Founder: Dennis Hensley 
Business: You Don’t Know My Life! 
Revenue/Month: $2.5K 
Founders: 2  
Employees: 0 
Website: youdontknowmylife.com 
Location: Los Angeles, California 
Founded: 2018 

You Don’t Know My Life! is more than just a party game. It’s a catalyst for connection, laughter, and unexpected revelations, cleverly disguised as a deck of cards in a brightly colored box. With questions designed to coax out the kinds of stories that are often saved for close friends—or never told at all—it combines humor and heart in a way that’s equal parts entertaining and disarming. Co-creator Dennis Hensley, a seasoned entertainment journalist, describes the game as “part diary entry, part group therapy, part comedy show,” a combination that invites players to open up in ways they might not expect. 

“I’ve always loved asking people questions that make them light up or laugh or even tear up,” Hensley explains. “This game takes that to another level. It’s like your favorite dinner-party conversation, only now everyone’s playing along, and there are points involved.” 

Hensley’s skill in crafting conversation-starting prompts didn’t come out of nowhere. His career as a writer saw him interviewing A-listers like Madonna and George Clooney, which he says taught him how to ask questions that disarm and delight. “When you’re interviewing someone famous, you have to find a way to stand out,” he recalls. “I learned to ask questions that felt fresh—things they hadn’t been asked a hundred times already. That’s the same energy we bring to the game.” 

One of the game’s standout cards asks players to share something they used to believe as a kid but later realized wasn’t true. Hensley says this prompt, in particular, never fails to get people talking. “We’ve heard everything from ‘I thought the world was black and white until the ’60s’ to ‘I thought pineapples grew on trees,’” he shares with a laugh. “It’s silly, but it also gets people thinking about their childhood and sharing pieces of themselves they don’t usually bring up.” 

Hensley and his collaborator, Jeb Havens, originally designed You Don’t Know My Life! for in-person gatherings, but the pandemic pushed them to pivot in unexpected ways. When lockdowns began in 2020, the duo started hosting Virtual Game Nights over Zoom, turning what could have been a tough break for the brand into an opportunity. “It was a way to keep the game alive while people were stuck at home,” Hensley says. “But it also became something more—it showed us how powerful this format could be for remote team-building.” 

Companies quickly caught on to the idea, booking Virtual Game Nights to help employees bond while working apart. Hensley recalls one event with a group of coworkers who hadn’t seen each other in over a year. “At first, everyone was kind of stiff, like they were still in work mode,” he says. “But by the second round, people were laughing, sharing stories, and connecting in a way you just don’t see on a regular Zoom meeting. It was amazing to watch.” 

The shift to virtual events added a new revenue stream to the business, alongside sales of the physical game. While $2,500 a month might not seem like a huge sum, Hensley emphasizes that the real value lies in the connections the game fosters. “We’ve had people tell us, ‘I learned something new about my spouse after 20 years of marriage’ or ‘I finally got my teenager to put their phone down and talk to me,’” he says. “That’s what makes it worth it.” 

For Hensley, who spent years writing feature stories for glossy magazines, the transition to game design feels like a natural evolution. “At the end of the day, it’s all storytelling,” he says. “Whether I’m writing about someone else’s life or helping people tell their own stories, it’s about creating a space where people feel seen and heard—and maybe even a little bit entertained.” 

From Questions to Connection: The Birth of a Game 

Before it became a go-to for breaking the ice and sparking laughter, You Don’t Know My Life! started as an experiment in storytelling. For Dennis Hensley, whose career as an entertainment journalist trained him to dig deep into people’s lives, the idea for the game grew naturally out of his gift for asking the right questions. But transforming that talent into a product required years of exploration, experimentation, and, as he puts it, “a little bit of luck and a lot of collaboration.” 

Hensley’s foray into storytelling took on a new dimension when he launched his podcast, Dennis Anyone? The show featured The Observation Deck, a recurring segment in which guests would pull a card with a prompt designed to reveal something unexpected. “The questions were always a little quirky,” he explains. “Things like, ‘What’s the worst thing you’ve ever thrown up?’ or ‘What movie made you cry at the wrong time?’ They weren’t standard interview questions—they were designed to make people stop and think for a second before they answered.” 

The responses were surprising, heartfelt, and often hilarious. “People would tell stories they hadn’t thought about in years,” Hensley recalls. “I started realizing that these prompts were more than just a fun way to fill time—they were creating real connections.” That realization planted the seed for a larger idea, though it would take a few more years before it fully took shape. 

Around 2017, Hensley found himself at a crossroads in his career. The entertainment industry, which he’d been part of for decades, was shifting. Seeking clarity, he turned to career programs offered by The Actors Fund, where he took courses in entrepreneurship and financial management. “Those classes were a game changer,” he says. “They gave me the tools to think about my skills in a new way and the confidence to explore something outside my comfort zone.” 

One of his first post-journalism ventures was Lifecast, a service where he conducted long-form interviews to preserve personal histories. Incorporating The Observation Deck questions into these interviews was a natural fit—and the feedback was overwhelmingly positive. “People kept telling me how much they loved the questions,” Hensley says. “It was clear that there was something special about the way they got people to open up.” 

This growing confidence in the concept collided with opportunity when Hensley reconnected with his friend Jeb Havens, a game designer. Their collaboration turned an idea into something tangible. “Jeb had the technical know-how to take these questions and turn them into a game,” Hensley says. “We started with the prompts and then figured out how to make it fun to play, not just fun to answer.” 

The process of refining the game was anything but casual. Over the course of eight months, the pair tested questions with friends, streamlined the rules, and developed prototypes. “We’d playtest with small groups, and I’d be sitting there with a notebook, taking notes on what worked and what didn’t,” Hensley says. “It was a lot of trial and error, but every time we made a change, the game got better.” 

In June 2018, the pair launched a crowdfunding campaign to produce the first 1,000 copies. “We didn’t know what to expect,” Hensley admits. “It’s always a little scary putting something out into the world. But the response was incredible.” By the end of the campaign, they had not only hit their funding goal but also built a base of enthusiastic supporters eager to get their hands on the game in time for the holidays. 

Hensley credits those early backers with validating the project. “It was one of those moments where you think, ‘Okay, this is real now,’” he says. “People didn’t just like the idea—they believed in it enough to support it. That gave us the momentum to take it further.” 

From Concept to Launch: Building a Game from the Ground Up 

Turning You Don’t Know My Life! from an idea into a fully realized product required more than creativity—it demanded a steep learning curve, resourcefulness, and an eye for detail. For Hensley and Havens, every choice, from the design process to manufacturing, played a role in shaping the game into what it is today. 

Although Hensley’s background as a journalist gave him a strong foundation in storytelling, entering the world of game development brought entirely new challenges. Early on, the duo focused on creating a visually engaging product that matched the game’s playful, irreverent tone. “We wanted the design to immediately tell you, ‘This is going to be fun,’” Hensley says. To bring this vision to life, they hired a freelance artist via Fiverr to create whimsical illustrations and doodles, while Havens handled the overall graphic design. 

Feedback from playtesting sessions became critical. “We’d play with friends, and their reactions told us what was working and what wasn’t,” Hensley explains. These sessions helped refine the structure of the game, ensuring it was intuitive while keeping the questions at the heart of the experience. 

When it came time to manufacture, they partnered with Longpack Games, a China-based production company known for its high-quality board games. Seeing the finished prototype for the first time was a turning point. “Holding that first copy in my hands was like, ‘Wow, this is real,’” Hensley recalls. 

Crowdfunding and the Power of a Deadline 

To fund production, Hensley and Havens took a grassroots approach to crowdfunding. Unlike Kickstarter or Indiegogo, which can require substantial resources to manage, they relied on their personal networks and social media to raise $12,000—the amount needed to produce the first 1,000 copies. The self-imposed goal of delivering games by Christmas 2018 added a sense of urgency that kept the team focused. 

“Deadlines are powerful motivators,” Hensley says. “We knew people were ordering the game as gifts, so there was no wiggle room. We had to deliver.” 

In addition to production costs, they allocated part of their budget to legal protection, including copyrighting the game and trademarking its title. “That was non-negotiable for us,” Hensley explains. “We wanted to make sure our intellectual property was protected from the start.” 

Another unexpected expense came when they decided to purchase their website’s domain name at auction. “We didn’t think we’d get it, but we ended up winning for $10,” Hensley laughs. “It was a tiny expense, but it made a big difference—it just felt like everything was falling into place.” 

When the first shipment of games arrived, the duo was ready. They had pre-addressed hundreds of envelopes to ensure orders could be shipped immediately. Hensley recalls the satisfaction of seeing their idea come full circle. “It was such a whirlwind, but knowing those games were heading out into the world—it made all the stress worth it.” 

Shifting Gears with Virtual Game Nights 

While boxed game sales initially drove the business, the pandemic shifted their focus entirely. With traditional gatherings on hold, Hensley and Havens quickly pivoted to hosting Virtual Game Nights, a move that brought new opportunities to their venture. 

“We were figuring it out as we went,” Hensley says. Havens developed a web app that worked seamlessly with Zoom, making the experience interactive and polished. Meanwhile, Hensley embraced his role as host, infusing each session with humor and charm. “It felt like being part emcee, part therapist, and part cruise director,” he jokes. 

Initially offered on a pay-what-you-can model, Virtual Game Nights generated $10,000 during the first year of the pandemic. As demand grew, partnerships with platforms like Elevent and Amphy allowed the team to expand their reach. Corporate clients, ranging from small startups to global companies, began booking sessions for team-building events. “We’ve had people playing from six different time zones in one game,” Hensley says. “It’s wild to think about how far it’s come.” 

Each event brings in $360 for 90 minutes of gameplay, with clients often requesting repeat bookings. “It’s not just about the game—it’s about the experience,” Hensley explains. “People leave feeling more connected, which is exactly what we hoped for when we started this.” 

Creative Marketing and Future Ambitions 

Throughout their journey, Hensley and Havens have explored diverse ways to promote You Don’t Know My Life! From leveraging Hensley’s podcast audience to landing features in holiday gift guides, their marketing efforts have been as varied as the stories shared during gameplay. 

“One of our favorite things was creating a word cloud from customer reviews,” Hensley says. “It was such a cool visual representation of how people were responding to the game—and it made for great social media content.” 

Not every effort has been a home run. Hensley acknowledges that some experiments, like Facebook ads, didn’t deliver the results they hoped for. Still, the duo has had major wins, including a deal with a TV production company to adapt the game into a televised format. While the project hasn’t been greenlit, the experience reinforced their belief in thinking big. 

For Hensley, the journey has been as rewarding as the product itself. “This game started as a way to get people talking,” he says. “But seeing how it’s evolved—and how much joy it’s brought to people—that’s what makes it all worthwhile.” 

Expanding Horizons: What’s Next for You Don’t Know My Life!? 

As the dust settles on the upheaval of the past few years, Hensley and Havens are doubling down on what works while looking ahead to new opportunities. Virtual Game Nights have not only provided stability but also become the centerpiece of their business. However, they see the future as a blend of what’s proven and what’s possible, combining online events with plans for more in-person engagement. 

“We’re thrilled with how the virtual side of things has taken off, but there’s nothing quite like being in a room full of people, watching them light up as they share their stories,” Hensley says. With Elevent now booking in-person events, they’re preparing to bring the energy of their online experiences back to the physical stage. These sessions, aimed primarily at corporate clients, will offer a more intimate, interactive setting while preserving the humor and camaraderie that define the game. 

The pivot to live events isn’t entirely new. Before 2020, they had already tested the waters with small on-site gatherings, and the positive reception fueled ideas for future expansions. “There’s something magical about seeing a team of coworkers who’ve barely spoken to each other suddenly laughing and connecting over shared stories,” Hensley explains. “That’s the kind of experience we want to bring back, but on a bigger scale.” 

A Business That Transforms Pressure into Freedom 

While You Don’t Know My Life! has been a financial success, for Hensley, its impact extends far beyond the numbers. The game has given him a creative outlet that feels both fulfilling and empowering. “When you’re working in industries like journalism or entertainment, there’s so much that’s out of your hands,” he reflects. “This business gave me something I could own completely, where every decision is mine to make.” 

Hensley shares that having a steady stream of income from the game has also allowed him to approach his writing projects with a lighter heart. “It takes the pressure off,” he says. “When you’re not worried about how the bills are going to get paid, you can actually enjoy the creative process.” 

Their vision for the future is both bold and strategic. Beyond the in-person events, Hensley and Havens are exploring other ways to extend the brand’s reach. The idea of turning You Don’t Know My Life! into a television show remains on their radar, as does a potential collaboration with major retailers like Target or Walmart to bring the game to a broader audience. 

At the same time, they’re careful to stay grounded. “We don’t want to lose sight of what’s already working,” Hensley says. The Virtual Game Nights, which have proven to be both profitable and impactful, continue to drive their efforts. Yet they remain open to evolving the business in ways that feel authentic to its roots. 

For Hensley, the entrepreneurial journey has been a deeply personal one. “This is the first time I’ve created something that feels entirely mine,” he says. “It’s not just about the game—it’s about having control over my own path. That’s what makes it so special.” 

Sharing the Experience: Lessons for Aspiring Entrepreneurs 

For Hensley, building You Don’t Know My Life! has been as much about personal evolution as it has been about business strategy. Turning an idea into a product, refining it, and sharing it with audiences worldwide has taught him lessons that extend far beyond the scope of game design. Chief among them is learning that progress consistently trumps perfection. 

“Too many people get stuck obsessing over tiny details—like whether the logo is exactly right or the tagline is perfect—and they never actually launch their idea,” Hensley says. His approach has been to prioritize action over hesitation, focusing on moving forward even if every piece isn’t flawless. “You can always tweak things later. The most important step is to just get it out there.” 

This philosophy was instrumental in the early days of the business, helping them avoid analysis paralysis and instead focus on testing and improving as they went. It also proved invaluable during the pandemic, when quick action allowed them to pivot to Virtual Game Nights. “If we’d waited until we had all the tech or tools perfectly in place, we’d have missed the moment entirely,” Hensley reflects. “Instead, we jumped in and figured it out along the way.” 

Creating Connection Through Play 

While Hensley initially viewed the game as a way to channel his love of storytelling, what has surprised him most is the emotional impact it has on players. Each session, whether virtual or in person, creates opportunities for people to share stories, laugh, and occasionally reveal sides of themselves they hadn’t expected. “It’s not just about having fun,” he explains. “It’s about creating moments where people connect in ways they wouldn’t otherwise. That’s the real magic of the game.” 

Hensley recalls one particularly touching moment during a Virtual Game Night with a corporate team spread across different time zones. “There was this one player who shared a story about a challenge they’d faced growing up, and you could feel the energy in the Zoom room shift,” he says. “It was one of those moments where you realize that even something as simple as a game can create space for people to really see each other.” 

More than just a business, You Don’t Know My Life! has become a platform for fostering joy, empathy, and understanding. Hensley says that every time he finishes hosting a game, the experience reaffirms why he took the leap into entrepreneurship. “It’s incredibly satisfying to know you’ve created something that brings people closer together,” he says. “At the end of the day, that’s what makes it all worth it.” 

Success Factors: Why Did You Don’t Know My Life! Succeed? 

• Strong Storytelling Foundation: Dennis Hensley’s background as an entertainment journalist and podcaster equipped him with the skills to craft compelling, thought-provoking prompts. His expertise in asking unique, engaging questions became the cornerstone of the game’s appeal, encouraging players to open up and connect. 

• Adaptability and Willingness to Pivot: When the pandemic disrupted traditional sales and in-person gatherings, Hensley and Havens pivoted quickly to Virtual Game Nights, turning a challenge into an opportunity. Their ability to innovate on the fly and embrace new formats, such as Zoom-based events, kept the business relevant and profitable. 

• Focus on Action Over Perfection: Hensley’s philosophy of prioritizing progress over perfection enabled them to get the game to market efficiently. Instead of getting bogged down in details, they focused on testing, refining, and improving the product over time. 

• Grassroots Crowdfunding and Budget Management: By raising $12,000 through a grassroots campaign instead of relying on resource-heavy platforms like Kickstarter, they were able to fund production without overextending themselves. Their careful allocation of funds for essentials like manufacturing, legal protections, and marketing was another critical factor. 

• Collaborative Expertise: The partnership between Hensley and Havens blended complementary skills—storytelling and technical game design. Havens’ expertise in graphic design and game development brought structure and visual appeal to the product, ensuring it resonated with audiences. 

• Customer-Centric Approach: Playtesting sessions with friends and early supporters provided valuable feedback, enabling Hensley and Havens to fine-tune the gameplay experience. Their responsiveness to customer needs and preferences helped shape a product that genuinely connects with people. 

• Creative Marketing and Outreach: From leveraging Hensley’s podcast audience to securing coverage in major publications like The New York Times and Parade, their marketing efforts were strategic and resourceful. These initiatives amplified the brand’s visibility and credibility, driving both boxed game sales and bookings for Virtual Game Nights. 

• Emotional and Social Impact: The game’s ability to create meaningful moments of connection—whether among coworkers, friends, or families—sets it apart from other party games. This emotional resonance has made it more than just entertainment; it’s a tool for fostering relationships. 

• Scalability and New Revenue Streams: The introduction of Virtual Game Nights significantly expanded their market, providing a scalable and profitable revenue stream that complemented physical game sales. Their partnerships with platforms like Elevent and Amphy allowed them to tap into corporate clients and international markets. 

• Personal Investment and Passion: Hensley’s deep personal connection to the game has been a driving force behind its success. His passion for storytelling and fostering human connection infused every aspect of the product, from its development to its marketing. 

Key Lessons to Learn 

1. Progress Beats Perfection: Hensley’s approach to prioritizing action over hesitation underscores the importance of starting where you are, with the resources you have. Waiting for every detail to be perfect can delay progress or prevent you from launching altogether. As he puts it, “You can always tweak things later—the most important step is to just get it out there.” Lesson: Don’t let the pursuit of perfection stall your momentum. Launch, learn, and refine as you go. 

2. Adaptability is Key: The ability to pivot during unforeseen circumstances, such as the pandemic, was instrumental in the success of You Don’t Know My Life! By transitioning from boxed games to Virtual Game Nights, Hensley and Havens tapped into a new, highly profitable market while staying relevant in a changing world. Lesson: Businesses must be flexible and willing to adapt to shifting circumstances or market demands to thrive. 

3. Leverage Your Unique Skills: Hensley’s storytelling background and Havens’ game design expertise were critical to the creation and success of the product. Together, their unique talents brought something fresh and engaging to the market. Lesson: Identify and lean into your strengths, then collaborate with others whose skills complement your own. 

4. Focus on Connection, Not Just Sales: The game’s emotional impact—bringing people closer together—has been a major driver of its popularity. Whether through its boxed format or Virtual Game Nights, You Don’t Know My Life! stands out for its ability to create meaningful moments of connection. Lesson: Products that deliver emotional or relational value often resonate more deeply with customers, building loyalty and word-of-mouth marketing. 

5. Don’t Overlook Small Wins: From playtesting with friends to securing their ideal website URL for just $10, Hensley and Havens capitalized on small victories that, collectively, made a big difference in the game’s success. Lesson: Pay attention to the small opportunities that arise—they can have an outsized impact on your business’s trajectory. 

6. Test and Iterate with Feedback: Playtesting the game with small groups allowed Hensley and Havens to fine-tune everything from the gameplay to the prompts. This ongoing refinement ensured they launched a product that truly resonated with players. Lesson: Use feedback to shape and improve your product or service. Listening to your audience is one of the best ways to ensure success. 

7. Create Multiple Revenue Streams: While boxed game sales provided a steady income, Virtual Game Nights added a scalable, highly profitable revenue stream that helped the business grow. The duo’s willingness to experiment with different formats allowed them to reach new audiences and diversify their income. Lesson: Don’t rely on a single revenue stream. Explore complementary ways to expand your business while staying true to your brand. 

8. Invest in Marketing and Visibility: Strategic PR efforts, such as pitching the game to holiday gift guides, helped land coverage in The New York Times and Parade, boosting sales significantly. Leveraging Hensley’s podcast audience and creating unique marketing assets (like a word cloud of customer reviews) further increased visibility. Lesson: Creative, well-targeted marketing can amplify your reach, even on a limited budget. 

9. Build a Business Around Your Passion: For Hensley, creating the game wasn’t just about revenue—it was a way to share his love of storytelling, foster connection, and take control of his creative career. This deep sense of purpose has fueled his passion for the business and kept him motivated. Lesson: Businesses that align with your personal values and passions are more likely to feel fulfilling and sustainable. 

10. Think Big, but Start Small: Hensley and Havens launched their game through a grassroots crowdfunding effort and grew it steadily over time. Even as they explore larger ambitions—such as collaborations with major retailers or a TV show adaptation—they remain focused on perfecting what’s working now. Lesson: Start small, build a solid foundation, and expand strategically. Big dreams can be achieved incrementally. 

11. Celebrate Autonomy and Ownership: One of the most rewarding aspects of the journey for Hensley has been the freedom to call the shots and create something he fully owns. This autonomy has allowed him to balance creativity and business on his own terms. Lesson: Owning your work and having control over your career can provide a sense of fulfillment and empowerment that’s worth striving for. 

Opportunity Matrix 

Founder Background 

Dennis Hensley, entertainment journalist and podcaster with a strong storytelling background, collaborated with Jeb Havens, a game designer with technical expertise. 

Problem Identification 

People often struggle to connect meaningfully, whether at parties, workplaces, or during remote interactions. Traditional games often lack emotional depth or originality. 

Market Opportunity 

Growing demand for party games with a storytelling component and team-building tools, especially during and after the pandemic when remote work increased the need for connection. 

Competitive Landscape 

Competes with established party games like Cards Against Humanity and What Do You Meme? but differentiates itself through a focus on storytelling and emotional connection. 

Market Research 

Playtesting with small groups to refine questions and gameplay; using customer feedback to identify emotional and entertainment value.  

Business Model 

Combination of physical game sales via Amazon and other platforms, and Virtual Game Nights offered directly to corporate clients or through platforms like Elevent and Amphy. 

Initial Capital 

Raised $12,000 through grassroots crowdfunding to produce the first 1,000 units, with total startup costs of $12,500 including legal fees, website creation, and manufacturing. 

Product/Service Development 

Created prompts leveraging Hensley’s storytelling skills, combined with Havens’ design expertise; partnered with Longpack Games for manufacturing; iteratively refined through playtesting. 

Marketing Strategy 

Leveraged personal networks, PR campaigns, podcast audience, and holiday gift guide placements (The New York Times, Parade); experimented with creative assets like word clouds. 

Milestones 

• First 1,000 units produced by Christmas 2018 

• Pivot to Virtual Game Nights during pandemic 

• Secured corporate clients and expanded internationally via partnerships. 

Scalability 

Virtual Game Nights are highly scalable with minimal overhead; potential for licensing partnerships, retail distribution (e.g., Target), and adaptation into TV or media formats. 

Potential Risks and Challenges 

Reliance on virtual events may face challenges as in-person activities return; limited resources for large-scale marketing; competition from established brands with bigger budgets. 

Key Performance Indicators/Metrics  

• Monthly revenue ($2,500 as of now) 

• Number of Virtual Game Nights booked 

• Customer reviews and feedback 

• Corporate repeat bookings and partnerships established.