This Serial Entrepreneur Raised $64 Million To Enable Users To Withdraw Rewards From Partner Platforms And Receive Bonuses
Entrepreneurship didn’t start for David Metz in a pitch deck or a startup accelerator; it started at the dinner table. Growing up on Long Island, New York, David watched his parents run an irrigation business.
The family wasn’t talking about “runway” or “unit economics,” but the lessons were far more visceral. There were years when Christmas presents were skipped to keep an employee on payroll. Hard tradeoffs weren’t theoretical; they were normal.
Risk wasn’t something to be debated; it was something you lived with. That upbringing shaped how David would later approach building companies, raising capital, choosing partners, and defining success.
Today, as the founder and CEO of Prizeout, a fintech platform that powers rewards and monetization programs for financial institutions, David has raised over $64M and built a company on the brink of profitability. But his journey there was anything but linear.
Entrepreneurs Are Both Born and Made
David believes entrepreneurship is part nature, part nurture. Some traits, especially risk tolerance, aren’t learned. You either have them, or you don’t. But understanding what sacrifice looks like, what ownership feels like, and how responsibility compounds over time? That’s learned through exposure.
Growing up in a blue-collar town, David didn’t know doctors, lawyers, or executives. Entrepreneurship was the only path he saw. What many people view as “crazy risk,” he saw as normal behavior.
That perspective would later enable him to weather failures, pivots, and uncertainty without flinching, especially given that 9 out of 10 startups fail, as David points out.
From Division I Lacrosse to the Startup Locker Room
Before startups, David was an athlete. He played Division I lacrosse, and the sport’s competitiveness left a permanent imprint. Today, he compares closing deals and hitting milestones to the adrenaline of winning games, but what he misses most isn’t the field; it’s the locker room.
That sense of camaraderie, shared goals, ambition, and collective accountability is something David has deliberately recreated at Prizeout. He views a startup team as the modern-day version of a sports team: everyone has a role, everyone shows up prepared, and winning occurs only when the group functions as a unit.
The First “Startup” Before He Knew What One Was
David’s first entrepreneurial venture didn’t have an LLC, a board, or legal compliance. In college, during the late-1990s market boom, he worked for a financial advisory firm, when the stock market was going through a tumultuous period.
David navigated the challenges exceptionally well and convinced financial advisors to give him, a 19-year-old, access to their Ameritrade accounts—before he had any knowledge about how hedge funds worked. In exchange, he kept 20% of the profits.
It was wildly informal—and definitely against every SEC rule imaginable—but it taught David foundational lessons: how to sell trust, how to execute under pressure, and how to handle tough conversations when trades didn’t go well.
At the time, David had zero experience, but it became his first entrepreneurial journey. He didn’t have an LLC, but was doing sophisticated trading by simply learning on the job. Without realizing it, David was learning what it meant to manage other people’s money and expectations.
Flugpo, Craigslist, and Surviving the 2008 Crash
After working on Wall Street, David launched Flugpo, an online classifieds platform with social trust features layered onto the Craigslist model. As he recalls, in the mid-2000s, Craigslist was the go-to platform for everything, from reaching the fire department and selling a couch to going on a date.
At its peak, Flugpo reached over 1.5 million listings, primarily in New York. Then 2008 hit. Funding vanished overnight, and the company exited for a nominal sum via an acquihire. While the outcome wasn’t a financial home run, it was decisive.
David had crossed the point of no return. He could never go back to working for someone else. More importantly, he learned that not all exits are failures. Getting to the finish line—however imperfect—is still an outcome, and the lessons compound.
As David points out, acquihires today are driven by substantial returns because many deals are structured around AI, a new industry. Back then, acquisitions centered on the assets and people, though acquirers didn’t keep everyone on the payroll.
However, today, acquihires can be highly profitable because the skills people have, particularly in AI, are extremely valuable. Merger and acquisition deals worth $300M are being executed, a drastic change from the time David sold Flugpo.
The Hidden Cost of Building With Family
David later launched a board game company with his brother, selling over 30,000 units. On paper, it was working. In reality, it surfaced as one of the hardest lessons of his career. At some point, success shifts the conversation—from creativity to money, from experimentation to long-term expectations.
David faced a choice: maximize the opportunity or preserve the family relationship. He chose family. Entrepreneurship and family, he learned, operate in different emotional systems. When work enters the home, boundaries erode.
Home should be a sanctuary, not an extension of the office. Walking away was painful—but it was the right decision. Thousands of homes today still have their board games—and David considers that a significant win.
FleetWit, IP Risk, and the Pivot That Changed Everything
David’s next company, FleetWit, was a skill-based trivia gaming app where users wagered money on their knowledge. The game had hundreds of categories, from sports to history, and one of the most popular, Harry Potter. FleetWit scaled quickly, doing roughly $1M in Gross Merchandise Value (GMV).
Then Warner Bros. sent a cease-and-desist because they were using its intellectual property. When copyrighted categories like Harry Potter and Friends were removed, customer acquisition costs spiked. Growth slowed. But inside the problem was an insight that would change David’s trajectory.
Winners withdrew their earnings via digital gift cards. At the same time, David was spending heavily on Facebook ads to acquire users. He realized something critical: brands like Nike or Olive Garden were effectively acquiring customers for free through gift card withdrawals.
That insight led to a bold decision. David shut down FleetWit and transferred all investor equity to the new venture, even though he wasn’t legally required to. That venture became Prizeout.
Prizeout: Turning Cost Centers Into Profit Centers
Prizeout started as an alternative withdrawal method for gaming platforms, using gift cards to monetize the process. Instead of PayPal or ACH, users could withdraw winnings as digital gift cards—with a bonus. Win $100, get $110 at Nike or $120 at Cheesecake Factory.
Partners benefited too, as Prizeout paid them a share of the revenue. Where withdrawals were traditionally a cost center, Prizeout turned them into a profit through revenue sharing. For some partners, that meant millions in incremental revenue.
Over time, this model evolved into full-scale rewards programs for financial institutions, including major credit unions.
A Different Philosophy on Fundraising
David has raised approximately $64M, but he’s not a fan of traditional VC fundraising. Not because VCs are bad, but because early-stage companies need empathy more than theory. In his opinion, early in their entrepreneurial journey, founders need to partner with people who have felt their pain.
Storytelling is everything that David Metz was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Peter Thiel, Silicon Valley legend (<a href=" target="blank" rel="noopener">see it here</a>), where the most critical slides are highlighted.
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David prefers raising from former founders, operators, family offices, and strategic partners—people who’ve lived through near-death moments, not just studied them. As he sees it, entrepreneurs raise funding to align with the typical company life cycle, which matures every 18 to 24 months.
At that point, companies need other things in parallel to the financing cycle, such as know-how and networks. David focuses on the value his investors bring to the table, other than just capital. He wants partners who invest and thus have real skin in the game and actually use the products.
In Prizeout’s Series C, the round was led by 21 credit unions, many of them active partners with $30B assets under management (AUM). Capital and distribution arrived together. Incentives were aligned, though, as David concedes, different models may require different forms of funding.
But now that Prizeout is close to profitability, it is in a position to control its own destiny. Even so, David understands the importance of funding when conditions are uncertain. Having money in the bank, even though you don’t need it, is preferable to needing funding and not having it.
If that happens, companies lose leverage, and that factor is reflected in the terms they accept and other aspects of fundraising. David’s operates on two core principles. Firstly, always raise double what you actually need. And secondly, become profitable quickly.
The Stories That Matter When Things Get Hard
David values investors not just for introductions, but for perspective. He raises from people who understand the entrepreneurial journey and can drive real value for the company. What is he looking for? Two things:
Intros: Once an investor writes a check, they have the inherent motivation to help. An investor writing big checks will likely have a significant network that David proactively leverages. · Advice: As the CEO, David understands that he has two jobs—one is working internally with his employees. And the second is working externally with the board and his investors, who are also entrepreneurs.
Hearing stories of founders who risked their homes, brought their spouses into bank meetings, and still pushed forward despite the risks creates a powerful realization: you’re not alone. David learned that the investors who had money did not have an easy path to making that money.
That emotional validation—the reminder that struggle is part of the path—is often more valuable than capital itself.
His Vision And Advice for His Younger Self
David describes Prizeout today as a gifted three-year-old: capable of impressive things but still needing care. His long-term goal isn’t control—it’s obsolescence. Success, to him, is walking into work one day and realizing the company doesn’t need him anymore.
The ultimate dream? Years after an exit, former employees gather at a bar, sharing stories of the companies they’ve built and the careers they’ve launched—because Prizeout was their springboard.
If David could give 21-year-old David one piece of advice, it wouldn’t be tactical. It would be simple: start earlier. In your 20s, you need very little. A futon and ramen are enough. As life accumulates responsibilities, risk becomes heavier.
Entrepreneurship rewards early experimentation—and the only real way to learn is by doing.
In Conclusion
David Metz’s journey isn’t a highlight reel. It’s a compounding story of sacrifice, pivots, integrity, and long-term thinking. And it’s a reminder that the most durable companies aren’t built by chasing shortcuts—but by people willing to learn the hard way, again and again.
Early exposure to sacrifice made risk feel normal, which became David Metz’s operating system as a founder. · Entrepreneurs are both born and made: risk tolerance is innate, but resilience and ownership are built through lived experience. · The “locker room” matters: winning in startups comes from team chemistry, shared accountability, and competitive execution. · Trust is a founder skill: from managing others’ money at 19 to leading companies, credibility is built by performing under pressure. · Not all exits are failures: even an acquihire can be a finish line that compounds into future leverage and better judgment. · Family + business blurs boundaries fast, so protecting relationships can be the highest-ROI decision you make. · Prizeout was born from a pivot insight: turn a withdrawal cost center into a profit center, then fund growth with investors who bring empathy, distribution, and real skin in the game.
Original Version
Alejandro Cremades: All righty, hello everyone and welcome to the DealMaker Show. So today we have a founder that has done it multiple times. you know There's gonna be quite a a bit of lessons learned that we're gonna be discussing in quite the story. We're gonna be talking about building, scaling, financing,
Alejandro Cremades: You name it. Also starting companies with family members, you know, transitioning from different fields, you know, segments. A lot of really good stuff. Brace yourself for a very inspiring conversation.
Alejandro Cremades: Without further ado, let's welcome our guest today, David Metz. Welcome to the show.
Alejandro Cremades: So originally born and raised in Long Island, New York. Give us a walk through memory lane. How was life growing up for you?
David Metz: Awesome. um Grew up, parents, um still together, still alive, knock on wood. Older brother, younger brother. My parents were entrepreneurs themselves. They owned an irrigation business.
David Metz: So I definitely grew up knowing, well, not knowing what entrepreneurial was, but knowing um the work that it took to get them where they got to. So I was kind of always steeped in what entrepreneurialism meant and is.
David Metz: It's a good question. um Probably a little bit of both. I think risk tolerance is not something that's learned. You either have it or you don't, and you certainly need it to be an entrepreneur.
David Metz: um Also what it takes, right? Like my parents sacrificed a ton, right? I saw, you know, there were, there were Christmases where we didn't get Christmas presents because it was a choice whether to you know keep somebody on payroll or let them go. right So seeing those hard decisions, it became normal for me. like I thought that is how everyone, you know not until I grew up and I grew up in a pretty blue collar town.
David Metz: I never knew doctors or lawyers or execs that didn't exist where I lived. So, you know, that was ah the entrepreneurialism was the only way that I knew. So definitely it would became more normal to me where for most people, the risks that most entrepreneurs take is probably seemed crazy, especially when you look at the out, it's like nine out of 10 startups fail and all of that.
Alejandro Cremades: Now, for you, obviously, um you know, you you were quite competitive. You played lacrosse and that really got you through college and all of that.
Alejandro Cremades: I guess that competitiveness, how do you think that has served you, you know, also when it comes to ambition and and having your own projects?
David Metz: um I am 48 now, so my athletic career is way behind me. um The closest thing that I get to those highs of wins um is when you close a deal or you something big happens company, right? It's it's pretty similar. But if you ask me if I could go back to 19-year-old David when I was playing Division I lacrosse, would I rather be in the locker room or on the playing field?
David Metz: It's probably the locker room, you i mean? That team camaraderie and having a team here at Prizeout is the closest thing to having that locker room, you know having a goal and achieving something together and everyone doing their job.
David Metz: so um And also it helps to be competitive, right? Because you want to win. um But, you know, I've tried to replicate my experience in athletics here at the company, right? And there's a lot of things that are similar to that experience.
Alejandro Cremades: And we'll talk about the company in just a little bit. But obviously, there's a couple of things, you know, they are leading into it. I mean, you've started a few companies. So right out of college, you went to Wall Street, you know, you got your your your chops there.
Alejandro Cremades: And then eventually you started your first business. So walk us through what were the sequence of events there and until you were like, you know what, I'm going to I'm going to test this thing out of launching my own thing.
David Metz: Yeah, I've always done entrepreneurial things. When I was in college, I worked for a financial advisory firm. And this was at like 99, 2000, when stock market was going crazy. um And I was kind of doing stock market challenges and doing well.
David Metz: And I started talking to some of the financial advisors and they're like, wow, you're you're really doing well. So I somehow convinced them, you know, being 19 to give them give me their money in the form of give me access to your Ameritrade account.
David Metz: And I would trade it for them and they would give me 20% of their profits. And I was managing in college about 20 of those Ameritrade accounts. Nothing of that is legal. I'm sure it goes against like every SEC law, um but I did quite well.
David Metz: um And from there, you know, not having any experience whatsoever, um I wanted to learn properly how to be a trader, but that was my first kind of journey. entrepreneurial thing.
David Metz: Number one, I had to sell them, right? Convince a 19-year-old to give me access to your merit trade, right? I came up, this is before I knew what two and 20 in the hedge fund world was.
David Metz: So the 20% was by accident and I had to execute, right? And when things, you know, when I didn't have a good trade and they're like what happened? Like, I had to have tough conversations.
David Metz: Right. So that was my first kind of, you know, official startup.I didn't have an LLC or anything like that. but I was doing a sophisticated thing that I was just kind of finding my way into.
David Metz: So that was really my first. And then post working on Wall Street, I had an idea for online classifieds. I'm sure you remember this, but you know in the mid 2000s, Craigslist for was everything. You want a fire apartment, you want to sell your couch, you you want to go on a date. Literally, it was taking the newspaper model and bringing it online. I don't know if you've been on Craigslist
David Metz: It has not changed. It is literally the same thing. So anyway, I took that model and I just added like a social element to it um where there was reviews and things like that because it you know if you someone said they were going to buy your couch, you trusted them that they were gonna come in your apartment and not kill you, right? So that was called Flugpo.
David Metz: think at our height, we had like over 1.5 million listings, predominantly in the New York area. um And then unfortunately that I started in 06, 08 happened.
David Metz: Right. um And then like funding and everything like that happened. So we exited at a nominal amount, but it was my first real taste of being an entrepreneurial. And then once, you know, once I had that, it was never looking back. I could never go back and, and work for a company again.
Alejandro Cremades: I mean, I think that at the end of the day, you know, ah um an outcome where you're able to get it to the finish line, you know, it's it's still an outcome. And, you know, there's still like great lessons, you know, to take away with you. I guess in this case, as you were mentioning, an aqua hire. Now, an aqua hire, how should people, especially all the founders that are listening now, how should people think about aqua hires?
David Metz: Yeah, it takes on different meanings, I think, throughout the decades because Aqua hires all the rage right now. But the Aqua hires that are happening now are for real money because a lot of it is built around AI, right? Because AI is such a new industry.
David Metz: there's not much talent. Nobody went to school for AI, right? Most of it is self-learned. So back then, it was more for the assets and people, right? And then you're usually not keeping everyone. Nowadays, acquihires can be really profitable because the skill set that the people have and specifically towards AI are really valuable. There's companies getting bought by two, $300 million dollars in acquihires, right? Because that talent is real. so it's definitely changed from then than it is today.
Alejandro Cremades: So after that, you know you went at it with your brother. So you guys started a board game and you saw like 30,000 units or so. I mean, it was saying you know heading in the right direction.
Alejandro Cremades: But but i mean you saw the business with your parents, their irrigation system that they own in Long Island, and the experience you know with your brother, perhaps you know like you got a different type of taste.
Alejandro Cremades: Or what did you get from that? I mean, how was that for you guys?
David Metz: Yeah, I think one of the reasons you we started it was we were both kind of not doing anything. So let's do something together. Right. And then as it grew and got more and more success, you know it just becomes more about the future, the money and things like that.
David Metz: And it came to a point where it's like, what do I value more, the potential or my relationship with my family? And in this case, I chose my family.
David Metz: You know, people always say never go into business with family.
David Metz: And like, you always think that, oh, they're talking about somebody else, not me. And it's it's neither negative about family members. It's just like, It's two different worlds. Right. And honestly, my parents had a company together and there were a lot of you know arguments at the dinner table and all of that. Right. Like when you come home, you want to talk about other things, not work. Right. Home should be your sanctuary. Right. You should leave work outside of it. Right. Any times you kind of invite family members in it.
David Metz: the waters just get muddied, right? So, you know, that was a lesson that I learned. And I think both me and my brother learned that lesson. So we both decided like, it's better to just kind of move on from it and take the experience, which was incredible.
David Metz: You know, there's, you know, you know, thousands of people's homes right now that have our board game.
David Metz: And that's pretty cool. And certainly check something off our bucket list.
Alejandro Cremades: Now, after this one, the next one, it was FleetWid. Now, with FleetWid there, you guys had, um you know, basically like a trivia app. And essentially, you guys raised some money.
Alejandro Cremades: You were doing about a million bucks a month. And then all of a sudden, you woke up a giant a giant, Warner Brothers, and came in knocking.
Alejandro Cremades: And obviously, that changed everything. But also, it was a really nice immediate step, you know, for you to end up landing, you know, with what you're doing now with PriceOut. So, walk us through what happened there.
David Metz: Yeah, so we were having a lot of success. Essentially, the premise is pretty simple. You could challenge friends or so or strangers in online trivia through an app.
David Metz: But the catch was that you would wager money, right? So skill-based gaming and the skill was how much do you know? And there were hundreds of categories, everything from sports to history. But one of our most popular categories were things like Harry Potter, right?
David Metz: Or friends, right? So, we'd ask questions from the movies and TV show and it's super duper popular and was one of the biggest levers of growth. And then one day we got an email from Warner Brothers saying, cease and desist, you're using intellectual property.
David Metz: um And that was kind of like, whoa, right? So when we had to turn off those categories, our CAC started to increase significantly. So we had to start asking questions.
David Metz: um But what was interesting is one of the things that happened while I had that app was people would win money and they needed a way to withdraw their earnings and they would do it through digital gift cards.
David Metz: Um, and on and the same side, i was spending a ton of money on Facebook, acquiring users. But over time I kind of realized is like, wait a second, every time someone wins money and they withdraw their money to Nike gift card or to, ah Olive garden whatever it might be, those companies were essentially acquiring a user. So I thought there was a huge opportunity there. So I went to my board and I said, don't kill me, but we're going to close down.
Alejandro Cremades: Investors, customers, and employees are all betting on the future and the vision. If you woke up tomorrow in a world where Prizeout’s vision is fully realized, what would that world look like?
David Metz: I describe where we are like a three-year-old child. Imagine a three-year-old climbs onto a piano and starts playing Mozart. You think you have a virtuoso. But the child still needs diapers changed, food, and care.
David Metz: I think we’re leaving that stage. One day I’ll walk out of the subway on my way to work and realize the company doesn’t need me anymore. If I weren’t here, it would just keep going.
David Metz: My more selfish dream is that years after an acquisition, former employees get together, rent out a bar, and catch up on what everyone’s doing. This person is leading a company, that person started one.
David Metz: If Prizeout was the springboard that launched all of that, that would be an incredible outcome.
Alejandro Cremades: Looking back with reflection, if you could stop your younger self just before starting out and give one piece of advice, what would it be?
David Metz: There’s a saying—Oscar Wilde or Mark Twain—that goes, “I’m not young enough to know everything.”
David Metz: The hardest part would be getting my younger self to listen. I’ve always learned best through experience.
David Metz: If I could give one piece of advice, it would be to start earlier. In your twenties, you need very little. You can survive on a futon and ramen.
David Metz: As you get older, responsibilities grow. Your parents want you to live a risk-free life. But if you’re going to do this, start earlier.
Alejandro Cremades: David, for people who want to reach out or learn more about Prizeout, what’s the best way?
Alejandro Cremades: Easy enough. David, thank you so much for being on the DealMaker Show. It’s been an absolute honor.
