcasing successful members and having them provide valuable career advice to help spread success within our community.
You touched on this earlier, but it would be incredible to see a gathering of people who found love, got married, or achieved financial freedom because of the app. Imagine a convention of a thousand couples who met on the site.
Dana: We actually have an upcoming ad campaign closely aligned with that concept. Because most people find us through word of mouth, we designed a campaign highlighting successful couples. We have also discussed hosting a large event to bring all these couples together. Sending them to a hotel and planning group activities is a wonderful community-building exercise and a full-circle moment for the brand.
This is our signature question. Brandon and Dana, looking back to when you first started your careers, can you share five things you learned over the years that would have been nice to know when you first started?
Dana: First, never take ‘no’ for an answer. I apply that approach to almost everything in my life. Second, you learn faster by putting yourself in uncomfortable situations. Stepping into a CEO role or running a complex campaign forces you to learn quickly on the job — skills you cannot necessarily learn in school. I wish I had known that so I could have trusted myself more. Third, your team is your lifeline; having an aligned team is an extension of yourself. Fourth, the smartest people simplify things rather than complicating them. In meetings, people who use complex jargon might seem smart, but true intelligence is taking a complex situation and explaining the solution in a single, clear sentence. Finally, running a business should prioritize the customer over revenue. Ask what you can do for your customers, and you will build a business that genuinely adds value to society.
Brandon: First, I wish I had known how important it is to figure out your true passion. When I was younger, I focused solely on monetary success, which is a trap that pulls you away from what brings you meaning and happiness. Second, you must identify your talents. I advise younger people to try everything — use the internet and YouTube to explore — because you won’t discover your talents until you put them into practice. Third, failure is a precondition to success. If I had understood that earlier, I would have been more prepared for setbacks. Fourth, human relationships are crucial. I was a nerd who focused strictly on studying, but mastering the science of relationships provides an exponential lift to your success by allowing you to build strong teams. Fifth, actions speak louder than words. You are playing the long game, and if you stick to your plan with the right mindset, it will ultimately work out.
Dana: I love the point about failing. I wish someone had taught me to view failure simply as a learning opportunity. I would add that as my sixth point.
If you succeed in the way you hope and envision with this new direction for Seeking, how do you believe the dating landscape will look different in ten years?
Brandon: My vision is that people will celebrate their anniversaries bigger every single year. Instead of thinking the grass is greener on the other side, I want partners to say, “I am so happy here, I could not possibly imagine choosing anything else.” The more people find that level of relationship, the stronger our communities will become. Dana and I are successful today largely because our parents taught us well and set us on the right path. Just as AI learns from its training data, human intelligence is shaped by what we observe. If we can fix the foundational piece of romantic love, society as a whole will begin to positively shift.
Dana: For me, industry success looks like the ability to pair people accurately and efficiently. Using technology to quickly capture true intentions will eliminate dating fatigue, leaving people energized and excited to use dating platforms. Choosing a life partner is one of the most important decisions you will ever make. The ultimate indicator of success for the dating industry is an increase in successful marriages and happy relationships. If we can help people effectively find what they are looking for, we avoid mismatches and create the beautiful anniversaries Brandon mentioned.
Fascinating point. Are you in touch with the heads of Bumble, Tinder, and Hinge? Do you work together?
Dana: We do not currently work with them, but we would not be opposed to it. Much of the industry falls under the Match Group umbrella. I have discussed with Brandon how we, as an entire industry, can create a broader movement rather than just individual marketing pushes. I believe that will eventually require us to collaborate with Match Group. We actually have a few former Match Group employees working with us now, which is a step in the right direction.
We are almost done. On a personal level, can you share some self-care routines you practice to help your body, mind, and heart thrive?
Dana: We utilize an oxygen chamber that we bought from China. Whenever we are tired from traveling or lack of sleep, working inside the chamber helps repair muscles and energy faster. I highly recommend it for busy people who cannot exercise every day. We also love cold plunges; the 30-degree water instantly snaps you out of a stressful workday. Mentally, Brandon and I prioritize decompressing together every night. Running a company together makes separating work from personal life difficult, but we dedicate 15 to 20 minutes each evening just to check in on how the other is feeling. Finally, I am a huge proponent of therapy. As a CEO with a high-stress job, having a professional to talk to is excellent self-care.
Brandon: This ties back to work-life balance. I do not believe in using balance as an excuse to solely focus on work or family. We have to unplug, or stress will build and stifle our creativity. As Dana mentioned, we talk every evening to decompress, and we make sure the weekends are a true break from work.
Dana: Yes. We reserve one day every weekend, usually Saturday, where we shut our phones off and completely decompress. Saturday is for play, and Sunday is for self-reflection and reading scripture.
This is our final aspirational question. Dana and Brandon, because of your great work and the platform you have built, you are both people of enormous influence. If you could spread an idea or inspire a movement that would bring the most amount of good to the most amount of people, what would that be?
Brandon: In physics, complex systems with many variables become chaotic the moment randomness is introduced. Humanity is a complex system of seven billion nodes, but each node is capable of learning. Despite the inherent chaos, if we all individually learn from each other, all seven billion nodes will eventually self-adjust into perfect flow. My idea to spread is for people to truly understand how their own minds work, as that directly dictates how you feel, think, and experience life.
Dana: I would push the narrative to always help others, regardless of whether they are in desperate need. Helping others forces you to put yourself in their shoes and fosters a kinder, more giving society. Brandon and I plan to create various charities because we have the resources to do so. Centering our lives around helping family, friends, and communities in need is our ultimate goal.
It has truly been a delight to meet you both. How can our readers continue to follow your work? How can they get involved with Seeking, and how can they support your efforts?
Dana: They can follow Seeking on social media, where I share a lot of creative content on how to communicate and express love. If anyone is looking for love, or just looking to meet cool people and have fun, they should check out the site.
Brandon: Life is meant to be experienced. People should get out there and experience it. That is the motto.
Amazing. Well, Dana and Brandon, it was delightful meeting you. I wish you continued success, good health, and blessings, and I hope we can do this again next year.
Dana: Absolutely, thank you so much.
Brandon: Likewise. I wish you health and success.
Dana: Have a good day.
