The New CEO Playbook: Brandon Wade and Dana Rosewall of Seeking.com On Balancing Purpose, Profit, and Personal Brand
The leaders who build movements don’t sound perfect when they talk about their path. They’re comfortable acknowledging the parts both did and didn’t work. They can say, “I messed this up,” or admit they weren’t sure what the right call was at the time. What matters most is being willing to learn from it and do better next time.
The most successful modern CEOs are rewriting the rules of leadership. They’re not only building profitable companies but building purposeful brands with personal voices behind them. These leaders understand that in today’s world, people invest in people. Their stories, values, and visibility fuel loyalty, attract opportunities, and drive business growth far beyond traditional metrics. In this interview series, we’re sitting down with leaders who’ve learned to balance purpose, profit, and personal brand — and who are using their influence to shape the future of business leadership.
As a part of this series, we had the pleasure to interview Brandon Wade and Dana Rosewall.
Brandon Wade is the founder and co-CEO of Seeking.com, the world’s largest dating community for successful and ambitious singles. He holds a BS in Electrical Engineering from MIT and an MBA from MIT Sloan School of Management. After meeting his wife and co-CEO Dana on Seeking.com in 2020, Brandon transformed from a self-proclaimed cynic about love into an advocate for helping others find relationships worth choosing over everything else. Dana Rosewall is the co-CEO of Seeking.com, which she leads alongside her husband Brandon with a shared mission to transform the dating industry. She holds a BSBA in Economics with a minor in FinTech from UCF. As a Gen-Z leader responsible for Seeking’s marketing strategy, Dana brings a fresh generational perspective to the platform, combining her determination and strategic mindset with an innate understanding of how Gen-Z daters think and connect.
Thank you so much for joining us! Can you share your backstory and what led you to become the leader you are today?
Brandon: I was born and grew up in Singapore. I was raised by a Tiger mom who instilled an education-first philosophy. As a result of her influence, I excelled at school. I placed third in the Singapore Mathematics Olympiad and first in the Singapore Physics Olympiad for my year. My parents taught me to have clear goals and to work hard to achieve them. That drive eventually took me to MIT, where I studied Electrical Engineering and later earned an MBA. Engineering trained me to break problems down and think systematically, while business taught me how to build organizations that can actually solve them. But it was my father who had the greatest impact on my leadership style. He always told me: “Action speaks louder than words.” That phrase shaped how I lead today.
Dana: I always knew I wanted to be a CEO from a young age. My parents instilled in me the importance of putting education first, above all else, much like Brandon’s upbringing. I was driven and focused from an early age. I fast-tracked my education by completing my AA degree before finishing high school, and went on to earn a BSBA in Economics from UCF. That ambition stayed with me. I’ve always been goal-driven and persistent. I never thought meeting Brandon on Seeking.com would be part of my professional story, let alone lead me to the C-suite and a partnership in life and business.
Our parents valued similar things: education, clear goals, and hard work. Those shared values are part of what makes our partnership work so well, both as a married couple and as co-CEOs.
What’s the “why” that drives your work? How has your personal sense of purpose evolved as your business has grown?
Brandon: When I first launched Seeking.com, my “why” was deeply personal. I have had horrible experiences on mainstream dating apps where I would write hundreds of messages and get less than 1% response rates. My accomplishments, ambition, and potential as a partner were unable to help me stand out on platforms designed around photos and generic profiles. That frustration drove me to launch Seeking.com in 2006, a dating platform where successful men can meet the most ambitious women. It was based on my mother’s advice and her observation that rational women naturally prefer a partner who can make their life better. I wanted to build a place where that honesty was not only accepted but encouraged. Initially, my purpose was also to achieve success. But once I achieved that, I lost my “why.” More money does not make you happier. Then Seeking.com actually helped me find the relationship I was looking for when I met Dana. I was so blown away by what I found that my purpose transformed completely. Today, I want to help other people find what I found. Helping others find meaningful relationships is what drives my fulfillment now.
Dana: My “why” is simple: to help people find lasting relationships. Seeking.com fundamentally changed my life for the better, bringing me Brandon and a partnership that fulfills me personally and professionally. Now I want to help others experience the same.
My personal sense of purpose has evolved into a shared one as the business and our team have grown. It is no longer just about what I want to achieve individually, but what we can build together and how many lives we can impact.
We both found each other on the platform we now lead. For this reason, our “why” is unified in a way that few co-CEO partnerships can claim. We want to create more love in the world because we have experienced what that love can do. The dating industry is optimized to match people based on interests and attraction, which leads to relationships that are “good enough” or “good enough for now.” Such relationships have a finite lifespan. We want to help people find relationships they are willing to choose over everything else.
Let’s now move to the core of our discussion. This series is about balancing purpose, profit, and personal branding. Can you help explain why each of those three matters, and why they can sometimes pull against each other? If possible, share a real example from your experience.
Brandon: Each of these three elements serves a distinct function. Purpose gives you meaning and direction. It answers the question of why you’re building what you’re building. Without purpose, you’re just chasing metrics that don’t ultimately satisfy. Profit gives you sustainability. If you do something that does not generate profit, you won’t be able to pay your employees, and the engine won’t sustain. Purpose without profit means your idea isn’t feasible. You can have the most noble mission in the world, but if you can’t fund it, it dies. Personal branding is the amplification of the other two. It builds trust and credibility. With that trust, your message and the ideas you are marketing become magnified exponentially. People don’t just buy products. They buy into people. A strong personal brand makes everything else more powerful.
Dana: The tension between these three is real, and most companies struggle with it. This is especially true for public companies, which serve two masters: their shareholders and their customers. While their stated purpose may be to serve their customers, many company leaders find themselves choosing shareholders and profitability over the people they’re supposed to serve. We learned this lesson firsthand. After we got married, we retired to travel the world and explore life together. During those two years away, many decisions were made without our oversight. They were decisions that brought in more profit at the expense of our customers’ experience. The leaders running the business lowered the friction and requirements to join our platform. On paper, this looked like growth. In reality, more fraudulent and low effort users made it into our community and safety declined. The people we were supposed to serve had a worse experience. This is the reason we decided to come back to run the business, so we can navigate its transformation back to the right purpose and better serve our customers.
Many CEOs focus heavily on strategy and profitability but hesitate to invest in their personal brand. What do you think about that? What have you seen work best?
Brandon: Focusing on strategy and profitability instead of investing in personal brands is the wiser path for most CEOs. Focusing on one’s personal brand can lead to distractions, especially when the concern for personal brand outweighs the more important priority of serving purpose and generating sustainable profit. Consider Jack Welch, who was CEO of GE. In the 1990s, he turned GE into the most valuable company in the world. He wrote numerous books and became known as the world’s best manager. He left at the absolute peak, before the cracks in his strategy became visible. Looking back 20 to 30 years later, it became clear his approach was destructive to the company he ran by trading long-term engineering excellence for short-term financial engineering. The culture of fear he cultivated and the reliance on banking profits left GE unable to adapt to the 21st century. In the short run, it seemed like he was winning. But in the long run, it became clear his personal brand was his priority. Profit supported and fueled his personal brand, not the other way around.
Dana: In our opinion, one should focus on strategy and profitability first. What is most important is the creation of a business that is actually profitable because it is adding real value to its customers. Once that is accomplished, then putting focus on personal brand makes sense. At that point, your personal brand can act as a multiplier to your business because at the end of the day, people trust people more than they do companies. But that trust has to be built on something real. If you build a personal brand on top of a hollow business, or worse, at the expense of your business, you’re building on sand. Get the fundamentals right first. Create genuine value, then let your personal brand amplify what you’ve already built.
What are some misconceptions you’ve encountered about personal branding in the C-suite, and how do you challenge those narratives?
Brandon: The biggest misconception is that personal branding is vanity. In reality, it’s the opposite. In a world of infinite choices, people need shortcuts to decide who to trust. A CEO’s personal brand is a signal. It tells customers, employees, investors, and partners what this company is really about. Do not think of it as self-promotion, but as communication.
Dana: Another misconception is that personal branding means being on social media constantly or chasing viral moments. While it may be a part of personal branding, it is not all of it.
Personal branding as a whole is about having a point of view and standing behind it over time. Sometimes that shows up publicly, like in a podcast, interview, or social media post. Other times, it’s much quieter. It’s how you handle a difficult conversation with an employee or the call you make when no one else is in the room. Those types of moments add up. That’s where a brand is actually formed, not just in the public-facing ones.
We’ve challenged a lot of these assumptions simply through results. Seeking.com has grown significantly in annual revenue with very little traditional advertising. Our growth comes from word of mouth, from press coverage, and from people sharing stories about finding meaningful relationships on our platform. Much of that traces back to the visibility and accessibility Brandon has maintained as a founder over the years. And it will continue as we lead together as co-CEOs. Our personal story, how we met on Seeking.com and built a life and business together, is now inseparable from the company’s brand.
What’s one specific way your visibility as a leader, through interviews, speaking, or social media, has directly impacted your organization’s success? Walk us through what happened. How did you know it worked, what changed in measurable terms?
Brandon: One example is that we created a media moment by going public with our story, which shifted the conversation from scandal to transformation. For years, and even after a full rebrand, coverage of Seeking.com was almost uniformly negative: “Sugar daddy site.” Transactional. Exploitative. When we began being more open about our relationship, things changed. We shared our wedding. We talked publicly about choosing not to have a prenup. Slowly, the questions from journalists shifted too. The questions went from, “Isn’t this just prostitution?” to “How did your views on love change?” and “What made you fall in love with each other?
Dana: In measurable terms, our positive media mentions increased dramatically. Inbound partnership requests from mainstream brands started coming in. Employee recruitment became easier because people saw a company in transformation. The most important metric, though, is harder to quantify: credibility. Credibility can only be acquired through the achievement of real results. As our credibility builds, people will listen differently because they will know we are not just selling something but are living proof of what we’re talking about.
Balancing profit and purpose is easier said than done. What practices or principles guide your decision-making when those two goals seem to conflict?
Brandon: The most important principle is this: purpose must never be profit. Profit must always follow purpose. And for a business, purpose has to be adding real value to its customers. When we have to make a decision, we always ask ourselves one question: which decision would we be proud of 10 years from now? Short-term profit is seductive. There have been many opportunities to monetize Seeking in ways that would have been lucrative but would have taken us further from the kind of platform we want to build. Features that would have encouraged more transactional behavior. Partnerships with brands that didn’t align with our values.
Dana: The principle we follow is that purpose is the long game and profit is the scorecard. If you’re genuinely creating value for people, profit follows. It might take longer than you want, and there may be quarters when you leave money on the table. But sustainable businesses are built on genuine value creation, not extraction.
We share the same perspective on this, which is essential for our partnership. We serve as a check and balance for each other. When we’re making big decisions, we always have a partner who will challenge the other if we find ourselves optimizing for the wrong things. That accountability keeps us honest. It’s easy to rationalize short-term decisions when you’re making them alone. It’s much harder when someone you love and respect is asking you to defend that choice against your values.
Can you share a story about how aligning your personal values with your company’s mission created a breakthrough in performance or growth?
Brandon: After Dana and I got married, we stepped away for a while. Dana finished school, and I retired. We took an extended honeymoon and gave ourselves the space to live a little. We traveled, explored, and focused on each other. It was drifting away from its original purpose, and too many decisions were being driven by short-term profit at the expense of the customer experience. At some point, it became clear to us that if the company was going to change course, it would have to be us who made that change.
We agreed that we would only come back to run the business if we could do it together, and that the business would always be secondary to our relationship. That was non-negotiable.
Dana: We also had to align on our values before we returned. We decided we would only run this business if we could do the right thing. And for us, the right thing is adding real value to our customers, helping them find the kind of relationship that Brandon and I have found on Seeking.com. We came back with that mission and immediately took action. We implemented required selfie liveness verification for all users, significantly eliminating fraudulent profiles. We invested in AI technology to enforce our community guidelines and rapidly eliminate “low effort” and “transactional” behavior from our platform. We made it harder to join and harder to behave badly once you were in.
The short-term result was an expected contraction in revenue. When you raise the bar, you lose some of the people who couldn’t clear it. We accepted that tradeoff because it aligned with our values and those efforts are finally paying off. In the past two quarters, our revenue has recovered and is on the upswing. More importantly, the quality of our community has significantly improved. We’re building the platform we actually want to lead, one that reflects who we are and what we believe relationships should be.
In your view, what separates a leader who simply “runs a company” from one who builds a movement around their message?
Dana: We believe it comes down to one word: vulnerability.
Running a company requires competence, but building a movement requires connection. Connection requires letting people see who you really are. Not the curated or press-release version, but the complicated, evolving, sometimes contradictory human being. The leaders who build movements don’t sound perfect when they talk about their path. They’re comfortable acknowledging the parts both did and didn’t work. They can say, “I messed this up,” or admit they weren’t sure what the right call was at the time. What matters most is being willing to learn from it and do better next time.
Most executives are trained to always sound certain, have answers ready, and never show uncertainty. That kind of confidence might impress people, but it also creates distance. Competence earns respect. Humanity is what actually creates connection.
Brandon: When I think about my own journey, this is exactly what created resonance. I publicly reversed my position on love. I admitted my cynicism was a defense mechanism. I share openly how Dana transformed me. People who are skeptical about love see themselves in my past self. The guy who wrote “love is a concept invented by poor people” in 2014. The guy who had three failed marriages and built walls around his heart. When they see that person found genuine love and completely changed his worldview, it gives them permission to believe change is possible for them too.
How do you integrate storytelling into your leadership, both internally with your team and externally with your audience or clients?
Dana: We try to always make our “why” concrete and personal, both inside the company and outside of it. Internally, when we’re making product decisions, we often share stories from our users. They’re people whose lives changed because of what we built. We also share our own story frequently. New employees hear about our journey, how meeting each other on Seeking.com changed us, and why we believe so deeply in what we’re building.
When people understand the story behind the strategy, they make better decisions. They can extrapolate and handle ambiguity. They know what we’re actually trying to build, so they don’t need to be told what to do in every situation. The story becomes a guiding compass.
Brandon: On the outside, we’re very intentional about where and how we show up. Every article, interview, speaking engagement, and piece of content we put out is an opportunity to move the narrative. If a story does not advance us, we turn it down. The old story about Seeking was written by critics. The new story, about transformation, about how Seeking.com is evolving to help people find fulfilling relationships, is the one we are actively authoring.
Can you share a time when taking a public stand or sharing your story authentically strengthened your credibility or influence?
Brandon: A time when our credibility clearly strengthened came when we chose to be very public about our relationship and the values behind it. We married without a prenup, and we waived our right to divorce, which caught many people off guard.
To give some context, I’m the founder of a dating platform and have been married three times before. I once wrote publicly that “love is a concept invented by poor people”. Having said that, I was the last person anyone expected to make such a declaration. When we shared this decision publicly, it was a risk. Some people thought it was reckless, while others thought it was a publicity stunt. But for us, it was simply the truth of how we feel about each other and our relationship.
Dana: We found that this authenticity strengthened our credibility in ways no marketing campaign ever could. When we speak about commitment, about finding transformational love, people know we mean it. We’re sharing what we’ve staked our lives on.
What are your “Top 5 principles for balancing purpose, profit, and personal visibility?” (Please include a short example for each, plus one action a reader could try this week.)
The secret to balancing purpose, profile and personal visibility is alignment. The top 5 principles in achieving balance are:
1. Lead with Purpose.
2. Follow with Profit.
3. Serve with Personal Visibility.
4. Find One Person Who Will Hold You Accountable.
5. Do Your Best and Trust Your Approach.
Finally, if you could summarize your leadership philosophy in one sentence, what would it be — and why?
Brandon: Lead by example, because belief is contagious when it’s real. I don’t ask anyone to do something I wouldn’t do myself, and I have to believe in what I do. If I don’t believe in it myself, I won’t be able to convince anyone else. This is why our personal story matters so much to how we lead Seeking.com.
Dana: Never accept “no” as the final answer. I am a very determined person who does not give up. When someone says no, I’ve learned it means I’m asking the wrong person. So I proceed to ask someone else, and someone else, until I find the right person who can say yes. This philosophy has shaped how I approach every obstacle. In business, “no” reflects someone’s limitations, not the actual boundary of what’s possible. The right opportunity, partnership, or solution is out there; my job as a leader is to be persistent enough to find it.
Brandon and I complement each other in this way. He leads through authentic example, while I lead through determination. This creates a great leadership dynamic.
How can our readers continue to follow you or your company online?
You can find us at Seeking.com, where we’re building the future of intentional dating, and on helping people find relationships that are worth choosing over everything else for. We are both active on LinkedIn, as Brandon Wade and Dana Rosewall, where we share our thoughts on relationships, entrepreneurship, and the intersection of the two. We can also be found on Instagram as @askbrandonwade and @seekingofficial, and on TikTok as @officialseeking.
Thank you so much for sharing all of these insights. We wish you continued success and good health!
The New CEO Playbook: Brandon Wade and Dana Rosewall of Seeking.com was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.