David Metz is the Founder and CEO of Prizeout, an adtech company that partners with various industries to optimize money flow and put money back into consumers’ pockets. A career entrepreneur, David started his first company, Flugpo, in 2006 after a 10-year stint in financial services and equity trading. Prior to Prizeout, he was the CEO and co-founder of a mobile trivia app called FleetWit where users could take bets on their trivia skills. His broad leadership experience in finance, marketing, and tech across both large firms and startups put him at the ideal intersection to lead an industry disruptor like Prizeout. David attended Drexel University and lives in New York City with his wife and two kids.

What does “entrepreneurship” mean to you?
David Metz: Entrepreneurship is a deeply philosophical mindset and lifestyle that empowers us to shape the world around us. It isn’t just about starting businesses; it’s about seizing opportunities, solving problems, and making ideas happen. Entrepreneurship is a lifestyle – one that doesn’t just impact me, but also those closest to me – family, friends—hopefully inspiring and influencing them along the way.

Tell us about your first experience with entrepreneurship.
DM: I’ve always had an entrepreneurial spirit and a curious mind. Growing up, I absorbed invaluable lessons around the dinner table from my parents, who ran their own irrigation company and later ventured into commercial real estate. Our family conversations always revolved around business—what was working, what wasn’t, the highs, and the lows. In my twenties, wanting to build something with my brother, we embarked on a joint venture. Our shared love for trivia, cultivated since childhood through TV shows and games, inspired us to create a trivia board game. Surprisingly, it found success, sparking my journey into entrepreneurship with one of my earliest ventures—a trivia app called FleetWit.

What is your company’s origin story? What is the biggest reason you started your business? What did those early days look like and teach you?
DM: One of my early ventures was a trivia app called FleetWit. It allowed people to play trivia games against each other for money. For the app, I needed two things. One, customers, and two, a way for customers to withdraw their money when they won. For customer acquisition, I did what most people did – spent money on Facebook and Google ads. For winnings withdrawal, I decided to offer digital gift cards, for an easy withdrawal method. Over time, I realized I was spending money to acquire customers through Facebook and Google, which obviously wasn’t 100% ROI. I thought, “There has to be a more efficient way.” I was on a mission to see if I could create a model where I only paid for the customers I acquired and help the gift card brands we were working with to make more money. I reached out to the brands directly and asked if they would pay to be a withdrawal option. They said yes and the rest was history. I went to my board and told them that I thought I had solved a huge problem for not just FleetWit but potentially for all brands, but that I wanted to pivot my focus on this new opportunity.

What do you wish you knew when you started? Is there anything you would do differently?
DM: Honestly, nothing. The mistakes are so important; they’re the stepping stones to success. In the entrepreneurial journey, you make a thousand missteps, and each one teaches you something crucial. They’re the hidden gems that shape your path. Without them, there’s no growth, no progress. They’re not just mistakes. Without the lesson, you wouldn’t have the wisdom you have today to make you better. No regrets.

What does “success” look like for you? We’d love to hear your biggest, boldest dream. What do you think will help you achieve it?
DM: Success changes with age. At this stage of my life, success means more than personal achievements; it’s about reciprocating the support and faith others have bestowed upon me. Throughout my journey, I’ve been fortunate to have a network of people—my teams, my family, my backers—who’ve invested in my vision. Now, I strive to deliver returns on their trust and dedication, to celebrate victories together. It’s a journey that demands persistence, ingrained in my very being, and yes, a sprinkle of luck. But luck, it’s said, favors the persistent. So, I keep swinging, knowing that with each attempt, I’m inching closer to hitting that home run. It’s about staying in motion, breathing through every challenge, and never losing sight of the goal.

What is your superpower as an entrepreneur? What is your proudest and darkest moment so far? Share a key high and a key low from your journey if you can.
DM: My superpower is, hands down, my resilience. My proudest moment has been witnessing my team’s growth and collective victories. Many of them have been by my side since the outset, and it’s immensely gratifying to witness not only their professional development but also the preservation of their core humanity. But, startup life isn’t all sunshine and rainbows. When things go south it’s tough, especially when it affects the team. Finding solutions that make everyone happy can be a real challenge. While I can weather the blows aimed at me, it weighs heavily on my heart when those around me are affected by the turbulence.

What are your personal driving principles, your top values?
DM: Treat others the way you want to be treated. Life is too short for anything less. I believe in embracing experiences over material possessions because let’s face it, no amount of money or material items can fill the void that real connections and meaningful experiences bring. Real wealth is having things that money can’t buy—love, laughter, memories, and relationships.

How have your personal principles and values shaped your company’s values and principles? Give us some examples.
DM: As a parent, I’ve learned that my kids will never do exactly what I say. But, they will observe and absorb my actions. It starts at the top and is about leading by example, setting the tone from the top down. In my professional life, I strive to cultivate a culture of empathy, adaptability, tenacity, and strong work ethic. These principles have served as the core pillars of how we’ve built our teams and built our products, fostering an environment where everyone has ownership and the ability to achieve great things.

What’s it like to work alone or with your partners?
DM: I consider myself an extroverted introvert, thriving on extremes in both directions. When I’ve had my fill of one, I instinctively crave the other. I prefer to keep my thoughts close until they’re fully developed and processed, which can admittedly be frustrating for my partners at times. However, this journey of self-discovery has taught me the importance of understanding one’s own needs. By recognizing and honoring these needs, I’ve become more effective in collaborating with others. It’s all about finding that balance and leveraging it to maximize productivity and harmony in teamwork.

What role does mentorship play in your world (as a mentor or mentee)? Tell us about what makes mentorship valuable to you and your business.
DM: Mentorship is valuable because it can come in all different forms. I’ve had mentors from all walks of life—some are board members, others investors, and a few are even family and friends. They each bring their own unique take on things, shaped by their own life experiences. Their insights have been absolute game-changers for Prizeout. They’ve opened my eyes to angles I never would’ve thought of on my own. Having this diverse crew of mentors is like having a bench full of superstars, not just relying on one MVP. It’s what keeps the game interesting and helps us keep scoring those wins.

Can you share some insights into the market or industry you operate in? How have you navigated challenges and changes in the market landscape?
DM: We work in the financial institution space, specifically with credit unions. Never in my life have I worked with such a collaborative, empathetic, and caring industry that truly cares about their members. It’s been refreshing and good for the soul. Initially, breaking into this world was no easy feat. These institutions wanted nothing to do with a former Wall Street guy and fintech startup founder. I vividly recall our first credit union conference— we were outsiders, met with suspicion and apprehension. However, through time, trust, patience, consistency, and a quality product, we gradually earned their trust. Fast forward to today, and our partnerships span the nation. Those once-daunting conferences have transformed into joyous reunions, where we are now welcomed with open arms, surrounded by familiar faces and shared success stories.

Many entrepreneurs continue to perfect their daily routines to support their work and greater vision; would you mind sharing your morning routine or a regular ritual that grounds your work each day?
DM: Unlike a lot of CEOs, I actually don’t function well with routine. Instead, I’ve found my daily anchor in something simple: my walk to work through the bustling streets of New York City. There’s something about being out in the open, whether on a call or lost in my own thoughts, that helps me find my balance each day.

How do you manage the work-life balance as an entrepreneur? What strategies have you found effective in maintaining your well-being?
DM: Maintaining balance is essential for overall well-being. Prioritizing relationships is a key part of that balance. Consider: who are the individuals you cherish spending time with the most? Make sure to carve out space for them. Nurturing those connections is vital for a happy, fulfilling life.

Where do you turn for inspiration?
DM: I’m not one to idolize billionaires or celebrities. In my view, they often lose touch with reality. Instead, I’m drawn to the unsung heroes—the ordinary people quietly doing extraordinary things. There’s something truly inspiring about discovering greatness in the everyday lives of regular folks.

Building and sustaining a business often involves overcoming various challenges. Can you share a specific moment where your entrepreneurial resilience was tested, and how did you navigate through it to ensure the sustainability of your business? What lessons did you learn from that experience?
DM: A defining moment of my entrepreneurial resilience was when both an investor and a celebrity I had a meeting set up with, ghosted after I had flown in for the meeting. Talk about shattering hope. I believe that hope is an entrepreneur’s most valuable asset, and when that is shattered, it teaches resilience. Now, as an angel investor myself, I’ve become more cautious and understanding when it comes to meeting with young entrepreneurs. and also learned the importance of maintaining irrational optimism in the face of adversity – especially when the odds seem stacked against success (which, 9/10 startups fail so often it is).

Do you have a favorite quote, mantra, or words of wisdom to get through the tough days?
DM:“The mass of men live lives of quiet desperation.” People often shy away from fear, obstacles, and the unknown. But I embrace the adventure. Whatever the outcome, I’m living life on my own terms, which could lead to great fortune and riches. Even if it doesn’t, I’m still leading an extraordinary life. It’s not the pursuit of happiness; it’s happiness in the pursuit!

What is a problem that keeps you up at night?
DM: What keeps me up at night are the uncertainties, the things I don’t know. However, I’ve cultivated a habit of always having a plan—from Plan A to Plan G. By methodically working backward from worst-case scenarios and asking myself, ‘Can I live with this?’ I often find reassurance. Empowerment comes from acceptance. I’ve learned that we tend to suffer more in our imagination than in reality. So, while the unknown may linger, I take proactive steps to plan for as much as possible.

How do you think about helping others through your work?
DM: In everything I do, my focus is on helping others; for me, that embodies the essence of life itself. I’ve found unparalleled joy in giving and assisting others. Admittedly, this mindset can leave one vulnerable, susceptible to hurt and disappointment. Yet, I firmly believe that people operate to the best of their knowledge and abilities. With each passing year, we accumulate wisdom, echoing Socrates’ sentiment: ‘I know nothing, therefore I know something.’ We’re all on a journey of growth, and I’m committed to continuing to lend a hand and pay it forward, recognizing that our purpose in life is to support one another.

Have you faced any significant crises in your business, and how did you manage and overcome them?
DM: As a CEO, navigating daily crises involving employees, investors, partners, and customers is a norm. To effectively manage these challenges, I categorize them into two distinct groups: reversible and non-reversible. The majority of crises typically fall into the reversible category, where decisions can be adjusted or altered as needed. However, it’s the non-reversible crises that demand meticulous consideration and strategic planning. These situations necessitate careful thought and precise action due to their lasting impact.

What kind of outside capital have you raised? What made you choose that route?
DM: I chose to raise from entrepreneurs and family offices – more untraditional routes. In my experience, I find that raising from fellow entrepreneurs suits me and the business – their firsthand experience equips them with a profound understanding of the entrepreneurial journey and the challenges involved.

Where do you meet investors?
DM: When you meet one person, you often open doors to others, as people enjoy involving their friends. It’s about building and nurturing a network that constantly expands. By treating others well and embodying strong character, you earn their trust and respect. This includes friends and family, who are integral parts of this network.

How has your network helped you raise capital?
DM: Social currency is our most invaluable asset. Within my network, I’m fortunate to be surrounded by individuals of both influence and exceptional character.

What advice do you have for fellow (and aspiring) entrepreneurs building and leading teams?
DM: So much advice is doled out to you when you are an entrepreneur. I’m an older entrepreneur, at this point in my life, this is what I would share with fellow and aspiring folks:

• Embrace The Journey: enjoy the process and cherish the individual moments. Success shouldn’t come at the expense of missing out on building something meaningful.
• Build a Supportive Network: Surround yourself with individuals who believe in your vision.
• Trust Your Instincts: Your instincts can often guide you in the right direction, even if you don’t have all of the information in front of you. Listen to that inner voice, especially when faced with critical decisions.
• Have Unyielding Determination: Strong resolve is a must if you want to go against conventional thinking and the inevitable chorus of criticism that always seems to be directed at those trying to do great things.
• Put Business First, Ego Second (or third, fourth, fifth, etc): Prioritize your business over your personal ego. The success of your business is paramount, and decisions should be guided solely by what is best for its growth.
• Craft Your Leadership Style: Leadership matters. The most successful entrepreneurs lead by example, avoid micro-managing their employees, and cultivate a drama-free environment.
• Have Irrational Optimism: An entrepreneur’s journey is never a straight line, and is often filled with extreme adversity – both on personal and professional levels. Believing that you CAN overcome a challenge will motivate you to find a solution, rather than languishing in despair and letting it overcome you. Ultimately it will be that irrational optimism that gets you through those dark moments.

What kind of an entrepreneur do you want to be known as – as in, what do you want your legacy to be?
DM: My goal is to become the best version of myself, authentically. Rather than crafting an image, I am committed to staying true to who I am. This means demonstrating unwavering resilience in navigating challenges, advocating for balance in every business interaction, and consistently prioritizing the well-being of others above my own interests.

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